Bleomycin-Mediated Degradation of Aristeromycin-Containing DNA. Novel Dehydrogenation Activity of IronII-Bleomycin

Hiroshi Sugiyama, Takashi Sera, Yukihiro Dannoue, Ryuji Marumoto, Isao Saito

Research output: Contribution to journalArticle

30 Citations (Scopus)

Abstract

The antitumor antibiotic bleomycin (BLM) induces C-H bond scission at the C4′ of deoxyribose moiety of DNA in the presence of Fe(II) and O2. To investigate the primary oxidation step, 2′-deoxyaristeromycin (Ar) possessing a cyclopentane ring instead of a ribofuranose ring was incorporated into the BLM-cleaving site of synthetic oligonucleotide d(GGArAGG). It was found that an unprecedented dehydrogenation occurs effectively at the C4′ and C6′ positions of the Ar moiety to give 2′-deoxyneplanocin A containing oligonucleotide together with a minor but stereospecific C4′ hydroxylation in the FeII-BLM-mediated degradation of duplex d(GGArAGG)-d(CCTTCC). An intermediate C4′ carbocation derived from one-electron oxidation of initially formed C4′ radical has been proposed for the dehydrogenation reaction.

Original languageEnglish
Pages (from-to)2290-2295
Number of pages6
JournalJournal of the American Chemical Society
Volume113
Issue number6
Publication statusPublished - Mar 13 1991
Externally publishedYes

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Oligonucleotides
Bleomycin
Dehydrogenation
DNA
Thermodynamic properties
Deoxyribose
Cyclopentanes
Degradation
Oxidation
Hydroxylation
Antibiotics
Electrons
Anti-Bacterial Agents
aristeromycin
indium-bleomycin
2'-deoxyaristeromycin

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Bleomycin-Mediated Degradation of Aristeromycin-Containing DNA. Novel Dehydrogenation Activity of IronII-Bleomycin. / Sugiyama, Hiroshi; Sera, Takashi; Dannoue, Yukihiro; Marumoto, Ryuji; Saito, Isao.

In: Journal of the American Chemical Society, Vol. 113, No. 6, 13.03.1991, p. 2290-2295.

Research output: Contribution to journalArticle

Sugiyama, Hiroshi ; Sera, Takashi ; Dannoue, Yukihiro ; Marumoto, Ryuji ; Saito, Isao. / Bleomycin-Mediated Degradation of Aristeromycin-Containing DNA. Novel Dehydrogenation Activity of IronII-Bleomycin. In: Journal of the American Chemical Society. 1991 ; Vol. 113, No. 6. pp. 2290-2295.
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