3D-QSAR comparative molecular field analysis on opioid receptor antagonists: Pooling data from different studies

Journal of Medicinal Chemistry

Volumn 48, Issue 5, 2005, Pages 1620-1629

  Peng, Youyi ^a   Keenan, Susan M ^a   Zhang, Qiang ^a   Kholodovych, Vladyslav ^a   Welsh, William J ^a  

^a RUTGERS ROBERT WOOD JOHNSON MEDICAL SCHOOL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DELTA OPIATE RECEPTOR; DELTORPHIN; ENKEPHALIN[2 DEXTRO ALANINE 4 METHYLPHENYLALANINE 5 GLYCINE]; ENKEPHALIN[2 DEXTRO ALANINE 5 DEXTRO LEUCINE]; KAPPA OPIATE RECEPTOR; MU OPIATE RECEPTOR; N METHYL N [7 (1 PYRROLIDINYL) 1 OXASPIRO[4.5]DEC 8 YL]BENZENEACETAMIDE; NALTREXONE; NALTRINDOLE; OPIATE ANTAGONIST;

ARTICLE; COMPARATIVE MOLECULAR FIELD ANALYSIS; DATA ANALYSIS; DRUG RECEPTOR BINDING; MOLECULAR MODEL; NONHUMAN; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RAT; RECEPTOR AFFINITY; REGRESSION ANALYSIS; STEREOCHEMISTRY;

ELECTROSTATICS; LEAST-SQUARES ANALYSIS; LIGANDS; MODELS, MOLECULAR; NALTREXONE; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; RECEPTORS, OPIOID; RECEPTORS, OPIOID, DELTA; RECEPTORS, OPIOID, KAPPA; RECEPTORS, OPIOID, MU;

EID: 14944378406     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm049117e     Document Type: Article

References (36)

