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

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23 KiB  
Correction
Roy et al. On Two Novel Parameters for Validation of Predictive QSAR Models. Molecules, 2009, 14, 1660-1701
by Partha Pratim Roy, Somnath Paul, Indrani Mitra and Kunal Roy
Molecules 2010, 15(1), 604-605; https://doi.org/10.3390/molecules15010604 - 26 Jan 2010
Cited by 8 | Viewed by 9422
Abstract
The authors wish to make the following corrections to this paper [1]: [...] Full article
3063 KiB  
Review
Photoresponsive Block Copolymers Containing Azobenzenes and Other Chromophores
by Haifeng Yu and Takaomi Kobayashi
Molecules 2010, 15(1), 570-603; https://doi.org/10.3390/molecules15010570 - 26 Jan 2010
Cited by 73 | Viewed by 14508
Abstract
Photoresponsive block copolymers (PRBCs) containing azobenzenes and other chromophores can be easily prepared by controlled polymerization. Their photoresponsive behaviors are generally based on photoisomerization, photocrosslinking, photoalignment and photoinduced cooperative motions. When the photoactive block forms mesogenic phases upon microphase separation of PRBCs, supramolecular [...] Read more.
Photoresponsive block copolymers (PRBCs) containing azobenzenes and other chromophores can be easily prepared by controlled polymerization. Their photoresponsive behaviors are generally based on photoisomerization, photocrosslinking, photoalignment and photoinduced cooperative motions. When the photoactive block forms mesogenic phases upon microphase separation of PRBCs, supramolecular cooperative motion in liquid-crystalline PRBCs enables them to self-organize into hierarchical structures with photoresponsive features. This offers novel opportunities to photocontrol microphase-separated nanostructures of well-defined PRBCs and extends their diverse applications in holograms, nanotemplates, photodeformed devices and microporous films. Full article
(This article belongs to the Special Issue Photochemistry in Organic Synthesis)
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2091 KiB  
Article
Structure, Morphology and Optical Properties of Chiral N-(4-X-phenyl)-N-[1(S)-1-phenylethyl]thiourea, X= Cl, Br, and NO2
by Werner Kaminsky, Donald Responte, Dan Daranciang, Jose B. Gallegos, Bao-Chau Ngoc Tran and Tram-Anh Pham
Molecules 2010, 15(1), 554-569; https://doi.org/10.3390/molecules15010554 - 26 Jan 2010
Cited by 9 | Viewed by 10943
Abstract
Three new enantiopure aryl-thioureas have been synthesized, N-(4-X-phenyl)-N-[1(S)-1-phenylethyl]thiourea, X= Cl, Br, and NO2 (compounds 1-3, respectively). Large single crystals of up to 0.5 cm3 were grown from methanol/ethanol solutions. Molecular structures were derived from X-ray [...] Read more.
Three new enantiopure aryl-thioureas have been synthesized, N-(4-X-phenyl)-N-[1(S)-1-phenylethyl]thiourea, X= Cl, Br, and NO2 (compounds 1-3, respectively). Large single crystals of up to 0.5 cm3 were grown from methanol/ethanol solutions. Molecular structures were derived from X-ray diffraction studies and the crystal morphology was compared to calculations employing the Bravais-Friedel, Donnay-Harker model. Molecular packing was further studied with Hirshfeld surface calculations. Semi-empirical classical model calculations of refractive indices, optical rotation and the electro-optic effect were performed with OPTACT on the basis of experimentally determined refractive indices. Compound 3 (space group P 1 (No. 1)) was estimated to possess a large electro-optic coefficient r333 of approximately 30 pm/V, whereas 1 and 2 (space Group P 21 (No. 4) exhibit much smaller effects. Full article
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536 KiB  
Article
Antiproliferative Effect and Ultrastructural Alterations Induced by Psilostachyin on Trypanosoma cruzi
by Valeria Sülsen, Patricia Barrera, Liliana Muschietti, Virginia Martino and Miguel Sosa
Molecules 2010, 15(1), 545-553; https://doi.org/10.3390/molecules15010545 - 25 Jan 2010
Cited by 25 | Viewed by 9239
Abstract
The effect of psilostachyin, a natural sesquiterpene lactone, on the growth and viability of cultured epimastigotes of Trypanosoma cruzi (Tulahuen) is reported. The antiproliferative effect was evaluated by counting the parasites in a Neubauer chamber and measuring their viability by using the dye [...] Read more.
The effect of psilostachyin, a natural sesquiterpene lactone, on the growth and viability of cultured epimastigotes of Trypanosoma cruzi (Tulahuen) is reported. The antiproliferative effect was evaluated by counting the parasites in a Neubauer chamber and measuring their viability by using the dye exclusion technique. The effect on parasite growth was irreversible at concentrations higher than 1.0 µg/mL and the addition of glutathione only partially blocked the effect of the compound. Moreover, we have studied the effects of this natural compound on parasite ultrastructure by transmission electron microscopy. Interestingly, psilostachyin induced ultrastructural alterations on the parasites at a concentration of 0.5 µg/mL, with important mitochondrial swelling and deformity of the kinetoplast. Full article
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212 KiB  
Article
Catalytic Asymmetric 1,4-Additions of β-Keto Esters to Nitroalkenes Promoted by a Bifunctional Homobimetallic Co2-Schiff Base Complex
by Makoto Furutachi, Zhihua Chen, Shigeki Matsunaga and Masakatsu Shibasaki
Molecules 2010, 15(1), 532-544; https://doi.org/10.3390/molecules15010532 - 22 Jan 2010
Cited by 33 | Viewed by 9598
Abstract
Catalytic asymmetric 1,4-addition of β-keto esters to nitroalkenes is described. 2.5 mol % of a homobimetallic Lewis acid/Brønsted base bifunctional Co2-Schiff base complex smoothly promoted the reaction in excellent yield (up to 99%), diastereoselectivity, and enantioselectivity (up to >30:1 dr and [...] Read more.
