Requirements for mammalian carboxylesterase inhibition by substituted ethane-1,2-diones

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 15, 2011, Pages 4635-4643

  Parkinson, Elizabeth I ^a,b   Jason Hatfield, M ^a   Tsurkan, Lyudmila ^a   Hyatt, Janice L ^a   Edwards, Carol C ^a   Hicks, Latorya D ^a   Yan, Bing ^a   Potter, Philip M ^a  

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

^b RHODES COLLEGE   (United States)

Author keywords

Carboxylesterase; Ethane 1,2 diones; Inhibitor

Indexed keywords

1 BROMO 1,4 DIPHENYLBUTANE 2,3 DIONE; 1 PHENYL 1,2 PROPANEDIONE; 1 PHENYL 2 ALKYL 1,2 DIONE DERIVATIVE; 1 PHENYL 2 OCTANE 1,2 DIONE; 1,2 DICYCLOHEXYLETHANE 1,2 DIONE; 1,4 DIBROMO 1,4 DIPHENYLBUTANE 2,3 DIONE; 1,4 DIPHENYLBUTANE 2,3 DIONE; 1,4 DIPHENYLBUTANE 2,3 DIONE DERIVATIVE; 2,3 BUTANEDIONE; BENZIL; BUTYRYLCHOLINESTERASE INHIBITOR; CARBOXYLESTERASE; CHOLINESTERASE INHIBITOR; DIPHENYL ETHANEDIOATE; DODECANE 6,7 DIONE; ENZYME INHIBITOR; HEXADECANE 8,9 DIONE; HEXANE 3,4 DIONE; IRINOTECAN; OCTADECANE 9,10 DIONE; OCTANE 4,5 DIONE; OXANILIDE; PHENYL 1,2 BUTANEDIONE; PHENYL 1,2 HEPTANEDIONE; PHENYL 1,2 HEXANEDIONE; PHENYL 1,2 OCTANEDIONE; PHENYL 1,2 PENTANEDIONE; PHENYL 1,2 PROPANEDIONE; TETRADECANE 7,8 DIONE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; DRUG CYTOTOXICITY; DRUG METABOLISM; DRUG SYNTHESIS; ELECTROPHILICITY; ENZYME ACTIVE SITE; ENZYME ASSAY; ENZYME INHIBITION; ENZYME SUBSTRATE; ENZYME SYNTHESIS; GROWTH INHIBITION; HUMAN; HYDROLYSIS; HYDROPHOBICITY; IC 50; MELTING POINT; MOLECULAR DYNAMICS; NUCLEOPHILICITY;

ANIMALS; CARBOXYLESTERASE; CELL LINE; CELL PROLIFERATION; ENZYME INHIBITORS; ETHANE; HUMANS; INHIBITORY CONCENTRATION 50; MOLECULAR DYNAMICS SIMULATION;

ANIMALIA; MAMMALIA;

EID: 79960559858     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.06.012     Document Type: Article

References (40)

