Toxicological and structural features of organophosphorus and organosulfur cannabinoid CB1 receptor ligands

Toxicological Sciences

Volumn 76, Issue 1, 2003, Pages 131-137

  Segall, Yoffi ^a,b   Quistad, Gary B ^a   Sparks, Susan E ^a   Nomura, Daniel K ^a   Casida, John E ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b ISRAEL INSTITUTE FOR BIOLOGICAL RESEARCH   (Israel)

Author keywords

Cannabinoid receptor; CB1; Dodecanesulfonyl fluoride; Fatty acid amide hydrolase; Lysophospholipase; Neuropathy target esterase; O isopropyl dodecylfluorophosphonate

Indexed keywords

4 (1,1 DIMETHYLHEPTYL) 1',2',3',4',5',6' HEXAHYDRO 2,3' DIHYDROXY 6' (3 HYDROXYPROPYL)BIPHENYL; ACETYLCHOLINESTERASE; ALKANE DERIVATIVE; ALKYL GROUP; ANANDAMIDE; CANNABINOID 1 RECEPTOR; CANNABINOID RECEPTOR ANTAGONIST; ESTERASE; LYSOPHOSPHOLIPASE; OCTANE; ORGANOPHOSPHORUS COMPOUND; ORGANOSULFUR DERIVATIVE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BINDING SITE; BRAIN MEMBRANE; CHEMICAL STRUCTURE; CONTROLLED STUDY; COVALENT BOND; DELAYED NEUROTOXICITY; DERIVATIZATION; ENZYME INHIBITION; ENZYME PHOSPHORYLATION; IC 50; IN VITRO STUDY; IN VIVO STUDY; MALE; MOUSE; NEUROPATHY; NONHUMAN; PATHOPHYSIOLOGY; RECEPTOR BINDING; RECUMBENCY; TOXICITY TESTING;

ANIMALS; BINDING, COMPETITIVE; BRAIN; CELL MEMBRANE; INJECTIONS, INTRAPERITONEAL; LIGANDS; MALE; MICE; MOTOR ACTIVITY; ORGANOPHOSPHORUS COMPOUNDS; RECEPTOR, CANNABINOID, CB1; STRUCTURE-ACTIVITY RELATIONSHIP; SULFUR COMPOUNDS;

ANIMALIA;

EID: 0242268497     PISSN: 10966080     EISSN: None     Source Type: Journal    
DOI: 10.1093/toxsci/kfg216     Document Type: Article

References (31)

