Literature DB >> 23623415

Designing bifunctional NOP receptor-mu opioid receptor ligands from NOP receptor-selective scaffolds. Part I.

Nurulain T Zaveri1, Faming Jiang, Cris Olsen, Willma E Polgar, Lawrence Toll.   

Abstract

The nociceptin receptor (NOP) and its endogenous agonist, nociceptin/orphanin FQ (N/OFQ), members of the opioid receptor and peptide families respectively, modulate the pharmacological effects of classical opioids, particularly opioid-induced reward and nociception. We hypothesized that compounds containing both NOP and opioid receptor activity in a single molecule may have useful pharmacological profiles as non-addicting analgesics or as drug abuse medications. We report here our forays into the structure-activity relationships for discovering 'bifunctional' NOP-mu opioid receptor (MOP) ligands, starting from our NOP-selective scaffolds. This initial SAR suggests pharmacophoric elements that may be modified to modulate/increase opioid affinity, while maintaining high affinity for the NOP receptor, to result in potent bifunctional small-molecule NOP/MOP ligands.
Copyright © 2013 Elsevier Ltd. All rights reserved.

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Year:  2013        PMID： 23623415      PMCID： PMC3651809          DOI： 10.1016/j.bmcl.2013.03.101

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  39 in total

1.  Discovery of the first 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).

Authors:  H Kawamoto; S Ozaki; Y Itoh; M Miyaji; S Arai; H Nakashima; T Kato; H Ohta; Y Iwasawa
Journal:  J Med Chem       Date:  1999-12-16       Impact factor: 7.446

2.  High-affinity, non-peptide agonists for the ORL1 (orphanin FQ/nociceptin) receptor.

Authors:  S Röver; G Adam; A M Cesura; G Galley; F Jenck; F J Monsma; J Wichmann; F M Dautzenberg
Journal:  J Med Chem       Date:  2000-04-06       Impact factor: 7.446

Review 3.  Tissue distribution of the opioid receptor-like (ORL1) receptor.

Authors:  C Mollereau; L Mouledous
Journal:  Peptides       Date:  2000-07       Impact factor: 3.750

4.  Nociceptin differentially affects morphine-induced dopamine release from the nucleus accumbens and nucleus caudate in rats.

Authors:  A Di Giannuario; S Pieretti
Journal:  Peptides       Date:  2000-07       Impact factor: 3.750

5.  4-Aminoquinolines: novel nociceptin antagonists with analgesic activity.

Authors:  H Shinkai; T Ito; T Iida; Y Kitao; H Yamada; I Uchida
Journal:  J Med Chem       Date:  2000-11-30       Impact factor: 7.446

Review 6.  The molecular and behavioral pharmacology of the orphanin FQ/nociceptin peptide and receptor family.

Authors:  J S Mogil; G W Pasternak
Journal:  Pharmacol Rev       Date:  2001-09       Impact factor: 25.468

7.  Synthesis of (1S,3aS)-8-(2,3,3a,4,5, 6-hexahydro-1H-phenalen-1-yl)-1-phenyl-1,3,8-triaza-spiro[4. 5]decan-4-one, a potent and selective orphanin FQ (OFQ) receptor agonist with anxiolytic-like properties.

Authors:  J Wichmann; G Adam; S Röver; M Hennig; M Scalone; A M Cesura; F M Dautzenberg; F Jenck
Journal:  Eur J Med Chem       Date:  2000-09       Impact factor: 6.514

8.  Modification of nociception and morphine tolerance by the selective opiate receptor-like orphan receptor antagonist (-)-cis-1-methyl-7-[[4-(2,6-dichlorophenyl)piperidin-1-yl]methyl]-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ol (SB-612111).

Authors:  Paola F Zaratin; Giuseppe Petrone; Massimo Sbacchi; Martine Garnier; Claudia Fossati; Paola Petrillo; Silvio Ronzoni; Giuseppe A M Giardina; Mark A Scheideler
Journal:  J Pharmacol Exp Ther       Date:  2003-10-30       Impact factor: 4.030

9.  Roles of μ-opioid receptors and nociceptin/orphanin FQ peptide receptors in buprenorphine-induced physiological responses in primates.

Authors:  Colette M Cremeans; Erin Gruley; Donald J Kyle; Mei-Chuan Ko
Journal:  J Pharmacol Exp Ther       Date:  2012-06-28       Impact factor: 4.030

10.  A novel series of piperidin-4-yl-1,3-dihydroindol-2-ones as agonist and antagonist ligands at the nociceptin receptor.

