Unique push-pull mechanism of dealkylation in soman-inhibited cholinesterases

Biochemistry

Volumn 36, Issue 27, 1997, Pages 8243-8252

  Viragh, Carol ^a   Akhmetshin, Rinat ^a   Kovach, Ildiko M ^a   Broomfield, Clarence ^b  

^a CATHOLIC UNIVERSITY OF AMERICA   (United States)

^b US ARMY MEDICAL RESEARCH INSTITUTE OF CHEMICAL DEFENSE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHOLINESTERASE; SOMAN; TRYPSIN;

ARTICLE; CATALYSIS; CONTROLLED STUDY; DEALKYLATION; DIASTEREOISOMER; EEL; ENZYME ACTIVE SITE; ENZYME ACTIVITY; ENZYME MECHANISM; FETAL CALF SERUM; NONHUMAN; PH; PRIORITY JOURNAL; PROTON TRANSPORT;

ACETYLCHOLINESTERASE; ALKYLATION; ANIMALS; CHOLINESTERASE INHIBITORS; EELS; ELECTROCHEMISTRY; ENZYME ACTIVATION; FETAL BLOOD; HYDROGEN-ION CONCENTRATION; KINETICS; SOLVENTS; SOMAN; SPECTROPHOTOMETRY, ULTRAVIOLET; STEREOISOMERISM;

ANGUILLIFORMES; BOVINAE; ELECTROPHORUS ELECTRICUS;

EID: 0030833798     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi962764q     Document Type: Article

References (55)

