Carbamates with differential mechanism of inhibition toward acetylcholinesterase and butyrylcholinesterase

Journal of Medicinal Chemistry

Volumn 51, Issue 14, 2008, Pages 4200-4212

  Darvesh, Sultan ^a,b,d   Darvesh, Katherine V ^b   McDonald, Robert S ^b   Mataija, Diane ^b   Walsh, Ryan ^a   Mothana, Sam ^b   Lockridge, Oksana ^c   Martin, Earl ^b  

^a DALHOUSIE UNIVERSITY   (Canada)

^b MOUNT SAINT VINCENT UNIVERSITY   (Canada)

^c UNIVERSITY OF NEBRASKA MEDICAL CENTER   (United States)

^d Camp Hill Veterans' Memorial Building 1 ^*  (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

1 NAPHTHYL CARBAMATE; 3 (N,N DIMETHYLAMINO)PHENYL CARBAMATE; 4 BIPHENYL CARBAMATE; 4 TERT BUTYLPHENYL CARBAMATE; ACETYLCHOLINESTERASE; ANION; CARBAMIC ACID DERIVATIVE; CATION; CHOLINESTERASE; PHENOTHIAZINE DERIVATIVE; SERINE;

ARTICLE; COVALENT BOND; DRUG POTENCY; DRUG SYNTHESIS; ENZYME ACTIVE SITE; ENZYME INHIBITION; ENZYME KINETICS; ENZYME MECHANISM; MOLECULAR INTERACTION; MUTANT; STRUCTURE ACTIVITY RELATION;

ACETYLCHOLINESTERASE; BUTYRYLCHOLINESTERASE; CARBAMATES; CATALYSIS; CHOLINESTERASE INHIBITORS; HUMANS; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 47749102491     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm8002075     Document Type: Article

References (35)

