Molecules

3907 KiB

Open AccessArticle

Synthesis, Spectroscopic, Structural and Quantum Chemical Studies of a New Imine Oxime and Its Palladium(II) Complex: Hydrolysis Mechanism

by Yunus Kaya, Veysel T. Yilmaz and Orhan Buyukgungor

Molecules 2016, 21(1), 52; https://doi.org/10.3390/molecules21010052 - 21 Jan 2016

Cited by 12 | Viewed by 8013

Abstract

In this work, we report synthesis, crystallographic, spectroscopic and quantum chemical studies of a new imine oxime, namely (4-nitro-phenyl)-(1-phenyl-ethylimino)-acetaldehyde oxime (nppeieoH). Spectroscopic and X-ray diffraction studies showed that nppeieoH is hydrolyzed in aqueous solution, forming nitroisonitrosoacetophenone (ninap) and the hydrolysis product binds to [...] Read more.

In this work, we report synthesis, crystallographic, spectroscopic and quantum chemical studies of a new imine oxime, namely (4-nitro-phenyl)-(1-phenyl-ethylimino)-acetaldehyde oxime (nppeieoH). Spectroscopic and X-ray diffraction studies showed that nppeieoH is hydrolyzed in aqueous solution, forming nitroisonitrosoacetophenone (ninap) and the hydrolysis product binds to Pd(II) to yield [Pd(nppeieo)(ninap)]. The mechanism of the hydrolysis reaction has been theoretically investigated in detail, using density functional theory (DFT) with the B3LYP method. The vibrational and the electronic spectra of nppeieoH and its Pd(II) complex, the HOMO and LUMO analysis, Mulliken atomic charges and molecular electrostatic potential were also performed. The predicted nonlinear optical properties of both compounds are higher than those of urea. Full article

(This article belongs to the Section Molecular Diversity)

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765 KiB

Open AccessEditorial

Acknowledgement to Reviewers of Molecules in 2015

by Molecules Editorial Office

Molecules 2016, 21(1), 131; https://doi.org/10.3390/molecules21010131 - 21 Jan 2016

Cited by 1 | Viewed by 7985

Abstract

The editors of Molecules would like to express their sincere gratitude to the following reviewers for assessing manuscripts in 2015. [...] Full article

153 KiB

Open AccessCorrection

Correction: Hasan, I., et al. A Galactose-Binding Lectin Isolated from Aplysia kurodai (Sea Hare) Eggs Inhibits Streptolysin-Induced Hemolysis. Molecules 2014, 19, 13990–14003

by Imtiaj Hasan, Miharu Watanabe, Naoto Ishizaki, Yoshiko Sugita-Konishi, Yasushi Kawakami, Jun Suzuki, Chikaku Dogasaki, Sultana Rajia, Sarkar M. A. Kawsar, Yasuhiro Koide, Robert A. Kanaly, Shigeki Sugawara, Masahiro Hosono, Yukiko Ogawa, Yuki Fujii, Hideyuki Iriko, Jiharu Hamako, Taei Matsui and Yasuhiro Ozeki

Molecules 2016, 21(1), 129; https://doi.org/10.3390/molecules21010129 - 21 Jan 2016

Viewed by 4615

Abstract

The authors wish to make the following correction to their paper [1]. [...] Full article

(This article belongs to the Special Issue Lectins)

2135 KiB

Open AccessArticle

Pharmacokinetics of Tyrosol Metabolites in Rats

by Da-Hye Lee, Yang-Ji Kim, Min Jung Kim, Jiyun Ahn, Tae-Youl Ha, Sang Hee Lee, Young Jin Jang and Chang Hwa Jung

Molecules 2016, 21(1), 128; https://doi.org/10.3390/molecules21010128 - 21 Jan 2016

Cited by 20 | Viewed by 6939

Abstract

Tyrosol is considered a potential antioxidant; however, little is known regarding the pharmacokinetics of its metabolites. To study the pharmacokinetics of tyrosol-derived metabolites after oral administration of a single dose of tyrosol, we attempted to identify tyrosol metabolites in rat plasma by using [...] Read more.

Tyrosol is considered a potential antioxidant; however, little is known regarding the pharmacokinetics of its metabolites. To study the pharmacokinetics of tyrosol-derived metabolites after oral administration of a single dose of tyrosol, we attempted to identify tyrosol metabolites in rat plasma by using ultra-performance liquid chromatography and quadrupole time-of-flight mass spectrometry (UPLC-Q-TOF-MS). Two tyrosol metabolites (M1 and M2) were detected in the plasma. M1 was identified as tyrosol-4-sulfate (T4S) with an [M − H]⁻ ion at m/z 217. While M2 showed an [M − H]⁻ ion at m/z 151.0, its metabolite was not identified. Pharmacokinetic analysis of T4S and M2 showed rapid uptake after oral administration of tyrosol within 1 h. The metabolites were rapidly distributed in most organs and tissues and eliminated within 4 h. The greatest T4S deposition by tissue weight was observed in the liver, followed by the kidney and spleen, while M2 was most concentrated in the kidney followed by the liver and spleen. These findings indicate that T4S and M2 were distributed mainly in tissues with an abundant blood supply and were rapidly excreted in urine. Full article

(This article belongs to the Section Metabolites)

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874 KiB

Open AccessCommunication

The Scavenging of DPPH, Galvinoxyl and ABTS Radicals by Imine Analogs of Resveratrol

by Peter Kotora, František Šeršeň, Juraj Filo, Dušan Loos, Juraj Gregáň and Fridrich Gregáň

Molecules 2016, 21(1), 127; https://doi.org/10.3390/molecules21010127 - 21 Jan 2016

Cited by 50 | Viewed by 7535

Abstract

Resveratrol (3,5,4′-trihydroxystilbene) is a phytoalexin produced by plants. Resveratrol is known for its anti-cancer, antiviral and antioxidant properties. We prepared imine analogs of resveratrol ((hydroxyphenyliminomethyl)phenols) and tested their antioxidant activity. All prepared resveratrol analogs were able to scavenge 2,2-diphenyl-1-picrylhydrazyl (DPPH), galvinoxyl radical (GOR) [...] Read more.