1. Adebodun, F., & Jordan, F. (1989) J. Cell. Biochem. 40, 249-260.
2. Beauregard, G., Lum, J., & Roufogalis, B. D. (1981) Biochem. Pharmacol. 30, 2915-2920.
3. Bencsura, A., Enyedy, I., & Kovach, I. M. (1995a) Biochemistry 34, 8989-8999.
4. Bencsura, A., Enyedy, I., Viragh, C, Akhmetshin, R., & Kovach, I. M. (1995b) in Enzymes of The Cholinesterase Family (Quinn, D. M., Balasubramanian, A. S., Doctor, B. P., & Taylor, P., Eds.) pp 155-162, Plenum Press. New York.
5. Bencsura, A., Enyedy, I., & Kovach, I. M. (1996) J. Am. Chem. Soc. 118, 8531-8541.
6. Benschop, H. P., Konings, C. A. G., VanGenderen, J., & DeJong, L. P. A. (1984) Toxicol. Appl. Pharmacol. 72, 61-74.
7. Berman, A., & Decker, M. M. (1986) J. Biol. Chem. 261, 10646-10652.
8. Bourne, Y., Taylor, P., & Marchot, P. (1995) Cell 83, 503-512.
9. Brooks, C. L., III, Karplus, M., & Pettitt, B. M. (1988) in Proteins: A Theoretical Perspective of Dynamics Structure and Thermodynamics (Prigogine, I., & Rice, S. A., Eds.) pp 38-44, Willey & Sons, New York.
10. Bucht, G., & Puu, G. (1984) Biochem. Pharmacol. 33, 3573-3577.
11. Cadogan, J. I. G., Eastlick, D., Hampson, F., Mackie, R. K. (1969) J. Chem. Soc. B 115, 144.
12. Cassidy, C. S., Lin, J., & Frey, P. A. (1997) Biochemistry 36, 4576-4584.
13. Cygler, M., Schrag, J. D., Sussman, J. L., Harel M., Silman, I., Gentry, M. K., & Doctor, B. P. (1993) Protein Sci. 2, 366-382.
14. DeJong, L. P. A., & Benschop, H. P. (1988) in Stereoselectivity of Pesticides (Ariens, E. J., van Rensen, J. J. S., & Welling, W., Eds.) pp 109-149, Elsevier, Amsterdam.
15. DeJong, L. P. A., & Kossen, S. P. (1985) Biochim. Biophys. Acta 830, 345-348.
16. DeJong, L. P. A., & Wolring, G. Z. (1985) Biochem. Pharmacol. 34, 142-145.
17. Dougherty, D. A. (1996) Science 271, 163-168.
18. Ellman, G. L., Courtney, K. D., Andres, V., & Featherstone, R. M. (1961) Biochem. Pharmacol. 7, 88-95.
19. Enyedy, I., Bencsura, A., & Kovach, I. M. (1996) Phosphorus, Sulfur Silicon Relat. Elem. 109-110, 249-252.
20. Fersht, A. (1985) in The Three-Dimensional Structure of Enzymes, W. H. Freeman and Company, New York.
21. Finucane, M. D., Malthouse, J. P. G. (1992) Biochem. J. 286, 889-900.
22. Grunwald, J., Segall, Y., Shirin, E., Waysbort, D., Steinberg, N., Silman, I., & Ashani, Y. (1989) Biochem. Pharmacol. 38, 3157-3168.
23. Hovanec, J. W., Broomfield, C. A., Steinberg, G. M., Lanks, K. W., & Lieske, N. C. (1977) Biochem. Biophys. Acta 483, 312-319.
24. Jencks, W. P. (1969) in Catalysis in Chemistry and Enzymology, McGraw-Hill, New York.
25. Jordan, F., Polgar, L., & Tous, G. (1985) Biochemistry 24, 7711-7717.
26. Keijer, J. H., & Wolring, G. Z. (1969) Biochim. Biophys. Acta 185, 465-468.
27. Keijer, J. H., Worling, G. Z., & DeJong, L. P. A. (1974) Biochim. Biophys. Acta 334, 145-155.
28. Kossiakoff, A. A., & Spencer, S. A. (1981) Biochemistry 20, 6462-6474.
29. Kovach, I. M. (1988a) J. Enzyme Inhib. 2, 199-208.
30. Kovach, I. M. (1988b) THEOCHEM 47, 159-169.
31. Kovach, I. M. (1993) Phosphorus, Sulfur Silicon Relat. EIem. 75, 131-134.
32. Kovach, I. M., & Bennet, A. J. (1990) Phosphorus, Sulfur, Silicon Relat. Elem. 51/52, 51-56.
33. Kresge, A. J., More O'Ferrall, R. A., & Powell, M. F. (1987) in Isotopes in Organic Chemistry, 7 (Buncel, E., & Lee, C. C., Eds.) Chapter 4, p 183, Elsevier, Amsterdam.
34. Lacy, C. I., & Lowe, L. M. (1980) Tetrahedron Lett. 21, 2017.
35. Leatherbarrow, R. J. (1992) in GraFit, Erithacus Software Ltd., Staines, U.K.
36. Lieske, C. N., Hovanec, J. W., Steinberg, G. M., Pikulin, J. N., Lennox, W. J., Ash, A. B., & Blumbergs, P. (1969) J. Agric. Food Chem. 17, 255-258.
37. Michel, H. O., Hackley, B. E. J., Berkowitz, L., List, G., Hackley, E. B., Gillilan, W., & Pankau, M. (1967) Arch. Biochem. Biophys. 121, 29-34.
38. Ordentlich, A., Kronman, C., Barak, D., Stein, D., Ariel, N., Marcus, D., Velan, B., & Shafferman, A. (1993) FEBS Lett. 334, 215-220.
39. Polgar, L. (1987) in Hydrolytic enzymes (Neuberger, A., & Brocklehurst, K. Eds.) pp 159-200, Elsevier Sci. Pub. Co., Amsterdam.
40. Polgar, L. (1990) Mechanisms of Protease Action; CRC Press, Inc., Boca Raton, FL.
41. Porubcan, M. A., Westler, W. M., Ibanez, I. B., & Markley, J. L. (1979) Biochemistry 18, 4108-4116.
42. Puu, G., Artursson, E., & Bücht, G. (1986) Biochem. Phamacol. 35, 1505-1510.
43. Qian, N., & Kovach, I. M. (1993) FEBS Lett. 336, 263-266.
44. Quinn, D. M., Pryor, A. N., Selwood, T., Lee, B. H., Acheson, S. A., & Barlow, P. N. (1991) in Cholinesterases: Structure, Function, Mechanism, Genetics, and Cell Biology (Massoulie, J., Bacou, F., Barnard, E., Chatonnet, A., Doctor, B. P., & Quinn, D. M., Eds.) pp 252-257, American Chemical Society, Washington DC.
45. Robillard, G., & Shulman, R. G. (1974) J. Mol. Biol. 86, 541-558.
46. Saxena, A., Doctor, B. P., Maxwell, D. M., Lenz, D. E., Radic, Z., & Taylor, P. (1993) Biochem. Biophys. Res. Commun. 197, 343-349.
47. Saxena, A., Maxwell, D. M., Quinn, D. M., Radic, Z., Taylor, P., & Doctor, B. P. (1997) Biochem. Pharmacol. (in press).
48. Schoene, K. (1978) Biochim. Biophys. Acta 525, 468-471.
49. Schoene, K., Steinhanses, J., & Wertmann, A. (1980) Biochem. Biophvs. Acta 616, 384-388.
50. Schowen, K. B., & Schowen, R. L. (1982) Methods Enzymol. 87, 551.
51. Segall, Y., Waysbort, D., Barak, D., Ariel, N., Doctor, B. P., Grunwald, J., & Ashani, Y. (1993) Biochemistry 32, 13441-13450.
52. Shafferman, A., Ordentlich, A., Barak, D., Stein, D., Ariel. N., & Velan, B. (1996) Biochem. J. 318, 833-840.
53. Sun, M.-C., Li, F.-Z., & Chou, T.-C. (1986) Biochem. Pharmacol. 35, 347-349.
54. Sussman, J. L., Harel, M., Frolow, F., Oefner, C., Goldman, A., Toker, L., & Silman, I. (1991) Science 253, 872-879.
55. Taylor, P., & Radic, Z. (1994) Annu. Rev. Pharmacol. Toxicol. 34, 281-320.