title: Chemical reaction of soybean flavonoids with DNA: a computational study using the implicit solvent model.
abstract: Genistein, daidzein, glycitein and quercetin are flavonoids present in soybean and other vegetables in high amounts. These flavonoids can be metabolically converted to more active forms, which may react with guanine in the DNA to form complexes and can lead to DNA depurination. We assumed two ultimate carcinogen forms of each of these flavonoids, diol epoxide form and diketone form. Density functional theory (DFT) and Hartree-Fock (HF) methods were used to study the reaction thermodynamics between active forms of flavonoids and DNA guanine. Solvent reaction field method of Tomasi and co-workers and the Langevin dipoles method of Florian and Warshel were used to calculate the hydration free energies. Activation free energy for each reaction was estimated using the linear free energy relation. Our calculations show that diol epoxide forms of flavonoids are more reactive than the corresponding diketone forms and are hence more likely flavonoid ultimate carcinogens. Genistein, daidzein and glycitein show comparable reactivity while quercetin is less reactive toward DNA.
authors.affiliation: School of Chemical Sciences, University Sains Malaysia, Penang 11800, Malaysia.
authors.forename: Hassan H
authors.initials: HH
authors.lastname: Abdallah
authors.affiliation: National Institute of Chemistry, Hajdrihova 19, SI-1001 Ljubljana, P. O. Box 660, Slovenia.|EN-FIST Centre of Excellence, Dunajska 156, SI-1000 Ljubljana, Slovenia.
authors.forename: Janez
authors.initials: J
authors.lastname: Mavri
authors.affiliation: National Institute of Chemistry, Hajdrihova 19, SI-1001 Ljubljana, P. O. Box 660, Slovenia.
authors.forename: Matej
authors.initials: M
authors.lastname: Repič
authors.affiliation: Department of Chemistry, Faculty of Science, University of Malaya, Kuala Lumpur 50603, Malaysia.
authors.forename: Vannajan Sanghiran
authors.initials: VS
authors.lastname: Lee
authors.affiliation: School of Pharmaceutical Sciences, University Sains Malaysia, Penang 11800, Malaysia.
authors.forename: Habibah A
authors.initials: HA
authors.lastname: Wahab
mesh_terms: D004247:DNA / Q000737:chemistry*; D005419:Flavonoids / Q000737:chemistry*; D006147:Guanine / Q000737:chemistry*; D013025:Glycine max / Q000737:chemistry*
chemical_list: D005419:Flavonoids; D006147:Guanine; D004247:DNA