Molecules

11 pages, 153 KB

Open AccessArticle

Upgrading SELEX Technology by Using Lambda Exonuclease Digestion for Single-Stranded DNA Generation

by Meltem Avci-Adali, Angel Paul, Nadj Wilhelm, Gerhard Ziemer and Hans Peter Wendel^*

Department of Thoracic, Cardiac, and Vascular Surgery, University Hospital Tuebingen, Calwerstr. 7/1, Tuebingen 72076, Germany

Molecules 2010, 15(1), 1-11; https://doi.org/10.3390/molecules15010001 - 24 Dec 2009

Cited by 118 | Viewed by 19336

Abstract

The generation of single-stranded DNA (ssDNA) molecules plays a key role in the SELEX (Systematic Evolution of Ligands by EXponential enrichment) combinatorial chemistry process and numerous molecular biology techniques and applications, such as DNA sequencing, single-nucleotide polymorphism (SNP) analysis, DNA chips, DNA single-strand [...] Read more.

The generation of single-stranded DNA (ssDNA) molecules plays a key role in the SELEX (Systematic Evolution of Ligands by EXponential enrichment) combinatorial chemistry process and numerous molecular biology techniques and applications, such as DNA sequencing, single-nucleotide polymorphism (SNP) analysis, DNA chips, DNA single-strand conformation polymorphism (SSCP) analysis and many other techniques. The purity and yield of ssDNA can affect the success of each application. This study compares the two ssDNA production methods, the strand separation by streptavidin-coated magnetic beads and alkaline denaturation and the lambda exonuclease digestion, in regard to the purity of generated ssDNA and the efficiency. Here, we demonstrate the considerable benefits of ssDNA production by lambda exonuclease digestion for in vitro selection of DNA aptamers. We believe that the generation of ssDNA aptamers using this method will greatly improve the success rate of SELEX experiments concerning the recovery of target-specific aptamers. Full article

(This article belongs to the Special Issue Combinatorial Chemistry)

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15 pages, 389 KB

Open AccessArticle

Synthesis and in Vitro Cytotoxic Activity of Compounds with Pro-Apoptotic Potential

by Gisell Apicela Soares¹, Renata Barbosa de Oliveira^1,2, Saulo Fernandes de Andrade², Ricardo José Alves², Carlos Leomar Zani¹ and Elaine Maria De Souza-Fagundes^1,3,*

¹ Laboratório de Química de Produtos Naturais, Centro de Pesquisas René Rachou, Fundação Oswaldo Cruz (FIOCRUZ), Av. Augusto de Lima 1715, Belo Horizonte, MG, 30190-002, Brazil

² Departamento de Produtos Farmacêuticos, Faculdade de Farmácia, Universidade Federal de Minas Gerais (UFMG), Avenida Antônio Carlos 6627, Belo Horizonte, MG, 31.270-901, Brazil

³ Departamento de Fisiologia e Biofísica, Instituto de Ciências Biológicas, Universidade Federal de Minas Gerais (UFMG), Avenida Antônio Carlos 6627, Belo Horizonte, MG, 31.270-901, Brazil

Molecules 2010, 15(1), 12-26; https://doi.org/10.3390/molecules15010012 - 24 Dec 2009

Cited by 14 | Viewed by 12250

Abstract

In our search for new anticancer therapies, some compounds synthesized in our lab were selected and their potential cytotoxic activity was evaluated in vitro against two cancer cells lines including a solid tumor (UACC-62, melanoma) and a human lymphoma (JURKAT). Compounds showing cytotoxic [...] Read more.

In our search for new anticancer therapies, some compounds synthesized in our lab were selected and their potential cytotoxic activity was evaluated in vitro against two cancer cells lines including a solid tumor (UACC-62, melanoma) and a human lymphoma (JURKAT). Compounds showing cytotoxic activity were subjected to an apoptosis assay. Two compounds showed promising results. Full article

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13 pages, 665 KB

Open AccessArticle

Synergistic Chondroprotective Effect of α-Tocopherol, Ascorbic Acid, and Selenium as well as Glucosamine and Chondroitin on Oxidant Induced Cell Death and Inhibition of Matrix Metalloproteinase-3—Studies in Cultured Chondrocytes

by Anne-Christi Graeser^1,†, Katri Giller^1,†, Heike Wiegand¹, Luca Barella², Christine Boesch Saadatmandi¹ and Gerald Rimbach^1,*

¹ Institute of Human Nutrition and Food Science, Christian Albrechts University of Kiel, Hermann-Rodewald-Strasse 6, Kiel 24098, Germany

² Bayer Consumer Care AG, Basel, Switzerland

^† These authors contributed equally to this work.

Molecules 2010, 15(1), 27-39; https://doi.org/10.3390/molecules15010027 - 24 Dec 2009

Cited by 13 | Viewed by 14855

Abstract

Overproduction of reactive oxygen species and impaired antioxidant defence accompanied by chronic inflammatory processes may impair joint health. Pro-inflammatory cytokines such as interleukin-1β (IL-1β) and tumor necrosis factor alpha (TNF-α) stimulate the expression of metalloproteinases which degrade the extracellular matrix. Little is known [...] Read more.

Overproduction of reactive oxygen species and impaired antioxidant defence accompanied by chronic inflammatory processes may impair joint health. Pro-inflammatory cytokines such as interleukin-1β (IL-1β) and tumor necrosis factor alpha (TNF-α) stimulate the expression of metalloproteinases which degrade the extracellular matrix. Little is known regarding the potential synergistic effects of natural compounds such as α-tocopherol (α-toc), ascorbic acid (AA) and selenium (Se) on oxidant induced cell death. Furthermore studies regarding the metalloproteinase-3 inhibitory activity of glucosamine sulfate (GS) and chondroitin sulfate (CS) are scarce. Therefore we have studied the effect of α-toc (0.1–2.5 µmol/L), AA (10–50 µmol/L) and Se (1–50 nmol/L) on t-butyl hydroperoxide (t-BHP, 100–500 µmol/L)-induced cell death in SW1353 chondrocytes. Furthermore we have determined the effect of GS and CS alone (100–500 µmol/L each) and in combination on MMP3 mRNA levels and MMP3 secretion in IL-1β stimulated chondrocytes. A combination of α-toc, AA, and Se was more potent in counteracting t-BHP-induced cytotoxicity as compared to the single compounds. Similarly a combination of CS and GS was more effective in inhibiting MMP3 gene expression and secretion than the single components. The inhibition of MMP3 secretion due to GS plus CS was accompanied by a decrease in TNF-α production. Combining natural compounds such as α-toc, AA, and Se as well as GS and CS seems to be a promising strategy to combat oxidative stress and cytokine induced matrix degradation in chondrocytes. Full article

(This article belongs to the Special Issue Vitamins)

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18 pages, 180 KB

Open AccessReview

Severe Embryotoxicity of Artemisinin Derivatives in Experimental Animals, but Possibly Safe in Pregnant Women

by Qigui Li^* and Peter J. Weina

Division of Experimental Therapeutics, Walter Reed Army Institute of Research, 503 Robert Grant Avenue, Silver Spring, MD 20307–5100, USA

Molecules 2010, 15(1), 40-57; https://doi.org/10.3390/molecules15010040 - 25 Dec 2009

Cited by 26 | Viewed by 16806

Abstract

Preclinical studies in rodents have demonstrated that artemisinins, especially injectable artesunate, can induce fetal death and congenital malformations at a low dose range. The embryotoxicity can be induced in those animals only within a narrow window in early embryogenesis. Evidence was presented that [...] Read more.

Preclinical studies in rodents have demonstrated that artemisinins, especially injectable artesunate, can induce fetal death and congenital malformations at a low dose range. The embryotoxicity can be induced in those animals only within a narrow window in early embryogenesis. Evidence was presented that the mechanism by which embryotoxicity of artemisinins occurs seems to be limited to fetal erythropoiesis and vasculogenesis/ angiogenesison the very earliest developing red blood cells, causing severe anemia in the embryos with higher drug peak concentrations. However, this embryotoxicity has not been convincingly observed in clinical trials from 1,837 pregnant women, including 176 patients in the first trimester exposed to an artemisinin agent or artemisinin-based combination therapy (ACT) from 1989 to 2009. In the rodent, the sensitive early red cells are produced synchronously over one day with single or multiple exposures to the drug can result in a high proportion of cell deaths. In contrast, primates required a longer period of treatment of 12 days to induce such embryonic loss. In humans only limited information is available about this stage of red cell development; however, it is known to take place over a longer time period, and it may well be that a limited period of treatment of 2 to 3 days for malaria would not produce serious toxic effects. In addition, current oral intake, the most commonly used route of administration in pregnant women with an ACT, results in lower peak concentration and shorter exposure time of artemisinins that demonstrated that such a concentration–course profile is unlikely to induce the embryotoxicity. When relating the animal and human toxicity of artemisinins, the different drug sensitive period and pharmacokinetic profiles as reviewed in the present report may provide a great margin of safety in the pregnant women. Full article

(This article belongs to the Special Issue Artemisinin (Qinghaosu): Commemorative Issue in Honor of Professor Youyou Tu on the Occasion of her 80th Anniversary)

10 pages, 140 KB

Open AccessArticle

Enaminones in Heterocyclic Synthesis: A Novel Route to Tetrahydropyrimidines, Dihydropyridines, Triacylbenzenes and Naphthofurans under Microwave Irradiation

by Saleh Mohammed Al-Mousawi^*, Morsy Ahmed El-Apasery and Mohamed H. Elnagdi

Department of Chemistry, Faculty of Science; Kuwait University, P.O. Box 5969 Safat, 13060, Kuwait

Molecules 2010, 15(1), 58-67; https://doi.org/10.3390/molecules15010058 - 25 Dec 2009

Cited by 31 | Viewed by 14545

Abstract

Condensation of phthalimidoacetone (1) with DMFDMA (N,N-Dimethylformamide dimethyl acetal) has afforded enaminone 2. Refluxing 2 with equimolecular amounts of benzaldehyde and urea in acetic acid afforded a mixture of tetrahydropyrimidine 5 and the dihydropyridine 6. Compound 2 [...] Read more.

Condensation of phthalimidoacetone (1) with DMFDMA (N,N-Dimethylformamide dimethyl acetal) has afforded enaminone 2. Refluxing 2 with equimolecular amounts of benzaldehyde and urea in acetic acid afforded a mixture of tetrahydropyrimidine 5 and the dihydropyridine 6. Compound 2 undergoes self-condensation on heating in acetic acid or under microwave irradiation in presence of acidic zeolite to give 1,3,5-triacylbenzene 9. Reacting enaminone 11a with naphthoquinone 15 afforded the naphthofuran 18. The possible formation of the aldehyde 19 was excluded based on an HMQC experiment, which revealed that the carbonyl carbon is not linked to any hydrogen. Full article

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15 pages, 188 KB

Open AccessArticle

An Efficient, Mild and Solvent-Free Synthesis of Benzene Ring Acylated Harmalines

by Sabira Begum^*, Farhat Zubair, Syed Nawazish Ali and Bina Shaheen Siddiqui

H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi-75270, Pakistan

Molecules 2010, 15(1), 68-82; https://doi.org/10.3390/molecules15010068 - 28 Dec 2009

Cited by 2 | Viewed by 11221

Abstract

A facile synthesis of a series of benzene ring acylated analogues of harmaline has been achieved by Friedel-Crafts acylation under solvent-free conditions at room temperature using acyl halides/acid anhydrides and AlCl₃. The reaction afforded 10- and 12-acyl analogues of harmaline in [...] Read more.

