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Molecules, Volume 15, Issue 3 (March 2010), Pages 1097-2059

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Open AccessArticle Cationic Heteroleptic Cyclometalated IridiumIII Complexes Containing Phenyl-Triazole and Triazole-Pyridine Clicked Ligands
Molecules 2010, 15(3), 2039-2059; https://doi.org/10.3390/molecules15032039
Received: 8 February 2010 / Revised: 8 March 2010 / Accepted: 18 March 2010 / Published: 23 March 2010
Cited by 59 | PDF Full-text (815 KB) | Supplementary Files
Abstract
Novel heteroleptic iridium complexes containing the 1-substituted-4-phenyl-1H-1,2,3-triazole (phtl) cyclometalating ligand have been synthesized. The 3+2 Huisgen dipolar cycloaddition method (‘click’ chemistry) was utilized to prepare a class of bidentate ligands (phtl) bearing different substituents on the triazole moiety. By using various
[...] Read more.
Novel heteroleptic iridium complexes containing the 1-substituted-4-phenyl-1H-1,2,3-triazole (phtl) cyclometalating ligand have been synthesized. The 3+2 Huisgen dipolar cycloaddition method (‘click’ chemistry) was utilized to prepare a class of bidentate ligands (phtl) bearing different substituents on the triazole moiety. By using various ligands (phtl-R1 and pytl-R2) (R1=adamantane, methyl and R2=adamantane, methyl, β-cyclodextrin, ursodeoxycholic acid), we prepared a small library of new luminescent ionic iridium complexes [Ir(phtr-R1)2(pytl-R2)]Cl and report on their photophysical properties. The flexibility of the clicking approach allows a straightforward control on the chemical-physical properties of the complexes by varying the nature of the substituent on the ligand. Full article
(This article belongs to the Special Issue Click Chemistry)
Open AccessArticle Acetamide Derivatives with Antioxidant Activity and Potential Anti-Inflammatory Activity
Molecules 2010, 15(3), 2028-2038; https://doi.org/10.3390/molecules15032028
Received: 2 February 2010 / Revised: 9 March 2010 / Accepted: 18 March 2010 / Published: 23 March 2010
Cited by 30 | PDF Full-text (235 KB)
Abstract
This study reports the synthesis and antioxidant activity of some new acetamide derivatives. The compounds’ structures were elucidated by NMR analysis and their melting points were measured. The in vitro antioxidant activity of these compounds was tested by evaluating the amount of scavenged
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This study reports the synthesis and antioxidant activity of some new acetamide derivatives. The compounds’ structures were elucidated by NMR analysis and their melting points were measured. The in vitro antioxidant activity of these compounds was tested by evaluating the amount of scavenged ABTS radical and estimating ROS and NO production in tBOH- or LPS-stimulated J774.A1 macrophages. All compounds were tested for their effect on cell viability by an MTT assay and by a Brine Shrimp Test. Full article
Open AccessArticle Antioxidant Capacities and Phenolic Levels of Different Varieties of Serbian White Wines
Molecules 2010, 15(3), 2016-2027; https://doi.org/10.3390/molecules15032016
Received: 22 January 2010 / Revised: 23 February 2010 / Accepted: 9 March 2010 / Published: 22 March 2010
Cited by 27 | PDF Full-text (376 KB)
Abstract
The biologically active compounds in wine, especially phenolics, are responsible for reduced risk of developing chronic diseases (cardiovascular disrease, cancer, diabetes, etc.), due to their antioxidant activities. We determined the contents of total phenolics (TP) and total flavonoids (TF) in selected Serbian
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The biologically active compounds in wine, especially phenolics, are responsible for reduced risk of developing chronic diseases (cardiovascular disrease, cancer, diabetes, etc.), due to their antioxidant activities. We determined the contents of total phenolics (TP) and total flavonoids (TF) in selected Serbian white wines by colorimetric methods. Total antioxidant activity (TAA) of the white wines was analyzed using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging capacity assay. Međaš beli had the highest content of TP, TF and TAA. The radical scavenging capacity (RSC) and total antioxidant activity (TAA) of white wines were 15.30% and 1.055 mM Trolox equivalent, respectively. Total phenolic (TP) and total flavonoid (TF) contents in white wines ranged from 238.3 to 420.6 mg gallic acid equivalent per L of wines and 42.64 to 81.32 mg catechin equivalent per L of wines, respectively. A high and significant correlation between antioxidant activity and total phenolic content was determined in wines (R2 = 0.968, p < 0.01). For the individual polyphenols determination we used a high performance liquid chromatography (HPLC)-diode array detection (DAD) technique. The majority of white wine polyphenols was represent by four hydroxycinnamic acids (HCAs). Full article
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Open AccessArticle The Combination of TRAIL and Isoflavones Enhances Apoptosis in Cancer Cells
Molecules 2010, 15(3), 2000-2015; https://doi.org/10.3390/molecules15032000
Received: 4 February 2010 / Revised: 9 March 2010 / Accepted: 19 March 2010 / Published: 22 March 2010
Cited by 32 | PDF Full-text (204 KB)
Abstract
Isoflavones are a class of bioactive polyphenols with cancer chemopreventive properties. TRAIL (tumor necrosis factor-related apoptosis-inducing ligand) is a naturally occurring antitumor agent that selectively induces programmed death (apoptosis) in cancer cells. Polyphenols can modulate TRAIL-mediated apoptosis in cancer cells. We examined the
