Literature DB >> 24090443

Expeditious synthesis, enantiomeric resolution, and enantiomer functional characterization of (4-(4-bromophenyl)-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinoline-8-sulfonamide (4BP-TQS): an allosteric agonist-positive allosteric modulator of α7 nicotinic acetylcholine receptors.

Ganesh A Thakur1, Abhijit R Kulkarni, Jeffrey R Deschamps, Roger L Papke.   

Abstract

An expeditious microwave-assisted synthesis of 4BP-TQS, its enantiomeric separation, and their functional evaluation is reported. Electrophysiological characterization in Xenopus oocytes revealed that activity exclusively resided in the (+)-enantiomer 1b (GAT107) and (-)-enantiomer 1a did not affect its activity when coapplied. X-ray crystallography studies revealed the absolute stereochemistry of 1b to be 3aR,4S,9bS. 1b represents the most potent ago-PAM of α7 nAChRs available to date and is considered for further in vivo evaluation.

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Year:  2013        PMID： 24090443      PMCID： PMC3933094          DOI： 10.1021/jm401267t

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


  23 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

Review 2.  Structural and functional diversity of native brain neuronal nicotinic receptors.

Authors:  Cecilia Gotti; Francesco Clementi; Alice Fornari; Annalisa Gaimarri; Stefania Guiducci; Irene Manfredi; Milena Moretti; Patrizia Pedrazzi; Luca Pucci; Michele Zoli
Journal:  Biochem Pharmacol       Date:  2009-05-27       Impact factor: 5.858

Review 3.  Advances in the chemistry of tetrahydroquinolines.

Authors:  Vellaisamy Sridharan; Padmakar A Suryavanshi; J Carlos Menéndez
Journal:  Chem Rev       Date:  2011-08-10       Impact factor: 60.622

4.  Investigation of the molecular mechanism of the α7 nicotinic acetylcholine receptor positive allosteric modulator PNU-120596 provides evidence for two distinct desensitized states.

Authors:  Dustin K Williams; Jingyi Wang; Roger L Papke
Journal:  Mol Pharmacol       Date:  2011-09-01       Impact factor: 4.436

Review 5.  Positive allosteric modulators as an approach to nicotinic acetylcholine receptor-targeted therapeutics: advantages and limitations.

Authors:  Dustin K Williams; Jingyi Wang; Roger L Papke
Journal:  Biochem Pharmacol       Date:  2011-05-14       Impact factor: 5.858

Review 6.  Targeting the nicotinic alpha7 acetylcholine receptor to enhance cognition in disease.

Authors:  Tanya L Wallace; Richard H P Porter
Journal:  Biochem Pharmacol       Date:  2011-07-02       Impact factor: 5.858

7.  A series of α7 nicotinic acetylcholine receptor allosteric modulators with close chemical similarity but diverse pharmacological properties.

Authors:  JasKiran K Gill; Persis Dhankher; Tom D Sheppard; Emanuele Sher; Neil S Millar
Journal:  Mol Pharmacol       Date:  2012-02-10       Impact factor: 4.436

8.  Effects of α7 positive allosteric modulators in murine inflammatory and chronic neuropathic pain models.

Authors:  Kelen Freitas; Sudeshna Ghosh; F Ivy Carroll; Aron H Lichtman; M Imad Damaj
Journal:  Neuropharmacology       Date:  2012-10-16       Impact factor: 5.250

9.  Activation and desensitization of nicotinic alpha7-type acetylcholine receptors by benzylidene anabaseines and nicotine.

Authors:  Roger L Papke; William R Kem; Ferenc Soti; Gretchen Y López-Hernández; Nicole A Horenstein
Journal:  J Pharmacol Exp Ther       Date:  2009-02-17       Impact factor: 4.030

10.  Distinct profiles of alpha7 nAChR positive allosteric modulation revealed by structurally diverse chemotypes.

Authors:  Jens Halvard Grønlien; Monika Håkerud; Hilde Ween; Kirsten Thorin-Hagene; Clark A Briggs; Murali Gopalakrishnan; John Malysz
Journal:  Mol Pharmacol       Date:  2007-06-12       Impact factor: 4.436
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  22 in total

1.  Critical Molecular Determinants of α7 Nicotinic Acetylcholine Receptor Allosteric Activation: SEPARATION OF DIRECT ALLOSTERIC ACTIVATION AND POSITIVE ALLOSTERIC MODULATION.

