Use of classical and 3-D QSAR to examine the hydration state of juvenile hormone esterase inhibitors

Bioorganic and Medicinal Chemistry

Volumn 11, Issue 23, 2003, Pages 5101-5116

  Wheelock, Craig E ^a,b   Nakagawa, Yoshiaki ^a   Akamatsu, Miki ^a   Hammock, Bruce D ^b  

^a KYOTO UNIVERSITY   (Japan)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE DERIVATIVE; ALKENE DERIVATIVE; ALKYNE DERIVATIVE; BENZENE DERIVATIVE; CARBOXYLESTERASE; ESTERASE INHIBITOR; FUNCTIONAL GROUP; JUVENILE HORMONE ESTERASE; JUVENILE HORMONE ESTERASE INHIBITOR; SULFIDE; SULFONE DERIVATIVE; TRIFLUOROMETHYLKETONE DERIVATIVE; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; BINDING AFFINITY; COMPARATIVE MOLECULAR FIELD ANALYSIS; COMPARATIVE STUDY; CORRELATION ANALYSIS; CORRELATION COEFFICIENT; DRUG ACTIVITY; DRUG HYDROLYSIS; DRUG MECHANISM; DRUG SYNTHESIS; DRUG TARGETING; HYDROPHOBICITY; MATHEMATICAL ANALYSIS; MOLECULAR MODEL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; STATISTICAL SIGNIFICANCE; VALIDATION PROCESS;

INSECTA; MAMMALIA;

EID: 0242298234     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2003.08.023     Document Type: Article

References (45)