1. Adams, I. B., Ryan, W., Singer, M., Thomas, B. F., Compton, D. R., Razdan, R. K., and Martin, B. R. (1995). Evaluation of cannabinoid receptor binding and in vivo activities of anandamide analogs. J. Pharmacol. Exp. Ther. 273, 1172-1181.
2. Aldridge, W. N., and Reiner, E. (1972). Enzyme Inhibitors as Substrates. Interactions of Esterases with Esters of Organophosphorus and Carbamate Acids. North-Holland Publ. Co., Amsterdam.
3. Bracey, M. H., Hanson, M. A., Masuda, K. R., Stevens, R. C., and Cravatt, B. F. (2002). Structural adaptations in a membrane enzyme that terminates endocannabinoid signaling. Science 298, 1793-1796.
4. Compton, D. R., and Martin, B. R. (1997). The effect of the enzyme inhibitor phenylmethylsulfonyl fluoride on the pharmacological effect of anandamide in the mouse model of cannabimimetic activity. J. Pharmacol. Exp. Ther. 283, 1138-1143.
5. Cravatt, B. F., Demarest, K., Patricelli, M. P., Bracey, M. H., Giang, D. K., Martin, B. R., and Lichtman, A. H. (2001). Supersensitivity to anandamide and enhanced endogenous cannabinoid signaling in mice lacking fatty acid amide hydrolase. Proc. Natl. Acad. Sci. U.S.A. 98, 9371-9376.
6. Deutsch, D. G., Lin, S., Hill, W. A. G., Morse, K. L., Salehani, D., Arreaza, G., Omeir, R. L., and Makriyannis, A. (1997a). Fatty acid sulfonyl fluorides inhibit anandamide metabolism and bind to the cannabinoid receptor. Biochem. Biophys. Res. Commun. 231, 217-221.
7. Deutsch, D. G., Omeir, R., Arreaza, G., Salehani, D., Prestwich, G. D., Huang, Z., and Howlett, A. (1997b). Methyl arachidonyl fluorophosphonate: A potent irreversible inhibitor of anandamide amidase. Biochem. Pharmacol. 53, 255-260.
8. Devane, W. A., Hanuš, L., Breuer, A., Pertwee, R. G., Stevenson, L. A., Griffin, G., Gibson, D., Mandelbaum, A., Etinger, A., and Mechoulam, R. (1992). Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science 258, 1946-1949.
9. Felder, C. C., Briley, E. M., Axelrod, J., Simpson, J. T., Mackie, K., and Devane, W. A. (1993). Anandamide, an endogenous cannabimimetic eicosanoid, binds to the cloned human cannabinoid receptor and stimulates receptor-mediated signal transduction. Proc. Natl. Acad. Sci. U.S.A. 90, 7656-7660.
10. Gifford, A. N., Bruneus, M., Lin, S., Goutopoulos, A., Makriyannis, A., Volkow, N. D., and Gatley, S. J. (1999). Potentiation of the action of anandamide on hippocampal slices by the fatty acid amide hydrolase inhibitor, palmitylsulfonyl fluoride (AM 374). Eur. J. Pharmacol. 383, 9-14.
11. Glynn, P. (2000). Neural development and neurodegeneration: Two faces of neuropathy target esterase. Progr. Neurobiol. 61, 61-74.
12. Hillard, C. J., and Campbell, W. B. (1997). Biochemistry and pharmacology of arachidonylethanolamide, a putative endogenous cannabinoid. J. Lipid Res. 38, 2383-2398.
13. Hillard, C. J., Manna, S., Greenberg, M. J., Dicamelli, R., Ross, R. A., Stevenson, L. A., Murphy, V., Pertwee, R. G., and Campbell, W. B. (1999). Synthesis and characterization of potent and selective agonists of the neuronal cannabinoid receptor (CB1). J. Pharmacol. Exp. Ther. 289, 1427-1433.
14. Johnson, M. K., and Glynn, P. (2001). Neuropathy target esterase. In Handbook of Pesticide Toxicology. Vol. 2. Agents. (R. I. Krieger, Ed.), pp. 953-965. Academic Press, San Diego.
15. Khanolkar, A. D., and Makriyannis, A. (1999). Structure-activity relationships of anandamide, an endogenous cannabinoid ligand. Life Sci. 65, 607-616.
16. Khanolkar, A. D., Palmer, S. L., and Makriyannis, A. (2000). Molecular probes for the cannabinoid receptors. Chem. Phys. Lipids 108, 37-52.
17. Lotti, M., Moretto, A., Capodicasa, E., Bertolazzi, M., Peraica, M., and Scapellato, M. L. (1993). Interactions between neuropathy target esterase and its inhibitors and the development of polyneuropathy. Toxicol. Appl. Pharmacol. 122, 165-171.
18. Lush, M. J., Li, Y., Read, D. J., Willis, A. C., and Glynn, P. (1998). Neuropathy target esterase and a homologous Drosophila neurodegeneration-associated mutant protein contain a novel domain conserved from bacteria to man. Biochem. J. 332, 1-4.
19. Martin, B. R., Beletskaya, I., Patrick, G., Jefferson, R., Winckler, R., Deutsch, D. G., Di Marzo, V., Dasse, O., Mahadevan, A., and Razdan, R. K. (2000). Cannabinoid properties of methylfluorophosphonate analogs. J. Pharmacol. Exp. Ther. 294, 1209-1218.
20. Quistad, G. B., Barlow, C., Winrow, C. J., Sparks, S. E., and Casida, J. E. (2003). Evidence that mouse brain neuropathy target esterase is a lysophospholipase. Proc. Natl. Acad. Sci. U.S.A. 100, 7983-7987.
21. Quistad, G. B., Nomura, D. K., Sparks, S. E., Segall, Y., and Casida, J. E. (2002a). Cannabinoid CB1 receptor as a target for chlorpyrifos oxon and other organophosphorus pesticides. Toxicol. Lett. 135, 89-93.
22. Quistad, G. B., Sparks, S. E., and Casida, J. E. (2001). Fatty acid amide hydrolase inhibition by neurotoxic organophosphorus pesticides. Toxicol. Appl. Pharmacol. 173, 48-55.
23. Quistad, G. B., Sparks, S. E., Segall, Y., Nomura, D. K., and Casida, J. E. (2002b). Selective inhibitors of fatty acid amide hydrolase relative to neuropathy target esterase and acetylcholinesterase: Toxicological implications. Toxicol. Appl. Pharmacol. 179, 57-63.
24. Ross, R. A., Brockie, H. C., Fernando, S. R., Saha, B., Razdan, R. K., and Pertwee, R. G. (1998). Comparison of cannabinoid binding sites in guinea-pig forebrain and small intestine. Br. J. Pharmacol. 125, 1345-1351.
25. 3H]dodecanesulfonyl fluoride. Syn. Comm. 33, 2151-2159.
26. Segall, Y., Quistad, G. B., Nomura, D. K., and Casida, J. E. (2003b). Arachidonylsulfonyl derivatives as cannabionoid CB1 receptor and fatty acid amide hydrolase inhibitors. Bioorg. Med. Chem. Lett. 13, 3301-3303.
27. Tomizawa, M., Cowan, A., and Casida, J. E. (2001). Analgesic and toxic effects of neonicotinoid insecticides in mice. Toxicol. Appl. Pharmacol. 177, 77-83.
28. Winrow, C. J., Hemming, M. L., Allen, D. M., Quistad, G. B., Casida, J. E., and Barlow, C. (2003). Loss of neuropathy target esterase in mice links organophosphate exposure to hyperactivity. Nat. Genet. 33, 477-485.
29. Wu, S.-Y., and Casida, J. E. (1992). Neuropathy target esterase inhibitors: 2-alkyl-, 2-alkoxy-, and 2-(aryloxy)-4H-1,3,2-benzodioxaphosphorin 2-oxides. Chem. Res. Toxicol. 5, 680-684.
30. Wu, S.-Y., and Casida, J. E. (1995). Ethyl octylphosphonofluoridate and analogs: Optimized inhibitors of neuropathy target esterase. Chem. Res. Toxicol. 8, 1070-1075.
31. Wu, S.-Y., and Casida, J. E. (1996). Subacute neurotoxicity induced in mice by potent organophosphorus neuropathy target esterase inhibitors. Toxicol. Appl. Pharmacol. 139, 195-202.