Discovery of Covalent Inhibitors Targeting the Transcriptional Enhanced Associate Domain Central Pocket.


Journal

Journal of medicinal chemistry
ISSN: 1520-4804
Titre abrégé: J Med Chem
Pays: United States
ID NLM: 9716531

Informations de publication

Date de publication:
22 10 2020
Historique:
pubmed: 11 9 2020
medline: 19 12 2020
entrez: 10 9 2020
Statut: ppublish

Résumé

Transcriptional enhanced associate domain (TEAD) transcription factors together with coactivators and corepressors modulate the expression of genes that regulate fundamental processes, such as organogenesis and cell growth, and elevated TEAD activity is associated with tumorigenesis. Hence, novel modulators of TEAD and methods for their identification are in high demand. We describe the development of a new "thiol conjugation assay" for identification of novel small molecules that bind to the TEAD central pocket. The assay monitors prevention of covalent binding of a fluorescence turn-on probe to a cysteine in the central pocket by small molecules. Screening of a collection of compounds revealed kojic acid analogues as TEAD inhibitors, which covalently target the cysteine in the central pocket, block the interaction with coactivator yes-associated protein with nanomolar apparent IC

Identifiants

pubmed: 32907324
doi: 10.1021/acs.jmedchem.0c01275
pmc: PMC7586386
doi:

Substances chimiques

Pyrones 0
Small Molecule Libraries 0
Sulfhydryl Compounds 0
Transcription Factors 0
kojic acid 6K23F1TT52

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

11972-11989

Références

Int J Mol Sci. 2016 Jan 21;17(1):
pubmed: 26805820
Cell Stem Cell. 2020 May 7;26(5):675-692.e8
pubmed: 32259481
Anal Biochem. 2012 Feb 1;421(1):342-4
pubmed: 22051857
ACS Chem Biol. 2019 Dec 20;14(12):2909-2921
pubmed: 31742995
Oncogene. 2011 Mar 10;30(10):1229-40
pubmed: 21076472
Cancers (Basel). 2018 May 08;10(5):
pubmed: 29738494
Genes Dev. 2008 Jul 15;22(14):1962-71
pubmed: 18579750
Nat Chem Biol. 2016 Apr;12(4):282-9
pubmed: 26900866
Angew Chem Int Ed Engl. 2020 Jun 14;:
pubmed: 32537835
Cells. 2019 Jun 17;8(6):
pubmed: 31212916
Cancers (Basel). 2018 Mar 20;10(3):
pubmed: 29558384
Genes (Basel). 2016 Aug 30;7(9):
pubmed: 27589805
Oncogene. 2017 Nov 23;36(47):6518-6530
pubmed: 28759040
J Med Chem. 2018 Jun 28;61(12):5057-5072
pubmed: 29251924
Oncogene. 2016 May;35(21):2789-800
pubmed: 26387538
Cancer Biol Ther. 2013 May;14(5):390-8
pubmed: 23380592
Development. 2007 Nov;134(21):3827-36
pubmed: 17913785
J Cell Mol Med. 2018 Jul;22(7):3560-3571
pubmed: 29667772
J Proteome Res. 2012 Nov 2;11(11):5301-10
pubmed: 23025254
Structure. 2008 Mar;16(3):351-9
pubmed: 18334210
Br J Cancer. 2008 Dec 2;99(11):1849-58
pubmed: 19002168
Eur J Med Chem. 2019 Dec 15;184:111767
pubmed: 31622854
Genes Dev. 1994 Oct 1;8(19):2293-301
pubmed: 7958896
Cell Chem Biol. 2019 Mar 21;26(3):378-389.e13
pubmed: 30581134
Int J Toxicol. 2010 Nov-Dec;29(6 Suppl):244S-73
pubmed: 21164073
J BUON. 2016 Nov-Dec;21(6):1359-1367
pubmed: 28039692
Cell. 2007 Sep 21;130(6):1120-33
pubmed: 17889654
Biochem J. 2018 Jun 26;475(12):2043-2055
pubmed: 29760238
Eur J Med Chem. 2016 Aug 8;118:64-78
pubmed: 27128174
J Med Chem. 2019 Feb 14;62(3):1291-1305
pubmed: 30640473
Am J Cancer Res. 2018 Jun 01;8(6):932-943
pubmed: 30034932
Cell Rep. 2020 Jun 23;31(12):107809
pubmed: 32579935
J Med Chem. 2015 Jun 25;58(12):4857-73
pubmed: 25719868
Genesis. 2007 Sep;45(9):577-87
pubmed: 17868131
Nat Chem Biol. 2019 Jul;15(7):710-720
pubmed: 31222192
Biochemistry. 2001 Apr 24;40(16):5087-94
pubmed: 11305926
Protein Sci. 2005 Jan;14(1):64-73
pubmed: 15576565
Assay Drug Dev Technol. 2008 Jun;6(3):361-74
pubmed: 18452391
Mech Dev. 2008 Mar-Apr;125(3-4):270-83
pubmed: 18083014
Proc Natl Acad Sci U S A. 2019 May 14;116(20):9877-9882
pubmed: 31043565
Protein Sci. 2017 Dec;26(12):2399-2409
pubmed: 28960584
Structure. 2016 Jan 5;24(1):179-186
pubmed: 26724994
Structure. 2015 Nov 3;23(11):2076-86
pubmed: 26592798
Oncotarget. 2015 Jul 10;6(19):17685-97
pubmed: 25970772
Trends Biochem Sci. 2017 Nov;42(11):862-872
pubmed: 28964625

Auteurs

Hacer Karatas (H)

Department of Chemical Biology, Max Planck Institute of Molecular Physiology, Otto-Hahn Straße 11, 44227 Dortmund, Germany.

