Structure-activity relationships of nociceptin and related peptides: Comparison with dynorphin A

Peptides

Volumn 21, Issue 7, 2000, Pages 923-933

  Guerrini, Remo ^a   Calo', Girolamo ^a   Rizzi, Anna ^a   Bigoni, Raffaella ^a   Rizzi, Daniela ^a   Regoli, Domenico ^a   Salvadori, Severo ^a  

^a UNIVERSITY OF FERRARA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1 (1 CYCLOOCTYLMETHYL 3 HYDROXYMETHYL 4 PIPERIDYL) 3 ETHYL 1,3 DIHYDRO 2H BENZIMIDAZOL 2 ONE; 3,4 DICHLORO N METHYL N [2 (1 PYRROLIDINYL)CYCLOHEXYL]BENZENEACETAMIDE; 5,9 DIETHYL 2 (3 FURYLMETHYL) 2' HYDROXY 6,7 BENZOMORPHAN; BUPRENORPHINE; CATION; DELTORPHIN; DYNORPHIN A; ENDOMORPHIN 1; ETORPHINE; GLYCINE; LOFENTANIL; MR 2267; NOCICEPTIN; NOCICEPTIN RECEPTOR; NORBINALTORPHIMINE; OPIATE AGONIST; OPIATE ANTAGONIST; OPIATE PEPTIDE; OPIATE RECEPTOR; PARTIAL AGONIST; PHENYLALANINE; TETRAPEPTIDE; TYROSINE; UNCLASSIFIED DRUG;

AMINO TERMINAL SEQUENCE; CARBOXY TERMINAL SEQUENCE; CHEMICAL BOND; CHEMICAL MODIFICATION; NONHUMAN; PHARMACOPHORE; PRIORITY JOURNAL; RECEPTOR AFFINITY; RECEPTOR OCCUPANCY; REVIEW; SEQUENCE HOMOLOGY; STRUCTURE ACTIVITY RELATION;

EID: 0033811973     PISSN: 01969781     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0196-9781(00)00229-1     Document Type: Article

References (75)

