Ortho effects for inhibition mechanisms of butyrylcholinesterase by o-substituted phenyl N-butyl carbamates and comparison with acetylcholinesterase, cholesterol esterase, and lipase

Chemical Research in Toxicology

Volumn 18, Issue 7, 2005, Pages 1124-1131

  Lin, Gialih ^a   Lee, Yu Ru ^a   Liu, Yu Chen ^a   Wu, Yon Gi ^a  

^a NATIONAL CHUNG HSING UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLCHOLINESTERASE; CARBAMIC ACID DERIVATIVE; CARBARIL; CHOLESTEROL ESTERASE; CHOLINESTERASE; DONEPEZIL; EDROPHONIUM; GALANTAMINE; PHYSOSTIGMINE; RIVASTIGMINE; TACRINE; TRIACYLGLYCEROL LIPASE;

ALZHEIMER DISEASE; ARTICLE; CONFORMATION; CONTROLLED STUDY; DRUG MECHANISM; DRUG POTENCY; ELECTRON TRANSPORT; ENZYME INHIBITION; ENZYME KINETICS; HYDROGEN BOND;

ACETYLCHOLINESTERASE; BINDING SITES; BUTYRYLCHOLINESTERASE; CARBAMATES; CHOLINESTERASE INHIBITORS; KINETICS; LIPASE; MOLECULAR STRUCTURE; SUBSTRATE SPECIFICITY;

EID: 22544452692     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx050014o     Document Type: Article

References (44)