A facile synthesis of a series of benzene ring acylated analogues of harmaline has been achieved by Friedel-Crafts acylation under solvent-free conditions at room temperature using acyl halides/acid anhydrides and AlCl₃. The reaction afforded 10- and 12-acyl analogues of harmaline in good yield, along with minor quantities of N-acyl-tryptamines and 8-acyl analogues of N-acyltryptamines. Full article

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10 pages, 240 KB

Open AccessArticle

Transition-Metal-Free Highly Efficient Aerobic Oxidation of Sulfides to Sulfoxides under Mild Conditions

by Hua Zhang^1,*, Chunyu Chen¹, Renhua Liu², Qiang Xu¹ and Weiqie Zhao¹

¹ State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, No.158-139, Zhongshan Road, Dalian 116012, China

² School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China

Molecules 2010, 15(1), 83-92; https://doi.org/10.3390/molecules15010083 - 28 Dec 2009

Cited by 25 | Viewed by 12319

Abstract

A highly efficient transition-metal-free catalytic system Br₂/NaNO₂/H₂O has been developed for a robust and economic acid-free aerobic oxidation of sulfides. It is noteworthy that the sulfide function reacts under mild conditions without over-oxidation to sulfone. The role [...] Read more.

A highly efficient transition-metal-free catalytic system Br₂/NaNO₂/H₂O has been developed for a robust and economic acid-free aerobic oxidation of sulfides. It is noteworthy that the sulfide function reacts under mild conditions without over-oxidation to sulfone. The role of NaNO₂as an efficient NO equivalent for the activation of molecular oxygen was identified. Under the optimal conditions, a broad range of sulfide substrates were converted into their corresponding sulfoxides in high yields by molecular oxygen. The present catalytic system utilizes cheap and readily available agents as the catalysts, exhibits high selectivity for sulfoxide products and releases only innocuous water as the by-products. Full article

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1 pages, 19 KB

Open AccessCorrection

Al-Mousawi, S.M., et al. Azolylacetones as Precursors to Indoles and Naphthofurans Facilitated by Microwave Irradiation with Simultaneous Cooling. Molecules 2009, 14, 2976-2984

by Saleh Mohammed Al-Mousawi^* and Morsy Ahmed El-Apasery

Department of Chemistry, Faculty of Science; University of Kuwait, Safat, 13060, P.O. Box 12613, Kuwait

Molecules 2010, 15(1), 93; https://doi.org/10.3390/molecules15010093 - 28 Dec 2009

Viewed by 10148

Abstract

We realized that the title was incorrectly listed in our paper published in Molecules recently [1]. The correct title is indicated below: [...] Full article

6 pages, 240 KB

Open AccessCommunication

Solvent Free, Microwave Assisted Conversion of Aldehydes into Nitriles and Oximes in the Presence of NH₂OH·HCl and TiO₂

by Lucas Villas-Boas Hoelz, Biank Tomaz Gonçalves, José Celestino Barros and Joaquim Fernando Mendes da Silva^*

Departamento de Química Orgânica, Instituto de Química, Universidade Federal do Rio de Janeiro, Av. Athos da Silveira Ramos 149, CT Bloco A, Cidade Universitária, Rio de Janeiro, RJ 21941-909, RJ, Brazil

Molecules 2010, 15(1), 94-99; https://doi.org/10.3390/molecules15010094 - 29 Dec 2009

Cited by 11 | Viewed by 15105

Abstract

Aromatic aldehydes bearing electron-donating groups are easily converted into their respective nitriles using NH₂OH·HCl and TiO₂ under microwave irradiation, while those bearing an electron-withdrawing group give the corresponding oximes. Full article

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14 pages, 558 KB

Open AccessArticle

Determination of Coenzyme A (CoASH) in the Presence of Different Thiols by Using Flow-Injection with a UV/Vis Spectrophotometric Detector and Potentiometric Determination of CoASH Using an Iodide ISE

by Josipa Giljanović^* and Ante Prkić

Department of Analytical Chemistry, Faculty of Chemistry and Chemical Technology, Teslina 10/V, 21000 Split, Croatia

Molecules 2010, 15(1), 100-113; https://doi.org/10.3390/molecules15010100 - 29 Dec 2009

Cited by 13 | Viewed by 19113

Abstract

Coenzyme A (CoA or CoASH) is one of the most important biologically active compounds, and for this reason a reliable, fast and simple determination of CoASH is needed. Here we are described a simple and fast way of determinating CoASH using potentiometric flow-injection [...] Read more.

Coenzyme A (CoA or CoASH) is one of the most important biologically active compounds, and for this reason a reliable, fast and simple determination of CoASH is needed. Here we are described a simple and fast way of determinating CoASH using potentiometric flow-injection analysis and spectrophotometric kinetic determination. The described methods are suitable for use over a wide concentration range (1 × 10^-6–1 × 10^-4 M) of CoASH. Full article

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14 pages, 1340 KB

Open AccessArticle

JNK Contributes to Hif-1α Regulation in Hypoxic Neurons

by Xanthi Antoniou¹, Alessandra Sclip¹, Cristina Ploia¹, Alessio Colombo¹, Gautier Moroy^2,† and Tiziana Borsello^1,*

¹ Istituto di Ricerche Farmacologiche "Mario Negri", Via La Masa 19, 20157 Milano, Italy

² Xigen SA, Rue des Terreaux 17, CH-1015 Lausanne, Switzerland

^† Current address: Molécules Thérapeutiques in silico (MTi), Inserm UMR-S 973, Université Paris Diderot, F-75013 Paris, France.

Molecules 2010, 15(1), 114-127; https://doi.org/10.3390/molecules15010114 - 30 Dec 2009

Cited by 19 | Viewed by 13983

Abstract

Hypoxia is an established factor of neurodegeneration. Nowadays, attention is directed at understanding how alterations in the expression of stress-related signaling proteins contribute to age dependent neuronal vulnerability to injury. The purpose of this study was to investigate how Hif-1α, a major neuroprotective [...] Read more.

Hypoxia is an established factor of neurodegeneration. Nowadays, attention is directed at understanding how alterations in the expression of stress-related signaling proteins contribute to age dependent neuronal vulnerability to injury. The purpose of this study was to investigate how Hif-1α, a major neuroprotective factor, and JNK signaling, a key pathway in neurodegeneration, relate to hypoxic injury in young (6DIV) and adult (12DIV) neurons. We could show that in young neurons as compared to mature ones, the protective factor Hif-1α is more induced while the stress protein phospho-JNK displays lower basal levels. Indeed, changes in the expression levels of these proteins correlated with increased vulnerability of adult neurons to hypoxic injury. Furthermore, we describe for the first time that treatment with the D-JNKI1, a JNK-inhibiting peptide, rescues adult hypoxic neurons from death and contributes to Hif-1α upregulation, probably via a direct interaction with the Hif-1α protein. Full article

(This article belongs to the Special Issue Neuroprotective Strategies)

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10 pages, 223 KB

Open AccessArticle

Synthesis of New Imidazolidin-2,4-dione and 2-Thioxoimidazolidin-4-ones via C-Phenylglycine Derivatives

by José Alixandre De Sousa Luis^1,2, José Maria Barbosa Filho¹, Bruno Freitas Lira¹, Isac Almeida Medeiros¹, Liana Clébia Soares Lima de Morais¹, Alexsandro Fernandes Dos Santos³, Cledualdo Soares de Oliveira³ and Petrônio Filgueiras De Athayde-Filho^1,3,*

¹ Laboratório de Tecnologia Farmacêutica, Universidade Federal da Paraíba, João Pessoa - PB, CEP 58.051-970, Brazil

² Centro de Educação e Saúde, Unidade Acadêmica de Saúde, Universidade Federal de Campina Grande, Cuité - PB, CEP 58.175-000, Brazil

³ Departamento de Química, Universidade Federal da Paraíba, Campus I, João Pessoa - PB, CEP 58059-900, Brazil

Molecules 2010, 15(1), 128-137; https://doi.org/10.3390/molecules15010128 - 30 Dec 2009

Cited by 11 | Viewed by 15520

Abstract

Hydantoins and their derivatives constitute a group of pharmaceutical compounds with anticonvulsant and antiarrhythmic properties, and are also used against diabetes. N-3 and C-5 substituted imidazolidines are examples of such products. As such, we have developed a synthesis of 2,4-dione and 2-thioxo-4-one imidazolidinic [...] Read more.

Hydantoins and their derivatives constitute a group of pharmaceutical compounds with anticonvulsant and antiarrhythmic properties, and are also used against diabetes. N-3 and C-5 substituted imidazolidines are examples of such products. As such, we have developed a synthesis of 2,4-dione and 2-thioxo-4-one imidazolidinic derivatives by reaction of amino acids with C-phenylglycine, phenyl isocyanate and phenyl isothiocyanate. Four amino-derivatives IG(1-4) and eight imidazolidinic derivatives, IM(1-8), were obtained in yields of 70–74%. The mass, infrared, ¹H and ¹³C-NMR spectra of representative products are discussed. Full article

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11 pages, 237 KB

Open AccessArticle

The Anti-HIV Actions of 7- and 10-Substituted Camptothecins

by Yu-Ye Li^1,3,4,5, Shi-Wu Chen^2,*, Liu-Meng Yang¹, Rui-Rui Wang¹, Wei Pang¹ and Yong-Tang Zheng^1,*

¹ Key Laboratory of Animal Models and Human Disease Mechanisms of Chinese Academy of Sciences & Yunnan Province, Kunming Institute of Zoology, Chinese Academy of Sciences, Kunming, Yunnan 650223, China

² School of Pharmacy, Lanzhou University, Lanzhou 730000, China

³ Graduate School of the Chinese Academy of Sciences, Beijing 100039, China

⁴ The First Affiliated Hospital of Kunming Medical College, Kunming, Yunnan 650032, China

⁵ Yunnan Institute of Dermatology & Venereology, Kunming, Yunnan 650032, China

Molecules 2010, 15(1), 138-148; https://doi.org/10.3390/molecules15010138 - 31 Dec 2009

Cited by 16 | Viewed by 12341 | Correction

Abstract

Camptothecin (CPT), a traditional anti-tumor drug, has been shown to possess anti-HIV-1 activity. To increase the antiviral potency, the anti-HIV activities of two CPT derivatives, 10-hydroxy-CPT and 7-hydroxymethyl-CPT, were evaluated in vitro. The therapy index (TI) of CPT, 10-hydroxy-CPT and 7-hydroxymethyl-CPT against [...] Read more.

