Chemistry of the bleomycin-induced alkali-labile DNA lesion

Mariko Aso, Mitsumasa Kondo, Hiroshi Suemune, Sidney M. Hecht

Research output: Contribution to journalArticlepeer-review

39 Scopus citations


Treatment of B-form DNA with the antitumor antibiotic bleomycin in the presence of Fe2+ and O2 affords both DNA strand scission and the formation of alkali-labile lesions, the proportion of which is quite sensitive to the concentration of O2 present. The alkali-labile lesions can undergo fragmentation cleanly in the presence of n-butylamine to afford DNA fragments containing 5'- and 3'-phosphate termini at the site of the alkali-labile lesion. The mechanism of decomposition of the alkali-labile lesion was studied, leading to identification of a putative intermediate that is converted readily to an (oligo)nucleotide 3'-phosphate in the presence of n- BuNH2, as well as the identification of the byproduct of the fragmentation reaction containing the carbon atoms originally present within the alkali- labile lesion.

Original languageEnglish (US)
Pages (from-to)9023-9033
Number of pages11
JournalJournal of the American Chemical Society
Issue number39
StatePublished - Oct 6 1999
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry
  • Biochemistry
  • Colloid and Surface Chemistry


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