Authors:  Nicole A Horenstein; Roger L Papke; Abhijit R Kulkarni; Ganesh U Chaturbhuj; Clare Stokes; Khan Manther; Ganesh A Thakur
Journal:  J Biol Chem       Date:  2016-01-07       Impact factor: 5.157

2.  Heteromeric Neuronal Nicotinic Acetylcholine Receptors with Mutant β Subunits Acquire Sensitivity to α7-Selective Positive Allosteric Modulators.

Authors:  Clare Stokes; Sumanta Garai; Abhijit R Kulkarni; Lucas N Cantwell; Colleen M Noviello; Ryan E Hibbs; Nicole A Horenstein; Khalil A Abboud; Ganesh A Thakur; Roger L Papke
Journal:  J Pharmacol Exp Ther       Date:  2019-06-07       Impact factor: 4.030

3.  Macroscopic and Microscopic Activation of α7 Nicotinic Acetylcholine Receptors by the Structurally Unrelated Allosteric Agonist-Positive Allosteric Modulators (ago-PAMs) B-973B and GAT107.

Authors:  Marta Quadri; Sumanta Garai; Ganesh A Thakur; Clare Stokes; Alican Gulsevin; Nicole A Horenstein; Roger L Papke
Journal:  Mol Pharmacol       Date:  2018-10-22       Impact factor: 4.436

4.  B-973, a Novel α7 nAChR Ago-PAM: Racemic and Asymmetric Synthesis, Electrophysiological Studies, and in Vivo Evaluation.

Authors:  Sumanta Garai; Krishnamohan S Raja; Roger L Papke; Jeffrey R Deschamps; M Imad Damaj; Ganesh A Thakur
Journal:  ACS Med Chem Lett       Date:  2018-10-11       Impact factor: 4.345

5.  The α7 nicotinic receptor dual allosteric agonist and positive allosteric modulator GAT107 reverses nociception in mouse models of inflammatory and neuropathic pain.

Authors:  Deniz Bagdas; Jenny L Wilkerson; Abhijit Kulkarni; Wisam Toma; Shakir AlSharari; Zulfiye Gul; Aron H Lichtman; Roger L Papke; Ganesh A Thakur; M Imad Damaj
Journal:  Br J Pharmacol       Date:  2016-07-18       Impact factor: 8.739

6.  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

Review 7.  Nicotinic acetylcholine receptors in neuropathic and inflammatory pain.

Authors:  Arik J Hone; J Michael McIntosh
Journal:  FEBS Lett       Date:  2017-10-27       Impact factor: 4.124

8.  Persistent activation of α7 nicotinic ACh receptors associated with stable induction of different desensitized states.

Authors:  Roger L Papke; Clare Stokes; M Imad Damaj; Ganesh A Thakur; Khan Manther; Millet Treinin; Deniz Bagdas; Abhijit R Kulkarni; Nicole A Horenstein
Journal:  Br J Pharmacol       Date:  2017-06-08       Impact factor: 8.739

9.  The activity of GAT107, an allosteric activator and positive modulator of α7 nicotinic acetylcholine receptors (nAChR), is regulated by aromatic amino acids that span the subunit interface.

Authors:  Roger L Papke; Nicole A Horenstein; Abhijit R Kulkarni; Clare Stokes; Lu W Corrie; Cheol-Young Maeng; Ganesh A Thakur
Journal:  J Biol Chem       Date:  2013-12-20       Impact factor: 5.157

10.  Allosterically Potentiated α7 Nicotinic Acetylcholine Receptors: Reduced Calcium Permeability and Current-Independent Control of Intracellular Calcium.

Authors:  Douglas R Miller; Habibeh Khoshbouei; Sumanta Garai; Lucas N Cantwell; Clare Stokes; Ganesh Thakur; Roger L Papke
Journal:  Mol Pharmacol       Date:  2020-10-05       Impact factor: 4.436
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