1. Dhawan, B. N.; Cesselin, F.; Raghubir, R.; Reisine, T.; Bradley, P. B.; Portoghese, P. S.; Hamon, M. International Union of Pharmacology. XII. Classification of opioid receptors. Pharmacol. Rev. 1996, 48, 567-592.
2. Pert, C. B.; Snyder, S. H. Opiate receptor: Demonstration in nervous tissue. Science 1973, 179, 1011-1014.
3. Law, P. Y.; Wong, Y. H.; Loh, H. H. Molecular mechanisms and regulation of opioid receptor signaling. Annu. Rev. Pharmacol. Toxicol. 2000, 40, 389-430.
4. Abdelhamid, E. E.; Sultana, M.; Portoghese, P. S.; Takemori, A. E. Selective blockage of delta opioid receptors prevents the development of morphine tolerance and dependence in mice. J. Pharmacol. Exp. Ther. 1991, 258, 299-303.
5. Reid, L. D.; Hubbell, C. L.; Glaccum, M. B.; Bilsky, E. J.; Portoghese, P. S.; Porreca, F. Naltrindole, an opioid delta receptor antagonist, blocks cocaine-induced facilitation of responding for rewarding brain stimulation. Life Sci. 1993, 52, PL67-71.
6. House, R. V.; Thomas, P. T.; Kozak, J. T.; Bhargava, H. N. Suppression of immune function by nonpeptidic delta opioid receptor antagonists. Neurosci. Lett. 1995, 198, 119-122.
7. Schiller, P. W.; Fundytus, M. E.; Merovitz, L.; Weltrowska, G.; Nguyen, T. M.; Lemieux, C.; Chung, N. N.; Coderre, T. J. The opioid mu agonist/delta antagonist DIPP-NH(2)[Psi] produces a potent analgesic effect, no physical dependence, and less tolerance than morphine in rats. J. Med. Chem. 1999, 42, 3520-3526.
8. Coop, A.; Rothman, R. B.; Dersch, C.; Partilla, J.; Porreca, F.; Davis, P.; Jacobson, A. E.; Rice, K. C. Delta opioid affinity and selectivity of 4-hydroxy-3-methoxyindolomorphinan analogues related to naltrindole. J. Med. Chem. 1999, 42, 1673-1679.
9. Portoghese, P. S. Edward E. Smissman-Bristol-Myers Squibb Award Address. The role of concepts in structure-activity relationship studies of opioid ligands. J. Med. Chem. 1992, 35, 1927-1937.
10. Portoghese, P. S.; Sultana, M.; Takemori, A. E. Naltrindole, a highly selective and potent non-peptide delta opioid receptor antagonist. Eur. J. Pharmacol. 1988, 146, 185-186.
11. McLamore, S.; Ullrich, T.; Rothman, R. B.; Xu, H.; Dersch, C.; Coop, A.; Davis, P.; Porreca, F.; Jacobson, A. E.; Rice, K. C. Effect of N-alkyl and N-alkenyl substituents in noroxymorphindole, 17-substituted-6,7-dehydro-4, 5α-epoxy-3,14-dihydroxy-6,7:2′,3′-indolomorphinans, on opioid receptor affinity, selectivity, and efficacy. J. Med. Chem. 2001, 44, 1471-1474.
12. Ananthan, S.; Johnson, C. A.; Carter, R. L.; Clayton, S. D.; Rice, K. C.; Xu, H.; Davis, P.; Porreca, F.; Rothman, R. B. Synthesis, opioid receptor binding, and bioassay of naltrindole analogues substituted in the indolic benzene moiety. J. Med. Chem. 1998, 41, 2872-2881.
13. Ananthan, S.; Kezar, H. S. 3rd; Carter, R. L.; Saini, S. K.; Rice, K. C.; Wells, J. L.; Davis, P.; Xu, H.; Dersch, C. M.; Bilsky, E. J.; Porreca, F.; Rothman, R. B. Synthesis, opioid receptor binding, and biological activities of naltrexone-derived pyrido-and pyrimidomorphinans. J. Med. Chem. 1999, 42, 3527-3538.
14. Yu, H.; Prisinzano, T.; Dersch, C. M.; Marcus, J.; Rothman, R. B.; Jacobson, A. E.; Rice, K. C. Synthesis and biological activity of 8β-substituted hydrocodone indole and hydromorphone indole derivatives. Bioorg. Med. Chem. Lett. 2002, 12, 165-168.
15. Ullrich, T.; Dersch, C. M.; Rothman, R. B.; Jacobson, A. E.; Rice, K. C. Derivatives of 17-(2-methylallyl)-substituted noroxymorphone: Variation of the delta address and its effects on affinity and selectivity for the delta opioid receptor. Bioorg. Med. Chem. Lett. 2001, 11, 2883-2885.
16. Kubota, H.; Rothman, R. B.; Dersch, C.; McCullough, K.; Pinto, J.; Rice, K. C. Synthesis and biological activity of 3-substituted 3-desoxynaltrindole derivatives. Bioorg. Med. Chem. Lett. 1998, 8, 799-804.
17. Kshirsagar, T. A.; Fang, X.; Portoghese, P. S. 14-Desoxy analogues of naltrindole and 7-spiroindanyloxymorphone: The role of the 14-hydroxy group at delta opioid receptors. J. Med. Chem. 1998, 41, 2657-2660.