Catalytic asymmetric 1,4-addition of β-keto esters to nitroalkenes is described. 2.5 mol % of a homobimetallic Lewis acid/Brønsted base bifunctional Co2-Schiff base complex smoothly promoted the reaction in excellent yield (up to 99%), diastereoselectivity, and enantioselectivity (up to >30:1 dr and 98% ee). Catalyst loading was successfully reduced to 0.1 mol %. Mechanistic studies suggested that intramolecular cooperative functions of the two Co-metal centers are important for high catalytic activity and stereoselectivity. Full article
(This article belongs to the Special Issue Bifunctional Catalysis)
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461 KiB  
Article
Synthesis of Some New Mono- and Bis-Polycyclic Aromatic Spiro and Bis-Nonspiro-β-Lactams
by Aliasghar Jarrahpour and Edris Ebrahimi
Molecules 2010, 15(1), 515-531; https://doi.org/10.3390/molecules15010515 - 22 Jan 2010
Cited by 21 | Viewed by 9972
Abstract
Some new mono-and bis-polycyclic aromatic spiro-β-lactams and bis-non spiro-polycyclic aromatic β-lactams have been synthesized from imines derived from anthracene-9-carbaldehyde, 2-naphtaldehyde and a ketene derived from 9H-xanthene-9-carboxylic acid and phenoxyacetic acid by a [2+2] cycloaddition reaction. The cycloadducts were characterized by spectral data, including [...] Read more.
Some new mono-and bis-polycyclic aromatic spiro-β-lactams and bis-non spiro-polycyclic aromatic β-lactams have been synthesized from imines derived from anthracene-9-carbaldehyde, 2-naphtaldehyde and a ketene derived from 9H-xanthene-9-carboxylic acid and phenoxyacetic acid by a [2+2] cycloaddition reaction. The cycloadducts were characterized by spectral data, including 1H-NMR, 13C-NMR, IR and elemental analyses. The configurations of some of these mono-spiro-β-lactams were established by X-ray crystal analysis. Full article
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133 KiB  
Article
Synthesis and Antimicrobial Activity of New 5-(2-Thienyl)-1,2,4-triazoles and 5-(2-Thienyl)-1,3,4-oxadiazoles and Related Derivatives
by Mohamed A. Al-Omar
Molecules 2010, 15(1), 502-514; https://doi.org/10.3390/molecules15010502 - 22 Jan 2010
Cited by 43 | Viewed by 11535
Abstract
New 5-(2-thienyl)-1,2,4-triazoles and 5-(2-thienyl)-1,3,4-oxadiazoles namely, N-[3-mercapto-5-(2-thienyl)-1,2,4-triazol-4-yl]-N'-arylthioureas 4a–e, 2-arylamino-5-(2-thienyl)-1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles 5a–e, 3-arylaminomethyl-5-(2-thienyl)-1,3,4-oxadiazoline-2-thiones 7a–e, 3-(N-substituted anilinomethyl)-5-(2-thienyl)-1,3,4-oxadiazoline-2-thiones 8a, b and 3-(4-substituted-1-piperazinylmethyl)-5-(2-thienyl)-1,3,4-oxadiazoline-2-thiones 9a–f, were prepared. The synthesized compounds were tested for in vitro activities against certain strains [...] Read more.
New 5-(2-thienyl)-1,2,4-triazoles and 5-(2-thienyl)-1,3,4-oxadiazoles namely, N-[3-mercapto-5-(2-thienyl)-1,2,4-triazol-4-yl]-N'-arylthioureas 4a–e, 2-arylamino-5-(2-thienyl)-1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles 5a–e, 3-arylaminomethyl-5-(2-thienyl)-1,3,4-oxadiazoline-2-thiones 7a–e, 3-(N-substituted anilinomethyl)-5-(2-thienyl)-1,3,4-oxadiazoline-2-thiones 8a, b and 3-(4-substituted-1-piperazinylmethyl)-5-(2-thienyl)-1,3,4-oxadiazoline-2-thiones 9a–f, were prepared. The synthesized compounds were tested for in vitro activities against certain strains of Gram-positive and Gram-negative bacteria and the yeast-like pathogenic fungus Candida albicans. Compound 9a displayed marked broad spectrum antibacterial activity, while compounds 4d, 5e, 7b, 7c, 7d, 9b, 9c and 9d were highly active against the tested Gram-positive bacteria. None of the synthesized compounds were proved to be significantly active against Candida albicans. Full article
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2057 KiB  
Review
Total Synthesis of Annonaceous Acetogenins Belonging to the Non-Adjacent Bis-THF and Non-Adjacent THF-THP Sub-Classes
by Ian B. Spurr and Richard C. D. Brown
Molecules 2010, 15(1), 460-501; https://doi.org/10.3390/molecules15010460 - 21 Jan 2010
Cited by 33 | Viewed by 14022
Abstract
The synthesis of the subgroups of acetogenins containing non-adjacent bis-THF and non-adjacent THF-THP core units is reviewed. Specifically, total syntheses of gigantecin, 4-deoxygigantecin, cis-sylvaticin, squamostatin-C, squamostatin-D, sylvaticin and mucocin are discussed. Full article
(This article belongs to the Special Issue Acetogenins: Extraction, Synthesis and Biological Properties)
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634 KiB  
Review
Vitamin B6: A Molecule for Human Health?
by Hanjo Hellmann and Sutton Mooney
Molecules 2010, 15(1), 442-459; https://doi.org/10.3390/molecules15010442 - 20 Jan 2010
Cited by 172 | Viewed by 32413
Abstract
Vitamin B6 is an intriguing molecule that is involved in a wide range of metabolic, physiological and developmental processes. Based on its water solubility and high reactivity when phosphorylated, it is a suitable co-factor for many biochemical processes. Furthermore the vitamin is [...] Read more.
