Separation and peroxisome proliferator-activated receptor-gamma agonist activity evaluation of synthetic racemic bavachinin enantiomers
文献类型：期刊论文
| 作者 | Du, Guoxin2; Feng, Li2; Yang, Zhuo1; Shi, Jiye3; Huang, Cheng2; Guo, Fujiang2; Li, Bo1; Zhu, Weiliang1 ; Li, Yiming2
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| 刊名 | BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
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| 出版日期 | 2015-06-15 |
| 卷号 | 25期号:12页码:2579-2583 |
| 关键词 | Bavachinin PPAR-gamma Supercritical fluid chromatography Binding assay Molecular docking |
| ISSN号 | 0960-894X |
| DOI | 10.1016/j.bmcl.2015.04.029 |
| 文献子类 | Article |
| 英文摘要 | Bavachinin, isolated from Psoralea corylifolia seeds, has been reported to demonstrate peroxisome proliferator- activated receptor-gamma (PPAR-gamma) agonist activity. However, isolated bavachinin is actually a mixture of S and R configurations, with an enantiomeric excess value of approximately 24.3%. For further study on the structure-activity relationships of bavachinin, investigating the PPAR-gamma agonist activity of the two enantiomers is crucial. Considering the limited availability, racemic bavachinin was prepared in this study using chemical synthesis. The enantiomers of racemic bavachinin were then separated using supercritical fluid chromatography. This concise strategy yielded (S)- and (R)-bavachinin in optical purity as high as >= 97.5%. The PPAR-gamma agonist activity of the two enantiomers was evaluated using a time-resolved fluorescence resonance energy transfer-based competitive binding assay method; IC50 values of (S)-and (R)-bavachinin were 616.7 and 471.2 nM, respectively. The interaction between the compounds and PPAR-gamma was further explored using a molecular docking method. This study suggests that (S)-and (R)-bavachinin demonstrate similar PPAR-gamma agonist activities. (C) 2015 Elsevier Ltd. All rights reserved. |
| WOS关键词 | SUPERCRITICAL-FLUID CHROMATOGRAPHY ; PSORALEA-CORYLIFOLIA ; CHIRAL FLAVANONES ; DERIVATIVES ; HESPERETIN ; NARINGENIN ; CANCER ; ALPHA |
| 资助项目 | National Natural Science Foundation of China[81173518] ; Eastern Scholar Tracking Program of Shanghai Municipal Education Commission[2012-90] ; International Collaboration Project[2014DFA31130] ; Program of Shanghai E-institute of Bioactive Constituents in Traditional Chinese Medicine[00000000] |
| WOS研究方向 | Pharmacology & Pharmacy ; Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000355147300026 |
| 出版者 | PERGAMON-ELSEVIER SCIENCE LTD |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/276492]  |
| 专题 | 药物发现与设计中心 天然药物化学研究室 |
| 通讯作者 | Zhu, Weiliang |
| 作者单位 | 1.Chinese Acad Sci, Key Lab Receptor Res, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China; 2.Shanghai Univ Tradit Chinese Med, Sch Pharm, Shanghai 201203, Peoples R China; 3.UCB Pharma, Dept Informat, Slough SL1 4EN, Berks, England |
| 推荐引用方式 GB/T 7714 | Du, Guoxin,Feng, Li,Yang, Zhuo,et al. Separation and peroxisome proliferator-activated receptor-gamma agonist activity evaluation of synthetic racemic bavachinin enantiomers[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS,2015,25(12):2579-2583. |
| APA | Du, Guoxin.,Feng, Li.,Yang, Zhuo.,Shi, Jiye.,Huang, Cheng.,...&Li, Yiming.(2015).Separation and peroxisome proliferator-activated receptor-gamma agonist activity evaluation of synthetic racemic bavachinin enantiomers.BIOORGANIC & MEDICINAL CHEMISTRY LETTERS,25(12),2579-2583. |
| MLA | Du, Guoxin,et al."Separation and peroxisome proliferator-activated receptor-gamma agonist activity evaluation of synthetic racemic bavachinin enantiomers".BIOORGANIC & MEDICINAL CHEMISTRY LETTERS 25.12(2015):2579-2583. |
入库方式： OAI收割
来源：上海药物研究所
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