Discovery of matrix metalloproteases selective and activated peptide-doxorubicin prodrugs as anti-tumor agents

Bioorg Med Chem Lett. 2010 Feb 1;20(3):853-6. doi: 10.1016/j.bmcl.2009.12.084. Epub 2010 Jan 4.

Abstract

To selectively target doxorubicin (Dox) to tumor tissue and thereby improve the therapeutic index and/or efficacy of Dox, matrix metalloproteinases (MMP) activated peptide-Dox prodrugs were designed and synthesized by coupling MMP-cleavable peptides to Dox. Preferred conjugates were good substrates for MMPs, poor substrates for neprilysin, an off-target proteinase, and stable in blood ex vivo. When administered to mice with HT1080 xenografts, conjugates, such as 19, preferentially released Dox in tumor relative to heart tissue and prevented tumor growth with less marrow toxicity than Dox.

Publication types

  • Comparative Study

MeSH terms

  • Animals
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology
  • Cell Line, Tumor
  • Doxorubicin / analogs & derivatives*
  • Doxorubicin / pharmacology
  • Drug Discovery* / methods
  • Humans
  • Matrix Metalloproteinases / chemistry*
  • Matrix Metalloproteinases / pharmacology
  • Mice
  • Prodrugs / chemistry*
  • Prodrugs / pharmacology
  • Xenograft Model Antitumor Assays / methods

Substances

  • Antineoplastic Agents
  • Prodrugs
  • Doxorubicin
  • Matrix Metalloproteinases