Literature DB >> 22247793

Synthesis and evaluation of dimeric derivatives of 5-HT(2A) receptor (5-HT(2A)R) antagonist M-100907.

Matthew J Shashack1, Kathryn A Cunningham, Patricia K Seitz, Andrew McGinnis, Thressa Smith, Cheryl S Watson, Scott R Gilbertson.   

Abstract

It is now well accepted that at least some serotonin receptors exist in dimeric and oligmeric forms. The linking of receptor ligands has been shown to have potential in the development of selective agonists and antagonists for traditionally refractive receptors. Here we report the development of a dimeric version of the known 5-HT(2A)R antagonist, M-100907. Derivatives of M-100907 were synthesized to determine an appropriate site for the linker connection. Then, homodimers with polyether linkers of different lengths were functionally tested in a bioassay to determine the optimal linker length. Attachment at the catechol of M-100907 with linkers between 12 and 18 atoms in length proved to be optimal.

Entities:  

Year:  2011        PMID： 22247793      PMCID： PMC3254110          DOI： 10.1021/cn200077q

Source DB:  PubMed          Journal:  ACS Chem Neurosci        ISSN： 1948-7193            Impact factor:   4.418


  25 in total

Review 1.  Multivalent-based drug design applied to serotonin 5-HT(4) receptor oligomers.

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2.  G protein activation by serotonin type 4 receptor dimers: evidence that turning on two protomers is more efficient.

Authors:  Lucie P Pellissier; Gaël Barthet; Florence Gaven; Elisabeth Cassier; Eric Trinquet; Jean-Philippe Pin; Philippe Marin; Aline Dumuis; Joël Bockaert; Jean-Louis Banères; Sylvie Claeysen
Journal:  J Biol Chem       Date:  2011-01-19       Impact factor: 5.157

3.  1-(1-phenethylpiperidin-4-yl)-1-phenylethanols as potent and highly selective 5-HT2A antagonists.

Authors:  Timo Heinrich; Henning Böttcher; Helmut Prücher; Rudolf Gottschlich; Karl-August Ackermann; Christoph van Amsterdam
Journal:  ChemMedChem       Date:  2006-02       Impact factor: 3.466

Review 4.  Molecular, pharmacological and functional diversity of 5-HT receptors.

Authors:  Daniel Hoyer; Jason P Hannon; Graeme R Martin
Journal:  Pharmacol Biochem Behav       Date:  2002-04       Impact factor: 3.533

5.  Inhibition of serotonin 5-hydroxytryptamine2c receptor function through heterodimerization: receptor dimers bind two molecules of ligand and one G-protein.

Authors:  Katharine Herrick-Davis; Ellinor Grinde; Timothy J Harrigan; Joseph E Mazurkiewicz
Journal:  J Biol Chem       Date:  2005-09-29       Impact factor: 5.157

Review 6.  5-hydroxytryptamine (5-HT) receptor ligands.

Authors:  Sean L Kitson
Journal:  Curr Pharm Des       Date:  2007       Impact factor: 3.116

7.  Molecular dynamics simulation of the heterodimeric mGluR2/5HT(2A) complex. An atomistic resolution study of a potential new target in psychiatric conditions.

Authors:  Agostino Bruno; Antonio Entrena Guadix; Gabriele Costantino
Journal:  J Chem Inf Model       Date:  2009-06       Impact factor: 4.956

8.  Signal transduction differences between 5-hydroxytryptamine type 2A and type 2C receptor systems.

Authors:  K A Berg; W P Clarke; C Sailstad; A Saltzman; S Maayani
Journal:  Mol Pharmacol       Date:  1994-09       Impact factor: 4.436

9.  Synthesis and in vitro affinities of various MDL 100907 derivatives as potential 18F-radioligands for 5-HT2A receptor imaging with PET.

Authors:  Matthias M Herth; Vasko Kramer; Markus Piel; Mikael Palner; Patrick J Riss; Gitte M Knudsen; Frank Rösch
Journal:  Bioorg Med Chem       Date:  2009-03-14       Impact factor: 3.641

10.  Blockade of the serotonin 5-HT2A receptor suppresses cue-evoked reinstatement of cocaine-seeking behavior in a rat self-administration model.

