Synthesis of MeON-neoglycosides of digoxigenin with 6-deoxy- and 2,6-dideoxy-D-glucose derivatives and their anticancer activity
文献类型：期刊论文
| 作者 | Wang, Dong-dong2; Li, Xiao-san2; Bao, Yu-zhou4; Liu, Jie4; Zhang, Xiao-kun4; Yao, Xin-sheng2; Sun, Xue-Long1,5; Tang, Jin-Shan2,3 |
| 刊名 | BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
 |
| 出版日期 | 2017-08-01 |
| 卷号 | 27期号:15页码:3359-3364 |
| 关键词 | Digoxigenin MeON-glycosylation Deoxy-sugar Anticancer Nur77 nuclear receptor |
| ISSN号 | 0960-894X |
| DOI | 10.1016/j.bmcl.2017.06.008 |
| 文献子类 | Article |
| 英文摘要 | Cardiac glycosides show anticancer activities and their deoxy-sugar chains are vital for their anticancer effects. In order to study the structure-activity relationship (SAR) of cardiac glycosides toward cancers and get more potent anticancer agents, a series of MeON-neoglycosides of digoxigenin was synthesized and evaluated. First, ten 6-deoxy- and 2,6-dideoxy-D-glucopyranosyl donors were synthesized starting from methyl a-D-glucopyranoside and 2-deoxy-D-glucose. Meanwhile, the digoxigenin was obtained by acidic hydrolysis of commercially available digoxin as glycosyl acceptor. Then, a 22-member MeON-neoglycoside library of digoxigenin was successfully synthesized by neoglycosylation method. Finally, the induction of Nur77 expression and its translocation from the nucleus to cytoplasm together with cytotoxicity of these MeON-neoglycosides were evaluated. The SAR analysis revealed that C3 glycosylation is required for their induction of Nur77 expression. Moreover, some MeON-neoglycosides (2b and 8b) could significant induce the expression of Nur77 and its translocation from the nucleus to cytoplasm. However, these compounds showed no inhibitory effects on the proliferation of cancer cells, suggesting that they may not induce apoptosis of NIH-H460 cancer cells and their underlying potential and application toward cancer cells deserves future study. (C) 2017 Elsevier Ltd. All rights reserved. |
| WOS关键词 | CARDIAC-GLYCOSIDES ; NATURAL-PRODUCTS ; NEOGLYCORANDOMIZATION ; DIGITOXIN |
| 资助项目 | National Natural Science Foundation of China[81673320] ; National Natural Science Foundation of China[81502406] ; State Key Laboratory of Drug Research[SIMM1601KF-09] ; National 111 Project of China[B13038] ; Fujian young teacher education research project[JA14009] |
| WOS研究方向 | Pharmacology & Pharmacy ; Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000405106500027 |
| 出版者 | PERGAMON-ELSEVIER SCIENCE LTD |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/272549]  |
| 专题 | 新药研究国家重点实验室 中科院受体结构与功能重点实验室 |
| 通讯作者 | Tang, Jin-Shan |
| 作者单位 | 1.Cleveland State Univ, Ctr Gene Regulat Hlth & Dis GRHD, 2121 Euclid Ave, Cleveland, OH 44115 USA; 2.Jinan Univ, Inst Tradit Chinese Med & Nat Prod, Coll Pharm, Guangzhou 510632, Guangdong, Peoples R China; 3.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China 4.Xiamen Univ, Sch Pharmaceut Sci, Xiamen 361005, Peoples R China; 5.Cleveland State Univ, Dept Chem Chem & Biomed Engn, 2121 Euclid Ave, Cleveland, OH 44115 USA; |
| 推荐引用方式 GB/T 7714 | Wang, Dong-dong,Li, Xiao-san,Bao, Yu-zhou,et al. Synthesis of MeON-neoglycosides of digoxigenin with 6-deoxy- and 2,6-dideoxy-D-glucose derivatives and their anticancer activity[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS,2017,27(15):3359-3364. |
| APA | Wang, Dong-dong.,Li, Xiao-san.,Bao, Yu-zhou.,Liu, Jie.,Zhang, Xiao-kun.,...&Tang, Jin-Shan.(2017).Synthesis of MeON-neoglycosides of digoxigenin with 6-deoxy- and 2,6-dideoxy-D-glucose derivatives and their anticancer activity.BIOORGANIC & MEDICINAL CHEMISTRY LETTERS,27(15),3359-3364. |
| MLA | Wang, Dong-dong,et al."Synthesis of MeON-neoglycosides of digoxigenin with 6-deoxy- and 2,6-dideoxy-D-glucose derivatives and their anticancer activity".BIOORGANIC & MEDICINAL CHEMISTRY LETTERS 27.15(2017):3359-3364. |
入库方式： OAI收割
来源：上海药物研究所
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