Literature DB >> 28011222

Benzylideneoxymorphone: A new lead for development of bifunctional mu/delta opioid receptor ligands.

Jason R Healy1, Padmavani Bezawada2, Nicholas W Griggs3, Andrea L Devereaux4, Rae R Matsumoto5, John R Traynor3, Andrew Coop2, Christopher W Cunningham6.   

Abstract

Opioid analgesic tolerance remains a considerable drawback to chronic pain management. The finding that concomitant administration of delta opioid receptor (DOR) antagonists attenuates the development of tolerance to mu opioid receptor (MOR) agonists has led to interest in producing bifunctional MOR agonist/DOR antagonist ligands. Herein, we present 7-benzylideneoxymorphone (6, UMB 246) displaying MOR partial agonist/DOR antagonist activity, representing a new lead for designing bifunctional MOR/DOR ligands.
Copyright © 2016 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  Analgesic tolerance; Benzylideneoxymorphone; Delta opioid receptor; Mu opioid receptor; Oxymorphone

Mesh：

Substances：

Year:  2016        PMID： 28011222      PMCID： PMC5404377          DOI： 10.1016/j.bmcl.2016.11.057

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


  19 in total

Review 1.  Opioid ligands with mixed mu/delta opioid receptor interactions: an emerging approach to novel analgesics.

Authors:  Subramaniam Ananthan
Journal:  AAPS J       Date:  2006-03-10       Impact factor: 4.009

2.  Quantitative conformationally sampled pharmacophore for delta opioid ligands: reevaluation of hydrophobic moieties essential for biological activity.

Authors:  Denzil Bernard; Andrew Coop; Alexander D MacKerell
Journal:  J Med Chem       Date:  2007-03-17       Impact factor: 7.446

Review 3.  Incidence, prevalence, and management of opioid bowel dysfunction.

Authors:  M Pappagallo
Journal:  Am J Surg       Date:  2001-11       Impact factor: 2.565

Review 4.  Bivalent ligands and the message-address concept in the design of selective opioid receptor antagonists.

Authors:  P S Portoghese
Journal:  Trends Pharmacol Sci       Date:  1989-06       Impact factor: 14.819

5.  14-Alkoxy- and 14-acyloxypyridomorphinans: μ agonist/δ antagonist opioid analgesics with diminished tolerance and dependence side effects.

Authors:  Subramaniam Ananthan; Surendra K Saini; Christina M Dersch; Heng Xu; Nicholas McGlinchey; Denise Giuvelis; Edward J Bilsky; Richard B Rothman
Journal:  J Med Chem       Date:  2012-09-27       Impact factor: 7.446

6.  The opioid mu agonist/delta antagonist DIPP-NH(2)[Psi] produces a potent analgesic effect, no physical dependence, and less tolerance than morphine in rats.

Authors:  P W Schiller; M E Fundytus; L Merovitz; G Weltrowska; T M Nguyen; C Lemieux; N N Chung; T J Coderre
Journal:  J Med Chem       Date:  1999-09-09       Impact factor: 7.446

7.  Synthesis, modeling, and pharmacological evaluation of UMB 425, a mixed μ agonist/δ antagonist opioid analgesic with reduced tolerance liabilities.

Authors:  Jason R Healy; Padmavani Bezawada; Jihyun Shim; Jace W Jones; Maureen A Kane; Alexander D MacKerell; Andrew Coop; Rae R Matsumoto
Journal:  ACS Chem Neurosci       Date:  2013-06-11       Impact factor: 4.418

Review 8.  Buprenorphine maintenance versus placebo or methadone maintenance for opioid dependence.

Authors:  R P Mattick; J Kimber; C Breen; M Davoli
Journal:  Cochrane Database Syst Rev       Date:  2008-04-16

9.  Effects of N-Substitutions on the Tetrahydroquinoline (THQ) Core of Mixed-Efficacy μ-Opioid Receptor (MOR)/δ-Opioid Receptor (DOR) Ligands.

Authors:  Aubrie A Harland; Aaron M Bender; Nicholas W Griggs; Chao Gao; Jessica P Anand; Irina D Pogozheva; John R Traynor; Emily M Jutkiewicz; Henry I Mosberg
Journal:  J Med Chem       Date:  2016-05-16       Impact factor: 7.446

10.  7-Arylidenenaltrexones as selective delta1 opioid receptor antagonists.

Authors:  S Ohkawa; P S Portoghese
Journal:  J Med Chem       Date:  1998-10-08       Impact factor: 7.446
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  2 in total

1.  Differential Effects of a Novel Opioid Ligand UTA1003 on Antinociceptive Tolerance and Motor Behaviour.

Authors:  Alok K Paul; Krystel L Woolley; Mohammed Rahmatullah; Polrat Wilairatana; Jason A Smith; Nuri Gueven; Nikolas Dietis
Journal:  Pharmaceuticals (Basel)       Date:  2022-06-24

2.  Peripheral antinociceptive effects of a bifunctional μ and δ opioid receptor ligand in rat model of inflammatory bladder pain.

Authors:  Maia Terashvili; Bhavana Talluri; Watchareepohn Palangmonthip; Kenneth A Iczkowski; Patrick Sanvanson; Bidyut K Medda; Banani Banerjee; Christopher W Cunningham; Jyoti N Sengupta
Journal:  Neuropharmacology       Date:  2021-07-10       Impact factor: 5.273
  2 in total

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