Analysis of the inhibition of mammalian carboxylesterases by novel fluorobenzoins and fluorobenzils

Bioorganic and Medicinal Chemistry

Volumn 15, Issue 11, 2007, Pages 3801-3817

  Hicks, Latorya D ^a   Hyatt, Janice L ^a   Moak, Teri ^b   Edwards, Carol C ^a   Tsurkan, Lyudmila ^a   Wierdl, Monika ^a   Ferreira, Antonio M ^a   Wadkins, Randy M ^b   Potter, Philip M ^a  

^a ST JUDE CHILDREN S RESEARCH HOSPITAL   (United States)

^b UNIVERSITY OF MISSISSIPPI   (United States)

Author keywords

Carboxylesterase; Fluorobenzil; Fluorobenzoin; Inhibitor

Indexed keywords

1,2 BIS(2 FLUOROPHENYL) 2 HYDROXYETHANONE; 1,2 BIS(2 FLUOROPHENYL)ETHANE 1,2 DIONE; 1,2 BIS(2,3 DIFLUOROPHENYL) 2 HYDROXYETHANONE; 1,2 BIS(2,3 DIFLUOROPHENYL)ETHANE 1,2 DIONE; 1,2 BIS(2,3,4 TRIFLUOROPHENYL) 2 HYDROXYETHANONE; 1,2 BIS(2,3,5 TRIFLUOROPHENYL) 2 HYDROXYETHANONE; 1,2 BIS(2,4 DIFLUOROPHENYL) 2 HYDROXYETHANONE; 1,2 BIS(2,4 DIFLUOROPHENYL)ETHANE 1,2 DIONE; 1,2 BIS(2,5 DIFLUOROPHENYL) 2 HYDROXYETHANONE; 1,2 BIS(2,5 DIFLUOROPHENYL)ETHANE 1,2 DIONE; 1,2 BIS(2,6 DIFLUOROPHENYL) 2 HYDROXYETHANONE; 1,2 BIS(2,6 DIFLUOROPHENYL)ETHANE 1,2 DIONE; 1,2 BIS(3 FLUOROPHENYL) 2 HYDROXYETHANONE; 1,2 BIS(3 FLUOROPHENYL)ETHANE 1,2 DIONE; 1,2 BIS(3,4 DIFLUOROPHENYL) 2 HYDROXYETHANONE; 1,2 BIS(3,4 DIFLUOROPHENYL)ETHANE 1,2 DIONE; 1,2 BIS(3,4,5 TRIFLU0ROPHENYL) 2 HYDROXYETHANONE; 1,2 BIS(3,5 DIFLUOROPHENYL) 2 HYDROXYETHANONE; 1,2 BIS(3,5 DIFLUOROPHENYL)ETHANE 1,2 DIONE; 1,2 BIS(4 FLUOROPHENYL) 2 2 HYDROXYETHANONE; 1,2 BIS(4 FLUOROPHENYL)ETHANE 1,2 DIONE; 1,2 BIS[3 (TRIFLUOROMETHYL)PHENYL] 2 HYDROXYETHANONE; 1,2 BIS[4 (TRIFLUOROMETHYL)PHENYL] 2 HYDROXYETHANONE; BENZALDEHYDE DERIVATIVE; BENZIL(DIPHENYLETHANE 1,2 DIONE); BENZOIN; BENZOIN(1,2 DIPHENYL 2 HYDROXY ETHANONE); CARBOXYLESTERASE; ENZYME INHIBITOR; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; CORRELATION ANALYSIS; DRUG ACTIVITY; DRUG SCREENING; DRUG SYNTHESIS; ENZYME INHIBITION; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

BENZOIN; CARBOXYLIC ESTER HYDROLASES; ENZYME INHIBITORS; HUMANS; HYDROCARBONS, FLUORINATED; PHENYLGLYOXAL; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

MAMMALIA;

EID: 34247357853     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2007.03.012     Document Type: Article

References (32)

