title: Reaction between ellagic acid and an ultimate carcinogen.
abstract: The reaction coordinate between a typical ultimate carcinogen benzo[a]pyrene-7,8-diol-9,10-epoxide (BPDE) and ellagic acid, a proven chemopreventive agent active against cancers caused by polycyclic aromatic hydrocarbons (PAHs), was examined by density functional theory (DFT) and semiempirical MO calculations, and activation energy was calculated. The effect of a polar environment was included using Tomasi and the Langevin dipoles methods. The calculated BPDE/ellagic acid reaction free energy of activation is found to be in decent agreement with experimental data [Sayer, J. M. et al. J. Am. Chem. Soc. 1982, 104, 5562-5564]. This work sheds light on the mechanism of action of ellagic acid. Quantum chemical calculations of this kind are valuable for the design of ellagic acid derivatives with even lower activation energy and increased reactivity toward ultimate carcinogens as well as controlled reactivity toward DNA.
authors.affiliation: Laboratoire de Physique Moléculaire, UMR CNRS 6624, Faculté des Sciences et Techniques, La Bouloie, Université de Franche-Comté, 25030 Besançon Cedex, France.
authors.forename: Philippe
authors.initials: P
authors.lastname: Huetz
authors.forename: Nasim
authors.initials: N
authors.lastname: Mavaddat
authors.forename: Janez
authors.initials: J
authors.lastname: Mavri
mesh_terms: D015123:7,8-Dihydro-7,8-dihydroxybenzo(a)pyrene 9,10-oxide / Q000737:chemistry*; D000465:Algorithms; D016588:Anticarcinogenic Agents / Q000737:chemistry*; D002273:Carcinogens / Q000737:chemistry*; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D003198:Computer Simulation; D004610:Ellagic Acid / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D010946:Plants, Medicinal
chemical_list: D016588:Anticarcinogenic Agents; D002273:Carcinogens; D004610:Ellagic Acid; D015123:7,8-Dihydro-7,8-dihydroxybenzo(a)pyrene 9,10-oxide