The pH dependence of dealkylation in soman-inhibited cholinesterases and their mutants: Further evidence for a push-pull mechanism

Biochemistry

Volumn 37, Issue 43, 1998, Pages 15086-15096

  Saxena, Ashima ^a   Viragh, Carol ^b   Frazier, D Scott ^a   Kovach, Ildiko M ^b   Maxwell, Donald M ^c   Lockridge, Oksana ^d   Doctor, B P ^a  

^a WALTER REED ARMY INSTITUTE OF RESEARCH   (United States)

^b CATHOLIC UNIVERSITY OF AMERICA   (United States)

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

^d UNIVERSITY OF NEBRASKA MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2,3 DIMETHYL 1 BUTENE; 2,3 DIMETHYL 2 BUTANOL; 2,3 DIMETHYL 2 BUTENE; CHOLINESTERASE; RECOMBINANT BUTYRYLCHOLINESTERASE; SOMAN; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CELL AGING; CHOLINESTERASE INHIBITION; ENZYME INACTIVATION; HUMAN; HUMAN CELL; PH MEASUREMENT; PRIORITY JOURNAL; PROTON TRANSPORT; STEREOCHEMISTRY; STEREOISOMERISM;

ACETYLCHOLINESTERASE; AMINO ACID SUBSTITUTION; ANIMALS; BUTYRYLCHOLINESTERASE; CHOLINESTERASE INHIBITORS; DEALKYLATION; ENZYME ACTIVATION; GLUTAMIC ACID; HUMANS; HYDROGEN-ION CONCENTRATION; MICE; MUTAGENESIS, SITE-DIRECTED; PHOSPHORYLATION; RECOMBINANT PROTEINS; SOMAN; STEREOISOMERISM; TIME FACTORS; TRYPTOPHAN;

EID: 0032573032     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi980917z     Document Type: Article

References (77)

