Preparation and biological activity of taxol acetates.
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.
D000470:Alkaloids / Q000138:chemical synthesis* / Q000633:toxicity; D000818:Animals; D002455:Cell Division / Q000187:drug effects; D002460:Cell Line; D006160:Guanosine Triphosphate / Q000494:pharmacology; D007202:Indicators and Reagents; D007700:Kinetics; D008264:Macrophages / Q000187:drug effects*; D009682:Magnetic Resonance Spectroscopy; D008870:Microtubules / Q000187:drug effects / Q000648:ultrastructure*; D017239:Paclitaxel / Q000031:analogs & derivatives*; D013329:Structure-Activity Relationship; D043823:Taxoids
D000470:Alkaloids; D007202:Indicators and Reagents; D043823:Taxoids; D006160:Guanosine Triphosphate; C043189:7-acetyltaxol; C043188:2'-acetyltaxol; D017239:Paclitaxel