A-ring modified betulinic acid derivatives as potent cancer preventive agents

被引：8
|
作者：
Hung, Hsin-Yi [1 ,5 ]
Nakagawa-Goto, Kyoko [1 ,2 ]
Tokuda, Harukuni [3 ]
Iida, Akira [4 ]
Suzuki, Nobutaka [3 ]
Bori, Ibrahim D. [1 ]
Qian, Keduo [1 ]
Lee, Kuo-Hsiung [1 ,5 ]
机构：
[1] Univ N Carolina, Eshelman Sch Pharm, Nat Prod Res Labs, Chapel Hill, NC 27599 USA
[2] Kanazawa Univ, Grad Sch Nat Sci & Technol, Div Pharmaceut Sci, Kanazawa, Ishikawa 9201192, Japan
[3] Kanazawa Univ, Clin R&D Grad Sch Med Sci, Dept Complementary & Alternat Med, Kanazawa, Ishikawa 9208640, Japan
[4] Kinki Univ, Fac Agr, Nara 6318505, Japan
[5] China Med Univ & Hosp, Chinese Med Res & Dev Ctr, Taichung 401, Taiwan
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2014年 / 24卷 / 03期
关键词：
Betulinic acid; seco A-ring; Chemopreventive; EBV-EA; BARR-VIRUS ACTIVATION; DESIGN;
D O I：
10.1016/j.bmcl.2013.12.041
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
Ten new 3,4-seco betulinic acid (BA) derivatives were designed and synthesized. Among them, compounds 7-15 exhibited enhanced chemopreventive ability in an in vitro short-term 12-O-tetradecanoylphorbol- 13-acetate (TPA) induced Epstein-Barr virus early antigen (EBV-EA) activation assay in Raji cells. Specifically, analogs with a free C-28 carboxylic acid, including 7, 8, 11, and 13, inhibited EBV-EA activation significantly. The most potent compound 8 displayed 100% inhibition at 1 x 10(3) mol ratio/TPA and 73.4%, 35.9%, and 8.4% inhibition at 5 x 10(2), 1 x 10(2), and 1 x 10 mol ratio/TPA, respectively, comparable with curcumin at high concentration and better than curcumin at low concentration. The potent chemopreventive activity of novel seco A-ring BAs (8 and 11) was further confirmed in an in vivo mouse skin carcinogenesis assay. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1005 / 1008
页数：4
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