Facile preparation and characterization of novel oleanane-type triterpene functionalized β-cyclodextrin conjugates

Facile preparation and characterization of novel oleanane-type triterpene functionalized β-cyclodextrin conjugates

论文摘要

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 α(β)-cyclodextrin(CD) via "click chemistry" can improve their solubility and anti-HCV entry potency. In the present work,four water-soluble β-CD-pentacyclic triterpene conjugates were designed and synthesized, in which OA and EA was coupled to one of the primary hydroxyl groups of β-CD via ester and amide bonds. The structures of the conjugates were unambiguously determined by 1H NMR, 13C 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 μmol/L. Further anti-HCV entry activity and mechanism studies are under way in our laboratory.

论文目录

文章来源

类型: 期刊论文

作者: Pingxuan Jiao,Shouxin Wang,Shuobin Liang,Man Li,Qianqian Gao,Dezhong Ji,Yingying Chen,Haiwei Li,Fuxiang Ran,Yongmin Zhang,Lihe Zhang,Demin Zhou,Sulong Xiao

来源: Chinese Chemical Letters 2019年03期

年度: 2019

分类: 工程科技Ⅰ辑

专业: 有机化工

单位: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University,School of Pharmacy, Jining Medical University,Sorbonne Universite, Institut Parisien de Chimie Moleculaire, CNRS UMR 8232,State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences

基金: supported by the National Natural Science Foundation of China (Nos. 81573269,21572015,21877007,91753202 and 21702007),and the open funding of the State Key Laboratory of Phytochemistry and Plant Resources in West China

分类号: TQ460.1

页码: 690-693

总页数: 4

文件大小: 675K

下载量: 12

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Facile preparation and characterization of novel oleanane-type triterpene functionalized β-cyclodextrin conjugates
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