Synthesis, Modeling, and Anti-Tubulin Activity of a D-Seco Paclitaxel Analogue

Luciano Barboni, Guido Giarlo, Massimo Ricciutelli, Roberto Ballini, Gunda I. Georg, David G. VanderVelde, Richard H. Himes, Minmin Wang, Ami Lakdawala, James P. Snyder

Research output: Contribution to journalArticlepeer-review

30 Scopus citations


(Equation presented) We have previously described a model of paclitaxel-microtubule binding that led to the prediction that analogues of paclitaxel lacking any D ring could stabilize microtubules as well as paclitaxel if the substituent present at C4 did not have unfavorable steric interactions with the binding pocket. We report the synthesis of a 4-methyl paclitaxel analogue, compound 1, which bears this prediction out. Compound 1 is as potent as paclitaxel at microtubule stabilization in vitro; however, it has only about one-four-hundredth the cytotoxicity of paclitaxel.

Original languageEnglish (US)
Pages (from-to)461-464
Number of pages4
JournalOrganic Letters
Issue number4
StatePublished - Feb 19 2004


Dive into the research topics of 'Synthesis, Modeling, and Anti-Tubulin Activity of a D-Seco Paclitaxel Analogue'. Together they form a unique fingerprint.

Cite this