Literature DB >> 24944746

Novel and high affinity fluorescent ligands for the serotonin transporter based on (s)-citalopram.

Vivek Kumar1, Troels Rahbek-Clemmensen2, Christian B Billesbølle2, Trine Nygaard Jorgensen2, Ulrik Gether2, Amy Hauck Newman1.   

Abstract

Novel rhodamine-labeled ligands, based on (S)-citalopram, were synthesized and evaluated for uptake inhibition at the human serotonin, dopamine, and norepinephrine transporters (hSERT, hDAT, and hNET, respectively) and for binding at SERT, in transiently transfected COS7 cells. Compound 14 demonstrated high affinity binding and selectivity for SERT (K i = 3 nM). Visualization of SERT, using confocal laser scanning microscopy, validated compound 14 as a novel tool for studying SERT expression and distribution in living cells.

Entities:  

Keywords:  Fluorescent ligand; SERT; citalopram; rhodamine

Year:  2014        PMID: 24944746      PMCID: PMC4060933          DOI: 10.1021/ml5000806

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN: 1948-5875            Impact factor:   4.345


  12 in total

1.  Scope of the organocatalysed asymmetric reductive amination of ketones with trichlorosilane.

Authors:  François-Moana Gautier; Simon Jones; Xianfu Li; Stephen J Martin
Journal:  Org Biomol Chem       Date:  2011-09-29       Impact factor: 3.876

Review 2.  Small molecule fluorescent ligands as central nervous system imaging probes.

Authors:  Jacques Joubert; Sandra V Dyk; Sarel F Malan
Journal:  Mini Rev Med Chem       Date:  2013-04-01       Impact factor: 3.862

3.  Rhodamine-labeled 2beta-carbomethoxy-3beta-(3,4-dichlorophenyl)tropane analogues as high-affinity fluorescent probes for the dopamine transporter.

Authors:  Joo Hwan Cha; Mu-Fa Zou; Erika M Adkins; Søren G F Rasmussen; Claus Juul Loland; Bernhard Schoenenberger; Ulrik Gether; Amy Hauck Newman
Journal:  J Med Chem       Date:  2005-12-01       Impact factor: 7.446

Review 4.  Concepts and progress in the development and utilization of receptor-specific fluorescent ligands.

Authors:  N Baindur; D J Triggle
Journal:  Med Res Rev       Date:  1994-11       Impact factor: 12.944

5.  Effects of chronic antidepressant treatments on serotonin transporter function, density, and mRNA level.

Authors:  S Benmansour; M Cecchi; D A Morilak; G A Gerhardt; M A Javors; G G Gould; A Frazer
Journal:  J Neurosci       Date:  1999-12-01       Impact factor: 6.167

6.  A rhodamine-labeled citalopram analogue as a high-affinity fluorescent probe for the serotonin transporter.

Authors:  Peng Zhang; Trine Nygaard Jørgensen; Claus J Loland; Amy Hauck Newman
Journal:  Bioorg Med Chem Lett       Date:  2012-11-01       Impact factor: 2.823

7.  Postendocytic sorting of constitutively internalized dopamine transporter in cell lines and dopaminergic neurons.

Authors:  Jacob Eriksen; Walden Emil Bjørn-Yoshimoto; Trine Nygaard Jørgensen; Amy Hauck Newman; Ulrik Gether
Journal:  J Biol Chem       Date:  2010-06-15       Impact factor: 5.157

8.  Design and synthesis of 1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile (citalopram) analogues as novel probes for the serotonin transporter S1 and S2 binding sites.

Authors:  Ashwini K Banala; Peng Zhang; Per Plenge; George Cyriac; Theresa Kopajtic; Jonathan L Katz; Claus Juul Loland; Amy Hauck Newman
Journal:  J Med Chem       Date:  2013-12-02       Impact factor: 7.446

9.  Visualization of dopamine transporter trafficking in live neurons by use of fluorescent cocaine analogs.

Authors:  Jacob Eriksen; Søren G F Rasmussen; Trine Nygaard Rasmussen; Christian Bjerggaard Vaegter; Joo Hwan Cha; Mu-Fa Zou; Amy Hauck Newman; Ulrik Gether
Journal:  J Neurosci       Date:  2009-05-27       Impact factor: 6.167

