Design and synthesis of a beta-lactamase activated 5-fluorouracil prodrug

Bioorg Med Chem Lett. 2009 Feb 15;19(4):1261-3. doi: 10.1016/j.bmcl.2008.12.057. Epub 2008 Dec 24.

Abstract

An efficient synthesis of a 5-fluorouracil-cephalosporin prodrug is described for use against colorectal and other cancers in antibody and gene-directed therapies. The compound shows stability in aqueous media until specifically activated by beta-lactamase (betaL). The kinetic parameters of the 5-fluorouracil-cephalosporin conjugate were determined in the presence of Enterobacter cloacae P99 betaL (ECl betaL) revealing a K(m)=95.4 microM and V(max)=3.21 microMol min(-1) mg(-1). The data compare favorably to related systems that have been reported and enable testing of this prodrug against cancer cell lines in vitro and in vivo.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents* / chemical synthesis
  • Antineoplastic Agents* / chemistry
  • Antineoplastic Agents* / pharmacology
  • Cephalosporins / chemical synthesis
  • Cephalosporins / metabolism
  • Drug Screening Assays, Antitumor
  • Enterobacter cloacae / enzymology*
  • Fluorouracil* / analogs & derivatives
  • Fluorouracil* / chemical synthesis
  • Fluorouracil* / pharmacology
  • Prodrugs / chemical synthesis*
  • Prodrugs / chemistry
  • Prodrugs / pharmacology*
  • beta-Lactamases / immunology
  • beta-Lactamases / metabolism*

Substances

  • Antineoplastic Agents
  • Cephalosporins
  • Prodrugs
  • beta-Lactamases
  • Fluorouracil