Theoretical study on the aging and reactivation mechanism of tabun-inhibited acetylcholinesterase by using the quantum mechanical / molecular mechanical method

Canadian Journal of Chemistry

Volumn 90, Issue 4, 2012, Pages 376-383

  Li, Yanwei ^a   Du, Likai ^a   Hu, Yueming ^a   Sun, Xiaomin ^a   Hu, Jingtian ^a  

^a SHANDONG UNIVERSITY   (China)

Author keywords

Aging mechanism; QM MM method; Reactivation mechanism; Tabun

Indexed keywords

ACETYLCHOLINESTERASE; AGING MECHANISM; AGING REACTION; B3LYP/6-31G; BOND SCISSIONS; DEPHOSPHORYLATIONS; ETHOXY GROUP; GEOMETRY OPTIMIZATION; IRREVERSIBLE INHIBITIONS; MOLECULAR MECHANICAL METHOD; MOLECULAR MECHANICALS; NUCLEOPHILIC ATTACK; ORGANOPHOSPHOROUS COMPOUNDS; QM/MM METHOD; QUANTUM MECHANICAL; REACTIVATION PROCESS; SINGLE-POINT ENERGY; STATIONARY POINTS; TABUN; THEORETICAL STUDY; WARFARE AGENTS; X-MEANS;

ENERGY BARRIERS; QUANTUM THEORY;

MECHANISMS;

EID: 84861406339     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v2012-007     Document Type: Article

References (31)