Authors:  Nurulain T Zaveri; Faming Jiang; Cris M Olsen; Jeffrey R Deschamps; Damon Parrish; Willma Polgar; Lawrence Toll
Journal:  J Med Chem       Date:  2004-06-03       Impact factor: 7.446
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  14 in total

1.  Designing bifunctional NOP receptor-mu opioid receptor ligands from NOP-receptor selective scaffolds. Part II.

Authors:  V Blair Journigan; Willma E Polgar; Taline V Khroyan; Nurulain T Zaveri
Journal:  Bioorg Med Chem       Date:  2014-03-05       Impact factor: 3.641

2.  Structure-Based SAR in the Design of Selective or Bifunctional Nociceptin (NOP) Receptor Agonists.

Authors:  Michael E Meyer; Arpit Doshi; Dennis Yasuda; Nurulain T Zaveri
Journal:  AAPS J       Date:  2021-05-11       Impact factor: 4.009

3.  A bifunctional nociceptin and mu opioid receptor agonist is analgesic without opioid side effects in nonhuman primates.

Authors:  Huiping Ding; Norikazu Kiguchi; Dennis Yasuda; Pankaj R Daga; Willma E Polgar; James J Lu; Paul W Czoty; Shiroh Kishioka; Nurulain T Zaveri; Mei-Chuan Ko
Journal:  Sci Transl Med       Date:  2018-08-29       Impact factor: 17.956

Review 4.  Central N/OFQ-NOP Receptor System in Pain Modulation.

Authors:  Norikazu Kiguchi; Huiping Ding; Mei-Chuan Ko
Journal:  Adv Pharmacol       Date:  2015-12-17

5.  A novel orvinol analog, BU08028, as a safe opioid analgesic without abuse liability in primates.

Authors:  Huiping Ding; Paul W Czoty; Norikazu Kiguchi; Gerta Cami-Kobeci; Devki D Sukhtankar; Michael A Nader; Stephen M Husbands; Mei-Chuan Ko
Journal:  Proc Natl Acad Sci U S A       Date:  2016-08-29       Impact factor: 11.205

6.  Supraspinal actions of nociceptin/orphanin FQ, morphine and substance P in regulating pain and itch in non-human primates.

Authors:  H Ding; K Hayashida; T Suto; D D Sukhtankar; M Kimura; V Mendenhall; M C Ko
Journal:  Br J Pharmacol       Date:  2015-04-24       Impact factor: 8.739

7.  Quantitative Signaling and Structure-Activity Analyses Demonstrate Functional Selectivity at the Nociceptin/Orphanin FQ Opioid Receptor.

Authors:  Steven D Chang; S Wayne Mascarella; Skylar M Spangler; Vsevolod V Gurevich; Hernan A Navarro; F Ivy Carroll; Michael R Bruchas
Journal:  Mol Pharmacol       Date:  2015-07-01       Impact factor: 4.436

Review 8.  Targeting multiple opioid receptors - improved analgesics with reduced side effects?

Authors:  Thomas Günther; Pooja Dasgupta; Anika Mann; Elke Miess; Andrea Kliewer; Sebastian Fritzwanker; Ralph Steinborn; Stefan Schulz
Journal:  Br J Pharmacol       Date:  2017-05-26       Impact factor: 8.739

9.  Bifunctional Peptide-Based Opioid Agonist-Nociceptin Antagonist Ligands for Dual Treatment of Acute and Neuropathic Pain.

Authors:  Karel Guillemyn; Joanna Starnowska; Camille Lagard; Jolanta Dyniewicz; Ewelina Rojewska; Joanna Mika; Nga N Chung; Valérie Utard; Piotr Kosson; Andrzej W Lipkowski; Lucie Chevillard; Pol Arranz-Gibert; Meritxell Teixidó; Bruno Megarbane; Dirk Tourwé; Frédéric Simonin; Barbara Przewlocka; Peter W Schiller; Steven Ballet
Journal:  J Med Chem       Date:  2016-04-14       Impact factor: 7.446

10.  Attenuated G protein signaling and minimal receptor phosphorylation as a biochemical signature of low side-effect opioid analgesics.

Authors:  Pooja Dasgupta; Anika Mann; Willma E Polgar; Rainer K Reinscheid; Nurulain T Zaveri; Stefan Schulz
Journal:  Sci Rep       Date:  2022-05-03       Impact factor: 4.996
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