Structural Requirements for Mitomycin C DNA Bonding

Information of the specific structure of the activated mitomycin species leading to selective DNA bonding has been secured by determining the bonding sequence selectivities of modified mitomycins in which the identity, spatial orientation, and state of unsaturation of the C-9 and C-9a substituents i...

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Bibliographic Details
Published in:Biochemistry (Easton) 1995-05, Vol.34 (21), p.7120-7126
Main Authors: Li, Ven-Shun, Choi, Daeock, Tang, Moon-shong, Kohn, Harold
Format: Article
Language:English
Subjects:
Base Sequence
Binding Sites
DNA - chemistry
DNA - metabolism
Mitomycin - chemistry
Mitomycin - metabolism
Molecular Sequence Data
Molecular Structure
Oxidation-Reduction
Stereoisomerism
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Summary:Information of the specific structure of the activated mitomycin species leading to selective DNA bonding has been secured by determining the bonding sequence selectivities of modified mitomycins in which the identity, spatial orientation, and state of unsaturation of the C-9 and C-9a substituents in the mitomycin were varied. Both mitomycin-9a-sulfonate (8) and mitomycin D (9) gave DNA bonding profiles comparable to those obtained for mitomycin C (1) under reductive conditions, indicating that neither the stereochemistry of the C-9 and C-9a substituents nor the identity of the leaving group at C-9a influenced the site(s) of DNA bonding. These results indicated that aromatization of the dihydropyrrole ring in mitomycin C precedes DNA binding and mitomycin C-1 bonding.
ISSN:0006-2960
1520-4995
DOI:10.1021/bi00021a025