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Molecules, Volume 22, Issue 3 (March 2017)

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Cover Story (view full-size image) In the New Medicines for Trypanosomatidic Infections (NMTRypI) project funded by the EU, we have [...] Read more.
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Open AccessReview Potential Antivirals: Natural Products Targeting Replication Enzymes of Dengue and Chikungunya Viruses
Molecules 2017, 22(3), 505; https://doi.org/10.3390/molecules22030505
Received: 20 December 2016 / Revised: 9 March 2017 / Accepted: 17 March 2017 / Published: 22 March 2017
Cited by 5 | PDF Full-text (2720 KB) | HTML Full-text | XML Full-text
Abstract
Dengue virus (DENV) and chikungunya virus (CHIKV) are reemergent arboviruses that are transmitted by mosquitoes of the Aedes genus. During the last several decades, these viruses have been responsible for millions of cases of infection and thousands of deaths worldwide. Therefore, several investigations
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Dengue virus (DENV) and chikungunya virus (CHIKV) are reemergent arboviruses that are transmitted by mosquitoes of the Aedes genus. During the last several decades, these viruses have been responsible for millions of cases of infection and thousands of deaths worldwide. Therefore, several investigations were conducted over the past few years to find antiviral compounds for the treatment of DENV and CHIKV infections. One attractive strategy is the screening of compounds that target enzymes involved in the replication of both DENV and CHIKV. In this review, we describe advances in the evaluation of natural products targeting the enzymes involved in the replication of these viruses. Full article
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Open AccessArticle The Anti-Allergic Rhinitis Effect of Traditional Chinese Medicine of Shenqi by Regulating Mast Cell Degranulation and Th1/Th2 Cytokine Balance
Molecules 2017, 22(3), 504; https://doi.org/10.3390/molecules22030504
Received: 21 February 2017 / Revised: 21 March 2017 / Accepted: 21 March 2017 / Published: 22 March 2017
Cited by 3 | PDF Full-text (2671 KB) | HTML Full-text | XML Full-text
Abstract
Shenqi is a traditional Chinese polyherbal medicine has been widely used for the treatment of allergic rhinitis (AR). The aim of this study was to investigate the anti-allergic rhinitis activity of Shenqi and explore its underlying molecular mechanism. Ovalbumin (OVA)-induced allergic rhinitis rat
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Shenqi is a traditional Chinese polyherbal medicine has been widely used for the treatment of allergic rhinitis (AR). The aim of this study was to investigate the anti-allergic rhinitis activity of Shenqi and explore its underlying molecular mechanism. Ovalbumin (OVA)-induced allergic rhinitis rat model was used to evaluate the anti-allergic rhinitis effect of Shenqi. The effect of Shenqi on IgE-mediated degranulation was measured using rat basophilic leukemia (RBL-2H3) cells. Primary spleen lymphocytes were isolated to investigate the anti-allergic mechanism of Shenqi by detecting the expression of transcription factors via Western blot and the level of cytokines (IL-4 and IFN-γ) via ELISA. In OVA-induced AR rat models, Shenqi relieved the allergic rhinitis symptoms, inhibited the histopathological changes of nasal mucosa, and reduced the levels of IL-4 and IgE. The results from the in vitro study certified that Shenqi inhibited mast cell degranulation. Furthermore, the results of GATA3, T-bet, p-STAT6, and SOCS1 expression and production of IFN-γ and IL-4 demonstrated that Shenqi balanced the ratio of Th1/Th2 (IFN-γ/IL-4) in OVA-stimulated spleen lymphocytes. In conclusion, these results suggest that Shenqi exhibits an obvious anti-allergic effect by suppressing the mast cell-mediated allergic response and by improving the imbalance of Th1/Th2 ratio in allergic rhinitis. Full article
(This article belongs to the Section Natural Products Chemistry)
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Open AccessArticle Consecutive One-Pot versus Domino Multicomponent Approaches to 3-(Diarylmethylene)oxindoles
Molecules 2017, 22(3), 503; https://doi.org/10.3390/molecules22030503
Received: 27 February 2017 / Revised: 9 March 2017 / Accepted: 17 March 2017 / Published: 22 March 2017
Cited by 2 | PDF Full-text (4684 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Based on consecutive one-pot conditions combining three palladium-catalyzed reactions (Sonogashira, Heck and Suzuki-Miyaura reactions), a more efficient domino multicomponent method has been successfully developed to access a wide variety of 3-(diarylmethylene)oxindoles. Microwave irradiation and use of a silver salt were the most important
