APPLICATION OF QUANTUM-CHEMICAL METHODS TO ESTIMATE THE CARCINOGENIC PROPERTIES OF BENZOPYRENE METABOLITES
DOI:
https://doi.org/10.32782/naturaljournal.10.2024.4Keywords:
quantum-chemical calculations, metabolites, carcinogenic activity, molecular orbital populationAbstract
Benzo[a]pyrene is a common environmental pollutant and a powerful carcinogen that can accumulate in various organs and tissues, causing DNA damage through the adducts’ formation, which contributes to the development of neoplasms of various localization. This compound carcinogenic activity is well studied and proven to be related to the nature and electronic configuration of biologically activated metabolites. Since not all metabolites of benzo[a]pyrene show carcinogenic effects, in this study an attempt to theoretically investigate their spectral properties and to use the obtained data in establishing a correlation with the observed carcinogenic effect was made. In order to study the spectroscopic properties of benzo[a]pyrene metabolites which, depending on the transformation pathways, can form products with different carcinogenic activity, the energies of the lower electronically excited states of metabolite molecules were calculated using the semi-empirical PM3 method (Hyper Chem 7.5). To determine the features of the electron density distribution during the molecules’ excitation, we used the values of the occupancy of the highest occupied molecular orbital and the lowest unoccupied molecular orbital, which participate in one-electron transitions. The calculation results of the position of the benzo[a]pyrene absorption spectra satisfactorily correlate with the experimental data presented in the literature, which is a confirmation of the obtained data reliability regarding the spectral characteristics of its metabolites. The performed calculations made it possible to determine the position of the long-wavelength absorption bands of some metabolites, for which experimental data have not been currently determined. It has been established that the longwave bands in the absorption spectra of carcinogenic metabolites of benzo[a]pyrene in the number: BP → BP 7,8-epoxide → BP 7,8-dihydrodiol → BP 7,8-dihydrodiol-9,10-epoxide are equally intense and sequentially shifted to the short-wavelength region relative to the benzo[a]pyrene absorption spectra.
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