Literature DB >> 21536445

Synthesis and characterization of selective dopamine D₂ receptor ligands using aripiprazole as the lead compound.

Suwanna Vangveravong1, Zhanbin Zhang, Michelle Taylor, Melissa Bearden, Jinbin Xu, Jinquan Cui, Wei Wang, Robert R Luedtke, Robert H Mach.   

Abstract

A series of compounds structurally related to aripiprazole (1), an atypical antipsychotic and antidepressant used clinically for the treatment of n class="Disease">schizophrenia, bipolar disorder, and depression, have been prepared and evaluated for affinity at D(₂-like) dopamine receptors. These compounds also share structural elements with the classical D(₂-like) dopamine receptor antagonists, haloperidol, N-methylspiperone, domperidone and benperidol. Two new compounds, 7-(4-(4-(2-methoxyphenyl)piperazin-1-yl)butoxy)-3,4-dihydroquinolin-2(1H)-one oxalate (6) and 7-(4-(4-(2-(2-fluoroethoxy)phenyl)piperazin-1-yl)butoxy)-3,4-dihydroquinolin-2(1H)-one oxalate (7) were found to (a) bind to the D₂ receptor subtype with high affinity (K(i) values < 0.3 nM), (b) exhibit >50-fold D₂ versus D₃ receptor binding selectivity and (c) be partial agonists at both the D₂ and D₃ receptor subtype.
Copyright © 2011 Elsevier Ltd. All rights reserved.

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Year:  2011        PMID: 21536445      PMCID: PMC3118479          DOI: 10.1016/j.bmc.2011.04.021

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN: 0968-0896            Impact factor:   3.641


  39 in total

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Authors:  Philip H Elsinga; Kentaro Hatano; Kiichi Ishiwata
Journal:  Curr Med Chem       Date:  2006       Impact factor: 4.530

2.  High-affinity states of human brain dopamine D2/3 receptors imaged by the agonist [11C]-(+)-PHNO.

Authors:  Matthäus Willeit; Nathalie Ginovart; Shitij Kapur; Sylvain Houle; Doug Hussey; Philip Seeman; Alan A Wilson
Journal:  Biol Psychiatry       Date:  2005-12-20       Impact factor: 13.382

3.  [(3)H]4-(Dimethylamino)-N-[4-(4-(2-methoxyphenyl)piperazin- 1-yl)butyl]benzamide, a selective radioligand for dopamine D(3) receptors. I. In vitro characterization.

Authors:  Jinbin Xu; Wenhua Chu; Zhude Tu; Lynne A Jones; Robert R Luedtke; Joel S Perlmutter; Mark A Mintun; Robert H Mach
Journal:  Synapse       Date:  2009-09       Impact factor: 2.562

4.  PET imaging of dopamine D2 receptors during chronic cocaine self-administration in monkeys.

Authors:  Michael A Nader; Drake Morgan; H Donald Gage; Susan H Nader; Tonya L Calhoun; Nancy Buchheimer; Richard Ehrenkaufer; Robert H Mach
Journal:  Nat Neurosci       Date:  2006-07-09       Impact factor: 24.884

5.  [3H]N-[4-(3,4-dihydro-6,7-dimethoxyisoquinolin-2(1H)-yl)butyl]-2-methoxy-5-methylbenzamide: a novel sigma-2 receptor probe.

Authors:  Jinbin Xu; Zhude Tu; Lynne A Jones; Suwanna Vangveravong; Kenneth T Wheeler; Robert H Mach
Journal:  Eur J Pharmacol       Date:  2005-11-10       Impact factor: 4.432

6.  Synthesis and characterization of selective dopamine D2 receptor antagonists.

Authors:  Suwanna Vangveravong; Elizabeth McElveen; Michelle Taylor; Jinbin Xu; Zhude Tu; Robert R Luedtke; Robert H Mach
Journal:  Bioorg Med Chem       Date:  2005-11-08       Impact factor: 3.641

7.  Further evaluation of the carbon11-labeled D(2/3) agonist PET radiotracer PHNO: reproducibility in tracer characteristics and characterization of extrastriatal binding.

Authors:  Alice Egerton; Ella Hirani; Rabia Ahmad; David R Turton; Diana Brickute; Lula Rosso; Oliver D Howes; Sajinder K Luthra; Paul M Grasby
Journal:  Synapse       Date:  2010-04       Impact factor: 2.562

8.  Positron emission tomography imaging of amphetamine-induced dopamine release in the human cortex: a comparative evaluation of the high affinity dopamine D2/3 radiotracers [11C]FLB 457 and [11C]fallypride.

Authors:  Rajesh Narendran; W Gordon Frankle; N Scott Mason; Eugenii A Rabiner; Roger N Gunn; Graham E Searle; Shivangi Vora; Maralee Litschge; Steve Kendro; Thomas B Cooper; Chester A Mathis; Marc Laruelle
Journal:  Synapse       Date:  2009-06       Impact factor: 2.562

9.  Dopamine D3 receptor selective ligands with varying intrinsic efficacies at adenylyl cyclase inhibition and mitogenic signaling pathways.