1. Adam G, Cesura A, Galley G, et al. New 8-substitute-1,3,8-triazaspiro[4.5]decan-4-on derivatives - useful for the treatment of diseases related to the Orphanin FQ receptor e.g. psychiatric, neurological and physiological disorders. Switzerland EP-8 1998:56514.
2. Bauer U., Nakazi M., Kathmann M., Gothert M., Schlicker E. The stereoselective κ-opioid receptor antagonist Mr 2266 does not exhibit stereoselectivity as an antagonist at the orphan opioid (ORL1) receptor. Naunyn Schmiedebergs Arch Pharmacol. 359:1999;17-20.
3. Becker J.A., Wallace A., Garzon A., et al. Ligands for κ-opioid, and ORL1 receptors identified from a conformationally constrained peptide combinatorial library. J Biol Chem. 274:1999;27513-27522.
4. Berzetei-Gurske I.P., Schwartz R.W., Toll L. Determination of activity for nociceptin in the mouse vas deferens. Eur J Pharmacol. 302:1996;R1-R2.
5. Bigoni R., Giuliani S., Calo G., et al. Characterization of nociceptin receptors in the periphery in vitro and in vivo studies . Naunyn Schmiedebergs Arch Pharmacol. 359:1999;160-167.
6. Butour J.L., Moisand C., Mazarguil H., Mollereau C., Meunier J.C. Recognition and activation of the opioid receptor-like ORL 1 receptor by nociceptin, nociceptin analogs and opioids. Eur J Pharmacol. 321:1997;97-103.
7. Calo G., Guerrini R., Bigoni R., et al. Structure-activity study of the nociceptin(1-13)-NH2 N-terminal tetrapeptide and discovery of a nociceptin receptor antagonist. J Med Chem. 41:1998;3360-3366.
8. Calo G., Guerrini R., Bigoni R., et al. Characterization of [Nphe1]NC(1-13)NH2, a new selective nociceptin receptor antagonist. Br J Pharmacol. 129:2000;1183-1193.
9. Calo G., Rizzi A., Bodin M., et al. Pharmacological characterization of nociceptin receptor an in vitro study . Can J Physiol Pharmacol. 75:1997;713-718.
10. Calo G., Rizzi A., Bogoni G., et al. The mouse vas deferens a pharmacological preparation sensitive to nociceptin . Eur J Pharmacol. 311:1996;R3-R5.
11. Cascieri M.A., Fong T.M., Strader C.D. Molecular characterization of a common binding site for small molecules within the transmembrane domain of G-protein coupled receptors. J Pharmacol Toxicol Methods. 33:1995;179-185.
12. Chang A.C., Takemori A.E., Ojala W.H., Gleason W.B., Portoghese P.S. kappa Opioid receptor selective affinity labels electrophilic benzeneacetamides as κ-selective opioid antagonists . J Med Chem. 37:1994;4490-4498.
13. Chavkin C., Goldstein A. Specific receptor for the opioid peptide dynorphin structure-activity relationships . Proc Natl Acad Sci USA. 78:1981;6543-6547.
14. Choi H., Murray T.F., DeLander G.E., Caldwell V., Aldrich J.V. N-terminal alkylated derivatives of [D-Pro10]dynorphin A-(1-11) are highly selective for κ-opioid receptors. J Med Chem. 35:1992;4638-4639.
15. Corbett A.D., Paterson S.J., McKnight A.T., Magnan J., Kosterlitz H.W. Dynorphin and dynorphin are ligands for the κ-subtype of opiate receptor. Nature. 299:1982;79-81.
16. Cotton R., Giles M. G, Miller L, Shaw JS, Timms D. ICI 174864: a highly selective antagonist for the opioid δ-receptor. Eur J Pharmacol. 97:1984;331-332.
17. Dhawan B.N., Cesselin F., Raghubir R., et al. International Union of Pharmacology. XII. Classification of opioid receptors. Pharmacol Rev. 48:1996;567-592.
18. Dooley C.T., Houghten R.A. Orphanin FQ receptor binding and analog structure activity relationships in rat brain . Life Sci. 59:1996;L23-L29.
19. Dooley C.T., Spaeth C.G., Berzetei-Gurske I.P., et al. Binding, and In vitro activities of peptides with high affinity for the Nociceptin/Orphanin FQ receptor, ORL1. J Pharmacol Exp Ther. 283:1997;735-741.
20. Fischer A., Forssmann W.G., Undem B.J. Nociceptin-induced inhibition of tachykinergic neurotransmission in guinea pig bronchus. J Pharmacol Exp Ther. 285:1998;902-907.
21. Gairin J.E., Mazarguil H., Alvinerie P., Botanch C., Cros J., Meunier J.C. N,N-diallyl-tyrosyl substitution confers antagonist properties on the κ-selective opioid peptide [D-Pro10]dynorphin A(1-11). Br J Pharmacol. 95:1988;1023-1030.
22. Giardina G., Clarke G.D., Grugni M., Sbacchi M., Vecchietti V. Central and peripheral analgesic agents chemical strategies for limiting brain penetration in κ-opioid agonists belonging to different chemical classes . Farmaco. 50:1995;405-418.
23. Giuliani S., Maggi C.A. Inhibition of tachykinin release from peripheral endings of sensory nerves by nociceptin, a novel opioid peptide. Br J Pharmacol. 118:1996;1567-1569.
24. Goldstein A., Tachibana S., Lowney L.I., Hunkapiller M., Hood L. Dynorphin-(1-13), an extraordinarily potent opioid peptide. Proc Natl Acad Sci USA. 76:1979;6666-6670.
