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Vol. 56, Issue 3, 633-643, September 1999
Department of Medicine and Cancer Center (E.D.S., S.B.H.), and
Department of Pharmacology (J.M.B.), University of California, San
Diego, La Jolla, California
Intrastrand DNA adducts formed by cisplatin and oxaliplatin were
modeled with molecular mechanics minimization and restrained molecular dynamics simulations in a comparative study. A reasonable set
of force field parameters for the Pt atom were refined by using the
available cisplatinated DNA crystal structure as a guide. This crystal
structure was also used as the starting structure for the simulations.
Analysis of the resulting structures indicated that the covalent
effects of oxaliplatin coordination on DNA structure were very similar
to those of cisplatin. The most prominent difference between the two
structures resulted from the presence of the 1,2-diaminocyclohexane ring in the oxaliplatin adduct. The modeling indicated that this ring
protrudes directly outward into, and fills much of, the narrowed major
groove of the bound DNA, forming a markedly altered and less polar
major groove in the area of the adduct. The differences in the
structure of the adducts produced by cisplatin and oxaliplatin are
consistent with the observation that they are differentially recognized
by the DNA mismatch repair system.
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