1. Ollis D.L., Cheah E., Cygler M., Dijkstra B., Frolow F., Franken S.M., Harel M., Remington S.J., Silman I., Schrag J., Sussman J.L., Verschueren K.H.G., Goldman A. Protein Eng. 5:1992;197.
2. Satoh T., Hosokawa M. Annu. Rev. Pharmacol. Toxicol. 38:1998;257.
3. Bodor N., Buchwald P. Med. Res. Rev. 20:2000;58.
4. Casida J.E., Gammon D.W., Glickman A.H., Lawrence L.J. Annu. Rev. Pharmacol. Toxicol. 23:1983;413.
5. Wallace T.J., Ghosh S., Grogan W.M. Am. J. Respir. Cell Mol. Biol. 20:1999;1201.
6. Gupta R.C., Dettbarn W.D. Chem.-Biol. Interact. 87:1993;295.
7. Quinn D.M. Chem. Rev. 87:1987;955.
8. Abdel-Aal Y.A.I., Hammock B.D. Science. 233:1986;1073.
9. Kamita, S. G.; Hinton, A. C.; Wheelock, C. E.; Wogulis, M. D.; Wilson, D. K.; Wolf, N. M.; Stok, J. E.; Hock, B.; Hammock, B. D. Insect Biochem. Molec. Biol. (In press).
10. Riddiford, L. M. In Comprehensive Insect Physiology, Biochemistry, and Pharmacology vol. 8; Pergamon: New York, 1985; p 37.
11. Thomas B.A., Church W.B., Lane T.R., Hammock B.D. Proteins. 34:1999;184.
12. Székács, A.; Bordás, B.; Hammock, B. D. In Rational Approaches to Structure, Activity, and Ecotoxicology of Agrochemicals; Draber, W.; Fujita, T., eds. CRC: Boca Raton, FL, 1992; p 219.
13. Lienhard G.E. Science. 180:1973;149.
14. Segel, I. H. In Biochemical Calculations, 2nd ed.; John Wiley & Sons: New York, 1976.
15. Nair H.K., Lee K., Quinn D.M. J. Am. Chem. Soc. 115:1993;9939.
16. Wheelock C.E., Severson T.F., Hammock B.D. Chem. Res. Tox. 14:2001;1563.
17. Amour A., Reboud-Ravaux M., de Rosny E., Abouabdellah A., Begue J.P., Bonnet-Delpon D., Le Gall M. J. Pharm. Pharmacol. 50:1998;593.
18. Boger D.L., Sato H., Lerner A.E., Austin B.J., Patterson J.E., Patricelli M.P., Cravatt B.F. Bioorganic Med. Chem. Let. 9:1999;265.
19. Edwards P.D., Andisik D.W., Bryant C.A., Ewing B., Gomes B., Lewis J.J., Rakiewicz D., Steelman G., Strimpler A., Trainor D.A., Tuthill P.A., Mauger R.C., Veale C.A., Wildonger R.A., Williams J.C., Wolanin D.J., Zottola M. J. Med. Chem. 40:1997;1876.
20. Linderman R.J., Upchurch L., Lonikar M., Venkatesh K., Roe R.M. Pestic. Biochem. Physiol. 35:1989;291.
21. Linderman R.J., Leazer J., Venkatesh K., Roe R.M. Pestic. Biochem. Physiol. 29:1987;266.
22. Roe R.M., Linderman R.J., Lonikar M., Venkatesh K., Abdel-Aal Y.A.I., Leazer J., Upchurch L. J. Agric. Food Chem. 38:1990;1274.
23. Ward V.K., Bonning B.C., Huang T., Shiotsuki T., Griffeth V.N., Hammock B.D. Int. J. Biochem. 24:1992;1933.
24. Wheelock C.E., Colvin M.E., Uemura I., Olmstead M.M., Nakagawa Y., Sanborn J.R., Jones A.D., Hammock B.D. J. Med. Chem. 45:2002;5576.
25. Linderman, R. J.; Jamois, E. A.; Roe, R. M. In Reviews in Pesticide Toxicology; North Carolina State University: Raleigh, 1991; p 261.
26. Hammock B.D., Wing K.D., McLaughlin J., Lovell V.M., Sparks T.C. Pestic. Biochem. Physiol. 17:1982;76.
27. Linderman R.J., Leazer J., Roe R.M., Venkatesh K., Selinsky B.S., London R.E. Pestic. Biochem. Phys. 31:1988;187.
28. Gelb M.H., Svaren J.P., Abeles R.H. Biochem. 24:1985;1813.
29. Christianson D.W., Lipscomb W.N. J. Am. Chem. Soc. 108:1986;4998.
30. Roe R.M., Anspaugh D.D., Venkatesh K., Linderman R.J., Graves D.M. Arch. Insect Biochem. Physiol. 36:1997;165.
31. Asao, M.; Shimizu, R.; Nakao, K.; Fujita, T. QREG, 2.05 ed.; Chemistry Program Exchange: Kyoto, Japan.
32. Hansch, C. ClogP, 4.0 ed.; BioByte: Claremont, CA, USA.
33. Hansch, C.; Leo, A.; Haekman, D. In Exploring QSAR: Hydrophobic, electronic and steric constants. American Chemical Society: Washington, DC, USA, 1995; p 584.
34. Olmstead M.M., Musker W.K., Hammock B.D. Acta Crystallogr. C43:1987;1726.
35. Fujita T., Hansch C. J. Med. Chem. 10:1967;991.
36. Sparks T., Hammock B. J. Insect. Physiol. 25:1979;551.
37. Rudnicka M., Hammock B. Insect Biochem. 11:1981;437.
38. Guthrie J.P. Can. J. Chem. 53:1975;898.
39. Hammock B.D., Abdel-Aal A.I., Mullin C.A., Hanzlik T.N., Roe R.M. Pestic. Biochem. Phys. 22:1984;209.
40. Shiotsuki T., Huang T.L., Hammock B.D. J. Pestic. Sci. 19:1994;321.
41. Morgan R.S., McAdon J.M. Int. J. Peptide Protein Res. 15:1980;177.
42. Székács A., Halarnkar P.P., Olmstead M.M., Prag K.A., Hammock B.D. Chem. Res. Toxicol. 3:1990;325.
43. Akamatsu M., Nishimura K., Osabe H., Ueno T., Fujita T. Pestic. Biochem. Physiol. 48:1994;15.
44. Avery M.A., Alvim-Gaston M., Rodrigues C.R., Barreiro E.J., Cohen F.E., Sabnis Y.A., Woolfrey J.R. J. Med. Chem. 45:2002;292.
45. Davydov D.R., Hui Bon Hoa G., Peterson J.A. Biochemistry. 38:1999;751.