Camptothecin (CPT), a traditional anti-tumor drug, has been shown to possess anti-HIV-1 activity. To increase the antiviral potency, the anti-HIV activities of two CPT derivatives, 10-hydroxy-CPT and 7-hydroxymethyl-CPT, were evaluated in vitro. The therapy index (TI) of CPT, 10-hydroxy-CPT and 7-hydroxymethyl-CPT against HIV-1_IIIB in C8166 were 24.2, 4.2 and 198.1, and against clinical isolated strain HIV-1_KM018 in PBMC were 10.3, 3.5 and 66.0, respectively. While the TI of CPT, 10-hydroxy-CPT and 7-hydroxymethyl-CPT against HIV-2_CBL-20 were 34.5, 10.7 and 317.0, respectively, and the TI of the three compounds against HIV-2_ROD showed the similar values. However, when the antiviral mechanisms were considered, we found there was no inhibition of 7-hydroxymethyl-CPT on viral cell-to-cell transmission, and was no inhibition on reverse transcriptase, protease or integrase in cell-free systems. 7-Hydroxymethyl-CPT showed no selective killing of chronically infected cells after 3 days of incubation. In conclusion, 7-hydroxymethyl-CPT showed more potent anti-HIV activity, while 10-hydroxy-CPT had less efficient activity, compared with the parent CPT. Though the antiviral mechanisms remain to be further elucidated; the modification of -OH residues at C-7 of CPT could enhance the antiviral activity, while of -OH residues at C-10 of CPT had decreased the antiviral activity, which provides the preliminary modification strategy for anti-viral activities enhancement of this compound. Full article

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1 pages, 61 KB

Open AccessCorrection

Chen, Zheng, et al. Anti-HIV Actions of 7- and 10-Substituted Camptothecins. Molecules, 2010, 15, 138-148

by Yong-Tang Zheng

Key Laboratory of Animal Models and Human Disease Mechanisms of Chinese Academy of Sciences & Yunnan Province, Kunming Institute of Zoology, Chinese Academy of Sciences, Kunming, Yunnan 650223, China

Molecules 2010, 15(1), 149; https://doi.org/10.3390/molecules15010149 - 4 Jan 2010

Viewed by 8599

Abstract

The author list, affiliations and contact information of this paper [1] are revised. [...] Full article

14 pages, 295 KB

Open AccessArticle

Thioacetyl-Terminated Ferrocene-Anthraquinone Conjugates: Synthesis, Photo- and Electrochemical Properties Triggered by Protonation-Induced Intramolecular Electron Transfer

by Wen-Wei Zhang^1,2, Mio Kondo¹, Takako Fujita¹, Kosuke Namiki¹, Masaki Murata¹ and Hiroshi Nishihara^1,*

¹ Department of Chemistry, School of Science, the University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan

² State Key Laboratory of Coordination Chemistry, Coordination Chemistry Institute, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China

Molecules 2010, 15(1), 150-163; https://doi.org/10.3390/molecules15010150 - 4 Jan 2010

Cited by 8 | Viewed by 11585

Abstract

Two thioacetyl-terminated ferrocene-anthraquinone donor-acceptor molecules with different π-electron conjugative units have been synthesized via a series of Stille and Sonagashira reactions. Their photochemical and electrochemical properties before and after addition of an organic acid are investigated, indicating that these complexes are sensitive to [...] Read more.

Two thioacetyl-terminated ferrocene-anthraquinone donor-acceptor molecules with different π-electron conjugative units have been synthesized via a series of Stille and Sonagashira reactions. Their photochemical and electrochemical properties before and after addition of an organic acid are investigated, indicating that these complexes are sensitive to external perturbation of protonation, leading the structural change to an expansion of π-conjugated system by cyclocondensation reaction and promoting intramolecular electron transfer from donor to acceptor. They would be good candidates for studies of novel SAMs, and the properties triggered by protonation-induced intramolecular electron transfer will make the SAMs be useful in designing new functional molecular devices. Full article

(This article belongs to the Special Issue Ferrocenes)

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14 pages, 236 KB

Open AccessArticle

Immunoassay Development for the Class-Specific Assay for Types I and II Pyrethroid Insecticides in Water Samples

by Qi Zhang, Wen Zhang, Xiuping Wang and Peiwu Li^*

Oil Crops Research Institute, Chinese Academy of Agricultural Sciences, Wuhan 430062, China

Molecules 2010, 15(1), 164-177; https://doi.org/10.3390/molecules15010164 - 4 Jan 2010

Cited by 27 | Viewed by 11666

Abstract

Five generic haptens of pyrethoid insecticides, which were classified as three types, were designed and synthesized: the first (hapten 1) is for type I pyrethroids without a cyano group, the second (hapten 2 and XQ) for type II pyrethroids with a cyano group, [...] Read more.

Five generic haptens of pyrethoid insecticides, which were classified as three types, were designed and synthesized: the first (hapten 1) is for type I pyrethroids without a cyano group, the second (hapten 2 and XQ) for type II pyrethroids with a cyano group, and the third (hapten 4 and 5) for both types of pyrethroids with loss of the ester group. The hapten structures were confirmed by MS and ¹H-NMR. Hapten 1 and 2 were conjugated with BSA respectively and haptens 1-5 were conjugated with OVA. Four polyclonal antisera were raised against BSA conjugates including a mixture conjugate, and twenty antibody/coating conjugate combinations were selected for studies of assay sensitivity and specificity for pyrethroids. The study revealed the best combination, which showed equal high sensitivities (I₅₀ is around 0.02 μg mL^-1) to both types of pyrethroids. The immunity results suggest that, with a mixture conjugates, a polyclonal antibody against a group of insecticides can be prepared for multi-residue assays. Full article

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20 pages, 161 KB

Open AccessReview

Click Chemistry for the Synthesis of RGD-Containing Integrin Ligands

by Matteo Colombo^1,* and Aldo Bianchi^2,*

¹ NiKem Research, via Zambeletti 25, 20021 Baranzate, Milan, Italy

² Consorzio Interdisciplinare di Studi Biomolecolari ed Applicazioni Industriali (CISI), Via Fantoli 16/15, 20138 Milan, Italy

Molecules 2010, 15(1), 178-197; https://doi.org/10.3390/molecules15010178 - 6 Jan 2010

Cited by 48 | Viewed by 20149

Abstract

In the last few years click chemistry reactions, and in particular coppercatalyzed cycloadditions, have been used intensively for the preparation of new bioconjugate molecules and materials applicable to biomedical and pharmaceutical areas. This review will be focused on conjugates of the tripeptide Arg-Gly-Asp [...] Read more.

In the last few years click chemistry reactions, and in particular coppercatalyzed cycloadditions, have been used intensively for the preparation of new bioconjugate molecules and materials applicable to biomedical and pharmaceutical areas. This review will be focused on conjugates of the tripeptide Arg-Gly-Asp formed by means of click chemistry reactions. This sequence is a well known binding motif for specific transmembrane proteins and is involved in cellular adhesion to the extracellular matrix, allowing the selective recognition of the biomolecule or polymer in which it is incorporated. Full article

(This article belongs to the Special Issue Click Chemistry)

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17 pages, 215 KB

Open AccessArticle

Elucidating the Structure-Activity Relationships of the Vasorelaxation and Antioxidation Properties of Thionicotinic Acid Derivatives

by Supaluk Prachayasittikul^1,*, Orapin Wongsawatkul², Apilak Worachartcheewan³, Chanin Nantasenamat³, Somsak Ruchirawat⁴ and Virapong Prachayasittikul^3,*

¹ Department of Chemistry, Faculty of Science, Srinakharinwirot University, Bangkok 10110, Thailand

² Department of Pharmacology, Faculty of Medicine, Srinakharinwirot University, Bangkok 10110, Thailand

³ Department of Clinical Microbiology, Faculty of Medical Technology, Mahidol University, Bangkok 10700, Thailand

⁴ Chulabhorn Research Institute and Chulabhorn Graduate Institute, Bangkok 10210, Thailand

Molecules 2010, 15(1), 198-214; https://doi.org/10.3390/molecules15010198 - 6 Jan 2010

Cited by 30 | Viewed by 12410

Abstract

Nicotinic acid, known as vitamin B₃, is an effective lipid lowering drug and intense cutaneous vasodilator. This study reports the effect of 2-(1-adamantylthio)nicotinic acid (6) and its amide 7 and nitrile analog 8 on phenylephrine-induced contraction of rat thoracic [...] Read more.

Nicotinic acid, known as vitamin B₃, is an effective lipid lowering drug and intense cutaneous vasodilator. This study reports the effect of 2-(1-adamantylthio)nicotinic acid (6) and its amide 7 and nitrile analog 8 on phenylephrine-induced contraction of rat thoracic aorta as well as antioxidative activity. It was found that the tested thionicotinic acid analogs 6-8 exerted maximal vasorelaxation in a dose-dependent manner, but their effects were less than acetylcholine (ACh)-induced nitric oxide (NO) vasorelaxation. The vasorelaxations were reduced, apparently, in both N^G-nitro-L-arginine methyl ester (L-NAME) and indomethacin (INDO). Synergistic effects were observed in the presence of L-NAME plus INDO, leading to loss of vasorelaxation of both the ACh and the tested nicotinic acids. Complete loss of the vasorelaxation was noted under removal of endothelial cells. This infers that the vasorelaxations are mediated partially by endothelium-induced NO and prostacyclin. The thionicotinic acid analogs all exhibited antioxidant properties in both 2,2-diphenyl-1-picrylhydrazyl (DPPH) and superoxide dismutase (SOD) assays. Significantly, the thionicotinic acid 6 is the most potent vasorelaxant with ED₅₀ of 21.3 nM and is the most potent antioxidant (as discerned from DPPH assay). Molecular modeling was also used to provide mechanistic insights into the vasorelaxant and antioxidative activities. The findings reveal that the thionicotinic acid analogs are a novel class of vasorelaxant and antioxidant compounds which have potential to be further developed as promising therapeutics. Full article

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11 pages, 595 KB

Open AccessArticle

Screening and Improvement of an Anti-VEGF DNA Aptamer

by Yoshihiko Nonaka, Koji Sode and Kazunori Ikebukuro^*

Department of Biotechnology & Life science, Tokyo University of Agriculture and Technology, 2-24-21 Naka Cho, Koganei, Tokyo, 1848588, Japan

Molecules 2010, 15(1), 215-225; https://doi.org/10.3390/molecules15010215 - 7 Jan 2010

Cited by 133 | Viewed by 16010

Abstract

To obtain an aptamer with a high affinity for vascular endothelial growth factor (VEGF), we focused on the receptor-binding domain (RBD) of VEGF as a target epitope. Three rounds of screening gave Vap7, which bound to the VEGF isoforms VEGF₁₂₁ and VEGF [...] Read more.