Resveratrol (3,5,4′-trihydroxystilbene) is a phytoalexin produced by plants. Resveratrol is known for its anti-cancer, antiviral and antioxidant properties. We prepared imine analogs of resveratrol ((hydroxyphenyliminomethyl)phenols) and tested their antioxidant activity. All prepared resveratrol analogs were able to scavenge 2,2-diphenyl-1-picrylhydrazyl (DPPH), galvinoxyl radical (GOR) and 2,2′-azino-bis(3-ethylbenzothiazoline)-6-sulphonic acid (ABTS) radicals. The antioxidant activity efficiency correlated with the number and position of hydroxyl groups. The most effective antioxidants were resveratrol analogs containing three hydroxyl groups in the benzylidene part of their molecules. These results provide new insights into the relationship between the chemical structure and biological activity of resveratrol analogs. Full article

(This article belongs to the Section Natural Products Chemistry)

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Open AccessArticle

Serum Metabolomic Characterization of Liver Fibrosis in Rats and Anti-Fibrotic Effects of Yin-Chen-Hao-Tang

by Hongyang Zhang, Xiaoning Wang, Ping Hu, Wenjun Zhou, Min Zhang, Jia Liu, Yuerong Wang, Ping Liu and Guoan Luo

Molecules 2016, 21(1), 126; https://doi.org/10.3390/molecules21010126 - 21 Jan 2016

Cited by 27 | Viewed by 6985

Abstract

Yin-Chen-Hao-Tang (YCHT) is a famous Chinese medicine formula which has long been used in clinical practice for treating various liver diseases, such as liver fibrosis. However, to date, the mechanism for its anti-fibrotic effects remains unclear. In this paper, an ultra-performance liquid chromatography-time-of-flight [...] Read more.

Yin-Chen-Hao-Tang (YCHT) is a famous Chinese medicine formula which has long been used in clinical practice for treating various liver diseases, such as liver fibrosis. However, to date, the mechanism for its anti-fibrotic effects remains unclear. In this paper, an ultra-performance liquid chromatography-time-of-flight mass spectrometry (UPLC-TOF-MS)-based metabolomic study was performed to characterize dimethylnitrosamine (DMN)-induced liver fibrosis in rats and evaluate the therapeutic effects of YCHT. Partial least squares-discriminant analysis (PLS-DA) showed that the model group was well separated from the control group, whereas the YCHT-treated group exhibited a tendency to restore to the controls. Seven significantly changed fibrosis-related metabolites, including unsaturated fatty acids and lysophosphatidylcholines (Lyso-PCs), were identified. Moreover, statistical analysis demonstrated that YCHT treatment could reverse the levels of most metabolites close to the normal levels. These results, along with histological and biochemical examinations, indicate that YCHT has anti-fibrotic effects, which may be due to the suppression of oxidative stress and resulting lipid peroxidation involved in hepatic fibrogenesis. This study offers new opportunities to improve our understanding of liver fibrosis and the anti-fibrotic mechanisms of YCHT. Full article

(This article belongs to the Section Metabolites)

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308 KiB

Open AccessCorrection

Correction: Yan, R.Y., et al. HPLC-DPPH Screening Method for Evaluation of Antioxidant Compounds Extracted from Semen Oroxyli. Molecules 2014, 19, 4409–4417

by Renyi Yan, Yangyang Cao and Bin Yang

Molecules 2016, 21(1), 125; https://doi.org/10.3390/molecules21010125 - 21 Jan 2016

Viewed by 3667

Abstract

The authors wish to inform readers that there is an error in the chemical structures shown in Figure 4 of this paper [1]. [...] Full article

(This article belongs to the Section Natural Products Chemistry)

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Figure 4

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Open AccessArticle

Synthesis of Some Novel 2-Amino-5-arylazothiazole Disperse Dyes for Dyeing Polyester Fabrics and Their Antimicrobial Activity

by Hatem E. Gaffer, Moustafa M. G. Fouda and Mohamed E. Khalifa

Molecules 2016, 21(1), 122; https://doi.org/10.3390/molecules21010122 - 21 Jan 2016

Cited by 38 | Viewed by 5793

Abstract

The present work describes the synthesis of a series of four novel biologically active 2-amino-5-arylazothiazole disperse dyes containing the sulfa drug nucleus. The structures of the synthesized thiazole derivatives are confirmed using UV-spectrophotometry, infrared and nuclear magnetic resonance techniques and elemental analysis. The [...] Read more.

The present work describes the synthesis of a series of four novel biologically active 2-amino-5-arylazothiazole disperse dyes containing the sulfa drug nucleus. The structures of the synthesized thiazole derivatives are confirmed using UV-spectrophotometry, infrared and nuclear magnetic resonance techniques and elemental analysis. The synthesized dyes are applied to polyester fabrics as disperse dyes and their fastness properties to washing, perspiration, rubbing, sublimation, and light are evaluated. The synthesized compounds exhibit promising biological efficiency against selected Gram-positive and Gram-negative pathogenic bacteria as well as fungi. Full article

(This article belongs to the Collection Heterocyclic Compounds)

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Open AccessArticle

On-Line Organic Solvent Field Enhanced Sample Injection in Capillary Zone Electrophoresis for Analysis of Quetiapine in Beagle Dog Plasma

by Yuqing Cao, Jun Wen, Tingting Zhou and Guorong Fan

Molecules 2016, 21(1), 121; https://doi.org/10.3390/molecules21010121 - 21 Jan 2016

Cited by 7 | Viewed by 7356

Abstract

A rapid and sensitive capillary zone electrophoresis (CZE) method with field enhanced sample injection (FESI) was developed and validated for the determination of quetiapine fumarate in beagle dog plasma, with a sample pretreatment by LLE in 96-well deep format plate. The optimum separation [...] Read more.

A rapid and sensitive capillary zone electrophoresis (CZE) method with field enhanced sample injection (FESI) was developed and validated for the determination of quetiapine fumarate in beagle dog plasma, with a sample pretreatment by LLE in 96-well deep format plate. The optimum separation was carried out in an uncoated 31.2 cm × 75 μm fused-silica capillary with an applied voltage of 13 kV. The electrophoretic analysis was performed by 50 mM phosphate at pH 2.5. The detection wavelength was 210 nm. Under these optimized conditions, FESI with acetonitrile enhanced the sensitivity of quetiapine about 40–50 folds in total. The method was suitably validated with respect to stability, specificity, linearity, lower limit of quantitation, accuracy, precision and extraction recovery. Using mirtazapine as an internal standard (100 ng/mL), the response of quetiapine was linear over the range of 1–1000 ng/mL. The lower limit of quantification was 1 ng/mL. The intra- and inter-day precisions for the assay were within 4.8% and 12.7%, respectively. The method represents the first application of FESI-CZE to the analysis of quetiapine fumarate in beagle dog plasma after oral administration. Full article

(This article belongs to the Section Medicinal Chemistry)

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Open AccessArticle

Cytotoxic Compounds from Juglans sinensis Dode Display Anti-Proliferative Activity by Inducing Apoptosis in Human Cancer Cells

by Yoo Jin Lee, Jun Cui, Jun Lee, Ah-Reum Han, Eun Byul Lee, Ho Hee Jang and Eun Kyoung Seo

Molecules 2016, 21(1), 120; https://doi.org/10.3390/molecules21010120 - 21 Jan 2016

Cited by 16 | Viewed by 8253

Abstract

Phytochemical investigation of the bark of Juglans sinensis Dode (Juglandaceae) led to the isolation of two active compounds, 8-hydroxy-2-methoxy-1,4-naphthoquinone (1) and 5-hydroxy-2-methoxy-1,4-naphthoquinone (2), together with 15 known compounds 3–17. All compounds were isolated from this plant [...] Read more.

