Preclinical evaluation of the pharmacodynamic properties of 2,5-diaziridinyl-3-hydroxymethyl-6-methyl-1,4-benzoquinone

Clin Cancer Res. 2005 Apr 1;11(7):2695-701. doi: 10.1158/1078-0432.CCR-04-1751.

Abstract

Purpose: The purpose of our study was to investigate the cellular accumulation, DNA cross-linking ability, and cellular toxicity of RH1 (2,5-diaziridinyl-3-[hydroxymethyl[-6-methyl-1,4-benzoquinone), a novel DNA alkylating agent currently in clinical trials. In addition, the in vivo efficacy of RH1 formulated in different vehicles was also compared.

Experimental design: RH1 is activated by the two-electron reducing enzyme NQO1 [NADPH:quinone oxidoreductase] forming a potent cytotoxic agent that cross-links DNA. We have used whole blood, cell lines, and primary explanted tumor cultures to measure both the cellular accumulation, DNA cross-linking, and cytotoxicity of RH1. Furthermore, the pharmacokinetic and pharmacodynamic characteristics of RH1 formulated in different vehicles were measured in vivo using the validated comet-X assay in mice bearing human tumor xenografts.

Results: Accumulation of RH1 was shown to be both time and concentration dependent, reaching a maximum after 2 hours and correlated well with DNA cross-linking measurements. DNA cross-linking in vitro could be detected at low (1-10 nmol/L) concentrations after as little as 2 hours exposure. In primary tumor cultures, RH1 induces much higher levels of DNA cross-links at lower doses than either mitomycin C or cisplatin. In vivo efficacy testing using polyvinyl pyrrolidone, saline, or cyclodextrin as vehicles showed DNA cross-links readily detectable in all tissues examined and was enhanced when given in cyclodextrin compared with polyvinyl pyrrolidone or saline.

Conclusions: RH1 represents a potent bioreductive anticancer drug, which may prove effective in the treatment of cancers, particularly those that overexpress NQO1. DNA cross-linking can be reliably measured in tissue using the validated comet-X assay.

Publication types

  • Comparative Study

MeSH terms

  • Animals
  • Aziridines / blood
  • Aziridines / pharmacokinetics
  • Aziridines / pharmacology*
  • Benzoquinones / blood
  • Benzoquinones / pharmacokinetics
  • Benzoquinones / pharmacology*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Comet Assay / methods
  • Cross-Linking Reagents / pharmacology
  • DNA / chemistry
  • DNA / genetics
  • Dose-Response Relationship, Drug
  • Drug Evaluation, Preclinical
  • Female
  • Humans
  • Mice
  • Mice, Nude
  • Treatment Outcome
  • Tritium
  • Xenograft Model Antitumor Assays / methods*

Substances

  • 2,5-diaziridinyl-3-(hydroxymethyl)-6-methyl-1,4-benzoquinone
  • Aziridines
  • Benzoquinones
  • Cross-Linking Reagents
  • Tritium
  • DNA