A First-in-Class, Highly Selective and Cell-Active Allosteric Inhibitor of Protein Arginine Methyltr

Shen, Yudao; Li, Fengling; Szewczyk, Magdalena M.; Halabelian, Levon; Chau, Irene; Eram, Mohammad S.; Dela Se?a, Carlo; Park, Kwang-Su; Meng, Fanye; Chen, He; Zeng, Hong; Dong, Aiping; Wu, Hong; Trush, Viacheslav V.; McLeod, David; Zepeda-Velazquez, Carlos A.; Campbell, Robert M.; Mader, Mary M.; Watson, Brian M.; Schapira, Matthieu; Arrowsmith, Cheryl H.; Al-Awar, Rima; Barsyte-Lovejoy, Dalia; Kaniskan, H. Umit; Brown, Peter J.; Vedadi, Masoud; Jin, Jian

doi:10.1021/acs.jmedchem.0c02160

A First-in-Class, Highly Selective and Cell-Active Allosteric Inhibitor of Protein Arginine Methyltr

Journal Article · 01 February 2021 · J. Med. Chem.

DOI:https://doi.org/10.1021/acs.jmedchem.0c02160· OSTI ID:1783858

Shen, Yudao; Li, Fengling; Szewczyk, Magdalena M.; Halabelian, Levon; Chau, Irene; Eram, Mohammad S.; Dela Se?a, Carlo; Park, Kwang-Su; Meng, Fanye; Chen, He; Zeng, Hong; Dong, Aiping; Wu, Hong; Trush, Viacheslav V.; McLeod, David; Zepeda-Velazquez, Carlos A.; Campbell, Robert M.; Mader, Mary M.; Watson, Brian M.; Schapira, Matthieu more »

Research Organization:: Argonne National Lab. (ANL), Argonne, IL (United States). Advanced Photon Source (APS)

Sponsoring Organization:: DOE - Office Of Science; National Institutes of Health (NIH)

OSTI ID:: 1783858

Journal Information:: J. Med. Chem., Vol. 64, Issue (7)

Country of Publication:: United States

Language:: ENGLISH

References (38)

