Novel nitrogen mustard-armed combi-molecules for the selective targeting of epidermal growth factor receptor overexperessing solid tumors: discovery of an unusual structure-activity relationship

J Med Chem. 2007 May 31;50(11):2605-8. doi: 10.1021/jm070144p. Epub 2007 May 2.

Abstract

To enhance the potency of "combi-molecules", we designed 6a-d and 18 to release an inhibitor of EGFR TK and a bifunctional alkylator. The combi-molecules blocked EGFR TK with potency increasing with the basicity of the mustard moiety. They selectively killed cells transfected with EGFR and were potent against the DU145 prostate cancer cells. Combi-molecule 6a blocked EGFR phosphorylation in an irreversible manner, induced DNA-cross-links, and arrested the cells in mid-S.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents, Alkylating / chemical synthesis*
  • Antineoplastic Agents, Alkylating / chemistry
  • Antineoplastic Agents, Alkylating / pharmacology
  • Cell Cycle / drug effects
  • Cell Line, Tumor
  • Cross-Linking Reagents / chemical synthesis
  • Cross-Linking Reagents / chemistry
  • Cross-Linking Reagents / pharmacology
  • DNA / metabolism
  • DNA Damage
  • Drug Screening Assays, Antitumor
  • ErbB Receptors / antagonists & inhibitors*
  • ErbB Receptors / biosynthesis
  • ErbB Receptors / genetics
  • Humans
  • Male
  • Models, Molecular
  • Nitrogen Mustard Compounds / chemical synthesis*
  • Nitrogen Mustard Compounds / chemistry
  • Nitrogen Mustard Compounds / pharmacology
  • Structure-Activity Relationship
  • Transfection
  • Triazenes / chemical synthesis*
  • Triazenes / chemistry
  • Triazenes / pharmacology

Substances

  • Antineoplastic Agents, Alkylating
  • Cross-Linking Reagents
  • Nitrogen Mustard Compounds
  • Triazenes
  • DNA
  • ErbB Receptors