Phytochemical investigation of the bark of Juglans sinensis Dode (Juglandaceae) led to the isolation of two active compounds, 8-hydroxy-2-methoxy-1,4-naphthoquinone (1) and 5-hydroxy-2-methoxy-1,4-naphthoquinone (2), together with 15 known compounds 3–17. All compounds were isolated from this plant for the first time. The structures of 1 and 2 were elucidated by spectroscopic data analysis, including 1D and 2D NMR experiments. Compounds 1–17 were tested for their cytotoxicity against the A549 human lung cancer cell line; compounds 1 and 2 exhibited significant cytotoxicity and additionally had potent cytotoxicity against six human cancer cell lines, MCF7 (breast cancer), SNU423 (liver cancer), SH-SY5Y (neuroblastoma), HeLa (cervical cancer), HCT116 (colorectal cancer), and A549 (lung cancer). In particular, breast, colon, and lung cancer cells were more sensitive to the treatment using compound 1. In addition, compounds 1 and 2 showed strong cytotoxic activity towards human breast cancer cells MCF7, HS578T, and T47D, but not towards MCF10A normal-like breast cells. They also inhibited the colony formation of MCF7, A549, and HCT116 cells in a dose-dependent manner. Flow cytometry analysis revealed that the percentage of apoptotic cells significantly increased in MCF7 cells upon the treatment with compounds 1 and 2. The mechanism of cell death caused by compounds 1 and 2 may be attributed to the upregulation of Bax and downregulation of Bcl2. These findings suggest that compounds 1 and 2 may be regarded as potential therapeutic agents against cancer. Full article

(This article belongs to the Section Natural Products Chemistry)

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1365 KiB

Open AccessArticle

Antiproliferative and Antioxidant Activities and Mycosporine-Like Amino Acid Profiles of Wild-Harvested and Cultivated Edible Canadian Marine Red Macroalgae

by Yasantha Athukorala, Susan Trang, Carmen Kwok and Yvonne V. Yuan

Molecules 2016, 21(1), 119; https://doi.org/10.3390/molecules21010119 - 21 Jan 2016

Cited by 53 | Viewed by 8922

Abstract

Antiproliferative and antioxidant activities and mycosporine-like amino acid (MAA) profiles of methanol extracts from edible wild-harvested (Chondrus crispus, Mastocarpus stellatus, Palmaria palmata) and cultivated (C. crispus) marine red macroalgae were studied herein. Palythine, asterina-330, shinorine, palythinol, porphyra-334 [...] Read more.

Antiproliferative and antioxidant activities and mycosporine-like amino acid (MAA) profiles of methanol extracts from edible wild-harvested (Chondrus crispus, Mastocarpus stellatus, Palmaria palmata) and cultivated (C. crispus) marine red macroalgae were studied herein. Palythine, asterina-330, shinorine, palythinol, porphyra-334 and usujirene MAAs were identified in the macroalgal extracts by LC/MS/MS. Extract reducing activity rankings were (p < 0.001): wild P. palmata > cultivated C. crispus = wild M. stellatus > wild low-UV C. crispus > wild high-UV C. crispus; whereas oxygen radical absorbance capacities were (p < 0.001): wild M. stellatus > wild P. palmata > cultivated C. crispus > wild low-UV C. crispus > wild high-UV C. crispus. Extracts were antiproliferative against HeLa and U-937 cells (p < 0.001) from 0.125–4 mg/mL, 24 h. Wild P. palmata and cultivated C. crispus extracts increased (p < 0.001) HeLa caspase-3/7 activities and the proportion of cells arrested at Sub G₁ (apoptotic) compared to wild-harvested C. crispus and M. stellatus extracts. HeLa cells incubated with wild P. palmata and cultivated C. crispus extracts also exhibited morphological changes characteristic of apoptosis (shrinkage, rounding). Thus, extracts rich in low-polarity usujirene and polar palythine and asterina-330 MAAs were antiproliferative as inducers of apoptosis in HeLa cells. Full article

(This article belongs to the Special Issue Antioxidants—A Risk-Benefit Analysis for Health)

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Open AccessArticle

A Rapid Screening Analysis of Antioxidant Compounds in Native Australian Food Plants Using Multiplexed Detection with Active Flow Technology Columns

by Emmanuel Janaka Rochana Rupesinghe, Andrew Jones, Ross Andrew Shalliker and Sercan Pravadali-Cekic

Molecules 2016, 21(1), 118; https://doi.org/10.3390/molecules21010118 - 20 Jan 2016

Cited by 15 | Viewed by 5453

Abstract

Conventional techniques for identifying antioxidant and phenolic compounds in native Australian food plants are laborious and time-consuming. Here, we present a multiplexed detection technique that reduces analysis time without compromising separation performance. This technique is achieved using Active Flow Technology-Parallel Segmented Flow (AFT-PSF) [...] Read more.

Conventional techniques for identifying antioxidant and phenolic compounds in native Australian food plants are laborious and time-consuming. Here, we present a multiplexed detection technique that reduces analysis time without compromising separation performance. This technique is achieved using Active Flow Technology-Parallel Segmented Flow (AFT-PSF) columns. Extracts from cinnamon myrtle (Backhousia myrtifolia) and lemon myrtle (Backhousia citriodora) leaves were analysed via multiplexed detection using an AFT-PSF column with underivatised UV-VIS, mass spectroscopy (MS), and the 2,2-diphenyl-1-picrylhydrazyl (DPPH^•) derivatisation for antioxidants as detection methods. A number of antioxidant compounds were detected in the extracts of each leaf extract. Full article

(This article belongs to the Section Natural Products Chemistry)

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Open AccessReview

NHC Backbone Configuration in Ruthenium-Catalyzed Olefin Metathesis

by Veronica Paradiso, Chiara Costabile and Fabia Grisi

Molecules 2016, 21(1), 117; https://doi.org/10.3390/molecules21010117 - 20 Jan 2016

Cited by 29 | Viewed by 7125

Abstract

The catalytic properties of olefin metathesis ruthenium complexes bearing N-heterocyclic carbene ligands with stereogenic centers on the backbone are described. Differences in catalytic behavior depending on the backbone configurations of symmetrical and unsymmetrical NHCs are discussed. In addition, an overview on asymmetric [...] Read more.

