Enhancement of DNA damage in mammalian cells upon bioreduction of the nitroimidazole-aziridines RSU-1069 and RSU-1131

Biochem Pharmacol. 1988 Oct 15;37(20):3837-42. doi: 10.1016/0006-2952(88)90064-0.

Abstract

The induction of DNA double-(dsb) and single-(ssb) strand breaks by RSU-1069, RSU-1131 and misonidazole in V79 mammalian cells has been investigated using sedimentation in isokinetic sucrose gradients after incubation for various times (1-3 hr) at 310 K under both hypoxic and aerobic conditions. Double strand breaks are produced by RSU-1069 and RSU-1131 predominantly under hypoxic conditions. Comparison of the cellular DNA damage induced by these agents leads to the following facts: (1) the yield of ssb induced by these agents is substantially increased under hypoxia, (2) RSU-1069 and RSU-1131 are much more effective than misonidazole, on a concentration basis, at causing strand breakage both under hypoxic and aerobic conditions; and (3) RSU-1069 is more efficient on a concentration basis than RSU-1131 at inducing both ssb and dsb under both conditions. From these findings and molecular studies it is suggested that these 2-nitroimidazole aziridines act as monofunctional alkylating agents under aerobic conditions, a factor that governs their aerobic cytotoxicity. Under hypoxic conditions, it is suggested that the induction of dsb and crosslinks by these agents (bifunctional character) may play a major role in determining the ability of such agents to act as hypoxia-selective cytotoxins.

MeSH terms

  • Antineoplastic Agents / pharmacology*
  • Cell Survival / drug effects
  • Cells, Cultured
  • Cross-Linking Reagents / pharmacology
  • DNA / drug effects*
  • DNA Damage*
  • Misonidazole / analogs & derivatives*
  • Misonidazole / pharmacology
  • Oxidation-Reduction
  • Oxygen / pharmacology
  • Radiation-Sensitizing Agents / pharmacology*

Substances

  • Antineoplastic Agents
  • Cross-Linking Reagents
  • Radiation-Sensitizing Agents
  • 1-(2-nitro-1-imidazolyl)-3-aziridino-2-propanol
  • RSU 1131
  • Misonidazole
  • DNA
  • Oxygen