Synthesis, modeling and functional activity of substituted styrene-amides as small-molecule CXCR7 agonists
The chemokine receptor CXCR7 is an atypical G protein-coupled receptor as it preferentially signals through the β-arrestin pathway rather than through G proteins. CXCR7 is thought to be of importance in cancer and the development of CXCR7-targeting ligands is of huge importance to further elucidate...
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Published in | European journal of medicinal chemistry Vol. 51; pp. 184 - 192 |
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Main Authors | , , , , , , , , , , , , , |
Format | Journal Article |
Language | English |
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ISSY-LES-MOULINEAUX
Elsevier Masson SAS
01.05.2012
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Abstract | The chemokine receptor CXCR7 is an atypical G protein-coupled receptor as it preferentially signals through the β-arrestin pathway rather than through G proteins. CXCR7 is thought to be of importance in cancer and the development of CXCR7-targeting ligands is of huge importance to further elucidate the pharmacology and the therapeutic potential of CXCR7. In the present study, we synthesized 24 derivatives based on a compound scaffold patented by Chemocentryx and obtained CXCR7 ligands with pKi values ranging from 5.3 to 8.1. SAR studies were supported by computational 3D Fingerprint studies, revealing several important affinity descriptors. Two key compounds (29 and 30, VUF11207 and VUF11403) were found to be high-potency ligands that induce recruitment of β-arrestin2 and subsequent internalization of CXCR7, making them important tool compounds in future CXCR7 research.
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► Substituted styrene-amides are excellent CXCR7 binders. ► Computational model suggests important molecular descriptors. ► Key compounds induce recruitment of β-arrestin2 to CXCR7. ► Key compounds induce CXCR7 internalization. |
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AbstractList | The chemokine receptor CXCR7 is an atypical G protein-coupled receptor as it preferentially signals through the β-arrestin pathway rather than through G proteins. CXCR7 is thought to be of importance in cancer and the development of CXCR7-targeting ligands is of huge importance to further elucidate the pharmacology and the therapeutic potential of CXCR7. In the present study, we synthesized 24 derivatives based on a compound scaffold patented by Chemocentryx and obtained CXCR7 ligands with pKi values ranging from 5.3 to 8.1. SAR studies were supported by computational 3D Fingerprint studies, revealing several important affinity descriptors. Two key compounds (29 and 30, VUF11207 and VUF11403) were found to be high-potency ligands that induce recruitment of β-arrestin2 and subsequent internalization of CXCR7, making them important tool compounds in future CXCR7 research.
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► Substituted styrene-amides are excellent CXCR7 binders. ► Computational model suggests important molecular descriptors. ► Key compounds induce recruitment of β-arrestin2 to CXCR7. ► Key compounds induce CXCR7 internalization. The chemokine receptor CXCR7 is an atypical G protein-coupled receptor as it preferentially signals through the beta-arrestin pathway rather than through G proteins. CXCR7 is thought to be of importance in cancer and the development of CXCR7-targeting ligands is of huge importance to further elucidate the pharmacology and the therapeutic potential of CXCR7. In the present study, we synthesized 24 derivatives based on a compound scaffold patented by Chemocentryx and obtained CXCR7 ligands with pK(i) values ranging from 5.3 to 8.1. SAR studies were supported by computational 3D Fingerprint studies, revealing several important affinity descriptors. Two key compounds (29 and 30, VUF11207 and VUF11403) were found to be high-potency ligands that induce recruitment of beta-arrestin2 and subsequent internalization of CXCR7, making them important tool compounds in future CXCR7 research. (C) 2012 Elsevier Masson SAS. All rights reserved. The chemokine receptor CXCR7 is an atypical G protein-coupled receptor as it preferentially signals through the β-arrestin pathway rather than through G proteins. CXCR7 is thought to be of importance in cancer and the development of CXCR7-targeting ligands is of huge importance to further elucidate the pharmacology and the therapeutic potential of CXCR7. In the present study, we synthesized 24 derivatives based on a compound scaffold patented by Chemocentryx and obtained CXCR7 ligands with pK(i) values ranging from 5.3 to 8.1. SAR studies were supported by computational 3D Fingerprint studies, revealing several important affinity descriptors. Two key compounds (29 and 30, VUF11207 and VUF11403) were found to be high-potency ligands that induce recruitment of β-arrestin2 and subsequent internalization of CXCR7, making them important tool compounds in future CXCR7 research. |
Author | Smit, Martine J. Leurs, Rob Wijtmans, Maikel Mujić-Delić, Azra Scholten, Danny J. Maussang, David Chatalic, Kristell L.S. Sirci, Francesco Custers, Hans Chong, Milagros Canals, Meritxell de Esch, Iwan J.P. de Graaf, Chris Janssen, Elwin |
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Keywords | BRET Agonist RT YFP Ligand EDCI LDA β-arrestin2 CXCR7 Cm MIF RLuc CzH FLAP Internalization HOBT GPCR NOESY 3D fingerprint HBSS ELISA ERK MIGRATION RDC1 CHEMOKINE RECEPTOR CXCR7 beta-arrestin2 |
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Snippet | The chemokine receptor CXCR7 is an atypical G protein-coupled receptor as it preferentially signals through the β-arrestin pathway rather than through G... The chemokine receptor CXCR7 is an atypical G protein-coupled receptor as it preferentially signals through the beta-arrestin pathway rather than through G... |
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SubjectTerms | 3D fingerprint Agonist Amides - chemistry Biological and medical sciences Chemistry Techniques, Synthetic Chemistry, Medicinal CXCR7 HEK293 Cells Humans Internalization Life Sciences & Biomedicine Ligand Medical sciences Miscellaneous Models, Molecular Molecular Conformation Pharmacology & Pharmacy Pharmacology. Drug treatments Quantitative Structure-Activity Relationship Receptors, CXCR - agonists Science & Technology Styrene - chemical synthesis Styrene - chemistry Styrene - pharmacology β-arrestin2 |
Title | Synthesis, modeling and functional activity of substituted styrene-amides as small-molecule CXCR7 agonists |
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