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

被引：45
|
作者：
Roach, Jeremy J. [1 ]
Shenvi, Ryan A. [1 ]
机构：
[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2018年 / 28卷 / 09期
关键词：
Salvinorin; Terpenoid; Opioid; GPCR; Kappa-opioid; SALVIA-DIVINORUM; IN-VITRO; NEOCLERODANE DITERPENES; A ANALOGS; BIOLOGICAL EVALUATION; HALLUCINOGEN SALVINORIN; BIASED AGONISM; FURAN RING; POTENT; LIGANDS;
D O I：
10.1016/j.bmcl.2018.03.029
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
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. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1436 / 1445
页数：10
相关论文
共 50 条
  • [31] Design and structural validation of peptide-drug conjugate ligands of the kappa-opioid receptor
    Muratspahic, Edin
    Deibler, Kristine
    Han, Jianming
    Tomasevic, Natasa
    Jadhav, Kirtikumar B.
    Olive-Marti, Aina-Leonor
    Hochrainer, Nadine
    Hellinger, Roland
    Koehbach, Johannes
    Fay, Jonathan F.
    Rahman, Mohammad Homaidur
    Hegazy, Lamees
    Craven, Timothy W.
    Varga, Balazs R.
    Bhardwaj, Gaurav
    Appourchaux, Kevin
    Majumdar, Susruta
    Muttenthaler, Markus
    Hosseinzadeh, Parisa
    Craik, David J.
    Spetea, Mariana
    Che, Tao
    Baker, David
    Gruber, Christian W.
    NATURE COMMUNICATIONS, 2023, 14 (01)
  • [32] ANALYSIS OF THE ANTINOCICEPTIVE ACTIONS OF THE KAPPA-OPIOID AGONIST ENADOLINE (CI-977) IN NEONATAL AND ADULT-RATS - COMPARISON TO KAPPA-OPIOID RECEPTOR MESSENGER-RNA ONTOGENY
    MCLAUGHLIN, CR
    TAO, Q
    ABOOD, ME
    DRUG AND ALCOHOL DEPENDENCE, 1995, 38 (03) : 261 - 269
  • [33] Depletion of serotonin decreases the effects of the kappa-opioid receptor agonist U-69593 on cocaine-stimulated activity
    Zakharova, Elena
    Collins, Stephanie L.
    Aberg, Maria
    Kumar, Adarsh
    Fernandez, J. B.
    Izenwasser, Sari
    EUROPEAN JOURNAL OF PHARMACOLOGY, 2008, 586 (1-3) : 123 - 129
  • [34] Kappa opioid mediation of cannabinoid effects of the potent hallucinogen, salvinorin A, in rodents
    Walentiny, D. Matthew
    Vann, Robert E.
    Warner, Jonathan A.
    King, Lindsey S.
    Seltzman, Herbert H.
    Navarro, Hernan A.
    Twine, Charles E., Jr.
    Thomas, Brian F.
    Gilliam, Anne F.
    Gilmour, Brian P.
    Carroll, F. Ivy
    Wiley, Jenny L.
    PSYCHOPHARMACOLOGY, 2010, 210 (02) : 275 - 284
  • [35] A single injection of a novel kappa opioid receptor agonist salvinorin A attenuates the expression of cocaine-induced behavioral sensitization in rats
    Morani, Aashish S.
    Schenk, Susan
    Prisinzano, Thomas E.
    Kivell, Bronwyn Maree
    BEHAVIOURAL PHARMACOLOGY, 2012, 23 (02): : 162 - 170
  • [36] DISCRIMINATIVE STIMULUS EFFECTS OF SPIRADOLINE, A KAPPA-OPIOID AGONIST
    HOLTZMAN, SG
    COOK, L
    STEINFELS, GF
    PSYCHOPHARMACOLOGY, 1991, 105 (04) : 447 - 452
  • [37] Evaluation of the abuse potential of difelikefalin, a selective kappa-opioid receptor agonist, in recreational polydrug users
    Shram, Megan J.
    Spencer, Robert H.
    Qian, Jenny
    Munera, Catherine L.
    Lewis, Michael E.
    Henningfield, Jack E.
    Webster, Lynn
    Menzaghi, Frederique
    CTS-CLINICAL AND TRANSLATIONAL SCIENCE, 2022, 15 (02): : 535 - 547
  • [38] Antidepressive effects of the κ-opioid receptor agonist salvinorin A in a rat model of anhedonia
    Harden, Mitchell T.
    Smith, Staci E.
    Niehoff, Jennifer A.
    McCurdy, Christopher R.
    Taylor, George T.
    BEHAVIOURAL PHARMACOLOGY, 2012, 23 (07): : 710 - 715
  • [39] Design and synthesis of natural product-based ligands with high affinity to the kappa-opioid receptor
    Zjawiony, J. K.
    Polepally, P. R.
    Roth, B. L.
    Setola, V
    Vardy, E.
    PLANTA MEDICA, 2011, 77 (12) : 1243 - 1243
  • [40] Will peripherally restricted kappa-opioid receptor agonists (pKORAs) relieve pain with less opioid adverse effects and abuse potential?
    Albert-Vartanian, A.
    Boyd, M. R.
    Hall, A. L.
    Morgado, S. J.
    Nguyen, E.
    Nguyen, V. P. H.
    Patel, S. P.
    Russo, L. J.
    Shao, A. J.
    Raffa, R. B.
    JOURNAL OF CLINICAL PHARMACY AND THERAPEUTICS, 2016, 41 (04) : 371 - 382
12345