Chemistry of the bleomycin-induced alkali-labile DNA lesion

Mariko Aso, Mitsumasa Kondo, Hiroshi Suemune, Sidney Hecht

Research output: Contribution to journalArticle

36 Citations (Scopus)

Abstract

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
Volume121
Issue number39
DOIs
StatePublished - Oct 6 1999
Externally publishedYes

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Bleomycin
Alkalies
DNA
Phosphates
Antibiotics
Nucleotides
Byproducts
B-Form DNA
Decomposition
Atoms
Carbon
Anti-Bacterial Agents

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Chemistry of the bleomycin-induced alkali-labile DNA lesion. / Aso, Mariko; Kondo, Mitsumasa; Suemune, Hiroshi; Hecht, Sidney.

In: Journal of the American Chemical Society, Vol. 121, No. 39, 06.10.1999, p. 9023-9033.

Research output: Contribution to journalArticle

Aso, Mariko ; Kondo, Mitsumasa ; Suemune, Hiroshi ; Hecht, Sidney. / Chemistry of the bleomycin-induced alkali-labile DNA lesion. In: Journal of the American Chemical Society. 1999 ; Vol. 121, No. 39. pp. 9023-9033.
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