The catalytic properties of olefin metathesis ruthenium complexes bearing N-heterocyclic carbene ligands with stereogenic centers on the backbone are described. Differences in catalytic behavior depending on the backbone configurations of symmetrical and unsymmetrical NHCs are discussed. In addition, an overview on asymmetric olefin metathesis promoted by chiral catalysts bearing C₂-symmetric and C₁-symmetric NHCs is provided. Full article

(This article belongs to the Special Issue Olefin Metathesis)

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Open AccessArticle

Skin Delivery and in Vitro Biological Evaluation of Trans-Resveratrol-Loaded Solid Lipid Nanoparticles for Skin Disorder Therapies

by Roberta B. Rigon, Naiara Fachinetti, Patrícia Severino, Maria H. A. Santana and Marlus Chorilli

Molecules 2016, 21(1), 116; https://doi.org/10.3390/molecules21010116 - 20 Jan 2016

Cited by 87 | Viewed by 8569

Abstract

The aim of this study was to evaluate the skin delivery and in vitro biological activity of trans-resveratrol (RES)-loaded solid lipid nanoparticles (SLNs). The SLNs were composed of stearic acid, poloxamer 407, soy phosphatidylcholine (SPC), an aqueous phase and 0.1% RES. The [...] Read more.

The aim of this study was to evaluate the skin delivery and in vitro biological activity of trans-resveratrol (RES)-loaded solid lipid nanoparticles (SLNs). The SLNs were composed of stearic acid, poloxamer 407, soy phosphatidylcholine (SPC), an aqueous phase and 0.1% RES. The particle size, polydispersity index (PdI) and zeta potential were analyzed by dynamic light scattering (DLS). The SLNs were analyzed by scanning electron microscopy (SEM-FEG) and differential scanning calorimetry (DSC). In vitro RES-SLN skin permeation/retention assays were conducted, and their tyrosinase inhibitory activity was evaluated. An MTT reduction assay was performed on HaCat keratinocytes to determine in vitro cytotoxicity. The formulations had average diameter lower than 200 nm, the addition of SPC promoted increases in PdI in the RES-SLNs, but decreases PdI in the RES-free SLNs and the formulations exhibited zeta potentials smaller than −3 mV. The DSC analysis of the SLNs showed no endothermic peak attributable to RES. Microscopic analysis suggests that the materials formed had nanometric size distribution. Up to 45% of the RES permeated through the skin after 24 h. The RES-loaded SLNs were more effective than kojic acid at inhibiting tyrosinase and proved to be non-toxic in HaCat keratinocytes. The results suggest that the investigated RES-loaded SLNs have potential use in skin disorder therapies. Full article

(This article belongs to the Special Issue Pharmaceutical Nanotechnology: Novel Approaches)

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6193 KiB

Open AccessArticle

Biocompatible 3D Matrix with Antimicrobial Properties

by Alberto Ion, Ecaterina Andronescu, Dragoș Rădulescu, Marius Rădulescu, Florin Iordache, Bogdan Ștefan Vasile, Adrian Vasile Surdu, Madalina Georgiana Albu, Horia Maniu, Mariana Carmen Chifiriuc, Alexandru Mihai Grumezescu and Alina Maria Holban

Molecules 2016, 21(1), 115; https://doi.org/10.3390/molecules21010115 - 20 Jan 2016

Cited by 7 | Viewed by 6438

Abstract

The aim of this study was to develop, characterize and assess the biological activity of a new regenerative 3D matrix with antimicrobial properties, based on collagen (COLL), hydroxyapatite (HAp), β-cyclodextrin (β-CD) and usnic acid (UA). The prepared 3D matrix was characterized by Scanning [...] Read more.

The aim of this study was to develop, characterize and assess the biological activity of a new regenerative 3D matrix with antimicrobial properties, based on collagen (COLL), hydroxyapatite (HAp), β-cyclodextrin (β-CD) and usnic acid (UA). The prepared 3D matrix was characterized by Scanning Electron Microscopy (SEM), Fourier Transform Infrared Microscopy (FT-IRM), Transmission Electron Microscopy (TEM), and X-ray Diffraction (XRD). In vitro qualitative and quantitative analyses performed on cultured diploid cells demonstrated that the 3D matrix is biocompatible, allowing the normal development and growth of MG-63 osteoblast-like cells and exhibited an antimicrobial effect, especially on the Staphylococcus aureus strain, explained by the particular higher inhibitory activity of usnic acid (UA) against Gram positive bacterial strains. Our data strongly recommend the obtained 3D matrix to be used as a successful alternative for the fabrication of three dimensional (3D) anti-infective regeneration matrix for bone tissue engineering. Full article

(This article belongs to the Special Issue Pharmaceutical Nanotechnology: Novel Approaches)

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2260 KiB

Open AccessArticle

Synthesis, Biological Evaluation and Molecular Docking of Certain Sulfones as Potential Nonazole Antifungal Agents

by Mohamed Fares, Mohamed A. Said, Muhammad A. Alsherbiny, Radwa A. Eladwy, Hadia Almahli, Marwa M. Abdel-Aziz, Hazem A. Ghabbour, Wagdy M. Eldehna and Hatem A. Abdel-Aziz

Molecules 2016, 21(1), 114; https://doi.org/10.3390/molecules21010114 - 20 Jan 2016

Cited by 16 | Viewed by 5920

Abstract

We reported herein the synthesis, antifungal activity, docking and in silico ADME prediction studies of four novel series of sulfones 6a–f, 8a–c, 10a–f and 12a–c. All the newly synthesized sulfones were tested [...] Read more.

We reported herein the synthesis, antifungal activity, docking and in silico ADME prediction studies of four novel series of sulfones 6a–f, 8a–c, 10a–f and 12a–c. All the newly synthesized sulfones were tested against four strains of Candida (including fluconazole-resistant Candida), two strains of Aspergillus, two dermatophytic fungi (Trichophytons mentagrophyte and Microsporum canis) and Syncephalastrum sp. with fluconazole as a reference drug. In general, compounds 8a and 10b showed selective and potent anticandidal activity (MIC: 0.19–0.81 µM) relative to fluconazole (MIC = 1.00 µM). Furthermore, 10e and 12a elicited a remarkable and selective antifungal activity against Aspergillus sp. and the dermatophytic fungi (MIC: 0.16–0.79 µM) relative to fluconazole (MIC: 2–2.6 µM). Moreover, the docking results of the sulfones 6a, 8a, 10a and 10b at the active site of CYT P450 14α-sterol demethylase showed a comparable binding interaction (interaction Energy = −34.87 to −42.43 kcal/mol) with that of fluconazole (IE = −40.37 kcal/mol). Full article

(This article belongs to the Section Medicinal Chemistry)

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Open AccessArticle

iPPBS-Opt: A Sequence-Based Ensemble Classifier for Identifying Protein-Protein Binding Sites by Optimizing Imbalanced Training Datasets

by Jianhua Jia, Zi Liu, Xuan Xiao, Bingxiang Liu and Kuo-Chen Chou

Molecules 2016, 21(1), 95; https://doi.org/10.3390/molecules21010095 - 19 Jan 2016

Cited by 153 | Viewed by 8513

Abstract

Knowledge of protein-protein interactions and their binding sites is indispensable for in-depth understanding of the networks in living cells. With the avalanche of protein sequences generated in the postgenomic age, it is critical to develop computational methods for identifying in a timely fashion [...] Read more.