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Based on consecutive one-pot conditions combining three palladium-catalyzed reactions (Sonogashira, Heck and Suzuki-Miyaura reactions), a more efficient domino multicomponent method has been successfully developed to access a wide variety of 3-(diarylmethylene)oxindoles. Microwave irradiation and use of a silver salt were the most important factors to achieve high yields and stereoselectivity. Full article
(This article belongs to the collection Heterocyclic Compounds)
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Open AccessArticle Carapanosins A–C from Seeds of Andiroba (Carapa guianensis, Meliaceae) and Their Effects on LPS-Activated NO Production
Molecules 2017, 22(3), 502; https://doi.org/10.3390/molecules22030502
Received: 7 February 2017 / Revised: 13 March 2017 / Accepted: 15 March 2017 / Published: 22 March 2017
Cited by 1 | PDF Full-text (1274 KB) | HTML Full-text | XML Full-text
Abstract
Two new phragmalin-type limonoids, Carapanosins A and B (1 and 2), and a new gedunin-type limonoid, Carapansin C (3), together with five known limonoids (48) were isolated from the oil of Carapa guianensis AUBLET
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Two new phragmalin-type limonoids, Carapanosins A and B (1 and 2), and a new gedunin-type limonoid, Carapansin C (3), together with five known limonoids (48) were isolated from the oil of Carapa guianensis AUBLET (Meliaceae) seeds, a traditional medicine in Brazil and Latin American countries. Their structures were elucidated on the basis of spectroscopic analyses using 1D and 2D NMR techniques and HRFABMS. Compounds 18 were evaluated for their effects on the production of NO in LPS-activated mouse peritoneal macrophages. The NO inhibitory assay suggested that Compounds 3, 6, and 8 may be valuable as potential inhibitors of macrophage activation. Full article
(This article belongs to the Section Natural Products Chemistry)
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Open AccessArticle Synthesis, Characterization, and the Antioxidant Activity of Double Quaternized Chitosan Derivatives
Molecules 2017, 22(3), 501; https://doi.org/10.3390/molecules22030501
Received: 19 January 2017 / Revised: 9 March 2017 / Accepted: 17 March 2017 / Published: 22 March 2017
Cited by 5 | PDF Full-text (1677 KB) | HTML Full-text | XML Full-text
Abstract
With the specialty of improving the water solubility of chitosan, quaternary ammonium salts have broadened the application of this polysaccharide in food, medicine and pesticides. To identify the effect of quaternary ammonium salts’ quantity, single quaternized chitosan N-phenmethyl-N,N-dimethyl
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With the specialty of improving the water solubility of chitosan, quaternary ammonium salts have broadened the application of this polysaccharide in food, medicine and pesticides. To identify the effect of quaternary ammonium salts’ quantity, single quaternized chitosan N-phenmethyl-N,N-dimethyl chitosan (PDCS), double quaternized chitosan N-(1-pyridylmethyl-2-ylmethyl)-N,N-dimethyl chitosan (MP2MDCS), N-(1-pyridylmethyl-3-ylmethyl)-N,N-dimethyl chitosan (MP3MDCS), and N-(1-pyridylmethyl-4-ylmethyl)-N,N-dimethyl chitosan (MP4MDCS) were designed and synthesized successfully through chemical modification of chitosan. Besides, three kinds of antioxidant activities, including hydroxyl radicals, superoxide radicals, and 1,1-Diphenyl-2-picrylhydrazyl (DPPH) radicals were tested in vitro. As shown in this paper, the scavenging ability was ranking in order of MP3MDC > MP4MDCS > MP2MDCS > PDCS > chitosan at 1.6 mg/mL in all assays. All double quaternary ammonium salts were better than chitosan or the single quaternary ammonium salt. In addition, MP3MDCS could scavenge hydroxyl radicals totally at 1.6 mg/mL. MP2MDCS and MP4MDCS with more than 90% scavenging indices both had great scavenging ability on hydroxyl radicals or DPPH radicals. Furthermore, these data demonstrated that the increasing number of the positive charge would improve the antioxidant property of chitosan derivatives, and the N-pyridinium position would influence the scavenging radical ability. Full article
(This article belongs to the Section Medicinal Chemistry)
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Open AccessArticle Physicochemical Properties and Microbial Quality of Tremella aurantialba Packed in Antimicrobial Composite Films
Molecules 2017, 22(3), 500; https://doi.org/10.3390/molecules22030500
Received: 4 January 2017 / Revised: 8 March 2017 / Accepted: 16 March 2017 / Published: 22 March 2017
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Abstract
The effects of poly(lactic acid) (PLA)-based film with inorganic antimicrobial nano-TiO2 and nano-Ag on the physicochemical and microbial quality of Tremella aurantialba stored at 4 ± 1 °C for 16 days was investigated. Rosemary essential oil (REO, 9 wt %) was added
