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Pure and Applied Chemistry

The Scientific Journal of IUPAC

Ed. by Burrows, Hugh / Stohner, Jürgen

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1365-3075
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Volume 84, Issue 6

Issues

Conformationally constrained and nanoparticle-targeted paclitaxels

David G. I. Kingston / Lawrence Tamarkin / Giulio F. Paciotti
Published Online: 2012-02-09 | DOI: https://doi.org/10.1351/PAC-CON-11-09-02

Paclitaxel (Taxol®) is one of the most important anticancer agents developed over the last 30 years. Its primary mechanism of action is by interaction with the cellular protein tubulin, causing irreversible polymerization to microtubules. A detailed knowledge of this crucial interaction is thus of paramount importance in the design and development of highly potent analogs and also for the potential development of “non-taxane” tubulin polymerization agents. This review briefly describes the discovery and development of taxol, and then describes our work on delineating the tubulin-binding conformation of paclitaxel by a combination of rotational echo double resonance (REDOR) NMR and molecular modeling. The resulting “T-taxol” conformation was validated by the synthesis of conformationally constrained paclitaxel analogs, which had bioactivities up to 20-fold higher than those of paclitaxel. The review concludes with recent work on the development of a gold nanoparticle derivative of paclitaxel. This delivery method has the potential to lower the dosage of paclitaxel needed while maintaining or increasing its effectiveness, thus significantly improving the benefits of this important chemotherapeutic agent.

Keywords: gold nanoparticles; natural products; paclitaxel

Conference

International Symposium on the Chemistry of Natural Products and the 7th International Conference on Biodiversity (ISCNP-27 & ICOB-7), International Conference on Biodiversity, International Symposium on the Chemistry of Natural Products, ICOB, ISCNP, Biodiversity, Natural Products, 27th, Brisbane, Australia, 2011-07-10–2011-07-15

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About the article

Published Online: 2012-02-09

Published in Print: 2012-02-09


Citation Information: Pure and Applied Chemistry, Volume 84, Issue 6, Pages 1455–1467, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: https://doi.org/10.1351/PAC-CON-11-09-02.

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