18. Gao, P.; Larson, D. L.; Portoghese, P. S. Synthesis of 7-arylmorphinans. Probing the "address" requirements for selectivity at opioid delta receptors. J. Med. Chem. 1998, 41, 3091-3098.
19. Le Dain, A. C.; Madsen, B. W.; Skelton, B. W.; White, A. H. Crystal structure of naltrexone hydrocholide: Implications for location of the nicotinic receptor noncompetitive inhibor binding site. Aust. J. Chem. 1992, 45, 635-640.
20. Sybyl 6.8; Tripos, Inc.: St. Louis, MO.
21. Thomas, J. B.; Atkinson, R. N.; Namdev, N.; Rothman, R. B.; Gigstad, K. M.; Fix, S. E.; Mascarella, S. W.; Burgess, J. P.; Vinson, N. A.; Xu, H.; Dersch, C. M.; Cantrell, B. E.; Zimmerman, D. M.; Carroll, F. I. Discovery of an opioid kappa receptor selective pure antagonist from a library of N-substituted 4β-methyl-5-(3-hydroxyphenyl)morphans. J. Med. Chem. 2002, 45, 3524-3530.
22. Ananthan, S.; Khare, N. K.; Saini, S. K.; Seitz, L. E.; Bartlett, J. L.; Davis, P.; Dersch, C. M.; Porreca, F.; Rothman, R. B.; Bilsky, E. J. Identification of opioid ligands possessing mixed micro agonist/delta antagonist activity among pyridomorphinans derived from naloxone, oxymorphone, and hydromorphone. J. Med. Chem. 2004, 47, 1400-1412.
23. Spetea, M.; Schullner, F.; Moisa, R. C.; Berzetei-Gurske, I. P.; Schraml, B.; Dorfler, C.; Aceto, M. D.; Harris, L. S.; Coop, A.; Schmidhammer, H. Synthesis and biological evaluation of 14-alkoxymorphinans. 21. Novel 4-alkoxy and 14-phenylpropoxy derivatives of the mu opioid receptor antagonist cyprodime. J. Med. Chem. 2004, 47, 3242-3247.
24. Schmidhammer, H.; Daurer, D.; Wieser, M. Synthesis and biological evaluation of 14-alkoxymorphinans.14. 14-ethoxy-5-methyl substituted indolomorphinans with delta opioid receptor selectivity. Bioorg. Med. Chem. Lett. 1997, 7, 151-156.
25. Schwyzer, R. ACTH: A short introductory review. Ann. N.Y. Acad. Sci. 1977, 297, 3-26.
26. Portoghese, P. S. Bivalent ligands and the message-address concept in the design of selective opioid receptor antagonists. Trends Pharmacol. Sci. 1989, 10, 230-235.
27. Portoghese, P. S.; Moe, S. T.; Takemori, A. E. A selective delta 1 opioid receptor agonist derived from oxymorphone. Evidence for separate recognition sites for delta 1 opioid receptor agonists and antagonists. J. Med. Chem. 1993, 36, 2572-2574.
28. Takemori, A. E.; Portoghese, P. S. Selective naltrexone-derived opioid receptor antagonists. Annu. Rev. Pharmacol. Toxicol. 1992, 32, 239-269.
29. Portoghese, P. S.; Sultana, M.; Takemori, A. E. Design of peptidomimetic delta opioid receptor antagonists using the message-address concept. J. Med. Chem. 1990, 33, 1714-1720.
30. Shenderovich, M. D.; Liao, S.; Qian, X.; Hruby, V. J. A three-dimensional model of the delta-opioid pharmacophore: Comparative molecular modeling of peptide and nonpeptide ligands. Biopolymers 2000, 53, 565-580.
31. Portoghese, P. S.; Nagase, H.; Takemori, A. E. Only one pharmacophore is required for the kappa opioid antagonist selectivity of norbinaltorphimine. J. Med. Chem. 1988, 31, 1344-1347.
32. Lin, C. E.; Takemori, A. E.; Portoghese, P. S. Synthesis and kappa-opioid antagonist selectivity of a norbinaltorphimine congener. Identification of the address moiety required for kappa-antagonist activity. J. Med. Chem. 1993, 36, 2412-2415.
33. Stevens, W. C., Jr.; Jones, R. M.; Subramanian, G.; Metzger, T. G.; Ferguson, D. M.; Portoghese, P. S. Potent and selective indolomorphinan antagonists of the kappa-opioid receptor. J. Med. Chem. 2000, 43, 2759-2769.
34. Metzger, T. G.; Paterlini, M. G.; Ferguson, D. M.; Portoghese, P. S. Investigation of the selectivity of oxymorphone- and naltrexone-derived ligands via site-directed mutagenesis of opioid receptors: Exploring the "address" recognition locus. J. Med. Chem. 2001, 44, 857-862.
35. Grundt, P.; Jales, A. R.; Traynor, J. R.; Lewis, J. W.; Husbands, S. M. 14-amino, 14-alkylamino, and 14-acylamino analogues of oxymorphindole. Differential effects on opioid receptor binding and functional profiles. J. Med. Chem. 2003, 46, 1563-1566.
36. Harnett, D. L.; Murphy, J. L. Introductory Statistical Analysis; Addison-Wesley Publishing Co.: Philippines, 1975; p 430.