Authors:  B A Nic Dhonnchadha; R G Fox; S J Stutz; K C Rice; K A Cunningham
Journal:  Behav Neurosci       Date:  2009-04       Impact factor: 1.912
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  10 in total

1.  Celebrating serotonin.

Authors:  Anne M Andrews
Journal:  ACS Chem Neurosci       Date:  2012-09-19       Impact factor: 4.418

Review 2.  Serotonin 5-HT2 receptor interactions with dopamine function: implications for therapeutics in cocaine use disorder.

Authors:  Leonard L Howell; Kathryn A Cunningham
Journal:  Pharmacol Rev       Date:  2015       Impact factor: 25.468

3.  Synthesis and Structure-Activity Relationships of Tool Compounds Based on WAY163909, a 5-HT2C Receptor Agonist.

Authors:  Ying-Chu Chen; Rachel M Hartley; Noelle C Anastasio; Kathryn A Cunningham; Scott R Gilbertson
Journal:  ACS Chem Neurosci       Date:  2017-04-19       Impact factor: 4.418

4.  Novel Bivalent 5-HT2A Receptor Antagonists Exhibit High Affinity and Potency in Vitro and Efficacy in Vivo.

Authors:  Claudia A Soto; Matthew J Shashack; Robert G Fox; Marcy J Bubar; Kenner C Rice; Cheryl S Watson; Kathryn A Cunningham; Scott R Gilbertson; Noelle C Anastasio
Journal:  ACS Chem Neurosci       Date:  2017-11-21       Impact factor: 4.418

5.  Synergism between a serotonin 5-HT2A receptor (5-HT2AR) antagonist and 5-HT2CR agonist suggests new pharmacotherapeutics for cocaine addiction.

Authors:  Kathryn A Cunningham; Noelle C Anastasio; Robert G Fox; Sonja J Stutz; Marcy J Bubar; Sarah E Swinford; Cheryl S Watson; Scott R Gilbertson; Kenner C Rice; Sharon Rosenzweig-Lipson; F Gerard Moeller
Journal:  ACS Chem Neurosci       Date:  2012-08-11       Impact factor: 4.418

6.  Peptide inhibitors disrupt the serotonin 5-HT2C receptor interaction with phosphatase and tensin homolog to allosterically modulate cellular signaling and behavior.

Authors:  Noelle C Anastasio; Scott R Gilbertson; Marcy J Bubar; Anton Agarkov; Sonja J Stutz; Yowjiun Jeng; Nicole M Bremer; Thressa D Smith; Robert G Fox; Sarah E Swinford; Patricia K Seitz; Marc N Charendoff; John W Craft; Fernanda M Laezza; Cheryl S Watson; James M Briggs; Kathryn A Cunningham
Journal:  J Neurosci       Date:  2013-01-23       Impact factor: 6.167

Review 7.  Functional significance of serotonin receptor dimerization.

Authors:  Katharine Herrick-Davis
Journal:  Exp Brain Res       Date:  2013-06-29       Impact factor: 1.972

8.  Quantitative changes in intracellular calcium and extracellular-regulated kinase activation measured in parallel in CHO cells stably expressing serotonin (5-HT) 5-HT2A or 5-HT2C receptors.

Authors:  Patricia K Seitz; Nicole M Bremer; Andrew G McGinnis; Kathryn A Cunningham; Cheryl S Watson
Journal:  BMC Neurosci       Date:  2012-03-07       Impact factor: 3.288

Review 9.  ¹⁸F-labeled silicon-based fluoride acceptors: potential opportunities for novel positron emitting radiopharmaceuticals.

Authors:  Vadim Bernard-Gauthier; Carmen Wängler; Esther Schirrmacher; Alexey Kostikov; Klaus Jurkschat; Bjoern Wängler; Ralf Schirrmacher
Journal:  Biomed Res Int       Date:  2014-07-24       Impact factor: 3.411

10.  Suppression of cocaine relapse-like behaviors upon pimavanserin and lorcaserin co-administration.

Authors:  Noelle C Anastasio; Dennis J Sholler; Robert G Fox; Sonja J Stutz; Christina R Merritt; James M Bjork; F Gerard Moeller; Kathryn A Cunningham
Journal:  Neuropharmacology       Date:  2020-02-14       Impact factor: 5.250
  10 in total

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