Potential irreversible ligands for opioid receptors. Cinnamoyl derivatives of β-naltrexamine

Journal of Pharmacy and Pharmacology

Volumn 48, Issue 2, 1996, Pages 192-196

  Derrick, Jan ^a   Lewis, John W ^a   Moynihan, Humphrey A ^a   Broadbear, Jillian ^b   Woods, James H ^b  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

^b UNIVERSITY OF MICHIGAN MEDICAL SCHOOL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BETA FUNALTREXAMINE; DELTA OPIATE RECEPTOR; KAPPA OPIATE RECEPTOR; MU OPIATE RECEPTOR; NALTREXAMINE DERIVATIVE; OPIATE ANTAGONIST; OPIATE RECEPTOR;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ANTINOCICEPTION; COMPETITIVE INHIBITION; CONFERENCE PAPER; CONTROLLED STUDY; DRUG RECEPTOR BINDING; DRUG STRUCTURE; GUINEA PIG; ILEUM; MALE; MOUSE; NONHUMAN;

ANIMALS; DOSE-RESPONSE RELATIONSHIP, DRUG; GUINEA PIGS; ILEUM; MALE; MICE; NALTREXONE; NARCOTIC ANTAGONISTS; PAIN MEASUREMENT; RECEPTORS, OPIOID; VAS DEFERENS;

EID: 0029929556     PISSN: 00223573     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.2042-7158.1996.tb07121.x     Document Type: Article

References (21)

1. Aceto, M. D., Bowman, E. R., May, E. L., Harris, L. S., Woods, J. H., Smith, C. B., Medzihradsky, F., Jacobson, A. E. (1989) Very long acting narcotic antagonists: the 14-β-p-substituted cinnamoylaminomorphinones and their partial μ agonist codeinones. Arzneim. Forsch. 39: 570-575
2. Adams, J. U., Paronis, C. A., Holtzman, S. G. (1990) Assessment of relative intrinsic activity of μ opioid analgesics in-vivo by using β-funaltrexamine. J. Pharmacol. Exp. Ther. 255: 1027-1032
3. Burke, T. F., Woods, J. H., Lewis, J. W., Medzihradsky, F. (1994) Irreversible opioid antagonist effects of clocinnamox on opioid analgesia and μ receptor binding in mice. J. Pharmacol. Exp. Ther. 271: 715-721
4. Caruso, T. P., Takemori, A. E., Larson, D. L., Portoghese, P. S. (1979) Chloroxymorphamine, an opioid receptor site-directed alkylating agent having narcotic agonist activity. Science 204: 316-318
5. Comer, S. D., Burke, T. F., Lewis, J. W., Woods, J. H. (1992) Clocinnamox : A novel, systemically active, irreversible opioid antagonist. J. Pharmacol. Exp. Ther. 262: 1051-1056
6. Hughes, J., Kosterlitz, H. W., Leslie, F. M.(1974). Assessment of the agonist and antagonist activities of narcotic analgesic drugs by means of the mouse vas deferens. Br. J. Pharmacol. 51: 139-140
7. Lewis, J. W., Smith, C. F. C., McCarthy, P. S., Walter, D. S., Kobylecki, R. J., Myers, M., Haynes, A. S., Lewis, C. J., Waltham, K. (1988) New 14-aminomorphinones and codeinones. Problems of Drug Dependence. National Institute on Drug Abuse Research Monograph. 90: 136-143
8. Mjanger, E., Yaksh, T. L. (1991) Characteristics of dose-dependent antagonism by β-funaltrexamine of the antinociceptive effects of intrathecal μ agonists. J. Pharmacol. Exp, Ther. 258: 544-550
9. Paton, W. D. M., Vizi, E. S. (1969) The inhibitory action of noradrenaline and adrenaline on acetylcholine output by guinea-pig ileum longitudinal muscle strip. Br. J. Pharmacol. 35: 10-28
10. Portoghese, P. S., Sayre, L. M., Larson, D. L., Fries, D. S., Takemori, A. E. (1980) A novel opioid receptor site-directed alkylating agent with irreversible narcotic antagonist and reversible agonist activities. J Med. Chem. 23: 233-234
11. Rice, K. C., Jacobson, A. E., Burke Jr. T. R., Bajwa, B. S., Streaty, R. A., Klee, W. A. (1983) Irreversible ligands with high selectivity toward δ or μ, opiate receptors. Science 220: 314-316
12. Ronai, A. Z., Graf, L., Szekely, J. L., Dunai-Kovacs, Z., Bajusz, S. (1974) Differential behaviour of the LPH-(61-91)-peptide in different model systems: Comparison of the opioid activities of LPH-(61-91)-peptide and its fragments. FEBS Letters 74: 182-184
13. Rothman, R. B., Long, J. B., Bykov, V., Jacobson, A. E., Rice, K. C., Holaday, J. W.(1988) β-FNA binds irreversibly to the opioid receptor complex. In vivo and in-vitro evidence. J. Pharmacol. Exp. Ther. 247:, 405-416
14. Sebastian, A., Bidlack, J. M., Jiang, Q., Deecher, D., Teitler, M., Glick, S. D., Archer, S. (1993) 14β-[(p-Nitrocinnamoyl)amino]-morphinones, 14β-[(p-nitrocinnamoylamino]-7,8-dihydromorphinones and their codeinone analogues : synthesis and receptor activity. J. Med. Chem. 36: 3154-3160
15. Stevens, C. W., Yaksh, T. L. (1989) Potency of spinal antinociceptive agents is inversely related to the magnitude of tolerance after continuous infusion. J. Pharmacol. Exp. Ther. 250: 1-8
16. Takemori, A. E., Portoghese, P. S. (1985) Affinity labels for opioid receptors. Ann. Rev. Pharmacol. Toxicol. 25: 193-223
17. Takemori, A. E., Portoghese, P. S. (1987) Evidence for the interaction of morphine with κ and δ opioid receptors to induce analgesia in β-funaltrexamine-treated mice. J. Pharmacol. Exp. Ther. 243: 91-94
18. Ward, S. J., Portoghese, P. S., Takemori, A. E (1982) Pharmacological characterisation in-vivo of the novel opiate β-funaltrexamine. J. Pharmacol. Exp. Ther. 220: 494-498
19. Ward, S. J., Takemori, A. E. (1983) Relative involvement of μ, κ and δ receptor mechanisms in opiate mediated antinociception in mice. J. Pharmacol. Exp. Ther. 224: 525-530
20. Zernig, G., Burke, T., Lewis, J. W., Woods, J. H. (1994) Clocinnamox blocks only μ receptors irreversibly : binding evidence. Int. Narc. Res. Conf. (abst.) July 1994
21. Zimmerman, D. M., Leander, J. D., Reel, J. K., Hynes, M. D. (1987) Use of β-funaltrexamine to determine the μ opioid receptor involvement in the analgesic activity of various opioid ligands. J. Pharmacol. Exp. Ther. 224: 374-378