Reaction between ellagic acid and an ultimate carcinogen
Reaction between ellagic acid and an ultimate carcinogen
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DOI：
10.1021/ci050163c
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发表时间：
2005-11-01
影响因子：
5.6
通讯作者：
Mavri, J
中科院分区：
文献类型：
--
作者：
Huetz, P;Mavaddat, N;Mavri, J
采用密度泛函理论（DFT）和半经验分子轨道（MO）方法，研究了典型的终极致癌物苯并[a]芘-7，8-二醇-9，10-环氧化合物（BPDE）与化学预防剂鞣花酸之间的反应配位，并计算了反应活化能.使用Tomasi和Langevin偶极子方法包括极性环境的影响。发现计算的BPDE/鞣花酸反应活化自由能与实验数据相当一致（Sayer，J.M.等J. Ant. 1982，104，55625564]。这项工作揭示了鞣花酸的作用机制。这种量子化学计算对于设计具有更低活化能和对最终致癌物的增加的反应性以及对DNA的受控反应性的鞣花酸衍生物是有价值的。
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. Ant. Chem. Soc. 1982,.104, 55625564]. 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.