Conjugates of 3α-methoxyserrat-14-en-21β-ol (PJ-1) and 3β-methoxyserrat-14-en-21β-ol (PJ-2) as cancer chemopreventive agents

被引：3

作者：

Tanaka, Reiko ^{[1
]}

Tsujii, Hiroko ^{[1
]}

Yamada, Takeshi ^{[1
]}

Kajimoto, Tetsuya ^{[1
]}

Tokuda, Harukuni ^{[2
]}

Arai, Takanari ^{[2
]}

Suzuki, Nobutaka ^{[2
]}

Hasegawa, Junya ^{[3
]}

Hamashima, Yoshio ^{[3
]}

Node, Manabu ^{[3
]}

机构：

[1] Osaka Univ Pharmaceut Sci, Med Chem Lab, Osaka 5691094, Japan

[2] Kanazawa Univ, R&D Grad Sch Med Sci, Dept Complementary & Alternat Med, Kanazawa, Ishikawa 9208640, Japan

[3] Kyoto Pharmaceut Univ, Dept Pharmaceut Mfg Chem, Yamashina Ku, Kyoto 6078414, Japan

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2011年 / 46卷 / 08期

关键词：

3 alpha-methoxyserrat-14-en-21 beta-ol (PJ-1); 3 beta-methoxyserrat-14-en-21 beta-ol (PJ-2); 3,3-dimethyl-succinyl derivatives; Epstein-Barr virus early antigen (EBV-EA) activation; In vivo two-stage mouse-skin carcinogenesis test; SERRATANE-TYPE TRITERPENOIDS; ANTITUMOR AGENTS; ACID; FLAVONOIDS; HYBRIDS;

D O I：

10.1016/j.ejmech.2011.04.062

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

3 alpha-Methoxyserrat-14-en-21 beta-ol (PJ-1) and 3 beta-methoxyserrat-14-en-21 beta-ol (PJ-2) were conjugated with well-known phenolic compounds, narigenin, hesperetin, genistein, and daidzein (1-8). Other conjugates of PJ-2-3,5-dihydroxy-4-methoxybenzoic acid (9), PJ-2 pyrogallol (10), and derivatives of PJ-1, PJ-2-3,3-dimethyl-succinates (11, 12), PJ-1, PJ-2 succinates (13, 14), PJ-2 glycine (15), PJ-2 piperidine acetic acid (16), and PJ-1 epoxy-3,3-dimethyl-succinate (17) were tested for their inhibitory effects on Epstein Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA). The inhibitory effects of 11 (IC50 = 251),12 (IC50 = 248), and 17 (IC50= 230 mol ratio/32 pmol/TPA), were 2-fold stronger than those of the other compounds such as oleanolic acid (IC50 = 449). Compounds 10, 11, and 17 inhibited mouse skin tumor promotion in an in vivo two-stage carcinogenesis model. The in vivo two-stage mouse-skin carcinogenesis test employed 7,12-dimethylbenz[a]anthracene (DMBA) as an initiator and TPA as a promoter. (C) 2011 Elsevier Masson SAS. All rights reserved.

引用

页码：3368 / 3375

页数：8

共 31 条

[31] Discovery of Kinase Spectrum Selective Macrocycle (16E)-14-Methyl-20-oxa-5,7,14,26-tetraazatetracyclo[19.3.1.1(2,6).1(8,12)]heptacosa-1(25),2(26),3,5,8(27),9,11,16,21,23-decaene (SB1317/TG02), a Potent Inhibitor of Cyclin Dependent Kinases (CDKs), Janus Kinase 2 (JAK2), and Fms-like Tyrosine Kinase-3 (FLT3) for the Treatment of Cancer
William, Anthony D.
Lee, Angeline C. -H.
Goh, Kee Chuan
Blanchard, Stephanie
Poulsen, Anders
Teo, Ee Ling
Nagaraj, Harish
Lee, Chai Ping
Wang, Haishan
Williams, Meredith
Sun, Eric T.
Hu, Changyong
Jayaraman, Ramesh
Pasha, Mohammed Khalid
Ethirajulu, Kantharaj
Wood, Jeanette M.
Dymock, Brian W.
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (01) : 169 - 196

← 1 2 3 4 →