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Isoflavones are a class of bioactive polyphenols with cancer chemopreventive properties. TRAIL (tumor necrosis factor-related apoptosis-inducing ligand) is a naturally occurring antitumor agent that selectively induces programmed death (apoptosis) in cancer cells. Polyphenols can modulate TRAIL-mediated apoptosis in cancer cells. We examined the cytotoxic and apoptotic activities of isoflavones in combination with TRAIL on HeLa cancer cells. The apoptosis was detected by fluorescence microscopy with annexin V-FITC. The cytotoxicity was evaluated by MTT and LDH assays. The tested isoflavones: genistein, biochanin-A and neobavaisoflavone enhance TRAIL-induced apoptosis in HeLa cells. Our study indicated that isoflavones augmented TRAIL-cytotoxicity against cancer cells and confirmed potential role of those polyphenols in chemoprevention. Full article
Open AccessReview QSAR Models for Reproductive Toxicity and Endocrine Disruption Activity
Molecules 2010, 15(3), 1987-1999; https://doi.org/10.3390/molecules15031987
Received: 21 December 2009 / Revised: 29 January 2010 / Accepted: 19 March 2010 / Published: 22 March 2010
Cited by 21 | PDF Full-text (285 KB)
Abstract
Reproductive toxicity is an important regulatory endpoint, which is required in registration procedures of chemicals used for different purposes (for example pesticides). The in vivo tests are expensive, time consuming and require large numbers of animals, which must be sacrificed. Therefore an effort
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Reproductive toxicity is an important regulatory endpoint, which is required in registration procedures of chemicals used for different purposes (for example pesticides). The in vivo tests are expensive, time consuming and require large numbers of animals, which must be sacrificed. Therefore an effort is ongoing to develop alternative In vitro and in silico methods to evaluate reproductive toxicity. In this review we describe some modeling approaches. In the first example we describe the CAESAR model for prediction of reproductive toxicity; the second example shows a classification model for endocrine disruption potential based on counter propagation artificial neural networks; the third example shows a modeling of relative binding affinity to rat estrogen receptor, and the fourth one shows a receptor dependent modeling experiment. Full article
(This article belongs to the Special Issue Molecular Diversity Feature Papers)
Open AccessAddendum Addendum: De Sousa Luis, J.A., et al. Synthesis of New Imidazolidin-2,4-dione and 2-Thioxo-imidazolidin-4-ones via C-Phenylglycine Derivatives. Molecules 2010, 15, 128-137
Molecules 2010, 15(3), 1985-1986; https://doi.org/10.3390/molecules15031985
Received: 12 February 2010 / Published: 22 March 2010
PDF Full-text (26 KB)
Abstract
The authors wish to make the following correction to their paper [1], published recently in Molecules. The coauthor RalineMendonça dos Anjos was omitted from the author list, which should read as follows: [...] Full article
Open AccessArticle Conjugate Addition of Nucleophiles to the Vinyl Function of 2-Chloro-4-vinylpyrimidine Derivatives
Molecules 2010, 15(3), 1973-1984; https://doi.org/10.3390/molecules15031973
Received: 2 March 2010 / Revised: 9 March 2010 / Accepted: 18 March 2010 / Published: 19 March 2010
Cited by 5 | PDF Full-text (171 KB)
Abstract
Conjugate addition reaction of various nucleophiles across the vinyl group of 2-chloro-4-vinylpyrimidine, 2-chloro-4-(1-phenylvinyl)pyrimidine and 2-chloro-4-vinylquinazoline provides the corresponding 2-chloro-4-(2-substituted ethyl)pyrimidines and 2-chloro-4-(2-substituted ethyl)quinazolines. Treatment of these products, without isolation, with N-methylpiperazine results in nucleophilic displacement of chloride and yields the corresponding 2,4-disubstituted
[...] Read more.
Conjugate addition reaction of various nucleophiles across the vinyl group of 2-chloro-4-vinylpyrimidine, 2-chloro-4-(1-phenylvinyl)pyrimidine and 2-chloro-4-vinylquinazoline provides the corresponding 2-chloro-4-(2-substituted ethyl)pyrimidines and 2-chloro-4-(2-substituted ethyl)quinazolines. Treatment of these products, without isolation, with N-methylpiperazine results in nucleophilic displacement of chloride and yields the corresponding 2,4-disubstituted pyrimidines and quinazolines. Full article
Open AccessCommunication Preparation of the Pyridinium Salts Differing in the Length of the N-Alkyl Substituent
Molecules 2010, 15(3), 1967-1972; https://doi.org/10.3390/molecules15031967
Received: 14 December 2009 / Revised: 4 March 2010 / Accepted: 10 March 2010 / Published: 19 March 2010
Cited by 16 | PDF Full-text (99 KB)
Abstract
Quaternary pyridinium salts with chains ranging from C8 to C20 belong in the large group of cationic surfactants. In this paper, the preparation of such cationic surface active agents based on the pyridinium moiety and differing in the length of the
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Quaternary pyridinium salts with chains ranging from C8 to C20 belong in the large group of cationic surfactants. In this paper, the preparation of such cationic surface active agents based on the pyridinium moiety and differing in the length of the N-alkyl chain is described. Additionally, HPLC technique was established to distinguish each prepared pyridinium analogue. This study represents universal method for preparation and identification of quaternary pyridinium detergents. Full article
Open AccessArticle New Cytotoxic Azaphilones from Monascus purpureus-Fermented Rice (Red Yeast Rice)
Molecules 2010, 15(3), 1958-1966; https://doi.org/10.3390/molecules15031958
Received: 18 January 2010 / Revised: 1 March 2010 / Accepted: 8 March 2010 / Published: 18 March 2010
Cited by 23 | PDF Full-text (157 KB) | Supplementary Files
Abstract
Using a cell-based cytotoxicity assay three new cytotoxic azaphilones, including two stereoisomers and designated monapurones A-C (1-3), were isolated from the extract of Monascus purpureus-fermented rice (red yeast rice). Their structures were elucidated by detailed interpretation of spectroscopic and
[...] Read more.
