| Title | Facile preparation and characterization of novel oleanane-type triterpene functionalized beta-cyclodextrin conjugates |
| Authors | Jiao, Pingxuan Wang, Shouxin Liang, Shuobin Li, Man Gao, Qianqian Ji, Dezhong Chen, Yingying Li, Haiwei Ran, Fuxiang Zhang, Yongmin Zhang, Lihe Zhou, Demin Xiao, Sulong |
| Affiliation | Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Yunnan, Peoples R China Jining Med Univ, Sch Pharm, Rizhao 276826, Peoples R China Sorbonne Univ, Inst Parisien Chim Mol, CNRS UMR 8232, 4 Pl Jussieu, F-75005 Paris, France |
| Keywords | beta-Cyclodextrin DIBAL-H Oleanolic acid Echinocystic acid Synthesis |
| Issue Date | 2019 |
| Publisher | CHINESE CHEMICAL LETTERS |
| Abstract | Oleanolic acid (OA) and echinocystic acid (EA), two naturally occurring pentacyclic oleanane triterpenes, are gaining increasing attention due to their promising pharmacological activities. Conjugation with amphiphilic alpha(beta)-cyclodextrin (CD) via "click chemistry" can improve their solubility and anti-HCV entry potency. In the present work, four water-soluble beta-CD-pentacyclic triterpene conjugates were designed and synthesized, in which OA and EA was coupled to one of the primary hydroxyl groups of beta-CD via ester and amide bonds. The structures of the conjugates were unambiguously determined by H-1 NMR, C-13 NMR and HRMS or MALDI-TOF-MS. All the conjugates showed lower hydrophobicity (AlogP) than their parent compounds and no significant cytotoxicity was found to HL-60, A549, Hela and Bel-7402 cells at concentrations up to 10 mu mol/L. Further anti-HCV entry activity and mechanism studies are under way in our laboratory. (C) 2018 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved. |
| URI | http://hdl.handle.net/20.500.11897/550188 |
| ISSN | 1001-8417 |
| DOI | 10.1016/j.cclet.2018.10.009 |
| Indexed | SCI(E) EI |
| Appears in Collections: | 药学院 天然药物与仿生药物国家重点实验室 |
