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The mechanism of binding of polycyclic aromatic hydrocarbons to nucleic acids: A theoretical investigation
Author(s) -
Umans Robert S.,
Pullman Bernard
Publication year - 1971
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.560050511
Subject(s) - chemistry , nucleic acid , dna , in vivo , polycyclic aromatic hydrocarbon , reactive intermediate , hydrocarbon , computational chemistry , molecule , organic chemistry , biochemistry , catalysis , biology , microbiology and biotechnology
A kinetic model employing calculated atom and bond localization energies to approximate relative activation energies of reaction is used to analyse previously obtained experimental results for in vitro and in vivo chemical binding of polycyclic aromatic hydrocarbons to nucleic acids. It is found that in vitro linkage of hydrocarbons to DNA induced by a microsomal hydroxylating system is compatible with mechanisms involving either attack at the most reactive hydrocarbon center or attack at the most reactive hydrocarbon bond. Independent evidence leads us to favor the former mechanism. Further, the limited experimental data for in vivo linkage of hydrocarbons to DNA is found to be consistent with a model involving attack at the most reactive bond of the molecule: the “ K region”. This model is supported by a close parallelism found between extent of hydrocarbons bound to DNA in vivo and the experimentally determined relative reactivities of their K regions.