Citation: HOU Ruo-Bing, TANG Zong-Xiang, FAN You-Jun, YI Xiang-Hui, WANG Bei-Bei, SUN Yan-Li. Radicals Created fromthe Reactions of 2’-Deoxyadenosine-5’-monophosphate with Hydroxyl Radical[J]. Acta Physico-Chimica Sinica, ;2013, 29(09): 1937-1944. doi: 10.3866/PKU.WHXB201307023 shu

Radicals Created fromthe Reactions of 2’-Deoxyadenosine-5’-monophosphate with Hydroxyl Radical

1.
1 College of Chemistry and Chemical Engineering, Guangxi Normal University, Guilin 541004, Guangxi Province, P. R. China;
2 College of Basic Medicine, Nanjing University of Chinese Medicine, Nanjing 210046, P. R. China;
3 Guilin Normal College, Guilin 541002, Guangxi Province, P. R. China

Received Date: 8 May 2013
Available Online: 2 July 2013
Fund Project: 国家自然科学基金(31271181, 21263002) (31271181, 21263002)江苏省自然科学基金(BK2011811) (BK2011811)广西自然科学基金(2013GXNSFAA019024)资助项目 (2013GXNSFAA019024)

The radicals generated fromreactions of 2'-deoxyadenosine-5'-monophosphate (dAMP) with an HO· radical were studied by the reliable B3LYP/DZP++ method. The results show that the initial primary products are the radicals of HO· addition at the C8 and C4 sites of dAMP and those of dehydrogenation from the NH₂ moiety of dAMP. Moreover, the initial radicals of the C4 site adducts of HO· tend thermodynamically to take place dehydration reactions that yields strong oxidizing, H-abstraction radicals fromthe NH₂ group of dAMP. The electrostatic repeller interaction between the dAMP molecule and HO· results in HO· addition radicals of the C2 atomof dAMP to be a by-product, even if they are relative stable species. These theoretical results agree well with available experimental observations and give proper explanations for some experimental results.
- 2’-Deoxyadenosine-5’-monophosphate,
- Hydroxyl radical,
- Addition reaction,
- Hydrogen abstraction reaction
1. [1]
  