Knowledge of protein-protein interactions and their binding sites is indispensable for in-depth understanding of the networks in living cells. With the avalanche of protein sequences generated in the postgenomic age, it is critical to develop computational methods for identifying in a timely fashion the protein-protein binding sites (PPBSs) based on the sequence information alone because the information obtained by this way can be used for both biomedical research and drug development. To address such a challenge, we have proposed a new predictor, called iPPBS-Opt, in which we have used: (1) the K-Nearest Neighbors Cleaning (KNNC) and Inserting Hypothetical Training Samples (IHTS) treatments to optimize the training dataset; (2) the ensemble voting approach to select the most relevant features; and (3) the stationary wavelet transform to formulate the statistical samples. Cross-validation tests by targeting the experiment-confirmed results have demonstrated that the new predictor is very promising, implying that the aforementioned practices are indeed very effective. Particularly, the approach of using the wavelets to express protein/peptide sequences might be the key in grasping the problem’s essence, fully consistent with the findings that many important biological functions of proteins can be elucidated with their low-frequency internal motions. To maximize the convenience of most experimental scientists, we have provided a step-by-step guide on how to use the predictor’s web server (http://www.jci-bioinfo.cn/iPPBS-Opt) to get the desired results without the need to go through the complicated mathematical equations involved. Full article

(This article belongs to the Special Issue Drug Design and Discovery: Principles and Applications)

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Open AccessArticle

Comparative Study of Essential Oils Extracted from Egyptian Basil Leaves (Ocimum basilicum L.) Using Hydro-Distillation and Solvent-Free Microwave Extraction

by Mohammed Chenni, Douniazad El Abed, Njara Rakotomanomana, Xavier Fernandez and Farid Chemat

Molecules 2016, 21(1), 113; https://doi.org/10.3390/molecules21010113 - 19 Jan 2016

Cited by 103 | Viewed by 14144

Abstract

Solvent-free microwave extraction (SFME) and conventional hydro-distillation (HD) were used for the extraction of essential oils (EOs) from Egyptian sweet basil (Ocimum basilicum L.) leaves. The two resulting EOs were compared with regards to their chemical composition, antioxidant, and antimicrobial activities. The [...] Read more.

Solvent-free microwave extraction (SFME) and conventional hydro-distillation (HD) were used for the extraction of essential oils (EOs) from Egyptian sweet basil (Ocimum basilicum L.) leaves. The two resulting EOs were compared with regards to their chemical composition, antioxidant, and antimicrobial activities. The EO analyzed by GC and GC-MS, presented 65 compounds constituting 99.3% and 99.0% of the total oils obtained by SFME and HD, respectively. The main components of both oils were linalool (43.5% SFME; 48.4% HD), followed by methyl chavicol (13.3% SFME; 14.3% HD) and 1,8-cineole (6.8% SFME; 7.3% HD). Their antioxidant activity were studied with the 2,2-diphenyl-1-picrylhydrazyl (DPPH^•) radical scavenging method. The heating conditions effect was evaluated by the determination of the Total Polar Materials (TPM) content. The antimicrobial activity was investigated against five microorganisms: two Gram-positive bacteria, Staphylococcus aureus and Bacillus subtilis, two Gram-negative bacteria, Escherichia coli and Pseudomonas aeruginosa, and one yeast, Candida albicans. Both EOs showed high antimicrobial, but weak antioxidant, activities. The results indicated that the SFME method may be a better alternative for the extraction of EO from O. basilicum since it could be considered as providing a richer source of natural antioxidants, as well as strong antimicrobial agents for food preservation. Full article

(This article belongs to the Special Issue Enabling Technologies and Green Processes for Biorefinery Strategies and Biomass Valorization)

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Open AccessArticle

Total Synthesis of Chiral Falcarindiol Analogues Using BINOL-Promoted Alkyne Addition to Aldehydes

by Li Wang, Ping-Ping Shou, Si-Ping Wei, Chun Zhang, Shuang-Xun Li, Ping-Xian Liu, Xi Du and Qin Wang

Molecules 2016, 21(1), 112; https://doi.org/10.3390/molecules21010112 - 19 Jan 2016

Cited by 7 | Viewed by 6084

Abstract

An enantioselective total synthesis of chiral falcarindiol analogues from buta-1,3-diyn-1-yltriisopropylsilane is reported. The key step in this synthesis is BINOL-promoted asymmetric diacetylene addition to aldehydes. The two chiral centers of the falcarindiol analogues can be produced by using the same kind of catalyst [...] Read more.

An enantioselective total synthesis of chiral falcarindiol analogues from buta-1,3-diyn-1-yltriisopropylsilane is reported. The key step in this synthesis is BINOL-promoted asymmetric diacetylene addition to aldehydes. The two chiral centers of the falcarindiol analogues can be produced by using the same kind of catalyst with high selectivity, and the final product can be obtained in only six steps. Full article

(This article belongs to the Section Organic Chemistry)

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Open AccessArticle

Rapid and Sensitive Detection of Vibrio parahaemolyticus and Vibrio vulnificus by Multiple Endonuclease Restriction Real-Time Loop-Mediated Isothermal Amplification Technique

by Yi Wang, Dongxun Li, Yan Wang, Kewei Li and Changyun Ye

Molecules 2016, 21(1), 111; https://doi.org/10.3390/molecules21010111 - 19 Jan 2016

Cited by 37 | Viewed by 7249

Abstract

Vibrio parahaemolyticus and Vibrio vulnificus are two marine seafood-borne pathogens causing severe illnesses in humans and aquatic animals. In this study, a recently developed novel multiple endonuclease restriction real-time loop-mediated isothermal amplification technology (MERT-LAMP) were successfully developed and evaluated for simultaneous detection of [...] Read more.