Using a cell-based cytotoxicity assay three new cytotoxic azaphilones, including two stereoisomers and designated monapurones A-C (1-3), were isolated from the extract of Monascus purpureus-fermented rice (red yeast rice). Their structures were elucidated by detailed interpretation of spectroscopic and chemical data. The relative configurations were assigned on the basis of analysis of NOE data, and the absolute configurations were determined by direct comparison of their CD spectra with those of known azaphilones and chemical correlations. In the in vitro assays, monapurones A-C (1-3) showed selective cytotoxicity against human cancer cell line A549 with IC50 values of 3.8, 2.8 and 2.4mM respectively, while exhibiting no significant toxicity to normal MRC-5 and WI-38 cells at the same concentration. Full article
Open AccessReview Biomimetic Silica Microspheres in Biosensing
Molecules 2010, 15(3), 1932-1957; https://doi.org/10.3390/molecules15031932
Received: 3 February 2010 / Revised: 16 March 2010 / Accepted: 17 March 2010 / Published: 17 March 2010
Cited by 17 | PDF Full-text (988 KB)
Abstract
Lipid vesicles spontaneously fuse and assemble into a lipid bilayer on planar or spherical silica surfaces and other substrates. The supported lipid bilayers (SLBs) maintain characteristics of biological membranes, and are thus considered to be biomembrane mimetic systems that are stable because of
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Lipid vesicles spontaneously fuse and assemble into a lipid bilayer on planar or spherical silica surfaces and other substrates. The supported lipid bilayers (SLBs) maintain characteristics of biological membranes, and are thus considered to be biomembrane mimetic systems that are stable because of the underlying substrate. Examples of their shared characteristics with biomembranes include lateral fluidity, barrier formation to ions and molecules, and their ability to incorporate membrane proteins into them. Biomimetic silica microspheres consisting of SLBs on solid or porous silica microspheres have been utilized for different biosensing applications. The advantages of such biomimetic microspheres for biosensing include their increased surface area to volume ratio which improves the detection limits of analytes, and their amenability for miniaturization, multiplexing and high throughput screening. This review presents examples and formats of using such biomimetic solid or porous silica microspheres in biosensing. Full article
(This article belongs to the Special Issue Phospholipids)
Open AccessArticle Enhanced Reactivity of [Hydroxy(tosyloxy)iodo]benzene in Fluoroalcohol Media. Efficient Direct Synthesis of Thienyl(aryl)iodonium Salts
Molecules 2010, 15(3), 1918-1931; https://doi.org/10.3390/molecules15031918
Received: 3 February 2010 / Revised: 15 March 2010 / Accepted: 16 March 2010 / Published: 17 March 2010
Cited by 28 | PDF Full-text (121 KB)
Abstract
In this manuscript, we report clear evidence for the generation of aromatic cation radicals produced by using [hydroxy(tosyloxy)iodo]benzene (HTIB) in fluoroalcohol solvents such as 2,2,2-trifluoroethanol (TFE) and 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP). The single-electron-transfer (SET) oxidation ability of HTIB to give cation radicals was first established
[...] Read more.
In this manuscript, we report clear evidence for the generation of aromatic cation radicals produced by using [hydroxy(tosyloxy)iodo]benzene (HTIB) in fluoroalcohol solvents such as 2,2,2-trifluoroethanol (TFE) and 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP). The single-electron-transfer (SET) oxidation ability of HTIB to give cation radicals was first established by ESR and UV measurements. The reaction was broadly applied to various thiophenes, and unique thienyliodonium salts were directly synthesized by this method in excellent yields without the production of any harmful byproducts. Full article
(This article belongs to the Special Issue Advances in Heterocyclic Chemistry)
Open AccessArticle Design, Synthesis and Anti-HIV Integrase Evaluation of N-(5-Chloro-8-Hydroxy-2-Styrylquinolin-7-yl)Benzenesulfonamide Derivatives
Molecules 2010, 15(3), 1903-1917; https://doi.org/10.3390/molecules15031903
Received: 21 October 2009 / Revised: 8 December 2009 / Accepted: 14 December 2009 / Published: 16 March 2010
Cited by 11 | PDF Full-text (221 KB)
Abstract
Styrylquinoline derivatives are demonstrated to be HIV-1 integrase inhibitors. On the basis of our previous CoMFA analysis of a series of styrylquinoline derivatives, N-[(2-substituted-styryl)-5-chloro-8-hydroxyquinolin-7-yl]-benzenesulfonamide derivatives were designed and synthesized,and their possible HIV IN inhibitory activity was evaluated. Full article
Open AccessArticle Liquid-Phase Synthesis of Cyanuric Acid from Urea
Molecules 2010, 15(3), 1898-1902; https://doi.org/10.3390/molecules15031898
Received: 30 January 2010 / Revised: 24 February 2010 / Accepted: 8 March 2010 / Published: 16 March 2010
Cited by 6 | PDF Full-text (105 KB)
Abstract
The focus of this paper was to identify a cheaper solvent from among diesel fuel, kerosene, sulfolane or a mixture of sulfolane and cyclohexanol for the preparation of cyanuric acid heterocyclization of urea. To obtain a higher yield, the effects of catalyst (sodium,
[...] Read more.
The focus of this paper was to identify a cheaper solvent from among diesel fuel, kerosene, sulfolane or a mixture of sulfolane and cyclohexanol for the preparation of cyanuric acid heterocyclization of urea. To obtain a higher yield, the effects of catalyst (sodium, ammonium, calcium and zinc salts) and temperature (160 °C to 220 °C) on the trimerization of urea were also carefully studied. We established the optimal reaction conditions and further validated them in our scale-up experiments. Full article
Open AccessCommunication A New Triterpenoid Saponin from Pulsatilla cernua
Molecules 2010, 15(3), 1891-1897; https://doi.org/10.3390/molecules15031891
Received: 1 February 2010 / Revised: 24 February 2010 / Accepted: 9 March 2010 / Published: 16 March 2010
Cited by 9 | PDF Full-text (192 KB)
Abstract
A new triterpenoid saponin was isolated from Pulsatilla cernua, along with eight known triterpenoids and triterpenoid glycosides. The new compound was identified as 3-O-β-D-glucopyranosyl-(1→4)-α-L-arabinopyranosyl-bayogenin-28-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester (1) on the
[...] Read more.
