Preparation and biological activity of taxol acetates

Wilfredo Mellado; Neal F. Magri; David G.I. Kingston; Renee Garcia-Arenas; George A. Orr; Susan Band Horwitz

doi:10.1016/0006-291X(84)91557-2

Preparation and biological activity of taxol acetates

Wilfredo Mellado, Neal F. Magri, David G.I. Kingston, Renee Garcia-Arenas, George A. Orr, Susan Band Horwitz

Molecular Pharmacology

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95 Scopus citations

Abstract

Synthesis and biological activity of 2′-acetyltaxol and 7-acetyltaxol are reported. Activity is measured in vivo by cytotoxicity toward the macrophage-like cell line J774.2, and in vitro by promotion of microtubule assembly in the absence of exogenous GTP. Addition of an acetyl moiety at C-2′ results in loss of in vitro activity but not cytotoxicity. The properties of 7-acetyltaxol are similar to those of taxol in its effects on cell replication and on in vitro microtubule polymerization. Therefore a free hydroxyl group at C-7 is not required for in vitro activity and this position is available for structural modifications.

Original language	English (US)
Pages (from-to)	329-336
Number of pages	8
Journal	Biochemical and Biophysical Research Communications
Volume	124
Issue number	2
DOIs	https://doi.org/10.1016/0006-291X(84)91557-2
State	Published - Oct 30 1984

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ASJC Scopus subject areas

Biophysics
Biochemistry
Molecular Biology
Cell Biology

Cite this

Mellado, W., Magri, N. F., Kingston, D. G. I., Garcia-Arenas, R., Orr, G. A., & Horwitz, S. B. (1984). Preparation and biological activity of taxol acetates. Biochemical and Biophysical Research Communications, 124(2), 329-336. https://doi.org/10.1016/0006-291X(84)91557-2

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AU - Horwitz, Susan Band

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AB - Synthesis and biological activity of 2′-acetyltaxol and 7-acetyltaxol are reported. Activity is measured in vivo by cytotoxicity toward the macrophage-like cell line J774.2, and in vitro by promotion of microtubule assembly in the absence of exogenous GTP. Addition of an acetyl moiety at C-2′ results in loss of in vitro activity but not cytotoxicity. The properties of 7-acetyltaxol are similar to those of taxol in its effects on cell replication and on in vitro microtubule polymerization. Therefore a free hydroxyl group at C-7 is not required for in vitro activity and this position is available for structural modifications.

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10.1016/0006-291X(84)91557-2