Structure–activity studies on different modifications of nociceptin/orphanin FQ: Identification of highly potent agonists and antagonists of its receptor

Regulatory Peptides - Tập 130 - Trang 116-122 - 2005
Min Chang1, Ya-li Peng1, Shou-liang Dong1, Ren-wen Han1, Wei Li1, Ding-jian Yang1, Qiang Chen1, Rui Wang1
1Department of Biochemistry and Molecular Biology, School of Life Science, Lanzhou University, 222 Tian Shui South Road, Lanzhou 730000, PR China

Tài liệu tham khảo

Meunier, 1995, Isolation and structure of the endogenous agonist of opioid receptor-like ORL1 receptor, Nature, 377, 532, 10.1038/377532a0 Reinscheid, 1995, Orphanin FQ: a neuropeptide that activates an opioidlike G protein-coupled receptor, Science, 270, 792, 10.1126/science.270.5237.792 Cox, 2000, 321 Chen, 1994, Molecular cloning, tissue distribution and chromosomal localization of a novel member of the opioid receptor gene family, FEBS Lett, 347, 279, 10.1016/0014-5793(94)00560-5 Mollereau, 1994, ORL1, a novel member of the opioid receptor family. Cloning, functional expression and localization, FEBS Lett, 341, 33, 10.1016/0014-5793(94)80235-1 Wang, 1994, cDNA cloning of an orphan opiate receptor gene family member and its splice variant, FEBS Lett, 348, 75, 10.1016/0014-5793(94)00557-5 Calo, 2000, Pharmacology of nociceptin and its receptor: a novel therapeutic target, Br J Pharmacol, 129, 1261, 10.1038/sj.bjp.0703219 Mogil, 2001, The molecular and behavioral pharmacology of the orphanin FQ/nociceptin peptide and receptor family, Pharmacol Rev, 53, 381 Guerrini, 2000, Further studies on nociceptin-related peptides: discovery of a new chemical template with antagonist activity on the nociceptin receptor, J Med Chem, 43, 2805, 10.1021/jm990075h Calo, 2000, Characterization of [Nphe1]nociceptin(1–13)NH2, a new selective nociceptin receptor antagonist, Br J Pharmacol, 129, 1183, 10.1038/sj.bjp.0703169 Dooley, 1996, Orphanin FQ: receptor binding and analog structure activity relationships in rat brain, Life Sci, 59, L23, 10.1016/0024-3205(96)00261-5 Okada, 2000, Highly potent nociceptin analog containing the Arg–Lys triple repeat, Biochem Biophys Res Commun, 278, 493, 10.1006/bbrc.2000.3822 Rizzi, 2002, [Arg14, Lys15]nociceptin, a highly potent agonist of the nociceptin/orphanin FQ receptor: in vitro and in vivo studies, J Pharmacol Exp Ther, 300, 57, 10.1124/jpet.300.1.57 Guerrini, 2001, Structure–activity studies of the Phe4 residue of nociceptin(1–13)-NH2: identification of highly potent agonists of the nociceptin/orphanin FQ receptor, J Med Chem, 44, 3956, 10.1021/jm010221v Bigoni, 2002, Pharmacological characterisation of [(pX)Phe4]nociceptin(1–13)amide analogues: 1. In vitro studies, Naunyn Schmiedebergs Arch Pharmacol, 365, 442, 10.1007/s00210-002-0548-8 Rizzi, 2002, Pharmacological characterisation of [(pX)Phe4]nociceptin(1–13)amide analogues: 2. In vivo studies, Naunyn Schmiedebergs Arch Pharmacol, 365, 450, 10.1007/s00210-002-0549-7 Zhang, 2002, Novel, potent ORL-1 receptor agonist peptides containing α-helix-promoting conformational constraints, J Med Chem, 45, 5280, 10.1021/jm0202021 Calo, 2002, [Nphe1,Arg14,Lys15] Nociceptin-NH2, a novel potent and selective antagonist of the nociceptin/orphanin FQ receptor, Br J Pharmacol, 136, 303, 10.1038/sj.bjp.0704706 Guerrini, 2005, N- and C-terminal modifications of nociceptin/orphanin FQ generate