Abstract
Opioid antagonists have been indispensable as tools in opioid research (Zimmerman and Leander 1990). In fact, the chief criterion for the classification of an agonist effect as opioid receptor-mediated is the ability of naloxone (Sawynok et al. 1979) or naltrexone (Gold et al. 1982) to reversibly antagonize this effect in a competitive fashion. The usefulness of these ligands for this purpose stems from the fact that they are universal opioid antagonists; that is, they are capable of antagonizing the agonist effects mediated by multiple opioid receptor types.
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References
Belleney J, Gacel G, Fournie-Zaluski MC, Maigret B, Roques BP (1989) δ opioid receptor selectivity induced by conformational constraints in linear enkephalin- related peptides: 1H 400-MHz NMR study and theoretical calculations. Biochemistry 28:7392–7400
Birch PJ, Hayes AG, Sheehan MJ, Tyers MB (1987) Norbinaltorphimine: antagonist profile at K opioid receptors. Eur J Pharmacol 144: 405–408
Burgen ASV, Roberts GCK, Feeny J (1975) Binding of flexible ligands to macromolecules. Nature 253: 753–755
Chavkin C, Goldstein A (1981) Specific receptor for the opioid peptide dynorphin. Proc Natl Acad Sci USA 78: 6543–6547
Cotton R, Giles MG, Miller L, Shaw JS, Timms D (1984) A highly selective antagonist for the delta receptor. Eur J Pharmacol 97: 331–332
Cruciani RA, Lutz RA, Munson PJ, Rodbard D (1987) Naloxonazine effects on the interaction of enkephalin analogs with mu-1, mu-2, and delta opioid binding sites in rat brain membranes. J Pharmacol Exp Ther 242: 15–20
Endoh T, Koike H, Matsura H, Nagase H (1990) Nor-binaltorphimine (nor-BNI); a potent and selective kappa opioid receptor antagonist with ultralong-lasting activity in vivo. In: van Ree JM, Mulder AH, Wiegant VM, van Wimersma Greidanus TB (eds) New leads in opioid research. Excerpta Medica, Amsterdam, pp 82–83
Erez M, Takemori AE, Portoghese PS (1982) Narcotic antagonistic potency of bivalent ligands which contain β-naltrexamine. Evidence for bridging between proximal recognition sites. J Med Chem 25: 847–849
Fournie-Zaluski M-C, Gacel G, Maigret B, Premilat S, Roques BP (1981) Structural requirements for specific recognition of μ or δ opiate receptors. Mol Pharmacol 20: 484–491
Garzon-Aburbeh A, Lipkowski AW, Larson DL, Portoghese PS (1989) Transfer of fatty acyl groups from membrane phospatides to opiate ligands. Neurochem Int 15: 207–214
Gold MS, Dackis CA, Pottash ALC, Sternbach HH, Annetto WJ, Martin D, Dakis MP (1982) Naltrexone, opiate addiction, and endorphins. Med Res Rev 2: 211–246
Herz A (1987) The multiplicity of opioid receptors and their functional significance. In: Mutschler E, Winterfeldt E (eds) Trends in medicinal chemistry. VCH, Weinheim, pp 337–350
Hruby VJ, Gehrig CA (1989) Recent developments in the design of receptor specific opioid peptides. Med Res Rev 9: 343–401
Iijima I, Minamikawa J, Jacobson AE, Brossi A, Rice K, Klee WA (1978) Studies in the (+)-morphinan series: 5. Synthesis and biological properties of (+)-naloxone. J Med Chem 21: 398–400
Ishida T, Yoneda S, Doi M, Inoue M, Kitamura K (1988) Molecular-dynamics simulations of [Met5]- and [D-Ala2,Met5]-enkephalins. Biochem J 255: 621–628
Jacob JJC, Ramabadran K (1977) Opioid antagonists, endogenous ligands and antinociception. Eur J Pharmacol 46: 393–394
Johnson N, Pasternak GW (1984) Binding of [3H]naloxonazine to rat brain membranes. Mol Pharmacol 26: 477–483
Kawai H, Kikuchi T, Okamoto Y (1989) A prediction of tertiary structures of peptide by the Monte Carlo simulated annealing method. Protein Eng 3: 85–94
Ling GSF, Simantov R, Clark JA, Pasternak GW (1986) Naloxonazine actions in vivo. Eur J Pharmacol 129: 33–38
Lipkowski AW, Tam SW, Portoghese PS (1986) Peptides as receptor selectivity modulators of opiate pharmacophores. J Med Chem 29: 1222–1225
Michne WF, Lewis TR, Michalec SJ, Pierson AK, Gillan MGC, Paterson SJ, Robson LE, Kosterlitz HW (1978) Novel developments of N-methylbenzomorphan narcotic antagonists. In: Van Ree JM, Terenius L (eds) Characteristics and functions of opioids. Elsevier, Amsterdam, pp 197–206
Olson GA, Olson RD, Kastin AJ (1989) Endogenous opiates: 1987. Peptides 10: 205–236
Pasternak GW, Hahn EF (1980) Long-acting opiate agonists and antagonists: 14-Hydroxydihydromorphinone hydrazones. J Med Chem 23: 674–676
Paterson SJ, Robson LE, Kosterlitz HW (1984) Opioid receptors. In: Udenfriend S, Meienhofer J (eds) The peptides, vol 6. Academic, New York, pp 147–187
Portoghese PS (1970) Relationship between stereostructure and pharmacological activities. Annu Rev Pharmacol 10: 51–76
Portoghese PS (1987) Bivalent ligands in the development of selective opioid receptor antagonists. In: Mutschler E, Winterfeldt E (eds) Trends in medicinal chemistry. VCH, Weinheim, pp 327–336