To obtain an aptamer with a high affinity for vascular endothelial growth factor (VEGF), we focused on the receptor-binding domain (RBD) of VEGF as a target epitope. Three rounds of screening gave Vap7, which bound to the VEGF isoforms VEGF₁₂₁ and VEGF₁₆₅ with K_D values of 1.0 nM and 20 nM, respectively. Moreover, Vap7 showed specificity within the VEGF family. Secondary structure predictions and circular dicrhoism suggested that Vap7 folds into a G-quadruplex structure. We obtained a mutant aptamer that contains only this region of the aptamer sequence. This truncated mutant (V7t1) bound to both VEGF₁₂₁ and VEGF₁₆₅ with K_D values of 1.1 nM and 1.4 nM, respectively. Its sequence was 5'-TGTGGGGGTGGACGGGCCGGGTAGA-3', and it appeared to form a G-quadruplex structure. We also produced an aptamer heterodimer consisting of our previously derived aptamer (del5-1), which binds to the heparin-binding domain of VEGF, linked to V7t1. The resulting heterodimer bound strongly to VEGF₁₆₅ with a K_D value of 4.7 × 10² pM. Full article

(This article belongs to the Special Issue High-throughput Screening)

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7 pages, 414 KB

Open AccessCommunication

Synthesis and Structure of D_3h-Symmetric Triptycene Trimaleimide

by Cristiano Zonta^1,2,*, Ottorino De Lucchi², Anthony Linden³ and Martin Lutz⁴

¹ Dipartimento di Scienze Chimiche, Università di Padova, via Marzolo 1, 35131 Padova, Italy

² Dipartimento di Chimica, Università Ca’ Foscari di Venezia, Dorsoduro 2137, I-30123 Venezia, Italy

³ Institute of Organic Chemistry, University of Zurich, Winterthurerstrasse 190, CH-8057 Zurich, Switzerland

⁴ Bijvoet Centre for Biomolecular Research, Crystal and Structural Chemistry, Utrecht University, Padualaan 8, 3584 CH Utrecht, The Netherlands

Molecules 2010, 15(1), 226-232; https://doi.org/10.3390/molecules15010226 - 7 Jan 2010

Cited by 9 | Viewed by 17305

Abstract

A new D_3h symmetric triptycene derivative has been synthesized with the aim of obtaining molecules that are able to assemble into porous structures, and can be used in the development of new ligands. The synthesis involves a Diels-Alder reaction as the key [...] Read more.

A new D_3h symmetric triptycene derivative has been synthesized with the aim of obtaining molecules that are able to assemble into porous structures, and can be used in the development of new ligands. The synthesis involves a Diels-Alder reaction as the key step, followed by an oxidation and the formation of a maleimide ring. Triptycene trimaleimide furnished single crystals which have been analyzed by means of X-ray diffraction. Full article

(This article belongs to the Special Issue Supramolecular Assembly)

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8 pages, 193 KB

Open AccessArticle

Determination of the Volatile Composition in Essential Oil of Descurainia sophia (L.) Webb ex Prantl (Flixweed) by Gas Chromatography/Mass Spectrometry (GC/MS)

by Jing Li¹, Xingang Liu¹, Fengshou Dong¹, Jun Xu¹, Yongquan Zheng^1,* and Weili Shan²

¹ Key Laboratory of Pesticide Chemistry and Application, Institute of Plant Protection, Chinese Academy of Agricultural Sciences, Ministry of Agriculture, Beijing, 100193, China

² Institute for Control of Agrochemicals, Ministry of Agriculture, Beijing, 100125, China

Molecules 2010, 15(1), 233-240; https://doi.org/10.3390/molecules15010233 - 8 Jan 2010

Cited by 39 | Viewed by 13885

Abstract

Exhaustive hydro-distillation of Descurainia sophia (L.) Webb ex Prantl (flixweed) collected from two different locations (Cangzhou city-Sample 1 and Beijing city-Sample 2) gave in both cases yellowish colored oils in 0.31 and 0.26% yield, respectively. Detailed chemical composition of the essential oils was [...] Read more.

Exhaustive hydro-distillation of Descurainia sophia (L.) Webb ex Prantl (flixweed) collected from two different locations (Cangzhou city-Sample 1 and Beijing city-Sample 2) gave in both cases yellowish colored oils in 0.31 and 0.26% yield, respectively. Detailed chemical composition of the essential oils was analyzed by GC and GC/MS, and forty and thirty-eight compounds were identified. The results indicated that the most abundant component of Sample 1were cis-β-ocimene (20.1%), menthol (11.27%), neoisomenthyl acetate (3.5%), alloaromadendrene (2.28%) and longicyclene (2.25%). Compared with the constituents of Sample 1, several chemical compounds such as 1,8-cineole, α-eudesmol, cis, trans-farnesol and β-pinene were not detected in Sample 2 although it was similarly dominated by cis-β-ocimene (17.12%), menthol (10.7%) and neoisomenthyl acetate (2.96%). Final analysis of the chemical constituents in the essential oils of the two samples showed similarity in their chemical composition, but the relative content of all shared chemical constituents in Sample 2 was lower than that in Sample 1. Full article

10 pages, 135 KB

Open AccessArticle

Effects of Volatile Components and Ethanolic Extract from Eclipta prostrata on Proliferation and Differentiation of Primary Osteoblasts

by Xiong-Hao Lin^1,2,†, Yan-Bin Wu^1,†, Shan Lin¹, Jian-Wei Zeng¹, Pei-Yuan Zeng^1,2 and Jin-Zhong Wu^1,2,*

¹ Academy of Integrative Medicine, Fujian University of Traditional Chinese Medicine, Fuzhou, Fujian 350108, China

² Department of Pharmacy, Fujian University of Traditional Chinese Medicine, Fuzhou, Fujian 350108, China

^† These authors contributed equally to this work.

Molecules 2010, 15(1), 241-250; https://doi.org/10.3390/molecules15010241 - 8 Jan 2010

Cited by 43 | Viewed by 16458

Abstract

Eclipta prostrata, an aromatic plant, is known in Chinese herbal medicine for the treatment of various kidney diseases. In the present study, the volatile components were isolated from the aerial parts of this plant by hydrodistillation and analysed by GC–MS. A total [...] Read more.

Eclipta prostrata, an aromatic plant, is known in Chinese herbal medicine for the treatment of various kidney diseases. In the present study, the volatile components were isolated from the aerial parts of this plant by hydrodistillation and analysed by GC–MS. A total of 55 compounds, which were the major part (91.7%) of the volatiles, were identified by matching mass spectra with a mass spectrum library (NIST 05.L). The main components were as follows: heptadecane (14.78%), 6,10,14-trimethyl-2-pentadecanone (12.80%), n-hexadecanoic acid (8.98%), pentadecane (8.68%), eudesma-4(14),11-diene (5.86%), phytol (3.77%), octadec-9-enoic acid (3.35%), 1,2-benzenedicarboxylic acid diisooctyl ester (2.74%), (Z,Z)-9,12-octadecadienoic acid (2.36%), (Z)-7,11-dimethyl-3-methylene-1,6,10-dodecatriene (2.08%) and (Z,Z,Z)-1,5,9,9-tetramethyl-1,4,7-cycloundecatriene (2.07%). The effects of volatile components and ethanolic extract from the aerial parts of this plant on the proliferation and differentiation of primary osteoblasts were evaluated by the MTT method and measuring the activity of alkaline phosphatase (ALP activity). Both volatile components and ethanolic extract (1 μg/mL to 100 μg/mL) significantly (p < 0.01) stimulated the proliferation and increased the ALP activity of primary osteoblasts. These results propose that E. prostrata can play an important role in osteoblastic bone formation, and may possibly lead to the development of bone-forming drugs. Full article

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7 pages, 136 KB

Open AccessCommunication

Inhibition of Oxidation of Aqueous Emulsions of Omega-3 Fatty Acids and Fish Oil by Phloretin and Phloridzin

by H. P. Vasantha Rupasinghe^* and Afsana Yasmin

Tree Fruit Bio-product Research Program, Nova Scotia Agricultural College, P.O. Box 550, Truro, NS, B2N 5E3, Canada

Molecules 2010, 15(1), 251-257; https://doi.org/10.3390/molecules15010251 - 11 Jan 2010

Cited by 64 | Viewed by 13267

Abstract

The antioxidant properties of two apple dihydrochalcones, namely phloretin and phloridzin, were evaluated and compared with those of α-tocopherol and butylated hydroxytoluene (BHT). The effects were studied in an oil-in-water emulsion system containing methyl linolenate (ML), methyl eicosapentaenoate (MEPA), and methyl docosahexaenoate (MDHA) [...] Read more.

The antioxidant properties of two apple dihydrochalcones, namely phloretin and phloridzin, were evaluated and compared with those of α-tocopherol and butylated hydroxytoluene (BHT). The effects were studied in an oil-in-water emulsion system containing methyl linolenate (ML), methyl eicosapentaenoate (MEPA), and methyl docosahexaenoate (MDHA) in which oxidation was initiated by the peroxyl radical generator 2,2-azobis(2-amidinopropane) dihydrochloride (AAPH) and in fish oil where oxidation was initiated thermally. In the emulsion system, phloretin (1 and 5 mM) completely inhibited the oxidation of ML tested as evidenced by the thiobarbituric acid reactive substances (TBARS) assay. Under the same conditions, phloridzin was less effective than phloretin, but still more effective than α-tocopherol. Both phloretin and phloridzin molecules had a marginal inhibitory effect against oxidation of fish oil induced by heating at 70 °C for 3 hours, when compared to BHT. These results indicate that phloretin and phloridzin have the potential to suppress lipid oxidation in polyunsaturated fatty acid (PUFA) containing foods. Full article

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12 pages, 551 KB

Open AccessArticle

Comparison of Dissolution and Surface Reactions Between Calcite and Aragonite in L-Glutamic and L-Aspartic Acid Solutions

by Miyoung Ryu^1,2, Hwan Kim², Mihee Lim¹, Kwangsuk You¹ and Jiwhan Ahn^1,*

¹ Korea Institute of Geoscience and Mineral Resources, 92 Gahwangno, Yuseung-gu, Daejeon, 305-350, Korea

² School of Materials Science and Engineering, Seoul National University, Sillim-dong, Gwanak-gu, Seoul, 151-742, Korea

Molecules 2010, 15(1), 258-269; https://doi.org/10.3390/molecules15010258 - 11 Jan 2010

Cited by 29 | Viewed by 11285

Abstract

We have investigated dissolution and surface reaction of calcite and aragonite in amino acid solutions of L-glutamic (L-glu) and L-aspartic acid (L-asp) at weak acidity of above pH 3. The surface reactions of calcite and aragonite were related with the dissolution. Calcite was [...] Read more.

