Participation of the β-hydroxyketone part for potent cytotoxicity of callystatin A, a spongean polyketide

被引：38

作者：

Murakami, N ^{[1
]}

Sugimoto, M ^{[1
]}

Kobayashi, M ^{[1
]}

机构：

[1] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2001年 / 9卷 / 01期

关键词：

D O I：

10.1016/S0968-0896(00)00220-0

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The participation of the beta -hydroxyketone part of callystatin A in the potent cytotoxicity was analyzed through the analogue-syntheses and the assessment of their biological potencies. The ketonic carbonyl, the 19-hydroxyl, and the three asymmetric methyl groups located in the beta -hydroxyketone part of callystatin A were revealed to contribute to the cytotoxic potency, respectively. Moreover, the alpha,beta -unsaturated delta -lactone portion was shown to serve as a conclusive functional group for the cytotoxic activity. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：57 / 67

页数：11

共 21 条

[1] READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES [J].

DESS, DB ;

MARTIN, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :4155-4156

[2] Investigation of the chemo- and stereoselectivity of the ketene-Claisen rearrangement [J].

Ernst, B ;

Gonda, J ;

Jeschke, R ;

Nubbemeyer, U ;

Oehrlein, R ;

Bellus, D .

HELVETICA CHIMICA ACTA, 1997, 80 (03) :876-891

[3] LEPTOMYCIN-A AND LEPTOMYCIN-B NEW ANTI-FUNGAL ANTIBIOTICS .2. STRUCTURE ELUCIDATION [J].

HAMAMOTO, T ;

SETO, H ;

BEPPU, T .

JOURNAL OF ANTIBIOTICS, 1983, 36 (06) :646-650

[4] NEW ANTITUMOR ANTIBIOTICS, ANGUINOMYCIN-A AND ANGUINOMYCIN-B [J].

HAYAKAWA, Y ;

ADACHI, K ;

KOMESHIMA, N .

JOURNAL OF ANTIBIOTICS, 1987, 40 (09) :1349-1352

[5] Studies on new antitumor antibiotics, leptofuranins A, B, C and D .2. Physicochemical properties and structure elucidation [J].

Hayakawa, Y ;

Sohda, KY ;

Seto, H .

JOURNAL OF ANTIBIOTICS, 1996, 49 (10) :980-984

[6] MOLECULAR SIEVE-ASSISTED OXIDATIONS - NEW METHODS FOR CARBOHYDRATE DERIVATIVE OXIDATIONS [J].

HERSCOVICI, J ;

ANTONAKIS, K .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (12) :561-562

[7] Absolute stereostructure and total synthesis of leptomycin B [J].

Kobayashi, M ;

Wang, WQ ;

Tsutsui, Y ;

Sugimoto, M ;

Murakami, N .

TETRAHEDRON LETTERS, 1998, 39 (45) :8291-8294

[8] Callystatin A, a potent cytotoxic polyketide from the marine sponge, Callyspongia truncata [J].

Kobayashi, M ;

Higuchi, K ;

Murakami, N ;

Tajima, H ;

Aoki, S .

TETRAHEDRON LETTERS, 1997, 38 (16) :2859-2862

[9] STRUCTURAL STUDY OF A NEW ANTITUMOR ANTIBIOTIC, KAZUSAMYCIN [J].

KOMIYAMA, K ;

OKADA, K ;

OKA, H ;

TOMISAKA, S ;

MIYANO, T ;

FUNAYAMA, S ;

UMEZAWA, I .

JOURNAL OF ANTIBIOTICS, 1985, 38 (02) :220-223

[10] Leptomycin B inhibition of signal-mediated nuclear export by direct binding to CRM1 [J].

Kudo, N ;

Wolff, B ;

Sekimoto, T ;

Schreiner, EP ;

Yoneda, Y ;

Yanagida, M ;

Horinouchi, S ;

Yoshida, M .

EXPERIMENTAL CELL RESEARCH, 1998, 242 (02) :540-547

← 1 2 3 →