25. Griffths E.C., McDermott J.R. Biotransformation of neuropeptides. Neuroendocrinology. 39:1984;573-581.
26. Guerrini R., Calo G., Rizzi A., Bianchi C., Lazarus L.H., Salvadori S., Temussi P.A., Regoli D. Address and message sequences for the nociceptin receptor a structure- activity study of nociceptin-(1-13)-peptide amide . J Med Chem. 40:1997;1789-1793.
27. Hibert M.F., Trumpp-Kallmeyer S., Bruinvels A., Hoflack J. Three-dimensional models of neurotransmitter G-binding protein-coupled receptors. Mol Pharmacol. 40:1991;8-15.
28. Hruby V.J., Gehrig C.A. Recent developments in the design of receptor specific opioid peptides. Med Res Rev. 9:1989;343-401.
29. Hughes J., Smith T.W., Kosterlitz H.W., Fothergill L.A., Morgan B.A., Morris H.R. Identification of two related pentapeptides from the brain with potent opiate agonist activity. Nature. 258:1975;577-580.
30. Ito F, Kondo H, Noguchi H, Ohashi Y, Yamagishi T. 4-(2-keto-1-benzimidazolinyl)piperidine compounds as ORL1-receptor agonists. WO 99 1999:36421.
31. Jenck F., Moreau J.L., Martin J.R., et al. Orphanin FQ acts as an anxiolytic to attenuate behavioral responses to stress. Proc Natl Acad Sci USA. 94:1997;14854-14858.
32. Kawamoto H., Ozaki S., Itoh Y., et al. Discovery of the fist potent and selective small molecule opioid receptor-like (ORL1) antagonist 1-[(3R,4R)-1-cyclooctylmethyl-3-hydroxymethyl-4-piperidyl]-3-ethyl-1,3-dihydro- 2H-benzimidazol-2-one (J-113397) . J Med Chem. 42:1999;5061-5063.
33. Lapalu S., Moisand C., Mazarguil H., Cambois G., Mollereau C., Meunier J.C. Comparison of the structure-activity relationships of nociceptin and dynorphin A using chimeric peptides. FEBS Lett. 417:1997;333-336.
34. Leslie F.M. Methods used for the study of opioid receptors. Pharmacol Rev. 39:1987;197-249.
35. Lovett J.A., Portoghese P.S. N,N-dialkylated leucine enkephalins as potential delta opioid receptor antagonists. J Med Chem. 30:1987;1144-1149.
36. Mansour A., Hoversten M.T., Taylor L.P., Watson S.J., Akil H. The cloned mu, delta and kappa receptors and their endogenous ligands evidence for two opioid peptide recognition cores . Brain Res. 700:1995;89-98.
37. Mansour A., Taylor L.P., Fine J.L., et al. Key residues defining the μ-opioid receptor-binding pocket a site-directed mutagenesis study . J Neurochem. 68:1997;344-353.
38. Menzies J.R., Glen T., Davies M.R., Paterson S.J., Corbett A.D. In vitro agonist effects of nociceptin and [Phe(1)psi(CH(2)-NH)Gly(2)]nociceptin(1-13)NH(2) in the mouse and rat colon and the mouse vas deferens. Eur J Pharmacol. 385:1999;217-223.
39. Metzger T.G., Paterlini M.G., Portoghese P.S., Ferguson D.M. Application of the message-address concept to the docking of naltrexone and selective naltrexone-derived opioid antagonists into opioid receptor models. Neurochem Res. 21:1996;1287-1294.
40. Meunier J.C. Nociceptin/orphanin FQ, and the opioid receptor-like ORL1 receptor. Eur J Pharmacol. 340:1997;1-15.
41. Meunier J.C., Mollereau C., Toll L., et al. Isolation and structure of the endogenous agonist of opioid receptor-like ORL1 receptor. Nature. 377:1995;532-535.
42. Meyer J.P., Davis P., Lee K.B., Porreca F., Yamamura H.I., Hruby V.J. Synthesis using a Fmoc-based strategy and biological activities of some reduced peptide bond pseudopeptide analogues of dynorphin A1. J Med Chem. 38:1995;3462-3468.
43. Millan M.J. Kappa-opioid receptors and analgesia. Trends Pharmacol Sci. 11:1990;70-76.
44. Mollereau C., Mouledous L., Lapalu S., et al. Distinct mechanisms for activation of the opioid receptor-like 1 and κ-opioid receptors by nociceptin and dynorphin A. Mol Pharmacol. 55:1999;324-331.
45. Mollereau C., Parmentier M., Mailleux P., et al. ORL1, a novel member of the opioid receptor family - cloning, functional expression and localization. FEBS Letters. 341:1994;33-38.
46. Morley J.S. Structure-activity relationships of enkephalin-like peptides. Annu Rev Pharmacol Toxicol. 20:1980;81-110.
47. Nicholson JR, Paterson SJ, McKnight AT. Characterization of the response in the rat vas deferens to the ORL-1 agonist nociceptin. Br J Pharmacol 119 Proceeding Suppl: 36P; 1996.
48. Nicol B., Okawa H., Rowbotham D.J., Lambert D.G. Effects of naloxone benzoylhydrazone on nociceptin signalling in rat brain and CHO cells expressing recombinant nociceptin receptors. Regul peptides. 80:1999;125.
49. Noda Y., Mamiya T., Nabeshima T., Nishi M., Higashioka M., Takeshima H. Loss of antinociception induced by naloxone benzoylhydrazone in nociceptin receptor-knockout mice. J Biol Chem. 273:1998;18047-18051.
