Stereoelectronic factors influencing the biological activity and DNA interaction of synthetic antitumor agents modeled on CC-1065

J Med Chem. 1988 Mar;31(3):590-603. doi: 10.1021/jm00398a017.

Abstract

The synthesis, physicochemical properties, and biological activities of a series of novel spiro cyclopropyl compounds, modeled on the potent antitumor antibiotic CC-1065 (1), are described. Many of these synthetic analogues are significantly more effective than 1 against murine tumors. In particular, compound 27 exhibits high activity and potency. Structure-activity analysis supports a molecular mechanism for biological action involving hydrophobic interaction of the drug with DNA and acid-catalyzed alkylation of DNA.

MeSH terms

  • Animals
  • Antibiotics, Antineoplastic / chemical synthesis
  • Antibiotics, Antineoplastic / metabolism*
  • Chemical Phenomena
  • Chemistry, Physical
  • Circular Dichroism
  • DNA / metabolism*
  • Duocarmycins
  • Female
  • Indoles*
  • Leucomycins / chemical synthesis
  • Leucomycins / metabolism*
  • Leucomycins / pharmacology
  • Leukemia L1210 / drug therapy
  • Leukemia P388 / drug therapy
  • Mice
  • Mice, Inbred DBA
  • Solubility

Substances

  • Antibiotics, Antineoplastic
  • Duocarmycins
  • Indoles
  • Leucomycins
  • CC 1065
  • DNA