We have investigated dissolution and surface reaction of calcite and aragonite in amino acid solutions of L-glutamic (L-glu) and L-aspartic acid (L-asp) at weak acidity of above pH 3. The surface reactions of calcite and aragonite were related with the dissolution. Calcite was dissolved in both solutions but the dissolution was limited by an adsorption of Ca-carboxylate salt. Aragonite was neither dissolved nor reacted in amino acid solutions because the crystal surface consisted of a hard to dissolve structure. Full article

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10 pages, 174 KB

Open AccessArticle

Synthesis and Vasorelaxant and Platelet Antiaggregatory Activities of a New Series of 6-Halo-3-phenylcoumarins

by Elías Quezada¹, Giovanna Delogu^2,*

, Carmen Picciau², Lourdes Santana³, Gianni Podda², Fernanda Borges¹, Verónica García-Morales⁴, Dolores Viña⁴ and Francisco Orallo⁴

¹ Chemistry Department, Faculty of Sciences, University Porto, 4169-007 Porto, Portugal

² Dipartimento Farmaco Chimico Tecnologico, Universita degli Studi di Cagliari, Via Ospedale 72, 09124 Cagliari, Italy

³ Department of Organic Chemistry, Faculty of Pharmacy, University of Santiago de Compostela, 15782 Santiago de Compostela, Spain

⁴ Department of Pharmacology, Faculty of Pharmacy, University of Santiago de Compostela, 15782 Santiago de Compostela, Spain

Molecules 2010, 15(1), 270-279; https://doi.org/10.3390/molecules15010270 - 12 Jan 2010

Cited by 72 | Viewed by 13042

Abstract

A series of 6-halo-3-hydroxyphenylcoumarins (resveratrol-coumarins hybrid derivatives) was synthesized in good yields by a Perkin reaction followed by hydrolysis. The new compounds were evaluated for their vasorelaxant activity in intact rat aorta rings pre-contracted with phenylephrine (PE), as well as for their inhibitory [...] Read more.

A series of 6-halo-3-hydroxyphenylcoumarins (resveratrol-coumarins hybrid derivatives) was synthesized in good yields by a Perkin reaction followed by hydrolysis. The new compounds were evaluated for their vasorelaxant activity in intact rat aorta rings pre-contracted with phenylephrine (PE), as well as for their inhibitory effects on platelet aggregation induced by thrombin in washed human platelets. These compounds concentration-dependently relaxed vascular smooth muscle and some of them showed a platelet antiaggregatory activity that was up to thirty times higher than that shown by trans-resveratrol and some other previously synthesized derivatives. Full article

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8 pages, 414 KB

Open AccessArticle

Ultrasonic Method for the Preparation of Organic Porphyrin Nanoparticles

by Mohamad Mehdi Kashani-Motlagh, Rahmatollah Rahimi^* and Marziye Javaheri Kachousangi

Department of Chemistry, Iran University of Science and Technology, Narmak, Tehran, Iran

Molecules 2010, 15(1), 280-287; https://doi.org/10.3390/molecules15010280 - 12 Jan 2009

Cited by 15 | Viewed by 8419

Abstract

We report the synthesis and optical properties of organic porphyrin nanoparticles with narrow size distribution and good dispersibility. Nanoparticles were produced by a combination of precipitation and sonication, termed the “ultrasonic method”. The resulting [tetrakis(para-chlorophenyl)porphyrin]TClPP nanoparticles were stable in solution without [...] Read more.

We report the synthesis and optical properties of organic porphyrin nanoparticles with narrow size distribution and good dispersibility. Nanoparticles were produced by a combination of precipitation and sonication, termed the “ultrasonic method”. The resulting [tetrakis(para-chlorophenyl)porphyrin]TClPP nanoparticles were stable in solution without precipitation for at least 30 days. No self aggregation of the constituent porphyrin chromophores was observed. The TClPP nanoparticles exhibited interesting optical properties, particulalrly a large bathochromic shift in the absorption spectra. Full article

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17 pages, 213 KB

Open AccessArticle

Investigating the Activity Spectrum for Ring-Substituted 8-Hydroxyquinolines

by Robert Musiol^1,*, Josef Jampilek^2,3, Jacek E. Nycz¹, Matus Pesko⁴, James Carroll⁵, Katarina Kralova⁶, Marcela Vejsova⁷, Jim O'Mahony⁵, Aidan Coffey⁵, Anna Mrozek¹ and Jaroslaw Polanski¹

¹ Institute of Chemistry, University of Silesia, Szkolna 9, 40007 Katowice, Poland

² Zentiva k.s., U kabelovny 130, 102 37 Prague, Czech Republic

³ Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1/3, 61242 Brno, Czech Republic

⁴ Department of Ecosozology and Physiotactics, Faculty of Natural Sciences, Comenius University, Mlynska dolina Ch-2, 84215 Bratislava, Slovakia

⁵ Department of Biological Sciences, Cork Institute of Technology, Bishopstown, Cork, Ireland

⁶ Institute of Chemistry, Faculty of Natural Sciences, Comenius University, Mlynska dolina Ch-2, 84215 Bratislava, Slovakia

⁷ Department of Biological and Medical Sciences, Faculty of Pharmacy in Hradec Kralove, Charles University in Prague, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic

Molecules 2010, 15(1), 288-304; https://doi.org/10.3390/molecules15010288 - 12 Jan 2010

Cited by 51 | Viewed by 14764

Abstract

In this study, a series of fourteen ring-substituted 8-hydroxyquinoline derivatives were prepared. The synthesis procedures are presented. The compounds were analyzed using RP-HPLC to determine lipophilicity. They were tested for their activity related to inhibition of photosynthetic electron transport (PET) in spinach ( [...] Read more.

In this study, a series of fourteen ring-substituted 8-hydroxyquinoline derivatives were prepared. The synthesis procedures are presented. The compounds were analyzed using RP-HPLC to determine lipophilicity. They were tested for their activity related to inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. Primary in vitro screening of the synthesized compounds was also performed against four mycobacterial strains and against eight fungal strains. Several compounds showed biological activity comparable with or higher than the standards isoniazid or fluconazole. For all the compounds, the relationships between the lipophilicity and the chemical structure of the studied compounds are discussed. Full article

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10 pages, 163 KB

Open AccessArticle

Analysis of the Main Nucleosides in Cordyceps Sinensis by LC/ESI-MS

by Jian-Wei Xie¹, Lan-Fang Huang^1,*, Wei Hu¹, Yun-Biao He² and Kin Ping Wong³

¹ Department of Chemistry and Pharmaceutical, Quzhou College, Quzhou 324000, China

² Changde Institute for Drug Control, Changde 415000, China

³ Biology Department, College of Science and Mathematics, California State University-Fresno, Fresno, CA 93740, USA

Molecules 2010, 15(1), 305-314; https://doi.org/10.3390/molecules15010305 - 13 Jan 2010

Cited by 39 | Viewed by 15231

Abstract

A sensitive, selective and reliable liquid chromatography-mass spectrometry coupled with electrospray ionization interface method for simultaneous separation and determination of thymine, adenine, adenosine and cordycepin in Cordyceps sinensis has been established. The optimum separation for these analytes was achieved using a gradient elution [...] Read more.

A sensitive, selective and reliable liquid chromatography-mass spectrometry coupled with electrospray ionization interface method for simultaneous separation and determination of thymine, adenine, adenosine and cordycepin in Cordyceps sinensis has been established. The optimum separation for these analytes was achieved using a gradient elution system and a 2.0 × 150 mm Shimadzu VP-ODS column. 2-Chloroadenosine was used as internal standard for this assay. [M+H]⁺ions at m/z 127, 136, 268, 252 and 302 were chosen and selective ion monitoring (SIM) mode was used for quantitative analysis of the four main nucleosides. The regression equations were linear in the range of 1.0–117.5 μg·mL^-1 for thymine, 1.8-127.0 μg·mL^-1 for adenine, 0.6-114.0 μg·mL^-1 for adenosine and 0.5-107.5 μg·mL^-1 for cordycepin. The limits of quantitation (LOQ) and detection (LOD) were 1.0 and 0.2 μg·mL^-1 for thymine, 1.8 and 0.6 μg·mL^-1 for adenine, 0.6 and 0.1 μg·mL^-1 for adenosine and 0.5 and 0.1 μg·mL^-1 for cordycepin, respectively. The recoveries of the four nucleosides ranged from 98.47 to 99.32%. The developed method was successfully used to determine nucleosides in Cordyceps sinensis from different sources. Full article

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16 pages, 178 KB

Open AccessArticle

Palladium(II)/Cationic 2,2’-Bipyridyl System as a Highly Efficient and Reusable Catalyst for the Mizoroki-Heck Reaction in Water

by Shao-Hsien Huang, Jun-Rong Chen and Fu-Yu Tsai^*

Institute of Organic and Polymeric Materials, National Taipei University of Technology, 1, Section 3, Chung-Hsiao E. Rd., Taipei 106, Taiwan

Molecules 2010, 15(1), 315-330; https://doi.org/10.3390/molecules15010315 - 12 Jan 2010

Cited by 62 | Viewed by 12705

Abstract

A water-soluble and air-stable Pd(NH₃)₂Cl₂/cationic 2,2’-bipyridyl system was found to be a highly-efficient and reusable catalyst for the coupling of aryl iodides and alkenes in neat water using Bu₃N as a base. The reaction was [...] Read more.

A water-soluble and air-stable Pd(NH₃)₂Cl₂/cationic 2,2’-bipyridyl system was found to be a highly-efficient and reusable catalyst for the coupling of aryl iodides and alkenes in neat water using Bu₃N as a base. The reaction was conducted at 140 °C in a sealed tube in air with a catalyst loading as low as 0.0001 mol % for the coupling of activated aryl iodides with butyl and ethyl acrylates, providing the corresponding products in good to excellent yields with very high turnover numbers. In the case of styrene, Mizoroki-Heck coupling products were obtained in good to high yields by using a greater catalyst loading (1 mol %) and TBAB as a phase-transfer agent. After extraction, the residual aqueous solution could be reused several times with only a slight decrease in its activity, making the Mizoroki-Heck reaction “greener”. Full article

(This article belongs to the Special Issue Heck Coupling)

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10 pages, 184 KB

Open AccessArticle

Substituted Pyrazinecarboxamides as Abiotic Elicitors of Flavolignan Production in Silybum marianum (L.) Gaertn Cultures in Vitro

by Lenka Tůmová^1,*, Jiří Tůma², Klara Megušar¹ and Martin Doležal¹

¹ Faculty of Pharmacy in Hradec Králové, Charles University in Prague, Heyrovského 1203, 500 05 Hradec Králové, Czech Republic

² Department of Biology, Faculty of Education, University of Hradec Králové, Víta Nejedlého 573, 500 03 Hradec Králové, Czech Republic

Molecules 2010, 15(1), 331-340; https://doi.org/10.3390/molecules15010331 - 14 Jan 2010

Cited by 35 | Viewed by 14023

Abstract

Substituted pyrazinecarboxamides markedly influenced production of flavonolignans in Silybum marianum callus and suspension cultures. In this study the effect of two compounds, N-(3-iodo-4-methylphenyl)pyrazine-2-carboxamide (1) and N-(3-iodo-4-methylphenyl)-5-tert-butyl-pyrazine-2-carboxamide (2), as abiotic elicitors on flavono-lignan production in callus [...] Read more.