Portoghese PS (1989) Bivalent ligands and the message-address concept in the design of selective opioid antagonists. Trends Pharmacol Sci 10: 230–235
Portoghese PS, Takemori AE (1985) TENA, a selective kappa opioid receptor antagonist. Life Sci 36: 801–805
Portoghese PS, Larson DL, Say re LM, Yim CB, Ronsisvalle G, Tam SW, Takemori AE (1986) Opioid agonist and antagonist bivalent ligands. The relationship between spacer length and selectivity at multiple opioid receptors. J Med Chem 29: 1855–1861
Portoghese PS, Lipkowski AW, Takemori AE (1987) Binaltorphimine and norbinaltorphimine, potent and selective к-opioid receptor antagonists. Life Sci 40: 1287–1292
Portoghese PS, Sultana M, Takemori AE (1988a) Naltrindole, a highly selective and potent non-peptide 5-opioid receptor antagonist. Eur J Pharmacol 146: 185–186
Portoghese PS, Sultana M, Nagase H, Takemori AE (1988b) The message-address concept in the design of highly potent and selective opioid receptor antagonists. In: Melchiorre C, Gianella M (eds) Recent advances in receptor chemistry. Elsevier, Amsterdam, pp 307–317
Portoghese PS, Sultana M, Takemori AE (1988c) Application of the message-address concept in the design of highly potent and selective non-peptide 5- opioid receptor antagonists. J Med Chem 31: 281–282
Portoghese PS, Nagase H, Lipkowski AW, Larson DL, Takemori AE (1988d) Binaltorphimine-related bivalent ligands and their K opioid receptor antagonist selectivity. J Med Chem 31: 836–841
Portoghese PS, Nagase H, Takemori AE (1988e) Only one pharmacophore is required for the K opioid antagonist selectivity of norbinaltorphimine. J Med Chem 31: 1344–1347
Portoghese PS, Sultana M, Takemori AE (1990) Design of peptidomimetic 8 opioid receptor antagonists using the message-address concept. J Med Chem 33: 1714–1720
Portoghese PS, Nagase H, MaloneyHuss KE, Lin C-E, Takemori AE (1991) Investigation of the spacer and address components in 5 opioid antagonists related to naltrindole. J Med Chem 34: 1715–1720
Renugopalakrishnan V, Rapaka RS, Bhargava HN (1990) Conformational features of opioid peptides: ligand-receptor interactions. In: Szekely J, Ramabadran K (eds) Biochemistry and applied physiology. CRC Press, Boca Raton, pp 53–114 (Opioid peptides, vol 4 )
Sawynok J, Pinsky C, LaBella FS (1979) Minireview on the specificity of naloxone as an opiate antagonist. Life Sci 25: 1621–1632
Schild HO (1957) Drug antagonism and pAx. Pharmacol Rev 9: 242–246
Schiller P (1984) Conformational analysis of enkephalin and conformation-activity relationships. In: Udenfriend S, Meienhofer J (eds) The peptides, vol 6. Academic, New York, pp 219–268
Schmidhammer H, Burkhard WP, Eggstein-Aeppli L, Smith CFC (1989) Synthesis and biological evaluation of 14-alkoxymorphinans: 2. (-)-N-(cyclopropylmethyl)- 4,14-dimethoxymorphinan-6-one, a selective μ opioid receptor antagonist. J Med Chem 32: 418–421
Schwyzer R (1977) ACTH: a short introductory review. Ann NY Acad Sci 297: 3–26
Smits SE, Takemori AE (1970) Quantitative studies on the antagonism by naloxone of some narcotic-antagonist analgesics. Br J Pharmacol 39: 627–638
Sofuoglu M, Portoghese PS, Takemori AE (1991) Differential antagonism of delta opioid agonists by naltrindole (NTI) and its benzofuran analog (NTB) in mice: evidence for delta opioid receptor subtypes. J Pharmacol Exp Ther (in press)
Szmuszkovicz J, von Voigtlander PF (1982) Benzeneacetamide amines: structurally novel non-mu opioids. J Med Chem 25: 1125–1126
Takemori AE, Portoghese PS (1984) Comparative antagonism by naltrexone and naloxone of K, and 8 agonists. Eur J Pharmacol 154: 101–104
Takemori AE, Ho BY, Naeseth JS, Portoghese PS (1988) Nor-binaltorphimine, a highly selective kappa-opioid antagonist in analgesic and receptor binding assays. J Pharmacol Exp Ther 246: 255–258
Tallarida RJ, Cowan A, Adler MW (1979) pA2 and receptor differentiation: a statistical analysis of competitive antagonism. Life Sci 25:637–654
Yoneda S, Kitamura K, Doi M, Inoue M, Ishida T (1988) Importance for folded monomer and extended antiparallel dimer structures as enkephalin active conformation. FEBS Lett 239: 271–275
Zimmerman DM, Leander JD (1990) Selective opioid receptor agonists and antagonists: research tools and potential therapeutic agents. J Med Chem 33: 895–902
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Portoghese, P.S. (1993). Selective Nonpeptide Opioid Antagonists. In: Herz, A., Akil, H., Simon, E.J. (eds) Opioids. Handbook of Experimental Pharmacology, vol 104 / 1. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-77460-7_12
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DOI: https://doi.org/10.1007/978-3-642-77460-7_12
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