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The effects of poly(lactic acid) (PLA)-based film with inorganic antimicrobial nano-TiO2 and nano-Ag on the physicochemical and microbial quality of Tremella aurantialba stored at 4 ± 1 °C for 16 days was investigated. Rosemary essential oil (REO, 9 wt %) was added into PLA film as plasticizer. Low-density polyethylene (LDPE) and PLA film was used as the controls. The experiment measured physicochemical properties and microbial levels, such as weight loss, firmness, vitamin C, color, microbiological quality, and sensory quality. Although Tremella aurantialba packed by nano-composite films had the highest weight loss (4.96% and 5.17%) at the end of storage, it was still in the vicinity of 5%. Tremella aurantialba packed with nano-composite films were significantly (p < 0.05) firmer than those packed by LDPE, PLA, and PLA/REO films. The nano-composite films were more effective in reducing vitamin C and microbial counts and preserving the color of Tremella aurantialba than the other three groups. The overall acceptability of Tremella aurantialba packed by the nano-composite films still remained good and within the limits of marketability after 12 days of storage. The results suggested that the proposed nano-composite films could maintain the quality of Tremella aurantialba and extend its postharvest life. Full article
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Open AccessArticle Exploring the Antitumor Mechanism of High-Dose Cytarabine through the Metabolic Perturbations of Ribonucleotide and Deoxyribonucleotide in Human Promyelocytic Leukemia HL-60 Cells
Molecules 2017, 22(3), 499; https://doi.org/10.3390/molecules22030499
Received: 8 March 2017 / Revised: 17 March 2017 / Accepted: 20 March 2017 / Published: 21 March 2017
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Abstract
Despite the apparent clinical benefits of high-dose cytarabine (Ara-C) over lower dose Ara-C in acute myeloid leukemia (AML) therapy, the mechanism behind high-dose Ara-C therapy remains uncertain. In this study, a LC-MS-based method was carried out to investigate the metabolic alteration of ribonucleotide
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Despite the apparent clinical benefits of high-dose cytarabine (Ara-C) over lower dose Ara-C in acute myeloid leukemia (AML) therapy, the mechanism behind high-dose Ara-C therapy remains uncertain. In this study, a LC-MS-based method was carried out to investigate the metabolic alteration of ribonucleotide and deoxyribonucleotide in human promyelocytic leukemia cells (HL-60) after treatment with Ara-C to reveal its antitumor mechanism. The metabolic results revealed that four nucleotides (ATP, ADP, CDP, and dCTP) could be used as potential biomarkers indicating the benefit of high-dose Ara-C over lower dose Ara-C treatment. Combining metabolic perturbation and cell cycle analysis, we conjectured that, apart from the acknowledged mechanism of Ara-C on tumor inhibition, high-dose Ara-C could present a specific action pathway. It was suggested that the pronounced rise in AMP/ATP ratio induced by high-dose Ara-C can trigger AMP-activated protein kinase (AMPK) and subsequently Forkhead Box, class O (FoxO), to promote cell cycle arrest. Moreover, the significant decrease in CDP pool induced by high-dose Ara-C might further accelerate the reduction of dCTP, which then aggravates DNA synthesis disturbance. As a result, all of these alterations led to heightened tumor inhibition. This study provides new insight in the investigation of potential mechanisms in the clinical benefits of high-dose Ara-C in therapy for AML. Full article
(This article belongs to the Special Issue Nucleoside and Nucleotide Analogues)
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Open AccessArticle The Effects of Sweet Foods on the Pharmacokinetics of Glycyrrhizic Acid by icELISA
Molecules 2017, 22(3), 498; https://doi.org/10.3390/molecules22030498
Received: 16 February 2017 / Revised: 13 March 2017 / Accepted: 16 March 2017 / Published: 21 March 2017
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Abstract
The effect of sweet foods, such as honey, was investigated from the perspective of pharmacokinetics on the absorption of glycyrrhizic acid (GA). Due to the unique properties of indirect competitive enzyme-linked immunosorbent assay (icELISA), namely, its: specificity, sensitivity, repeatability, simple pretreatment of samples,
