Literature DB >> 22642365

Structure-activity relationship study of N⁶-(2-(4-(1H-Indol-5-yl)piperazin-1-yl)ethyl)-N⁶-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine analogues: development of highly selective D3 dopamine receptor agonists along with a highly potent D2/D3 agonist and their pharmacological characterization.

Mark Johnson1, Tamara Antonio, Maarten E A Reith, Aloke K Dutta.   

Abstract

In our effort to develop multifunctional drugs against Parkinson's disease, a structure-activity-relationship study was carried out based on our hybrid molecular template targeting n class="Gene">D2/D3 receptors. Competitive binding with [(3)H]spiroperidol was used to evaluate affinity (K(i)) of test compounds. Functional activity of selected compounds in stimulating [(35)S]GTPγS binding was assessed in CHO cells expressing either human D2 or D3 receptors. Our results demonstrated development of highly selective compounds for D3 receptor (for (-)-40K(i), D3 = 1.84 nM, D2/D3 = 583.2; for (-)-45K(i), D3 = 1.09 nM, D2/D3 = 827.5). Functional data identified (-)-40 (EC(50), D2 = 114 nM, D3 = 0.26 nM, D2/D3 = 438) as one of the highest D3 selective agonists known to date. In addition, high affinity, nonselective D3 agonist (-)-19 (EC(50), D2 = 2.96 nM and D3 = 1.26 nM) was also developed. Lead compounds with antioxidant activity were evaluated using an in vivo PD animal model.

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Year:  2012        PMID: 22642365      PMCID: PMC3386472          DOI: 10.1021/jm300268s

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


  43 in total

Review 1.  Dopamine receptors--physiological understanding to therapeutic intervention potential.

Authors:  G Emilien; J M Maloteaux; M Geurts; K Hoogenberg; S Cragg
Journal:  Pharmacol Ther       Date:  1999-11       Impact factor: 12.310

2.  3,4-Dihydroxyphenylalanine and 5-hydroxytryptophan as reserpine antagonists.

Authors:  A CARLSSON; M LINDQVIST; T MAGNUSSON
Journal:  Nature       Date:  1957-11-30       Impact factor: 49.962

3.  Cloning of the gene for a human dopamine D5 receptor with higher affinity for dopamine than D1.

Authors:  R K Sunahara; H C Guan; B F O'Dowd; P Seeman; L G Laurier; G Ng; S R George; J Torchia; H H Van Tol; H B Niznik
Journal:  Nature       Date:  1991-04-18       Impact factor: 49.962

4.  Investigation of various N-heterocyclic substituted piperazine versions of 5/7-{[2-(4-aryl-piperazin-1-yl)-ethyl]-propyl-amino}-5,6,7,8-tetrahydro-naphthalen-2-ol: effect on affinity and selectivity for dopamine D3 receptor.

Authors:  Dennis A Brown; Manoj Mishra; Suhong Zhang; Swati Biswas; Ingrid Parrington; Tamara Antonio; Maarten E A Reith; Aloke K Dutta
Journal:  Bioorg Med Chem       Date:  2009-04-19       Impact factor: 3.641

5.  Distribution of dopamine D3 receptor expressing neurons in the human forebrain: comparison with D2 receptor expressing neurons.

Authors:  E V Gurevich; J N Joyce
Journal:  Neuropsychopharmacology       Date:  1999-01       Impact factor: 7.853

6.  Dopamine D₂/D₃ agonists with potent iron chelation, antioxidant and neuroprotective properties: potential implication in symptomatic and neuroprotective treatment of Parkinson's disease.

Authors:  Sanjib Gogoi; Tamara Antonio; Subramanian Rajagopalan; Maarten Reith; Julie Andersen; Aloke K Dutta
Journal:  ChemMedChem       Date:  2011-05-12       Impact factor: 3.466

7.  Reaction of melatonin and related indoles with hydroxyl radicals: EPR and spin trapping investigations.

Authors:  Z Matuszak; K Reszka; C F Chignell
Journal:  Free Radic Biol Med       Date:  1997       Impact factor: 7.376

Review 8.  Molecular diversity of the dopamine receptors.

Authors:  O Civelli; J R Bunzow; D K Grandy
Journal:  Annu Rev Pharmacol Toxicol       Date:  1993       Impact factor: 13.820

9.  Dopamine-dependent neurotoxicity of alpha-synuclein: a mechanism for selective neurodegeneration in Parkinson disease.

Authors:  Jin Xu; Shyan-Yuan Kao; Frank J S Lee; Weihong Song; Lee-Way Jin; Bruce A Yankner
Journal:  Nat Med       Date:  2002-06       Impact factor: 53.440

10.  Synthesis and biological characterization of novel hybrid 7-[[2-(4-phenyl-piperazin-1-yl)-ethyl]-propyl-amino]-5,6,7,8-tetrahydro-naphthalen-2-ol and their heterocyclic bioisosteric analogues for dopamine D2 and D3 receptors.