50. Okawa H., Nicol B., Bigoni R., et al. Comparison of the effects of [Phe1psi(CH2-NH)Gly2]Nociceptin (1-13)NH2 in rat brain, rat vas deferens and CHO cells expressing recombinant human nociceptin receptors. Br J Pharmacol. 127:1999;123-130.
51. Ozaki S, Kawamoto H, Ito Y, Hayashi K, Iwasawa Y, Hirano K. New 2-oxoimidazole derivatives - are nociceptin receptor binding inhibitors useful e.g. as analgesics and for amelioreting brain function. Japan, WO98 1998:54168.
52. Paterlini G., Portoghese P.S., Ferguson D.M. Molecular simulation of dynorphin A-(1-10) binding to extracellular loop 2 of the κ-opioid receptor. A model for receptor activation. J Med Chem. 40:1997;3254-3262.
53. 2 selectively antagonizes nociceptin effects in the rabbit isolated ileum. Eur J Pharmacol in press: 2000;397:383-8.
54. Portoghese P.S. An approach to the design of receptor-type-selective non-peptide antagonists of peptidergic receptors delta opioid antagonists . J Med Chem. 34:1991;1757-1762.
55. Portoghese P.S. Bivalent ligands and the message-address concept in the design of selective opioid receptor antagonists. Trends Pharmacol Sci. 10:1989;230-235.
56. Rees D.C. Chemical structures and biological activities of non-peptide selective kappa opioid ligands. Prog Med Chem. 29:1992;109-139.
57. Reinscheid R.K., Ardati A., Monsma F.J. Jr, Civelli O. Structure-activity relationship studies on the novel neuropeptide orphanin FQ. J Biol Chem. 271:1996;14163-14168.
58. Reinscheid R.K., Higelin J., Henningsen R.A., Monsma F.J. Jr, Civelli O. Structures that delineate orphanin FQ and dynorphin A pharmacological selectivities. J Biol Chem. 273:1998;1490-1495.
59. Reinscheid R.K., Nothacker H.P., Bourson A., et al. Orphanin FQ a neuropeptide that activates an opioidlike G protein-coupled receptor . Science. 270:1995;792-794.
60. Rizzi A., Bigoni R., Cal G., Guerrini R., Salvadori S., Regoli D. [Nphe(1)]nociceptin-(1-13)-NH(2) antagonizes nociceptin effects in the mouse colon. Eur J Pharmacol. 385:1999;R3-R5.
61. Salvadori S., Guerrini R., Calo' G., Regoli D. Structure activity studies on nociceptin/orphanin FQ from full agonist, to partial agonist, to pure antagonist . Il Famaco. 54:1999;810-825.
62. Schiller P.W. Development of receptor-specific opioid peptide analogues. Prog Med Chem. 28:1991;301-340.
63. Schiller P.W., Weltrowska G., Schmidt R., et al. Subtleties of structure-agonist versus antagonist relationships of opioid peptides and peptidomimetics. J Recept Signal Transduct Res. 19:1999;573-588.
64. Shaw J.S., Miller L., Turnbull M.J., Gormley J.J., Morley J.S. Selective antagonists at the opiate δ-receptor. Life Sci. 31:1982;1259-1262.
65. Shimohigashi Y., Hatano R., Fujita T., et al. Sensitivity of opioid receptor-like receptor ORL1 for chemical modification on nociceptin, a naturally occurring nociceptive peptide. J Biol Chem. 271:1996;23642-23645.
66. Simon R.J., Kania R.S., Zuckermann R.N., et al. Peptoids a modular approach to drug discovery . Proc Natl Acad Sci USA. 89:1992;9367-9371.
67. Szmuszkovicz J., Von Voigtlander P.F. Benzeneacetamide amines structurally novel non-m mu opioids . J Med Chem. 25:1982;1125-1126.
68. Szmuszkovicz J., Von Voigtlander P.F., Kane M.P. A new nontricyclic antidepressant agent. Synthesis and activity of N-[trans-2-(dimethylamino)cyclopentyl]-N-(3,4-dichlorophenyl)propanamide and related compounds. J Med Chem. 24:1981;1230-1236.
69. Topham C.M., Mouledous L., Poda G., Maigret B., Meunier J.C. Molecular modelling of the ORL1 receptor and its complex with nociceptin. Protein Eng. 11:1998;1163-1179.
70. Varani K., Calo G., Rizzi A., et al. Nociceptin receptor binding in mouse forebrain membranes thermodynamic characteristics and structure activity relationships . Br J Pharmacol. 125:1998;1485-1490.
71. Varani K., Rizzi A., Calo G., et al. Pharmacology of [Tyr1]nociceptin analogs receptor binding and bioassay studies . Naunyn Schmiedebergs Arch Pharmacol. 360:1999;270-277.
72. Walker J.M., Moises H.C., Coy D.H., Baldrighi G., Akil H. Nonopiate effects of dynorphin and des-Tyr-dynorphin. Science. 218:1982;1136-1138.
73. Wichmann J., Adam G., Rover S., Cesura A.M., Dautzenberg F.M., Jenck F. 8-acenaphthen-1-yl-1-phenyl-1,3,8-triaza-spiro[4. 5]decan-4-one derivatives as orphanin FQ receptor agonists. Bioorg Med Chem Lett. 9:1999;2343-2348.
74. Wnendt S., Kruger T., Janocha E., Hildebrandt D., Englberger W. Agonistic effect of buprenorphine in a nociceptin/OFQ receptor-triggered reporter gene assay. Mol Pharmacol. 56:1999;334-338.
75. Zadina J.E., Hackler L., Ge L.J., Kastin A.J. A potent and selective endogenous agonist for the μ opiate receptor. Nature. 386:1997;499-502.