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The effect of sweet foods, such as honey, was investigated from the perspective of pharmacokinetics on the absorption of glycyrrhizic acid (GA). Due to the unique properties of indirect competitive enzyme-linked immunosorbent assay (icELISA), namely, its: specificity, sensitivity, repeatability, simple pretreatment of samples, fast and simple operation, and because it is economic and non-polluting, it has received increased attention. In this study, we used the advantages of this method to see how honey affected the pharmacokinetics of GA. The effects of honey on the pharmacokinetics of GA by ELISA were investigated for the first time. The results indicate that honey can postpone the peak concentration of GA in mouse blood, and this effect correlates well with fructose. As a representative of sweet foods, the result provides the valuable information that honey, or fructose, may act as sustained-releasing drugs in clinical scenarios; and that sweet foods may have some influences on drugs when taken together. Full article
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Open AccessArticle Biosynthesis of Oligomeric Anthocyanins from Grape Skin Extracts
Molecules 2017, 22(3), 497; https://doi.org/10.3390/molecules22030497
Received: 3 January 2017 / Revised: 3 March 2017 / Accepted: 10 March 2017 / Published: 21 March 2017
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Abstract
We synthesized oligomeric anthocyanins from grape skin-derived monomeric anthocyanins such as anthocyanidin and proanthocyanidin by a fermentation technique using Aspergillus niger, crude enzymes and glucosidase. The biosyntheses of the oligomeric anthocyanins carried out by the conventional method using Aspergillus niger and crude
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We synthesized oligomeric anthocyanins from grape skin-derived monomeric anthocyanins such as anthocyanidin and proanthocyanidin by a fermentation technique using Aspergillus niger, crude enzymes and glucosidase. The biosyntheses of the oligomeric anthocyanins carried out by the conventional method using Aspergillus niger and crude enzymes were confirmed by ESI-MS. The molecular weight of the synthesized anthocyanin oligomers was determined using MALDI-MS. The yield of anthocyanin oligomers using crude enzymes was higher than that of the synthesis using Aspergillus fermentation. Several studies have been demonstrated that oligomeric anthocyanins have higher antioxidant activity than monomeric anthocyanins. Fermentation-based synthesis of oligomeric anthocyanins is an alternative way of producing useful anthocyanins that could support the food industry. Full article
(This article belongs to the Special Issue Green Production of Bioactive Natural Products)
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Open AccessArticle GC-MS Metabolomic Analysis to Reveal the Metabolites and Biological Pathways Involved in the Developmental Stages and Tissue Response of Panax ginseng
Molecules 2017, 22(3), 496; https://doi.org/10.3390/molecules22030496
Received: 11 January 2017 / Revised: 14 March 2017 / Accepted: 16 March 2017 / Published: 21 March 2017
Cited by 4 | PDF Full-text (3967 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Ginsenosides, the major compounds present in ginseng, are known to have numerous physiological and pharmacological effects. The physiological processes, enzymes and genes involved in ginsenoside synthesis in P. ginseng have been well characterized. However, relatively little information is known about the dynamic metabolic
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Ginsenosides, the major compounds present in ginseng, are known to have numerous physiological and pharmacological effects. The physiological processes, enzymes and genes involved in ginsenoside synthesis in P. ginseng have been well characterized. However, relatively little information is known about the dynamic metabolic changes that occur during ginsenoside accumulation in ginseng. To explore this topic, we isolated metabolites from different tissues at different growth stages, and identified and characterized them by using gas chromatography coupled with mass spectrometry (GC-MS). The results showed that a total of 30, 16, 20, 36 and 31 metabolites were identified and involved in different developmental stages in leaf, stem, petiole, lateral root and main root, respectively. To investigate the contribution of tissue to the biosynthesis of ginsenosides, we examined the metabolic changes of leaf, stem, petiole, lateral root and main root during five development stages: 1-, 2-, 3-, 4- and 5-years. The score plots of partial least squares-discriminate analysis (PLS-DA) showed clear discrimination between growth stages and tissue samples. Kyoto Encyclopedia of Genes and Genomes (KEGG) pathway analysis in the same tissue at different growth stages indicated profound biochemical changes in several pathways, including carbohydrate metabolism and pentose phosphate metabolism, in addition, the tissues displayed significant variations in amino acid metabolism, sugar metabolism and energy metabolism. These results should facilitate further dissection of the metabolic flux regulation of ginsenoside accumulation in different developmental stages or different tissues of ginseng. Full article
