Characterization of 6α- and 6β- N -heterocyclic substituted naltrexamine derivatives as novel leads to development of mu opioid receptor selective antagonists

ACS Chemical Neuroscience

Volumn 2, Issue 7, 2011, Pages 346-351

  Yuan, Yunyun ^a   Li, Guo ^a   He, Hengjun ^a   Stevens, David L ^a   Kozak, Patrick ^a   Scoggins, Krista L ^a   Mitra, Pallabi ^a   Gerk, Phillip M ^a   Selley, Dana E ^a   Dewey, William L ^a   Zhang, Yan ^a  

^a VIRGINIA COMMONWEALTH UNIVERSITY   (United States)

Author keywords

Mu opioid receptor; NAP; NAQ; selective antagonist

Indexed keywords

BETA FUNALTREXAMINE; CLOCINNAMOX; CYPRODIME; DEXTRO PHENYLALANYLCYSTEINYLTYROSYL DEXTRO TRYPTOPHYLARGINYLTHREONYLPENICILLAMINYLTHREONINAMIDE 2,7 DISULFIDE; ELACRIDAR; HETEROCYCLIC COMPOUND; MU OPIATE RECEPTOR; MU OPIATE RECEPTOR ANTAGONIST; NALOXONE; NALTREXAMINE DERIVATIVE; NALTREXOL; NALTREXONE;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; DRUG SELECTIVITY; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; MALE; MOLECULAR MODEL; MOUSE; NONHUMAN; PRIORITY JOURNAL; RAT;

ANIMALS; CACO-2 CELLS; CHO CELLS; CRICETINAE; CRICETULUS; DRUG IMPLANTS; GUANOSINE 5'-O-(3-THIOTRIPHOSPHATE); HETEROCYCLIC COMPOUNDS; HUMANS; MALE; MEMBRANES; MICE; MORPHINE; MORPHINE DEPENDENCE; NALTREXONE; NARCOTIC ANTAGONISTS; NARCOTICS; RATS; RECEPTORS, OPIOID, MU; SUBSTANCE WITHDRAWAL SYNDROME; THALAMUS;

EID: 79960720063     PISSN: None     EISSN: 19487193     Source Type: Journal    
DOI: 10.1021/cn2000348     Document Type: Article

References (24)

