Discovery of a potent tubulin polymerization inhibitor: synthesis and evaluation of water-soluble prodrugs of benzophenone analog

Bioorg Med Chem Lett. 2010 Nov 1;20(21):6327-30. doi: 10.1016/j.bmcl.2010.05.060. Epub 2010 May 20.

Abstract

Prodrugs have proven to be very useful in enhancing aqueous solubility of sparingly water-soluble drugs, thereby increasing in vivo efficacy without a need of special excipients. In vitro and in vivo evaluations of a number of amino acid prodrugs of 1, a previously identified potent tubulin polymerization inhibitor and cytotoxic against various cancer cell lines led to the discovery of 3·HCl (l-valine attached) which is highly efficacious in mouse xenografts bearing human cancer. Pharmacokinetic analysis in rats revealed that compound 1 was released immediately upon administration of 3·HCl intravenously, with rapid clearance of 3·HCl indicating the effective cleavage of prodrug. Compound 3·HCl (CKD-516) has now been progressed to phase 1 clinical trial.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / pharmacology*
  • Benzophenones / chemical synthesis*
  • Benzophenones / pharmacokinetics
  • Benzophenones / pharmacology*
  • Cell Proliferation / drug effects
  • HL-60 Cells
  • Humans
  • Injections, Intravenous
  • Male
  • Mice
  • Mice, Inbred BALB C
  • Prodrugs / chemical synthesis*
  • Prodrugs / chemistry
  • Rats
  • Rats, Sprague-Dawley
  • Solubility
  • Tubulin / biosynthesis*
  • Tubulin Modulators / chemical synthesis*
  • Tubulin Modulators / pharmacokinetics
  • Tubulin Modulators / pharmacology*
  • Water
  • Xenograft Model Antitumor Assays

Substances

  • Antineoplastic Agents
  • Benzophenones
  • Prodrugs
  • Tubulin
  • Tubulin Modulators
  • Water