1. Silver, A. The Biology of Cholinesterases; Elsevier: Amsterdam, 1974.
2. Giacobini, E. Butyrylcholinesterase: Its Function and Inhibitors; Martin Dunitz: London and New York, 2003.
3. Darvesh, S.; Hopkins, D. A.; Geula, C. Neurobiology of butyrylcholinesterase. Nat. Rev. Neurosci. 2003, 4, 131-138.
4. Birks, J. Cholinesterase inhibitors for Alzheimer's disease. Cochrane Database of Systematic Reviews 2006, 1, Art. No. CD005593, DOI: 10.1002/14651858.CD005593.
5. Kryger, G.; Silman, I.; Sussman, J. L. Three-dimensional structure of a complex of E2020 with acetylcholinesterase from Torpedo californica. J. Physiol. Paris 1998, 92, 191-194.
6. Greenblatt, H. M.; Kryger, G.; Lewis, T.; Silman, I.; Sussman, J. L. Structure of acetylcholinesterase complexed with (-)-galanthamine at 2.3 A resolution. FEBS Lett. 1999, 463, 321-326.
7. Darvesh, S.; Walsh, R.; Kumar, R.; Caines, A.; Roberts, S.; Magee, D.; Rockwood, K.; Martin, E. Inhibition of human cholinesterases by drugs used to treat Alzheimer disease. Alzheimer Dis. Assoc. Disord. 2003, 17, 117-126.
8. Taylor, P. Anticholinesterase agents. In Goodman & Gilman's The Pharmacological Basis of Therapeutics 11th ed.; Brunton, L. L., Lazo, J. S., Parker, K. L., Eds.; McGraw-Hill: New York, 2006; pp 201-216..
9. Weinstock, M.; Razin, M.; Chorev, M.; Enz, A. Pharmacological evaluation of phenyl-carbamates as CNS-selective acetylcholinesterase inhibitors. J. Neural. Transm. 1994, 43, 219-225.
10. Greig, N. H.; Pei, X-F.; Soncrant, T.; Ingram, D.; Brossi, A. Phenserine and ring-C hetero-analogues: drug candidates for the treatment of Alzheimer's disease. Med. Chem. Rev. 1995, 15, 3-31.
11. Greig, N. H.; Utsuki, T.; Ingram, D. K.; Wang, Y.; Pepeu, G.; Scali, C.; Yu, Q. S.; Mamczarz, J.; Holloway, H. W.; Giordano, T.; Chen, D.; Furukawa, K.; Sambamurti, K.; Brossi, A; Lahiri, D. K. Selective butyrylcholinesterase inhibition elevates brain acetylcholine, augments learning and lowers Alzheimer beta-amyloid peptide in rodent. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 17213-17218.
12. Greig, N. H.; Sambamurti, K.; Yu, Q. S.; Brossi, A.; Bruinsma, G.; Lahiri, D. K. An overview of phenserine tartrate, a novel acetylcholinesterase inhibitor for the treatment of Alzheimer's disease. Curr. Alzheimer's Res. 2005, 2, 281-291.
13. Debord, J.; Merle, L.; Bollinger, J. C.; Dantoine, T. Inhibition of butyrylcholinesterase by phenothiazine derivatives. J. Enzyme Inhib. Med. Chem. 2002, 17, 197-202.
14. Darvesh, S.; McDonald, R. S.; Penwell, A.; Conrad, S.; Darvesh, K. V.; Mataija, D.; Gomez, G.; Caines, A.; Walsh, R.; Martin, E. Structure-activity relationships for inhibition of human cholinesterases by alkyl amide phenothiazine derivatives. Bioorg. Med. Chem. 2005, 13, 211-222.
15. Darvesh, S.; McDonald, R. S.; Darvesh, K. V.; Mataija, D.; Conrad, S.; Gomez, G.; Walsh, R.; Martin, E. Selective reversible inhibition of human butyrylcholinesterase by aromatic amide derivatives of phenothiazine. Bioorg. Med. Chem. 2007, 15, 6367-6378.
16. Darvesh, S.; MacKnight, C.; Rockwood, K. Butyrylcholinesterase and cognitive function. Int. Psychogeriatr. 2001, 13, 461-464.
17. Saxena, A.; Redman, A. M.; Jiang, X.; Lockridge, O.; Doctor, B. P. Differences in active site gorge dimensions of cholinesterases revealed by binding of inhibitors to human butyrylcholinesterase. Biochemistry 1997, 36, 14642-14651.
18. Leszczynski, J. F.; Rose, G. D. Loops in Globular Proteins: A Novel Category of Secondary Structure. Science. 1986, 234, 849-855.
19. Velan, B.; Barak, D.; Ariel, N.; Leitner, M.; Bino, T.; Ordentlich, A.; Shafferman, A. Structural modifications of the omega loop in human acetylcholinesterase. FEBS Lett. 1996, 395, 22-28.
20. Dahlbom, R. Basically substituted derivatives of 10-phenothiazine carboxylic acid. Acta Chem. Scand. 1953, 7, 879-884.
21. Clarke, D.; Gilbert, B. C.; Hanson, P.; Kirk, C. M. Heterocyclic free radicals. Part 8. The influence of the structure and the conformation of the side chain on the properties of phenothiazine cation-radicals substituted at nitrogen. J. Chem. Soc., Perkin Trans. 2 1978, 10, 1103-1110.
22. Szabo, W. A.; Chung, R. H.; Tarn, C. C.; Tishler, M. Synthetic applications and mechanism of the pyrolysis of phenothiazine carbamates. J. Org. Chem. 1980, 45, 744-746.
23. Weston, A. W.; DeNet, R. W.; Michaels, R. J., Jr. Antispasmodics. Basic esters and amides of some heterocyclic N-carboxylic acids. J. Am. Chem. Soc. 1953, 75, 4006-4008.
24. Stoss, P.; Satzinger, G. Cyclishe sulfoximides, VI. Transannulare acylivanderungen in cyclischen sulfoximiden. Chem. Ber. 1978, 111, 1453-1463.
25. Darvesh, S.; Kumar, R.; Roberts, S.; Walsh, R.; Martin, E. Butyrylcholinesterase-mediated enhancement of the enzymatic activity of trypsin. Cell. Mol. Neurobiol. 2001, 21, 285-296.
26. Ellman, G. L.; Courtney, K. D.; Andres, V. J.; Featherstone, R. M. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem. Pharmacol. 1961, 7, 88-95.
27. Webb, J. L. Enzyme and metabolic inhibitors, Vol I.: New York: Academic Press, 1963, 535-603..
28. Reiner, E.; Radić, Z. Mechanism of action of cholinesterase inhibitors. In Cholinesterases and Cholinesterase Inhibitors; Giacobini, E., Ed.; Martin Dunitz Ltd.: London, 2000; pp 103-119..
29. Spartan '06; Wavefunction, Inc.: Irvine, CA, 2006.
30. Tetko, I. V.; Tanchuk, V. Y.; Villa, A. E. Prediction of n-octanol/water partition coefficients from PHYSPROP database using artificial neural networks and E-state indices. J. Chem. Inf. Comput. Sci. 2001, 41, 1407-1421.
31. Masson, P.; Legrand, P.; Bartels, C. F.; Froment, M.-T.; Schopfer, L. M.; Lockridge, O. Role of aspartate 70 and tryptophan 82 in binding of succinyldithiocholine to human butyrylcholinesterase. Biochemistry 1997, 36, 2266-2277.
32. HyperChem Release 7.51 for Windows; Hypercube, Inc.: Gainesville, FL, 2002.
33. Nicolet, Y.; Lockridge, O.; Masson, P.; Fontecilla-Camps, J. C.; Nachon, F. Crystal structure of human butyrylcholinesterase and of its complexes with substrate and products. J. Biol. Chem. 2003, 278, 41141-41147.
34. Berman, H. M.; Westbrook, J.; Feng, Z.; Gilliland, G.; Bhat, T. N.; Weissig, H.; Shindyalov, I. N.; Bourne, P. E. The Protein Data Bank. Nucleic Acids Res. 2000, 28, 235, http://www.pdb.org/
35. DeLano, W. L. The PyMOL Molecular Graphics System; DeLano Scientific, San Carlos, CA, 2002; http://www.pymol.org.