Vitamin B6 is an intriguing molecule that is involved in a wide range of metabolic, physiological and developmental processes. Based on its water solubility and high reactivity when phosphorylated, it is a suitable co-factor for many biochemical processes. Furthermore the vitamin is a potent antioxidant, rivaling carotenoids or tocopherols in its ability to quench reactive oxygen species. It is therefore not surprising that the vitamin is essential and unquestionably important for the cellular metabolism and well-being of all living organisms. The review briefly summarizes the biosynthetic pathways of vitamin B6 in pro- and eukaryotes and its diverse roles in enzymatic reactions. Finally, because in recent years the vitamin has often been considered beneficial for human health, the review will also sum up and critically reflect on current knowledge how human health can profit from vitamin B6. Full article
(This article belongs to the Special Issue Vitamins)
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125 KiB  
Article
In Vitro and in Vivo Effects of Three Different Mitragyna speciosa Korth Leaf Extracts on Phase II Drug Metabolizing Enzymes—Glutathione Transferases (GSTs)
by Juzaili Azizi, Sabariah Ismail, Mohd Nizam Mordi, Surash Ramanathan, Mohd Ikram Mohd Said and Sharif Mahsufi Mansor
Molecules 2010, 15(1), 432-441; https://doi.org/10.3390/molecules15010432 - 20 Jan 2010
Cited by 48 | Viewed by 12972
Abstract
In the present study, we investigate the effects of three different Mitragyna speciosa extracts, namely methanolic, aqueous and total alkaloid extracts, on glutathione transferase-specific activity in male Sprague Dawley rat liver cytosol in vitro and in vivo. In the in vitro study, [...] Read more.
In the present study, we investigate the effects of three different Mitragyna speciosa extracts, namely methanolic, aqueous and total alkaloid extracts, on glutathione transferase-specific activity in male Sprague Dawley rat liver cytosol in vitro and in vivo. In the in vitro study, the effect of Mitragyna speciosa extracts (0.01 to 750 µg/mL) against the specific activity of glutathione transferases was examined in rat liver cytosolic fraction from untreated rats. Our data show concentration dependent inhibition of cytosolic GSTs when Mitragyna speciosa extract was added into the reaction mixture. At the highest concentration used, the methanolic extract showed the highest GSTs specific activity inhibition (61%), followed by aqueous (50%) and total alkaloid extract (43%), respectively. In in vivo study, three different dosages; 50, 100 and 200 mg/kg for methanolic and aqueous extracts and 5, 10 and 20 mg/kg for total alkaloid extract were given orally for 14 days. An increase in GST specific activity was generally observed. However, only Mitragyna speciosa aqueous extract with a dosage of 100 mg/kg showed significant results: 129% compared to control. Full article
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305 KiB  
Article
Condensed Tannins from Mangrove Species Kandelia candel and Rhizophora mangle and Their Antioxidant Activity
by Liang-Liang Zhang, Yi-Ming Lin, Hai-Chao Zhou, Shu-Dong Wei and Jia-Hong Chen
Molecules 2010, 15(1), 420-431; https://doi.org/10.3390/molecules15010420 - 20 Jan 2010
Cited by 89 | Viewed by 15849
Abstract
The structures of condensed tannins isolated from two mangrove species, Kandelia candel and Rhizophora mangle, were characterized by 13C nuclear magnetic resonance (NMR) spectroscopy and matrix assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS) analyses. Results demonstrate that large heterogeneity occurs in [...] Read more.
The structures of condensed tannins isolated from two mangrove species, Kandelia candel and Rhizophora mangle, were characterized by 13C nuclear magnetic resonance (NMR) spectroscopy and matrix assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS) analyses. Results demonstrate that large heterogeneity occurs in degree of polymerization, pattern of hydroxylation, and substitution with monosaccharides in the structures of the condensed tannins. Condensed tannin oligomers from K. candel and R. mangle were shown to be heterogeneous mixtures consisting of procyanidin and prodelphinidin structural units with the former dominating. The MALDI-TOF mass spectra contained masses corresponding to a distinct oligomeric series of glycosylated heteropolyflavan units. In addition, condensed tannins from two mangrove plants were screened for their potential antioxidant activities using 1,1-diphenyl-2-picrylhydrazyl (DPPH) and ferric reducing antioxidant power (FRAP) model systems. Full article
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174 KiB  
Article
Gas-Phase Pyrolytic Reaction of 4-Aryl-3-buten-2-ols and Allyl Benzyl Ethers: Kinetic and Mechanistic Study
by Alya M. Al-Etaibi, Nouria A. Al-Awadi, Maher R. Ibrahim and Yehia A. Ibrahim
Molecules 2010, 15(1), 407-419; https://doi.org/10.3390/molecules15010407 - 20 Jan 2010
Cited by 2 | Viewed by 13493
Abstract
Flash vacuum pyrolysis (FVP) of 4-aryl-3-buten-2-ols [ArCH=CH-CH(CH3)OH, where Ar is phenyl, p-MeO, p-Me, p-Cl, p-NO2] gave the corresponding buta-1,3-dien-1-ylbenzene (ArCH=CH-CH=CH2, where Ar is Ph, p-MeO, p-Me, p-Cl, p-NO2 [...] Read more.
Flash vacuum pyrolysis (FVP) of 4-aryl-3-buten-2-ols [ArCH=CH-CH(CH3)OH, where Ar is phenyl, p-MeO, p-Me, p-Cl, p-NO2] gave the corresponding buta-1,3-dien-1-ylbenzene (ArCH=CH-CH=CH2, where Ar is Ph, p-MeO, p-Me, p-Cl, p-NO2) and 7-X-1,2-dihydronaphthalene derivatives (where X is H, MeO); FVP of 1-aryl-3-benzyloxy1-1-butenes and benzyl cinnamyl ethers [ArCH=CHCH(X)OCH2Ph, where Ar is phenyl, p-MeO, p-Me, p-Cl, X is H, Me, Ph] gave the corresponding but-2-en-1-ylbenzene derivatives (ArCH2CH=CH-X, where X is H, Me, Ph) together with benzaldehyde. The proposed mechanism of these pyrolytic transformations was supported by kinetic and product analysis. Full article
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422 KiB  
Article
Isolation, Synthesis and Structures of Ginsenoside Derivatives and Their Anti-Tumor Bioactivity
by Mei Han, Jin-Gang Hou, Cheng-Ming Dong, Wei Li, Hao-Lun Yu, Yi-Nan Zheng and Li Chen
Molecules 2010, 15(1), 399-406; https://doi.org/10.3390/molecules15010399 - 19 Jan 2010
Cited by 19 | Viewed by 10256
Abstract
Protopanaxatriol saponins obtained with AB-8 macroporous resin mainly consisted of ginsenosides Rg1 and Re. A novel mono-ester of ginsenoside-Rh1 (ginsenoside-ORh1) was synthesized through further enzymatic hydrolysis and octanoyl chloride modifications. A 53% yield was obtained by a facile synthetic [...] Read more.