Vibrio parahaemolyticus and Vibrio vulnificus are two marine seafood-borne pathogens causing severe illnesses in humans and aquatic animals. In this study, a recently developed novel multiple endonuclease restriction real-time loop-mediated isothermal amplification technology (MERT-LAMP) were successfully developed and evaluated for simultaneous detection of V. parahaemolyticus and V. vulnificus strains in only a single reaction. Two MERT-LAMP primer sets were designed to specifically target toxR gene of V. parahaemolyticus and rpoS gene of V. vulnificus. The MERT-LAMP reactions were conducted at 62 °C, and the positive results were produced in as short as 19 min with the genomic DNA templates extracted from the V. parahaemolyticus and V. vulnificus strains. The two target pathogens present in the same sample could be simultaneously detected and correctly differentiated based on distinct fluorescence curves in a real-time format. The sensitivity of MERT-LAMP assay was 250 fg and 125 fg DNA per reaction with genomic templates of V. parahaemolyticus and V. vulnificus strains, which was in conformity with conventional LAMP detection. Compared with PCR-based techniques, the MERT-LAMP technology was 100- and 10-fold more sensitive than that of PCR and qPCR methods. Moreover, the limit of detection of MERT-LAMP approach for V. parahaemolyticus isolates and V. vulnificus isolates detection in artificially-contaminated oyster samples was 92 CFU and 83 CFU per reaction. In conclusion, the MERT-LAMP assay presented here was a rapid, specific, and sensitive tool for the detection of V. parahaemolyticus and V. vulnificus, and could be adopted for simultaneous screening of V. parahaemolyticus and V. vulnificus in a wide variety of samples. Full article

(This article belongs to the Section Natural Products Chemistry)

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Open AccessArticle

An Integrated Experimental/Theoretical Study of Structurally Related Poly-Thiophenes Used in Photovoltaic Systems

by Davide Vanossi, Luigi Cigarini, Andrea Giaccherini, Enrico Da Como and Claudio Fontanesi

Molecules 2016, 21(1), 110; https://doi.org/10.3390/molecules21010110 - 19 Jan 2016

Cited by 12 | Viewed by 5672

Abstract

In this work, a series of eight thiophene-based polymers (exploited as “donors” in bulk heterojunction photovoltaics cells), whose structures were designed to be suitably tuned with the electronic characteristics of the [6,6]-Phenyl C61 butyric acid methyl ester (PCBM), is considered,. The electronic properties [...] Read more.

In this work, a series of eight thiophene-based polymers (exploited as “donors” in bulk heterojunction photovoltaics cells), whose structures were designed to be suitably tuned with the electronic characteristics of the [6,6]-Phenyl C61 butyric acid methyl ester (PCBM), is considered,. The electronic properties of the mono-, di-, trimeric oligomers are reckoned (at the Hartree-Fock and DFT level of the theory) and compared to experimental spectroscopic and electrochemical results. Indeed, electrochemical and spectroscopic results show a systematic difference whose physical nature is assessed and related to the exciton (electron-hole) binding energy ( J e , h ). The critical comparison of the experimental and theoretical band gaps, i.e., the HOMO-LUMO energy difference, suggests that electrochemical and DFT values are the most suited to being used in the design of a polythiophene-based p-n junction for photovoltaics. Full article

(This article belongs to the Special Issue Metal Nanocatalysts in Green Synthesis and Energy Applications)

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Open AccessArticle

Sorption of Cu(II) Ions on Chitosan-Zeolite X Composites: Impact of Gelling and Drying Conditions

by Amal Djelad, Amine Morsli, Mike Robitzer, Abdelkader Bengueddach, Francesco Di Renzo and Françoise Quignard

Molecules 2016, 21(1), 109; https://doi.org/10.3390/molecules21010109 - 19 Jan 2016

Cited by 31 | Viewed by 7459

Abstract

Chitosan-zeolite Na-X composite beads with open porosity and different zeolite contents were prepared by an encapsulation method. Preparation conditions had to be optimised in order to stabilize the zeolite network during the polysaccharide gelling process. Composites and pure reference components were characterized using [...] Read more.

Chitosan-zeolite Na-X composite beads with open porosity and different zeolite contents were prepared by an encapsulation method. Preparation conditions had to be optimised in order to stabilize the zeolite network during the polysaccharide gelling process. Composites and pure reference components were characterized using X-ray diffraction (XRD); scanning electron microscopy (SEM); N₂ adsorption–desorption; and thermogravimetric analysis (TG). Cu(II) sorption was investigated at pH 6. The choice of drying method used for the storage of the adsorbent severely affects the textural properties of the composite and the copper sorption effectiveness. The copper sorption capacity of chitosan hydrogel is about 190 mg·g⁻¹. More than 70% of this capacity is retained when the polysaccharide is stored as an aerogel after supercrititcal CO₂ drying, but nearly 90% of the capacity is lost after evaporative drying to a xerogel. Textural data and Cu(II) sorption data indicate that the properties of the zeolite-polysaccharide composites are not just the sum of the properties of the individual components. Whereas a chitosan coating impairs the accessibility of the microporosity of the zeolite; the presence of the zeolite improves the stability of the dispersion of chitosan upon supercritical drying and increases the affinity of the composites for Cu(II) cations. Chitosan-zeolite aerogels present Cu(II) sorption properties. Full article

(This article belongs to the Special Issue Chitin, Chitosan and Related Enzymes)

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2116 KiB

Open AccessReview

Application of Bioactive Quercetin in Oncotherapy: From Nutrition to Nanomedicine

by Ju-Suk Nam, Ashish Ranjan Sharma, Lich Thi Nguyen, Chiranjib Chakraborty, Garima Sharma and Sang-Soo Lee

Molecules 2016, 21(1), 108; https://doi.org/10.3390/molecules21010108 - 19 Jan 2016

Cited by 149 | Viewed by 14564

Abstract

Phytochemicals as dietary constituents are being explored for their cancer preventive properties. Quercetin is a major constituent of various dietary products and recently its anti-cancer potential has been extensively explored, revealing its anti-proliferative effect on different cancer cell lines, both in vitro and [...] Read more.

Phytochemicals as dietary constituents are being explored for their cancer preventive properties. Quercetin is a major constituent of various dietary products and recently its anti-cancer potential has been extensively explored, revealing its anti-proliferative effect on different cancer cell lines, both in vitro and in vivo. Quercetin is known to have modulatory effects on cell apoptosis, migration and growth via various signaling pathways. Though, quercetin possesses great medicinal value, its applications as a therapeutic drug are limited. Problems like low oral bioavailability and poor aqueous solubility make quercetin an unreliable candidate for therapeutic purposes. Additionally, the rapid gastrointestinal digestion of quercetin is also a major barrier for its clinical translation. Hence, to overcome these disadvantages quercetin-based nanoformulations are being considered in recent times. Nanoformulations of quercetin have shown promising results in its uptake by the epithelial system as well as enhanced delivery to the target site. Herein we have tried to summarize various methods utilized for nanofabrication of quercetin formulations and for stable and sustained delivery of quercetin. We have also highlighted the various desirable measures for its use as a promising onco-therapeutic agent. Full article

(This article belongs to the Special Issue 20th Anniversary of Molecules—Recent Advances in Natural Products)

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Open AccessArticle

A New Indirect Spectrofluorimetric Method for Determination of Ascorbic Acid with 2,4,6-Tripyridyl-S-Triazine in Pharmaceutical Samples

by Lejla Klepo, Amira Copra-Janicijevic and Lea Kukoc-Modun

Molecules 2016, 21(1), 101; https://doi.org/10.3390/molecules21010101 - 19 Jan 2016

Cited by 7 | Viewed by 5909

Abstract

Ascorbic acid (AA) is a water-soluble vitamin which shows no fluorescence. However, in reaction with iron(III), AA is oxidised to dehydroascorbic acid and iron(III) is reduced to iron(II) which forms a complex with 2,4,6-tripyridyl-S-triazine (TPTZ) in buffered medium. The relative fluorescence [...] Read more.

