Monosaccharide as a Central Scaffold Toward the Construction of Salicylate-Based Bidentate PTP1B Inhibitors via Click Chemistry
文献类型：期刊论文
| 作者 | Tang, Yan-Hui1,2,3; Hu, Min1,2,3; He, Xiao-Peng1,2,3; Fahnbulleh, Sando1,2,3; Li, Cui1,2,3; Gao, Li-Xin4; Sheng, Li4; Tang, Yun1,2,3; Li, Jia4 ; Chen, Guo-Rong1,2,3
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| 刊名 | BULLETIN OF THE KOREAN CHEMICAL SOCIETY
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| 出版日期 | 2011-03-20 |
| 卷号 | 32期号:3页码:1000-1006 |
| 关键词 | Monosaccharide Structural preference Click chemistry Protein tyrosine phosphatase 1B (PTP1B) inhibitor |
| ISSN号 | 0253-2964 |
| DOI | 10.5012/bkcs.2011.32.3.1000 |
| 文献子类 | Article |
| 英文摘要 | The discovery of carbohydrate-based bioactive compounds has recently received considerable interest in the drug development. This paper stresses on the application of 1-methoxy-O-glucoside as the central scaffold, whereas salicylic pharmacophores were introduced with diverse spatial orientations probing into the structural preference of an enzymatic target, i.e. protein tyrosine phosphatase 1B (PTP1B). By employing regioselective protection and deprotection strategy, 2,6-, 3,4-, 4,6- and 2,3-di-O-propynyl 1-methoxy-O-glucosides were previously synthesized and then coupled with azido salicylate via click chemistry in forming the desired bidentate salicylic glucosides with high yields. The inhibitory assay of the obtained triazolyl derivatives leads to the identification of the 2,3-disubstituted salicylic 1-methoxy-O-glucoside as the structurally privileged PTP1B inhibitor among this bidentate compound series with micromole-ranged IC50 value and reasonable selectivity over other homologous PTPs tested. In addition, docking simulation was conducted to propose a plausible binding mode of this authorized inhibitor with PTP1B. This research might furnish new insight toward the construction of structurally different bioactive compounds based on the monosaccharide scaffold. |
| WOS关键词 | TYROSINE-PHOSPHATASE 1B ; INSULIN SENSITIVITY ; ACID ; DERIVATIVES ; DISCOVERY ; AZIDES ; DRUGS ; MICE |
| 资助项目 | National Natural Science Foundation of China[20876045] ; National Natural Science Foundation of China[30801405] ; National Basic Research Program of China[2007CB914201] ; National Science & Technology Major Project of China[2009ZX09302-001] ; Shanghai Science and Technology Community[10410702700] ; Shanghai Science and Technology Community[09DZ2291200] ; Chinese Academy of Sciences[KSCX2-YW-R-168] ; Fundamental Research Funds for the Central Universities[WK1013002] ; French Embassy in Beijing, China[00000000] |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000288832700044 |
| 出版者 | KOREAN CHEMICAL SOC |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/278578]  |
| 专题 | 国家新药筛选中心 中科院受体结构与功能重点实验室 新药研究国家重点实验室 药物安全性评价中心 |
| 通讯作者 | Tang, Yun |
| 作者单位 | 1.E China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China; 2.E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China; 3.E China Univ Sci & Technol, Sch Pharm, Shanghai 200237, Peoples R China; 4.Chinese Acad Sci, Shanghai Inst Biol Sci, Shanghai Inst Mat Med, Natl Ctr Drug Screening,State Key Lab Drug Res, Shanghai 201203, Peoples R China |
| 推荐引用方式 GB/T 7714 | Tang, Yan-Hui,Hu, Min,He, Xiao-Peng,et al. Monosaccharide as a Central Scaffold Toward the Construction of Salicylate-Based Bidentate PTP1B Inhibitors via Click Chemistry[J]. BULLETIN OF THE KOREAN CHEMICAL SOCIETY,2011,32(3):1000-1006. |
| APA | Tang, Yan-Hui.,Hu, Min.,He, Xiao-Peng.,Fahnbulleh, Sando.,Li, Cui.,...&Chen, Guo-Rong.(2011).Monosaccharide as a Central Scaffold Toward the Construction of Salicylate-Based Bidentate PTP1B Inhibitors via Click Chemistry.BULLETIN OF THE KOREAN CHEMICAL SOCIETY,32(3),1000-1006. |
| MLA | Tang, Yan-Hui,et al."Monosaccharide as a Central Scaffold Toward the Construction of Salicylate-Based Bidentate PTP1B Inhibitors via Click Chemistry".BULLETIN OF THE KOREAN CHEMICAL SOCIETY 32.3(2011):1000-1006. |
入库方式： OAI收割
来源：上海药物研究所
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