Substituted pyrazinecarboxamides markedly influenced production of flavonolignans in Silybum marianum callus and suspension cultures. In this study the effect of two compounds, N-(3-iodo-4-methylphenyl)pyrazine-2-carboxamide (1) and N-(3-iodo-4-methylphenyl)-5-tert-butyl-pyrazine-2-carboxamide (2), as abiotic elicitors on flavono-lignan production in callus culture of S. marianum was investigated. Silymarin complex compounds have hepatoprotective, anticancer and also hypocholesterolemic activity. In vitro flavonolignan concentration in cells is very low and the elicitation is one of the methods to increase production. Elicitors were tested at three concentrations and at different culture times. In the case of elicitation with 1, the greatest increase of flavonolignan and taxifoline production was observed at concentration c_1a after 6-hours of elicitation and after 24 and 72-hours at concentration c_1b. However, increased production of silychristin, one of the compounds in the silymarin complex, was achieved after only 6-hours elicitation with c_1a (2.95 × 10^-4 mol/L). The content of silychristin was 2-times higher compared to the control sample. An increased production of silychristin was reached with compound 2 at the concentration c₂ (2.53 × 10^-3 mol/L) after 72 h of elicitation. The production of silychristin in this case was increased 12-times compared to control. Full article

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11 pages, 98 KB

Open AccessArticle

Identification and Comparative Quantification of Bio-Active Phthalides in Essential Oils from Si-Wu-Tang, Fo-Shou-San, Radix Angelica and Rhizoma Chuanxiong

by Yuping Tang, Min Zhu, Sheng Yu, Yongqing Hua, Jin-Ao Duan^*, Shulan Su, Xu Zhang, Yin Lu and Anwei Ding

Jiangsu Key Laboratory for TCM Formulae Research, Nanjing University of Chinese Medicine, Nanjing 210046, China

Molecules 2010, 15(1), 341-351; https://doi.org/10.3390/molecules15010341 - 15 Jan 2010

Cited by 52 | Viewed by 14790

Abstract

Phthalides are important bio-active constituents in Si-Wu-Tang and Fo-Shou-San, two commonly used Traditional Chinese Medicine (TCM) combined prescriptions mainly derived from Radix Angelica and Rhizoma Chuanxiong. In this paper, the contents of eight phthalides, including Z-ligustilide, E-ligustilide, Z-butylenephthalide, E-butylene-phthalide, [...] Read more.

Phthalides are important bio-active constituents in Si-Wu-Tang and Fo-Shou-San, two commonly used Traditional Chinese Medicine (TCM) combined prescriptions mainly derived from Radix Angelica and Rhizoma Chuanxiong. In this paper, the contents of eight phthalides, including Z-ligustilide, E-ligustilide, Z-butylenephthalide, E-butylene-phthalide, 3-butylphthalide, neocnidilide and senkyunolide A were determined or estimated by gas chromatography–mass spectrometry (GC-MS). The results showed GC-MS was a simple, rapid, and high sensitive method for analyzing phthalides in Si-Wu-Tang, Fo-Shou-San, Radix Angelica and Rhizoma Chuanxiong, and the extractable contents of each phthalides including Z-ligustilide, E-ligustilide, Z-butylenephthalide, etc. varied after Radix Angelica, Rhizoma Chuanxiong were combined into a formulation, such as Si-Wu-Tang and Fo-Shou-San. Furthermore, inhibition activity of essential oils from Si-Wu-Tang, Fo-Shou-San, Radix Angelica and Rhizoma Chuanxiong on uterine contraction was tested in an in vitro assay, and the results showed that the activity of the essential oil is higher as the content of the phthalides increase, which demonstrated that phthalides are possibly main active components inhibiting mice uterine contraction in vitro. All of the results suggested that comparative analysis of chemical components and pharmacological activities of each herb and formula is possibly helpful to elucidate the active components in traditional Chinese medicine, and to reveal the compatibility mechanism of TCM formulae. Full article

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22 pages, 489 KB

Open AccessReview

Interest of Fluorescence Derivatization and Fluorescence Probe Assisted Post-column Detection of Phospholipids: A Short Review

by Hanadi Ibrahim, Eric Caudron^*, Athena Kasselouri and Pratrice Prognon

Groupe de Chimie Analytique de Paris-Sud, Faculty of Pharmacy, University Paris-Sud, EA 4041, IFR 141, 92296 Châtenay-Malabry, France

Molecules 2010, 15(1), 352-373; https://doi.org/10.3390/molecules15010352 - 18 Jan 2010

Cited by 26 | Viewed by 16304

Abstract

Phospholipids are essential constituents of all living cell membranes. There are many analytical methods available for the quantitative and qualitative determination of phospholipids, but since these molecules lack chromophores, common absorbance based methods are of limited use. Beside mass spectrometry, some less specific [...] Read more.

Phospholipids are essential constituents of all living cell membranes. There are many analytical methods available for the quantitative and qualitative determination of phospholipids, but since these molecules lack chromophores, common absorbance based methods are of limited use. Beside mass spectrometry, some less specific approaches that are routinely used are evaporative light scattering detection or fluorescence, which exhibit sufficient sensitivity. Here, we focus on fluorescence, which remains an interesting way to quantify phospholipids. Two ways of detecting phospholipids by fluorescence are possible coupled with separation techniques such as thin layer chromatography (TLC), high performance liquid chromatography (HPLC) and capillary electrophoresis (CE): firstly, pre-column derivatization procedures and secondly, probe assisted post-column detection with suitable fluorescence reagents. In both cases, the common purpose is to increase the detection sensitivity. It is shown that, whereas pre-column derivatization is characterized by selectivity due to the chemical functionality of the analyte involved in the derivatization process, in supramolecular post-column derivatization, the selectivity only proceeds from the capacity of the lipid to involve supramolecular assemblies with a fluorescence probe. The aim of this review is to summarize available experiments concerning fluorescence detection of phospholipids. The interest and limitation of such detection approaches are discussed. Full article

(This article belongs to the Special Issue Phospholipids)

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11 pages, 138 KB

Open AccessArticle

A Simple Preparation of 2,3,4,6-Tetra-O-acyl-Gluco-, Galacto- and Mannopyranoses and Relevant Theoretical Study

by Zerong Daniel Wang^1,*, Yirong Mo^2,*, Chiao-Lun Chiou^1,3 and Minghong Liu^2,4

¹ Department of Chemistry, School of Science and Computer Engineering, University of Houston-Clear Lake, 2700 Bay Area Boulevard, Houston, TX 77058, USA

² Department of Chemistry, Western Michigan University, Kalamazuo, MI 49008, USA

³ Department of Chemical & Biomolecular Engineering, University of Houston, Houston, TX 77204-4004, USA

⁴ Chemistry Department, University of North Carolina-Charlotte, Charlotte, NC 28223, USA

Molecules 2010, 15(1), 374-384; https://doi.org/10.3390/molecules15010374 - 18 Jan 2010

Cited by 9 | Viewed by 19610

Abstract

The deacylation of glucose, galactose and mannose pentaacetates, galactose and mannose penta(3-bromo)benzoates, as well as the dealkylation of 2,3,4,6-tetra-O-acetyl and 2,3,4,6-tetra-O-(3-bromo)benzoyl methyl α-D-glucopyranosides have been studied. In addition, a computational study on the deacylation of β-D [...] Read more.

The deacylation of glucose, galactose and mannose pentaacetates, galactose and mannose penta(3-bromo)benzoates, as well as the dealkylation of 2,3,4,6-tetra-O-acetyl and 2,3,4,6-tetra-O-(3-bromo)benzoyl methyl α-D-glucopyranosides have been studied. In addition, a computational study on the deacylation of β-D-glucose pentaacetate has been carried out with density functional theory (B3LYP/6-31G*). The anomeric effect during deacetylation and dealkylation has been clearly demonstrated in both experimental and computational results. Full article

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14 pages, 1214 KB

Open AccessArticle

Luteolin Isolated from the Flowers of Lonicera japonica Suppresses Inflammatory Mediator Release by Blocking NF-κB and MAPKs Activation Pathways in HMC-1 Cells

by Ok-Hwa Kang^1,2, Jang-Gi Choi¹, John-Hwa Lee² and Dong-Yeul Kwon^1,*

¹ Department of Oriental Pharmacy, College of Pharmacy, Wonkwang University, Wonkwang Oriental Medicines Research Institute, Jeonbuk 570-749, Korea

² College of Veterinary Medicine and Bio-Safety Research Institute, Chonbuk National University, Jeonju, 561-756, Korea

Molecules 2010, 15(1), 385-398; https://doi.org/10.3390/molecules15010385 - 18 Jan 2010

Cited by 128 | Viewed by 16450

Abstract

Luteolin (3′,4′,5,7-tetrahydroxylflavone) is a plant flavonoid and pharmacologically active agent that has been isolated from several plant species. In the present study, the effect of luteolin from the flowers of Lonicera japonica on phorbol 12-myristate 13-acetate (PMA) plus A23187-induced mast cell activation was [...] Read more.

Luteolin (3′,4′,5,7-tetrahydroxylflavone) is a plant flavonoid and pharmacologically active agent that has been isolated from several plant species. In the present study, the effect of luteolin from the flowers of Lonicera japonica on phorbol 12-myristate 13-acetate (PMA) plus A23187-induced mast cell activation was examined. Luteolin significantly inhibited the induction of inflammatory cytokines such as tumor necrosis factor (TNF)-α, interleukin (IL)-8, IL-6 and granulocyte-macrophage colony-stimulating factor (GM-CSF) by PMA plus A23187. Moreover, luteolin attenuated cyclooxygenase (COX)-2 expression and intracellular Ca²⁺ levels. In activated HMC-1 cells, the phosphorylation of extra-signal response kinase (ERK 1/2) and c-jun N-terminal Kinase (JNK 1/2), but not p38 mitogen-activated protein kinase (p38 MAPK) were decreased by treatment of the cells with luteolin. Luteolin inhibited PMA plus A23187-induced nuclear factor (NF)-κB activation, IκB degradation, and luciferase activity. Furthermore, luteolin suppressed the expression of TNF-α, IL-8, IL-6, GM-CSF, and COX-2 through a decrease in the intracellular Ca²⁺ levels, and also showed a suppression of the ERK 1/2, JNK 1/2, and NF-κB activation. These results indicated that luteolin from the flowers of Lonicera japonica exerted a regulatory effect on mast cell-mediated inflammatory diseases, such as RA, allergy disease and IBD. Full article

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8 pages, 422 KB

Open AccessArticle

Isolation, Synthesis and Structures of Ginsenoside Derivatives and Their Anti-Tumor Bioactivity

by Mei Han^1,†, Jin-Gang Hou^1,†, Cheng-Ming Dong^2,*, Wei Li^1,3, Hao-Lun Yu¹, Yi-Nan Zheng^1,* and Li Chen³

¹ College of Chinese Medicinal Materials, Jilin Agricultural University, Changchun 130118, China

² Department of Pharmaceutical Science, Henan College of Traditional Chinese Medicine, Zhengzhou 450008, China

³ Norman Bethune College of Medicine, Jilin University, Changchun, 130000, China

^† These authors contributed equally to this work.