1. Cashman J., Perroti B., Berkman C., and Lin J. Environ. Health Perspect. 104 (1996) 23
2. Khanna R., Morton C.L., Danks M.K., and Potter P.M. Cancer Res. 60 (2000) 4725
3. Redinbo M.R., Bencharit S., and Potter P.M. Biochem. Soc. Trans. 31 (2003) 620
4. Redinbo M.R., and Potter P.M. Drug Discov. Today 10 (2005) 313-325
5. Molinoff P.B., and Ruddon R.W. In: Hardman J.G., and Limbird L.E. (Eds). Goodman & Gilman's the Pharmacological Basis of Therapeutics (1996), McGraw-Hill, New York 1905
6. Wadkins R.M., Hyatt J.L., Yoon K.J., Morton C.L., Lee R.E., Damodaran K., Beroza P., Danks M.K., and Potter P.M. Mol. Pharmacol. 65 (2004) 1336
7. Beroza P., Villar H.O., Wick M.M., and Martin G.R. Drug Discov. Today 7 (2002) 807
8. Dixon S.L., and Villar H.O. J. Chem. Inf. Comput. Sci. 38 (1998) 1192
9. Kauvar L.M., Higgins D.L., Villar H.O., Sportsman J.R., Engqvist-Goldstein A., Bukar R., Bauer K.E., Dilley H., and Rocke D.M. Chem. Biol. 2 (1995) 107
10. Wadkins R.M., Hyatt J.L., Wei X., Yoon K.J., Wierdl M., Edwards C.C., Morton C.L., Obenauer J.C., Damodaran K., Beroza P., Danks M.K., and Potter P.M. J. Med. Chem. 48 (2005) 2905
11. Hyatt J.L., Stacy V., Wadkins R.M., Yoon K.J., Wierdl M., Edwards C.C., Zeller M., Hunter A.D., Danks M.K., Crundwell G., and Potter P.M. J. Med. Chem. 48 (2005) 5543
12. Wadkins R.M., Morton C.L., Weeks J.K., Oliver L., Wierdl M., Danks M.K., and Potter P.M. Mol. Pharmacol. 60 (2001) 355
13. Lundstedt T., Seifert E., Abramo L., Thelin B., Nystrom A., Pettersen J., and Bergman B. Chemometr. Intell. Lab. Syst. 42 (1998) 3
14. Mohrig J.R., Hammond C.N., Schatz P.F., and Morrill T.C. Modern Projects and Experiments in Organic Chemistry: Miniscale and Williamson Microscale (2003), W.H. Freeman & Co., New York 367-368
15. Demir A.S., Sesenoglu O., Eren E., Hosrik B., Pohl M., Janzen E., Kolter D., Feldmann R., Dunkelmann P., and Muller M. Adv. Synth. Catal. 344 (2002) 96
16. Weiss M., and Appel M. J. Am. Chem. Soc. 70 (1948) 3666
17. Morton C.L., and Potter P.M. Mol. Biotechnol. 16 (2000) 193
18. Schwer H., Langmann T., Daig R., Becker A., Aslanidis C., and Schmitz G. Biochem. Biophys. Res. Commun. 233 (1997) 117
19. Munger J.S., Shi G.P., Mark E.A., Chin D.T., Gerard C., and Chapman H.A. J. Biol. Chem. 266 (1991) 18832
20. Potter P.M., Pawlik C.A., Morton C.L., Naeve C.W., and Danks M.K. Cancer Res. 52 (1998) 2646
21. Doctor B.P., Toker L., Roth E., and Silman I. Anal. Biochem. 166 (1987) 399
22. Ellman G.L., Courtney K.D., Anders V., and Featherstone R.M. Biochem. Pharmacol. 7 (1961) 88
23. Webb J.L. Enzyme and Metabolic Inhibitors. General Principles of Inhibition Vol. 1 (1963), Academic Press Inc., New York
24. Akaike, H. In Information theory and an extension of the maximum likelihood principle, Petrov, B. N.; Csaki, F., Eds.; Second International Symposium on Information Theory, Budapest, Akademiai Kiado: Budapest, 1973; pp 267-281.
25. Akaike H. IEEE Trans. Autom. Control AC-19 (1974) 716
26. Stephens P.J., Devlin F.J., Chabalowski C.F., and Frisch M.J. J. Phys. Chem. 98 (1994) 11623
27. Petersson G.A., Bennett A., Tensfeldt T.G., Al-Laham M.A., Shirley W.A., and Mantzaris J. J. Chem. Phys. 89 (1988) 2193
28. Buckley A., Chapman N.B., and Schorter J. J. Chem. Soc. B-Phys. Org. 2 (1969) 195
29. Jakalian A., Jack D.B., and Bayly C.I. J. Med. Chem. 23 (2002) 1623
30. Vedani A., and Dobler M. J. Med. Chem. 45 (2002) 2139
31. Vedani A., and Dobler M. Quant. Struct.-Act. Relat. 21 (2002) 382
32. Kraulis P.J. J. Appl. Crystallogr. 24 (1991) 946