A new triterpenoid saponin was isolated from Pulsatilla cernua, along with eight known triterpenoids and triterpenoid glycosides. The new compound was identified as 3-O-β-D-glucopyranosyl-(1→4)-α-L-arabinopyranosyl-bayogenin-28-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester (1) on the basis of 1D, 2D-NMR techniques, including COSY, HMBC, and HMQC correlations, MS analysis, as well as chemical methods. Full article
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Open AccessArticle Synthesis of Certain Pyrimidine Derivatives as Antimicrobial Agents and Anti-Inflammatory Agents
Molecules 2010, 15(3), 1882-1890; https://doi.org/10.3390/molecules15031882
Received: 11 January 2010 / Revised: 11 March 2010 / Accepted: 12 March 2010 / Published: 15 March 2010
Cited by 37 | PDF Full-text (205 KB)
Abstract
A variety of novel bicyclic and tricyclic pyrimidine derivatives was obtained via reaction of 6-amino-2-thioxo-1H-pyrimidine-4-one (1) with a different reagents. The antimicrobial and anti-inflammatory activities of some of the synthesized compounds were tested. Full article
Open AccessReview Pharmacological Effects of Rutaecarpine as a Cardiovascular Protective Agent
Molecules 2010, 15(3), 1873-1881; https://doi.org/10.3390/molecules15031873
Received: 3 February 2010 / Revised: 1 March 2010 / Accepted: 8 March 2010 / Published: 15 March 2010
Cited by 39 | PDF Full-text (144 KB)
Abstract
Many studies indicate that traditional Chinese herbs are beneficial in the prevention and treatment of cardiovascular diseases. Evodia rutaecarpa (‘Wu-Chu-Yu’)remains the most popular and multi-purpose herb traditionally used in China for treatment of headache, abdominal pain, postpartum hemorrhage, dysentery and amenorrhea. Rutaecarpine is
[...] Read more.
Many studies indicate that traditional Chinese herbs are beneficial in the prevention and treatment of cardiovascular diseases. Evodia rutaecarpa (‘Wu-Chu-Yu’)remains the most popular and multi-purpose herb traditionally used in China for treatment of headache, abdominal pain, postpartum hemorrhage, dysentery and amenorrhea. Rutaecarpine is one of the intriguing indolopyridoquinazoline alkaloids isolated from ‘Wu-Chu-Yu’. Rutaecarpine has been shown to have cardiovascular biological effects such as inotropic and chronotropic, vasorelaxant, anti-platelet aggregation and anti-inflammatory effects. Furthermore, it has been reported that rutaecarpine has beneficial effects on some cardiovascular diseases. This review summarizes data on the cardiovascular pharmacological actions of rutaecarpine the published over the recent years, aiming to provide more evidence supporting its use in the treatment of cardiovascular diseases. Full article
Open AccessReview Synthesis and Use of Stable Isotope Enriched Retinals in the Field of Vitamin A
Molecules 2010, 15(3), 1825-1872; https://doi.org/10.3390/molecules15031825
Received: 15 January 2010 / Revised: 18 February 2010 / Accepted: 2 March 2010 / Published: 15 March 2010
Cited by 5 | PDF Full-text (366 KB)
Abstract
The role of vitamin A and its metabolites in the life processes starting with the historical background and its up to date information is discussed in the introduction. Also the role of 11Z-retinal in vision and retinoic acid in the biological
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The role of vitamin A and its metabolites in the life processes starting with the historical background and its up to date information is discussed in the introduction. Also the role of 11Z-retinal in vision and retinoic acid in the biological processes is elucidated. The essential role of isotopically enriched systems in the progress of vision research, nutrition research etc. is discussed. In part B industrial commercial syntheses of vitamin A by the two leading companies Hoffmann-La Roche (now DSM) and BASF are discussed. The knowledge obtained via these pioneering syntheses has been essential for the further synthetic efforts in vitamin A field by other scientific groups. The rest of the paper is devoted to the synthetic efforts of the Leiden group that gives an access to the preparation of site directed high level isotope enrichment in retinals. First the synthesis of the retinals with deuterium incorporation in the conjugated side chain is reviewed. Then, 13C-labeled retinals are discussed. This is followed by the discussion of a convergent synthetic scheme that allows a rational access to prepare any isotopomer of retinals. The schemes that provide access to prepare any possible isotope enriched chemically modified systems are discussed. Finally, nor-retinals and bridged retinals that give access to a whole (as yet incomplete) library of possible isotopomers are reviewed. Full article
(This article belongs to the Special Issue Vitamins)
Open AccessArticle Antimicrobial, Cytotoxicity and Phytochemical Screening of Jordanian Plants Used in Traditional Medicine
Molecules 2010, 15(3), 1811-1824; https://doi.org/10.3390/molecules15031811
Received: 5 January 2010 / Revised: 7 February 2010 / Accepted: 10 March 2010 / Published: 12 March 2010
Cited by 61 | PDF Full-text (105 KB)
Abstract
Antimicrobial activity and cytotoxicity of fifty one extracts of different parts of 14 plants were studied. Ethanol, methanol, aqueous, butanol, and n-hexane extracts were tested against three Gram negative, two Gram positive bacteria, and two fungi. Cytotoxicity and phytochemical screening were determined
[...] Read more.
