Structure Activity Studies on the Crinane Alkaloid Apoptosis-inducing Pharmacophore

被引:0
|
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
基金
加拿大自然科学与工程研究理事会;
关键词
Alkaloid; Amaryllidaceae; Crinane; Apoptosis; Cytotoxicity; SOUTH-AFRICAN AMARYLLIDACEAE; PANCRATISTATIN; HYMENOCALLIS; REFINEMENT; INHIBITORS; PLANTS; BULBS; CELLS;
D O I
暂无
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The apoptosis-inducing ability of alpha-ethano bridged crinane alkaloids was investigated using natural and semi-synthetic derivatives uncovering novel structural requirements of this cytotoxic pharmacophore. An alpha-ethano bridge is required; an alpha- or beta-methoxy or hydroxyl H-bond acceptor are all tolerated at C-3; a small substituent (H, or OH) alone is tolerated at C-11; and a C-1 to C-2 double bond is shown to modulate, but is not a requirement for, apoptosis-inducing activity.
引用
收藏
页码:483 / 488
页数:6
相关论文
共 50 条
  • [21] Antioxidant and apoptosis-inducing actiities of ellagic acid
    Han, Dong Hoon
    Lee, Min Jeon
    Kim, Jeong Hee
    ANTICANCER RESEARCH, 2006, 26 (5A) : 3601 - 3606
  • [22] Relationship between ascorbyl radical intensity and apoptosis-inducing activity
    Sakagami, H
    Satoh, K
    Ohata, H
    Takahashi, H
    Yoshida, H
    Iida, M
    Kuribayashi, N
    Sakagami, T
    Momose, K
    Takeda, M
    ANTICANCER RESEARCH, 1996, 16 (5A) : 2635 - 2644
  • [23] Synthesis of Oxovanadium Complexes and Their Apoptosis-Inducing Activity in Leukemia Cells
    Yamaguchi, Tomoko
    Watanabe, Shinya
    Matsumura, Yuriko
    Tokuoka, Yoshikazu
    Yokoyama, Akihiro
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2012, 60 (04) : 508 - 512
  • [24] Structure and function of bak gene and its apoptosis-inducing mechanism
    Li, Y
    Qi, YP
    Xiao, GF
    CHINESE SCIENCE BULLETIN, 1999, 44 (07): : 605 - 609
  • [25] Dissociating the dual roles of apoptosis-inducing factor in maintaining mitochondrial structure and apoptosis
    Cheung, Eric C. C.
    Joza, Nicholas
    Steenaart, Nancy A. E.
    McClellan, Kelly A.
    Neuspiel, Margaret
    McNamara, Stephen
    MacLaurin, Jason G.
    Rippstein, Peter
    Park, David S.
    Shore, Gordon C.
    McBride, Heidi M.
    Penninger, Josef M.
    Slack, Ruth S.
    EMBO JOURNAL, 2006, 25 (17): : 4061 - 4073
  • [27] Synthesis and Biological Evaluation of Styrylheterocycles Analogs of Resveratrol as Apoptosis-Inducing Agents
    Antonioletti, Roberto
    Righi, Giuliana
    Ricelli, Alessandra
    Rossetti, Ilaria
    Viglianti, Angela
    Frezza, Caterina
    Marino-Merlo, Francesca
    Macchi, Beatrice
    CURRENT ORGANIC CHEMISTRY, 2017, 21 (10) : 939 - 948
  • [28] Dipterocarpol in Oleoresin of Dipterocarpus alatus Attributed to Cytotoxicity and Apoptosis-Inducing Effect
    Puthongking, Ploenthip
    Yongram, Chawalit
    Katekaew, Somporn
    Sungthong, Bunleu
    Weerapreeyakul, Natthida
    MOLECULES, 2022, 27 (10):
  • [29] Synthesis and antiproliferative and apoptosis-inducing activity of novel 3-substituted-3-hydroxy-2-oxindole compounds
    Moghaddam, Mona Nazemi
    Jalal, Razieh
    Zeraatkar, Zohreh
    IN VITRO CELLULAR & DEVELOPMENTAL BIOLOGY-ANIMAL, 2018, 54 (01) : 61 - 70
  • [30] Novel Naphthalimide-Benzoic Acid Conjugates as Potential Apoptosis-Inducing Agents: Design, Synthesis, and Biological Activity
    Wu, Aibin
    Mei, Ping
    Xu, Yufang
    Qian, Xuhong
    CHEMICAL BIOLOGY & DRUG DESIGN, 2011, 78 (06) : 941 - 947