Identification and Optimization of 4‐Anilinoquinolines as Inhibitors of Cyclin G Associated Kinase
4‐Anilinoquinolines were identified as potent and narrow‐spectrum inhibitors of the cyclin G associated kinase (GAK), an important regulator of viral and bacterial entry into host cells. Optimization of the 4‐anilino group and the 6,7‐quinoline substituents produced GAK inhibitors with nanomolar act...
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Published in | ChemMedChem Vol. 13; no. 1; pp. 48 - 66 |
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Main Authors | , , , , , , , , , , , , |
Format | Journal Article |
Language | English |
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08.01.2018
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Abstract | 4‐Anilinoquinolines were identified as potent and narrow‐spectrum inhibitors of the cyclin G associated kinase (GAK), an important regulator of viral and bacterial entry into host cells. Optimization of the 4‐anilino group and the 6,7‐quinoline substituents produced GAK inhibitors with nanomolar activity, over 50 000‐fold selectivity relative to other members of the numb‐associated kinase (NAK) subfamily, and a compound (6,7‐dimethoxy‐N‐(3,4,5‐trimethoxyphenyl)quinolin‐4‐amine; 49) with a narrow‐spectrum kinome profile. These compounds may be useful tools to explore the therapeutic potential of GAK in prevention of a broad range of infectious and systemic diseases.
Targeting GAK: The availability of chemical probes with improved selectivity for cyclin G associated kinase (GAK) or a different spectrum of off‐targets would be useful in target validation studies. Herein we report the synthesis and characterization of 4‐anilinoquinolines and 4‐anilinoquinazolines as potent narrow‐spectrum GAK inhibitors. Several of these compounds have the potential for development into high‐quality chemical probes for the study of GAK biology. |
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AbstractList | 4‐Anilinoquinolines were identified as potent and narrow‐spectrum inhibitors of the cyclin G associated kinase (GAK), an important regulator of viral and bacterial entry into host cells. Optimization of the 4‐anilino group and the 6,7‐quinoline substituents produced GAK inhibitors with nanomolar activity, over 50 000‐fold selectivity relative to other members of the numb‐associated kinase (NAK) subfamily, and a compound (6,7‐dimethoxy‐N‐(3,4,5‐trimethoxyphenyl)quinolin‐4‐amine; 49) with a narrow‐spectrum kinome profile. These compounds may be useful tools to explore the therapeutic potential of GAK in prevention of a broad range of infectious and systemic diseases.
Targeting GAK: The availability of chemical probes with improved selectivity for cyclin G associated kinase (GAK) or a different spectrum of off‐targets would be useful in target validation studies. Herein we report the synthesis and characterization of 4‐anilinoquinolines and 4‐anilinoquinazolines as potent narrow‐spectrum GAK inhibitors. Several of these compounds have the potential for development into high‐quality chemical probes for the study of GAK biology. 4-Anilinoquinolines were identified as potent and narrow-spectrum inhibitors of the cyclin G associated kinase (GAK), an important regulator of viral and bacterial entry into host cells. Optimization of the 4-anilino group and the 6,7-quinoline substituents produced GAK inhibitors with nanomolar activity, over 50 000-fold selectivity relative to other members of the numb-associated kinase (NAK) subfamily, and a compound (6,7-dimethoxy-N-(3,4,5-trimethoxyphenyl)quinolin-4-amine; 49) with a narrow-spectrum kinome profile. These compounds may be useful tools to explore the therapeutic potential of GAK in prevention of a broad range of infectious and systemic diseases. 4-Anilinoquinolines were identified as potent and narrow spectrum inhibitors of the cyclin G associated kinase (GAK), an important regulator of viral and bacterial entry into host cells. Optimization of the 4-anilino group and the 6,7-quinoline substituents produced GAK inhibitors with nanomolar activity, over 50,000-fold selectivity relative to other members of the numb-associated kinase (NAK) sub-family, and narrow activity spectra in the broader kinome. These compounds may be useful tools to explore the therapeutic potential of GAK in prevention of a broad range of infectious and systemic diseases. Abstract 4‐Anilinoquinolines were identified as potent and narrow‐spectrum inhibitors of the cyclin G associated kinase (GAK), an important regulator of viral and bacterial entry into host cells. Optimization of the 4‐anilino group and the 6,7‐quinoline substituents produced GAK inhibitors with nanomolar activity, over 50 000‐fold selectivity relative to other members of the numb‐associated kinase (NAK) subfamily, and a compound (6,7‐dimethoxy‐ N ‐(3,4,5‐trimethoxyphenyl)quinolin‐4‐amine; 49 ) with a narrow‐spectrum kinome profile. These compounds may be useful tools to explore the therapeutic potential of GAK in prevention of a broad range of infectious and systemic diseases. |
Author | Graves, Lee M. Dornsife, Ronna E. Laitinen, Tuomo Johnson, Gary L. Wells, Carrow I. Asquith, Christopher R. M. Bennett, James M. Godoi, Paulo H. Tizzard, Graham J. East, Michael P. Zuercher, William J. Elkins, Jonathan M. Willson, Timothy M. |