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Open AccessArticle 3-Substituted N-Benzylpyrazine-2-carboxamide Derivatives: Synthesis, Antimycobacterial and Antibacterial Evaluation
Molecules 2017, 22(3), 495; https://doi.org/10.3390/molecules22030495
Received: 6 February 2017 / Revised: 6 March 2017 / Accepted: 17 March 2017 / Published: 21 March 2017
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Abstract
A series of substituted N-benzyl-3-chloropyrazine-2-carboxamides were prepared as positional isomers of 5-chloro and 6-chloro derivatives, prepared previously. During the aminolysis of the acyl chloride, the simultaneous substitution of chlorine with benzylamino moiety gave rise to N-benzyl-3-(benzylamino)pyrazine-2-carboxamides as side products, in some
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A series of substituted N-benzyl-3-chloropyrazine-2-carboxamides were prepared as positional isomers of 5-chloro and 6-chloro derivatives, prepared previously. During the aminolysis of the acyl chloride, the simultaneous substitution of chlorine with benzylamino moiety gave rise to N-benzyl-3-(benzylamino)pyrazine-2-carboxamides as side products, in some cases. Although not initially planned, the reaction conditions were modified to populate this double substituted series. The final compounds were tested against four mycobacterial strains. N-(2-methylbenzyl)-3-((2-methylbenzyl)amino)pyrazine-2-carboxamide (1a) and N-(3,4-dichlorobenzyl)-3-((3,4-dichlorobenzyl)amino)pyrazine-2-carboxamide (9a) proved to be the most effective against Mycobacterium tuberculosis H37Rv, with MIC = 12.5 μg·mL−1. Compounds were screened for antibacterial activity. The most active compound was 3-chloro-N-(2-chlorobenzyl)pyrazine-2-carboxamide (5) against Staphylococcus aureus with MIC = 7.81 μM, and Staphylococcus epidermidis with MIC = 15.62 μM. HepG2 in vitro cytotoxicity was evaluated for the most active compounds; however, no significant toxicity was detected. Compound 9a was docked to several conformations of the enoyl-ACP-reductase of Mycobacterium tuberculosis. In some cases, it was capable of H-bond interactions, typical for most of the known inhibitors. Full article
(This article belongs to the Section Medicinal Chemistry)
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Open AccessArticle Profiling and Preparation of Metabolites from Pyragrel in Human Urine by Online Solid-Phase Extraction Coupled with High Performance Liquid Chromatography Tandem Mass Spectrometry Followed by a Macroporous Resin-Based Purification Approach
Molecules 2017, 22(3), 494; https://doi.org/10.3390/molecules22030494
Received: 8 February 2017 / Revised: 18 March 2017 / Accepted: 19 March 2017 / Published: 21 March 2017
Cited by 2 | PDF Full-text (2465 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Pyragrel, a new anticoagulant drug, is derived from the molecular combination of ligustrazine and ferulic acid. Pyragrel showed significant inhibitory activity against platelet aggregation induced by adenosine diphosphate (ADP), and had been approved for a phase I clinical trial by CFDA. To characterize
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Pyragrel, a new anticoagulant drug, is derived from the molecular combination of ligustrazine and ferulic acid. Pyragrel showed significant inhibitory activity against platelet aggregation induced by adenosine diphosphate (ADP), and had been approved for a phase I clinical trial by CFDA. To characterize the metabolites of Pyragrel in human urine after intravenous administration, a reliable online solid-phase extraction couple with high performance liquid chromatography tandem mass spectrometry (online SPE-HPLC-MSn) method was conceived and applied. Five metabolites were detected and tentatively identified, which suggested that the major metabolic pathways of Pyragrel in human were double-bond reduction, double-bond oxidation, and then followed by glucuronide conjugation. Two main metabolites were then prepared using β-glucuronide hydrolysis and macroporous resin purification approach followed by preparative high-performance liquid chromatography (PHPLC) method, with their structures confirmed on the basis of nuclear magnetic resonance (NMR) data. This study provided information for the further study of the metabolism and excretion of Pyragrel. Full article
(This article belongs to the Section Metabolites)
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Open AccessArticle Nonradiative Relaxation Mechanisms of UV Excited Phenylalanine Residues: A Comparative Computational Study
Molecules 2017, 22(3), 493; https://doi.org/10.3390/molecules22030493
Received: 6 February 2017 / Revised: 9 March 2017 / Accepted: 16 March 2017 / Published: 21 March 2017
Cited by 3 | PDF Full-text (7314 KB) | HTML Full-text | XML Full-text
Abstract
