Discovery of a Potent Class I Protein Arginine Methyltransferase Fragment Inhibitor

Protein methyltransferases (PMTs) are a promising target class in oncology and other disease areas. They are composed of SET domain methyltransferases and structurally unrelated Rossman-fold enzymes that include protein arginine methyltransferases (PRMTs). In the absence of a well-defined medicinal...

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Veröffentlicht in:Journal of medicinal chemistry 2016-02, Vol.59 (3), p.1176-1183
Hauptverfasser: Ferreira de Freitas, Renato, Eram, Mohammad S, Szewczyk, Magdalena M, Steuber, Holger, Smil, David, Wu, Hong, Li, Fengling, Senisterra, Guillermo, Dong, Aiping, Brown, Peter J, Hitchcock, Marion, Moosmayer, Dieter, Stegmann, Christian M, Egner, Ursula, Arrowsmith, Cheryl, Barsyte-Lovejoy, Dalia, Vedadi, Masoud, Schapira, Matthieu
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container_end_page 1183
container_issue 3
container_start_page 1176
container_title Journal of medicinal chemistry
container_volume 59
creator Ferreira de Freitas, Renato
Eram, Mohammad S
Szewczyk, Magdalena M
Steuber, Holger
Smil, David
Wu, Hong
Li, Fengling
Senisterra, Guillermo
Dong, Aiping
Brown, Peter J
Hitchcock, Marion
Moosmayer, Dieter
Stegmann, Christian M
Egner, Ursula
Arrowsmith, Cheryl
Barsyte-Lovejoy, Dalia
Vedadi, Masoud
Schapira, Matthieu
description Protein methyltransferases (PMTs) are a promising target class in oncology and other disease areas. They are composed of SET domain methyltransferases and structurally unrelated Rossman-fold enzymes that include protein arginine methyltransferases (PRMTs). In the absence of a well-defined medicinal chemistry tool-kit focused on PMTs, most current inhibitors were identified by screening large and diverse libraries of leadlike molecules. So far, no successful fragment-based approach was reported against this target class. Here, by deconstructing potent PRMT inhibitors, we find that chemical moieties occupying the substrate arginine-binding site can act as efficient fragment inhibitors. Screening a fragment library against PRMT6 produced numerous hits, including a 300 nM inhibitor (ligand efficiency of 0.56) that decreased global histone 3 arginine 2 methylation in cells, and can serve as a warhead for the development of PRMT chemical probes.
doi_str_mv 10.1021/acs.jmedchem.5b01772
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They are composed of SET domain methyltransferases and structurally unrelated Rossman-fold enzymes that include protein arginine methyltransferases (PRMTs). In the absence of a well-defined medicinal chemistry tool-kit focused on PMTs, most current inhibitors were identified by screening large and diverse libraries of leadlike molecules. So far, no successful fragment-based approach was reported against this target class. Here, by deconstructing potent PRMT inhibitors, we find that chemical moieties occupying the substrate arginine-binding site can act as efficient fragment inhibitors. 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subjects Dose-Response Relationship, Drug
Drug Discovery
Enzyme Inhibitors - chemical synthesis
Enzyme Inhibitors - chemistry
Enzyme Inhibitors - pharmacology
Humans
Models, Molecular
Molecular Structure
Protein-Arginine N-Methyltransferases - antagonists & inhibitors
Protein-Arginine N-Methyltransferases - metabolism
Repressor Proteins - antagonists & inhibitors
Repressor Proteins - metabolism
Structure-Activity Relationship
title Discovery of a Potent Class I Protein Arginine Methyltransferase Fragment Inhibitor
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