Mohammad Akbarzadeh (M)

Department of Chemical Biology, Max Planck Institute of Molecular Physiology, Otto-Hahn Straße 11, 44227 Dortmund, Germany.

Hélène Adihou (H)

Department of Chemical Biology, AstraZeneca-Max Planck Institute Satellite Unit, Otto-Hahn-Strasse 11, 44227 Dortmund, Germany.
Medicinal Chemistry, Research and Early Development Cardiovascular, Renal and Metabolism, BioPharmaceuticals R&D, AstraZeneca, SE-431 83 Gothenburg, Sweden.

Gernot Hahne (G)

Department of Chemical Biology, Max Planck Institute of Molecular Physiology, Otto-Hahn Straße 11, 44227 Dortmund, Germany.

Ajaybabu V Pobbati (AV)

Institute of Molecular and Cell Biology, A*STAR, 61 Biopolis Drive, 138673 Singapore, Singapore.

Elizabeth Yihui Ng (E)

Experimental Drug Development Centre (EDDC), Agency for Science, Technology and Research (A*STAR), 10 Biopolis Road, Chromos, #05-01, 138670, Singapore.

Stéphanie M Guéret (SM)

Department of Chemical Biology, AstraZeneca-Max Planck Institute Satellite Unit, Otto-Hahn-Strasse 11, 44227 Dortmund, Germany.
Medicinal Chemistry, Research and Early Development Cardiovascular, Renal and Metabolism, BioPharmaceuticals R&D, AstraZeneca, SE-431 83 Gothenburg, Sweden.

Sonja Sievers (S)

Department of Chemical Biology, Max Planck Institute of Molecular Physiology, Otto-Hahn Straße 11, 44227 Dortmund, Germany.

Axel Pahl (A)

Department of Chemical Biology, Max Planck Institute of Molecular Physiology, Otto-Hahn Straße 11, 44227 Dortmund, Germany.

Malte Metz (M)

Department of Chemical Biology, Max Planck Institute of Molecular Physiology, Otto-Hahn Straße 11, 44227 Dortmund, Germany.

Sarah Zinken (S)

Department of Chemical Biology, Max Planck Institute of Molecular Physiology, Otto-Hahn Straße 11, 44227 Dortmund, Germany.
Faculty of Chemistry and Chemical Biology, Technical University Dortmund, Otto-Hahn-Straße 6, 44227 Dortmund, Germany.

Lara Dötsch (L)

Department of Chemical Biology, Max Planck Institute of Molecular Physiology, Otto-Hahn Straße 11, 44227 Dortmund, Germany.
Faculty of Chemistry and Chemical Biology, Technical University Dortmund, Otto-Hahn-Straße 6, 44227 Dortmund, Germany.

Christine Nowak (C)

Department of Chemical Biology, Max Planck Institute of Molecular Physiology, Otto-Hahn Straße 11, 44227 Dortmund, Germany.

Sasikala Thavam (S)

Department of Chemical Biology, Max Planck Institute of Molecular Physiology, Otto-Hahn Straße 11, 44227 Dortmund, Germany.

Alexandra Friese (A)

Department of Chemical Biology, Max Planck Institute of Molecular Physiology, Otto-Hahn Straße 11, 44227 Dortmund, Germany.

CongBao Kang (C)

Experimental Drug Development Centre (EDDC), Agency for Science, Technology and Research (A*STAR), 10 Biopolis Road, Chromos, #05-01, 138670, Singapore.

Wanjin Hong (W)

Institute of Molecular and Cell Biology, A*STAR, 61 Biopolis Drive, 138673 Singapore, Singapore.

Herbert Waldmann (H)

Department of Chemical Biology, Max Planck Institute of Molecular Physiology, Otto-Hahn Straße 11, 44227 Dortmund, Germany.
Faculty of Chemistry and Chemical Biology, Technical University Dortmund, Otto-Hahn-Straße 6, 44227 Dortmund, Germany.

Articles similaires

[Redispensing of expensive oral anticancer medicines: a practical application].

Lisanne N van Merendonk, Kübra Akgöl, Bastiaan Nuijen
1.00
Humans Antineoplastic Agents Administration, Oral Drug Costs Counterfeit Drugs

Smoking Cessation and Incident Cardiovascular Disease.

Jun Hwan Cho, Seung Yong Shin, Hoseob Kim et al.
1.00
Humans Male Smoking Cessation Cardiovascular Diseases Female
Humans United States Aged Cross-Sectional Studies Medicare Part C
1.00
Humans Yoga Low Back Pain Female Male

Classifications MeSH