The present work is directed toward understanding the mechanisms of excited state deactivation in three neutral model peptides containing the phenylalanine residue. The excited state dynamics of theγL(g+)folded form of N-acetylphenylalaninylamide (NAPA B) and its
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The present work is directed toward understanding the mechanisms of excited state deactivation in three neutral model peptides containing the phenylalanine residue. The excited state dynamics of theγL(g+)folded form of N-acetylphenylalaninylamide (NAPA B) and its amide-N-methylated derivative (NAPMA B) is reviewed and compared to the dynamics of the monohydrated structure of NAPA (NAPAH). The goal is to unravel how the environment, and in particular solvation, impacts the photodynamics of peptides. The systems are investigated using reaction path calculations and surface hopping nonadiabatic dynamics based on the coupled cluster doubles (CC2) method and time-dependent density functional theory. The work emphasizes the role that excitation transfer from the phenylππ*to amidenπ*state plays in the deactivation of the three systems and shows how the ease of out-of-plane distortions of the amide group determines the rate of population transfer between the two electronic states. The subsequent dynamics on thenπ*state is barrierless along several pathways and leads to fast deactivation to the ground electronic state. Full article
(This article belongs to the Special Issue Experimental and Computational Photochemistry of Bioorganic Molecules)
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Open AccessArticle New Chiral Ebselen Analogues with Antioxidant and Cytotoxic Potential
Molecules 2017, 22(3), 492; https://doi.org/10.3390/molecules22030492
Received: 30 January 2017 / Revised: 14 March 2017 / Accepted: 17 March 2017 / Published: 20 March 2017
Cited by 3 | PDF Full-text (2012 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
New chiral camphane-derived benzisoselenazol-3(2H)-ones and corresponding diselenides have been synthetized using a convenient one-pot procedure. Se-N bond was efficiently converted to an Se-Se bond, which could also be easily re-oxidized to the initial benzisoselenazolone moiety. The antioxidant activity of camphor derivatives
[...] Read more.
New chiral camphane-derived benzisoselenazol-3(2H)-ones and corresponding diselenides have been synthetized using a convenient one-pot procedure. Se-N bond was efficiently converted to an Se-Se bond, which could also be easily re-oxidized to the initial benzisoselenazolone moiety. The antioxidant activity of camphor derivatives was evaluated and compared to the reactivity of a series of N-amino acid benzisoselenazol-3(2H)-ones obtained by a modified procedure involving the improved synthesis and isolation of the diseleno bis(dibenzoic) acid. The most efficient peroxide scavengers, N-bornyl and N-leucine methyl ester benzisoselenazol-3(2H)-ones, were further evaluated as cytotoxic agents on four cancer cell lines (MCF-7, HEP G2, HL 6, and DU 145) and normal cell line PNT1A. The highest antiproliferative potential was evaluated for two compounds bearing a 3-methylbutyl carbon chain, N-leucine methyl ester and N-3-methylbutyl benzisoselenazol-3(2H)-ones. Full article
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Open AccessArticle [2 + 2] Photodimerization of Naphthylvinylpyridines through Cation-π Interactions in Acidic Solution
Molecules 2017, 22(3), 491; https://doi.org/10.3390/molecules22030491
Received: 21 February 2017 / Revised: 8 March 2017 / Accepted: 15 March 2017 / Published: 20 March 2017
Cited by 2 | PDF Full-text (2505 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Irradiation of (E)-4-(2-(2-naphthyl)vinyl)pyridine (1a) and (E)-4-(2-(1-naphthyl)vinyl)pyridine (1b) with a 250 W high-pressure mercury lamp in acidic solution afforded synHT dimers in high stereoselectivities. Similar results were obtained by visible light irradiation. On the other
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Irradiation of (E)-4-(2-(2-naphthyl)vinyl)pyridine (1a) and (E)-4-(2-(1-naphthyl)vinyl)pyridine (1b) with a 250 W high-pressure mercury lamp in acidic solution afforded synHT dimers in high stereoselectivities. Similar results were obtained by visible light irradiation. On the other hand, when the reactions were carried out under neutral conditions, the stereoselectivities were very low, and the yields were decreased by visible light irradiation. Comparison of the UV-vis spectra between the acidic and the neutral conditions elucidated that the red shift was observed in acidic solutions. These results show that HCl plays essential roles not only in the preorientation of substrates through cation-π interactions, but also in the changes in the absorption properties of substrates that enable visible light reactions. Full article
(This article belongs to the Special Issue Cutting-Edge Organic Chemistry in Japan)
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