Synthesis and antitumor evaluation of a highly potent cytotoxic DNA cross-linking polyamine analogue, 1,12-diaziridinyl-4,9-diazadodecane

J Med Chem. 1996 Jan 5;39(1):339-41. doi: 10.1021/jm9500885.

Abstract

A diaziridinylspermine analogue, 1,12-diaziridinyl-4,9-diazadodecane (NSC-667005), was synthesized as a bisalkylating agent with a polyamine backbone. DNA cross-linking was detected in the reaction of linearized pBR322 DNA with 1,12-diaziridinyl-4,9-diazadodecane at concentrations comparable with that required for cross-linking by two nitrogen mustard drugs, mechlorethamine and melphalan. A significant increase in life span of female CD2F1 mice bearing L1210 murine leukemia was observed after intravenous administration of 1,12-diaziridinyl-4,9-diazadodecane in doses of less than 2.7 mg/kg, given on days 1, 5, and 9 of treatment.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Antineoplastic Agents / administration & dosage
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Aziridines / administration & dosage
  • Aziridines / chemical synthesis*
  • Aziridines / chemistry
  • Aziridines / pharmacology*
  • Cross-Linking Reagents / chemical synthesis*
  • Cross-Linking Reagents / pharmacology
  • Cross-Linking Reagents / toxicity
  • DNA / drug effects*
  • Electrophoresis, Agar Gel
  • Female
  • Leukemia L1210 / drug therapy
  • Mechlorethamine / pharmacology
  • Melphalan / pharmacology
  • Mice
  • Mice, Inbred Strains
  • Spermine / administration & dosage
  • Spermine / analogs & derivatives*
  • Spermine / chemical synthesis
  • Spermine / chemistry
  • Spermine / pharmacology
  • Thiotepa / pharmacology

Substances

  • 1,12-diaziridinyl-4,9-diazadodecane
  • Antineoplastic Agents
  • Aziridines
  • Cross-Linking Reagents
  • Spermine
  • Mechlorethamine
  • aziridine
  • DNA
  • Thiotepa
  • Melphalan