Antimicrobial activity and cytotoxicity of fifty one extracts of different parts of 14 plants were studied. Ethanol, methanol, aqueous, butanol, and n-hexane extracts were tested against three Gram negative, two Gram positive bacteria, and two fungi. Cytotoxicity and phytochemical screening were determined using MTT and TLC assays, respectively. Of the fifty one extracts, twenty two showed activities against different microorganisms with MICs ranging from 62.5 to 1000 µg/mL. The highest activity (100% inhibition) was for a butanol extract of Rosa damascena receptacles against Salmonella typhimurium and Bacillus cereus (MIC of 62.5 and 250 µg/mL) respectively. Butanol extract of Narcissus tazetta aerial parts and aqueous extract of Rosa damascena receptacles were both active against Candida albicans (MIC of 125 µg/mL). Methicillin-resistant Staphylococcus aureus was inhibited by butanol, aqueous extracts of Rosa damascena receptacles and butanol extract of Inula viscosa flowers (MIC of 500, 500, and 250 µg/mL) respectively. Rosa damascena receptacles and Verbascum sinaiticum flowers ethanol extract showed lowest cytoxicity against Vero cell line (IC50 of 454.11and 367.11). Most toxic was the ethanol extract of Ononis hirta aerial parts (IC50 72.50 µg/mL). Flavonoids and terpenoids were present in all plants. Ononis hirta and Narcissus tazetta contained alkaloids. The results validate the use of these plants and report for the first time bioactivity of Rosa damascena receptacles and further justifies the use of such screening programs in the quest for new drugs. Full article
Open AccessArticle Synthesis of a Novel Fluorescent Sensor Bearing Dansyl Fluorophores for the Highly Selective Detection of Mercury (II) Ions
Molecules 2010, 15(3), 1798-1810; https://doi.org/10.3390/molecules15031798
Received: 1 February 2010 / Revised: 22 February 2010 / Accepted: 8 March 2010 / Published: 12 March 2010
Cited by 23 | PDF Full-text (477 KB)
Abstract
A new macromolecule possessing two dansyl moieties and based on 2-[4-(2-aminoethylthio)butylthio]ethanamine was prepared as a fluorescent sensor and its mercury sensing properties toward various transition metal, alkali, and alkali earth ions were investigated. The designed compound exhibited pronounced Hg2+-selective ON-OFF type
[...] Read more.
A new macromolecule possessing two dansyl moieties and based on 2-[4-(2-aminoethylthio)butylthio]ethanamine was prepared as a fluorescent sensor and its mercury sensing properties toward various transition metal, alkali, and alkali earth ions were investigated. The designed compound exhibited pronounced Hg2+-selective ON-OFF type fluorescence switching upon binding. The new compoundprovided highly selective sensing to Hg2+ in acetonitrile-water solvent mixtures with a detection limit of 2.49 x 10-7 M or 50 ppb. The molecular modeling results indicated that ions-recognition of the sensor originated from a self assembly process of the reagentand Hg2+ to form a helical wrapping structure with the favorable electrostatic interactions of Hg2+coordinated with sulfur, oxygen, nitrogen atoms and aromatic moieties. Full article
(This article belongs to the Special Issue Macromolecules: Chemistry, Medicinal and Functional Materials)
Open AccessArticle Synthesis and Characterization of Organotin Containing Copolymers: Reactivity Ratio Studies
Molecules 2010, 15(3), 1784-1797; https://doi.org/10.3390/molecules15031784
Received: 25 January 2010 / Revised: 20 February 2010 / Accepted: 8 March 2010 / Published: 12 March 2010
Cited by 4 | PDF Full-text (251 KB)
Abstract
Organotin monomers containing dibutyltin groups – dibutyltin citraconate (DBTC) as a new monomer and dibutyltin maleate (DBTM) – were synthesized. Free radical copolymerizations of the organotin monomers with styrene (ST) and butyl acrylate (BA) were performed. The overall conversion was kept low (≤15%
[...] Read more.
Organotin monomers containing dibutyltin groups – dibutyltin citraconate (DBTC) as a new monomer and dibutyltin maleate (DBTM) – were synthesized. Free radical copolymerizations of the organotin monomers with styrene (ST) and butyl acrylate (BA) were performed. The overall conversion was kept low (≤15% wt/wt) for all studied samples and the copolymers composition was determined from tin analysis using the Gillman and Rosenberg method. The reactivity ratios were calculated from the copolymer composition using the Fineman-Ross (FR) method. The synthesized monomers were characterized by elemental analysis, 1H-, 13C-NMR and FTIR spectroscopy. Full article
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Open AccessReview Vitamins and Prostate Cancer Risk
Molecules 2010, 15(3), 1762-1783; https://doi.org/10.3390/molecules15031762
Received: 1 February 2010 / Revised: 5 March 2010 / Accepted: 10 March 2010 / Published: 12 March 2010
Cited by 7 | PDF Full-text (173 KB)
Abstract
Prostate cancer (PC) is the second most common cancer in men worldwide. Its prevention and treatment remain a challenge to clinicians. Here we review the relationship of vitamins to PC risk. Many vitamins and related chemicals, including vitamin A, retinoids, several B vitamins,
[...] Read more.
