Oxime-assisted acetylcholinesterase catalytic scavengers of organophosphates that resist aging

Journal of Biological Chemistry

Volumn 286, Issue 34, 2011, Pages 29718-29724

  Cochran, Rory ^a   Kalisiak, Jarosław ^b   Küçükkilinç, Tuba ^a   Radić, Zoran ^a   Garcia, Edzna ^a   Zhang, Limin ^a   Ho, Kwok Yiu ^a   Amitai, Gabriel ^c   Kovarik, Zrinka ^d   Fokin, Valery V ^b   Sharpless, K Barry ^b   Taylor, Palmer ^a  

^a UNIVERSITY OF CALIFORNIA SAN DIEGO   (United States)

^b SCRIPPS RESEARCH INSTITUTE   (United States)

^c ISRAEL INSTITUTE FOR BIOLOGICAL RESEARCH   (Israel)

^d INSTITUTE FOR MEDICAL RESEARCH AND OCCUPATIONAL HEALTH   (Croatia)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLCHOLINESTERASE; ACTIVE CENTER; AGING RESISTANCE; BUTYRYLCHOLINESTERASE; OBIDOXIME; PYRIDINIUM; WILD TYPES;

SCAVENGING;

1 (4 CARBAMOYLPYRIDINIO) 1' (2 HYDROXYIMINOMETHYLPYRIDINIO)DIMETHYL ETHER; ACETYLCHOLINESTERASE; CYCLOSARIN; METHYLPHOSPHONOTHIOIC ACID S (2 DIISOPROPYLAMINOETHYL) O ETHYL ESTER; ORGANOPHOSPHATE; OXIME; PARAOXON; PRALIDOXIME; SARIN; SOMAN;

AGING; ARTICLE; CONTROLLED STUDY; ENZYME ACTIVE SITE; ENZYME ACTIVITY; ENZYME REACTIVATION; ENZYME STRUCTURE; ENZYME SUBSTRATE; GENE MUTATION; HUMAN; HUMAN CELL; MOLECULAR MODEL; PRIORITY JOURNAL; WILD TYPE;

ACETYLCHOLINESTERASE; AGING; CATALYTIC DOMAIN; HUMANS; MUTATION, MISSENSE; OXIMES; PHOSPHORIC ACID ESTERS; PYRIDINIUM COMPOUNDS;

EID: 80051922044     PISSN: 00219258     EISSN: 1083351X     Source Type: Journal    
DOI: 10.1074/jbc.M111.264739     Document Type: Article

References (31)

