Carbon-7 substituted actinomycin D analogues as improved antitumor agents: synthesis and DNA-binding and biological properties

J Med Chem. 1982 Oct;25(10):1214-9. doi: 10.1021/jm00352a023.

Abstract

7-(2,3-Epoxypropoxy)actinomycin D has been synthesized along with its major companion product, 7-(2,3-dihydroxypropoxy)actinomycin D. They were characterized by UV-visible and CD spectra and by NMR studies. According to UV-visible absorptiometry, circular dichroism, and thermal denaturation studies, they bind to DNA in a manner that is comparable to actinomycin D. The analogues are, like actinomycin D, extremely cytotoxic to human lymphoblastic leukemic cells (CCRF-CEM) in vitro but are significantly less toxic than actinomycin D to normal CDF1 mice is vivo. Unlike actinomycin, these analogues are metabolized in rats, and the metabolites are excreted in rat urine at a rapid rate. Compared to actinomycin D, the antitumor activity of the 7-(2,3-epoxypropoxy)actinomycin analogue against P-388 leukemia in mice is decidedly superior, and the therapeutic index is improved several fold.

Publication types

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

MeSH terms

  • Animals
  • Antibiotics, Antineoplastic / chemical synthesis*
  • Cells, Cultured
  • Chemical Phenomena
  • Chemistry
  • Circular Dichroism
  • DNA / metabolism*
  • Dactinomycin / analogs & derivatives*
  • Dactinomycin / chemical synthesis
  • Dactinomycin / metabolism
  • Dactinomycin / pharmacology
  • Hot Temperature
  • Leukemia, Experimental / drug therapy
  • Magnetic Resonance Spectroscopy
  • Male
  • Mice
  • Nucleic Acid Denaturation

Substances

  • Antibiotics, Antineoplastic
  • Dactinomycin
  • 7-(2,3-epoxypropoxy)actinomycin D
  • DNA