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

[21] Crystal structure of (1aS,2S,3R)-2-trimethylsilyl-1a,2,3,4-tetrahydro-1H-8b-aza-benzo[a]cyclopropa[c]cyclohepten-3-ol, C14H21NOSi -: Reply to Pretre and Turina
Gaynor, JW
O'Brien, JE
Rychik, J
Sanchez, GR
DeCampli, WM
Spray, TL
[J]. EUROPEAN JOURNAL OF CARDIO-THORACIC SURGERY, 2001, 20 (02) : 429 - 429
[22] 4 ALPHA-METHYL-24S-ETHYL-5 ALPHA-CHOLESTAN-3 BETA-OL AND 4 ALPHA-METHYL-24S-ETHYL-5 ALPHA-CHOLEST-8(14)-EN-3 BETA-OL, 2 NEW STEROLS FROM A CULTURED MARINE DINOFLAGELLATE
BOHLIN, L
KOKKE, WCM
FENICAL, W
DJERASSI, C
[J]. PHYTOCHEMISTRY, 1981, 20 (10) : 2397 - 2401
[23] Crystal and molecular structure of 3β-acetoxy-21-(2-hydroxy-2-methylpropoxy)-cholest-5-en-25-ol, the first "double side chain" cholesterol analogue investigated by X-ray diffraction
Galdecka, E
Galdecki, Z
Górkiewicz, Z
Kurek-Tyrlik, A
Makaev, FZ
Micha, J
Calverley, MJ
[J]. POLISH JOURNAL OF CHEMISTRY, 1999, 73 (03) : 547 - 555
[24] INHIBITORS OF STEROL SYNTHESIS - SYNTHESIS OF [2,4-H-3]5-ALPHA-CHOLEST-8(14)-ENE-(3-BETA-TRIOL,7-ALPHA-TRIOL,15-ALPHA-TRIOL AND [2,4-H-3]5-ALPHA-CHOLEST-8(14)-EN-3-BETA-OL-15-ONE
PARISH, EJ
SCHROEPFER, GJ
[J]. JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 1981, 18 (10): : 1429 - 1436
[25] 5ALPHA-CHOLEST-8(14)-EN-3BETA-OL-15-ONE, A POTENT INHIBITOR OF STEROL SYNTHESIS, REDUCES THE LEVELS OF ACTIVITY OF ENZYMES INVOLVED IN THE SYNTHESIS AND REDUCTION OF 3-HYDROXY-3-METHYLGLUTARYL COENZYME A IN CHO-K1 CELLS
MILLER, LR
PINKERTON, FD
SCHROEPFER, GJ
[J]. BIOCHEMISTRY INTERNATIONAL, 1980, 1 (03): : 223 - 228
[26] PREPARATION AND PURIFICATION OF LABELLED BETA-ADRENERGIC BLOCKING AGENTS .1. SYNTHESIS OF C-14 AND TRITIUM LABELLED 1-ISOPROPYLAMINO-3-(1-NAPHTHYLOXY)-PROPAN-2-OL HYDROCHLORIDE, (PROPRANOLOL HYDROCHLORIDE, INDERAL)
BURNS, J
[J]. JOURNAL OF LABELLED COMPOUNDS, 1970, 6 (01): : 45 - &
[27] Crystal structure of (3aS,4S,5R)-4-trimethylsilyl-3a,4,5,6-tetrahydro-3H-1,2,10b-triaza-benzo[e]azulen-5-ol, C14H21N3OSi
Ducray, R
Grosvalet, L
Ciufolini, MA
Perrin, M
[J]. ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 2001, 216 (03): : 347 - 348
[28] 5-substituted analogues of 3-hydroxymethyl-5-aziridinyl-1-methyl-2-[1H-indole-4,7-dione]prop-2-en-1-ol (E09, NSC 382459) and their regioisomers as hypoxia-selective agents: Structure-cytotoxicity in vitro
Jaffar, M
Naylor, MA
Robertson, N
Lockyer, SD
Phillips, RM
Everett, SA
Adams, GE
Stratford, IJ
[J]. ANTI-CANCER DRUG DESIGN, 1998, 13 (02): : 105 - 123
[29] Crystal structure of (9aRS,10SR,10aRS)-8-methoxy-10-methyl-1,2,3,5,7, 9a,10,10a-octahydropyrrolo[1,2-b]isoquinoline-10-ol,C14H21NO2
Gross, S
Brüdgam, I
Hartl, H
Reissig, HU
[J]. ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 2004, 219 (01): : 57 - 58
[30] Distribution of (7α)-21-[4-[(diethylamino) methyl]-2-methoxyphenoxy]-7-methyl-19-norpregna-1,3,5(10)-trien-3-ol-20-[14C]2-hydroxy-1,2,3-propanetricarboxylate([14C]TAS-108) and its metabolites after single oral administration to rats bearing 7,12-dimethylbenz(α) anthraceneinduced mammary tumor
Yamaya, H
Saeki, M
Yoshida, K
Shibata, J
Yano, S
Sato, Y
Takao, A
Shindo, T
Buzdar, AU
Nagayama, S
[J]. DRUG METABOLISM AND DISPOSITION, 2006, 34 (02) : 331 - 338

← 1 2 3 4 →