Literature DB >> 21866885

Structural determinants of opioid and NOP receptor activity in derivatives of buprenorphine.

Gerta Cami-Kobeci1, Willma E Polgar, Taline V Khroyan, Lawrence Toll, Stephen M Husbands.   

Abstract

The unique pharmacological profile of buprenorphine has led to its considerable success as an analgesic and as a treatment agent for drug abuse. Activation of nociceptin/orphanin FQ peptide (NOP) receptors has been postulated to account for certain aspects of buprenorphine's behavioral profile. In order to investigate the role of NOP activation further, a series of buprenorphine analogues has been synthesized with the aim of increasing affinity for the NOP receptor. Binding and functional assay data on these new compounds indicate that the area around C20 in the orvinols is key to NOP receptor activity, with several compounds displaying higher affinity than buprenorphine. One compound, 1b, was found to be a mu opioid receptor partial agonist of comparable efficacy to buprenorphine but with higher efficacy at NOP receptors.

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Year:  2011        PMID： 21866885      PMCID： PMC3188691          DOI： 10.1021/jm2003238

Source DB:  PubMed          Journal:  J Med Chem        ISSN： 0022-2623            Impact factor:   7.446


  26 in total

1.  Comparison of pharmacological activities of buprenorphine and norbuprenorphine: norbuprenorphine is a potent opioid agonist.

Authors:  P Huang; G B Kehner; A Cowan; L Y Liu-Chen
Journal:  J Pharmacol Exp Ther       Date:  2001-05       Impact factor: 4.030

2.  Structural determinants of efficacy for kappa opioid receptors in the orvinol series: 7,7-spiro analogues of buprenorphine.

Authors:  S M Husbands; J W Lewis
Journal:  J Med Chem       Date:  2000-01-27       Impact factor: 7.446

Review 3.  Animal models of nociception.

Authors:  D Le Bars; M Gozariu; S W Cadden
Journal:  Pharmacol Rev       Date:  2001-12       Impact factor: 25.468

4.  The first universal opioid ligand, (2S)-2-[(5R,6R,7R,14S)-N-cyclopropylmethyl-4,5-epoxy-6,14-ethano-3-hydroxy-6-methoxymorphinan-7-yl]-3,3-dimethylpentan-2-ol (BU08028): characterization of the in vitro profile and in vivo behavioral effects in mouse models of acute pain and cocaine-induced reward.

Authors:  Taline V Khroyan; Willma E Polgar; Gerta Cami-Kobeci; Stephen M Husbands; Nurulain T Zaveri; Lawrence Toll
Journal:  J Pharmacol Exp Ther       Date:  2010-12-21       Impact factor: 4.030

5.  Agonistic effects of the opioid buprenorphine on the nociceptin/OFQ receptor.

Authors:  P Bloms-Funke; C Gillen; A J Schuettler; S Wnendt
Journal:  Peptides       Date:  2000-07       Impact factor: 3.750

6.  In vitro and in vivo pharmacological characterization of J-113397, a potent and selective non-peptidyl ORL1 receptor antagonist.

Authors:  S Ozaki; H Kawamoto; Y Itoh; M Miyaji; T Azuma; D Ichikawa; H Nambu; T Iguchi; Y Iwasawa; H Ohta
Journal:  Eur J Pharmacol       Date:  2000-08-18       Impact factor: 4.432

7.  Characterization of opiates, neuroleptics, and synthetic analogs at ORL1 and opioid receptors.

Authors:  N Zaveri; W E Polgar; C M Olsen; A B Kelson; P Grundt; J W Lewis; L Toll
Journal:  Eur J Pharmacol       Date:  2001-09-28       Impact factor: 4.432

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

Review 9.  Opioid ligands having delayed long-term antagonist activity: potential pharmacotherapies for opioid abuse.

Authors:  Stephen M Husbands; John W Lewis
Journal:  Mini Rev Med Chem       Date:  2003-03       Impact factor: 3.862

10.  Buprenorphine-induced antinociception is mediated by mu-opioid receptors and compromised by concomitant activation of opioid receptor-like receptors.

Authors:  Kabirullah Lutfy; Shoshana Eitan; Camron D Bryant; Yu C Yang; Nazli Saliminejad; Wendy Walwyn; Brigitte L Kieffer; Hiroshi Takeshima; F Ivy Carroll; Nigel T Maidment; Christopher J Evans
Journal:  J Neurosci       Date:  2003-11-12       Impact factor: 6.167
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  21 in total

1.  BU10038 as a safe opioid analgesic with fewer side-effects after systemic and intrathecal administration in primates.

Authors:  Norikazu Kiguchi; Huiping Ding; Gerta Cami-Kobeci; Devki D Sukhtankar; Paul W Czoty; Heather B DeLoid; Fang-Chi Hsu; Lawrence Toll; Stephen M Husbands; Mei-Chuan Ko
Journal:  Br J Anaesth       Date:  2019-03-01       Impact factor: 9.166

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.  Effects of stimulation of mu opioid and nociceptin/orphanin FQ peptide (NOP) receptors on alcohol drinking in rhesus monkeys.

Authors:  Shawn M Flynn; Phillip M Epperly; April T Davenport; Gerta Cami-Kobeci; Stephen M Husbands; Mei-Chuan Ko; Paul W Czoty
Journal:  Neuropsychopharmacology       Date:  2019-04-10       Impact factor: 7.853

4.  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

5.  Abuse Liability, Anti-Nociceptive, and Discriminative Stimulus Properties of IBNtxA.

Authors:  Ariful Islam; Mohammad Atiqur Rahman; Megan B Brenner; Allamar Moore; Alyssa Kellmyer; Harley M Buechler; Frank DiGiorgio; Vincent R Verchio; Laura McCracken; Mousumi Sumi; Robert Hartley; Joseph R Lizza; Gustavo Moura-Letts; Bradford D Fischer; Thomas M Keck
Journal:  ACS Pharmacol Transl Sci       Date:  2020-07-27

Review 6.  Nociceptin/Orphanin FQ Peptide Receptor-Related Ligands as Novel Analgesics.

Authors:  Norikazu Kiguchi; Huiping Ding; Shiroh Kishioka; Mei-Chuan Ko
Journal:  Curr Top Med Chem       Date:  2020       Impact factor: 3.295

7.  BU08073 a buprenorphine analogue with partial agonist activity at μ-receptors in vitro but long-lasting opioid antagonist activity in vivo in mice.

Authors:  T V Khroyan; J Wu; W E Polgar; G Cami-Kobeci; N Fotaki; S M Husbands; L Toll
Journal:  Br J Pharmacol       Date:  2014-11-05       Impact factor: 8.739

8.  Novel mixed NOP/MOP agonist BU08070 alleviates pain and inhibits gastrointestinal motility in mouse models mimicking diarrhea-predominant irritable bowel syndrome symptoms.

Authors:  Marta Sobczak; Gerta Cami-Kobeci; Maciej Sałaga; Stephen M Husbands; Jakub Fichna
Journal:  Eur J Pharmacol       Date:  2014-05-06       Impact factor: 4.432

Review 9.  The therapeutic potential of nociceptin/orphanin FQ receptor agonists as analgesics without abuse liability.

Authors:  Ann P Lin; Mei-Chuan Ko
Journal:  ACS Chem Neurosci       Date:  2012-11-06       Impact factor: 4.418

10.  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
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