1. Massoulie, J., Pezzementi, L., Bon, S., Krejci, E., and Vallette, F. M. (1993) Molecular and cellular biology of cholinesterase. Prog. Neurobiol. 41, 31-91.
2. Xie, W.-H., Stribley, J. A., Chatonnet, A., Wilder, P. J., Rizzino, A., McComb, R. D., Taylor, P., Hinrichs, S. H., and Lockridge, O. (2000) Postnatal developmental delay and supersensitivity to organophosphate in gene-targeted mice lacking acetylcholinesterase. J. Pharmacol. Exp. Ther. 293, 869-902.
3. Zhan, C.-G., Zheng, F., and Landry, D. W. (2003) Fundamental reaction mechanism for cocaine hydrolysis in human butyrylcholinesterase. J. Am. Chem. Soc. 125, 2462-2474.
4. Masson, P., Froment, M.-T., Fort, S., Ribes, F., Bee, N., Balny, C., and Schopfer, L. M. (2002) Butyrylcholinesterase-catalyzed hydrolysis of N-methylindoxyl acetate: analysis of volume changes upon reaction and hysteretic behavior. Biochim. Biophys. Acta 1597, 229-243.
5. Loudwig, S., Nicolet, Y., Masson, P., Fontecilla-Camps, J. C., Bon, S., Nachon, F., and Goeldner, M. (2003) Photoreversible inhibition of cholinesterase: catalytic serine-labeled caged butyrylcholinesterase. ChemBioChem 4, 762-767.
6. Quinn, D. M. (1987) Acetylcholinesterase: enzyme structure, reaction dynamics, and virtual transition states. Chem. Rev. 87, 955-979.
7. Sussman, J. L., Harel, M., Frolow, F., Oefner, C., Goldman, A., Toker, L., and Silman, I. (1991) Atomic structure of acetylcholinesterase from Torpedo californica: a prototypic acetylcholine-binding protein. Science 253, 872-879.
8. Harel, M., Schalk, I., Ehret-Sabatier, L., Bouet, F., Goeldner, M., Hirth, L., Axelsen, P. H., Silman, I., and Sussman, J. L. (1993) Quaternary ligand binding to aromatic residues in the active-site gorge of acetylcholinesterase. Proc. Natl. Acad. Sci. U.S.A. 90, 9031-9035.
9. Harel, M., Quinn, D. M., Nair, H. K., Silman, I., and Sussman, J. L. (1996) The X-ray structure of a transition state analog complex reveals the molecular origins of the catalytic power and substrate specificity of acetylcholinesterase. J. Am. Chem. Soc. 118, 2340-2346.
10. Savini, L., Gaeta, A., Fattorusso, C., Catalanotti, B., Campiani, G., Chiasserini, L., Pellerano, C., Novellino, E., McKissic, D., and Saxena, A. (2003) Specific targeting of acetylcholinesterase and butyrylcholinesterase recognition sites. Rational design of novel, selective, and highly potent cholinesterase inhibitors. J. Med. Chem. 46, 1-4.
11. Masson, P., Xie, W., Forment, M.-T., Levitsky, V., Fortier, P.-L., Albaret, C., and Lockridge, O. (1999) Interaction between the peripheral site residues of human butyrylcholinesterase, D70 and Y332, in binding and hydrolysis of substrate. Biochim. Biophys. Acta 1433, 281-293.
12. Lin, G., Tsai, H.-J., and Tsai, Y.-H. (2003) Cage amines as the stopper inhibitors of cholinesterases. Bioorg. Med. Chem. Lett. 13, 2887-2890.
13. Mesulam, M. (2000) Neuroanatomy of cholinesterase in the normal human brain and in Alzheimer's disease. In Cholinesterase and Cholinesterase Inhibitors (Giacobini, E., Ed.) pp 121-137, Martin Donitz, London.
14. Giacobini, E. (2003) Cholinergic functions in Alzheimer's disease. Int. J. Geriatr. Psychiatry 18, S1-S5.
15. Greig, N. H., Utsuki, T., Yu, Q.-S., Zhu, X., Holloway, H. W., Perry, T., Lee, B., Ingram, D. K., and Lahiri, D. K. (2001) A new therapeutic target in Alzheimer's disease treatment: attention to butyrylcholinesterase. Curr. Med. Res. Opin. 17, 1-6.
16. Mesulam, M. M., Guillozet, A., Shaw, P., Levey, A., Duysen, E., G., and Lockridge, O. (2002) Acetylcholinesterase knockouts establish centeral cholinergic pathways and can use butyrylcholinesterase to hydrolyze acetylcholine. Neuroscience 110, 627-639.
17. Giacobini, E., Spiegel, R., Enz, A., Veroff, A. E., and Cutler, N. R. (2002) Inhibition of acetyl- and butyryl-cholinesterase in the cerebrospinal fluid of patients with Alzheimer's disease by rivastigmine: correlation with cognitive benefit. J. Neural Transm. 109, 1053-1065.
18. Yu, Q.-S., Holloway, H. W., Flippen-Anderson, J. L., Hoffman, B., Brossi, A., and Greig, N. H. (2001) Methyl analogues of the experimental Alzheimer's drug phenserine: synthesis and structure/activity relationships for acetyl- and butyrylcholinesterase inhibitory action. J. Med. Chem. 44, 4062-4071.
19. Bar-On, P., Millard, C. B., Harel, M., Dvir, H., Enz, A., Sussman, J. L., and Silman, I. (2002) Kinetic and structural studies on the interaction of cholinesterase with anti-Alzheimer drug rivastigmine. Biochemistry 41, 3555-3564.
20. Bartolucci, C., Perola, E., Cellai, L., Brufani, M., and Lamba, D. (1999) Back door opening implied by the crystal structure of a carbamoylated acetylcholinesterase. Biochemistry 38, 5714-5719.