Ascorbic acid (AA) is a water-soluble vitamin which shows no fluorescence. However, in reaction with iron(III), AA is oxidised to dehydroascorbic acid and iron(III) is reduced to iron(II) which forms a complex with 2,4,6-tripyridyl-S-triazine (TPTZ) in buffered medium. The relative fluorescence intensity of the resulting Fe(TPTZ)₂²⁺ complex can be measured at excitation and emission wavelengths of 393 and 790 nm, respectively. Based on this data, a new indirect spectrofluorimetric method for the determination of AA in pharmaceutical samples was proposed. Influence of the reaction conditions, such as acidity of acetic buffer, concentration of TPTZ and iron(III), reaction time and instrumental parameters were investigated in detail. The linear range was from 5.4 × 10⁻⁴ to 5.4 × 10⁻⁶ mol·L⁻¹ (R = 0.9971). The LOD was 7.7 × 10⁻⁷ mol·L⁻¹ and LOQ was 2.3 × 10⁻⁴ mol·L⁻¹. Fourteen pharmaceutical samples containing various amounts of AA were analysed. Influences of potential interfering substances were also examined. Analysis of commercial pharmaceutical formulations showed good correlation with the nominal values given by the manufacturers and with the results obtained by a titration method. The proposed method can be applied in routine quality control in the pharmaceutical industry due to its sensitivity, simplicity, selectivity and low cost. Full article

(This article belongs to the Section Medicinal Chemistry)

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Open AccessArticle

An Amidochlorin-Based Colorimetric Fluorescent Probe for Selective Cu²⁺ Detection

by Wenting Li, Guohua Zhu, Jinghua Li, Zhiqiang Wang and Yingxue Jin

Molecules 2016, 21(1), 107; https://doi.org/10.3390/molecules21010107 - 18 Jan 2016

Cited by 27 | Viewed by 7294

Abstract

The design and synthesis of selective and sensitive chemosensors for the quantification of environmentally and biologically important ionic species has attracted widespread attention. Amidochlorin p6 (ACP); an effective colorimetric and fluorescent probe for copper ions (Cu²⁺) in aqueous solution [...] Read more.

The design and synthesis of selective and sensitive chemosensors for the quantification of environmentally and biologically important ionic species has attracted widespread attention. Amidochlorin p6 (ACP); an effective colorimetric and fluorescent probe for copper ions (Cu²⁺) in aqueous solution derived from methyl pheophorbide-a (MPa) was designed and synthesized. A remarkable color change from pale yellow to blue was easily observed by the naked eye upon addition of Cu²⁺; and a fluorescence quenching was also determined. The research of fluorescent quenching of ACP-Cu²⁺ complexation showed the detection limit was 7.5 × 10⁻⁸ mol/L; which suggested that ACP can act as a high sensitive probe for Cu²⁺ and can be used to quantitatively detect low levels of Cu²⁺ in aqueous solution. In aqueous solution the probe exhibits excellent selectivity and sensitivity toward Cu²⁺ ions over other metal ions (M = Zn²⁺; Ni²⁺; Ba²⁺; Ag⁺; Co²⁺; Na⁺; K⁺; Mg²⁺; Cd²⁺; Pb²⁺; Mn²⁺; Fe³⁺; and Ca²⁺). The obvious change from pale yellow to blue upon the addition of Cu²⁺ could make it a suitable “naked eye” indicator for Cu²⁺. Full article

(This article belongs to the Special Issue Photoactive Molecules)

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Open AccessArticle

Assessment of Egg Yolk Oil Extraction Methods of for ShiZhenKang Oil by Pharmacodynamic Index Evaluation

by Ping Wu, Yu Pan, Jianye Yan, Dan Huang and Shunxiang Li

Molecules 2016, 21(1), 106; https://doi.org/10.3390/molecules21010106 - 18 Jan 2016

Cited by 13 | Viewed by 21294

Abstract

To assess the extraction methods of egg yolk oil in ShiZhenKang (SZK) oil, which is used to treat eczema, a mice model of eczema was established by using 2,4-dinitrochlorobenzene (DNCB). The therapeutic effects of egg yolk oil extracted by different methods from SZK [...] Read more.

To assess the extraction methods of egg yolk oil in ShiZhenKang (SZK) oil, which is used to treat eczema, a mice model of eczema was established by using 2,4-dinitrochlorobenzene (DNCB). The therapeutic effects of egg yolk oil extracted by different methods from SZK oil on the model of acute eczema in mice were evaluated. The oil yield rate of ethanol extraction is 42.06%. Its egg yolk oil is orange and has a rich, sweet, egg smell. Moreover, the SZK oil prepared from it has a very good therapeutic effect on the model of acute eczema in mice. The alcohol extraction method is the preferable method according to a comprehensive evaluation of each index of seven kinds of methods to extract the egg yolk oil. Full article

(This article belongs to the Section Natural Products Chemistry)

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Open AccessArticle

Phenylethanol Glycosides from Cistanche tubulosa Suppress Hepatic Stellate Cell Activation and Block the Conduction of Signaling Pathways in TGF-β₁/smad as Potential Anti-Hepatic Fibrosis Agents

by Shu-Ping You, Long Ma, Jun Zhao, Shi-Lei Zhang and Tao Liu

Molecules 2016, 21(1), 102; https://doi.org/10.3390/molecules21010102 - 18 Jan 2016

Cited by 45 | Viewed by 7078

Abstract

Cistanche tubulosa is a traditional Chinese herbal medicine widely used for regulating immunity and phenylethanol glycosides (CPhGs) are among the primary components responsible for this activity. Previous studies have indicated the preventive and therapeutic effects of CPhGs on bovine serum albumin (BSA)-induced hepatic [...] Read more.

