Homo- and hetero-dimers of inactive organophosphorous group binding at dual sites of AChE

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 21, 2011, Pages 6404-6408

  Zhao, Qianfei ^a   Xie, Ruliang ^a   Zhang, Tao ^a   Fang, Jing ^b   Mei, Xiangdong ^a   Ning, Jun ^a   Tang, Yun ^b  

^a INSTITUTE OF PLANT PROTECTION   (China)

^b EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

AChE; AChE inhibiting potency; Dual site; Homo and hetero dimer; Organophosphorous insecticide

Indexed keywords

ACETYLCHOLINESTERASE; HETERODIMER; HOMODIMER; ORGANOPHOSPHORUS COMPOUND;

ARTICLE; BINDING AFFINITY; CATALYSIS; CHEMICAL INTERACTION; CONCENTRATION (PARAMETERS); DIMERIZATION; DROSOPHILA MELANOGASTER; DRUG BINDING; DRUG STRUCTURE; ENZYME ACTIVE SITE; ENZYME INHIBITION; IC 50; INSECT; INSECTICIDAL ACTIVITY; LIPAPHIS ERYSIMI; MOLECULAR DOCKING; NONHUMAN; TETRANYCHUS CINNBARINUS;

DROSOPHILA MELANOGASTER; LIPAPHIS ERYSIMI; TETRANYCHUS;

EID: 80054781087     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.08.098     Document Type: Article

References (31)

1. Kiessling, L.; Gestwicki, J.; Strong, L. E. Curr. Opin. Chem. Biol. 2000, 4, 696.
2. Wang, J. Q.; Chen, X.; Zhang, W.; Zacharek, S.; Chen, Y.; Wang, P. G. J. Am. Chem. Soc. 1999, 121, 8174.
3. Goldstein, B.; Wofsy, C. J. Math. Biol. 1980, 10, 347.
4. Lee, Y. C.; Lee, R. T. Ace. Chem. Res. 1995, 28, 321.
5. Bertozzi, C. R.; Kiessling, L. L. Science 2001, 291, 2357.
6. Carlier, P. R.; Du, D. M.; Han, Y. F.; Liu, J.; Perola, E.; Williams, I. D.; Pang, Y. P. Angew. Chem., Int. Ed. 2000, 39, 1775.
7. Kryger, G.; Silman, I.; Sussman, J. Structure 1999, 7, 297.
8. Zhao, Q. F.; Yang, G. Q.; Mei, X. D.; Ning, J. J. Pestic. Sci. 2008, 33, 371.
9. Zhao, Q. F.; Yang, G. Q.; Mei, X. D.; Ning, J. Pestic. Biochem. Physiol. 2009, 95, 131.
10. Ma, H. J.; Xie, R. L.; Zhao, Q. F.; Mei, X. D.; Ning, J. J. Agric. Food Chem. 2010, 58, 12817.
11. Casida, J. E.; Quistad, G. B. Chem. Biol. Interact. 2005, 277, 157.
12. Yamamoto, Y.; Ishihara, Y.; Kuntz, I. D. J. Med. Chem. 1994, 37, 3141.
13. Alonso, D.; Dorronsoro, I.; Rubio, L.; Muñoz, P.; García-Palomero, E.; Del Monte, M.; Bidon-Chanal, A.; Orozco, M.; Luque, F. J.; Castro, A.; Medina, M.; Martínez, A. Bioorg. Med. Chem. 2005, 13, 6588.
14. Ellman, G. L.; Courtney, K. D.; Feather-Stone, R. M. Biochem. Pharmacol. 1961, 7, 88.
15. Gorun, V.; Proinov, I.; Itescu, V.; Balaban, G.; Bârzu, O. Modif. Anal. Biochem. 1978, 86, 324.
16. These insects were reared in a room maintained at 25 (±1) × °C 60 (±5)% relative humidity, and 14 h light photoperiod. Stock solutions of test compounds were prepared in acetone at a concentration of 10 g/L and then diluted to the required test concentrations with water (containing 0.1% Triton X-100).
17. Harel, M.; Kryger, G.; Rosenberry, T. L.; Mallender, W. D.; Lewis, T.; Fletcher, R. J.; Guss, J. M.; Silman, I.; Sussman, J. L. Protein Sci. 2000, 9, 1063.
18. Available from: http://www.rcsb.org/pdb/home/home.do.
19. Prime, version 2.1, Schrödinger, LLC, New York, NY, 2009.
20. LigPrep, version 2.3, Schrödinger, LLC, New York, NY, 2009.
21. Schrödinger Suite 2009 InducedFit Docking protocol
22. Glide version 5.5, Schrödinger, LLC, New York, NY, 2009
23. Prime version 2.1, Schrödinger, LLC, New York, NY, 2009.
24. Pang, Y. P.; Quiram, P.; Jelacic, T.; Hong, F.; Brimijoin, S. J. Biol. Chem. 1996, 271, 236.
25. Wang, H.; Carlier, P. R.; Ho, W. L.; Wu, D. C.; Lee, N. T.; Li, C. P.; Pang, Y. P.; Han, Y. F. NeuroReport 1999, 10, 789.
26. Wu, D. C.; Xiao, X. Q.; Ng, A. K.; Chen, P. M.; Chung, W.; Lee, N. T.; Carlier, P. R.; Pang, Y. P.; Yu, A. C.; Han, Y. F. Neurosci. Lett. 2000, 288, 95.
27. Carlier, P. R.; Chow, E. S. H.; Han, Y.; Liu, J.; Yazal, J. E.; Pang, Y. P. J. Med. Chem. 1999, 42, 4225.
28. Hu, M.; Wu, L.; Hsiao, G.; Yen, M. J. Med. Chem. 2002, 45, 2277.
29. Rampa, A.; Bisi, A.; Valenti, P.; Recanatini, M.; Cavalli, A.; Andrisano, V.; Cavrini, V.; Fin, L.; Buriani, A.; Giusti, P. J. Med. Chem. 1998, 41, 3976.
30. Rampa, A.; Piazzi, L.; Belluti, F.; Gobbi, S.; Bisi, A.; Bartolini, M.; Andrisano, V.; Cavrini, V.; Cavalli, A.; Recanatini, M.; Valenti, P. J. Med. Chem. 2001, 44, 3810.
31. Piazzi, L.; Rampa, A.; Bisi, A.; Gobbi, S.; Belluti, F.; Cavalli, A.; Bartolini, M.; Andrisano, V.; Valenti, P.; Recanatini, M. J. Med. Chem. 2003, 46, 2279.