Literature DB >> 28885019

Sulfonium as a Surrogate for Ammonium: A New α7 Nicotinic Acetylcholine Receptor Partial Agonist with Desensitizing Activity.

Marta Quadri1,2, Clare Stokes2, Alican Gulsevin1, Ashley C J Felts3, Khalil A Abboud3, Roger L Papke2, Nicole A Horenstein1.   

Abstract

Weak partial agonists that promote a desensitized state of the α7 nicotinic acetylcholine receptor (nAChR) have been associated with anti-inflammatory effects. Exemplar compounds feature a tertiary or quaternary ammonium group. We report the synthesis, structure, and electrophysiological evaluation of 1-ethyl-4-phenylthiomorpholin-1-ium triflate, a weak partial agonist with a sulfonium isostere of the ammonium pharmacophore. These results offer new insights in understanding nAChR-ligand interactions and provide a new chemical space to target the α7 nAChR.

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Year:  2017        PMID： 28885019      PMCID： PMC5653211          DOI： 10.1021/acs.jmedchem.7b00875

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


  27 in total

1.  A novel positive allosteric modulator of the alpha7 neuronal nicotinic acetylcholine receptor: in vitro and in vivo characterization.

Authors:  Raymond S Hurst; Mihaly Hajós; Mario Raggenbass; Theron M Wall; Nicole R Higdon; Judy A Lawson; Karen L Rutherford-Root; Mitchell B Berkenpas; W E Hoffmann; David W Piotrowski; Vincent E Groppi; Geraldine Allaman; Roch Ogier; Sonia Bertrand; Daniel Bertrand; Stephen P Arneric
Journal:  J Neurosci       Date:  2005-04-27       Impact factor: 6.167

2.  Editorial: To channel or not to channel? Functioning of nicotinic acetylcholine receptors in leukocytes.

Authors:  Maryna V Skok
Journal:  J Leukoc Biol       Date:  2009-07       Impact factor: 4.962

3.  Identification and Characterization of a G Protein-binding Cluster in α7 Nicotinic Acetylcholine Receptors.

Authors:  Justin R King; Jacob C Nordman; Samuel P Bridges; Ming-Kuan Lin; Nadine Kabbani
Journal:  J Biol Chem       Date:  2015-06-18       Impact factor: 5.157

4.  Evaluation of the cholinomimetic actions of trimethylsulfonium, a compound present in the midgut gland of the sea hare Aplysia brasiliana (Gastropoda, Opisthobranchia).

Authors:  C M Kerchove; R P Markus; J C Freitas; L V Costa-Lotufo
Journal:  Braz J Med Biol Res       Date:  2002-04       Impact factor: 2.590

5.  Synthesis and pharmacological evaluation of sulfonium analogues of dopamine: nonclassical dopamine agonists.

Authors:  K Anderson; A Kuruvilla; N Uretsky; D D Miller
Journal:  J Med Chem       Date:  1981-06       Impact factor: 7.446

6.  The minimal pharmacophore for silent agonism of the α7 nicotinic acetylcholine receptor.

Authors:  Roger L Papke; Kinga Chojnacka; Nicole A Horenstein
Journal:  J Pharmacol Exp Ther       Date:  2014-07-02       Impact factor: 4.030

7.  Modulation of TNF release by choline requires alpha7 subunit nicotinic acetylcholine receptor-mediated signaling.

Authors:  William R Parrish; Mauricio Rosas-Ballina; Margot Gallowitsch-Puerta; Mahendar Ochani; Kanta Ochani; Li-Hong Yang; LaQueta Hudson; Xinchun Lin; Nirav Patel; Sarah M Johnson; Sangeeta Chavan; Richard S Goldstein; Christopher J Czura; Edmund J Miller; Yousef Al-Abed; Kevin J Tracey; Valentin A Pavlov
Journal:  Mol Med       Date:  2008 Sep-Oct       Impact factor: 6.354

8.  From ab initio quantum mechanics to molecular neurobiology: a cation-pi binding site in the nicotinic receptor.

Authors:  W Zhong; J P Gallivan; Y Zhang; L Li; H A Lester; D A Dougherty
Journal:  Proc Natl Acad Sci U S A       Date:  1998-10-13       Impact factor: 11.205

9.  Comparative pharmacology of rat and human alpha7 nAChR conducted with net charge analysis.

Authors:  Roger L Papke; Julia K Porter Papke
Journal:  Br J Pharmacol       Date:  2002-09       Impact factor: 8.739

10.  Nicotinic acetylcholine receptor alpha7 subunit is an essential regulator of inflammation.

Authors:  Hong Wang; Man Yu; Mahendar Ochani; Carol Ann Amella; Mahira Tanovic; Seenu Susarla; Jian Hua Li; Haichao Wang; Huan Yang; Luis Ulloa; Yousef Al-Abed; Christopher J Czura; Kevin J Tracey
Journal:  Nature       Date:  2002-12-22       Impact factor: 49.962
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  6 in total

1.  Allosteric Agonism of α7 Nicotinic Acetylcholine Receptors: Receptor Modulation Outside the Orthosteric Site.

Authors:  Alican Gulsevin; Roger L Papke; Clare Stokes; Sumanta Garai; Ganesh A Thakur; Marta Quadri; Nicole A Horenstein
Journal:  Mol Pharmacol       Date:  2019-04-03       Impact factor: 4.436

2.  Anti-inflammatory Silent Agonists.

Authors:  Nicole A Horenstein; Roger L Papke
Journal:  ACS Med Chem Lett       Date:  2017-09-26       Impact factor: 4.345

3.  Selective Agonists and Antagonists of α9 Versus α7 Nicotinic Acetylcholine Receptors.

Authors:  Roger L Papke; Hina Andleeb; Clare Stokes; Marta Quadri; Nicole A Horenstein
Journal:  ACS Chem Neurosci       Date:  2022-02-15       Impact factor: 5.780

4.  Novel 5-(quinuclidin-3-ylmethyl)-1,2,4-oxadiazoles to investigate the activation of the α7 nicotinic acetylcholine receptor subtype: Synthesis and electrophysiological evaluation.

Authors:  Marta Quadri; Almin Silnović; Carlo Matera; Nicole A Horenstein; Clare Stokes; Marco De Amici; Roger L Papke; Clelia Dallanoce
Journal:  Eur J Med Chem       Date:  2018-10-11       Impact factor: 6.514

5.  Design, synthesis, and electrophysiological evaluation of NS6740 derivatives: Exploration of the structure-activity relationship for alpha7 nicotinic acetylcholine receptor silent activation.

Authors:  Maria Chiara Pismataro; Nicole A Horenstein; Clare Stokes; Marta Quadri; Marco De Amici; Roger L Papke; Clelia Dallanoce
Journal:  Eur J Med Chem       Date:  2020-07-28       Impact factor: 6.514

Review 6.  Therapeutic Targeting of α7 Nicotinic Acetylcholine Receptors.

Authors:  Roger L Papke; Nicole A Horenstein
Journal:  Pharmacol Rev       Date:  2021-07       Impact factor: 18.923
  6 in total

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