TIPP[ψ]: A Highly Potent and Stable Pseudopeptide δ Opioid Receptor Antagonist with Extraordinary δ Selectivity

Journal of Medicinal Chemistry

Volumn 36, Issue 21, 1993, Pages 3182-3187

  Schiller, Peter W ^a   Weltrowska, Grazyna ^a   Nguyen, Thi M D ^a   Wilkes, Brian C ^a   Chung, Nga N ^a   Lemieux, Carole ^a  

^a CLIN RESEARCH INSTITUTE OF MONTREAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

DELTA OPIATE RECEPTOR; KAPPA OPIATE RECEPTOR; MU OPIATE RECEPTOR; OPIATE ANTAGONIST; PSEUDOPEPTIDE; TETRAHYDROISOQUINOLINE;

ANIMAL TISSUE; ARTICLE; BIOASSAY; BRAIN MEMBRANE; DRUG CONFORMATION; DRUG DEGRADATION; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; DRUG STABILITY; DRUG SYNTHESIS; GUINEA PIG; ILEUM CONTRACTION; MOUSE; NONHUMAN; PRIORITY JOURNAL; RAT; RECEPTOR AFFINITY; VAS DEFERENS;

ANIMAL; BINDING SITES; GUINEA PIGS; MALE; MICE; MOLECULAR CONFORMATION; OLIGOPEPTIDES; RECEPTORS, OPIOID, DELTA; SUPPORT, NON-U.S. GOV'T; SUPPORT, U.S. GOV'T, P.H.S.;

EID: 0027489176     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm00073a020     Document Type: Article

References (31)

