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Molecules, Volume 22, Issue 11 (November 2017)

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Cover Story (view full-size image) The strained dispiro hydrocarbon was endowed with high electron donating ability, which undergo [...] Read more.
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Open AccessArticle Solid Lipid Nanoparticles of Albendazole for Enhancing Cellular Uptake and Cytotoxicity against U-87 MG Glioma Cell Lines
Molecules 2017, 22(11), 2040; https://doi.org/10.3390/molecules22112040
Received: 27 October 2017 / Revised: 14 November 2017 / Accepted: 21 November 2017 / Published: 22 November 2017
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Abstract
Albendazole (ABZ) is an antihelminthic drug used for the treatment of several parasitic infestations. In addition to this, there are reports on the anticancer activity of ABZ against a wide range of cancer types. However, its effect on glioma has not yet been
[...] Read more.
Albendazole (ABZ) is an antihelminthic drug used for the treatment of several parasitic infestations. In addition to this, there are reports on the anticancer activity of ABZ against a wide range of cancer types. However, its effect on glioma has not yet been reported. In the present study, cytotoxicity of ABZ and ABZ loaded solid lipid nanoparticles (ASLNs) was tested in human glioma/astrocytoma cell line (U-87 MG). Using glyceryl trimyristate as lipid carrier and tween 80 as surfactant spherical ASLNs with an average size of 218.4 ± 5.1 nm were prepared by a combination of high shear homogenization and probe sonication methods. A biphasic in vitro release pattern of ABZ from ASLNs was observed, where 82% of ABZ was released in 24 h. In vitro cell line studies have shown that ABZ in the form of ASLNs was more cytotoxic (IC50 = 4.90 µg/mL) to U-87 MG cells compared to ABZ in the free form (IC50 = 13.30 µg/mL) due to the efficient uptake of the former by these cells. Full article
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Open AccessArticle Direct Modification of Microcrystalline Cellulose with Ethylenediamine for Use as Adsorbent for Removal Amitriptyline Drug from Environment
Molecules 2017, 22(11), 2039; https://doi.org/10.3390/molecules22112039
Received: 4 October 2017 / Revised: 2 November 2017 / Accepted: 17 November 2017 / Published: 22 November 2017
Cited by 1 | PDF Full-text (4556 KB) | HTML Full-text | XML Full-text
Abstract
Cellulose derivatives have been widely used as adsorbents for the removal of micropollutants such as drugs, dyes, and metals, due to their abundance, low cost and non-contaminating nature. In this context, several studies have been performed searching for new adsorbents (cellulose derivatives) efficient
[...] Read more.
Cellulose derivatives have been widely used as adsorbents for the removal of micropollutants such as drugs, dyes, and metals, due to their abundance, low cost and non-contaminating nature. In this context, several studies have been performed searching for new adsorbents (cellulose derivatives) efficient at contaminant removal from aqueous solutions. Thus, a new adsorbent was synthesized by chemical modification of cellulose with ethylenediamine in the absence of solvent and applied to the adsorption of amitriptyline (AMI) in aqueous solution. The modification reaction was confirmed by X-ray Diffraction (XRD), elemental analysis, Fourier Transform Infrared Spectroscopy (FTIR), Thermogravimetry/Differential Scanning Calorimeter (TG/DSC), solid state Nuclear Magnetic Resonance of 1H and 13C (1H-NMR and 13C-NMR). Moreover, the effectiveness of reaction was confirmed by computational calculations using Density Functional Theory (DFT) at level B3LYP/6-31G(d). This adsorption process was influenced by pH, time, concentration, temperature and did not show significant changes due to the ionic strength variation. Through these experiments, it was observed that the maximum adsorption capacity of AMI by CN polymer at 298 K, 300 min, and pH 7 was 87.66 ± 0.60 mg·g−1. Full article
(This article belongs to the Special Issue Cellulose Chemical Modifications—Towards Sustainable Materials)
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Open AccessArticle Preparation of Vitexin Nanoparticles by Combining the Antisolvent Precipitation and High Pressure Homogenization Approaches Followed by Lyophilization for Dissolution Rate Enhancement
Molecules 2017, 22(11), 2038; https://doi.org/10.3390/molecules22112038
Received: 23 October 2017 / Revised: 16 November 2017 / Accepted: 18 November 2017 / Published: 22 November 2017
Cited by 1 | PDF Full-text (3512 KB) | HTML Full-text | XML Full-text
Abstract
Vitexin, a natural flavonoid found in many medicinal plants, is well known for its rich pharmacological activities. However, the poor water solubility of vitexin has limited its therapeutic application. The aim of this study was to prepare the nanoparticles of vitexin by combining
[...] Read more.
Vitexin, a natural flavonoid found in many medicinal plants, is well known for its rich pharmacological activities. However, the poor water solubility of vitexin has limited its therapeutic application. The aim of this study was to prepare the nanoparticles of vitexin by combining the antisolvent precipitation (ASP) and high pressure homogenization (HPH) approaches followed by lyophilization for improving the dissolution rate of this poorly water-soluble drug. The effects of main factors influencing the mean particle size (MPS) of vitexin were investigated and optimized. Under optimum conditions, vitexin nanosuspensions with an MPS of 80.5 nm were obtained and then lyophilized to form nanoparticles. The obtained vitexin nanoparticles were further characterized by scanning electron microscopy (SEM), Fourier transform infrared spectroscopy (FTIR), mass spectrometry (MS), X-ray powder diffraction (XRPD), gas chromatography (GC) and dissolution testing. The results showed that the nanoparticles of vitexin were converted into an amorphous form, with its chemical structure unchanged. Additionally, the residual dimethyl sulfoxide (DMSO) is lower than the International Conference on Harmonization (ICH) limit for class 3 solvents. The dissolution rate of processed vitexin was significantly higher (5.58-fold) than that of raw drug. Overall, the combinative process we developed is an effective way to produce vitexin nanoparticles with markedly enhanced dissolution rate. Full article
(This article belongs to the Section Nanochemistry)
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Open AccessArticle Large-Scale Analysis of Antimicrobial Activities in Relation to Amphipathicity and Charge Reveals Novel Characterization of Antimicrobial Peptides
Molecules 2017, 22(11), 2037; https://doi.org/10.3390/molecules22112037
Received: 16 October 2017 / Revised: 13 November 2017 / Accepted: 20 November 2017 / Published: 22 November 2017
Cited by 1 | PDF Full-text (994 KB) | HTML Full-text | XML Full-text
Abstract
It has been unclear to which antimicrobial activities (e.g., anti-gram-positive bacterial, anti-gram-negative bacterial, antifungal, antiparasitic, and antiviral activities) of antimicrobial peptides (AMPs) a given physiochemical property matters most. This is the first computational study using large-scale AMPs to examine the relationships between antimicrobial
[...] Read more.