1. Alex R. Prasad J. Kuruvilla A. Jacob K. S. Br. J. Psychiatry 2007, 190 (3), 274. 10.1192/bjp.190.3.274a (Pubitemid 46384025)
2. da Silva Gonçalves A. França T. C. C. Wilter A. Figueroa-Villar J. D. J. Braz. Chem. Soc. 2006, 17 (5), 968. 10.1590/S0103-50532006000500022
3. Szinicz L. Toxicology 2005, 214 (3), 167. 10.1016/j.tox.2005.06.011 (Pubitemid 41406257)
4. Delfino R. T. Ribeiro T. S. Figueroa-Villar J. D. J. Braz. Chem. Soc. 2009, 20 (3), 407. 10.1590/S0103-50532009000300003
5. Marrs, T. C. Clinical and Experimental Toxicology of Organophosphates and Carbamates; Butterworth & Heinemann: Oxford, 1992; pp 555-577.
6. Barak D. Ordentlich A. Kaplan D. Barak R. Mizrahi D. Kronman C. Segall Y. Velan B. Shafferman A. Biochemistry 2000, 39 (5), 1156. 10.1021/bi992009n (Pubitemid 30075346)
7. Carletti E. Li H. Li B. Ekstrom F. Nicolet Y. Loiodice M. Gillon E. Froment M. T. Lockridge O. Schopfer L. M. Masson P. Nachon F. J. Am. Chem. Soc. 2008, 130 (47), 16011. 10.1021/ja804941z
8. Worek F. Aurbek N. Koller M. Becker C. Eyer P. Thiermann H. Biochem. Pharmacol. 2007, 73 (11), 1807. 10.1016/j.bcp.2007.02.008 (Pubitemid 46601412)
9. Nachon F. Carletti E. Worek F. Masson P. Chem. Biol. Interact. 2010, 187 (1-3), 44. 10.1016/j.cbi.2010.03.053
10. Sherwood P. de Vries A. H. Guest M. F. Schreckenbach G. Catlow C. R. A. French S. A. Sokol A. A. Bromley S. T. Thiel W. Turner A. J. Billeter S. Terstegen F. Thiel S. Kendrick J. Rogers S. C. Casci J. Watson M. King F. Karlsen E. Sjøvoll M. Fahmi A. Schäfer A. Lennartz C. J. Mol. Struct. (THEOCHEM) 2003, 632 (1-3), 1. 10.1016/s0166-1280(03)00285-9
11. Ahlrichs R. Bär M. Hser M. Horn H. Kölmel C. Chem. Phys. Lett. 1989, 162 (3), 165. 10.1016/0009-2614(89)85118-8
12. Smith W. Forester T. R. J. Mol. Graph. Model. 1996, 14 (3), 136.
13. Yu W. Hu J. Xu F. Sun X. Gao R. Zhang Q. Wang W. Environ. Sci. Technol. 2011, 45 (5), 1917. 10.1021/es103536t
14. Xu F. Yu W. Zhou Q. Gao R. Sun X. Zhang Q. Wang W. Environ. Sci. Technol. 2011, 45 (2), 643. 10.1021/es102660j
15. Xu F. Wang H. Zhang Q. Zhang R. Qu X. Wang W. Environ. Sci. Technol. 2010, 44 (4), 1399. 10.1021/es9031776
16. MacKerell A. Bashford D. Bellott Dunbrack R. L. Evanseck J. D. Field M. J. Fischer S. Gao J. Guo H. Ha S. Joseph-McCarthy D. Kuchnir L. Kuczera K. Lau F. T. K. Mattos C. Michnick S. Ngo T. Nguyen D. T. Prodhom B. Reiher W. E. Roux B. Schlenkrich M. Smith J. C. Stote R. Straub J. Watanabe M. Wiórkiewicz-Kuczera J. Yin D. Karplus M. J. Phys. Chem. B 1998, 102 (18), 3586. 10.1021/jp973084f
17. Sherwood, P. In Modern Methods and Algorithms of Quantum Chemistry; Grotendorst, J., Ed.; NIC-Directors: Princeton, 2000; Vol. 3, pp 285.
18. Bakowies D. Thiel W. J. Phys. Chem. 1996, 100 (25), 10580. 10.1021/jp9536514
19. de Vries A. H. Sherwood P. Collins S. J. Rigby A. M. Rigutto M. Kramer G. J. J. Phys. Chem. B 1999, 103 (29), 6133. 10.1021/jp9913012
20. da Silva Gonçalves A. França T. C. C. Figueroa-Villar J. D. Pascutti P. G. J. Braz. Chem. Soc. 2011, 22 (1), 155. 10.1590/S0103- 50532011000100021
21. Billeter S. R. Turner A. J. Thiel W. Phys. Chem. Chem. Phys. 2000, 2 (10), 2177. 10.1039/a909486e
22. Humphrey W. Dalke A. Schulten K. J. Mol. Graph. Model. 1996, 14 (1), 33.
23. Martí-Renom M. A. Stuart A. C. Fiser A. Sánchez R. Melo F. Sali A. Annu. Rev. Biophys. Biomol. Struct. 2000, 29 (1), 291. 10.1146/annurev.biophys.29.1.291 (Pubitemid 30599596)
24. Brooks B. R. Bruccoleri R. E. Olafson B. D. States D. J. Swaminathan S. Karplus M. J. Comput. Chem. 1983, 4 (2), 187. 10.1002/jcc.540040211
25. Ekström F. J. Astot C. Pang Y. Clin. Pharmacol. Ther. 2007, 82 (3), 282. 10.1038/sj.clpt.6100151 (Pubitemid 47258467)
26. Jorgensen W. L. Chandrasekhar J. Madura J. D. Impey R. W. Klein M. L. J. Chem. Phys. 1983, 79 (2), 926. 10.1063/1.445869
27. Vanommeslaeghe K. Hatcher E. Acharya C. Kundu S. Zhong S. Shim J. Darian E. Guvench O. P. Vorobyov I. Mackerell A. D. J. Comput. Chem. 2010, 31 (4), 671.
28. Kwasnieski O. Verdier L. Malacria M. Derat E. J. Phys. Chem. B 2009, 113 (29), 10001. 10.1021/jp903843s
29. Tian B. Strid A. Eriksson L. A. J. Phys. Chem. B 2011, 115 (8), 1918. 10.1021/jp111525p
30. Wang J. Gu J. Leszczynski J. J. Phys. Chem. B 2008, 112 (11), 3485. 10.1021/jp076974w
31. da Silva Gonçalves A. França T. C. C. Figueroa-Villar J. D. Pascutti P. G. J. Braz. Chem. Soc. 2010, 21 (1), 179. 10.1590/S0103- 50532010000100025