Molecules 2010, 15(1), 399-406; https://doi.org/10.3390/molecules15010399 - 19 Jan 2010

Cited by 20 | Viewed by 11161

Abstract

Protopanaxatriol saponins obtained with AB-8 macroporous resin mainly consisted of ginsenosides Rg₁ and Re. A novel mono-ester of ginsenoside-Rh₁ (ginsenoside-ORh₁) was synthesized through further enzymatic hydrolysis and octanoyl chloride modifications. A 53% yield was obtained by a facile synthetic [...] Read more.

Protopanaxatriol saponins obtained with AB-8 macroporous resin mainly consisted of ginsenosides Rg₁ and Re. A novel mono-ester of ginsenoside-Rh₁ (ginsenoside-ORh₁) was synthesized through further enzymatic hydrolysis and octanoyl chloride modifications. A 53% yield was obtained by a facile synthetic method. The structures were identified on the basis of 1D-NMR and 2D-NMR, as well as ESI-TOF-MS mass spectroscopic analyses. The isolated and synthetic compounds were applied in an anti-tumor bioassay, in which ginsenoside ORh₁ showed moderate effects on Murine H22 Hepatoma Cells. Full article

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13 pages, 174 KB

Open AccessArticle

Gas-Phase Pyrolytic Reaction of 4-Aryl-3-buten-2-ols and Allyl Benzyl Ethers: Kinetic and Mechanistic Study

by Alya M. Al-Etaibi¹, Nouria A. Al-Awadi^2,*, Maher R. Ibrahim² and Yehia A. Ibrahim²

¹ Natural Science Department, College of Health Science, Public Authority for Applied Education and Training, Kuwait

² Chemistry Department, Kuwait University, P.O. Box 5969, Safat 13060, Kuwait

Molecules 2010, 15(1), 407-419; https://doi.org/10.3390/molecules15010407 - 20 Jan 2010

Cited by 3 | Viewed by 14238

Abstract

Flash vacuum pyrolysis (FVP) of 4-aryl-3-buten-2-ols [ArCH=CH-CH(CH₃)OH, where Ar is phenyl, p-MeO, p-Me, p-Cl, p-NO₂] gave the corresponding buta-1,3-dien-1-ylbenzene (ArCH=CH-CH=CH₂, where Ar is Ph, p-MeO, p-Me, p-Cl, p-NO₂ [...] Read more.

Flash vacuum pyrolysis (FVP) of 4-aryl-3-buten-2-ols [ArCH=CH-CH(CH₃)OH, where Ar is phenyl, p-MeO, p-Me, p-Cl, p-NO₂] gave the corresponding buta-1,3-dien-1-ylbenzene (ArCH=CH-CH=CH₂, where Ar is Ph, p-MeO, p-Me, p-Cl, p-NO₂) and 7-X-1,2-dihydronaphthalene derivatives (where X is H, MeO); FVP of 1-aryl-3-benzyloxy1-1-butenes and benzyl cinnamyl ethers [ArCH=CHCH(X)OCH₂Ph, where Ar is phenyl, p-MeO, p-Me, p-Cl, X is H, Me, Ph] gave the corresponding but-2-en-1-ylbenzene derivatives (ArCH₂CH=CH-X, where X is H, Me, Ph) together with benzaldehyde. The proposed mechanism of these pyrolytic transformations was supported by kinetic and product analysis. Full article

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12 pages, 305 KB

Open AccessArticle

Condensed Tannins from Mangrove Species Kandelia candel and Rhizophora mangle and Their Antioxidant Activity

by Liang-Liang Zhang^1,2, Yi-Ming Lin^1,*, Hai-Chao Zhou¹, Shu-Dong Wei¹ and Jia-Hong Chen²

¹ Key Laboratory of the Ministry of Education for Coastal and Wetland Ecosystems, School of Life Sciences, Xiamen University, Xiamen 361005, China

² Key and Open Lab. on Forest Chemical Engineering SFA, Institute of Chemical Industry of Forest Products, CAF; Nanjing 210042, China

Molecules 2010, 15(1), 420-431; https://doi.org/10.3390/molecules15010420 - 20 Jan 2010

Cited by 102 | Viewed by 17136

Abstract

The structures of condensed tannins isolated from two mangrove species, Kandelia candel and Rhizophora mangle, were characterized by 13C nuclear magnetic resonance (NMR) spectroscopy and matrix assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS) analyses. Results demonstrate that large heterogeneity occurs in [...] Read more.

The structures of condensed tannins isolated from two mangrove species, Kandelia candel and Rhizophora mangle, were characterized by 13C nuclear magnetic resonance (NMR) spectroscopy and matrix assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS) analyses. Results demonstrate that large heterogeneity occurs in degree of polymerization, pattern of hydroxylation, and substitution with monosaccharides in the structures of the condensed tannins. Condensed tannin oligomers from K. candel and R. mangle were shown to be heterogeneous mixtures consisting of procyanidin and prodelphinidin structural units with the former dominating. The MALDI-TOF mass spectra contained masses corresponding to a distinct oligomeric series of glycosylated heteropolyﬂavan units. In addition, condensed tannins from two mangrove plants were screened for their potential antioxidant activities using 1,1-diphenyl-2-picrylhydrazyl (DPPH) and ferric reducing antioxidant power (FRAP) model systems. Full article

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10 pages, 125 KB

Open AccessArticle

In Vitro and in Vivo Effects of Three Different Mitragyna speciosa Korth Leaf Extracts on Phase II Drug Metabolizing Enzymes—Glutathione Transferases (GSTs)

by Juzaili Azizi¹, Sabariah Ismail^1,*, Mohd Nizam Mordi¹, Surash Ramanathan¹, Mohd Ikram Mohd Said² and Sharif Mahsufi Mansor¹

¹ Centre for Drug Research, Universiti Sains Malaysia, 11800 USM Penang, Malaysia

² School of Chemical Sciences and Food Technology, Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor, Malaysia

Molecules 2010, 15(1), 432-441; https://doi.org/10.3390/molecules15010432 - 20 Jan 2010

Cited by 55 | Viewed by 14060

Abstract

In the present study, we investigate the effects of three different Mitragyna speciosa extracts, namely methanolic, aqueous and total alkaloid extracts, on glutathione transferase-specific activity in male Sprague Dawley rat liver cytosol in vitro and in vivo. In the in vitro study, [...] Read more.

In the present study, we investigate the effects of three different Mitragyna speciosa extracts, namely methanolic, aqueous and total alkaloid extracts, on glutathione transferase-specific activity in male Sprague Dawley rat liver cytosol in vitro and in vivo. In the in vitro study, the effect of Mitragyna speciosa extracts (0.01 to 750 µg/mL) against the specific activity of glutathione transferases was examined in rat liver cytosolic fraction from untreated rats. Our data show concentration dependent inhibition of cytosolic GSTs when Mitragyna speciosa extract was added into the reaction mixture. At the highest concentration used, the methanolic extract showed the highest GSTs specific activity inhibition (61%), followed by aqueous (50%) and total alkaloid extract (43%), respectively. In in vivo study, three different dosages; 50, 100 and 200 mg/kg for methanolic and aqueous extracts and 5, 10 and 20 mg/kg for total alkaloid extract were given orally for 14 days. An increase in GST specific activity was generally observed. However, only Mitragyna speciosa aqueous extract with a dosage of 100 mg/kg showed significant results: 129% compared to control. Full article

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18 pages, 634 KB

Open AccessReview

Vitamin B₆: A Molecule for Human Health?

by Hanjo Hellmann^* and Sutton Mooney

Washington State University, Abelson 435, P.O. Box 66224, Pullman, WA, USA

Molecules 2010, 15(1), 442-459; https://doi.org/10.3390/molecules15010442 - 20 Jan 2010

Cited by 222 | Viewed by 38807

Abstract

Vitamin B₆ is an intriguing molecule that is involved in a wide range of metabolic, physiological and developmental processes. Based on its water solubility and high reactivity when phosphorylated, it is a suitable co-factor for many biochemical processes. Furthermore the vitamin is [...] Read more.

Vitamin B₆ is an intriguing molecule that is involved in a wide range of metabolic, physiological and developmental processes. Based on its water solubility and high reactivity when phosphorylated, it is a suitable co-factor for many biochemical processes. Furthermore the vitamin is a potent antioxidant, rivaling carotenoids or tocopherols in its ability to quench reactive oxygen species. It is therefore not surprising that the vitamin is essential and unquestionably important for the cellular metabolism and well-being of all living organisms. The review briefly summarizes the biosynthetic pathways of vitamin B₆ in pro- and eukaryotes and its diverse roles in enzymatic reactions. Finally, because in recent years the vitamin has often been considered beneficial for human health, the review will also sum up and critically reflect on current knowledge how human health can profit from vitamin B₆. Full article

(This article belongs to the Special Issue Vitamins)

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42 pages, 2057 KB

Open AccessReview

Total Synthesis of Annonaceous Acetogenins Belonging to the Non-Adjacent Bis-THF and Non-Adjacent THF-THP Sub-Classes

by Ian B. Spurr and Richard C. D. Brown^*

The School of Chemistry, The University of Southampton, Highfield, Southampton SO17 1BJ, UK

Molecules 2010, 15(1), 460-501; https://doi.org/10.3390/molecules15010460 - 21 Jan 2010

Cited by 35 | Viewed by 15558

Abstract

The synthesis of the subgroups of acetogenins containing non-adjacent bis-THF and non-adjacent THF-THP core units is reviewed. Specifically, total syntheses of gigantecin, 4-deoxygigantecin, cis-sylvaticin, squamostatin-C, squamostatin-D, sylvaticin and mucocin are discussed. Full article

(This article belongs to the Special Issue Acetogenins: Extraction, Synthesis and Biological Properties)

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13 pages, 133 KB

Open AccessArticle

Synthesis and Antimicrobial Activity of New 5-(2-Thienyl)-1,2,4-triazoles and 5-(2-Thienyl)-1,3,4-oxadiazoles and Related Derivatives

by Mohamed A. Al-Omar

Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia

Molecules 2010, 15(1), 502-514; https://doi.org/10.3390/molecules15010502 - 22 Jan 2010

Cited by 49 | Viewed by 12559

Abstract

New 5-(2-thienyl)-1,2,4-triazoles and 5-(2-thienyl)-1,3,4-oxadiazoles namely, N-[3-mercapto-5-(2-thienyl)-1,2,4-triazol-4-yl]-N'-arylthioureas 4a–e, 2-arylamino-5-(2-thienyl)-1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles 5a–e, 3-arylaminomethyl-5-(2-thienyl)-1,3,4-oxadiazoline-2-thiones 7a–e, 3-(N-substituted anilinomethyl)-5-(2-thienyl)-1,3,4-oxadiazoline-2-thiones 8a, b and 3-(4-substituted-1-piperazinylmethyl)-5-(2-thienyl)-1,3,4-oxadiazoline-2-thiones 9a–f, were prepared. The synthesized compounds were tested for in vitro activities against certain strains [...] Read more.