It has been unclear to which antimicrobial activities (e.g., anti-gram-positive bacterial, anti-gram-negative bacterial, antifungal, antiparasitic, and antiviral activities) of antimicrobial peptides (AMPs) a given physiochemical property matters most. This is the first computational study using large-scale AMPs to examine the relationships between antimicrobial activities and two major physiochemical properties of AMPs—amphipathicity and net charge. The results showed that among all kinds of antimicrobial activities, amphipathicity and net charge best differentiated between AMPs with and without anti-gram-negative bacterial activities. In terms of amphipathicity and charge, all the AMPs whose activities were significantly associated with amphipathicity and net charge were alike except those with anti-gram-positive bacterial activities. Furthermore, the higher the amphipathic value, the greater the proportion of AMPs possessing both antibacterial and antifungal activities. This dose–response-like pattern suggests a possible causal relationship—dual antibacterial and antifungal activities of AMPs may be attributable to amphipathicity. These novel findings could be useful for identifying potent AMPs computationally. Full article
(This article belongs to the Special Issue Bioactive Natural Peptides As A Pipeline For Therapeutics)
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Open AccessArticle Action of Monomeric/Gemini Surfactants on Free Cells and Biofilm of Asaia lannensis
Molecules 2017, 22(11), 2036; https://doi.org/10.3390/molecules22112036
Received: 25 October 2017 / Revised: 19 November 2017 / Accepted: 21 November 2017 / Published: 22 November 2017
Cited by 2 | PDF Full-text (1617 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
We investigated the biological activity of surfactants based on quaternary ammonium compounds: gemini surfactant hexamethylene-1,6-bis-(N,N-dimethyl-N-dodecylammonium bromide) (C6), synthesized by the reaction of N,N-dimethyl-N-dodecylamine with 1,6-dibromohexane, and its monomeric analogue dodecyltrimethylammonium bromide (DTAB). The experiments were performed
[...] Read more.
We investigated the biological activity of surfactants based on quaternary ammonium compounds: gemini surfactant hexamethylene-1,6-bis-(N,N-dimethyl-N-dodecylammonium bromide) (C6), synthesized by the reaction of N,N-dimethyl-N-dodecylamine with 1,6-dibromohexane, and its monomeric analogue dodecyltrimethylammonium bromide (DTAB). The experiments were performed with bacteria Asaia lannensis, a common spoilage in the beverage industry. The minimal inhibitory concentration (MIC) values were determined using the tube standard two-fold dilution method. The growth and adhesive properties of bacterial cells were studied in different culture media, and the cell viability was evaluated using plate count method. Both of the surfactants were effective against the bacterial strain, but the MIC of gemini compound was significantly lower. Both C6 and DTAB exhibited anti-adhesive abilities. Treatment with surfactants at or below MIC value decreased the number of bacterial cells that were able to form biofilm, however, the gemini surfactant was more effective. The used surfactants were also found to be able to eradicate mature biofilms. After 4 h of treatment with C6 surfactant at concentration 10 MIC, the number of bacterial cells was reduced by 91.8%. The results of this study suggest that the antibacterial activity of the gemini compound could make it an effective microbiocide against the spoilage bacteria Asaia sp. in both planktonic and biofilm stages. Full article
(This article belongs to the Section Chemical Biology)
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Open AccessArticle A New Synthetic Route to Polyhydrogenated Pyrrolo[3,4-b]pyrroles by the Domino Reaction of 3-Bromopyrrole-2,5-Diones with Aminocrotonic Acid Esters
Molecules 2017, 22(11), 2035; https://doi.org/10.3390/molecules22112035
Received: 4 November 2017 / Revised: 16 November 2017 / Accepted: 20 November 2017 / Published: 22 November 2017
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Abstract
A new synthetic approach to polyfunctional hexahydropyrrolo[3,4-b]pyrroles was developed based on cyclization of N-arylbromomaleimides with aminocrotonic acid esters. A highly chemo- and stereoselective reaction is a Hantzsch-type domino process, involving the steps of initial nucleophilic C-addition or substitution and subsequent intramolecular
[...] Read more.
A new synthetic approach to polyfunctional hexahydropyrrolo[3,4-b]pyrroles was developed based on cyclization of N-arylbromomaleimides with aminocrotonic acid esters. A highly chemo- and stereoselective reaction is a Hantzsch-type domino process, involving the steps of initial nucleophilic C-addition or substitution and subsequent intramolecular nucleophilic addition without recyclyzation of imide cycle. Full article
(This article belongs to the collection Heterocyclic Compounds)
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Open AccessArticle Multicenter (FX)n/NH3 Halogen Bonds (X = Cl, Br and n = 1–5). QTAIM Descriptors of the Strength of the X∙∙∙N Interaction
Molecules 2017, 22(11), 2034; https://doi.org/10.3390/molecules22112034
Received: 10 October 2017 / Revised: 14 November 2017 / Accepted: 14 November 2017 / Published: 22 November 2017
Cited by 1 | PDF Full-text (1615 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
In the present work an in depth deep electronic study of multicenter XBs (FX)n/NH3 (X = Cl, Br and n = 1–5) is conducted. The ways in which X∙∙∙X lateral contacts affect the electrostatic or covalent nature of the X∙∙∙N
[...] Read more.
In the present work an in depth deep electronic study of multicenter XBs (FX)n/NH3 (X = Cl, Br and n = 1–5) is conducted. The ways in which X∙∙∙X lateral contacts affect the electrostatic or covalent nature of the X∙∙∙N interactions are explored at the CCSD(T)/aug-cc-pVTZ level and in the framework of the quantum theory of atoms in molecules (QTAIM). Calculations show that relatively strong XBs have been found with interaction energies lying between −41 and −90 kJ mol−1 for chlorine complexes, and between −56 and −113 kJ mol−1 for bromine complexes. QTAIM parameters reveal that in these complexes: (i) local (kinetics and potential) energy densities measure the ability that the system has to concentrate electron charge density at the intermolecular X∙∙∙N region; (ii) the delocalization indices [δ(A,B)] and the exchange contribution [VEX(X,N)] of the interacting quantum atoms (IQA) scheme, could constitute a quantitative measure of the covalence of these molecular interactions; (iii) both classical electrostatic and quantum exchange show high values, indicating that strong ionic and covalent contributions are not mutually exclusive. Full article
(This article belongs to the Special Issue Halogen Bonds and Beyond)
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Open AccessArticle WxC-β-SiC Nanocomposite Catalysts Used in Aqueous Phase Hydrogenation of Furfural
Molecules 2017, 22(11), 2033; https://doi.org/10.3390/molecules22112033
Received: 5 October 2017 / Revised: 17 November 2017 / Accepted: 19 November 2017 / Published: 22 November 2017
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Abstract
This study investigates the effects of the addition of tungsten on the structure, phase composition, textural properties and activities of β-SiC-based catalysts in the aqueous phase hydrogenation of furfural. Carbothermal reduction of SiO2 in the presence of WO3 at 1550 °C
[...] Read more.
