Anti-HBV and cytotoxic activities of pyranocoumarin derivatives

被引:96
|
作者
Su, Chung-Ren [1 ]
Yeh, Sheau Farn [2 ]
Liu, Chih Miem [2 ]
Damu, Amooru G. [1 ]
Kuo, Tsung-Hsiao [1 ]
Chiang, Po-Cheng [3 ]
Bastow, Kenneth F. [4 ]
Lee, Kuo-Hsiung [3 ]
Wu, Tian-Shung [1 ]
机构
[1] Natl Cheng Kung Univ, Dept Chem, Tainan 701, Taiwan
[2] Natl Yang Ming Univ, Inst Biochem & Mol Biol, Taipei 112, Taiwan
[3] Univ N Carolina, UNC Eshelman Sch Pharm, Nat Prod Res Labs, Chapel Hill, NC 27599 USA
[4] Univ N Carolina, UNC Eshelman Sch Pharm, Div Med Chem & Nat Prod, Chapel Hill, NC 27599 USA
关键词
Pyranocoumarin derivatives; Anti-HBV; Cytotoxic; CHRONIC HEPATITIS-B; VIRUS; COUMARINS; THERAPY; ROOT;
D O I
10.1016/j.bmc.2008.12.007
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Four natural pyranocoumarins clausenidin (1), nordentatin (2), clausarin (3), and xanthoxyletin (4) were isolated from the medicinal plant Clausena excavata. Recently, we found that 1 and 2 suppressed hepatitis B virus surface antigen in HepA2 cells, and in addition, 1-3 showed cytotoxic activity against four human cancer cell lines (A549, MCF7, KB, and KB-VIN). To explore the SAR of 1-4, 17 pyranocoumarin analogues (5-21) were designed and synthesized. Among these analogues, 5 and 10 were the most potent against hepatitis B virus with EC50 values of 1.14 and 1.34 mu M, respectively. The most interesting result in the cytotoxicity assay was the significant activity of 1, 5, and 6 against the multi-drug resistant cell line, KB-VIN, without activity against the KB cell line. These data suggest that these three compounds could be useful hits for developing MDR-inverse drugs. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6137 / 6143
页数:7
相关论文
共 50 条
  • [1] Chromone derivatives from Halenia elliptica and their anti-HBV activities
    Sun, Yu-wei
    Liu, Guang-ming
    Huang, Hai
    Yu, Pei-zhong
    PHYTOCHEMISTRY, 2012, 75 : 169 - 176
  • [2] Synthesis, structures and anti-HBV activities of derivatives of the glutarimide antibiotic cycloheximide
    Hui-fang Guo
    Yu-huan Li
    Hong Yi
    Tian Zhang
    Shu-qin Wang
    Pei-zhen Tao
    Zhuo-rong Li
    The Journal of Antibiotics, 2009, 62 : 639 - 642
  • [3] Synthesis, structures and anti-HBV activities of derivatives of the glutarimide antibiotic cycloheximide
    Guo, Hui-fang
    Li, Yu-huan
    Yi, Hong
    Zhang, Tian
    Wang, Shu-qin
    Tao, Pei-zhen
    Li, Zhuo-rong
    JOURNAL OF ANTIBIOTICS, 2009, 62 (11): : 639 - 642
  • [4] Synthesis and Anti-HBV Activities of the Indirect Galactopyranosyl Derivatives of Matijin-Su
    Xu Guangcan
    Yuan Jie
    Liu Qingchuan
    Huang Zhengming
    Liang Guangyi
    Xu Bixue
    CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2016, 37 (08): : 1451 - 1459
  • [5] Abietane Diterpenoids from Perovskia atriplicifolia and Their Anti-HBV Activities
    Jiang, Zhi-Yong
    Li, Zhong-Qiu
    Huang, Chao-Guan
    Zhou, Jun
    Hu, Qiu-Fen
    Liu, Wen-Xing
    Huang, Xiang-Zhong
    Wang, Wei
    Zhang, Li-Zhu
    Xia, Fu-Ting
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2015, 36 (02) : 623 - 627
  • [6] Anti-HBV activities of Streblus asper and constituents of its roots
    Chen, Hong
    Li, Jun
    Wu, Qiang
    Niu, Xiao-Tao
    Tang, Mao-Tong
    Guan, Xin-Lan
    Li, Jian
    Yang, Rui-Yun
    Deng, Sheng-Ping
    Su, Xiao-Jian
    FITOTERAPIA, 2012, 83 (04) : 643 - 649
  • [7] SYNTHESIS AND ANTI-HBV ACTIVITY OF 4-AMINOANTIPYRINE DERIVATIVES
    Abdel-Rahman, A. A. -H.
    Ahmed, A. H. A.
    Ramiz, M. M. M.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2010, 46 (01) : 72 - 78
  • [8] Synthesis and biological evaluation of esculetin derivatives as potential anti-HBV agents
    Ye, Zhen
    Zhao, Tong-Shi-Yao
    Li, Shan-Bin
    Zhou, Xian-Li
    Luo, Qin
    Qin, Jiang-Ke
    Liang, Cheng-Qin
    Wang, Ping
    Ge, Guang-Bo
    MEDICINAL CHEMISTRY RESEARCH, 2023, 32 (05) : 899 - 909
  • [9] Synthesis and biological evaluation of esculetin derivatives as potential anti-HBV agents
    Zhen Ye
    Tong-Shi-Yao Zhao
    Shan-Bin Li
    Xian-Li Zhou
    Qin Luo
    Jiang-Ke Qin
    Cheng-Qin Liang
    Ping Wang
    Guang-Bo Ge
    Medicinal Chemistry Research, 2023, 32 : 899 - 909