Protopanaxatriol saponins obtained with AB-8 macroporous resin mainly consisted of ginsenosides Rg1 and Re. A novel mono-ester of ginsenoside-Rh1 (ginsenoside-ORh1) was synthesized through further enzymatic hydrolysis and octanoyl chloride modifications. A 53% yield was obtained by a facile synthetic method. The structures were identified on the basis of 1D-NMR and 2D-NMR, as well as ESI-TOF-MS mass spectroscopic analyses. The isolated and synthetic compounds were applied in an anti-tumor bioassay, in which ginsenoside ORh1 showed moderate effects on Murine H22 Hepatoma Cells. Full article
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1214 KiB  
Article
Luteolin Isolated from the Flowers of Lonicera japonica Suppresses Inflammatory Mediator Release by Blocking NF-κB and MAPKs Activation Pathways in HMC-1 Cells
by Ok-Hwa Kang, Jang-Gi Choi, John-Hwa Lee and Dong-Yeul Kwon
Molecules 2010, 15(1), 385-398; https://doi.org/10.3390/molecules15010385 - 18 Jan 2010
Cited by 114 | Viewed by 14939
Abstract
Luteolin (3′,4′,5,7-tetrahydroxylflavone) is a plant flavonoid and pharmacologically active agent that has been isolated from several plant species. In the present study, the effect of luteolin from the flowers of Lonicera japonica on phorbol 12-myristate 13-acetate (PMA) plus A23187-induced mast cell activation was [...] Read more.
Luteolin (3′,4′,5,7-tetrahydroxylflavone) is a plant flavonoid and pharmacologically active agent that has been isolated from several plant species. In the present study, the effect of luteolin from the flowers of Lonicera japonica on phorbol 12-myristate 13-acetate (PMA) plus A23187-induced mast cell activation was examined. Luteolin significantly inhibited the induction of inflammatory cytokines such as tumor necrosis factor (TNF)-α, interleukin (IL)-8, IL-6 and granulocyte-macrophage colony-stimulating factor (GM-CSF) by PMA plus A23187. Moreover, luteolin attenuated cyclooxygenase (COX)-2 expression and intracellular Ca2+ levels. In activated HMC-1 cells, the phosphorylation of extra-signal response kinase (ERK 1/2) and c-jun N-terminal Kinase (JNK 1/2), but not p38 mitogen-activated protein kinase (p38 MAPK) were decreased by treatment of the cells with luteolin. Luteolin inhibited PMA plus A23187-induced nuclear factor (NF)-κB activation, IκB degradation, and luciferase activity. Furthermore, luteolin suppressed the expression of TNF-α, IL-8, IL-6, GM-CSF, and COX-2 through a decrease in the intracellular Ca2+ levels, and also showed a suppression of the ERK 1/2, JNK 1/2, and NF-κB activation. These results indicated that luteolin from the flowers of Lonicera japonica exerted a regulatory effect on mast cell-mediated inflammatory diseases, such as RA, allergy disease and IBD. Full article
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138 KiB  
Article
A Simple Preparation of 2,3,4,6-Tetra-O-acyl-Gluco-, Galacto- and Mannopyranoses and Relevant Theoretical Study
by Zerong Daniel Wang, Yirong Mo, Chiao-Lun Chiou and Minghong Liu
Molecules 2010, 15(1), 374-384; https://doi.org/10.3390/molecules15010374 - 18 Jan 2010
Cited by 9 | Viewed by 17281
Abstract
The deacylation of glucose, galactose and mannose pentaacetates, galactose and mannose penta(3-bromo)benzoates, as well as the dealkylation of 2,3,4,6-tetra-O-acetyl and 2,3,4,6-tetra-O-(3-bromo)benzoyl methyl α-D-glucopyranosides have been studied. In addition, a computational study on the deacylation of β-D [...] Read more.
The deacylation of glucose, galactose and mannose pentaacetates, galactose and mannose penta(3-bromo)benzoates, as well as the dealkylation of 2,3,4,6-tetra-O-acetyl and 2,3,4,6-tetra-O-(3-bromo)benzoyl methyl α-D-glucopyranosides have been studied. In addition, a computational study on the deacylation of β-D-glucose pentaacetate has been carried out with density functional theory (B3LYP/6-31G*). The anomeric effect during deacetylation and dealkylation has been clearly demonstrated in both experimental and computational results. Full article
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489 KiB  
Review
Interest of Fluorescence Derivatization and Fluorescence Probe Assisted Post-column Detection of Phospholipids: A Short Review
by Hanadi Ibrahim, Eric Caudron, Athena Kasselouri and Pratrice Prognon
Molecules 2010, 15(1), 352-373; https://doi.org/10.3390/molecules15010352 - 18 Jan 2010
Cited by 21 | Viewed by 14705
Abstract
Phospholipids are essential constituents of all living cell membranes. There are many analytical methods available for the quantitative and qualitative determination of phospholipids, but since these molecules lack chromophores, common absorbance based methods are of limited use. Beside mass spectrometry, some less specific [...] Read more.