This study investigates the effects of the addition of tungsten on the structure, phase composition, textural properties and activities of β-SiC-based catalysts in the aqueous phase hydrogenation of furfural. Carbothermal reduction of SiO2 in the presence of WO3 at 1550 °C in argon resulted in the formation of WxC-β-SiC nanocomposite powders with significant variations in particle morphology and content of WxC-tipped β-SiC nano-whiskers, as revealed by TEM and SEM-EDS. The specific surface area (SSA) of the nanocomposite strongly depended on the amount of tungsten and had a notable impact on its catalytic properties for the production of furfuryl alcohol (FA) and tetrahydrofurfuryl alcohol (THFA). Nanocomposite WxC-β-SiC catalysts with 10 wt % W in the starting mixture had the highest SSA and the smallest WxC crystallites. Some 10 wt % W nanocomposite catalysts demonstrated up to 90% yield of THFA, in particular in the reduction of furfural derived from biomass, although the reproducible performance of such catalysts has yet to be achieved. Full article
(This article belongs to the Section Green Chemistry)
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Open AccessArticle New Metabolites of Coumarin Detected in Human Urine Using Ultra Performance Liquid Chromatography/Quadrupole-Time-of-Flight Tandem Mass Spectrometry
Molecules 2017, 22(11), 2031; https://doi.org/10.3390/molecules22112031
Received: 12 October 2017 / Revised: 12 November 2017 / Accepted: 17 November 2017 / Published: 22 November 2017
Cited by 1 | PDF Full-text (2865 KB) | HTML Full-text | XML Full-text
Abstract
Coumarin (1,2-benzopyrone) is a natural compound whose metabolism in humans was established in the 1970s. However, a new metabolite was recently identified in human plasma, indicating that the metabolism of coumarin has not been completely elucidated. To complement the knowledge of its metabolism,
[...] Read more.
Coumarin (1,2-benzopyrone) is a natural compound whose metabolism in humans was established in the 1970s. However, a new metabolite was recently identified in human plasma, indicating that the metabolism of coumarin has not been completely elucidated. To complement the knowledge of its metabolism, a rapid and sensitive method using UPLC-QTOF-MS was developed. A total of 12 metabolites was identified using MetaboLynxTM software, including eight metabolites not previously reported in human urine. The identified biotransformation included hydroxylation, glucuronidation, sulfation, methylation, and conjugation with N-acetylcysteine. The present work demonstrates that the metabolism study of coumarin was incomplete, possibly due to limitations of old techniques. The identification of eight inedited metabolites of such a simple molecule suggests that the information regarding the metabolism of other drugs may also be incomplete, and therefore, new investigations are necessary. Full article
(This article belongs to the Special Issue Versatile Coumarins)
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Open AccessArticle The Rosiglitazone-Like Effects of Vitexilactone, a Constituent from Vitex trifolia L. in 3T3-L1 Preadipocytes
Molecules 2017, 22(11), 2030; https://doi.org/10.3390/molecules22112030
Received: 18 October 2017 / Revised: 8 November 2017 / Accepted: 17 November 2017 / Published: 22 November 2017
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Abstract
The increased number of patients with type 2 diabetes (T2D) has become a worldwide problem, and insulin sensitizers such as thiazolidinediones (TZDs) are used as therapeutic agents. We found that extracts of Vitex trifolia L. (V. trifolia), a medicinal plant from
[...] Read more.
The increased number of patients with type 2 diabetes (T2D) has become a worldwide problem, and insulin sensitizers such as thiazolidinediones (TZDs) are used as therapeutic agents. We found that extracts of Vitex trifolia L. (V. trifolia), a medicinal plant from Myanmar, induced adipogenesis similar to rosiglitazone (ROS), which is a TZD, in 3T3-L1 preadipocytes. In the present study, we attempted to isolate from V. trifolia those compounds that showed ROS-like effects. Among the extracts of hexane, ethyl acetate, and methanol obtained from V. trifolia, the ethyl acetate extract with the strongest ROS-like effects was purified by various chromatographic methods to obtain three known compounds: vitexilactone (1), vitexicarpin (2) and oleanolic acid (3). Among the isolated compounds, the ROS-like action of 1 was the strongest. The effects of 1 on 3T3-L1 cells during adipogenesis were compared with those of ROS. Both 1 and ROS increased lipid accumulation, the expression of adiponectin and GLUT4 in the cell membrane and decreased both the size of adipocytes and the phosphorylation of IRS-1, ERK1/2 and JNK in 3T3-L1 cells. In contrast, unlike ROS, the induction of proteins involved in lipogenesis was partial. ROS-like effects of 1 in 3T3-L1 cells were suppressed by the addition of bisphenol A diglycidyl ether (BADGE), one of a peroxisome proliferator-activated receptor γ (PPARγ) antagonists, suggesting that the action of 1 on adipocytes is mediated by PPARγ. From the results of the present study, it can be concluded that 1 is a novel insulin sensitizer candidate. Full article
(This article belongs to the collection Bioactive Compounds)
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Open AccessReview Dynamic Docking: A Paradigm Shift in Computational Drug Discovery
Molecules 2017, 22(11), 2029; https://doi.org/10.3390/molecules22112029
Received: 27 October 2017 / Revised: 18 November 2017 / Accepted: 19 November 2017 / Published: 22 November 2017
Cited by 5 | PDF Full-text (1630 KB) | HTML Full-text | XML Full-text
Abstract
Molecular docking is the methodology of choice for studying in silico protein-ligand binding and for prioritizing compounds to discover new lead candidates. Traditional docking simulations suffer from major limitations, mostly related to the static or semi-flexible treatment of ligands and targets. They also
[...] Read more.
Molecular docking is the methodology of choice for studying in silico protein-ligand binding and for prioritizing compounds to discover new lead candidates. Traditional docking simulations suffer from major limitations, mostly related to the static or semi-flexible treatment of ligands and targets. They also neglect solvation and entropic effects, which strongly limits their predictive power. During the last decade, methods based on full atomistic molecular dynamics (MD) have emerged as a valid alternative for simulating macromolecular complexes. In principle, compared to traditional docking, MD allows the full exploration of drug-target recognition and binding from both the mechanistic and energetic points of view (dynamic docking). Binding and unbinding kinetic constants can also be determined. While dynamic docking is still too computationally expensive to be routinely used in fast-paced drug discovery programs, the advent of faster computing architectures and advanced simulation methodologies are changing this scenario. It is feasible that dynamic docking will replace static docking approaches in the near future, leading to a major paradigm shift in in silico drug discovery. Against this background, we review the key achievements that have paved the way for this progress. Full article
(This article belongs to the Special Issue Frontiers in Computational Chemistry for Drug Discovery)
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Open AccessFeature PaperReview Synthesis of Spironucleosides: Past and Future Perspectives
Molecules 2017, 22(11), 2028; https://doi.org/10.3390/molecules22112028
Received: 16 October 2017 / Revised: 17 November 2017 / Accepted: 19 November 2017 / Published: 22 November 2017
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Abstract
Spironucleosides are a type of conformationally restricted nucleoside analogs in which the anomeric carbon belongs simultaneously to the sugar moiety and to the base unit. This locks the nucleic base in a specific orientation around the N-glycosidic bond, imposing restrictions on the
[...] Read more.
