Literature DB >> 32930582

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

Soumen Chakraborty1,2, Susruta Majumdar1,2.   

Abstract

Pain remains a very pervasive problem throughout medicine. Classical pain management is achieved through the use of opiates belonging to the mu opioid receptor (MOR) class, which have significant side effects that hinder their utility. Pharmacologists have been trying to develop opioids devoid of side effects since the isolation of morphine from papaver somniferum, more commonly known as opium by Sertürner in 1804. The natural products salvinorin A, mitragynine, and collybolide represent three nonmorphinan natural product-based targets, which are potent selective agonists of opioid receptors, and emerging next-generation analgesics. In this work, we review the phytochemistry and medicinal chemistry efforts on these templates and their effects on affinity, selectivity, analgesic actions, and a myriad of other opioid-receptor-related behavioral effects.

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Year:  2020        PMID: 32930582      PMCID: PMC7982354          DOI: 10.1021/acs.biochem.0c00629

Source DB:  PubMed          Journal:  Biochemistry        ISSN: 0006-2960            Impact factor:   3.162


  156 in total

1.  New procedure to mask the 2,3-pi bond of the indole nucleus and its application to the preparation of potent opioid receptor agonists with a Corynanthe skeleton.

Authors:  Hiromitsu Takayama; Kaori Misawa; Naoki Okada; Hayato Ishikawa; Mariko Kitajima; Yoshio Hatori; Toshihiko Murayama; Sumphan Wongseripipatana; Kimihito Tashima; Kenjiro Matsumoto; Syunji Horie
Journal:  Org Lett       Date:  2006-12-07       Impact factor: 6.005

2.  Total synthesis of the hallucinogenic neoclerodane diterpenoid salvinorin A.

Authors:  Masato Nozawa; Yuhki Suka; Takashi Hoshi; Toshio Suzuki; Hisahiro Hagiwara
Journal:  Org Lett       Date:  2008-03-01       Impact factor: 6.005

3.  Synthesis and in vitro pharmacological studies of new C(2) modified salvinorin A analogues.

Authors:  David Y W Lee; Vishnu V R Karnati; Minsheng He; Lee-Yuan Liu-Chen; Leelakrishna Kondaveti; Zhongze Ma; Yulin Wang; Yong Chen; Cecile Beguin; William A Carlezon; Bruce Cohen
Journal:  Bioorg Med Chem Lett       Date:  2005-08-15       Impact factor: 2.823

4.  New neoclerodane diterpenoids isolated from the leaves of Salvia divinorum and their binding affinities for human kappa opioid receptors.

Authors:  David Y W Lee; Zhongze Ma; Lee-Yuan Liu-Chen; Yulin Wang; Yong Chen; William A Carlezon; Bruce Cohen
Journal:  Bioorg Med Chem       Date:  2005-10-01       Impact factor: 3.641

5.  Antinociceptive effects of herkinorin, a MOP receptor agonist derived from salvinorin A in the formalin test in rats: new concepts in mu opioid receptor pharmacology: from a symposium on new concepts in mu-opioid pharmacology.

Authors:  Kenneth Lamb; Kevin Tidgewell; Denise S Simpson; Laura M Bohn; Thomas E Prisinzano
Journal:  Drug Alcohol Depend       Date:  2011-11-26       Impact factor: 4.492

Review 6.  Kappa opioids and the modulation of pain.

Authors:  Bronwyn Kivell; Thomas E Prisinzano
Journal:  Psychopharmacology (Berl)       Date:  2010-04-07       Impact factor: 4.530

7.  A facile method for the preparation of deuterium labeled salvinorin A: synthesis of [2,2,2-2H3]-salvinorin A.

Authors:  Kevin Tidgewell; Wayne W Harding; Mark Schmidt; Kenneth G Holden; Daryl J Murry; Thomas E Prisinzano
Journal:  Bioorg Med Chem Lett       Date:  2004-10-18       Impact factor: 2.823

8.  Synthetic and Receptor Signaling Explorations of the Mitragyna Alkaloids: Mitragynine as an Atypical Molecular Framework for Opioid Receptor Modulators.

Authors:  Andrew C Kruegel; Madalee M Gassaway; Abhijeet Kapoor; András Váradi; Susruta Majumdar; Marta Filizola; Jonathan A Javitch; Dalibor Sames
Journal:  J Am Chem Soc       Date:  2016-05-18       Impact factor: 15.419

9.  Salvinorins D-F, new neoclerodane diterpenoids from Salvia divinorum, and an improved method for the isolation of salvinorin A.

Authors:  Thomas A Munro; Mark A Rizzacasa
Journal:  J Nat Prod       Date:  2003-05       Impact factor: 4.050

10.  Investigation of the Adrenergic and Opioid Binding Affinities, Metabolic Stability, Plasma Protein Binding Properties, and Functional Effects of Selected Indole-Based Kratom Alkaloids.