Authors:  Aloke K Dutta; Sylesh K Venkataraman; Xiang-Shu Fei; Rohit Kolhatkar; Shijun Zhang; Maarten E A Reith
Journal:  Bioorg Med Chem       Date:  2004-08-15       Impact factor: 3.641

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  20 in total

1.  Multicomponent Synthesis and Biological Evaluation of a Piperazine-Based Dopamine Receptor Ligand Library.

Authors:  Mattia Stucchi; Peter Gmeiner; Harald Huebner; Giulia Rainoldi; Alessandro Sacchetti; Alessandra Silvani; Giordano Lesma
Journal:  ACS Med Chem Lett       Date:  2015-06-23       Impact factor: 4.345

2.  Efficacy of Hybrid Tetrahydrobenzo[d]thiazole Based Aryl Piperazines D-264 and D-301 at D₂ and D₃ Receptors.

Authors:  Maarten E A Reith; Aloke K Dutta; Dana E Selley; Juan Zhen; Tamara Antonio; Joanna C Jacob; David K Grandy
Journal:  Neurochem Res       Date:  2015-12-31       Impact factor: 3.996

Review 3.  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

4.  D-512, a novel dopamine D2/3 receptor agonist, demonstrates greater anti-Parkinsonian efficacy than ropinirole in Parkinsonian rats.

Authors:  David Lindenbach; Banibrata Das; Melissa M Conti; Samantha M Meadows; Aloke K Dutta; Christopher Bishop
Journal:  Br J Pharmacol       Date:  2017-08-11       Impact factor: 8.739

5.  Interaction of D₃ preferring agonist (-)-N⁶-(2-(4-(biphenyl-4-yl)piperazin-1-yl)ethyl)-N⁶-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine (D-264) with cloned human D₂L, D₂S, and D₃ receptors: potent stimulation of mitogen-activated protein kinases and G protein-coupled inward rectifier potassium channels.

Authors:  Eldo V Kuzhikandathil; Samantha Cote; Soumava Santra; Aloke K Dutta
Journal:  Naunyn Schmiedebergs Arch Pharmacol       Date:  2012-11-20       Impact factor: 3.000

6.  Modification of agonist binding moiety in hybrid derivative 5/7-{[2-(4-aryl-piperazin-1-yl)-ethyl]-propyl-amino}-5,6,7,8-tetrahydro-naphthalen-1-ol/-2-amino versions: impact on functional activity and selectivity for dopamine D2/D3 receptors.

Authors:  Bhaskar Gopishetty; Suhong Zhang; Prashant S Kharkar; Tamara Antonio; Maarten Reith; Aloke K Dutta
Journal:  Bioorg Med Chem       Date:  2013-04-01       Impact factor: 3.641

7.  The high-affinity D2/D3 agonist D512 protects PC12 cells from 6-OHDA-induced apoptotic cell death and rescues dopaminergic neurons in the MPTP mouse model of Parkinson's disease.

Authors:  Mrudang Shah; Subramanian Rajagopalan; Liping Xu; Chandrashekhar Voshavar; Yevgeniya Shurubor; Flint Beal; Julie K Andersen; Aloke K Dutta
Journal:  J Neurochem       Date:  2014-06-21       Impact factor: 5.372

8.  Discovery, Optimization, and Characterization of ML417: A Novel and Highly Selective D3 Dopamine Receptor Agonist.

Authors:  Amy E Moritz; R Benjamin Free; Warren S Weiner; Emmanuel O Akano; Disha Gandhi; Ara Abramyan; Thomas M Keck; Marc Ferrer; Xin Hu; Noel Southall; Joseph Steiner; Jeffrey Aubé; Lei Shi; Kevin J Frankowski; David R Sibley
Journal:  J Med Chem       Date:  2020-05-12       Impact factor: 7.446

9.  D-512 and D-440 as novel multifunctional dopamine agonists: characterization of neuroprotection properties and evaluation of in vivo efficacy in a Parkinson's disease animal model.

Authors:  Soumava Santra; Liping Xu; Mrudang Shah; Mark Johnson; Aloke Dutta
Journal:  ACS Chem Neurosci       Date:  2013-08-20       Impact factor: 4.418

10.  Multifunctional D2/D3 agonist D-520 with high in vivo efficacy: modulator of toxicity of alpha-synuclein aggregates.

Authors:  Gyan Modi; Chandrashekhar Voshavar; Sanjib Gogoi; Mrudang Shah; Tamara Antonio; Maarten E A Reith; Aloke K Dutta
Journal:  ACS Chem Neurosci       Date:  2014-07-09       Impact factor: 4.418

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