Spironucleosides are a type of conformationally restricted nucleoside analogs in which the anomeric carbon belongs simultaneously to the sugar moiety and to the base unit. This locks the nucleic base in a specific orientation around the N-glycosidic bond, imposing restrictions on the flexibility of the sugar moiety. Anomeric spiro-functionalized nucleosides have gained considerable importance with the discovery of hydantocidin, a natural spironucleoside isolated from fermentation broths of Streptomyces hygroscopicus which exhibits potent herbicidal activity. The biological activity of hydantocidin has prompted considerable synthetic interest in this nucleoside and also in a variety of analogues, since important pharmaceutical leads can be found among modified nucleoside analogues. We present here an overview of the most important advances in the synthesis of spironucleosides. Full article
(This article belongs to the Special Issue Advances in Spiro Compounds)
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Open AccessArticle Transformation of a Thermostable G-Quadruplex Structure into DNA Duplex Driven by Reverse Gyrase
Molecules 2017, 22(11), 2021; https://doi.org/10.3390/molecules22112021
Received: 8 November 2017 / Revised: 14 November 2017 / Accepted: 17 November 2017 / Published: 22 November 2017
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Abstract
Reverse gyrase is a topoisomerase that can introduce positive supercoils to its substrate DNA. It is demonstrated in our studies that a highly thermal stable G-quadruplex structure in a mini-plasmid DNA was transformed into its duplex conformation after a treatment with reverse gyrase.
[...] Read more.
Reverse gyrase is a topoisomerase that can introduce positive supercoils to its substrate DNA. It is demonstrated in our studies that a highly thermal stable G-quadruplex structure in a mini-plasmid DNA was transformed into its duplex conformation after a treatment with reverse gyrase. The structural difference of the topoisomers were verified and analyzed by gel electrophoresis, atomic force microscopy examination, and endonuclease digestion assays. All evidence suggested that the overwinding structure of positive supercoil could provide a driven force to disintegrate G-quadruplex and reform duplex. The results of our studies could suggest that hyperthermophiles might use reverse gyrase to manipulate the disintegration of non-B DNA structures and safekeep their genomic information. Full article
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Open AccessArticle Four New Glycosides from the Rhizoma of Anemarrhena asphodeloides
Molecules 2017, 22(11), 1995; https://doi.org/10.3390/molecules22111995
Received: 28 October 2017 / Accepted: 15 November 2017 / Published: 22 November 2017
Cited by 1 | PDF Full-text (585 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Four new compounds, aneglycoside A–C (13) and timosaponin U (4), were isolated from the rhizomes of Anemarrhena asphodeloides. Their structures were determined through extensive spectroscopic analysis, chemical characteristics, and high-resolution mass spectrometry (HRMS). All the isolations
[...] Read more.
Four new compounds, aneglycoside A–C (13) and timosaponin U (4), were isolated from the rhizomes of Anemarrhena asphodeloides. Their structures were determined through extensive spectroscopic analysis, chemical characteristics, and high-resolution mass spectrometry (HRMS). All the isolations were evaluated for cytotoxicity against HepG2, Hela, and SGC7901 human cancer lines. Compounds 1, 2, and 4 showed weak antiproliferative activities on HepG2, Hela, and SGC7901 cells. Full article
(This article belongs to the Section Natural Products Chemistry)
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Open AccessArticle Application of Enzymatic Extracts from a CALB Standard Strain as Biocatalyst within the Context of Conventional Biodiesel Production Optimization
Molecules 2017, 22(11), 2025; https://doi.org/10.3390/molecules22112025
Received: 30 October 2017 / Revised: 16 November 2017 / Accepted: 18 November 2017 / Published: 21 November 2017
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Abstract
The application of biocatalysts in the transesterification process of triglycerides (TG) allows integrating the glycerol in the form of monoglyceride (MG), sharply increasing the yield and the environmental sustainability of the conventional biodiesel production process. This is known as Ecodiesel. To overcome the
[...] Read more.
The application of biocatalysts in the transesterification process of triglycerides (TG) allows integrating the glycerol in the form of monoglyceride (MG), sharply increasing the yield and the environmental sustainability of the conventional biodiesel production process. This is known as Ecodiesel. To overcome the inconvenient of the high cost of the currently employed highly purified commercial enzymes, the use of scarcely purified extracts obtained from standard strains of the same species of commercial lipases currently applied in this process is being investigated. Thus, Candida antarctica type B (CALB) was chosen to determine the optimal conditions of culture of this yeast. The standard strain was obtained from the Spanish Type Microbial Cultures Collection (CECT) and has been used to carry out several studies to elucidate its optimum growth conditions. Through a process of lyophilization with prior dialysis of the liquid cultures, the enzymatic extracts were obtained. The different obtained cultures have been applied as biocatalysts in the 1,3-selective transesterification reaction of sunflower oil with ethanol to obtain Ecodiesel (FAEE + MG). Selectivity and reaction yields were obtained by gas chromatography. Acceptable yields are obtained during the reaction time as well as in successive reactions, demonstrating the feasibility of using these CALB enzymatic extracts as biocatalysts. Full article
(This article belongs to the Special Issue Meeting of the Spanish Catalysis Society (SECAT’17))
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Open AccessArticle Application of an Ultrafine Shearing Method for the Extraction of C-Phycocyanin from Spirulina platensis
Molecules 2017, 22(11), 2023; https://doi.org/10.3390/molecules22112023
Received: 31 October 2017 / Revised: 17 November 2017 / Accepted: 17 November 2017 / Published: 21 November 2017
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Abstract
Cell disruption is an important step during the extraction of C-phycocyanin from Spirulina platensis. An ultrafine shearing method is introduced and combined with soaking and ultrasonication to disrupt the cell walls of S. platensis efficiently and economically. Five kinds of cell disruption
[...] Read more.
Cell disruption is an important step during the extraction of C-phycocyanin from Spirulina platensis. An ultrafine shearing method is introduced and combined with soaking and ultrasonication to disrupt the cell walls of S. platensis efficiently and economically. Five kinds of cell disruption method, including soaking, ultrasonication, freezing-thawing, soaking-ultrafine shearing and soaking-ultrafine shearing-ultrasonication were applied to break the cell walls of S. platensis. The effectiveness of cell breaking was evaluated based on the yield of the C-phycocyanin. The results show that the maximum C-phycocyanin yield was 9.02%, achieved by the soaking-ultrafine shearing-ultrasonication method, followed by soaking (8.43%), soaking-ultrafine shearing (8.89%), freezing and thawing (8.34%), and soaking-ultrasonication (8.62%). The soaking-ultrafine shearing-ultrasonication method is a novel technique for breaking the cell walls of S. platensis for the extraction of C-phycocyanin. Full article
(This article belongs to the collection Bioactive Compounds)
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Open AccessArticle Microneedle-Assisted Percutaneous Delivery of a Tetramethylpyrazine-Loaded Microemulsion
Molecules 2017, 22(11), 2022; https://doi.org/10.3390/molecules22112022
Received: 23 September 2017 / Accepted: 15 November 2017 / Published: 21 November 2017
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Abstract
This study examined the efficacy of the percutaneous delivery of a tetramethylpyrazine-loaded microemulsion (TMP-ME) on skin pretreated with microneedles (MN). The TMP-ME formulation was optimized in vitro with skin permeation experiments, using a uniform experimental design, guided by a pseudo-ternary phase diagram, in
[...] Read more.
