Conformations of complexes between mitomycin and decanucleotides. 2. Application of the model to mitomycin C derivatives. Extension to covalent binding with adenine
- 1 July 1986
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 29 (7) , 1256-1263
- https://doi.org/10.1021/jm00157a024
Abstract
Molecular mechanics simulation of the interactions of important mitomycin C analogues monocovalently bound to DNA models are presented. These analogues included substituents such as p-hydroxyphenyl, 2-mercaptoethyl, and dimethylamidinium on N7 of mitomycin C and the DNA models consisted of d(GCGCGCGCGC)2 and d(GCGCATGCGC)2. The excellent fits and strong binding affinities of these highly potent analogues support the usefulness of the model. The binding of a mitomycin-related N-phenylpyrrole with a carbamoyloxy substituent to O6 of guanine was studied. Finally, a reactive mitomycin intermediate proposed by Moore was shown to interact with DNA in a way consistent with the formation of a covalent adduct.This publication has 2 references indexed in Scilit:
- Full structure of a mitomycin C dinucleoside phosphate adduct. Use of differential FT-IR spectroscopy in microscale structural studiesJournal of the American Chemical Society, 1983
- Mitomycins and Porfiromycin: Chemical Mechanism of Activation and Cross-linking of DNAScience, 1964