Authors:  Samuel Obeng; Shyam H Kamble; Morgan E Reeves; Luis F Restrepo; Avi Patel; Mira Behnke; Nelson J-Y Chear; Surash Ramanathan; Abhisheak Sharma; Francisco León; Takato Hiranita; Bonnie A Avery; Lance R McMahon; Christopher R McCurdy
Journal:  J Med Chem       Date:  2019-12-27       Impact factor: 7.446

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  17 in total

1.  Clerodane furanoditerpenoids from the stems of Tinospora sinensis.

Authors:  Jun-Sheng Zhang; De-Feng Xu; Yin-Yin Wang; Ren-Fen Ma; Hua Zhang
Journal:  Arch Pharm Res       Date:  2022-04-27       Impact factor: 4.946

2.  Oxidative Metabolism as a Modulator of Kratom's Biological Actions.

Authors:  Soumen Chakraborty; Rajendra Uprety; Samuel T Slocum; Takeshi Irie; Valerie Le Rouzic; Xiaohai Li; Lisa L Wilson; Brittany Scouller; Amy F Alder; Andrew C Kruegel; Michael Ansonoff; Andras Varadi; Shainnel O Eans; Amanda Hunkele; Abdullah Allaoa; Sanjay Kalra; Jin Xu; Ying Xian Pan; John Pintar; Bronwyn M Kivell; Gavril W Pasternak; Michael D Cameron; Jay P McLaughlin; Dalibor Sames; Susruta Majumdar
Journal:  J Med Chem       Date:  2021-11-16       Impact factor: 7.446

Review 3.  Strategies towards safer opioid analgesics-A review of old and upcoming targets.

Authors:  Balazs R Varga; John M Streicher; Susruta Majumdar
Journal:  Br J Pharmacol       Date:  2021-11-26       Impact factor: 9.473

4.  Synthesis and Pharmacology of a Novel μ-δ Opioid Receptor Heteromer-Selective Agonist Based on the Carfentanyl Template.

Authors:  Abdelfattah Faouzi; Rajendra Uprety; Ivone Gomes; Nicolas Massaly; Attila I Keresztes; Valerie Le Rouzic; Achla Gupta; Tiffany Zhang; Hye Jean Yoon; Michael Ansonoff; Abdullah Allaoa; Ying Xian Pan; John Pintar; Jose A Morón; John M Streicher; Lakshmi A Devi; Susruta Majumdar
Journal:  J Med Chem       Date:  2020-11-10       Impact factor: 7.446

5.  Controlling opioid receptor functional selectivity by targeting distinct subpockets of the orthosteric site.

Authors:  Rajendra Uprety; Tao Che; Saheem A Zaidi; Steven G Grinnell; Balázs R Varga; Abdelfattah Faouzi; Samuel T Slocum; Abdullah Allaoa; András Varadi; Melissa Nelson; Sarah M Bernhard; Elizaveta Kulko; Valerie Le Rouzic; Shainnel O Eans; Chloe A Simons; Amanda Hunkele; Joan Subrath; Ying Xian Pan; Jonathan A Javitch; Jay P McLaughlin; Bryan L Roth; Gavril W Pasternak; Vsevolod Katritch; Susruta Majumdar
Journal:  Elife       Date:  2021-02-08       Impact factor: 8.140

6.  Predicted Mode of Binding to and Allosteric Modulation of the μ-Opioid Receptor by Kratom's Alkaloids with Reported Antinociception In Vivo.

Authors:  Yuchen Zhou; Steven Ramsey; Davide Provasi; Amal El Daibani; Kevin Appourchaux; Soumen Chakraborty; Abhijeet Kapoor; Tao Che; Susruta Majumdar; Marta Filizola
Journal:  Biochemistry       Date:  2020-12-04       Impact factor: 3.162

7.  Physiological dependence to mitragynine indicated by a rapid cross-dependence procedure with heroin-dependent mice.

Authors:  Kai Yue; Jonathan L Katz; Xiji Shu
Journal:  Psychopharmacology (Berl)       Date:  2022-02-02       Impact factor: 4.530

8.  A Novel Mitragynine Analog with Low-Efficacy Mu Opioid Receptor Agonism Displays Antinociception with Attenuated Adverse Effects.

Authors:  Soumen Chakraborty; Jeffrey F DiBerto; Abdelfattah Faouzi; Sarah M Bernhard; Anna M Gutridge; Steven Ramsey; Yuchen Zhou; Davide Provasi; Nitin Nuthikattu; Rahul Jilakara; Melissa N F Nelson; Wesley B Asher; Shainnel O Eans; Lisa L Wilson; Satyanarayana M Chintala; Marta Filizola; Richard M van Rijn; Elyssa B Margolis; Bryan L Roth; Jay P McLaughlin; Tao Che; Dalibor Sames; Jonathan A Javitch; Susruta Majumdar
Journal:  J Med Chem       Date:  2021-09-10       Impact factor: 8.039

9.  Site selective C-H functionalization of Mitragyna alkaloids reveals a molecular switch for tuning opioid receptor signaling efficacy.

Authors:  Srijita Bhowmik; Juraj Galeta; Václav Havel; Melissa Nelson; Abdelfattah Faouzi; Benjamin Bechand; Mike Ansonoff; Tomas Fiala; Amanda Hunkele; Andrew C Kruegel; John E Pintar; Susruta Majumdar; Jonathan A Javitch; Dalibor Sames
Journal:  Nat Commun       Date:  2021-06-22       Impact factor: 14.919

10.  Kratom Alkaloids as Probes for Opioid Receptor Function: Pharmacological Characterization of Minor Indole and Oxindole Alkaloids from Kratom.

Authors:  Soumen Chakraborty; Rajendra Uprety; Amal E Daibani; Valerie L Rouzic; Amanda Hunkele; Kevin Appourchaux; Shainnel O Eans; Nitin Nuthikattu; Rahul Jilakara; Lisa Thammavong; Gavril W Pasternak; Ying-Xian Pan; Jay P McLaughlin; Tao Che; Susruta Majumdar
Journal:  ACS Chem Neurosci       Date:  2021-07-02       Impact factor: 5.780

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