This study examined the efficacy of the percutaneous delivery of a tetramethylpyrazine-loaded microemulsion (TMP-ME) on skin pretreated with microneedles (MN). The TMP-ME formulation was optimized in vitro with skin permeation experiments, using a uniform experimental design, guided by a pseudo-ternary phase diagram, in which the TMP skin permeation level and mean particle size were indices. The effects of MN pretreatment on skin permeation by TMP-ME were assessed using in vitro skin permeation, in vivo skin microdialysis, and pharmacokinetic studies in rats. The influence of MN pretreatment on the skin barrier function was evaluated by measuring the electrical resistance of rat skin before and after MN insertion. In the optimal formulation of TMP-ME, the weight percentages of Maisine® 35-1 (oil phase), Labrasol® (surfactant), and Transcutol® P (co-surfactant) were 7%, 30% and 10%, respectively, with 1.5% TMP loading. In the in vitro skin permeation study, MN-assisted TMP-ME exhibited a two-fold increase in a 24-h cumulative TMP permeation compared with TMP-ME alone (p < 0.05). In the skin microdialysis study, TMP in MN-assisted TMP-ME exhibited a 1.25-fold increase in Cmax, a 0.93-fold decrease in Tmax, and a 0.88-fold increase in AUC0–t (p < 0.05). Similarly, in the pharmacokinetic study, TMP in MN-assisted TMP-ME exhibited a 2.11-fold increase in Cmax, a 0.67-fold decrease in Tmax, and a 1.07-fold increase in AUC0–t (p < 0.05). The percutaneous electrical resistance of rat skin before and after MN insertion was 850 ± 50 Ω/cm2 and 283 ± 104 Ω/cm2 respectively, indicating that MN dramatically compromises the skin barrier. These results suggest that MN assistance increases the skin permeation rate and the extent of percutaneous absorption of TMP-ME, and that the mechanism may involve the reversible barrier perturbation effect. The rate and extent of percutaneous absorption of TMP-ME can be significantly enhanced by MN assistance, possibly because MN causes a reversible barrier perturbation effect on skin. Full article
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Open AccessArticle Inkjet Printing of Drug-Loaded Mesoporous Silica Nanoparticles—A Platform for Drug Development
Molecules 2017, 22(11), 2020; https://doi.org/10.3390/molecules22112020
Received: 9 October 2017 / Revised: 12 November 2017 / Accepted: 17 November 2017 / Published: 21 November 2017
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Abstract
Mesoporous silica nanoparticles (MSNs) have shown great potential in improving drug delivery of poorly water soluble (BCS class II, IV) and poorly permeable (BCS class III, IV) drugs, as well as facilitating successful delivery of unstable compounds. The nanoparticle technology would allow improved
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Mesoporous silica nanoparticles (MSNs) have shown great potential in improving drug delivery of poorly water soluble (BCS class II, IV) and poorly permeable (BCS class III, IV) drugs, as well as facilitating successful delivery of unstable compounds. The nanoparticle technology would allow improved treatment by reducing adverse reactions of currently approved drugs and possibly reintroducing previously discarded compounds from the drug development pipeline. This study aims to highlight important aspects in mesoporous silica nanoparticle (MSN) ink formulation development for digital inkjet printing technology and to advice on choosing a method (2D/3D) for nanoparticle print deposit characterization. The results show that both unfunctionalized and polyethyeleneimine (PEI) surface functionalized MSNs, as well as drug-free and drug-loaded MSN–PEI suspensions, can be successfully inkjet-printed. Furthermore, the model BCS class IV drug remained incorporated in the MSNs and the suspension remained physically stable during the processing time and steps. This proof-of-concept study suggests that inkjet printing technology would be a flexible deposition method of pharmaceutical MSN suspensions to generate patterns according to predefined designs. The concept could be utilized as a versatile drug screening platform in the future due to the possibility of accurately depositing controlled volumes of MSN suspensions on various materials. Full article
(This article belongs to the Special Issue Mesoporous Silica in Biomedical Applications)
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Open AccessArticle The Protective Effects of Astaxanthin on the OVA-Induced Asthma Mice Model
Molecules 2017, 22(11), 2019; https://doi.org/10.3390/molecules22112019
Received: 31 October 2017 / Accepted: 17 November 2017 / Published: 21 November 2017
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Abstract
Although astaxanthin has a variety of biological activities such as anti-oxidant effects, inhibitory effects on skin deterioration and anti-inflammatory effects, its effect on asthma has not been studied. In this paper, the inhibitory effect of astaxanthin on airway inflammation in a mouse model
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Although astaxanthin has a variety of biological activities such as anti-oxidant effects, inhibitory effects on skin deterioration and anti-inflammatory effects, its effect on asthma has not been studied. In this paper, the inhibitory effect of astaxanthin on airway inflammation in a mouse model of ovalbumin (OVA)-induced asthma was investigated. We evaluated the number of total cells, Th1/2 mediated inflammatory cytokines in bronchoalveolar lavage fluid (BALF) and airway hyperresponsiveness as well as histological structure. The level of total IgE, IgG1, IgG2a, OVA-specific IgG1, and OVA-specific IgG2a were also examined. The oral administration of 50 mg/mL astaxanthin inhibited the respiratory system resistance, elastance, newtonian resistance, tissue damping, and tissue elastance. Also, astaxanthin suppressed the total cell number, IL-4, and IL-5, and increased the IFN-γ in the BALF. In the sera, total IgE, IgG1, and OVA-specific IgG1 were reduced by astaxanthin exposure and IgG2a and OVA-specific IgG2a were enhanced via oral administration of astaxanthin. Infiltration of inflammatory cells in the lung, production of mucus, lung fibrosis, and expression of caspase-1 or caspase-3 were suppressed in OVA-induced asthmatic animal treated with astaxanthin. These results suggest that astaxanthin may have therapeutic potential for treating asthma via inhibiting Th2-mediated cytokine and enhancing Th1-mediated cytokine. Full article
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Open AccessFeature PaperReview Synthesis of Nitrogen Heterocycles Using Samarium(II) Iodide
Molecules 2017, 22(11), 2018; https://doi.org/10.3390/molecules22112018
Received: 27 October 2017 / Revised: 11 November 2017 / Accepted: 13 November 2017 / Published: 21 November 2017
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Abstract
Nitrogen heterocycles represent vital structural motifs in biologically-active natural products and pharmaceuticals. As a result, the development of new, convenient and more efficient processes to N-heterocycles is of great interest to synthetic chemists. Samarium(II) iodide (SmI2, Kagan’s reagent) has been
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Nitrogen heterocycles represent vital structural motifs in biologically-active natural products and pharmaceuticals. As a result, the development of new, convenient and more efficient processes to N-heterocycles is of great interest to synthetic chemists. Samarium(II) iodide (SmI2, Kagan’s reagent) has been widely used to forge challenging C–C bonds through reductive coupling reactions. Historically, the use of SmI2 in organic synthesis has been focused on the construction of carbocycles and oxygen-containing motifs. Recently, significant advances have taken place in the use of SmI2 for the synthesis of nitrogen heterocycles, enabled in large part by the unique combination of high reducing power of this reagent (E1/2 of up to −2.8 V) with excellent chemoselectivity of the reductive umpolung cyclizations mediated by SmI2. In particular, radical cross-coupling reactions exploiting SmI2-induced selective generation of aminoketyl radicals have emerged as concise and efficient methods for constructing 2-azabicycles, pyrrolidines and complex polycyclic barbiturates. Moreover, a broad range of novel processes involving SmI2-promoted formation of aminyl radicals have been leveraged for the synthesis of complex nitrogen-containing molecular architectures by direct and tethered pathways. Applications to the synthesis of natural products have highlighted the generality of processes and the intermediates accessible with SmI2. In this review, recent advances involving the synthesis of nitrogen heterocycles using SmI2 are summarized, with a major focus on reductive coupling reactions that enable one-step construction of nitrogen-containing motifs in a highly efficient manner, while taking advantage of the spectacular selectivity of the venerable Kagan’s reagent. Full article
(This article belongs to the Section Organic Chemistry)
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Open AccessArticle How Secondary and Tertiary Amide Moieties are Molecular Stations for Dibenzo-24-crown-8 in [2]Rotaxane Molecular Shuttles?