1. J. Cashman, B. Perroti, C. Berkman, and J. Lin Environ. Health Perspect. 104 1996 23
2. P.M. Potter, and R.M. Wadkins Curr. Med. Chem. 13 2006 1045
3. M.R. Redinbo, and P.M. Potter Drug Discovery Today 10 2005 313
4. M. Mori, M. Hosokawa, Y. Ogasawara, E. Tsukada, and K. Chiba FEBS Lett. 458 1999 17
5. C.D. Fleming, S. Bencharit, C.C. Edwards, J.L. Hyatt, L. Tsurkan, F. Bai, C. Fraga, C.L. Morton, E.L. Howard-Williams, P.M. Potter, and M.R. Redinbo J. Mol. Biol. 352 2005 165
6. R. Khanna, C.L. Morton, M.K. Danks, and P.M. Potter Cancer Res. 60 2000 4725
7. M.K. Ross, A. Borazjani, C.C. Edwards, and P.M. Potter Biochem. Pharmacol. 71 2006 657
8. M.K. Ross, P.M. Potter, and A. Borazjani Toxicol. Sci. 84 2005 A1569
9. T. Satoh, M. Hosokawa, R. Atsumi, W. Suzuki, H. Hakusui, and E. Nagai Biol. Pharm. Bull. 17 1994 662
10. J. Zhang, J.C. Burnell, N. Dumaual, and W.F. Bosron J. Pharmacol. Exp. Ther. 290 1999 314
11. R. Humerickhouse, K. Lohrbach, L. Li, W. Bosron, and M. Dolan Cancer Res. 60 2000 1189
12. Y.H. Hsiang, and L.F. Liu Cancer Res. 48 1988 1722
13. A. Tanizawa, A. Fujimori, Y. Fujimori, and Y. Pommier J. Natl. Cancer Inst. 86 1994 836
14. M.K. Danks, C.L. Morton, E.J. Krull, P.J. Cheshire, L.B. Richmond, C.W. Naeve, C.A. Pawlik, P.J. Houghton, and P.M. Potter Clin. Cancer Res. 5 1999 917
15. P.M. Potter, C.A. Pawlik, C.L. Morton, C.W. Naeve, and M.K. Danks Cancer Res. 52 1998 2646
16. M. Wierdl, C.L. Morton, J.K. Weeks, M.K. Danks, L.C. Harris, and P.M. Potter Cancer Res. 61 2001 5078
17. M.J. Hatfield, L. Tsurkan, M. Garrett, T. Shaver, C.C. Edwards, J.L. Hyatt, L.D. Hicks, and P.M. Potter Biochem. Pharmacol. 81 2011 24
18. J.L. Hyatt, T. Moak, J.M. Hatfield, L. Tsurkan, C.C. Edwards, M. Wierdl, M.K. Danks, R.M. Wadkins, and P.M. Potter J. Med. Chem. 50 2007 1876
19. J.L. Hyatt, V. Stacy, R.M. Wadkins, K.J. Yoon, M. Wierdl, C.C. Edwards, M. Zeller, A.D. Hunter, M.K. Danks, G. Crundwell, and P.M. Potter J. Med. Chem. 48 2005 5543
20. J.L. Hyatt, R.M. Wadkins, L. Tsurkan, L.D. Hicks, M.J. Hatfield, C.C. Edwards, C.R. Ii, S.A. Cantalupo, G. Crundwell, M.K. Danks, R.K. Guy, and P.M. Potter J. Med. Chem. 50 2007 5727
21. R.M. Wadkins, J.L. Hyatt, X. Wei, K.J. Yoon, M. Wierdl, C.C. Edwards, C.L. Morton, J.C. Obenauer, K. Damodaran, P. Beroza, M.K. Danks, and P.M. Potter J. Med. Chem. 48 2005 2905
22. J.L. Hyatt, L. Tsurkan, M. Wierdl, C.C. Edwards, M.K. Danks, and P.M. Potter Mol. Cancer Ther. 5 2006 2281
23. F. Babudri, V. Fiandanese, G. Marchese, and A. Punzi Tetrahedron Lett. 36 1995 7305
24. C.L. Morton, and P.M. Potter Mol. Biotechnol. 16 2000 193
25. M.D. Santana, G. Garcia, M. Julve, F. Lloret, J. Perez, M. Liu, F. Sanz, J. Cano, and G. Lopez Inorg. Chem. 43 2004 2132
26. H.O. Jones, and H.S. Tasker J. Chem. Soc. 95 1909 1904
27. N.S. Srinivasan, and D.G. Lee J. Org. Chem. 44 1979 1574
28. R.M. Wadkins, J.L. Hyatt, K.J. Yoon, C.L. Morton, R.E. Lee, K. Damodaran, P. Beroza, M.K. Danks, and P.M. Potter Mol. Pharmacol. 65 2004 1336
29. J.L. Webb Enzyme and Metabolic Inhibitors, General Principles of Inhibition Vol. 1 1963 Academic Press New York
30. Akaike, H. In Information Theory and An Extension of The Maximum Likelihood Principle, Second International Symposium on Information Theory; Petrov, B. N.; Csaki, F., Eds.; Budapest, Akademiai Kiado, 1973, pp 267-281.
31. H. Akaike IEEE Trans. Automatic Control AC-19 1974 716
32. B.P. Doctor, L. Toker, E. Roth, and I. Silman Anal. Biochem. 166 1987 399
33. G.L. Ellman, K.D. Courtney, V. Anders, and R.M. Featherstone Biochem. Pharmacol. 7 1961 88
34. C.L. Morton, R.M. Wadkins, M.K. Danks, and P.M. Potter Cancer Res. 59 1999 1458
35. R.M. Wadkins, P.M. Potter, B. Vladu, J. Marty, G. Mangold, S. Weitman, G. Manikumar, M.C. Wani, M.E. Wall, and D.D. Von-Hoff Cancer Res. 59 1999 3424
36. S. Guichard, C.L. Morton, E.J. Krull, C.F. Stewart, M.K. Danks, and P.M. Potter Clin. Cancer Res. 4 1998 3089
37. M.K. Danks, C.L. Morton, C.A. Pawlik, and P.M. Potter Cancer Res. 58 1998 20
38. P.J. Stephens, F.J. Devlin, C.F. Chabalowski, and M.J. Frisch J. Phys. Chem. 98 1994 11623
39. G.A. Petersson, A. Bennett, T.G. Tensfeldt, M.A. Al-Laham, W.A. Shirley, and J. Mantzaris J. Chem. Phys. 89 1988 2193
40. H. Stetter, and R.Y. Raemsch Synthesis 6 1981 477