1. Massoulie, J., Sussman, J. L., Doctor, B. P., Soreq, H., Velan, B., Cygler, M., Rotundo, R., Shafferman, A., Silman, I., and Taylor, P. (1992) in Multidisciplinary Approaches to Cholinesterase Functions (Shafferman, A., and Velan, B., Eds.) pp 285-288, Plenum Press, New York.
2. Kovach, I. M. (1988) J. Enzyme Inhib. 2, 199-208.
3. Qian, N. F., and Kovach, I. M. (1993) 1993 Medical Defense Bioscience Review 3, 1005-1014.
4. Qian, N., and Kovach, I. M. (1993) FEBS Lett. 336, 263-266.
5. Kovach, I. M. (1993) Phosphorus, Sulfur Silicon Relat. Elem. 75, 131-134.
6. Kovach, I. M. (1991) J. Enzyme Inhib. 4, 201-212.
7. Bencsura, A., Enyedy, I., Viragh, C., Akhmetshin, R., and Kovach, I. M. (1995) in Enzymes of The Cholinesterase Family (Quinn, D. M., Balasubramanian, A. S., Doctor, B. P., and Taylor, P., Eds.) pp 155-162, Plenum Press, New York.
8. Kovach, I. M. (1988) THEOCHEM 47, 159-169.
9. Bencsura, A., Enyedy, I., and Kovach, I. M. (1995) Biochemistry 34, 8989-8999.
10. Bencsura, A., Enyedy, I., and Kovach, I. M. (1996) J. Am. Chem. Soc. 118, 8531-8541.
11. Enyedy, I., Bencsura, A., and Kovach, I. M. (1996) Phosphorus, Sulfur Silicon Relat. Elem. 109-110, 249-252.
12. Viragh, C., Akhmetshin, R., Kovach, I. M., and Broomfield, C. (1997) Biochemistry 36, 8243-8252.
13. Kovach, I. M., Akhmetshin, R., Enyedy, I. J., and Viragh, C. (1997) Biochem. J. 324, 995-996.
14. Michel, H. O., Hackley, B. E., Berkowitz, L., List, G., Gillian, W., and Pankau, M. (1967) Arch. Biochem. Biophys. 121, 29-34.
15. Keijer, J. H., and Wolring, G. Z. (1969) Biochim. Biophys. Acta 185, 465-468.
16. Schoene, K., Steinhanses, J., and Wertman, A. (1980) Biochim. Biophys. Acta 616, 384-388.
17. Benschop, H. P., Konings, C. A., VanGenderen, J., and DeJong, L. P. (1984) Toxicol. Appl. Pharmacol. 72, 61-74.
18. Sun, M. C., Li, F. Z., and Chou, T. C. (1986) Biochem. Pharmacol. 35, 347-349.
19. Segall, Y., Waysbort, D., Barak, D., Ariel, N., Doctor, B. P., Grunwald, J., and Ashani, Y. (1993) Biochemistry 32, 13441-13450.
20. Saxena, A., Doctor, B. P., Maxwell, D. M., Lenz, D. E., Radic, Z., and Taylor, P. (1993) Biochem. Biophys. Res. Commun. 197, 343-349.
21. Ordentlich, A., Kronman, C., Barak, D., Stein, D., Ariel, N., Marcus, D., Velan, B., and Shafferman, A. (1993) FEBS Lett. 334, 215-220.
22. Shafferman, A., Ordentlich, A., Barak, D., Stein, D., Ariel, N., and Velan, B. (1996) Biochem. J. 318, 833-840.
23. Shafferman, A., Ordentlich, A., Barak, D., Stein, N., Ariel, N., and Velan, B. (1997) Biochem. J. 324, 996-998.
24. Saxena, A., Maxwell, D. M., Quinn, D. M., Radic, Z., Taylor, P., and Doctor, B. P. (1997) Biochem. Pharmacol. 54, 269-274.
25. Barak, D., Ordentlich, A., Segall, Y., Velan, B., Benschop, H. P., DeJong, L. P., and Shafferman, A. (1997) J. Am. Chem. Soc. 119, 3157-3158.
26. Masson, P., Fortier, P. L., Albaret, C., Froment, M. T., Bartels, C. F., & Lockridge, O. (1997) Biochem. J. 327, 601-607.
27. Kovach, I. M., and Schowen, R. L. (1987) in Peptides and Proteases: Recent Advances (Schowen, R. L., and Barth, A., Eds.) pp 205-205, Pergamon, Oxford, U.K.
28. Kovach, I. M., Larson, M., and Schowen, R. L. (1986) J. Am. Chem. Soc. 108, 5490-5495.
29. Kovach, I. M., Huber-Ashley, H., and Schowen, R. L. (1988) J. Am. Chem. Soc. 110, 590-593.
30. Bennet, A. J., Kovach, I. M., and Schowen, R. L. (1989) Pestic. Biochem. Physiol. 33, 78-82.
31. Bennet, A., Kovach, I. M., and Schowen, R. L. (1988) J. Am. Chem. Soc. 110, 7892-7893.
32. Bennet, A. J., Kovach, I. M., and Bibbs, J. A. (1989) J. Am. Chem. Soc. 111, 6424-6427.
33. Kovach, I. M., and Bennet, A. J. (1990) Phosphorus, Sulfur Silicon Relat. Elem. 51/52, 51-56.
34. Fersht, A. (1985) in The Three-Dimensional Structure of Enzymes, W. H. Freeman and Company, New York.
35. Schowen, R. L. (1978) in Transition States of Biochemical Processes (Gandour, R. D., and Schowen, R. L., Eds.) Plenum, New York.
36. Alvarez, F. J., and Schowen, R. L. (1987) in Isotopes in Organic Chemistry (Buncel, E., and Lee, C. C., Eds.) pp 1-60, Elsevier, Amsterdam, The Netherlands.
37. Broomfield, C. A., Millard, C. B., Lockridge, O., and Caviston, T. L. (1995) in Enzymes of the Cholinesterase Family (Quinn, D. M., Balasubramanian, A. S., Doctor, B. P., and Taylor, P., Eds.) pp 169-175, Plenum Press, New York and London.