Molecules 2017, 22(11), 2017; https://doi.org/10.3390/molecules22112017
Received: 3 November 2017 / Accepted: 17 November 2017 / Published: 21 November 2017
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Abstract
Interlocked molecular machines like [2]rotaxanes are intriguing aesthetic molecules. The control of the localization of the macrocycle, which surrounds a molecular axle, along the thread leads to translational isomers of very different properties. Although many moieties have been used as sites of interactions
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Interlocked molecular machines like [2]rotaxanes are intriguing aesthetic molecules. The control of the localization of the macrocycle, which surrounds a molecular axle, along the thread leads to translational isomers of very different properties. Although many moieties have been used as sites of interactions for crown ethers, the very straightforwardly obtained amide motif has more rarely been envisaged as molecular station. In this article, we report the use of secondary and tertiary amide moieties as efficient secondary molecular station in pH-sensitive molecular shuttles. Depending on the N-substitution of the amide station, and on deprotonation or deprotonation-carbamoylation, the actuation of the molecular machinery differs accordingly to very distinct interactions between the axle and the DB24C8. Full article
(This article belongs to the Special Issue Interlocked Molecules, Molecular Machines, Motors and Muscles)
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Open AccessArticle Organocatalytic Access to Enantioenriched Spirooxindole-Based 4-Methyleneazetidines
Molecules 2017, 22(11), 2016; https://doi.org/10.3390/molecules22112016
Received: 30 October 2017 / Revised: 15 November 2017 / Accepted: 17 November 2017 / Published: 21 November 2017
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Abstract
This work describes the synthesis of enantioenriched spiro compounds, incorporating the azetidine and the oxindole motifs. The preparation relies on a formal [2 + 2] annulation reaction of isatin-derived N-tert-butylsulfonyl ketimines with allenoates. The asymmetric induction is secured by an
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This work describes the synthesis of enantioenriched spiro compounds, incorporating the azetidine and the oxindole motifs. The preparation relies on a formal [2 + 2] annulation reaction of isatin-derived N-tert-butylsulfonyl ketimines with allenoates. The asymmetric induction is secured by an organocatalytic strategy, exploiting a bifunctional cinchona-type β-isocupridine-based catalyst. Some post-transformation products, including unexpected spiropyrroline and 3,3-disubstituted oxindole derivatives, are also presented. Full article
(This article belongs to the Special Issue Advances in Spiro Compounds)
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Open AccessFeature PaperReview Taxon- and Site-Specific Melatonin Catabolism
Molecules 2017, 22(11), 2015; https://doi.org/10.3390/molecules22112015
Received: 3 November 2017 / Revised: 20 November 2017 / Accepted: 20 November 2017 / Published: 21 November 2017
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Abstract
Melatonin is catabolized both enzymatically and nonenzymatically. Nonenzymatic processes mediated by free radicals, singlet oxygen, other reactive intermediates such as HOCl and peroxynitrite, or pseudoenzymatic mechanisms are not species- or tissue-specific, but vary considerably in their extent. Higher rates of nonenzymatic melatonin metabolism
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Melatonin is catabolized both enzymatically and nonenzymatically. Nonenzymatic processes mediated by free radicals, singlet oxygen, other reactive intermediates such as HOCl and peroxynitrite, or pseudoenzymatic mechanisms are not species- or tissue-specific, but vary considerably in their extent. Higher rates of nonenzymatic melatonin metabolism can be expected upon UV exposure, e.g., in plants and in the human skin. Additionally, melatonin is more strongly nonenzymatically degraded at sites of inflammation. Typical products are several hydroxylated derivatives of melatonin and N1-acetyl-N2-formyl-5-methoxykynuramine (AFMK). Most of these products are also formed by enzymatic catalysis. Considerable taxon- and site-specific differences are observed in the main enzymatic routes of catabolism. Formation of 6-hydroxymelatonin by cytochrome P450 subforms are prevailing in vertebrates, predominantly in the liver, but also in the brain. In pineal gland and non-mammalian retina, deacetylation to 5-methoxytryptamine (5-MT) plays a certain role. This pathway is quantitatively prevalent in dinoflagellates, in which 5-MT induces cyst formation and is further converted to 5-methoxyindole-3-acetic acid, an end product released to the water. In plants, the major route is catalyzed by melatonin 2-hydroxylase, whose product is tautomerized to 3-acetamidoethyl-3-hydroxy-5-methoxyindolin-2-one (AMIO), which exceeds the levels of melatonin. Formation and properties of various secondary products are discussed. Full article
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Open AccessArticle The Complete Chloroplast Genome Sequences of Aconitum pseudolaeve and Aconitum longecassidatum, and Development of Molecular Markers for Distinguishing Species in the Aconitum Subgenus Lycoctonum
Molecules 2017, 22(11), 2012; https://doi.org/10.3390/molecules22112012
Received: 31 October 2017 / Accepted: 19 November 2017 / Published: 21 November 2017
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Abstract
Aconitum pseudolaeve Nakai and Aconitum longecassidatum Nakai, which belong to the Aconitum subgenus Lycoctonum, are distributed in East Asia and Korea. Aconitum species are used in herbal medicine and contain highly toxic components, including aconitine. A. pseudolaeve, an endemic species of
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Aconitum pseudolaeve Nakai and Aconitum longecassidatum Nakai, which belong to the Aconitum subgenus Lycoctonum, are distributed in East Asia and Korea. Aconitum species are used in herbal medicine and contain highly toxic components, including aconitine. A. pseudolaeve, an endemic species of Korea, is a commercially valuable material that has been used in the manufacture of cosmetics and perfumes. Although Aconitum species are important plant resources, they have not been extensively studied, and genomic information is limited. Within the subgenus Lycoctonum, which includes A. pseudolaeve and A. longecassidatum, a complete chloroplast (CP) genome is available for only one species, Aconitum barbatum Patrin ex Pers. Therefore, we sequenced the complete CP genomes of two Aconitum species, A. pseudolaeve and A. longecassidatum, which are 155,628 and 155,524 bp in length, respectively. Both genomes have a quadripartite structure consisting of a pair of inverted repeated regions (51,854 and 52,108 bp, respectively) separated by large single-copy (86,683 and 86,466 bp) and small single-copy (17,091 and 16,950 bp) regions similar to those in other Aconitum CP genomes. Both CP genomes consist of 112 unique genes, 78 protein-coding genes, 4 ribosomal RNA (rRNA) genes, and 30 transfer RNA (tRNA) genes. We identified 268 and 277 simple sequence repeats (SSRs) in A. pseudolaeve and A. longecassidatum, respectively. We also identified potential 36 species-specific SSRs, 53 indels, and 62 single-nucleotide polymorphisms (SNPs) between the two CP genomes. Furthermore, a comparison of the three Aconitum CP genomes from the subgenus Lycoctonum revealed highly divergent regions, including trnK-trnQ, ycf1-ndhF, and ycf4-cemA. Based on this finding, we developed indel markers using indel sequences in trnK-trnQ and ycf1-ndhF. A. pseudolaeve, A. longecassidatum, and A. barbatum could be clearly distinguished using the novel indel markers AcoTT (Aconitum trnK-trnQ) and AcoYN (Aconitum ycf1-ndhF). These two new complete CP genomes provide useful genomic information for species identification and evolutionary studies of the Aconitum subgenus Lycoctonum. Full article
