Synthesis and evaluation of the first fluorescent antagonists of the human P2Y2 receptor based on AR-C118925

The human P2Y2 receptor (hP2Y2R) is a G protein-coupled receptor that shows promise as a therapeutic target for many important conditions including anti-metastatic cancer therapy and more recently for the treatment of idiopathic pulmonary fibrosis. As such, there is a need for new hP2Y2R antagonists...

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Main Authors: Conroy, Sean, Kindon, Nicholas, Glenn, Jacqueline, Stoddart, Leigh A., Lewis, Richard James, Hill, Stephen J., Kellam, Barrie, Stocks, Michael J.
Format: Article
Published: American Chemical Society 2018
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Online Access:https://eprints.nottingham.ac.uk/50574/
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author Conroy, Sean
Kindon, Nicholas
Glenn, Jacqueline
Stoddart, Leigh A.
Lewis, Richard James
Hill, Stephen J.
Kellam, Barrie
Stocks, Michael J.
author_facet Conroy, Sean
Kindon, Nicholas
Glenn, Jacqueline
Stoddart, Leigh A.
Lewis, Richard James
Hill, Stephen J.
Kellam, Barrie
Stocks, Michael J.
author_sort Conroy, Sean
building Nottingham Research Data Repository
collection Online Access
description The human P2Y2 receptor (hP2Y2R) is a G protein-coupled receptor that shows promise as a therapeutic target for many important conditions including anti-metastatic cancer therapy and more recently for the treatment of idiopathic pulmonary fibrosis. As such, there is a need for new hP2Y2R antagonists and molecular probes to study this receptor. Herein, we report the development of a new series of non-nucleotide hP2Y2R antagonists leading to the discovery of a series of fluorescent ligands containing different linkers and fluorophores based on the known, non-nucleotide hP2Y2R antagonist AR-C118925 (1). One of these conjugates 98 displayed micromolar affinity for the hP2Y2R (pKd = 6.32 ± 0.10; n=17) using a bioluminescence energy transfer (BRET) assay. Confocal microscopy with this ligand revealed displaceable membrane labeling of astrocytoma cells expressing un-tagged hP2Y2R. These properties, make 98 one of the first tools for studying hP2Y2R distribution and organization.
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spelling nottingham-505742020-05-04T19:43:22Z https://eprints.nottingham.ac.uk/50574/ Synthesis and evaluation of the first fluorescent antagonists of the human P2Y2 receptor based on AR-C118925 Conroy, Sean Kindon, Nicholas Glenn, Jacqueline Stoddart, Leigh A. Lewis, Richard James Hill, Stephen J. Kellam, Barrie Stocks, Michael J. The human P2Y2 receptor (hP2Y2R) is a G protein-coupled receptor that shows promise as a therapeutic target for many important conditions including anti-metastatic cancer therapy and more recently for the treatment of idiopathic pulmonary fibrosis. As such, there is a need for new hP2Y2R antagonists and molecular probes to study this receptor. Herein, we report the development of a new series of non-nucleotide hP2Y2R antagonists leading to the discovery of a series of fluorescent ligands containing different linkers and fluorophores based on the known, non-nucleotide hP2Y2R antagonist AR-C118925 (1). One of these conjugates 98 displayed micromolar affinity for the hP2Y2R (pKd = 6.32 ± 0.10; n=17) using a bioluminescence energy transfer (BRET) assay. Confocal microscopy with this ligand revealed displaceable membrane labeling of astrocytoma cells expressing un-tagged hP2Y2R. These properties, make 98 one of the first tools for studying hP2Y2R distribution and organization. American Chemical Society 2018-07-01 Article PeerReviewed Conroy, Sean, Kindon, Nicholas, Glenn, Jacqueline, Stoddart, Leigh A., Lewis, Richard James, Hill, Stephen J., Kellam, Barrie and Stocks, Michael J. (2018) Synthesis and evaluation of the first fluorescent antagonists of the human P2Y2 receptor based on AR-C118925. Journal of Medicinal Chemistry, 61 (7). pp. 3089-3113. ISSN 1520-4804 P2Y2R antagonists fluorescence BRET G Protein-Coupled Receptor GPCR https://pubs.acs.org/doi/10.1021/acs.jmedchem.8b00139 doi:10.1021/acs.jmedchem.8b00139 doi:10.1021/acs.jmedchem.8b00139
spellingShingle P2Y2R
antagonists
fluorescence
BRET
G Protein-Coupled Receptor
GPCR
Conroy, Sean
Kindon, Nicholas
Glenn, Jacqueline
Stoddart, Leigh A.
Lewis, Richard James
Hill, Stephen J.
Kellam, Barrie
Stocks, Michael J.
Synthesis and evaluation of the first fluorescent antagonists of the human P2Y2 receptor based on AR-C118925
title Synthesis and evaluation of the first fluorescent antagonists of the human P2Y2 receptor based on AR-C118925
title_full Synthesis and evaluation of the first fluorescent antagonists of the human P2Y2 receptor based on AR-C118925
title_fullStr Synthesis and evaluation of the first fluorescent antagonists of the human P2Y2 receptor based on AR-C118925
title_full_unstemmed Synthesis and evaluation of the first fluorescent antagonists of the human P2Y2 receptor based on AR-C118925
title_short Synthesis and evaluation of the first fluorescent antagonists of the human P2Y2 receptor based on AR-C118925
title_sort synthesis and evaluation of the first fluorescent antagonists of the human p2y2 receptor based on ar-c118925
topic P2Y2R
antagonists
fluorescence
BRET
G Protein-Coupled Receptor
GPCR
url https://eprints.nottingham.ac.uk/50574/
https://eprints.nottingham.ac.uk/50574/
https://eprints.nottingham.ac.uk/50574/