Prostate cancer (PC) is the second most common cancer in men worldwide. Its prevention and treatment remain a challenge to clinicians. Here we review the relationship of vitamins to PC risk. Many vitamins and related chemicals, including vitamin A, retinoids, several B vitamins, vitamin C, vitamin D and vitamin E have shown their anti-cancer activities as anti-oxidants, activators of transcription factors or factors influencing epigenetic events. Although laboratory tests including the use of animal models showed these vitamins may have anti-PC properties, whether they can effectively prevent the development and/or progression of PC in humans remains to be intensively studied subjects. This review will provide up-to-date information regarding the recent outcomes of laboratory, epidemiology and/or clinical trials on the effects of vitamins on PC prevention and/or treatment. Full article
(This article belongs to the Special Issue Vitamins)
Open AccessReview Gene-Regulatory Activity of α-Tocopherol
Molecules 2010, 15(3), 1746-1761; https://doi.org/10.3390/molecules15031746
Received: 28 January 2010 / Revised: 5 March 2010 / Accepted: 9 March 2010 / Published: 12 March 2010
Cited by 55 | PDF Full-text (404 KB)
Abstract
Vitamin E is an essential vitamin and a lipid soluble antioxidant, at least, under in vitro conditions. The antioxidant properties of vitamin E are exerted through its phenolic hydroxyl group, which donates hydrogen to peroxyl radicals, resulting in the formation of stable lipid
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Vitamin E is an essential vitamin and a lipid soluble antioxidant, at least, under in vitro conditions. The antioxidant properties of vitamin E are exerted through its phenolic hydroxyl group, which donates hydrogen to peroxyl radicals, resulting in the formation of stable lipid species. Beside an antioxidant role, important cell signalling properties of vitamin E have been described. By using gene chip technology we have identified α-tocopherol sensitive molecular targets in vivo including christmas factor (involved in the blood coagulation) and 5α-steroid reductase type 1 (catalyzes the conversion of testosterone to 5α-dihydrotestosterone) being upregulated and γ-glutamyl-cysteinyl synthetase (the rate limiting enzyme in GSH synthesis) being downregulated due to a-tocopherol deficiency. α-Tocopherol regulates signal transduction cascades not only at the mRNA but also at the miRNA level since miRNA 122a (involved in lipid metabolism) and miRNA 125b (involved in inflammation) are downregulated by α-tocopherol. Genetic polymorphisms may determine the biological and gene-regulatory activity of a-tocopherol. In this context we have recently shown that genes encoding for proteins involved in peripheral α-tocopherol transport and degradation are significantly affected by the apoE genotype. Full article
(This article belongs to the Special Issue Vitamins)
Open AccessReview Reactivity and Synthetic Applications of 4,5-Dicyanopyridazine: An Overview
Molecules 2010, 15(3), 1722-1745; https://doi.org/10.3390/molecules15031722
Received: 28 December 2009 / Revised: 12 February 2010 / Accepted: 5 March 2010 / Published: 12 March 2010
Cited by 10 | PDF Full-text (232 KB)
Abstract
Despite the poor reputation of electron-deficient pyridazines in intermolecular Hetero Diels-Alder (HDA) reactions, 4,5-dicyanopyridazine (DCP) showed a surprising reactivity as a heterocyclic azadiene in inverse electron-demand HDA processes with different dienophiles. The use of alkenes, alkynes and enamines as 2p electron counterparts afforded
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Despite the poor reputation of electron-deficient pyridazines in intermolecular Hetero Diels-Alder (HDA) reactions, 4,5-dicyanopyridazine (DCP) showed a surprising reactivity as a heterocyclic azadiene in inverse electron-demand HDA processes with different dienophiles. The use of alkenes, alkynes and enamines as 2p electron counterparts afforded dicyanocyclohexa-1,3-dienes and substituted phthalonitriles, respectively, while the use of suitable bis-dienophiles provides a general strategy for the one-pot synthesis of polycyclic carbo- and hetero-cage systemsthrough pericyclic three-step homodomino processes. HDA reactions with heterocyclic dienophiles allowed direct benzoannelation: in particular, pyrrole and indole derivatives were converted to dicyano-indoles and -carbazoles. In addition an unprecedented reactivity of DCP as a very reactive heterocyclic electrophile at the C-4 carbon was also evidenced: by changing the experimental conditions, cyanopyrrolyl- and cyanoindolyl-pyridazines were obtained through reactions of pyrrole and indole systems as carbon nucleophiles in formal SNAr2 processes where a CN group of DCP acts as leaving group. Thus, careful control of the reaction conditions allows exploitation of both pathways for the synthesis of different classes of heterocyclic derivatives. Full article
(This article belongs to the Special Issue Advances in Heterocyclic Chemistry)
Open AccessReview The Molecular Mechanism of Action of Artemisinin—The Debate Continues
Molecules 2010, 15(3), 1705-1721; https://doi.org/10.3390/molecules15031705
Received: 14 January 2010 / Revised: 23 February 2010 / Accepted: 9 March 2010 / Published: 12 March 2010
Cited by 271 | PDF Full-text (417 KB)
Abstract
Despite international efforts to ‘roll back malaria’ the 2008 World Malaria Report revealed the disease still affects approximately 3 billion people in 109 countries; 45 within the WHO African region. The latest report however does provide some ‘cautious optimism’; more than one third