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Open AccessArticle Optimization of Goat Milk with ACE Inhibitory Peptides Fermented by Lactobacillus bulgaricus LB6 Using Response Surface Methodology
Molecules 2017, 22(11), 2001; https://doi.org/10.3390/molecules22112001
Received: 20 October 2017 / Accepted: 15 November 2017 / Published: 21 November 2017
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Abstract
In the present study, the incubation conditions of goat milk fermented by Lactobacillus bulgaricus LB6 were optimized to increase the angiotensin converting enzyme (ACE, EC 3.4.15.1) inhibitory activity by Box–Behnken design of response surface methodology. Incubation temperature, whey powder, and calcium lactate had
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In the present study, the incubation conditions of goat milk fermented by Lactobacillus bulgaricus LB6 were optimized to increase the angiotensin converting enzyme (ACE, EC 3.4.15.1) inhibitory activity by Box–Behnken design of response surface methodology. Incubation temperature, whey powder, and calcium lactate had significant effects on ACE inhibition rate and viable counts of LB6 during incubation. The results showed that optimal conditions of fermentation were found to be 37.05 °C, 0.8% (w/w) whey powder and 0.50% (w/w) calcium lactate. ACE inhibition rate increased significantly from 71.04 ± 0.37% to 83.31 ± 0.45% and the viable counts of Lactobacillus bulgaricus LB6 reached to 8.03 × 107 cfu·mL−1 under the optimal conditions, which approached the predicted values 83.25% and 8.04 × 107 cfu·mL−1. The optimal fermentation conditions can be a good reference for preparing ACE inhibitory peptides from goat milk. Full article
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Open AccessArticle Antimalarial Activity of Acetylenic Thiophenes from Echinops hoehnelii Schweinf
Molecules 2017, 22(11), 1965; https://doi.org/10.3390/molecules22111965
Received: 6 October 2017 / Accepted: 11 November 2017 / Published: 21 November 2017
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Abstract
Malaria is one of the world’s most severe endemic diseases and due to the emergence of resistance to the currently available medicines, the need for new targets and relevant antimalarial drugs remains acute. The crude extract, four solvent fractions and two isolated compounds
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Malaria is one of the world’s most severe endemic diseases and due to the emergence of resistance to the currently available medicines, the need for new targets and relevant antimalarial drugs remains acute. The crude extract, four solvent fractions and two isolated compounds from the roots of Echinops hoehnelii were tested for their antimalarial activity using the standard four-day suppressive method in Plasmodium berghei-infected mice. The 80% methanol extract exhibited suppression of 4.6%, 27.8%, 68.5% and 78.7% at dose of 50, 100, 200 and 400 mg/kg respectively. The dichloromethane fraction displayed chemosuppression of 24.9, 33.5 and 43.0% dose of 100, 200 and 400 mg/kg of body weight. Five acetylenicthiophenes were isolated from the dichloromethane fraction of which 5-(penta-1,3-diynyl)-2-(3,4-dihydroxybut-1-ynyl)-thiophene decreased the level of parasitaemia by 43.2% and 50.2% while 5-(penta-1,3-diynyl)-2-(3-chloro-4-acetoxy-but-1-yn)-thiophene suppressed by 18.8% and 32.7% at 50 and 100 mg/kg, respectively. The study confirmed the traditional claim of the plant to treat malaria and could be used as a new lead for the development of antimalarial drugs. Full article
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Open AccessArticle Inhibition of bcl-2 and cox-2 Protein Expression after Local Application of a New Carmustine-Loaded Clinoptilolite-Based Delivery System in a Chemically Induced Skin Cancer Model in Mice
Molecules 2017, 22(11), 2014; https://doi.org/10.3390/molecules22112014
Received: 27 September 2017 / Revised: 19 November 2017 / Accepted: 6 November 2017 / Published: 20 November 2017
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Abstract
Our research has focused on in vitro and in vivo evaluations of a new Carmustine (BCNU)-loaded clinoptilolite-based delivery system. Two clinoptilolite ionic forms—hydrogen form (HCLI) and sodium form (NaCLI)—were prepared, allowing a loading degree of about 5–6 mg BCNU/g of zeolite matrix due
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Our research has focused on in vitro and in vivo evaluations of a new Carmustine (BCNU)-loaded clinoptilolite-based delivery system. Two clinoptilolite ionic forms—hydrogen form (HCLI) and sodium form (NaCLI)—were prepared, allowing a loading degree of about 5–6 mg BCNU/g of zeolite matrix due to the dual porous feature of clinoptilolite. Clinoptilolite-based delivery systems released 35.23% of the load in 12 h for the BCNU@HCLI system and only 10.82% for the BCNU@NaCLI system. The BCNU@HCLI system was chosen to develop gel and cream semisolid dosage forms. The cream (C_BCNU@HCLI) released 29.6% of the loaded BCNU after 12 h in the Nylon synthetic membrane test and 31.6% in the collagen membrane test, higher by comparison to the gel. The new cream was evaluated in vivo in a chemically induced model of skin cancer in mice. Quantitative immunohistochemistry analysis showed stronger inhibition of B-cell lymphoma-2 (bcl-2) and cyclooxygenase 2 (cox-2) protein expression, known markers for cancer survival and aggressiveness, after the treatment with C_BCNU@HCLI by comparison to all the control treatment types, including an off-label magistral formula commercially available Carmustine cream as reference, bringing evidence that a clinoptilolite-based delivery systems could be used as a cancer drug carriers and controlled release systems (skin-targeted topical delivery systems). Full article
(This article belongs to the Section Medicinal Chemistry)
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Open AccessArticle Anti-Bacterial and Microecosystem-Regulating Effects of Dental Implant Coated with Dimethylaminododecyl Methacrylate
Molecules 2017, 22(11), 2013; https://doi.org/10.3390/molecules22112013
Received: 25 October 2017 / Accepted: 15 November 2017 / Published: 20 November 2017
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Abstract
