Isolation and structure of the cell growth inhibitory depsipeptides dolastatins 11 and 12

George Pettit; Yoshiaki Kamano; Haruhisa Kizu; Claude Dufresne; Cherry L. Herald; Roger J. Bontems; Jean M. Schmidt; Fred E. Boettner; Ronald A. Nieman

Isolation and structure of the cell growth inhibitory depsipeptides dolastatins 11 and 12

George Pettit, Yoshiaki Kamano, Haruhisa Kizu, Claude Dufresne, Cherry L. Herald, Roger J. Bontems, Jean M. Schmidt, Fred E. Boettner, Ronald A. Nieman

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Abstract

Two antineoplastic cyclic depsipeptides designated dolastatin 11(1) and dolastatin 12 (2) were isolated from the Indian Ocean sea hare Dolabella auricularia. Dolastatins 11 and 12 inhibited growth of the PS leukemia with ED₅₀ 2.7 × 10^-3 and 7.5 × 10^-2 μg/mL respectively. Detailed structural studies employing 400 MHz ¹H,¹H-COSY, ¹H,¹³C-COSY, NOE, and HMBC experiments (in addition to acid and base hydrolysis, followed by GC-MS analysis) led to structure 1 for dolastatin 11 and to structure 2 for dolastatin 12.

Original language	English (US)
Pages (from-to)	553-558
Number of pages	6
Journal	Heterocycles
Volume	28
Issue number	2
State	Published - Jan 1 1989

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ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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Pettit, G., Kamano, Y., Kizu, H., Dufresne, C., Herald, C. L., Bontems, R. J., Schmidt, J. M., Boettner, F. E., & Nieman, R. A. (1989). Isolation and structure of the cell growth inhibitory depsipeptides dolastatins 11 and 12. Heterocycles, 28(2), 553-558.

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title = "Isolation and structure of the cell growth inhibitory depsipeptides dolastatins 11 and 12",

abstract = "Two antineoplastic cyclic depsipeptides designated dolastatin 11(1) and dolastatin 12 (2) were isolated from the Indian Ocean sea hare Dolabella auricularia. Dolastatins 11 and 12 inhibited growth of the PS leukemia with ED50 2.7 × 10-3 and 7.5 × 10-2 μg/mL respectively. Detailed structural studies employing 400 MHz 1H,1H-COSY, 1H,13C-COSY, NOE, and HMBC experiments (in addition to acid and base hydrolysis, followed by GC-MS analysis) led to structure 1 for dolastatin 11 and to structure 2 for dolastatin 12.",

author = "George Pettit and Yoshiaki Kamano and Haruhisa Kizu and Claude Dufresne and Herald, {Cherry L.} and Bontems, {Roger J.} and Schmidt, {Jean M.} and Boettner, {Fred E.} and Nieman, {Ronald A.}",

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AU - Pettit, George

AU - Kamano, Yoshiaki

AU - Kizu, Haruhisa

AU - Dufresne, Claude

AU - Herald, Cherry L.

AU - Bontems, Roger J.

AU - Schmidt, Jean M.

AU - Boettner, Fred E.

AU - Nieman, Ronald A.

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AB - Two antineoplastic cyclic depsipeptides designated dolastatin 11(1) and dolastatin 12 (2) were isolated from the Indian Ocean sea hare Dolabella auricularia. Dolastatins 11 and 12 inhibited growth of the PS leukemia with ED50 2.7 × 10-3 and 7.5 × 10-2 μg/mL respectively. Detailed structural studies employing 400 MHz 1H,1H-COSY, 1H,13C-COSY, NOE, and HMBC experiments (in addition to acid and base hydrolysis, followed by GC-MS analysis) led to structure 1 for dolastatin 11 and to structure 2 for dolastatin 12.

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Isolation and structure of the cell growth inhibitory depsipeptides dolastatins 11 and 12

Abstract

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