Phospholipids are essential constituents of all living cell membranes. There are many analytical methods available for the quantitative and qualitative determination of phospholipids, but since these molecules lack chromophores, common absorbance based methods are of limited use. Beside mass spectrometry, some less specific approaches that are routinely used are evaporative light scattering detection or fluorescence, which exhibit sufficient sensitivity. Here, we focus on fluorescence, which remains an interesting way to quantify phospholipids. Two ways of detecting phospholipids by fluorescence are possible coupled with separation techniques such as thin layer chromatography (TLC), high performance liquid chromatography (HPLC) and capillary electrophoresis (CE): firstly, pre-column derivatization procedures and secondly, probe assisted post-column detection with suitable fluorescence reagents. In both cases, the common purpose is to increase the detection sensitivity. It is shown that, whereas pre-column derivatization is characterized by selectivity due to the chemical functionality of the analyte involved in the derivatization process, in supramolecular post-column derivatization, the selectivity only proceeds from the capacity of the lipid to involve supramolecular assemblies with a fluorescence probe. The aim of this review is to summarize available experiments concerning fluorescence detection of phospholipids. The interest and limitation of such detection approaches are discussed. Full article
(This article belongs to the Special Issue Phospholipids)
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98 KiB  
Article
Identification and Comparative Quantification of Bio-Active Phthalides in Essential Oils from Si-Wu-Tang, Fo-Shou-San, Radix Angelica and Rhizoma Chuanxiong
by Yuping Tang, Min Zhu, Sheng Yu, Yongqing Hua, Jin-Ao Duan, Shulan Su, Xu Zhang, Yin Lu and Anwei Ding
Molecules 2010, 15(1), 341-351; https://doi.org/10.3390/molecules15010341 - 15 Jan 2010
Cited by 47 | Viewed by 13868
Abstract
Phthalides are important bio-active constituents in Si-Wu-Tang and Fo-Shou-San, two commonly used Traditional Chinese Medicine (TCM) combined prescriptions mainly derived from Radix Angelica and Rhizoma Chuanxiong. In this paper, the contents of eight phthalides, including Z-ligustilide, E-ligustilide, Z-butylenephthalide, E-butylene-phthalide, [...] Read more.
Phthalides are important bio-active constituents in Si-Wu-Tang and Fo-Shou-San, two commonly used Traditional Chinese Medicine (TCM) combined prescriptions mainly derived from Radix Angelica and Rhizoma Chuanxiong. In this paper, the contents of eight phthalides, including Z-ligustilide, E-ligustilide, Z-butylenephthalide, E-butylene-phthalide, 3-butylphthalide, neocnidilide and senkyunolide A were determined or estimated by gas chromatography–mass spectrometry (GC-MS). The results showed GC-MS was a simple, rapid, and high sensitive method for analyzing phthalides in Si-Wu-Tang, Fo-Shou-San, Radix Angelica and Rhizoma Chuanxiong, and the extractable contents of each phthalides including Z-ligustilide, E-ligustilide, Z-butylenephthalide, etc. varied after Radix Angelica, Rhizoma Chuanxiong were combined into a formulation, such as Si-Wu-Tang and Fo-Shou-San. Furthermore, inhibition activity of essential oils from Si-Wu-Tang, Fo-Shou-San, Radix Angelica and Rhizoma Chuanxiong on uterine contraction was tested in an in vitro assay, and the results showed that the activity of the essential oil is higher as the content of the phthalides increase, which demonstrated that phthalides are possibly main active components inhibiting mice uterine contraction in vitro. All of the results suggested that comparative analysis of chemical components and pharmacological activities of each herb and formula is possibly helpful to elucidate the active components in traditional Chinese medicine, and to reveal the compatibility mechanism of TCM formulae. Full article
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184 KiB  
Article
Substituted Pyrazinecarboxamides as Abiotic Elicitors of Flavolignan Production in Silybum marianum (L.) Gaertn Cultures in Vitro
by Lenka Tůmová, Jiří Tůma, Klara Megušar and Martin Doležal
Molecules 2010, 15(1), 331-340; https://doi.org/10.3390/molecules15010331 - 14 Jan 2010
Cited by 31 | Viewed by 13181
Abstract
Substituted pyrazinecarboxamides markedly influenced production of flavonolignans in Silybum marianum callus and suspension cultures. In this study the effect of two compounds, N-(3-iodo-4-methylphenyl)pyrazine-2-carboxamide (1) and N-(3-iodo-4-methylphenyl)-5-tert-butyl-pyrazine-2-carboxamide (2), as abiotic elicitors on flavono-lignan production in callus [...] Read more.
Substituted pyrazinecarboxamides markedly influenced production of flavonolignans in Silybum marianum callus and suspension cultures. In this study the effect of two compounds, N-(3-iodo-4-methylphenyl)pyrazine-2-carboxamide (1) and N-(3-iodo-4-methylphenyl)-5-tert-butyl-pyrazine-2-carboxamide (2), as abiotic elicitors on flavono-lignan production in callus culture of S. marianum was investigated. Silymarin complex compounds have hepatoprotective, anticancer and also hypocholesterolemic activity. In vitro flavonolignan concentration in cells is very low and the elicitation is one of the methods to increase production. Elicitors were tested at three concentrations and at different culture times. In the case of elicitation with 1, the greatest increase of flavonolignan and taxifoline production was observed at concentration c1a after 6-hours of elicitation and after 24 and 72-hours at concentration c1b. However, increased production of silychristin, one of the compounds in the silymarin complex, was achieved after only 6-hours elicitation with c1a (2.95 × 10-4 mol/L). The content of silychristin was 2-times higher compared to the control sample. An increased production of silychristin was reached with compound 2 at the concentration c2 (2.53 × 10-3 mol/L) after 72 h of elicitation. The production of silychristin in this case was increased 12-times compared to control. Full article
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163 KiB  
Article
Analysis of the Main Nucleosides in Cordyceps Sinensis by LC/ESI-MS
by Jian-Wei Xie, Lan-Fang Huang, Wei Hu, Yun-Biao He and Kin Ping Wong
Molecules 2010, 15(1), 305-314; https://doi.org/10.3390/molecules15010305 - 13 Jan 2010
Cited by 34 | Viewed by 14105
Abstract
A sensitive, selective and reliable liquid chromatography-mass spectrometry coupled with electrospray ionization interface method for simultaneous separation and determination of thymine, adenine, adenosine and cordycepin in Cordyceps sinensis has been established. The optimum separation for these analytes was achieved using a gradient elution [...] Read more.