The effects of dimethylaminododecyl methacrylate (DMADDM) modified titanium implants on bacterial activity and microbial ecosystem of saliva-derived biofilm were investigated for the first time. Titanium discs were coated with DMADDM solutions at mass fractions of 0 mg/mL (control), 1, 5 and 10 mg/mL,
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The effects of dimethylaminododecyl methacrylate (DMADDM) modified titanium implants on bacterial activity and microbial ecosystem of saliva-derived biofilm were investigated for the first time. Titanium discs were coated with DMADDM solutions at mass fractions of 0 mg/mL (control), 1, 5 and 10 mg/mL, respectively. Biomass accumulation and metabolic activity of biofilms were tested using crystal violet assay and MTT (3-(4,5-Dimethyl-thiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay. 16S rRNA gene sequencing was performed to measure the microbial community. Live/dead staining and scanning electron microscopy (SEM) were used to value the structure of biofilm. The results showed that the higher mass fraction of DMADDM the coating solution had, the significantly lower the values of metabolic activity and accumulated biofilms got, as well as fewer live cells and less extracellular matrix. Moreover, 5 mg/mL of DMADDM was the most effective concentration, as well as 10 mg/mL. In microecosystem-regulation, the DMADDM modified titanium implant decreased the relative abundance of Neisseria and Actinomyces and increased the relative abundance of Lactobacillus, a probiotic for peri-implant diseases. In conclusion, via inhibiting growth and regulating microecosystem of biofilm, this novel titanium implant coating with DMADDM was promising in preventing peri-implant disease in an ‘ecological manner’. Full article
(This article belongs to the Special Issue Antibacterial Materials and Coatings)
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Open AccessArticle Comparison of the Chemical Profiles and Antioxidant Activities of Different Parts of Cultivated Cistanche deserticola Using Ultra Performance Liquid Chromatography-Quadrupole Time-of-Flight Mass Spectrometry and a 1,1-Diphenyl-2-picrylhydrazyl-Based Assay
Molecules 2017, 22(11), 2011; https://doi.org/10.3390/molecules22112011
Received: 16 October 2017 / Revised: 10 November 2017 / Accepted: 16 November 2017 / Published: 20 November 2017
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Abstract
In this study, a sensitive ultra-performance liquid chromatography-photodiode array coupled to quadruple time-of-flight mass (UPLC-PDA-Q/TOF-MS) method and a 1,1-diphenyl-2- picrylhydrazyl (DPPH)-based assay were used to determine the chemical constituents and screen the antioxidant activity profiles of the methanol extracts of different parts of
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In this study, a sensitive ultra-performance liquid chromatography-photodiode array coupled to quadruple time-of-flight mass (UPLC-PDA-Q/TOF-MS) method and a 1,1-diphenyl-2- picrylhydrazyl (DPPH)-based assay were used to determine the chemical constituents and screen the antioxidant activity profiles of the methanol extracts of different parts of cultivated Cistanche deserticola (C. deserticola). First, qualitative and quantitative chemical composition analyses of the different parts of cultivated C. deserticola were conducted. Obvious differences were observed between the chemical profiles and content distribution of phenylethanoid glycosides (PhGs) from the different cultivated C. deserticola parts. The average contents of the six PhGs parts varied from 4.91 to 72.56 mg/g DW (milligrams of extract per gram of plant dry weight) in the six different parts of Cistanche deserticola, displaying a significant decreasing trend from the bottom to the top of cultivated C. deserticola and the highest content in the stems. From the bottom to the top of the plant, the echinacoside and cistanoside A content decreased and the 2 -acetylacteoside content increased. Second, an offline DPPH assay revealed that the total scavenging activities of all parts within the range of 20–500 μ g/mL increased in a concentration-dependent manner and that good antioxidant activities were found in all plant parts, particularly in the stems, which could be related to their higher PhG content. Additionally, a DPPH-UPLC-PDA method was successfully applied to rapidly screen the antioxidant profiles and antioxidant components of the different cultivated C. deserticola parts. According to the antioxidant profiles before and after the DPPH reaction, there were wide variations in the antioxidant activities of different cultivated C. deserticola parts. Moreover, the antioxidant profiles revealed the presence of major free radical scavengers identified as PhGs using UPLC-Q/TOF-MS. Finally, the established DPPH-UPLC-PDA method was reagent saving, rapid and feasible for correlating the chemical profile of traditional chinese medicines (TCMs) with their bioactivities without isolation and purification and may be used for multicomponent analysis of active substances in other foods and herbs. Therefore, to better harness C. deserticola resources, using this method to evaluate cultivated C. deserticola, a promising herb material with obvious antioxidant activity, is crucial. Full article
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Open AccessArticle Synthesis and Improved Cross-Linking Properties of C5-Modified Furan Bearing PNAs
Molecules 2017, 22(11), 2010; https://doi.org/10.3390/molecules22112010
Received: 21 October 2017 / Revised: 7 November 2017 / Accepted: 9 November 2017 / Published: 20 November 2017
Cited by 2 | PDF Full-text (2070 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Over the past decades, peptide nucleic acid/DNA (PNA:DNA) duplex stability has been improved via backbone modification, often achieved via introducing an amino acid side chain at the α- or γ-position in the PNA sequence. It was previously shown that interstrand cross-linking can further
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Over the past decades, peptide nucleic acid/DNA (PNA:DNA) duplex stability has been improved via backbone modification, often achieved via introducing an amino acid side chain at the α- or γ-position in the PNA sequence. It was previously shown that interstrand cross-linking can further enhance the binding event. In this work, we combined both strategies to fine-tune PNA crosslinking towards single stranded DNA sequences using a furan oxidation-based crosslinking method; for this purpose, γ-l-lysine and γ-l-arginine furan-PNA monomers were synthesized and incorporated in PNA sequences via solid phase synthesis. It was shown that the l-lysine γ-modification had a beneficial effect on crosslink efficiency due to pre-organization of the PNA helix and a favorable electrostatic interaction between the positively-charged lysine and the negatively-charged DNA backbone. Moreover, the crosslink yield could be optimized by carefully choosing the type of furan PNA monomer. This work is the first to describe a selective and biocompatible furan crosslinking strategy for crosslinking of γ-modified PNA sequences towards single-stranded DNA. Full article
(This article belongs to the Special Issue Molecular Properties and the Applications of Peptide Nucleic Acids)
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