38. Lockridge, O., Blong, R. M., Masson, P., Froment, M. T., Millard, C. B., and Broomfield, C. A. (1997) Biochemistry 36, 786-795.
39. Sussman, J. L., Harel, M., Frolow, F., Oefner, C., Goldman, A., Toker, L., and Silman, I. (1991) Science 253, 872-879.
40. Kossiakoff, A. A., and Spencer, S. A. (1981) Biochemistry 20, 6462-6474.
41. Porubcan, M. A., Westler, W. M., Ibanez, I. B., and Markley, J. L. (1979) Biochemistry 18, 4108-4116.
42. Jordan, F., Polgar, L., and Tous, G. (1985) Biochemistry 24, 7711-7717.
43. Frey, P. A., Whitt, S. A., and Tobin, J. B. (1994) Science 264, 1927-1930.
44. Cassidy, C. S., Lin, J., and Frey, P. A. (1997) Biochemistry 36, 4576-4584.
45. Harel, M., Quinn, D. M., Nair, H. K., Silman, I., and Sussman, J. L. (1996) J. Am. Chem. Soc. 118, 2340-2346.
46. Selwood, T., Feaster, S. R., States, M. J., Pryor, A. N., and Quinn, M. D. (1993) J. Am. Chem. Soc. 115, 10477-10482
47. Kresge, A. J., More, O., and Powell, M. F. (1987) in Isotopes in Organic Chemistry (Buncel, E., and Lee, C. C., Eds.) pp 177-273, Elsevier, Amsterdam, The Netherlands.
48. Hosea, N. A., Radic, Z., Tsigelny, I., Berman, H. A., Quinn, D. M., and Taylor, P. (1996) Biochemistry 35, 10995-11004.
49. Millard, C. B., Lockridge, O., and Broomfield, C. A. (1998) Biochemistry 37, 237-247.
50. Benschop, H. P., and De Jong, L. P. (1988) Acc. Chem. Res. 21, 368-374.
51. Ellman, G. L., Courtney, K. D., Andres, V., and Featherstone, R. M. (1961) Biochem. Pharmacol. 7, 88-95.
52. Masson, P., Legrand, P., Bartels, C. F., Froment, M. T., Schopfer, L. M., and Lockridge, O. (1997) Biochemistry 36, 2266-2277.
53. Laidler, K. J. (1987) in Chemical Kinetics, Harper & Row, New York.
54. Leatherbarrow, R. J. (1992) in GraFit Software, Erithacus Software Ltd., Staines, U.K.
55. De Bisschop, H. C. J. V., Michiels, K. W., Vlaminck, L. B., Vansteenkiste, S. O., and Schact, E. H. (1991) Biochem. Pharmacol. 41, 955-959.
56. Keijer, J. H., Wolring, G. Z., and DeJong, L. P. (1974) Biochim. Biophys. Acta 334, 145-155.
57. De Jong, L. P., and Wolring, G. Z. (1984) Biochem. Pharmacol. 33, 1119-1125.
58. DeJong, L. P., and Worling, G. Z. (1985) Biochem. Pharmacol. 34, 142-145.
59. Puu, G., Artursson, E., and Bücht, G. (1986) Biochem. Pharmacol. 35, 1505-1510.
60. DeJong, L. P., and Kossen, S. P. (1985) Biochim. Biophys. Acta 830, 345-348.
61. Bucht, G., and Puu, G. (1984) Biochem. Pharmacol. 33, 3573-3577.
62. Berman, A., and Decker, M. M. (1986) J. Biol. Chem. 261, 10646-10652.
63. Rosenberry, T. L. (1975) Proc. Natl. Acad. Sci. U.S.A. 72, 3834-3838.
64. Rosenberry, T. L. (1975) Croat. Chem. Acta 47, 235-250.
65. Quinn, D. M. (1987) Chem. Rev. 87, 955-975.
66. Taylor, P., and Radic, Z. (1994) Annu. Rev. Pharmacol. Toxicol. 34, 281-320.
67. Masson, P., Clery, C., Guerra, P., Fortier, P. L., Albaret, C., and Lockridge, O. (1998) The Sixth International Meeting on Cholinesterases, March 20-24, 1998, La Jolla CA.
68. Wlodek, S. T., Antosiewicz, J., Gilson, M. K., McCammon, J. A., Clark, T. W., and Scott, L. R. (1995) in Enzymes of the Cholinesterase Family (Quinn, D. M., Balasubramanian, A. S., Doctor, B. P., and Taylor, P., Eds.) pp 97-104, Plenum Press, New York and London.
69. Nair, H. K., Seravalli, J., Arbuckle, T., and Quinn, D. M. (1994) Biochemistry 33, 8566-8576.
70. Wlodek, S. T., Antosiewicz, J., and Briggs, J. M. (1997) J. Am. Chem. Soc. 119, 8159-8165.
71. Quinn, D. M., Pryor, A. N., Selwood, T., Lee, B. H., Acheson, S. A., and Barlow, P. N. (1991) in Cholinesterases: Structure, Function, Mechanism, Genetics, and Cell Biology (Massoulie, J., Bacou, F., Barnard, E., Chatonnet, A., Doctor, B. P., and Quinn, D. M., Eds.) pp 252-257, American Chemical Society, Washington, DC.
72. Saxena, A., Redman, A. M., Jiang, X., Lockridge, O., and Doctor, B. P. (1997) Biochemistry 36, 14642-14651.
73. Enyedy, I. J., and Kovach, I. M. (unpublished results).
74. Harel, M., Sussman, J. L., Krejci, E., Bon, S. Chanal, P., Massoulie, J., and Silman, I. (1992) Proc. Natl. Acad. Sci. U.S.A. 89, 10827-10831.
75. Harel, M., Schalk, I., Ehret-Sabatier, L., Bouet, F., Goeldner, M., Hirth, C., Axelsen, P., Silman, I., and Sussman, J. L. (1993) Proc. Natl. Acad. Sci. U.S.A. 90, 9031-9035.
76. Fleisher, J. H., and Harris, L. W. (1965) Biochem. Pharmacol. 14, 641-650.
77. Coult, D. B., Marsh, D., J., and Read, G. (1965) Biochem. J. 98, 869-873.