Structure-activity studies on the lycorine pharmacophore: A potent inducer of apoptosis in human leukemia cells

被引：89
|
作者：
McNulty, James [1 ]
Nair, Jerald J. [1 ]
Bastida, Jaume [2 ]
Pandey, Siyaram [3 ]
Griffin, Carly [3 ]
机构：
[1] McMaster Univ, Dept Chem, Hamilton, ON L8S 4M1, Canada
[2] Univ Barcelona, Fac Farm, Dept Nat Prod, E-08028 Barcelona, Spain
[3] Univ Windsor, Dept Chem & Biochem, Windsor, ON N9B 3P4, Canada
来源：
PHYTOCHEMISTRY | 2009年 / 70卷 / 07期
基金：
加拿大自然科学与工程研究理事会;
关键词：
Narcissus bujei; Amaryllidaceae; Lycorine; Apoptosis-induction; Anticancer agent; Alkaloid; AMARYLLIDACEAE ALKALOIDS; ANTIMALARIAL ALKALOIDS; BIOLOGICAL EVALUATION; PANCRATISTATIN; INHIBITORS; IDENTIFICATION; NARCICLASINE; REPLICATION; REFINEMENT; PLANTS;
D O I：
10.1016/j.phytochem.2009.04.012
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：
The direct chemoselective differential functionalization of the ring-C hydroxyl groups present in the Amaryllidaceae alkaloid lycorine is described allowing for selective manipulation of the 1,2-hydroxyl groups. A mini-library comprised of synthetic and natural lycorane alkaloids was prepared and their apoptosis-inducing activity investigated in human leukemia (Jurkat) cells. Further insights into the nature of this interesting apoptosis-inducing pharmacophore are described, including the requirement of both free hydroxyl groups in ring-C. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码：913 / 919
页数：7
相关论文
共 50 条
  • [1] Structure Activity Studies on the Crinane Alkaloid Apoptosis-inducing Pharmacophore
    McNulty, James
    Nair, Jerald J.
    Bastida, Jaume
    Pandey, Siyaram
    Griffin, Carly
    NATURAL PRODUCT COMMUNICATIONS, 2009, 4 (04) : 483 - 488
  • [2] Structure-activity studies on acetylcholinesterase inhibition in the lycorine series of Amaryllidaceae alkaloids
    McNulty, James
    Nair, Jerald J.
    Little, Jessamyn R. L.
    Brennan, John D.
    Bastida, Jaume
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (17) : 5290 - 5294
  • [3] Anti-Dengue-Virus Activity and Structure-Activity Relationship Studies of Lycorine Derivatives
    Wang, Peng
    Li, Lin-Feng
    Wang, Qing-Yin
    Shang, Lu-Qing
    Shi, Pei-Yong
    Yin, Zheng
    CHEMMEDCHEM, 2014, 9 (07) : 1522 - 1533
  • [4] Structure-activity studies on seco-pancratistatin analogs: Potent inhibitors of human cytochrome P450 3A4
    McNulty, James
    Nair, Jerald J.
    Singh, Mohini
    Crankshaw, Denis J.
    Holloway, Alison C.
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (19) : 5607 - 5612
  • [5] Structure-Activity Relationship Studies on Diversified Salicylamide Derivatives as Potent Inhibitors of Human Adenovirus Infection
    Xu, Jimin
    Berastegui-Cabrera, Judith
    Chen, Haiying
    Pachon, Jeronimo
    Zhou, Jia
    Sanchez-Cespedes, Javier
    JOURNAL OF MEDICINAL CHEMISTRY, 2020, 63 (06) : 3142 - 3160
  • [6] Lycorine induces apoptosis and down-regulation of Mcl-1 in human leukemia cells
    Liu, Xiao-shan
    Jiang, Jikai
    Jiao, Xiao-yang
    Wu, Ying-e
    Lin, Jing-hua
    Cai, Ying-mu
    CANCER LETTERS, 2009, 274 (01) : 16 - 24
  • [7] Structure-activity relationship study of E6 as a novel necroptosis inducer
    Mou, Jianfeng
    Park, Ann
    Cai, Yu
    Yuan, Junying
    Yuan, Chengye
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2015, 25 (15) : 3057 - 3061
  • [8] Discovery of biphenyl imidazole derivatives as potent antifungal agents: Design, synthesis, and structure-activity relationship studies
    Zhao, Dongmei
    Zhao, Shizhen
    Zhao, Liyu
    Zhang, Xiangqian
    Wei, Peng
    Liu, Chunchi
    Hao, Chenzhou
    Sun, Bin
    Su, Xin
    Cheng, Maosheng
    BIOORGANIC & MEDICINAL CHEMISTRY, 2017, 25 (02) : 750 - 758
  • [9] Development of a pharmacophore for cruzain using oxadiazoles as virtual molecular probes: quantitative structure-activity relationship studies
    de Souza, Anacleto S.
    de Oliveira, Marcelo T.
    Andricopulo, Adriano D.
    JOURNAL OF COMPUTER-AIDED MOLECULAR DESIGN, 2017, 31 (09) : 801 - 816
  • [10] Structure of PDE3A-SLFN12 complex and structure-based design for a potent apoptosis inducer of tumor cells
    Chen, Jie
    Liu, Nan
    Huang, Yinpin
    Wang, Yuanxun
    Sun, Yuxing
    Wu, Qingcui
    Li, Dianrong
    Gao, Shuanhu
    Wang, Hong-Wei
    Huang, Niu
    Qi, Xiangbing
    Wang, Xiaodong
    NATURE COMMUNICATIONS, 2021, 12 (01)
12345