21. Lin, G., Lai, C.-Y., and Liao, W.-C. (1999) Molecular recognition by acetylcholinesterase at the peripheral anionic site: structure-activity relationships for inhibitions by aryl carbamates. Bioorg. Med. Chem. 7, 2683-2689.
22. Lin, G., Lai, C.-Y., Liao, W.-C., Liao, P.-S., and Chan, C.-H. (2003) Structure-activity relationships as probes to the inhibition mechanisms of acetylcholinesterase by aryl carbamates. I. The steady-state kinetics, J. Chin. Chem. Soc. 50, 1259-1265.
23. Lin, G. (2004) Structure-activity relationships as probes to the inhibition mechanisms of acetylcholinesterase by aryl carbamates. II. Hammett-Taft cross-interaction correlations. J. Chin. Chem. Soc. 51, 432-429.
24. Lin, G., Liu, Y.-C., Lin, Y.-F., and Wu, Y.-G. (2004) Ortho effects in quantitative structure-activity relationships for acetylcholinesterase inhibition by aryl carbamates, J. Enzyme Inhib. Med. Chem. 19, 395-401.
25. Lin, G., Liao, W.-C., Chan, C.-H., Wu, Y.-H., Tsai, H.-J., and Hsieh, C.-W. (2004) Quantitative structure-activity relationships for the pre-steady-state acetylcholinesterase inhibition by carbamates. J. Biochem. Mol. Toxicol. 18, 353-360.
26. Lin, G., Tseng, H.-C., Chio, A.-C., Tseng, T.-M., and Tsai, B.-Y. (2005) A rate determining step change in the pre-steady state of acetylcholinesterase inhibitions by 1,n-alkane-di-N-butycarbamates. Bioorg. Med. Chem. Lett. 15, 951-955.
27. Lin, G., Chen, G.-H., and Ho, H.-C. (1998) Conformationally restricted carbamate inhibitors of horse serum butyrylcholinesterase, Bioorg. Med. Chem. Lett. 8, 2747-2750.
28. Baron, R. L. (1991) Carbamate insecticides. In Handbook of Pesticide Toxicology (Hayes, W. J. J., and Laws, E. R. J., Eds.) Vol. 3, Academic Press, New York.
29. Aldrige, W. N., and Reiner, E. (1972) Enzyme Inhibitors as Substrates (Neuberger, A., and Tatun, E. L., Eds.) pp123-145, North-Holland Publishing Co., Amsterdam.
30. Hart, G. J., and O'Brien, R. D. (1973) Recording spectrophotometric method for determination of dissociation and phosphorylation constants for the inhibition of acetylcholinesterase by organophosphates in the presence of substrate. Biochemistry 12, 2940-2945.
31. Hosie, L., Sutton, L. D., and Quinn, D. M. (1987) p-Nitrophenyl and cholesteryl-N-alkyl carbamates as inhibitors of cholesterol esterase. J. Biol. Chem. 262, 260-264.
32. Feaster, S. R., Lee, K., Baker, N., Hui, D. Y., and Quinn, D. M. (1996) Molecular recognition by cholesterol esterase of active site ligands: structure-reactivity effects for inhibition by aryl carbamates and subsequent carbamylenzyme turnover. Biochemistry 35, 16723.
33. Feaster, S. R., and Quinn, D. M. (1997) Mechanism-based inhibitors of mammalian cholesterol esterase. Methods Enzymol. 286, 231-252.
34. Lin, G., and Lai, C.-Y. (1995) Hammett analysis of the inhibition of pancreatic cholesterol esterase by substituted phenyl-N-butylcarbamate. Tetrahedron Lett. 36, 6117-6120.
35. Lin, G., Shieh, C.-T., Ho, H.-C., Chouhwang, J.-Y., Lin, W.-Y., and Lu, C.-P. (1999) Structure-reactivity relationships for the inhibition mechanism at the second alkyl-chain-binding site of cholesterol esterase and lipase. Biochemistry 38, 9971-9981.
36. Lin, G., Lai, C.-Y., Liao, W.-C., Kuo, B.-H., and Lu, C.-P. (2000) Structure-reactivity relationships as probes for the inhibition mechanism of cholesterol esterase by aryl carbamates. I. Steady-state kinetics. J. Chin. Chem. Soc. 47, 489-500.
37. Lin, G., Liu, Y.-C., Wu, Y.-G., and Lee, Y.-R. (2003) Ortho effects in quantitative structure activity relationships for lipase inhibition mechanisms by aryl carbamates. QSAR Comb. Sci. 22, 852-858.
38. Lin, G., Liu, Y.-C., and Wu, Y.-G. (2004) Ortho effects and cross interaction correlations for the mechanism of cholesterol esterase inhibition by aryl carbamates. J. Phys. Org. Chem. 17, 707-714.
39. Abeles, R. H., and Maycock, A. L. (1976) Suicide enzyme inactivators. Acc. Chem. Res. 313-319.
40. Isaacs, N. (1995) Physical Organic Chemistry, 2nd ed., Longman, Essex, U.K.
41. Lowry, T. H., and Richardson, K. S. (1992) Mechanism and Theory in Organic Chemistry, 3rd ed., Harper & Row, New York.
42. Fujita, T., and Nishioka, T. (1976) The analysis of the ortho effect. Prog. Phys. Org. Chem. 12, 49-89.
43. Ellman, C. L., Courtney, K. D., Andres, V. J., and Featherstone, R. M. (1961) A new rapid colorimetric determination of acetylcholinesterase activity. Biochem. Pharm. 7, 88-95.
44. Zhang, Y., Kua, J., and McCammon, J. A. (2002) Role of the catalytic triad and oxyanion hole in acetylcholinesterase catalysis: an ab initio QM/MM study. J. Am. Chem. Soc. 124, 10572-10577.