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Despite international efforts to ‘roll back malaria’ the 2008 World Malaria Report revealed the disease still affects approximately 3 billion people in 109 countries; 45 within the WHO African region. The latest report however does provide some ‘cautious optimism’; more than one third of malarious countries have documented greater than 50% reductions in malaria cases in 2008 compared to 2000. The goal of the Member States at the World Health Assembly and ‘Roll Back Malaria’ (RBM) partnership is to reduce the numbers of malaria cases and deaths recorded in 2000 by 50% or more by the end of 2010. Although malaria is preventable it is most prevalent in poorer countries where prevention is difficult and prophylaxis is generally not an option. The burden of disease has increased by the emergence of multi drug resistant (MDR) parasites which threatens the use of established and cost effective antimalarial agents. After a major change in treatment policies, artemisinins are now the frontline treatment to aid rapid clearance of parasitaemia and quick resolution of symptoms. Since artemisinin and its derivatives are eliminated rapidly, artemisinin combination therapies (ACT’s) are now recommended to delay resistance mechanisms. In spite of these precautionary measures reduced susceptibility of parasites to the artemisinin-based component of ACT’s has developed at the Thai-Cambodian border, a historical ‘hot spot’ for MDR parasite evolution and emergence. This development raises serious concerns for the future of the artemsinins and this is not helped by controversy related to the mode of action. Although a number of potential targets have been proposed the actual mechanism of action remains ambiguous. Interestingly, artemisinins have also shown potent and broad anticancer properties in cell lines and animal models and are becoming established as anti-schistosomal agents. In this review we will discuss the recent evidence explaining bioactivation and potential molecular targets in the chemotherapy of malaria and cancer. Full article
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Open AccessArticle HTS-Driven Discovery of New Chemotypes with West Nile Virus Inhibitory Activity
Molecules 2010, 15(3), 1690-1704; https://doi.org/10.3390/molecules15031690
Received: 25 January 2010 / Revised: 20 February 2010 / Accepted: 8 March 2010 / Published: 12 March 2010
Cited by 9 | PDF Full-text (697 KB)
Abstract
West Nile virus (WNV) is a positive sense, single-stranded RNA virus that can cause illness in humans when transmitted via mosquito vectors. Unfortunately, no antivirals or vaccines are currently available, and therefore efficient and safe antivirals are urgently needed. We developed a high
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West Nile virus (WNV) is a positive sense, single-stranded RNA virus that can cause illness in humans when transmitted via mosquito vectors. Unfortunately, no antivirals or vaccines are currently available, and therefore efficient and safe antivirals are urgently needed. We developed a high throughput screen to discover small molecule probes that inhibit virus infection of Vero E6 cells. A primary screen of a 13,001 compound library at a 10 µM final concentration was conducted using the 384-well format. Z′ values ranged from 0.54–0.83 with a median of 0.74. Average S/B was 17 and S/N for each plate ranged from 10.8 to 23.9. Twenty-six compounds showed a dose response in the HT screen and were further evaluated in a time of addition assay and in a titer reduction assay. Seven compounds showed potential as small molecule probes directed at WNV. The hit rate from the primary screen was 0.185% (24 compounds out of 13,001 compounds) and from the secondary screens was 0.053% (7 out of 13,001 compounds) respectively. Full article
(This article belongs to the Special Issue High-throughput Screening)
Open AccessArticle Influence of Magnolol on the Secretion of α-Toxin by Staphylococcus aureus
Molecules 2010, 15(3), 1679-1689; https://doi.org/10.3390/molecules15031679
Received: 18 January 2010 / Revised: 8 February 2010 / Accepted: 2 March 2010 / Published: 12 March 2010
Cited by 15 | PDF Full-text (400 KB)
Abstract
In this study we investigated the antimicrobial activity of magnolol on Staphylococcus aureus. The minimal inhibitory concentrations of magnolol against 31 S. aureus strains ranged from 4–32 μg/mL. In addition, hemolysin assays, Western blotting, and real-time RT-PCR were performed to investigate the
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In this study we investigated the antimicrobial activity of magnolol on Staphylococcus aureus. The minimal inhibitory concentrations of magnolol against 31 S. aureus strains ranged from 4–32 μg/mL. In addition, hemolysin assays, Western blotting, and real-time RT-PCR were performed to investigate the effect of magnolol on α-toxin secretion by both methicillin-sensitive S. aureus (MSSA) and methicillin-resistant S. aureus (MRSA). The results indicated that sub-inhibitory concentrations of magnolol dose-dependently inhibited the transcription of hla (the gene encoding α-toxin) in S. aureus, resulting in a reduction of α-toxin secretion and, thus, hemolytic activities. Full article
Open AccessArticle A Comparative Study of the Antibacterial, Antifungal and Antioxidant Activity and Total Content of Phenolic Compounds of Cell Cultures and Wild Plants of Three Endemic Species of Ephedra
Molecules 2010, 15(3), 1668-1678; https://doi.org/10.3390/molecules15031668
Received: 30 December 2009 / Revised: 8 February 2010 / Accepted: 8 March 2010 / Published: 11 March 2010
Cited by 33 | PDF Full-text (131 KB)
Abstract
Investigations were carried out to determine antimicrobial and antioxidant properties and total phenol content of three wild species of Ephedra compared with their respective callus cultures. Callus induction was performed in a standard Murashige and Skoog (MS) medium with the following hormonal ranges
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Investigations were carried out to determine antimicrobial and antioxidant properties and total phenol content of three wild species of Ephedra compared with their respective callus cultures. Callus induction was performed in a standard Murashige and Skoog (MS) medium with the following hormonal ranges (mg/L) for every species NAA:1.5, Kin:1 for Ephedra strobiliacea, NAA:2, Kin:1 for Ephedra procera and NAA:2, Kin:0.5 for Ephedra pachyclada. These ranges of PGPR (Plant Growth Promote Regulators) were chosen based on callus induction rates, RGR (Relative Growth Rate) and their fresh weights. An antimicrobial test against five Gram negative and two Gram positive bacteria and two fungi was performed using the disc diffusion method. All methanolic extracts showed antimicrobial activity, but the antimicrobial activity of the callus cultures was lower than those of the wild plants. E. strobilacea showed the highest antimicrobial activity, and all methanolic extracts of the wild plants and callus cultures unexpectedly showed the highest antimicrobial activity against Pseudomonas aeruginosa. A FRAP (Ferric Reducing Antioxidant Power) test was conducted to evaluate extracts for antioxidant activity. E. strobilacea with 1.61 ± 0.08 mmol eq quercetin/gextract and 0.278 ± 0.02 mmol eq quercetin/gextract for the wild plant and callus, respectively, showed the highest results.The total phenol content of extracts was measured by a Folin Ciocalteau test. All the chosen species displayed phenol contents but E. strobilacea had the highest amount (504.9 ± 41.51 μmol eq catechin/gextracts and 114.61 ± 15.13 μmol eq catechin/gextracts for the wild plants and callus, respectively). Full article