10.  A C-terminal PDZ domain-binding sequence is required for striatal distribution of the dopamine transporter.

Authors:  Mattias Rickhag; Freja Herborg Hansen; Gunnar Sørensen; Kristine Nørgaard Strandfelt; Bjørn Andresen; Kamil Gotfryd; Kenneth L Madsen; Ib Vestergaard-Klewe; Ina Ammendrup-Johnsen; Jacob Eriksen; Amy H Newman; Ernst-Martin Füchtbauer; Jesus Gomeza; David P D Woldbye; Gitta Wörtwein; Ulrik Gether
Journal:  Nat Commun       Date:  2013       Impact factor: 14.919

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  8 in total

1.  Analytical Techniques in Neuroscience: Recent Advances in Imaging, Separation, and Electrochemical Methods.

Authors:  Mallikarjunarao Ganesana; Scott T Lee; Ying Wang; B Jill Venton
Journal:  Anal Chem       Date:  2016-11-22       Impact factor: 6.986

2.  Clickable photoaffinity ligands for the human serotonin transporter based on the selective serotonin reuptake inhibitor (S)-citalopram.

Authors:  Nageswari Yarravarapu; Laura Geffert; Christopher K Surratt; Michael Cascio; David J Lapinsky
Journal:  Bioorg Med Chem Lett       Date:  2018-09-22       Impact factor: 2.823

3.  Toward Understanding the Structural Basis of Partial Agonism at the Dopamine D3 Receptor.

Authors:  Mayako Michino; Comfort A Boateng; Prashant Donthamsetti; Hideaki Yano; Oluyomi M Bakare; Alessandro Bonifazi; Michael P Ellenberger; Thomas M Keck; Vivek Kumar; Clare Zhu; Ravi Verma; Jeffrey R Deschamps; Jonathan A Javitch; Amy Hauck Newman; Lei Shi
Journal:  J Med Chem       Date:  2017-01-05       Impact factor: 7.446

4.  Direct visualization of an antidepressant analog using surface-enhanced Raman scattering in the brain.

Authors:  Masato Tanuma; Atsushi Kasai; Kazuki Bando; Naoyuki Kotoku; Kazuo Harada; Masafumi Minoshima; Kosuke Higashino; Atsushi Kimishima; Masayoshi Arai; Yukio Ago; Kaoru Seiriki; Kazuya Kikuchi; Satoshi Kawata; Katsumasa Fujita; Hitoshi Hashimoto
Journal:  JCI Insight       Date:  2020-03-26

5.  Nanopharmacological Force Sensing to Reveal Allosteric Coupling in Transporter Binding Sites.

Authors:  Rong Zhu; Doris Sinwel; Peter S Hasenhuetl; Kusumika Saha; Vivek Kumar; Peng Zhang; Christian Rankl; Marion Holy; Sonja Sucic; Oliver Kudlacek; Andreas Karner; Walter Sandtner; Thomas Stockner; Hermann J Gruber; Michael Freissmuth; Amy Hauck Newman; Harald H Sitte; Peter Hinterdorfer
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-22       Impact factor: 15.336

6.  Novel Azido-Iodo Photoaffinity Ligands for the Human Serotonin Transporter Based on the Selective Serotonin Reuptake Inhibitor (S)-Citalopram.

Authors:  Vivek Kumar; Nageswari Yarravarapu; David J Lapinsky; Danielle Perley; Bruce Felts; Michael J Tomlinson; Roxanne A Vaughan; L Keith Henry; John R Lever; Amy Hauck Newman
Journal:  J Med Chem       Date:  2015-07-08       Impact factor: 7.446

7.  Illuminating the norepinephrine transporter: fluorescent probes based on nisoxetine and talopram.

Authors:  Gisela Andrea Camacho-Hernandez; Andrea Casiraghi; Deborah Rudin; Dino Luethi; Therese C Ku; Daryl A Guthrie; Valentina Straniero; Ermanno Valoti; Gerhard J Schütz; Harald H Sitte; Amy Hauck Newman
Journal:  RSC Med Chem       Date:  2021-06-09

Review 8.  Allosterically Linked Binding Sites in Serotonin Transporter Revealed by Single Molecule Force Spectroscopy.

Authors:  Rong Zhu; Walter Sandtner; Joan E A Ahiable; Amy Hauck Newman; Michael Freissmuth; Harald H Sitte; Peter Hinterdorfer
Journal:  Front Mol Biosci       Date:  2020-06-03
  8 in total

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