1. 2NH]Phe-Phe-OH; U69,593,(5α,7α,8β)-(−)-N-methyl-N-[7-(1-pyrrolidinyl)-1-oxaspiro-[4.5]dec-8-yl]benzeneacetamide.
2. Kazmierski, W.; Wire, W. S.; Lui, G. K.; Knapp, R. J.; Shook, J. E.; Burks, T. F.; Yamamura, H. I.; Hruby, V. J. Design and Synthesis of Somatostatin Analogs with Topographical Properties that Lead to Highly Potent and Specific μ Opioid Receptor Antagonists with Greatly Reduced Binding at Somatostatin Receptors. J. Med. Chem. 1988, 31, 2170–2177.
3. Portoghese, P. S.; Lipkowski, A. W.; Takemori, A. E. Binaltorphimine and Norbinaltorphimine, Potent and Selective κ-Opioid Receptor Antagonists. Life Sci. 1987, 40, 1287–1292.
4. Cotton, R.; Giles, M. G.; Miller, L.; Shaw, J. S.; Timms, D. ICI 174 864: A Highly Selective Antagonist for the Opioid δ-Receptor. Eur. J. Pharmacol. 1984, 97, 331–332.
5. Corbett, A. D.; Gillan, M. G. C.; Kosterlitz, H. W.; McKnight, A. T.; Paterson, S. J.; Robson, L. E. Selectivities of Opioid Peptide Analogues as Agonists and Antagonists at the δ-receptor. Br. J. Pharmacol. 1984, 83, 271–279.
6. Portoghese, P. S.; Sultana, M.; Nagase, H.; Takemori, A. E. Application of the Message-Address Concept in the Design of Highly Potent and Selective Non-Peptide 8 Opioid Receptor Antagonists. J. Med. Chem. 1988, 31, 281–282.
7. Portoghese, P. S.; Nagase, H.; MaloneyHuss, K. E.; Lin, C.-E.; Takemori, A. E. Role of Spacer and Address Components in Peptidomimetic S Opioid Receptor Antagonists Related to Naltrindole. J. Med. Chem. 1991, 34, 1715–1720.
8. Schiller, P. W.; Nguyen, T.M.D.; Weltrowska, G.; Wilkes, B. C.; Marsden, B. J.; Lemieux, C.; Chung, N. N. Differential Stereochemical Requirements of μ vs δ Opioid Receptors for Ligand Binding and Signal Transduction: Development of a Class of Potent and Highly δ-Selective Peptide Antagonists. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 11871–11875.
9. 3H]TIPP. Life Sci. 1993, 53, PL 57–62.
10. Marsden, B. J.; Nguyen, T.M.-D.; Schiller, P. W. Spontaneous Degradation via Diketopiperazine Formation of Peptides Containing a Tetrahydroisoquinoline-3-carboxylic Acid Residue in the 2-Position of the Peptide Sequence. Int. J. Pept. Protein Res. 1993, 41, 313–316.
11. 2NH Peptide Bond Isostere. Peptides 1987, 8, 119–121.
12. Fehrentz, J.-A.; Castro, B. An Efficient Synthesis of Optically Active α-(t-Butoxycarbonylamino)-aldehydes from α-Amino Acids. Synthesis 1983, 676–678.
13. Mosberg, H. I.; Hurst, R.; Hruby, V. J.; Gee, K.; Yamamura, H. I.; Galligan, J. J.; Burks, T. F. Bis-penicillamine Enkephalins Possess Highly Improved Specificity Toward δ Opioid Receptors. Proc. Natl. Acad. Sci. U.S.A. 1983, 80, 5871–5874.
14. Erspamer, V.; Melchiorri, P.; Falconieri-Erspamer, G.; Negri, L.; Corsi, R.; Severini, C.; Barra, D.; Simmaco, M.; Kreil, G. Deltorphins: A Family of Naturally Occurring Peptides with High Affinity and Selectivity for δ Opioid Binding Sites. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 5188–5192.
15. Schiller, P. W.; Nguyen, T.M.-D.; Chung, N. N.; Lemieux, C. Dermorphin Analogues Carrying an Increased Positive Net Charge in Their “Message” Domain Display Extremely High μ-Opioid Receptor Selectivity. J. Med. Chem. 1989, 32, 698–703.
16. 3H]U-69593, a Highly Selective Ligand for the Opioid κ Receptor. Eur. J. Pharmacol. 1985, 109, 281–284.
17. 5]enkephalin Analogues with Increased Affinity and Selectivity for δ Opioid Receptors. J. Med. Chem. 1990, 33, 249–253.
18. 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.
19. Arakawa, K.; Akami, T.; Okamoto, M.; Akioka, K.; Nakai, I.; Oka, T.; Nagase, H. Immunosuppression by Delta Opioid Receptor Antagonist. Transplant. Proc. 1993, 25, 738–740.
20. Kaiser, E.; Colescott, R. L.; Bossinger, D. C.; Cook, P. I. Color Test for the Detection of Free Terminal Amino Groups in the Solid-Phase Synthesis of Peptides. Anal. Biochem. 1970, 34, 595–598.
21. Paton, W. D. M. The Action of Morphine and Related Substances on Contraction and on Acetylcholine Output of Coaxially Stimulated Guinea Pig Ileum. Br. J. Pharmacol. 1957, 12, 119–127.
22. Henderson, G.; Hughes, J.; Kosterlitz, H. W. A New Example of a Morphine Sensitive Neuroeffector Junction. Br. J. Pharmacol. 1972, 46, 764–766.
23. Schiller, P. W.; Lipton, A.; Horrobin, D. F.; Bodanszky, M. Unsulf ated C-terminal 7-Peptide of Cholecystokinin: A New Ligand of the Opiate Receptor. Biochem. Biophys. Res. Commun. 1978, 85, 1332–1338.
24. DiMaio, J.; Nguyen, T.M.-D.; Lemieux, C.; Schiller, P. W. Synthesis and Pharmacological Characterization In Vitro of Cyclic Enkephalin Analogues: Effects of Conformational Constraints on Opiate Receptor Selectivity. J. Med. Chem. 1982, 25, 1432–1438.
25. 65-Analogue. Comparison of the Binding Properties of Methionine- and Leucine-Enkephalin. Eur. J. Pharmacol. 1979, 58, 11–18.
26. Kosterlitz, H. W.; Watt, A. J. Kinetic Parameters of Narcotic Agonists and Antagonists with Particular Reference to N-Allylnoroxymorphone (Naloxone). Br. J. Pharmacol. 1968, 33, 266–276.
27. 50) of an Enzymatic Reaction. Biochem. Pharmacol. 1973, 22, 3099–3102.
28. DiMaio, J.; Schiller, P. W. A Cyclic Enkephalin Analog with High In Vitro Opiate Activity. Proc. Natl. Acad. Sci. U.S.A. 1980, 77, 7162–7166.
29. Clark, M.; Cramer, R. D., III; Opdenbosh, N. V. Validation of the General Purpose Tripos 5.2 Force Field. J. Comp. Chem. 1989, 10, 982–1012.
30. Wilkes, B. C.; Schiller, P. W. Theoretical Conformational Analysis of a μ-Selective Cyclic Opioid Peptide Analog. Biopolymers 1987, 26, 1431–1444.
31. Wilkes, B. C.; Schiller, P. W. Molecular Dynamics Simulations of Opioid Peptide Analogs Containing Multiple Conformational Restrictions. Int. J. Pept. Protein Res. 1992, 40, 249–254.