Acetylcholinesterase inhibition by diaza- and dioxophosphole compounds: Synthesis and determination of IC50 values

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 19, Issue 5, 2004, Pages 403-407

  Gholivand, Khodayar ^a   Shariatinia, Zahra ^a   Ghadimi, Said ^a   Mojahed, Fresia ^a   Alizadegan, Ahlam Madani ^a   Khajeh, Khosro ^a   Naderi Manesh, Hossein ^a  

^a TARBIAT MODARES UNIVERSITY   (Iran)

Author keywords

Ellman's method; Human acetylcholinesterase; IC50 values; Irreversible inhibitors; Phospholes

Indexed keywords

ACETYLCHOLINESTERASE; ANTIGLAUCOMA AGENT; ANTIPARASITIC AGENT; CHEMICAL WARFARE AGENT; CHOLINESTERASE INHIBITOR; DIAZOPHOSPHOLE; DIOXOPHOSPHOLE; HYDROXYL GROUP; INSECTICIDE; ORGANOPHOSPHORUS COMPOUND; PESTICIDE; PHOSPHOLE DERIVATIVE; SERINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CONTROLLED STUDY; DRUG STRUCTURE; ENZYME INHIBITION; GLAUCOMA; HUMAN; IC 50; PARASITOSIS; PRIORITY JOURNAL; SPECTROPHOTOMETRY; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ACETYLCHOLINESTERASE; BICYCLO COMPOUNDS, HETEROCYCLIC; CHOLINESTERASE INHIBITORS; HUMANS; INHIBITORY CONCENTRATION 50; KINETICS; ORGANOPHOSPHORUS COMPOUNDS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; TIME FACTORS;

EID: 11044222897     PISSN: 14756366     EISSN: None     Source Type: Journal    
DOI: 10.1080/14756360410001722074     Document Type: Article

References (33)

1. Schulze, H., Vorlova, S., Villatte, F., Bachmann, T.T. and Schmid, R.D. (2003) Biosens. Bioelectron. 18, 201-209.
2. Kaplan, D., Ordentlich, A., Barak, D., Ariel, N., Kronman, C., Velan, B. and Shafferman, A. (2001) Biochemistry 40, 7433-7445.
3. Ashani, Y., Bhattacharjee, A.K., Leader, H., Saxena, A. and Doctor, B.P. (2003) Biochem. Pharmacol. 66, 191-202.
4. Gholivand, K.H., Shariatinia, Z., Khajeh, K. and Naderimanesh, H. (2003) J. Enz. Inhib. and Medicinal Chem., In Press.
5. Thompson, C.M., Suarez, A.I. and Rodriguez, O.P. (1996) Chem. Res. Toxicol. 9, 1325-1332.
6. Barak, D., Ordentlich, A., Kaplan, D., Barak, R., Mizrahi, D., Kronman, C., Segall, Y., Velan, B. and Shafferman, A. (2000) Biochemistry 39, 1156-1161.
7. Elhanany, E., Ordentlich, A., Dgany, O., Kaplan, D., Segall, Y., Barak, R., Velan, B. and Shafferman, A. (2001) Chem. Res. Toxicol. 14, 912-918.
8. Mallender, W.D., Szegletes, T. and Rosenberry, T.L. (2000) Biochemistry 39, 7753-7763.
9. Scanlan, T.S. and Reid, R.C. (1995) Chem. Biol. 2 2), 71-75.
10. Lassiter, T.L., Marshall, R.S., Jackson, L.C., Hunter, D.L., Vu, J.T. and Padilla, S. (2003) Toxicology 186, 241-253.
11. Haux, J.E., Lockridge, O. and Casida, J.E. (2002) Chem. Res. Toxicol. 15, 1527-1533.
12. Pang, Y.-P., Kollmeyer, T.M., Hong, F., Lee, J.-C., Hammond, P.I., Haugabouk, S.P. and Brimijoin, S. (2003) Biochem. Biol. 10 491-502.
13. Wong, L., Radic, Z., Bruggemann, R.J.M., Hosea, N., Berman, H.A. and Taylor, P. (2000) Biochemistry 39, 5750-5757.
14. Viragh, C., Kovach, I.M. and Pannell, L. (1999) Biochemistry 38, 9557-9561.
15. Paci, A., Martens, T. and Royer, J. (2001) Bioorgan. Med. Chem. Lett. 11, 1347-1349.
16. Lougestay-Madec, R., Florent, J.-C., Monneret, C., Nematti, F. and Poupan, M.-F. (1998) Anti-Cancer Drug Des. 13, 995.
17. Shulman-Roskes, E.M., Noe, D.A., Gamcsik, M.P., Marlow, A.L., Hilton, J., Hausheer, F.H., Colvin, O.M. and Ludeman, S.M. (1998) J. Med. Chem. 41, 515.
18. Crum-Brown, A. and Frazer, T. (1968) Trans. Roy. Soc. Edinburgh 25(1),151.
19. Balabn, A.T., Chiriac, A. and Motok, I. (1980) Steric Fit in Quantitative Structure-Activity Relations (Springer-Verlag, Berlin Heidelberg).
20. Hansch, C. and Lien, E.J. (1968) Biochem. Pharmacol. 17, 709.
21. Gholivand, K.H., Ghadimi, S., Naderimanesh, H. and Forouzanfar, A. (2001) Mag. Reson. Chem. 39, 684-688.
22. Ellman, G.L., Courtney, K.D., Andres, V. and Featherstone, R.M. (1961) Biochem. Pharmacol. 7, 88-95.
23. Ordentlich, A., Barak, D., Kronman, C., Benschop, H.P., De Jong, L.P.A., Ariel, N., Barak, R., Segall, Y., Velan, B. and Shafferman, A. (1999) Biochemistry 38, 3055-3066.
24. Quistad, G.B., Zhang, N., Sparks, S.E. and Casida, J.E. (2000) Chem. Res. Toxicol. 13, 652-657.
25. Haux, J.E., Quistad, G.B. and Casida, J.E. (2000) Chem. Res. Toxicol. 13, 646-651.
26. Copeland, R.A. (2000) Enzymes, A Practical Introduction to Structure, Mechanism and Data Analysis, 2nd Edn. (Wiley-VCH).
27. Eto, M. (1974) Organophosphorus Pesticides; Organic and Biological Chemistry (CRC Press, Florida).
28. Fukuto, T.R. (1971) "Relationship between the structure of organophosphorus compounds and their activity as acetylcholinesterase inhibitors", Bull. World Health Org. 44, 31-42.
29. Taylor, P. (1985) "Anticholinesterase Agents", In: Gilman, A., Goodman, L.S., Rall, T.W. and Murad, F., eds, Goodman and Gilman's; The Pharmacological Basis of Therapeutics, 7th Edn. (McMilan Press, New York), 110-129.
30. Gholivand, Kh., Tadjarodi, A. and Ng, S.W. (2002) Acta Cryst. E 58, 200-201.
31. Massiah, M.A., Viragh, C., Reddy, P.M., Kovach, I.M., Johnson, J., Rosenberry, T.L. and Mildvan, A.S. (2001) Biochemistry 40, 5682-5690.
32. Cassidy, C.S., Lin, J. and Frey, P.A. (1997) Biochemistry 36, 4576-4584.
33. Viragh, C., Harris, T.K., Reddy, P.M., Massiah, M.A., Mildvan, A.S. and Kovach, I.M. (2000) Biochemistry 39, 16200-16205.