Cistanche tubulosa is a traditional Chinese herbal medicine widely used for regulating immunity and phenylethanol glycosides (CPhGs) are among the primary components responsible for this activity. Previous studies have indicated the preventive and therapeutic effects of CPhGs on bovine serum albumin (BSA)-induced hepatic fibrosis in rats. The aim of the study was to evaluate the anti-hepatic fibrosis effect of CPhGs and the monomers echinacoside and acteoside by inhibiting hepatic stellate cell (HSC) activation, blocking the conduction of signaling pathways in transforming growth factor-β₁ (TGF-β₁)/smad, and determine their in vitro hepatoprotective activity. HSC proliferation was obviously inhibited after treatment with CPhGs (100, 50 μg/mL)/echinacoside (500, 250, 125 μg/mL)/acteoside (6, 3 μg/mL), with IC₅₀ values of 119.125, 520.345 and 6.999 μg/mL, respectively, in the MTT assay. Different concentrations of CPhGs/echinacoside/acteoside did not affect the cellular toxicity on HSC according to lactate dehydrogenase (LDH) measurements. Different concentrations of CPhGs/echinacoside/acteoside increased the mRNA level and protein expression of smad7, and decreased the mRNA levels of smad2, smad3 and the protein expression of smad2, phospho-smad2 (p-smad2), smad3, phospho-smad3 (p-smad3) in HSC. In summary, these results demonstrate that CPhGs/echinacoside/acteoside can block the conduction of the signaling pathways in TGF-β₁/smad, and inhibit the activation of HSC, suggesting that C. tubulosa may thus be a potential herbal medicine for the treatment of liver fibrosis. Full article

(This article belongs to the Section Medicinal Chemistry)

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Open AccessArticle

An Unusual Stress Metabolite from a Hydrothermal Vent Fungus Aspergillus sp. WU 243 Induced by Cobalt

by Chihong Ding, Xiaodan Wu, Bibi Nazia Auckloo, Chen-Tung Arthur Chen, Ying Ye, Kuiwu Wang and Bin Wu

Molecules 2016, 21(1), 105; https://doi.org/10.3390/molecules21010105 - 16 Jan 2016

Cited by 27 | Viewed by 7035

Abstract

A novel hybrid polyketide-terpenoid, aspergstressin (1), possessing a unique fused polycyclic structure, was induced from culture broth of strain Aspergillus sp. WU 243 by cobalt ion stimulation. The strain was isolated from the digestive gland of Xenograpsus testudinatus, a unique [...] Read more.

A novel hybrid polyketide-terpenoid, aspergstressin (1), possessing a unique fused polycyclic structure, was induced from culture broth of strain Aspergillus sp. WU 243 by cobalt ion stimulation. The strain was isolated from the digestive gland of Xenograpsus testudinatus, a unique type of crab which dwells in the Kueishantao hydrothermal vents off Taiwan. The chemical structure and relative configuration of the stress metabolite were established by spectroscopic means. Aspergillus sp. WU 243 produced aspergstressin (1) only under cobalt stressed culture conditions. The results show that stress-driven discovery of new natural products from hydrothermal vent fungi is an effective strategy to unveil the untapped reservoir of small molecules from species found in the hydrothermal vent environment. Full article

(This article belongs to the Special Issue Metal Mediated Activation of Small Molecules)

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Open AccessArticle

Exploration of Scaffolds from Natural Products with Antiplasmodial Activities, Currently Registered Antimalarial Drugs and Public Malarial Screen Data

by Samuel Egieyeh, James Syce, Alan Christoffels and Sarel F. Malan

Molecules 2016, 21(1), 104; https://doi.org/10.3390/molecules21010104 - 16 Jan 2016

Cited by 7 | Viewed by 7067

Abstract

In light of current resistance to antimalarial drugs, there is a need to discover new classes of antimalarial agents with unique mechanisms of action. Identification of unique scaffolds from natural products with in vitro antiplasmodial activities may be the starting point for such [...] Read more.

In light of current resistance to antimalarial drugs, there is a need to discover new classes of antimalarial agents with unique mechanisms of action. Identification of unique scaffolds from natural products with in vitro antiplasmodial activities may be the starting point for such new classes of antimalarial agents. We therefore conducted scaffold diversity and comparison analysis of natural products with in vitro antiplasmodial activities (NAA), currently registered antimalarial drugs (CRAD) and malaria screen data from Medicine for Malaria Ventures (MMV). The scaffold diversity analyses on the three datasets were performed using scaffold counts and cumulative scaffold frequency plots. Scaffolds from the NAA were compared to those from CRAD and MMV. A Scaffold Tree was also generated for each of the datasets and the scaffold diversity of NAA was found to be higher than that of MMV. Among the NAA compounds, we identified unique scaffolds that were not contained in any of the other compound datasets. These scaffolds from NAA also possess desirable drug-like properties making them ideal starting points for antimalarial drug design considerations. The Scaffold Tree showed the preponderance of ring systems in NAA and identified virtual scaffolds, which may be potential bioactive compounds. Full article

(This article belongs to the Special Issue Computational Design: A New Approach to Drug and Molecular Discovery)

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1244 KiB

Open AccessArticle

Antibacterial Peptide CecropinB2 Production via Various Host and Construct Systems

by Wei-Shiang Lai, Shu-Chen Kan, Chia-Chi Lin, Chwen-Jen Shieh and Yung-Chuan Liu

Molecules 2016, 21(1), 103; https://doi.org/10.3390/molecules21010103 - 16 Jan 2016

Cited by 7 | Viewed by 5441

Abstract

Cecropin is a cationic antibacterial peptide composed of 35–39 residues. This peptide has been identified as possessing strong antibacterial activity and low toxicity against eukaryotic cells, and it has been claimed that some types of the cecropin family of peptides are capable of [...] Read more.

Cecropin is a cationic antibacterial peptide composed of 35–39 residues. This peptide has been identified as possessing strong antibacterial activity and low toxicity against eukaryotic cells, and it has been claimed that some types of the cecropin family of peptides are capable of killing cancer cells. In this study, the host effect of cloning antibacterial peptide cecropinB2 was investigated. Three different host expression systems were chosen, i.e., Escherichia coli, Bacillus subtilis and Pichia pastoris. Two gene constructs, cecropinB2 (cecB2) and intein-cecropinB2 (INT-cecB2), were applied. Signal peptide and propeptide from Armigeres subalbatus were also attached to the gene construct. The results showed that the best host for cloning cecropinB2 was P. pastoris SMD1168 harboring the gene of pGAPzαC-prepro-cecB2 via Western blot confirmation. The cecropinB2 that was purified using immobilized-metal affinity chromatography resin showed strong antibacterial activity against the Gram-negative strains, including the multi-drug-resistant bacteria Acinetobacter baumannii. Full article

(This article belongs to the Section Medicinal Chemistry)

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