A sensitive, selective and reliable liquid chromatography-mass spectrometry coupled with electrospray ionization interface method for simultaneous separation and determination of thymine, adenine, adenosine and cordycepin in Cordyceps sinensis has been established. The optimum separation for these analytes was achieved using a gradient elution system and a 2.0 × 150 mm Shimadzu VP-ODS column. 2-Chloroadenosine was used as internal standard for this assay. [M+H]+ions at m/z 127, 136, 268, 252 and 302 were chosen and selective ion monitoring (SIM) mode was used for quantitative analysis of the four main nucleosides. The regression equations were linear in the range of 1.0–117.5 μg·mL-1 for thymine, 1.8-127.0 μg·mL-1 for adenine, 0.6-114.0 μg·mL-1 for adenosine and 0.5-107.5 μg·mL-1 for cordycepin. The limits of quantitation (LOQ) and detection (LOD) were 1.0 and 0.2 μg·mL-1 for thymine, 1.8 and 0.6 μg·mL-1 for adenine, 0.6 and 0.1 μg·mL-1 for adenosine and 0.5 and 0.1 μg·mL-1 for cordycepin, respectively. The recoveries of the four nucleosides ranged from 98.47 to 99.32%. The developed method was successfully used to determine nucleosides in Cordyceps sinensis from different sources. Full article
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178 KiB  
Article
Palladium(II)/Cationic 2,2’-Bipyridyl System as a Highly Efficient and Reusable Catalyst for the Mizoroki-Heck Reaction in Water
by Shao-Hsien Huang, Jun-Rong Chen and Fu-Yu Tsai
Molecules 2010, 15(1), 315-330; https://doi.org/10.3390/molecules15010315 - 12 Jan 2010
Cited by 59 | Viewed by 11755
Abstract
A water-soluble and air-stable Pd(NH3)2Cl2/cationic 2,2’-bipyridyl system was found to be a highly-efficient and reusable catalyst for the coupling of aryl iodides and alkenes in neat water using Bu3N as a base. The reaction was [...] Read more.
A water-soluble and air-stable Pd(NH3)2Cl2/cationic 2,2’-bipyridyl system was found to be a highly-efficient and reusable catalyst for the coupling of aryl iodides and alkenes in neat water using Bu3N as a base. The reaction was conducted at 140 °C in a sealed tube in air with a catalyst loading as low as 0.0001 mol % for the coupling of activated aryl iodides with butyl and ethyl acrylates, providing the corresponding products in good to excellent yields with very high turnover numbers. In the case of styrene, Mizoroki-Heck coupling products were obtained in good to high yields by using a greater catalyst loading (1 mol %) and TBAB as a phase-transfer agent. After extraction, the residual aqueous solution could be reused several times with only a slight decrease in its activity, making the Mizoroki-Heck reaction “greener”. Full article
(This article belongs to the Special Issue Heck Coupling)
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213 KiB  
Article
Investigating the Activity Spectrum for Ring-Substituted 8-Hydroxyquinolines
by Robert Musiol, Josef Jampilek, Jacek E. Nycz, Matus Pesko, James Carroll, Katarina Kralova, Marcela Vejsova, Jim O'Mahony, Aidan Coffey, Anna Mrozek and Jaroslaw Polanski
Molecules 2010, 15(1), 288-304; https://doi.org/10.3390/molecules15010288 - 12 Jan 2010
Cited by 46 | Viewed by 13871
Abstract
In this study, a series of fourteen ring-substituted 8-hydroxyquinoline derivatives were prepared. The synthesis procedures are presented. The compounds were analyzed using RP-HPLC to determine lipophilicity. They were tested for their activity related to inhibition of photosynthetic electron transport (PET) in spinach ( [...] Read more.
In this study, a series of fourteen ring-substituted 8-hydroxyquinoline derivatives were prepared. The synthesis procedures are presented. The compounds were analyzed using RP-HPLC to determine lipophilicity. They were tested for their activity related to inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. Primary in vitro screening of the synthesized compounds was also performed against four mycobacterial strains and against eight fungal strains. Several compounds showed biological activity comparable with or higher than the standards isoniazid or fluconazole. For all the compounds, the relationships between the lipophilicity and the chemical structure of the studied compounds are discussed. Full article
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174 KiB  
Article
Synthesis and Vasorelaxant and Platelet Antiaggregatory Activities of a New Series of 6-Halo-3-phenylcoumarins
by Elías Quezada, Giovanna Delogu, Carmen Picciau, Lourdes Santana, Gianni Podda, Fernanda Borges, Verónica García-Morales, Dolores Viña and Francisco Orallo
Molecules 2010, 15(1), 270-279; https://doi.org/10.3390/molecules15010270 - 12 Jan 2010
Cited by 70 | Viewed by 12117
Abstract
A series of 6-halo-3-hydroxyphenylcoumarins (resveratrol-coumarins hybrid derivatives) was synthesized in good yields by a Perkin reaction followed by hydrolysis. The new compounds were evaluated for their vasorelaxant activity in intact rat aorta rings pre-contracted with phenylephrine (PE), as well as for their inhibitory [...] Read more.
A series of 6-halo-3-hydroxyphenylcoumarins (resveratrol-coumarins hybrid derivatives) was synthesized in good yields by a Perkin reaction followed by hydrolysis. The new compounds were evaluated for their vasorelaxant activity in intact rat aorta rings pre-contracted with phenylephrine (PE), as well as for their inhibitory effects on platelet aggregation induced by thrombin in washed human platelets. These compounds concentration-dependently relaxed vascular smooth muscle and some of them showed a platelet antiaggregatory activity that was up to thirty times higher than that shown by trans-resveratrol and some other previously synthesized derivatives. Full article
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551 KiB  
Article
Comparison of Dissolution and Surface Reactions Between Calcite and Aragonite in L-Glutamic and L-Aspartic Acid Solutions
by Miyoung Ryu, Hwan Kim, Mihee Lim, Kwangsuk You and Jiwhan Ahn
Molecules 2010, 15(1), 258-269; https://doi.org/10.3390/molecules15010258 - 11 Jan 2010
Cited by 20 | Viewed by 10092
Abstract
We have investigated dissolution and surface reaction of calcite and aragonite in amino acid solutions of L-glutamic (L-glu) and L-aspartic acid (L-asp) at weak acidity of above pH 3. The surface reactions of calcite and aragonite were related with the dissolution. Calcite was [...] Read more.