1. Taylor, P. (2011) in Goodman & Gilman's The Pharmacological Basis of Therapeutics (Brunton L. L., Chabner, B., and Knollman, B., eds) 13th Ed., pp. 239-254, McGraw-Hill Inc., New York
2. Croddy, E., and Wirtz, J. J. (eds) (2005) Weapons of Mass Destruction: An Encyclopedia of Worldwide Policy, Technology, and History, pp. 1-449, ABC-CLIO, Greenwood, Santa Barbara, CA
3. McDonough, J. H., and Romano, J. A., Jr. (2007) Chemical Warfare Agents: Chemistry, Pharmacology, Toxicology, and Therapeutics (Romano, J. A., Lukey, B. J., and Salem, H., eds) 2nd Ed., pp. 71-96, CRC Press, Inc., Boca Raton, FL
4. Cerasoli, D. M., Griffiths, E. M., Doctor, B. P., Saxena, A., Fedorko, J. M., Greig, N. H., Yu, Q. S., Huang, Y., Wilgus, H., Karatzas, C. N., Koplovitz, I., and Lenz, D. E. (2005) Chem. Biol. Interact. 157-158, 363-365
5. Raveh, L., Grauer, E., Grunwald, J., Cohen, E., and Ashani, Y. (1997) Toxicol. Appl. Pharmacol. 145, 43-53
6. Raveh, L., Grunwald, J., Marcus, D., Papier, Y., Cohen, E., and Ashani, Y. (1993) Biochem. Pharmacol. 45, 2465-2474
7. Wolfe, A. D., Blick, D. W., Murphy, M. R., Miller, S. A., Gentry, M. K., Hartgraves, S. L., and Doctor, B. P. (1992) Toxicol. Appl. Pharmacol. 117, 189-193
8. Kovarik, Z., Radić, Z., Berman, H. A., Simeon-Rudolf, V., Reiner, E., and Taylor, P. (2004) Biochemistry 43, 3222-3229
9. Kovarik, Z., Radić, Z., Berman, H. A., and Taylor, P. (2007) Toxicology 233, 79-84
10. Saxena, A., Maxwell, D. M., Quinn, D. M., Radić, Z., Taylor, P., and Doctor, B. P. (1997) Biochem. Pharmacol. 54, 269-274
11. Taylor, P., Kovarik, Z., Reiner, E., and Radić, Z. (2007) Toxicology 233, 70-78
12. Fleisher, J. H., and Harris, L. W. (1965) Biochem. Pharmacol. 14, 641-650
13. Saxena, A., Doctor, B. P., Maxwell, D. M., Lenz, D. E., Radic, Z., and Taylor, P. (1993) Biochem. Biophys. Res. Commun. 197, 343-349
14. Shafferman, A., Ordentlich, A., Barak, D., Stein, D., Ariel, N., and Velan, B. (1996) Biochem. J. 318, 833-840
15. Mazor, O., Cohen, O., Kronman, C., Raveh, L., Stein, D., Ordentlich, A., and Shafferman, A. (2008) Mol. Pharmacol. 74, 755-763
16. Amitai, G., Adani, R., Yacov, G., Yishay, S., Teitlboim, S., Tveria, L., Limanovich, O., Kushnir, M., and Meshulam, H. (2007) Toxicology 233, 187-198
17. Ellman, G. L., Courtney, K. D., Andres, V., Jr., and Featherstone, R. M. (1961) Biochem. Pharmacol. 7, 88-95
18. Ho, S. N., Hunt, H. D., Horton, R. M., Pullen, J. K., and Pease, L. R. (1989) Gene 77, 51-59
19. Kovarik, Z., Radić, Z., Berman, H. A., Simeon-Rudolf, V., Reiner, E., and Taylor, P. (2003) Biochem. J. 373, 33-40
20. Radić, Z., Gibney, G., Kawamoto, S., MacPhee-Quigley, K., Bongiorno, C., and Taylor, P. (1992) Biochemistry 31, 9760-9767
21. Ashani, Y., Radić, Z., Tsigelny, I., Vellom, D. C., Pickering, N. A., Quinn, D. M., Doctor, B. P., and Taylor, P. (1995) J. Biol. Chem. 270, 6370-6380
22. Froede, H. C., and Wilson, I. B. (1971) in The Enzymes (Boyer, P. D., ed) 3rd Ed., Vol. 5, p. 87, Academic Press, New York
23. Ordentlich, A., Barak, D., Kronman, C., Flashner, Y., Leitner, M., Segall, Y., Ariel, N., Cohen, S., Velan, B., and Shafferman, A. (1993) J. Biol. Chem. 268, 17083-17095
24. Valle, A. M., Radić, Z., Rana, B. K., Mahboubi, V., Wessel, J., Shih, P. A., Rao, F., O'Connor, D. T., and Taylor, P. (2011) J. Pharm. Exp. Ther. 338, 125-133
25. Küçükkilinç, T., Cochran, R., Kalisiak, J., Garcia, E., Valle, A., Amitai, G., Radiæ, Z., and Taylor, P. (2010) Chem. Biol. Interact. 187, 238-240
26. Ordentlich, A., Barak, D., Kronman, C., Benschop, H. P., De Jong, L. P., Ariel, N., Barak, R., Segall, Y., Velan, B., and Shafferman, A. (1999) Biochemistry 38, 3055-3066
27. Kolb, H. C., Finn, M. G., and Sharpless, K. B. (2001) Angew. Chem. Int. Ed. Engl. 40, 2004-2021
28. Taylor, P., Reiner, E., Kovarik, Z., and Radiæ, Z. (2007) Arh Hig Rada Toksikol. 58, 339-345
29. Aldridge, W. N., and Reiner, E. (1972) Enzyme Inhibitors as Substrates. Interactions of Esterases with Esters of Organophosphorous and Carbamic Acids, pp. 1-328, North-Holland Publishing Co., Amsterdam
30. Huang, Y. J., Lundy, P. M., Lazaris, A., Huang, Y., Baldassarre, H., Wang, B., Turcotte, C., Côté, M., Bellemare, A., Bilodeau, A. S., Brouillard, S., Touati, M., Herskovits, P., Bégin, I., Neveu, N., Brochu, E., Pierson, J., Hockley, D. K., Cerasoli, D. M., Lenz, D. E., Wilgus, H., Karatzas, C. N., and Langermann, S. (2008) BMC Biotechnol. 8, 50
31. Rosenberg, Y. J., Saxena, A., Sun, W., Jiang, X., Chilukuri, N., Luo, C., Doctor, B. P., and Lee, K. D. (2010) Chem. Biol. Interact. 187, 279-286