New 5-(2-thienyl)-1,2,4-triazoles and 5-(2-thienyl)-1,3,4-oxadiazoles namely, N-[3-mercapto-5-(2-thienyl)-1,2,4-triazol-4-yl]-N'-arylthioureas 4a–e, 2-arylamino-5-(2-thienyl)-1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles 5a–e, 3-arylaminomethyl-5-(2-thienyl)-1,3,4-oxadiazoline-2-thiones 7a–e, 3-(N-substituted anilinomethyl)-5-(2-thienyl)-1,3,4-oxadiazoline-2-thiones 8a, b and 3-(4-substituted-1-piperazinylmethyl)-5-(2-thienyl)-1,3,4-oxadiazoline-2-thiones 9a–f, were prepared. The synthesized compounds were tested for in vitro activities against certain strains of Gram-positive and Gram-negative bacteria and the yeast-like pathogenic fungus Candida albicans. Compound 9a displayed marked broad spectrum antibacterial activity, while compounds 4d, 5e, 7b, 7c, 7d, 9b, 9c and 9d were highly active against the tested Gram-positive bacteria. None of the synthesized compounds were proved to be significantly active against Candida albicans. Full article

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17 pages, 461 KB

Open AccessArticle

Synthesis of Some New Mono- and Bis-Polycyclic Aromatic Spiro and Bis-Nonspiro-β-Lactams

by Aliasghar Jarrahpour^* and Edris Ebrahimi

Department of Chemistry, College of Sciences, Shiraz University, Shiraz, 71454, Iran

Molecules 2010, 15(1), 515-531; https://doi.org/10.3390/molecules15010515 - 22 Jan 2010

Cited by 22 | Viewed by 10845

Abstract

Some new mono-and bis-polycyclic aromatic spiro-β-lactams and bis-non spiro-polycyclic aromatic β-lactams have been synthesized from imines derived from anthracene-9-carbaldehyde, 2-naphtaldehyde and a ketene derived from 9H-xanthene-9-carboxylic acid and phenoxyacetic acid by a [2+2] cycloaddition reaction. The cycloadducts were characterized by spectral data, including [...] Read more.

Some new mono-and bis-polycyclic aromatic spiro-β-lactams and bis-non spiro-polycyclic aromatic β-lactams have been synthesized from imines derived from anthracene-9-carbaldehyde, 2-naphtaldehyde and a ketene derived from 9H-xanthene-9-carboxylic acid and phenoxyacetic acid by a [2+2] cycloaddition reaction. The cycloadducts were characterized by spectral data, including ¹H-NMR, ¹³C-NMR, IR and elemental analyses. The configurations of some of these mono-spiro-β-lactams were established by X-ray crystal analysis. Full article

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13 pages, 212 KB

Open AccessArticle

Catalytic Asymmetric 1,4-Additions of β-Keto Esters to Nitroalkenes Promoted by a Bifunctional Homobimetallic Co₂-Schiff Base Complex

by Makoto Furutachi, Zhihua Chen, Shigeki Matsunaga^* and Masakatsu Shibasaki^*

Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan

Molecules 2010, 15(1), 532-544; https://doi.org/10.3390/molecules15010532 - 22 Jan 2010

Cited by 33 | Viewed by 10310

Abstract

Catalytic asymmetric 1,4-addition of β-keto esters to nitroalkenes is described. 2.5 mol % of a homobimetallic Lewis acid/Brønsted base bifunctional Co₂-Schiff base complex smoothly promoted the reaction in excellent yield (up to 99%), diastereoselectivity, and enantioselectivity (up to >30:1 dr and [...] Read more.

Catalytic asymmetric 1,4-addition of β-keto esters to nitroalkenes is described. 2.5 mol % of a homobimetallic Lewis acid/Brønsted base bifunctional Co₂-Schiff base complex smoothly promoted the reaction in excellent yield (up to 99%), diastereoselectivity, and enantioselectivity (up to >30:1 dr and 98% ee). Catalyst loading was successfully reduced to 0.1 mol %. Mechanistic studies suggested that intramolecular cooperative functions of the two Co-metal centers are important for high catalytic activity and stereoselectivity. Full article

(This article belongs to the Special Issue Bifunctional Catalysis)

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9 pages, 536 KB

Open AccessArticle

Antiproliferative Effect and Ultrastructural Alterations Induced by Psilostachyin on Trypanosoma cruzi

by Valeria Sülsen^1,†, Patricia Barrera^2,†, Liliana Muschietti^1,*, Virginia Martino¹ and Miguel Sosa²

¹ Cátedra de Farmacognosia, Universidad de Buenos Aires, Facultad de Farmacia y Bioquímica, IQUIMEFA (UBA-CONICET), Junín 956 (1113), CABA, Argentina

² Facultad de Ciencias Médicas, Instituto de Histología y Embriología "Dr. Mario H. Burgos", Universidad Nacional de Cuyo-CONICET, CC 56 (5500), Mendoza, Argentina

^† These authors contributed equally to this work.

Molecules 2010, 15(1), 545-553; https://doi.org/10.3390/molecules15010545 - 25 Jan 2010

Cited by 28 | Viewed by 9865

Abstract

The effect of psilostachyin, a natural sesquiterpene lactone, on the growth and viability of cultured epimastigotes of Trypanosoma cruzi (Tulahuen) is reported. The antiproliferative effect was evaluated by counting the parasites in a Neubauer chamber and measuring their viability by using the dye [...] Read more.

The effect of psilostachyin, a natural sesquiterpene lactone, on the growth and viability of cultured epimastigotes of Trypanosoma cruzi (Tulahuen) is reported. The antiproliferative effect was evaluated by counting the parasites in a Neubauer chamber and measuring their viability by using the dye exclusion technique. The effect on parasite growth was irreversible at concentrations higher than 1.0 µg/mL and the addition of glutathione only partially blocked the effect of the compound. Moreover, we have studied the effects of this natural compound on parasite ultrastructure by transmission electron microscopy. Interestingly, psilostachyin induced ultrastructural alterations on the parasites at a concentration of 0.5 µg/mL, with important mitochondrial swelling and deformity of the kinetoplast. Full article

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16 pages, 2091 KB

Open AccessArticle

Structure, Morphology and Optical Properties of Chiral N-(4-X-phenyl)-N-[1(S)-1-phenylethyl]thiourea, X= Cl, Br, and NO₂

by Werner Kaminsky^*, Donald Responte, Dan Daranciang, Jose B. Gallegos, Bao-Chau Ngoc Tran and Tram-Anh Pham

Department of Chemistry, University of Washington, Seattle, Washington 98195, USA

Molecules 2010, 15(1), 554-569; https://doi.org/10.3390/molecules15010554 - 26 Jan 2010

Cited by 9 | Viewed by 11685

Abstract

Three new enantiopure aryl-thioureas have been synthesized, N-(4-X-phenyl)-N-[1(S)-1-phenylethyl]thiourea, X= Cl, Br, and NO₂ (compounds 1-3, respectively). Large single crystals of up to 0.5 cm³ were grown from methanol/ethanol solutions. Molecular structures were derived from X-ray [...] Read more.

Three new enantiopure aryl-thioureas have been synthesized, N-(4-X-phenyl)-N-[1(S)-1-phenylethyl]thiourea, X= Cl, Br, and NO₂ (compounds 1-3, respectively). Large single crystals of up to 0.5 cm³ were grown from methanol/ethanol solutions. Molecular structures were derived from X-ray diffraction studies and the crystal morphology was compared to calculations employing the Bravais-Friedel, Donnay-Harker model. Molecular packing was further studied with Hirshfeld surface calculations. Semi-empirical classical model calculations of refractive indices, optical rotation and the electro-optic effect were performed with OPTACT on the basis of experimentally determined refractive indices. Compound 3 (space group P 1 (No. 1)) was estimated to possess a large electro-optic coefficient r₃₃₃ of approximately 30 pm/V, whereas 1 and 2 (space Group P 2₁ (No. 4) exhibit much smaller effects. Full article

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34 pages, 3063 KB

Open AccessReview

Photoresponsive Block Copolymers Containing Azobenzenes and Other Chromophores

by Haifeng Yu^1,* and Takaomi Kobayashi²

¹ Top Runner Incubation Center for Academia-Industry Fusion, Nagaoka University of Technology, 1603-1 Kamitomioka, Nagaoka 940-2188, Japan

² Department of Materials Science and Technology, Nagaoka University of Technology, 1603-1 Kamitomioka, Nagaoka 940-2188, Japan

Molecules 2010, 15(1), 570-603; https://doi.org/10.3390/molecules15010570 - 26 Jan 2010

Cited by 76 | Viewed by 15674

Abstract

Photoresponsive block copolymers (PRBCs) containing azobenzenes and other chromophores can be easily prepared by controlled polymerization. Their photoresponsive behaviors are generally based on photoisomerization, photocrosslinking, photoalignment and photoinduced cooperative motions. When the photoactive block forms mesogenic phases upon microphase separation of PRBCs, supramolecular [...] Read more.

Photoresponsive block copolymers (PRBCs) containing azobenzenes and other chromophores can be easily prepared by controlled polymerization. Their photoresponsive behaviors are generally based on photoisomerization, photocrosslinking, photoalignment and photoinduced cooperative motions. When the photoactive block forms mesogenic phases upon microphase separation of PRBCs, supramolecular cooperative motion in liquid-crystalline PRBCs enables them to self-organize into hierarchical structures with photoresponsive features. This offers novel opportunities to photocontrol microphase-separated nanostructures of well-defined PRBCs and extends their diverse applications in holograms, nanotemplates, photodeformed devices and microporous films. Full article

(This article belongs to the Special Issue Photochemistry in Organic Synthesis)

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Molecules, Volume 15, Issue 1 (January 2010) – 47 articles , Pages 1-605

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