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癌症预防剂9. 桦木酸衍生物作为有效的癌症化学预防剂。

Cancer preventive agents 9. Betulinic acid derivatives as potent cancer chemopreventive agents.

作者信息

Nakagawa-Goto Kyoko, Yamada Koji, Taniguchi Masahiko, Tokuda Harukuni, Lee Kuo-Hsiung

机构信息

Natural Products Research Laboratories, Eshelman School of Pharmacy, University of North Carolina, Chapel Hill, NC 27599, USA.

出版信息

Bioorg Med Chem Lett. 2009 Jul 1;19(13):3378-81. doi: 10.1016/j.bmcl.2009.05.050. Epub 2009 May 18.

DOI:10.1016/j.bmcl.2009.05.050
PMID:19481937
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2747314/
Abstract

C-3 esterifications of betulinic acid (BA, 1) and its A-ring homolog, ceanothic acid (CA, 2), were carried out to provide sixteen terpenoids, 4-19, including nine new compounds (4-12). All synthesized compounds were evaluated in an in vitro antitumor-promoting assay using the Epstein-Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells. Among them, compounds 4-6, 11-14, 16, and 17 displayed remarkable inhibitory effects of EBV-EA activation. BA analog 6, which contains a prenyl-like group, showed the most potent inhibitory effect (100%, 76%, 37%, and 11% inhibition of EBA activation at 1000, 500, 100, and 10mol ratio/TPA, respectively, with IC(50) value of 285mol ratio/32pmol TPA). Compound 6 merits further development as a cancer preventive agent.

摘要

对桦木酸（BA，1）及其A环同系物ceanothic酸（CA，2）进行了C-3酯化反应，得到了16种萜类化合物，4-19，其中包括9种新化合物（4-12）。使用12-O-十四烷酰佛波醇-13-乙酸酯（TPA）诱导Raji细胞中的爱泼斯坦-巴尔病毒早期抗原（EBV-EA）激活，在体外抗肿瘤促进试验中对所有合成化合物进行了评估。其中，化合物4-6、11-14、16和17对EBV-EA激活表现出显著的抑制作用。含有类异戊二烯基的BA类似物6表现出最有效的抑制作用（在1000、500、100和10mol比/TPA时，分别对EBA激活有100%、76%、37%和11%的抑制作用，IC(50)值为285mol比/32pmol TPA）。化合物6作为一种癌症预防剂值得进一步开发。

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