Change in the mode of inhibition of acetylcholinesterase by (4- nitrophenyl)sulfonoxyl derivatives of conformationally constrained choline analogues

Chemical Research in Toxicology

Volumn 11, Issue 1, 1998, Pages 19-25

  Savle, Prashant S ^a   Medhekar, Rohit A ^b   Kelley, Ella L ^b,c   May, Jerome G ^d   Watkins, Steven F ^d   Fronczek, Frank R ^d   Quinn, Daniel M ^b   Gandour, Richard D ^a  

^a VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

^b E11 SSH   (United States)

^c SOUTHERN UNIVERSITY   (United States)

^d LOUISIANA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLCHOLINESTERASE; CHOLINESTERASE INHIBITOR; MORPHOLINE DERIVATIVE;

ARTICLE; CHIRALITY; COMPETITIVE INHIBITION; ENANTIOMER; ENZYME INHIBITION; HYDROLYSIS;

ACETYLCHOLINESTERASE; ANIMALS; CHOLINE; CHOLINESTERASE INHIBITORS; ELECTROPHORUS; MOLECULAR CONFORMATION; NITROBENZENES; SULFONES;

GARCIA;

EID: 0031910287     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx970019o     Document Type: Article

References (22)

1. Rosenberry, T. L. (1975) Acetylcholinesterase. Adv. Enzymol. Relat. Areas Mol Biol. 43, 103-218.
2. Quinn, D. M. (1987) Acetylcholinesterase. Enzyme structure, reaction dynamics and virtual transition states. Chem. Rev. 87, 955-979.
3. Stedman, E. (1929) Studies on the relationship between chemical constitution and physiological action. Part II. The miotic activity of urethanes derived from the isorneric hydroxybenzyldimethylamines. Biochem. J. 23, 17-24.
4. Pang, Y.-P-, Quiram, P., Jelacic, T., Hong, F., and Brimijoin, S. (1996) Highly potent, selective, and low-cost bis-tetrahydroaminacrine inhibitors of acetylcholinesterase: step toward novel drugs for Alzheimer's disease. J. Biol. Chem. 271, 23646-23649.
5. Sussman, J. L., Harel, M., Frowlow, F., Oefner, C., Goldman, A., Toker, L., and Silman, I. (1991) Atomic structure of acetylcholinesterase from Torpedo californica: a prototypic acetylcholine binding protein. Science Washington, D.C.) 253, 872-879.
6. Haworth, R. D., Lamberton, A. H., and Woodcock, D. (1947) Investigations on the influence of chemical constitution upon toxicity. Part I. Compounds related to Doryl. J. Chem. Soc. 176-182.
7. Harel, M., Schalk, I., Ehret-Sabatier, L., Bouet, F., Goeldner, M., Hirth, C., Axelsen, P. H., Silman, I., and Sussman, J. L. (1993) Quaternary ligand binding to aromatic residues in the activesite gorge of acetylcholinesterase. Proc. Natl. Acad. Sci. U.S.A. 90, 9031-9035.
8. Lee, B. H., Stelly, T. C., Colucci, W. J., Garcia, J. G., Gandour, R. D., and Quinn, D. M. (1992) Inhibition of acetylcholinesterase by hemicholiniums, conformationally constrained choline analogues. Evaluation of aryl and alkyl substituents. Comparison with choline and (3-hydroxyphenyl)trimethylammonium. Chem. Res. Toxicol 5, 411-418.
9. Sørensen, P. E., McClelland, R. A., and Gandour, R. D. (1991) Intramolecular hemiacetals. The acid-base-catalyzed ring-chain interconversion of 2-sabstituted 2-hydroxy-4,4-dimethylmorpholinium cations in aqueous solution. Acta Chem. Scctnd. 45, 558-566.
10. Ya-nagisawa, H., and Kanazaki, T, (1993) Facile synthesis of optically active 4-tert-butoxycarbonyl-2-hydroxymethyhnorpholine. Heterocycles 35, 105-109.
11. Morie, T., Kato, S., Harada, H., Yoshida, N., and Matsumoto, J. (1994) Synthesis and biological activities of the optical isomers of (±)-4-amino-5-chloro-2-ethoxy-AT-[[4-(4-fluorobcnzyl)-2-morpholinyl] methyl]benzamide (Mosapride). Chem. Pharm. Bull. 42, 877-882.
12. Licandro, E., Maiorana, S., Papagni, A., Pryce, M., Gerosa, A. Z., and Riva, S. (1995) Asymmetric synthesis of (-)-(27?,6/?}-2,6-diniethylmorpholine. Tetrahedron: Asymmetry 6, 1891-1894.
13. Thorey, C., Wilken, J., Hénin, F., Martens, J., Mehler, T., and Muzart, J. (1995) Diastereoselective synthesis of vinylmorpholines by palladium-catalyzed tandem allylic substitutions using enantiopure amino alcohols as bifunctional nucleophiles. Tetrahedron Lett. 36, 5527-5530.
14. Sun, G., Savle, P. S., Gandour, R. D., Nie a Bhaírd, N., Ramsay, R. R., and Fronczek, F. R. (1995) Syntheses, structures, and enzymatic evaluations of conformationally constrained, analogue inhibitors of carnitine acetyltransferase: (2R,6R)-, (2S,6S)-, (2R,6S)-, and (2S,6R)-6-carboxylatomethyl-hydroxymethyl-trimethylmorpholinium. J. Org. Chem. 60, 6688-6695.
15. B antagonists. Bioorg. Med. Chem. Lett. 6, 1529-1534.
16. Wipf, P., and Xu, W. (1993) Organozirconocenes in organic synthesis: tandem epoxide rearrangement-carbonyl addition. J. Org. Chem. 58, 825-826.
17. Gajewski, J. J., and Gilbert, K. E. (1992) PCMODEL Molecular Modeling Package, version 4.0, Serena Software, P.O. Box 3076, Bloomington, IN 47402.
18. SYBYL Molecular Modeling Package, version 6.1 (1994) Tripos, Inc., St. Louis, MO 63144.
19. Ellman, G. L., Coutney, K. D., Andres, V., Jr., and Featherstone, R, M. (1961) A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem. Pharmacol. 7, 88-95.
20. Lee, J. H., Cho, Y. H., Lee, H. K., and Cho, S. H. (1995) A facile one-pot transformation of carboxylic acids to amides. Synth. Commun. 25, 2877-2881.
21. Sussman, J. L., Harel, M., and Silman, I. (1993) Three-dimensional structure of acetylcholinesterase and of its complexes with anticholinesterase drugs. Chem. Biol. Interact. 87, 187-197.
22. Kitz, R., and Wilson, I. B. (1962) Esters of methanesulfonic acid as irreversible inhibitors of acetylcholinesterase. J. Biol. Chem. 237, 3245-3249.