We have investigated dissolution and surface reaction of calcite and aragonite in amino acid solutions of L-glutamic (L-glu) and L-aspartic acid (L-asp) at weak acidity of above pH 3. The surface reactions of calcite and aragonite were related with the dissolution. Calcite was dissolved in both solutions but the dissolution was limited by an adsorption of Ca-carboxylate salt. Aragonite was neither dissolved nor reacted in amino acid solutions because the crystal surface consisted of a hard to dissolve structure. Full article
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136 KiB  
Communication
Inhibition of Oxidation of Aqueous Emulsions of Omega-3 Fatty Acids and Fish Oil by Phloretin and Phloridzin
by H. P. Vasantha Rupasinghe and Afsana Yasmin
Molecules 2010, 15(1), 251-257; https://doi.org/10.3390/molecules15010251 - 11 Jan 2010
Cited by 58 | Viewed by 12329
Abstract
The antioxidant properties of two apple dihydrochalcones, namely phloretin and phloridzin, were evaluated and compared with those of α-tocopherol and butylated hydroxytoluene (BHT). The effects were studied in an oil-in-water emulsion system containing methyl linolenate (ML), methyl eicosapentaenoate (MEPA), and methyl docosahexaenoate (MDHA) [...] Read more.
The antioxidant properties of two apple dihydrochalcones, namely phloretin and phloridzin, were evaluated and compared with those of α-tocopherol and butylated hydroxytoluene (BHT). The effects were studied in an oil-in-water emulsion system containing methyl linolenate (ML), methyl eicosapentaenoate (MEPA), and methyl docosahexaenoate (MDHA) in which oxidation was initiated by the peroxyl radical generator 2,2-azobis(2-amidinopropane) dihydrochloride (AAPH) and in fish oil where oxidation was initiated thermally. In the emulsion system, phloretin (1 and 5 mM) completely inhibited the oxidation of ML tested as evidenced by the thiobarbituric acid reactive substances (TBARS) assay. Under the same conditions, phloridzin was less effective than phloretin, but still more effective than α-tocopherol. Both phloretin and phloridzin molecules had a marginal inhibitory effect against oxidation of fish oil induced by heating at 70 °C for 3 hours, when compared to BHT. These results indicate that phloretin and phloridzin have the potential to suppress lipid oxidation in polyunsaturated fatty acid (PUFA) containing foods. Full article
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135 KiB  
Article
Effects of Volatile Components and Ethanolic Extract from Eclipta prostrata on Proliferation and Differentiation of Primary Osteoblasts
by Xiong-Hao Lin, Yan-Bin Wu, Shan Lin, Jian-Wei Zeng, Pei-Yuan Zeng and Jin-Zhong Wu
Molecules 2010, 15(1), 241-250; https://doi.org/10.3390/molecules15010241 - 8 Jan 2010
Cited by 41 | Viewed by 15254
Abstract
Eclipta prostrata, an aromatic plant, is known in Chinese herbal medicine for the treatment of various kidney diseases. In the present study, the volatile components were isolated from the aerial parts of this plant by hydrodistillation and analysed by GC–MS. A total [...] Read more.
Eclipta prostrata, an aromatic plant, is known in Chinese herbal medicine for the treatment of various kidney diseases. In the present study, the volatile components were isolated from the aerial parts of this plant by hydrodistillation and analysed by GC–MS. A total of 55 compounds, which were the major part (91.7%) of the volatiles, were identified by matching mass spectra with a mass spectrum library (NIST 05.L). The main components were as follows: heptadecane (14.78%), 6,10,14-trimethyl-2-pentadecanone (12.80%), n-hexadecanoic acid (8.98%), pentadecane (8.68%), eudesma-4(14),11-diene (5.86%), phytol (3.77%), octadec-9-enoic acid (3.35%), 1,2-benzenedicarboxylic acid diisooctyl ester (2.74%), (Z,Z)-9,12-octadecadienoic acid (2.36%), (Z)-7,11-dimethyl-3-methylene-1,6,10-dodecatriene (2.08%) and (Z,Z,Z)-1,5,9,9-tetramethyl-1,4,7-cycloundecatriene (2.07%). The effects of volatile components and ethanolic extract from the aerial parts of this plant on the proliferation and differentiation of primary osteoblasts were evaluated by the MTT method and measuring the activity of alkaline phosphatase (ALP activity). Both volatile components and ethanolic extract (1 μg/mL to 100 μg/mL) significantly (p < 0.01) stimulated the proliferation and increased the ALP activity of primary osteoblasts. These results propose that E. prostrata can play an important role in osteoblastic bone formation, and may possibly lead to the development of bone-forming drugs. Full article
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193 KiB  
Article
Determination of the Volatile Composition in Essential Oil of Descurainia sophia (L.) Webb ex Prantl (Flixweed) by Gas Chromatography/Mass Spectrometry (GC/MS)
by Jing Li, Xingang Liu, Fengshou Dong, Jun Xu, Yongquan Zheng and Weili Shan
Molecules 2010, 15(1), 233-240; https://doi.org/10.3390/molecules15010233 - 8 Jan 2010
Cited by 31 | Viewed by 12860
Abstract
Exhaustive hydro-distillation of Descurainia sophia (L.) Webb ex Prantl (flixweed) collected from two different locations (Cangzhou city-Sample 1 and Beijing city-Sample 2) gave in both cases yellowish colored oils in 0.31 and 0.26% yield, respectively. Detailed chemical composition of the essential oils was [...] Read more.
Exhaustive hydro-distillation of Descurainia sophia (L.) Webb ex Prantl (flixweed) collected from two different locations (Cangzhou city-Sample 1 and Beijing city-Sample 2) gave in both cases yellowish colored oils in 0.31 and 0.26% yield, respectively. Detailed chemical composition of the essential oils was analyzed by GC and GC/MS, and forty and thirty-eight compounds were identified. The results indicated that the most abundant component of Sample 1were cis-β-ocimene (20.1%), menthol (11.27%), neoisomenthyl acetate (3.5%), alloaromadendrene (2.28%) and longicyclene (2.25%). Compared with the constituents of Sample 1, several chemical compounds such as 1,8-cineole, α-eudesmol, cis, trans-farnesol and β-pinene were not detected in Sample 2 although it was similarly dominated by cis-β-ocimene (17.12%), menthol (10.7%) and neoisomenthyl acetate (2.96%). Final analysis of the chemical constituents in the essential oils of the two samples showed similarity in their chemical composition, but the relative content of all shared chemical constituents in Sample 2 was lower than that in Sample 1. Full article
414 KiB  
Communication
Synthesis and Structure of D3h-Symmetric Triptycene Trimaleimide
by Cristiano Zonta, Ottorino De Lucchi, Anthony Linden and Martin Lutz
Molecules 2010, 15(1), 226-232; https://doi.org/10.3390/molecules15010226 - 7 Jan 2010
Cited by 9 | Viewed by 16043
Abstract
A new D3h symmetric triptycene derivative has been synthesized with the aim of obtaining molecules that are able to assemble into porous structures, and can be used in the development of new ligands. The synthesis involves a Diels-Alder reaction as the key [...] Read more.