  (1) Po zelski, W. K.; Tullius, T. D. Chem. Rev. 1998, 98, 1089 andreferences therein. doi: 10.1021/cr960437i
2. [2]
  (2) Follmann, H. Chem. Soc. Rev. 2004, 33, 225. doi: 10.1039/a907361b
3. [3]
  (3) Ito, T.; Kuno, S.; Uchida, T.; Fujita, S.; Nishimoto, S. J. Phys. Chem. B 2009, 113, 389. doi: 10.1021/jp801976t
4. [4]
  (4) Kumimova, M. K.; Cowan, A. J.; Matousek, P.; Parker, A. W.;Sun, X. Z.; Towrie, M.; George, M. W. Proc. Natl. Acad. Sci. U. S. A. 2006, 103, 2150. doi: 10.1073/pnas.0506860103
5. [5]
  (5) Vieira, A. J. S. C.; Steenken, S. J. Am. Chem. Soc. 1990, 112,6986. doi: 10.1021/ja00175a036
6. [6]
  (6) Liu, J.; Petzold, C. J.; Ramirez-Arizmendi, L. E.; Perez, J.;Kenttäemaa, H. J. Am. Chem. Soc. 2005, 127, 12758. doi: 10.1021/ja052766a
7. [7]
  (7) Adhikary, A.; Becker, D.; Collins, S.; Koppen, J.; Sevilla, M. D.Nucleic Acids Res. 2006, 34, 1501. doi: 10.1093/nar/gkl026
8. [8]
  (8) Lahoud, G. A.; Hitt, A. L.; Bryant-Friedrich, A. C. Chem. Res. Toxicol. 2006, 19, 1630. doi: 10.1021/tx060174f
9. [9]
  (9) von Sonntag, C. Free-Radical-Induced DNA Damage and Its Repair; Springer-Verlag: Berlin Heidelberg, 2006; pp 9-35.
10. [10]
  (10) Schyman, P.; Eriksson, L. A.; Laaksonen, A. J. Phys. Chem. B2009, 113, 6574. doi: 10.1021/jp9007569
11. [11]
  (11) Lind, M. C.; Richardson, N. A.;Wheeler, S. E.; Schaefer, H. F.J. Phys. Chem. B 2007, 111, 5525. doi: 10.1021/jp0714926
12. [12]
  (12) Reynisson, J.; Steenken, S. Phys. Chem. Chem. Phys. 2002, 4,5346. doi: 10.1039/b204842f
13. [13]
  (13) Li, M. J.; Liu, L.; Wei, K.; Fu, Y.; Guo, Q. X. J. Phys. Chem. B2006, 110, 13582. doi: 10.1021/jp060331j
14. [14]
  (14) Karol, M.; Roman, O. J. Am. Chem. Soc. 1994, 116, 232. doi: 10.1021/ja00080a027
15. [15]
  (15) Karwowski, B. T. Cent. Eur. J. Chem. 2008, 6, 450. doi: 10.2478/s11532-008-0038-z
16. [16]
  (16) Galano, A.; Alvarez-Ldaboy, J. R. Org. Lett. 2009, 11, 5114. doi: 10.1021/ol901862h
17. [17]
  (17) Shukla, P. K.; Kumar, N.; Mishra, P. C. Int. J. Quantum Chem.2009, 111, 2160.
18. [18]
  (18) Chen, Q.; Gu, J.; Compaan, K. R.; Schaefer, H. F. Chem. Eur. J.2010, 16, 11848. doi: 10.1002/chem.201001236
19. [19]
  (19) Evangelista, F. A.; Schaefer, H. F. J. Phys. Chem. A 2004, 108,10258. doi: 10.1021/jp040361r
20. [20]
  (20) Saenger, W. Principles of Nucleic Acid Structure; Sringer-Verlag: NewYork, 1984; pp 253-281.
21. [21]
  (21) Rienstra-Kiracofe, J. C.; Tschumper, G. S.; Schaefer, H. F.;Nandi, S.; Ellison, G. B. Chem. Rev. 2002, 102, 231. doi: 10.1021/cr990044u
22. [22]
  (22) Reed, A. E.; Weinhold, F. J. Chem. Phys. 1983, 78, 4066. doi: 10.1063/1.445134
23. [23]
  (23) Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys.1985, 83, 735. doi: 10.1063/1.449486
24. [24]
  (24) Cossi, M.; Barone, V.; Cammi, R.; Tomasi, J. Chem. Phys. Lett.1996, 255, 327. doi: 10.1016/0009-2614(96)00349-1
25. [25]
  (25) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; et al. Gaussian 03,Revision B.03; Gaussian Inc.: Pittsburgh, PA, 2003.
26. [26]
  (26) Boussicault, F.; Kaloudis, P.; Caminal, C.; Mulazzani, Q. G.;Chatgilialoglu, C. J. Am. Chem. Soc. 2008, 130, 8377. doi: 10.1021/ja800763j
27. [27]
  (27) von Sonntag, C. Free-Radical-Induced DNADamage asApproached by Quantum-Mechanical and Monte CarloCalculations: An Overview fromthe Standpoint of anExperimentalist. In Advances in Quantum Chemistry; Brändas,E.; Sabin, J. R. Eds.; Elsevier Inc.: NewYork, 2007; Vol. 52, pp5-17.
28. [28]
  (28) Náray-Szabó, G.; Ferenczy, G. G. Chem. Rev. 1995, 95,829. doi: 10.1021/cr00036a002
29. [29]
  (29) Lu, T.; Chen, F. J. Comput. Chem. 2012, 33, 580. doi: 10.1002/jcc.v33.5
30. [30]
  (30) Lu, T. Multiwfn, Version 2.4; Beijing, 2012.
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