Chem. J. Chinese Universities ›› 2009, Vol. 30 ›› Issue (8): 1596.

• Articles • Previous Articles     Next Articles

Theoretical Study of the Reaction Mechanism for the Formation of DNA Adducts by α-Hydroxy-nitrosopyrrolidine

LI Lan1*, WANG Hong1, NIU Xiao-Juan2, LI Zong-He3   

  1. 1. Department of Mathematic and Physics, Shanghai Institute of Technolgy, Shanghai 200235, China;
    2. School of Physics & Information Engineering, Jianghan University, Wuhan 430056, China;
    3. Department of Chemistry, Beijing Normal University, Beijing 100875, China
  • Received:2008-04-25 Online:2009-08-10 Published:2009-08-10
  • Contact: LI Lan. E-mail: lilansit@yahoo.com.cn
  • Supported by:

    上海应用技术学院科研启动项目(批准号: YJ2007-36)和上海市教委项目(批准号: YYY-07015)资助.

Abstract:

The reaction mechanism for the formation of ultimate carcinogens diazohydroxide(B), diazonium(C) and oxoniumions(D) by α-hydroxylation-NPYR and the alkylation process of C and guanine were investigated including solvent effects at the B3LYP/6-31G** level. The formation of ultimate carcinogens involves isomerization and protonation. And the process is relatively easy to occur. The alkylation reaction by ultimate carcinogen C and N7 site of guanine is an SN2 process, and forms DNA adduct F and G. Adduct G is isomerized by F. The isomerization energies are relatively high(in the gas phase: 244.77 kJ/mol; in solvent of water: 234.83 kJ/mol), which is consistent with the experiment that adduct F is the primary alkylation product.

Key words: α-Hydroxy-nitrosopyrrolidine; Density functional theory; DNA adduct; Carcinogen

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