AuthorAffiliation | 3 Structural Genomics Consortium and Target Discovery Institute, Nuffield Department of Clinical Medicine, University of Oxford, Old Road Campus Research Building, Oxford, OX3 7DQ, UK 1 Structural Genomics Consortium, UNC Eshelman School of Pharmacy, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599, USA 2 School of Pharmacy, Faculty of Health Sciences, University of Eastern Finland, 70211 Kuopio, Finland 4 Structural Genomics Consortium, Universidade Estadual de Campinas - UNICAMP, Campinas, São Paulo, 13083-886, Brazil 5 Department of Pharmacology, University of North Carolina at Chapel Hill, NC 27599, USA 6 UK National Crystallography Service, School of Chemistry, University of Southampton, Highfield Campus, Southampton, SO17 1BJ, UK |
AuthorAffiliation_xml | – name: 6 UK National Crystallography Service, School of Chemistry, University of Southampton, Highfield Campus, Southampton, SO17 1BJ, UK – name: 3 Structural Genomics Consortium and Target Discovery Institute, Nuffield Department of Clinical Medicine, University of Oxford, Old Road Campus Research Building, Oxford, OX3 7DQ, UK – name: 1 Structural Genomics Consortium, UNC Eshelman School of Pharmacy, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599, USA – name: 2 School of Pharmacy, Faculty of Health Sciences, University of Eastern Finland, 70211 Kuopio, Finland – name: 4 Structural Genomics Consortium, Universidade Estadual de Campinas - UNICAMP, Campinas, São Paulo, 13083-886, Brazil – name: 5 Department of Pharmacology, University of North Carolina at Chapel Hill, NC 27599, USA |
Author_xml | – sequence: 1 givenname: Christopher R. M. orcidid: 0000-0001-5871-3458 surname: Asquith fullname: Asquith, Christopher R. M. organization: University of North Carolina at Chapel Hill – sequence: 2 givenname: Tuomo surname: Laitinen fullname: Laitinen, Tuomo organization: University of Eastern Finland – sequence: 3 givenname: James M. surname: Bennett fullname: Bennett, James M. organization: University of Oxford – sequence: 4 givenname: Paulo H. surname: Godoi fullname: Godoi, Paulo H. organization: Universidade Estadual de Campinas—UNICAMP – sequence: 5 givenname: Michael P. surname: East fullname: East, Michael P. organization: University of North Carolina at Chapel Hill – sequence: 6 givenname: Graham J. surname: Tizzard fullname: Tizzard, Graham J. organization: University of Southampton – sequence: 7 givenname: Lee M. surname: Graves fullname: Graves, Lee M. organization: University of North Carolina at Chapel Hill – sequence: 8 givenname: Gary L. surname: Johnson fullname: Johnson, Gary L. organization: University of North Carolina at Chapel Hill – sequence: 9 givenname: Ronna E. surname: Dornsife fullname: Dornsife, Ronna E. organization: University of North Carolina at Chapel Hill – sequence: 10 givenname: Carrow I. orcidid: 0000-0003-4799-6792 surname: Wells fullname: Wells, Carrow I. organization: University of North Carolina at Chapel Hill – sequence: 11 givenname: Jonathan M. orcidid: 0000-0003-2858-8929 surname: Elkins fullname: Elkins, Jonathan M. organization: Universidade Estadual de Campinas—UNICAMP – sequence: 12 givenname: Timothy M. orcidid: 0000-0003-4181-8223 surname: Willson fullname: Willson, Timothy M. organization: University of North Carolina at Chapel Hill – sequence: 13 givenname: William J. orcidid: 0000-0002-9836-0068 surname: Zuercher fullname: Zuercher, William J. email: william.zuercher@unc.edu organization: University of North Carolina at Chapel Hill |
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Keywords | chemical probes cyclin G associated kinase (GAK) anilinoquinolines antibacterial agents |
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Snippet | 4‐Anilinoquinolines were identified as potent and narrow‐spectrum inhibitors of the cyclin G associated kinase (GAK), an important regulator of viral and... 4-Anilinoquinolines were identified as potent and narrow-spectrum inhibitors of the cyclin G associated kinase (GAK), an important regulator of viral and... Abstract 4‐Anilinoquinolines were identified as potent and narrow‐spectrum inhibitors of the cyclin G associated kinase (GAK), an important regulator of viral... 4-Anilinoquinolines were identified as potent and narrow spectrum inhibitors of the cyclin G associated kinase (GAK), an important regulator of viral and... |
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SubjectTerms | Aniline Compounds - chemistry Aniline Compounds - metabolism Aniline Compounds - pharmacology anilinoquinolines antibacterial agents Binding Sites Catalytic Domain chemical probes cyclin G associated kinase (GAK) Drug Design Endocytosis - drug effects Humans Intracellular Signaling Peptides and Proteins - antagonists & inhibitors Intracellular Signaling Peptides and Proteins - metabolism Kinetics Molecular Docking Simulation Protein Binding Protein Kinase Inhibitors - chemistry Protein Kinase Inhibitors - metabolism Protein Kinase Inhibitors - pharmacology Protein Serine-Threonine Kinases - antagonists & inhibitors Protein Serine-Threonine Kinases - metabolism Quinazolines - chemistry Quinazolines - metabolism Quinazolines - pharmacology Structure-Activity Relationship Viruses - pathogenicity |
Title | Identification and Optimization of 4‐Anilinoquinolines as Inhibitors of Cyclin G Associated Kinase |
URI | https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fcmdc.201700663 https://www.ncbi.nlm.nih.gov/pubmed/29072804 https://www.proquest.com/docview/1956078965/abstract/ https://pubmed.ncbi.nlm.nih.gov/PMC5914168 |
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