Synthesis and evaluation of curcumin analogues as potential thioredoxin reductase inhibitors

被引:68
|
作者
Qiu, Xu [1 ]
Liu, Zhong [1 ]
Shao, Wei-Yan [1 ]
Liu, Xing [2 ]
Jing, Da-Ping [1 ]
Yu, Yan-Jun [1 ]
An, Lin-Kun [1 ]
Huang, Shi-Liang [1 ]
Bu, Xian-Zhang [1 ]
Huang, Zhi-Shu [1 ]
Gu, Lian-Quan [1 ]
机构
[1] Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangzhou 510275, Guangdong, Peoples R China
[2] Sun Yat Sen Univ, Zhongshan Sch Med, Guangzhou 510080, Guangdong, Peoples R China
关键词
curcumin derivatives; TrxR inhibitor; furan moiety;
D O I
10.1016/j.bmc.2008.07.054
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
Series of curcumin derivatives were synthesized; the inhibitory activities on thioredoxin reductase (TrxR) of all analogues were evaluated by DTNB assay in vitro. It is found that most of the analogues can inhibit TrxR in the low micromolar range; Structure-activity relationship analysis reveals that analogues with furan moiety have excellent inhibitory effect on TrxR in an irreversible manner, indicating that the furan moiety may serve as a possible pharmacophore during the interaction of curcumin analogues with TrxR. The effect of selected curcuminoids on growth of different TrxR overexpressed cancer cell lines was also investigated and discussed. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:8035 / 8041
页数:7
相关论文
共 50 条
  • [1] Synthesis and biological evaluation of novel palmarumycin analogues as inhibitors of the thioredoxin-thioredoxin reductase redox system.
    Wipf, P
    Lynch, SM
    Powis, G
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 226 : U63 - U63
  • [2] Design, synthesis, and evaluation of curcumin analogues as potential inhibitors of bacterial sialidase
    Kim, Bo Ram
    Park, Ji-Young
    Jeong, Hyung Jae
    Kwon, Hyung-Jun
    Park, Su-Jin
    Lee, In-Chul
    Ryu, Young Bae
    Lee, Woo Song
    JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2018, 33 (01) : 1256 - 1265
  • [3] Synthesis and Biological Evaluation of Unsymmetrical Curcumin Analogues as Tyrosinase Inhibitors
    Jiang, Yongfu
    Du, Zhiyun
    Xue, Guihua
    Chen, Qian
    Lu, Yujing
    Zheng, Xi
    Conney, Allan H.
    Zhang, Kun
    MOLECULES, 2013, 18 (04): : 3948 - 3961
  • [4] On the potential of thioredoxin reductase inhibitors for cancer therapy
    Urig, Sabine
    Becker, Katja
    SEMINARS IN CANCER BIOLOGY, 2006, 16 (06) : 452 - 465
  • [5] Synthesis of Xanthohumol Analogues and Discovery of Potent Thioredoxin Reductase Inhibitor as Potential Anticancer Agent
    Zhang, Baoxin
    Duan, Dongzhu
    Ge, Chunpo
    Yao, Juan
    Liu, Yaping
    Li, Xinming
    Fang, Jianguo
    JOURNAL OF MEDICINAL CHEMISTRY, 2015, 58 (04) : 1795 - 1805
  • [6] Synthesis, Biological Evaluation and Molecular Docking of Avicequinone C Analogues as Potential Steroid 5α-Reductase Inhibitors
    Karnsomwan, Wiranpat
    Netcharoensirisuk, Ponsawan
    Rungrotmongkol, Thanyada
    De-Eknamkul, Wanchai
    Chamni, Supakarn
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2017, 65 (03) : 253 - 260
  • [7] Biological evaluation of novel selenazole-based compounds as potential thioredoxin reductase inhibitors
    Li, Dong-Dong
    He, Jie
    Zeng, Hui-Hui
    APPLIED ORGANOMETALLIC CHEMISTRY, 2012, 26 (11) : 619 - 624
  • [8] Curcumin Analogues with Aldose Reductase Inhibitory Activity: Synthesis, Biological Evaluation, and Molecular Docking
    Kondhare, Dasharath
    Deshmukh, Sushma
    Lade, Harshad
    PROCESSES, 2019, 7 (07)
  • [9] Inhibition of thioredoxin reductase by curcumin analogs
    Lee, K. S.
    Liu, Z.
    Gu, L. Q.
    FREE RADICAL RESEARCH, 2006, 40 : S136 - S136
  • [10] Inhibition of thioredoxin reductase by curcumin analogs
    Liu, Zhong
    Du, Zhi-Yun
    Huang, Zhi-Shu
    Lee, Kin-Sing
    Gu, Lian-Quan
    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 2008, 72 (08) : 2214 - 2218