Probing platinum-adenine-n3 adduct formation with DNA minor-groove binding agents

Chem Res Toxicol. 2010 Jul 19;23(7):1148-50. doi: 10.1021/tx100170p.

Abstract

Me-lex(py/py), an adenine-N3-selective alkylating agent, and the reversible minor-groove binder netropsin were used to probe the formation of unusual minor-groove adducts by the cytotoxic hybrid agent PT-ACRAMTU ([PtCl(en)(ACRAMTU)](NO(3))(2); en = ethane-1,2-diamine, ACRAMTU = 1-[2-(acridin-9-ylamino)ethyl]-1,3-dimethylthiourea). PT-ACRAMTU was found by chemical footprinting to inhibit specific Me-lex-mediated DNA cleavage at several adenine sites but not at nonspecific guanine, which is consistent with the platination of adenine-N3. In a cell proliferation assay, a significant decrease in cytotoxicity was observed for PT-ACRAMTU, when cancer cells were pretreated with netropsin, suggesting that minor-groove adducts in cellular DNA contribute to the biological activity of the hybrid agent.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Adenine / chemistry*
  • Alkylating Agents / chemistry
  • Alkylating Agents / toxicity*
  • DNA Adducts / chemistry*
  • DNA Cleavage / drug effects
  • Netropsin / pharmacology
  • Organoplatinum Compounds / chemistry*
  • Organoplatinum Compounds / toxicity

Substances

  • Alkylating Agents
  • DNA Adducts
  • Organoplatinum Compounds
  • Netropsin
  • Adenine