Literature DB >> 29615341

A review of salvinorin analogs and their kappa-opioid receptor activity.

Jeremy J Roach1, Ryan A Shenvi2.   

Abstract

The plant metabolite salvinorin A potently and selectively agonizes the human kappa-opioid receptor, an emerging target for next-generation analgesics. Here we review analogs of the salvinorin chemotype and their effects on selectivity, affinity and potency. Extensive peripheral modifications using isolated salvinorin A have delivered a trove of SAR information. More deep-seated changes are now possible by advances in chemical synthesis.
Copyright © 2018 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  GPCR; Kappa-opioid; Opioid; Salvinorin; Terpenoid

Mesh:

Substances:

Year:  2018        PMID: 29615341      PMCID: PMC5912166          DOI: 10.1016/j.bmcl.2018.03.029

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


  80 in total

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3.  Modular Approach to pseudo-Neoclerodanes as Designer κ-Opioid Ligands.

Authors:  Alexander M Sherwood; Samuel E Williamson; Rachel S Crowley; Logan M Abbott; Victor W Day; Thomas E Prisinzano
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4.  Differential signaling properties at the kappa opioid receptor of 12-epi-salvinorin A and its analogues.

Authors:  Cécile Béguin; Justin Potuzak; Wei Xu; Lee-Yuan Liu-Chen; John M Streicher; Chad E Groer; Laura M Bohn; William A Carlezon; Bruce M Cohen
Journal:  Bioorg Med Chem Lett       Date:  2011-12-07       Impact factor: 2.823

5.  Studies toward the pharmacophore of salvinorin A, a potent kappa opioid receptor agonist.

Authors:  Thomas A Munro; Mark A Rizzacasa; Bryan L Roth; Beth A Toth; Feng Yan
Journal:  J Med Chem       Date:  2005-01-27       Impact factor: 7.446

6.  Pharmacokinetics of the plant-derived kappa-opioid hallucinogen salvinorin A in nonhuman primates.

Authors:  Matthew D Schmidt; Mark S Schmidt; Eduardo R Butelman; Wayne W Harding; Kevin Tidgewell; Daryl J Murry; Mary Jeanne Kreek; Thomas E Prisinzano
Journal:  Synapse       Date:  2005-12-01       Impact factor: 2.562

7.  Addressing Structural Flexibility at the A-Ring on Salvinorin A: Discovery of a Potent Kappa-Opioid Agonist with Enhanced Metabolic Stability.

Authors:  Alexander M Sherwood; Rachel Saylor Crowley; Kelly F Paton; Andrew Biggerstaff; Benjamin Neuenswander; Victor W Day; Bronwyn M Kivell; Thomas E Prisinzano
Journal:  J Med Chem       Date:  2017-04-19       Impact factor: 7.446

8.  Synthesis and biological evaluation of C-2 halogenated analogs of salvinorin A.

Authors:  David Y W Lee; Lu Yang; Wei Xu; Gang Deng; Lin Guo; Lee-Yuan Liu-Chen
Journal:  Bioorg Med Chem Lett       Date:  2010-08-05       Impact factor: 2.823

9.  An opioid agonist that does not induce mu-opioid receptor--arrestin interactions or receptor internalization.

Authors:  C E Groer; K Tidgewell; R A Moyer; W W Harding; R B Rothman; T E Prisinzano; L M Bohn
Journal:  Mol Pharmacol       Date:  2006-11-07       Impact factor: 4.436

10.  Development of an enzyme immunoassay using a monoclonal antibody against the psychoactive diterpenoid salvinorin A.

Authors:  Madan Kumar Paudel; Osamu Shirota; Kaori Sasaki-Tabata; Hiroyuki Tanaka; Setsuko Sekita; Satoshi Morimoto
Journal:  J Nat Prod       Date:  2013-08-29       Impact factor: 4.050

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1.  Plants with Anti-Addictive Potential.

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3.  Pleiotropic Effects of Kappa Opioid Receptor-Related Ligands in Non-human Primates.

Authors:  Mei-Chuan Ko; Stephen M Husbands
Journal:  Handb Exp Pharmacol       Date:  2020-12-04

4.  Clerodane furanoditerpenoids from the stems of Tinospora sinensis.

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Review 5.  Chemical syntheses of the salvinorin chemotype of KOR agonist.

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6.  6,5-Fused Ring, C2-Salvinorin Ester, Dual Kappa and Mu Opioid Receptor Agonists as Analgesics Devoid of Anxiogenic Effects.

Authors:  Nicholas S Akins; Nisha Mishra; Hannah M Harris; Narendar Dudhipala; Seong Jong Kim; Adam W Keasling; Soumyajit Majumdar; Jordan K Zjawiony; Jason J Paris; Nicole M Ashpole; Hoang V Le
Journal:  ChemMedChem       Date:  2022-02-10       Impact factor: 3.466

Review 7.  Pharmacokinetics and Pharmacodynamics of Salvinorin A and Salvia divinorum: Clinical and Forensic Aspects.

Authors:  Andreia Machado Brito-da-Costa; Diana Dias-da-Silva; Nelson G M Gomes; Ricardo Jorge Dinis-Oliveira; Áurea Madureira-Carvalho
Journal:  Pharmaceuticals (Basel)       Date:  2021-02-03

Review 8.  Natural Products for the Treatment of Pain: Chemistry and Pharmacology of Salvinorin A, Mitragynine, and Collybolide.

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Review 9.  Terpenoids, Cannabimimetic Ligands, beyond the Cannabis Plant.

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Review 10.  Development of Diphenethylamines as Selective Kappa Opioid Receptor Ligands and Their Pharmacological Activities.

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