Selective, covalent modification of beta-tubulin residue Cys-239 by T138067, an antitumor agent with in vivo efficacy against multidrug-resistant tumors

Proc Natl Acad Sci U S A. 1999 May 11;96(10):5686-91. doi: 10.1073/pnas.96.10.5686.

Abstract

Microtubules are linear polymers of alpha- and beta-tubulin heterodimers and are the major constituents of mitotic spindles, which are essential for the separation of chromosomes during mitosis. Here we describe a synthetic compound, 2-fluoro-1-methoxy-4-pentafluorophenylsulfonamidobenzene (T138067), which covalently and selectively modifies the beta1, beta2, and beta4 isotypes of beta-tubulin at a conserved cysteine residue, thereby disrupting microtubule polymerization. Cells exposed to T138067 become altered in shape, indicating a collapse of the cytoskeleton, and show an increase in chromosomal ploidy. Subsequently, these cells undergo apoptosis. Furthermore, T138067 exhibits cytotoxicity against tumor cell lines that exhibit substantial resistance to vinblastine, paclitaxel, doxorubicin, and actinomycin D. T138067 is also equally efficacious in inhibiting the growth of sensitive and multidrug-resistant human tumor xenografts in athymic nude mice. These observations suggest that T138067 may be clinically useful for the treatment of multidrug-resistant tumors.

Publication types

  • Comparative Study

MeSH terms

  • Animals
  • Antineoplastic Agents / pharmacology*
  • Apoptosis / drug effects
  • Cell Cycle / drug effects
  • Cysteine / chemistry*
  • Cytoskeleton / drug effects
  • Drug Resistance, Multiple
  • Humans
  • Leukemia, Lymphoid / drug therapy
  • Mice
  • Mice, Nude
  • Microtubules / metabolism
  • Molecular Structure
  • Neoplasm Transplantation
  • Paclitaxel / pharmacology
  • Protein Binding
  • Sulfonamides / chemical synthesis
  • Sulfonamides / pharmacology*
  • Tubulin / chemistry*
  • Tumor Cells, Cultured
  • Vinblastine / pharmacology

Substances

  • Antineoplastic Agents
  • Sulfonamides
  • Tubulin
  • Vinblastine
  • Cysteine
  • Paclitaxel
  • batabulin