Open AccessArticle Hitherto Unrecognized Fluorescence Properties of Coniferyl Alcohol
Molecules 2010, 15(3), 1645-1667; https://doi.org/10.3390/molecules15031645
Received: 14 January 2010 / Revised: 23 February 2010 / Accepted: 8 March 2010 / Published: 11 March 2010
Cited by 3 | PDF Full-text (596 KB)
Abstract
We instituted a quasi-quality assurance program for demonstrating coniferyl alcohol’s fluorescence and fluorescence diminishment following enzymatic oxidation. The magnitude of diminishment was a measure of catalysis. High throughput screening was performed in pseudo-kinetic and endpoint modes by measuring the fluorescence at 416
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We instituted a quasi-quality assurance program for demonstrating coniferyl alcohol’s fluorescence and fluorescence diminishment following enzymatic oxidation. The magnitude of diminishment was a measure of catalysis. High throughput screening was performed in pseudo-kinetic and endpoint modes by measuring the fluorescence at 416 nm following excitation at 290, 310 or 340 nm. Dose-response tracings were linear between two and three orders of magnitude with average limits of detection and quantitation of 1.8 and 6.9 mM coniferyl alcohol, respectively. Oxidation was evident with 0.025 mg/mL laccase or 0.003 mg/mL peroxidase or inside 5 min using 0.5 mg/mL laccase or 5 mM substrate. Sodium chloride inhibited (IC50, 25 mM) laccase oxidation of coniferyl alcohol. Fluorescence from 10 concentrations (1 to 1000 mM) of coniferyl alcohol was stable for 24 hours over 14 excitation/emission cycles at 3 different combinations of excitation and emission wavelengths. In conclusion, coniferyl alcohol absorption and fluorescence assays should facilitate biomass lignin analyses and improve delignification. Full article
(This article belongs to the Special Issue High-throughput Screening)
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Open AccessArticle The Isolated and Combined Effects of Folic Acid and Synthetic Bioactive Compounds against Aβ(25-35)-Induced Toxicity in Human Microglial Cells
Molecules 2010, 15(3), 1632-1644; https://doi.org/10.3390/molecules15031632
Received: 18 February 2010 / Revised: 10 March 2010 / Accepted: 10 March 2010 / Published: 11 March 2010
Cited by 9 | PDF Full-text (475 KB)
Abstract
Folic acid plays an important role in neuronal development. A series of newly synthesized bioactive compounds (NSCs) was reported to exhibit immunoactive and neuroprotective functions. The isolated and combined effects of folic acid and NSCs against β-amyloid (Aβ)-induced cytotoxicity are poorly understood. These
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Folic acid plays an important role in neuronal development. A series of newly synthesized bioactive compounds (NSCs) was reported to exhibit immunoactive and neuroprotective functions. The isolated and combined effects of folic acid and NSCs against β-amyloid (Aβ)-induced cytotoxicity are poorly understood. These effects were tested using human microglia cells (C13NJ) subjected to Aβ(25-35) challenge. According to an MTT assay, treatment of C13NJ cells with Aβ(25-35) at 10~100 μM for 48 h induced 18%~43% cellular death in a dose-dependent manner (p < 0.05). Aβ(25-35) treatment at 25 μM induced nitrite oxide (NO) release, elevated superoxide production, and reduced the distribution of cells in the S phase. Preincubation of C13NJ with 100 μM folic acid protected against Aβ(25-35)-induced cell death, which coincided with a reduction in NO release by folic acid supplements. NSC47 at a level of 50 μM protected against Aβ(25-35)-induced cell death and reduced Aβ-promoted superoxide production (p < 0.05). Folic acid in combination with NSC47 at their cytoprotective doses did not synergistically ameliorate Aβ(25-35)-associated NO release, superoxide production, or cell cycle arrest. Taken together, folic acid or NSC treatment alone, but not the combined regimen, protected against Aβ(25-35)-induced cell death, which may partially, if not completely, be mediated by free radical-scavenging effects. Full article
Open AccessArticle Preparation of 16β-Estradiol Derivative Libraries as Bisubstrate Inhibitors of 17β-Hydroxysteroid Dehydrogenase Type 1 Using the Multidetachable Sulfamate Linker
Molecules 2010, 15(3), 1590-1631; https://doi.org/10.3390/molecules15031590
Received: 26 January 2010 / Revised: 8 February 2010 / Accepted: 3 March 2010 / Published: 10 March 2010
Cited by 8 | PDF Full-text (1264 KB)
Abstract
Combinatorial chemistry is a powerful tool used to rapidly generate a large number of potentially biologically active compounds. In our goal to develop bisubstrate inhibitors of 17β-hydroxysteroid dehydrogenase type 1 (17β-HSD1) that interact with both the substrate (estrone or estradiol) and the cofactor
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Combinatorial chemistry is a powerful tool used to rapidly generate a large number of potentially biologically active compounds. In our goal to develop bisubstrate inhibitors of 17β-hydroxysteroid dehydrogenase type 1 (17β-HSD1) that interact with both the substrate (estrone or estradiol) and the cofactor (NAD(P)H) binding sites, we used parallel solid-phase synthesis to prepare three libraries of 16β-estradiol derivatives with two or three levels of molecular diversity. From estrone, we first synthesized a sulfamate precursor that we loaded on trityl chloride resin using the efficient multidetachable sulfamate linker strategy recently developed in our laboratory. We then introduced molecular diversity [one or two amino acid(s) followed by a carboxylic acid] on steroid nucleus by Fmoc peptide chemistry. Finally, after a nucleophilic cleavage, libraries of 30, 63 and 25 estradiol derivatives were provided. A library of 30 sulfamoylated estradiol derivatives was also generated by acidic cleavage and its members were screened for inhibition of steroid sulfatase. Biological evaluation on homogenated HEK-293 cells overexpressing 17β-HSD1 of the estradiol derivatives carrying different oligoamide-type chains at C-16 first revealed that three levels of molecular diversity (a spacer of two amino acids) were necessary to interact with the adenosine part of the cofactor binding site. Second, the best inhibition was obtained when hydrophobic residues (phenylalanine) were used as building blocks. Full article
(This article belongs to the Special Issue Combinatorial Chemistry)
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