Int. J. Mol. Sci. 2012, 13(2), 1269-1283; doi:10.3390/ijms13021269
Article

Chemical Reaction of Soybean Flavonoids with DNA: A Computational Study Using the Implicit Solvent Model

Received: 17 October 2011; in revised form: 31 December 2011 / Accepted: 4 January 2012 / Published: 25 January 2012
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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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MDPI and ACS Style

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.

AMA Style

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.

Chicago/Turabian Style

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.

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