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Interactions of laulimalide, peloruside, and their derivatives with the isoforms of β-tubulin

Publication: Canadian Journal of Chemistry
2 April 2013

Abstract

The investigational anticancer agents laulimalide and peloruside are known to exert an antimitotic effect on cells by binding to β-tubulin. The binding affinities of derivatives of laulimalide and peloruside to all known isoforms of human β-tubulin were calculated using molecular mechanical, molecular dynamical, and quantum mechanical methods. Several of the derivatives are predicted to have improved β-tubulin binding affinities compared to the parent structures. These results can form the starting point for developing laulimalide or peloruside derivatives with greater specificity for the particular β-tubulin isoforms, which are overexpressed in certain tumours.

Graphical Abstract

Résumé

Le laulimalide et le péloruside sont des agents anticancéreux de recherches qui sont connus pour exercer un effet antimitotique sur les cellules par fixation à la β-tubuline. Faisant appel à des méthodes de mécanique moléculaire, de dynamique moléculaire et de mécanique quantique, on a calculé d'une façon théorique les affinités de fixation des dérivés du laulimalide et du péloruside avec toutes les formes connues de la β-tubuline humaine. Il a été possible de prédire que plusieurs des dérivés ont des affinités améliorées de fixation de la β-tubuline lorsque comparées à ces des structures parentes. Ces résultats peuvent servir de point de départ pour développer des dérivés du laulimalide ou du péloruside qui auraient des spécificités supérieures par des isoformes particulières de β-tubulines qui seraient surexprimées dans certaines tumeurs. [Traduit par la Rédaction]

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Supplementary Material

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Information & Authors

Information

Published In

cover image Canadian Journal of Chemistry
Canadian Journal of Chemistry
Volume 91Number 7July 2013
Pages: 511 - 517

History

Received: 12 September 2012
Accepted: 19 October 2012
Version of record online: 2 April 2013

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Key Words

  1. peloruside
  2. laulimalide
  3. molecular mechanics
  4. molecular dynamics
  5. tubulin
  6. cancer

Mots-clés

  1. péloruside
  2. laulimalide
  3. mécanique moléculaire
  4. dynamique moléculaire
  5. tubuline
  6. cancer

Authors

Affiliations

Melissa M. Gajewski
Department of Chemistry, University of Alberta, Edmonton, AB, Canada.
Division of Experimental Oncology, Department of Oncology, University of Alberta, Edmonton, AB, Canada.
Jack A. Tuszynski
Division of Experimental Oncology, Department of Oncology, University of Alberta, Edmonton, AB, Canada.
Department of Physics, University of Alberta, Edmonton, AB, Canada.
Khaled Barakat*
Division of Experimental Oncology, Department of Oncology, University of Alberta, Edmonton, AB, Canada.
J. Torin Huzil
School of Pharmacy and Department of Applied Mathematics, University of Waterloo, Waterloo, ON, Canada.
Mariusz Klobukowski
Department of Chemistry, University of Alberta, Edmonton, AB, Canada.

Notes

*
On leave from the Department of Engineering Mathematics and Physics, Fayoum University, Fayoum, Egypt.
This article is part of a Special Issue dedicated to Professor Dennis Salahub in recognition of his contributions to theoretical and computational chemistry.

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