1. Zimmerman, D. M. and Leander, J. D. (1990) Selective opioid receptor agonists and antagonists: research tools and potential therapeutic agents J. Med. Chem. 33, 895-902 (Pubitemid 20085889)
2. Schmidhammer, H. (1998) Opioid Receptor Antagonists Prog. Med. Chem. 35, 83-132
3. Eguchi, M. (2004) Recent advances in selective opioid receptor agonists and antagonists Med. Res. Rev. 24, 182-212 (Pubitemid 38230679)
4. Gaveriaux-Ruff, C. and Kieffer, B. L. (2002) Opioid receptor genes inactivated in mice: the highlights Neuropeptides 36, 62-71
5. Martin, M., Matifas, A., Maldonado, R., and Kieffer, B. L. (2003) Acute antinociceptive responses in single and combinatorial opioid receptor knockout mice: distinct mu, delta and kappa tones Eur. J. Neurosci. 17, 701-708 (Pubitemid 36315240)
6. Contet, C., Kieffer, B. L., and Befort, K. (2004) Mu opioid receptor: a gateway to drug addiction Curr. Opin. Neurobiol. 14, 370-378 (Pubitemid 38759868)
7. Schmidhammer, H., Burkard, W. P., Eggstin-Aeppli, L., and Smith, C. F. C. (1989) Synthesis and biological evaluation of 14-alkoxymorphinans. 2. (-)-N-(cyclopropymethyl)-4, 14-dimethoxymorphinana-6-one, a selective mu opioid receptor antagonist J. Med. Chem. 32, 418-421 (Pubitemid 19061887)
8. Marki, A., Monory, K., Otvos, F., Toth, G., Krassnig, R., Schmidhammer, H., Traynor, J. R., Roques, B. P., Maldonado, R., and Borsodi, A. (1999) Mu-opioid receptor specific antagonist cyprodime: characterization by in vitro radioligand and [35S]GTPgammaS binding assays Eur. J. Pharmacol. 383, 209-214
9. Lewis, J. W., Smith, C. F. C., McCarthy, P. S., Kobylecki, R. J., Myers, M., Haynes, A. S., Lewis, C. J., and Waltham, K. (1988) New 14-aminomorphinones and codeinones NIDA Res. Monogr. 90, 136-143 (Pubitemid 20091060)
10. Portoghese, P. S. and Takemori, A. E. (1986) Affinity labels as probes for opioid receptor types and subtypes NIDA Res. Monogr. 69, 157-168 (Pubitemid 17201094)
11. Burke, T. F., Woods, J. H., Lewis, J. W., and Medzihradsky, F. (1994) Irreversible opioid antagonist effects of clocinnamox on opioid analgesia and mu receptor binding in mice J. Pharmcol. Exp. Ther. 271, 715-721 (Pubitemid 24377755)
12. Pelton, J. T., Kazmierski, W., Gulya, K., Yamamura, H. I., and Hruby, V. J. (1986) Design and synthesis of conformationally constrained somatostatin analogues with high potency and specificity for mu opioid receptors J. Med. Chem. 29, 2370-2375 (Pubitemid 17182319)
13. Gulya, K, Pelton, J. T., Hruby, V. J., and Yamamura, H. I. (1986) Cyclic somatostatin octapeptide analogues with high affinity and selectivity toward mu opioid receptors Life Sci. 38, 2221-2229 (Pubitemid 16071273)
14. Hawkins, K. N., Knapp, R. J., Lui, G. K., Gulya, K., Kazmierski, W., Wan, Y. P., Pelton, J. T., Hruby, V. J., and Yamamura, H. I. (1989) [3H]-[H-D-Phe-Cys-Tyr-D-Trp-Orn-Thr-Pen-Thr-NH2] ([3H]CTOP), a potent and highly selective peptide for mu opioid receptors in rat brain J. Pharmacol. Exp. Ther. 248, 73-80 (Pubitemid 19063472)
15. Kramer, T. H., Shook, J. E., Kazmierski, W., Ayres, E. A., Wire, W. S., Hruby, V. J., and Burks, T. F. (1989) Novel peptidic mu opioid antagonists: pharmacologic characterization in vitro and in vivo J. Pharmacol. Exp. Ther. 249, 544-551 (Pubitemid 19144847)
16. Hruby, V. J., Toth, G., Gehrig, C. A., Kao, L. F., Knapp, R., Lui, G. K., Yamamura, H. I., Kramer, T. H., Davis, P., and Burks, T. F. (1991) Topographically designed analogues of [D-Pen,D-Pen5]enkephalin J. Med. Chem. 34, 1823-1830
17. Mulder, A. H., Wardeh, G., Hogenboom, F., Kazmierski, W., Hruby, V. J., and Schoffelmeer, A. N. (1991) Cyclic somatostatin analogues as potent antagonists at mu-, but not delta- and kappa-opioid receptors mediating presynaptic inhibition of neurotransmitter release in the brain Eur. J. Pharmacol. 205, 1-6
18. Abbruscato, T. J., Thomas, S. A., Hruby, V. J., and Davis, T. P. (1997) Blood-brain barrier permeability and bioavailability of a highly potent and mu-selective opioid receptor antagonist, CTAP: comparison with morphine J. Pharmacol. Exp. Ther. 280, 402-409 (Pubitemid 27171427)
19. Bonner, G. G., Davis, P., Stropova, D., Edsall, S., Yamamura, H. I., Porreca, F., and Hruby, V. J. (2000) Opiate aromatic pharmacophore structure-activity relationships in CTAP analogues determined by topographical bias, two-dimensional NMR, and biological activity assays J. Med. Chem. 43, 569-580 (Pubitemid 30127152)
20. Li, G., Aschenbach, L. C., Chen, J., Cassidy, M. P., Stevens, D. L., Gabra, B. H., Selley, D. E., Dewey, W. L., Westkaemper, R. B., and Zhang, Y. (2009) Design, Synthesis and Biological Evaluation of 6α- and 6β- N -Heterocyclic Substituted Naltrexamine Derivatives as Mu Opioid Receptor Selective Antagonists J. Med. Chem. 52, 1416-1427
21. Thompson, C. M., Wojno, H., Greiner, E., May, E. L., Rice, K. C., and Selley, D. E. (2004) Activation of G-proteins by morphine and codeine congeners: insights to the relevance of O- and N-demethylated metabolites at mu- and delta-opioid receptors J. Pharmacol. Exp. Ther. 308, 547-554 (Pubitemid 38134216)
22. Sim-Selley, L. J., Scoggins, K. L., Cassidy, M. P., Smith, L. A., Dewey, W. L., Smith, F. L., and Selley, D. E. (2007) Region-dependent attenuation of mu opioid receptor-mediated G-protein activation in mouse CNS as a function of morphine tolerance Br. J. Pharmacol. 151, 1324-1333 (Pubitemid 47255897)
23. Raehal, K. M., Lowery, J. J., Bhamidipati, C. M., Paolino, R. M., Blair, J. R., Wang, D., Sadée, W., and Bilsky, E. J. (2005) In vivo characterization of 6beta-naltrexol, an opioid ligand with less inverse agonist activity compared with naltrexone and naloxone in opioid-dependent mice J. Pharmacol. Exp. Ther. 313, 1150-1162 (Pubitemid 40727018)
24. Vaupel, D. B., Kimes, A. S., and London, E. D. (1997) Further in vivo studies on attenuating morphine withdrawal: isoform-selective nitric oxide synthase inhibitors differ in efficacy Eur. J. Pharmacol. 324, 11-20 (Pubitemid 27160903)