Authors:  Michelle Taylor; Peter Grundt; Suzy A Griffin; Amy Hauck Newman; Robert R Luedtke
Journal:  Synapse       Date:  2010-03       Impact factor: 2.562

10.  4-[omega-[4-arylpiperazin-1-yl]alkoxy]phenyl)imidazo[1,2-a]pyridine derivatives: fluorescent high-affinity dopamine D3 receptor ligands as potential probes for receptor visualization.

Authors:  Marcello Leopoldo; Enza Lacivita; Elena Passafiume; Marialessandra Contino; Nicola A Colabufo; Francesco Berardi; Roberto Perrone
Journal:  J Med Chem       Date:  2007-09-12       Impact factor: 7.446

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  10 in total

Review 1.  Advances and challenges in the search for D2 and D3 dopamine receptor-selective compounds.

Authors:  Amy E Moritz; R Benjamin Free; David R Sibley
Journal:  Cell Signal       Date:  2017-07-14       Impact factor: 4.315

2.  Comparison of the binding and functional properties of two structurally different D2 dopamine receptor subtype selective compounds.

Authors:  Robert R Luedtke; Yogesh Mishra; Qi Wang; Suzy A Griffin; Cathy Bell-Horner; Michelle Taylor; Suwanna Vangveravong; Glenn H Dillon; Ren-Qi Huang; David E Reichert; Robert H Mach
Journal:  ACS Chem Neurosci       Date:  2012-10-12       Impact factor: 4.418

3.  Molecular determinants of selectivity and efficacy at the dopamine D3 receptor.

Authors:  Amy Hauck Newman; Thijs Beuming; Ashwini K Banala; Prashant Donthamsetti; Katherine Pongetti; Alex LaBounty; Benjamin Levy; Jianjing Cao; Mayako Michino; Robert R Luedtke; Jonathan A Javitch; Lei Shi
Journal:  J Med Chem       Date:  2012-06-07       Impact factor: 7.446

4.  BiasNet: A Model to Predict Ligand Bias Toward GPCR Signaling.

Authors:  Jason E Sanchez; Govinda B Kc; Julian Franco; William J Allen; Jesus David Garcia; Suman Sirimulla
Journal:  J Chem Inf Model       Date:  2021-08-16       Impact factor: 6.162

5.  Structure-functional selectivity relationship studies of β-arrestin-biased dopamine D₂ receptor agonists.

Authors:  Xin Chen; Maria F Sassano; Lianyou Zheng; Vincent Setola; Meng Chen; Xu Bai; Stephen V Frye; William C Wetsel; Bryan L Roth; Jian Jin
Journal:  J Med Chem       Date:  2012-08-13       Impact factor: 7.446

6.  Positron emission tomography imaging of dopamine D2 receptors using a highly selective radiolabeled D2 receptor partial agonist.

Authors:  Jinbin Xu; Suwanna Vangveravong; Shihong Li; Jinda Fan; Lynne A Jones; Jinquan Cui; Ruike Wang; Zhude Tu; Wenhua Chu; Joel S Perlmutter; Robert H Mach
Journal:  Neuroimage       Date:  2013-01-17       Impact factor: 6.556

Review 7.  11C- and 18F-Radiotracers for In Vivo Imaging of the Dopamine System: Past, Present and Future.

Authors:  Michael R Kilbourn
Journal:  Biomedicines       Date:  2021-01-22

8.  Dopamine D3 receptor antagonist reveals a cryptic pocket in aminergic GPCRs.

Authors:  Noelia Ferruz; Stefan Doerr; Michelle A Vanase-Frawley; Yaozhong Zou; Xiaomin Chen; Eric S Marr; Robin T Nelson; Bethany L Kormos; Travis T Wager; Xinjun Hou; Anabella Villalobos; Simone Sciabola; Gianni De Fabritiis
Journal:  Sci Rep       Date:  2018-01-17       Impact factor: 4.379

9.  Ligand with Two Modes of Interaction with the Dopamine D2 Receptor-An Induced-Fit Mechanism of Insurmountable Antagonism.

Authors:  Richard Ågren; Hugo Zeberg; Tomasz Maciej Stępniewski; R Benjamin Free; Sean W Reilly; Robert R Luedtke; Peter Århem; Francisco Ciruela; David R Sibley; Robert H Mach; Jana Selent; Johanna Nilsson; Kristoffer Sahlholm
Journal:  ACS Chem Neurosci       Date:  2020-09-15       Impact factor: 4.418

10.  Synthesis and In Vitro Evaluation of Novel Dopamine Receptor D2 3,4-dihydroquinolin-2(1H)-one Derivatives Related to Aripiprazole.

Authors:  Radomir Juza; Kristyna Stefkova; Wim Dehaen; Alena Randakova; Tomas Petrasek; Iveta Vojtechova; Tereza Kobrlova; Lenka Pulkrabkova; Lubica Muckova; Marko Mecava; Lukas Prchal; Eva Mezeiova; Kamil Musilek; Ondrej Soukup; Jan Korabecny
Journal:  Biomolecules       Date:  2021-08-24
  10 in total

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