Effects of pH and salt concentration on the hydrolysis of a benzo[alpha]pyrene 7,8-diol-9,10-epoxide catalyzed by DNA and polyadenylic acid

Chemico-biological Interactions
D P MichaudD M Jerina

Abstract

The time-dependent absorbance change that occurs when benzo[alpha]pyrene 7,8-diol-9,10-epoxide is added to solutions of calf thymus DNA has been shown, by an unequivocal chromatographic method, to correspond to DNA-catalyzed hydrolysis of the diol-epoxide. At 25 degrees C and mu = 0.10, the kinetics of the reaction of the diol-epoxide with polyadenylic acid or DNA are consistent with preequilibrium formation of a non-covalent complex between the diol-epoxide and the polynucleotide or DNA, followed by hydrolysis of the bound epoxide by a process that is first-order in hydronium ions. Cacodylic acid also catalyzes the hydrolysis of the epoxide bound to polyadenylic acid. The rate of the DNA-catalyzed hydrolysis exhibits little or no enantiomeric selectivity for the diol-epoxide. DNA catalyzed hydrolysis of the diol-epoxide is extraordinarily sensitive to the salt concentration in the reaction medium: the rate of hydrolysis of the bound epoxide at pH 7 is retarded by a factor of approximately 45 in the presence of 0.1 M sodium chloride compared to a 1 mM buffer containing no added salt. Thus, studies of the interactions of DNA with carcinogenic diol-epoxides must take into account the ionic environment of DNA within the cell.

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Citations

May 1, 1984·Proceedings of the National Academy of Sciences of the United States of America·T Meehan, D M Bond
Dec 22, 1986·Nucleic Acids Research·A Kootstra
Jun 10, 1997·Proceedings of the National Academy of Sciences of the United States of America·W W Johnson, F P Guengerich
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