highly potent NOP receptor ligands, J Med Chem, 48, 1421, 10.1021/jm040106v Atherton, 1989 Varani, 1998, Nociceptin receptor binding in mouse forebrain membranes: thermodynamic characteristics and structure activity relationships, Br J Pharmacol, 125, 1485, 10.1038/sj.bjp.0702226 Calo, 1998, Structure-activity study of the nociceptin-(1–13)-NH2 N-terminal tetrapeptide and discovery of a nociceptin receptor antagonist, J Med Chem, 4, 3360, 10.1021/jm970805q Hughes, 1975, Effect of morphine on adrenergic transmission in the mouse vas deferens. Assessment of agonist and antagonist potencies of narcotic analgesics, Br J Pharmacol, 53, 371, 10.1111/j.1476-5381.1975.tb07373.x Jenkinson, 1995, International Union of Pharmacology Committee on receptor nomenclature and drug classification: XI. Recommendations on terms and symbols in quantitative pharmacology, Pharmacol Rev, 47, 255 Hruby, 2002, Designing peptide receptor agonists and antagonists, Nat Rev Drug Discov, 1, 847, 10.1038/nrd939 Schwyzer, 1977, ACTH: a short introductory review, Ann N Y Acad Sci, 297, 3, 10.1111/j.1749-6632.1977.tb41843.x Cowell, 2002, Design and synthesis of peptide antagonists and inverse agonists for G protein-coupled receptors, Methods Enzymol, 343, 49, 10.1016/S0076-6879(02)43127-8 Guerrini, 1997, Address and message sequences for the nociceptin receptor: a structure–activity study of nociceptin-(1–13)-peptide amide, J Med Chem, 40, 1789, 10.1021/jm970011b Klaudel, 2004, Solution conformational study of nociceptin and its 1–13 and 1–11 fragments using circular dichroism and two-dimensional NMR in conjunction with theoretical conformational analysis, J Pept Sci, 10, 678, 10.1002/psc.576 Orsini, 2005, The nociceptin pharmacophore site for opioid receptor binding derived from the NMR structure and bioactivity relationships, J Biol Chem, 280, 8134, 10.1074/jbc.M406405200 Salvadori, 1999, Structure activity studies on nociceptin/orphanin FQ: from full agonist, to partial agonist, to pure antagonist, Il Famaco, 54, 810, 10.1016/S0014-827X(99)00108-1 Carra, 2005, [(pF)Phe4,Arg14, Lys15]N/OFQ-NH2 (UFP-102), a highly potent and selective agonist of the nociceptin/orphanin FQ receptor, J Pharmacol Exp Ther, 312, 1114, 10.1124/jpet.104.077339 Reinscheid, 1996, Structure–activity relationship studies on the novel neuropeptide orphanin FQ, J Biol Chem, 271, 14163, 10.1074/jbc.271.24.14163 Chen, 2003, Design and parallel synthesis of piperidine libraries targeting the nociceptin (N/OFQ) receptor, Bioorg Med Chem Lett, 19, 3247, 10.1016/S0960-894X(03)00665-6 Guerrini, 2004, Nonpeptide/peptide chimeric ligands for the nociceptin/orphanin FQ receptor: design, synthesis and in vitro pharmacological activity, J Pept Res, 63, 477, 10.1111/j.1399-3011.2004.00157.x Topham, 1998, Molecular modeling of the ORL1 receptor and its complex with nociceptin, Protein Eng, 11, 1163, 10.1093/protein/11.12.1163 Mouledous, 2000, Functional inactivation of the nociceptin receptor by alanine substitution of glutamine 286 at the C terminus of transmembrane segment VI: evidence from a site-directed mutagenesis study of the ORL1 receptor transmembrane-binding domain, Mol Pharmacol, 57, 495, 10.1124/mol.57.3.495 Pogozheva, 1998, Opioid receptor three-dimensional structures from distance geometry calculations with hydrogen bonding constraints, Biophys J, 75, 612, 10.1016/S0006-3495(98)77552-6