A new D3h symmetric triptycene derivative has been synthesized with the aim of obtaining molecules that are able to assemble into porous structures, and can be used in the development of new ligands. The synthesis involves a Diels-Alder reaction as the key step, followed by an oxidation and the formation of a maleimide ring. Triptycene trimaleimide furnished single crystals which have been analyzed by means of X-ray diffraction. Full article
(This article belongs to the Special Issue Supramolecular Assembly)
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595 KiB  
Article
Screening and Improvement of an Anti-VEGF DNA Aptamer
by Yoshihiko Nonaka, Koji Sode and Kazunori Ikebukuro
Molecules 2010, 15(1), 215-225; https://doi.org/10.3390/molecules15010215 - 7 Jan 2010
Cited by 120 | Viewed by 14220
Abstract
To obtain an aptamer with a high affinity for vascular endothelial growth factor (VEGF), we focused on the receptor-binding domain (RBD) of VEGF as a target epitope. Three rounds of screening gave Vap7, which bound to the VEGF isoforms VEGF121 and VEGF [...] Read more.
To obtain an aptamer with a high affinity for vascular endothelial growth factor (VEGF), we focused on the receptor-binding domain (RBD) of VEGF as a target epitope. Three rounds of screening gave Vap7, which bound to the VEGF isoforms VEGF121 and VEGF165 with KD values of 1.0 nM and 20 nM, respectively. Moreover, Vap7 showed specificity within the VEGF family. Secondary structure predictions and circular dicrhoism suggested that Vap7 folds into a G-quadruplex structure. We obtained a mutant aptamer that contains only this region of the aptamer sequence. This truncated mutant (V7t1) bound to both VEGF121 and VEGF165 with KD values of 1.1 nM and 1.4 nM, respectively. Its sequence was 5'-TGTGGGGGTGGACGGGCCGGGTAGA-3', and it appeared to form a G-quadruplex structure. We also produced an aptamer heterodimer consisting of our previously derived aptamer (del5-1), which binds to the heparin-binding domain of VEGF, linked to V7t1. The resulting heterodimer bound strongly to VEGF165 with a KD value of 4.7 × 102 pM. Full article
(This article belongs to the Special Issue High-throughput Screening)
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215 KiB  
Article
Elucidating the Structure-Activity Relationships of the Vasorelaxation and Antioxidation Properties of Thionicotinic Acid Derivatives
by Supaluk Prachayasittikul, Orapin Wongsawatkul, Apilak Worachartcheewan, Chanin Nantasenamat, Somsak Ruchirawat and Virapong Prachayasittikul
Molecules 2010, 15(1), 198-214; https://doi.org/10.3390/molecules15010198 - 6 Jan 2010
Cited by 30 | Viewed by 11455
Abstract
Nicotinic acid, known as vitamin B3, is an effective lipid lowering drug and intense cutaneous vasodilator. This study reports the effect of 2-(1-adamantylthio)nicotinic acid (6) and its amide 7 and nitrile analog 8 on phenylephrine-induced contraction of rat thoracic [...] Read more.
Nicotinic acid, known as vitamin B3, is an effective lipid lowering drug and intense cutaneous vasodilator. This study reports the effect of 2-(1-adamantylthio)nicotinic acid (6) and its amide 7 and nitrile analog 8 on phenylephrine-induced contraction of rat thoracic aorta as well as antioxidative activity. It was found that the tested thionicotinic acid analogs 6-8 exerted maximal vasorelaxation in a dose-dependent manner, but their effects were less than acetylcholine (ACh)-induced nitric oxide (NO) vasorelaxation. The vasorelaxations were reduced, apparently, in both NG-nitro-L-arginine methyl ester (L-NAME) and indomethacin (INDO). Synergistic effects were observed in the presence of L-NAME plus INDO, leading to loss of vasorelaxation of both the ACh and the tested nicotinic acids. Complete loss of the vasorelaxation was noted under removal of endothelial cells. This infers that the vasorelaxations are mediated partially by endothelium-induced NO and prostacyclin. The thionicotinic acid analogs all exhibited antioxidant properties in both 2,2-diphenyl-1-picrylhydrazyl (DPPH) and superoxide dismutase (SOD) assays. Significantly, the thionicotinic acid 6 is the most potent vasorelaxant with ED50 of 21.3 nM and is the most potent antioxidant (as discerned from DPPH assay). Molecular modeling was also used to provide mechanistic insights into the vasorelaxant and antioxidative activities. The findings reveal that the thionicotinic acid analogs are a novel class of vasorelaxant and antioxidant compounds which have potential to be further developed as promising therapeutics. Full article
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161 KiB  
Review
Click Chemistry for the Synthesis of RGD-Containing Integrin Ligands
by Matteo Colombo and Aldo Bianchi
Molecules 2010, 15(1), 178-197; https://doi.org/10.3390/molecules15010178 - 6 Jan 2010
Cited by 41 | Viewed by 17810
Abstract
In the last few years click chemistry reactions, and in particular coppercatalyzed cycloadditions, have been used intensively for the preparation of new bioconjugate molecules and materials applicable to biomedical and pharmaceutical areas. This review will be focused on conjugates of the tripeptide Arg-Gly-Asp [...] Read more.
In the last few years click chemistry reactions, and in particular coppercatalyzed cycloadditions, have been used intensively for the preparation of new bioconjugate molecules and materials applicable to biomedical and pharmaceutical areas. This review will be focused on conjugates of the tripeptide Arg-Gly-Asp formed by means of click chemistry reactions. This sequence is a well known binding motif for specific transmembrane proteins and is involved in cellular adhesion to the extracellular matrix, allowing the selective recognition of the biomolecule or polymer in which it is incorporated. Full article
(This article belongs to the Special Issue Click Chemistry)
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