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Chemical Reaction of Soybean Flavonoids with DNA: A Computational Study Using the Implicit Solvent Model
School of Chemical Sciences, University Sains Malaysia, Penang 11800, Malaysia
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
Department of Chemistry, Faculty of Science, University of Malaya, Kuala Lumpur 50603, Malaysia
School of Pharmaceutical Sciences, University Sains Malaysia, Penang 11800, Malaysia
* Authors to whom correspondence should be addressed.
Received: 17 October 2011; in revised form: 31 December 2011 / Accepted: 4 January 2012 / Published: 25 January 2012
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.
Keywords: flavonoids; DNA; chemical reaction; carcinogenesis; DFT calculation
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Abdallah, H.H.; Mavri, J.; Repič, M.; Lee, V.S.; Wahab, H.A. Chemical Reaction of Soybean Flavonoids with DNA: A Computational Study Using the Implicit Solvent Model. Int. J. Mol. Sci. 2012, 13, 1269-1283.
Abdallah HH, Mavri J, Repič M, Lee VS, Wahab HA. Chemical Reaction of Soybean Flavonoids with DNA: A Computational Study Using the Implicit Solvent Model. International Journal of Molecular Sciences. 2012; 13(2):1269-1283.
Abdallah, Hassan H.; Mavri, Janez; Repič, Matej; Lee, Vannajan Sanghiran; Wahab, Habibah A. 2012. "Chemical Reaction of Soybean Flavonoids with DNA: A Computational Study Using the Implicit Solvent Model." Int. J. Mol. Sci. 13, no. 2: 1269-1283.