Protein Arginine Methylation in Mammals: Who, What, and Why Bedford, Mark T.; Clarke, Steven G. Molecular Cell, Vol. 33, Issue 1 https://doi.org/10.1016/j.molcel.2008.12.013	journal	January 2009
Inhibitors of Protein Methyltransferases and Demethylases Kaniskan, H. Ümit; Martini, Michael L.; Jin, Jian Chemical Reviews, Vol. 118, Issue 3 https://doi.org/10.1021/acs.chemrev.6b00801	journal	March 2017
Protein arginine methylation of non-histone proteins and its role in diseases Wei, Han; Mundade, Rasika; Lange, Kevin Cell Cycle, Vol. 13, Issue 1 https://doi.org/10.4161/cc.27353	journal	November 2013
PTEN arginine methylation by PRMT6 suppresses PI3K–AKT signaling and modulates pre-mRNA splicing Feng, Jiawen; Dang, Yaping; Zhang, Weiqi Proceedings of the National Academy of Sciences, Vol. 116, Issue 14 https://doi.org/10.1073/pnas.1811028116	journal	March 2019
Protein arginine methyltransferases and cancer Yang, Yanzhong; Bedford, Mark T. Nature Reviews Cancer, Vol. 13, Issue 1 https://doi.org/10.1038/nrc3409	journal	December 2012
Methylation of histone H4 at arginine 3 occurs in vivo and is mediated by the nuclear receptor coactivator PRMT1 Strahl, Brian D.; Briggs, Scott D.; Brame, Cynthia J. Current Biology, Vol. 11, Issue 12 https://doi.org/10.1016/S0960-9822(01)00294-9	journal	June 2001
PRMT5-mediated histone H4 arginine-3 symmetrical dimethylation marks chromatin at G + C-rich regions of the mouse genome Girardot, Michael; Hirasawa, Ryutaro; Kacem, Salim Nucleic Acids Research, Vol. 42, Issue 1 https://doi.org/10.1093/nar/gkt884	journal	October 2013
Histone arginine methylation Di Lorenzo, Alessandra; Bedford, Mark T. FEBS Letters, Vol. 585, Issue 13 https://doi.org/10.1016/j.febslet.2010.11.010	journal	November 2010
Protein Arginine Methyltransferase 7 Regulates Cellular Response to DNA Damage by Methylating Promoter Histones H2A and H4 of the Polymerase δ Catalytic Subunit Gene, POLD1 Karkhanis, Vrajesh; Wang, Li; Tae, Sookil Journal of Biological Chemistry, Vol. 287, Issue 35 https://doi.org/10.1074/jbc.M112.378281	journal	July 2012
Proteomic Dissection of the von Hippel–Lindau (VHL) Interactome Lai, Yanlai; Song, Meihua; Hakala, Kevin Journal of Proteome Research, Vol. 10, Issue 11 https://doi.org/10.1021/pr200642c	journal	November 2011
PRMT5 Is Required for Lymphomagenesis Triggered by Multiple Oncogenic Drivers Li, Yan; Chitnis, Nilesh; Nakagawa, Hiroshi Cancer Discovery, Vol. 5, Issue 3 https://doi.org/10.1158/2159-8290.CD-14-0625	journal	January 2015
Symmetric dimethylation of H3R2 is a newly identified histone mark that supports euchromatin maintenance Migliori, Valentina; Müller, Julius; Phalke, Sameer Nature Structural & Molecular Biology, Vol. 19, Issue 2 https://doi.org/10.1038/nsmb.2209	journal	January 2012
A Potent, Selective and Cell-Active Allosteric Inhibitor of Protein Arginine Methyltransferase 3 (PRMT3) Kaniskan, H. Ümit; Szewczyk, Magdalena M.; Yu, Zhengtian Angewandte Chemie International Edition, Vol. 54, Issue 17 https://doi.org/10.1002/anie.201412154	journal	February 2015
TP-064, a potent and selective small molecule inhibitor of PRMT4 for multiple myeloma Nakayama, Kazuhide; Szewczyk, Magdalena M.; Sena, Carlo dela Oncotarget, Vol. 9, Issue 26 https://doi.org/10.18632/oncotarget.24883	journal	March 2018
A selective inhibitor of PRMT5 with in vivo and in vitro potency in MCL models Chan-Penebre, Elayne; Kuplast, Kristy G.; Majer, Christina R. Nature Chemical Biology, Vol. 11, Issue 6 https://doi.org/10.1038/nchembio.1810	journal	April 2015
Discovery of Potent and Selective Covalent Protein Arginine Methyltransferase 5 (PRMT5) Inhibitors Lin, Hong; Wang, Min; Zhang, Yang W. ACS Medicinal Chemistry Letters, Vol. 10, Issue 7 https://doi.org/10.1021/acsmedchemlett.9b00074	journal	May 2019
LLY-283, a Potent and Selective Inhibitor of Arginine Methyltransferase 5, PRMT5, with Antitumor Activity Bonday, Zahid Q.; Cortez, Guillermo S.; Grogan, Michael J. ACS Medicinal Chemistry Letters, Vol. 9, Issue 7 https://doi.org/10.1021/acsmedchemlett.8b00014	journal	April 2018
Potent, Selective, and Cell Active Protein Arginine Methyltransferase 5 (PRMT5) Inhibitor Developed by Structure-Based Virtual Screening and Hit Optimization Mao, Ruifeng; Shao, Jingwei; Zhu, Kongkai Journal of Medicinal Chemistry, Vol. 60, Issue 14 https://doi.org/10.1021/acs.jmedchem.7b00587	journal	July 2017
Selective small-chemical inhibitors of protein arginine methyltransferase 5 with anti-lung cancer activity Kong, Gui-Mei; Yu, Min; Gu, Zhongping PLOS ONE, Vol. 12, Issue 8 https://doi.org/10.1371/journal.pone.0181601	journal	August 2017
Pharmacological inhibition of PRMT7 links arginine monomethylation to the cellular stress response Szewczyk, Magdalena M.; Ishikawa, Yoshinori; Organ, Shawna Nature Communications, Vol. 11, Issue 1 https://doi.org/10.1038/s41467-020-16271-z	journal	May 2020
The Novel Human Protein Arginine N-Methyltransferase PRMT6 Is a Nuclear Enzyme Displaying Unique Substrate Specificity Frankel, Adam; Yadav, Neelu; Lee, Jaeho Journal of Biological Chemistry, Vol. 277, Issue 5 https://doi.org/10.1074/jbc.M108786200	journal	February 2002
Mouse Models of Overexpression Reveal Distinct Oncogenic Roles for Different Type I Protein Arginine Methyltransferases Bao, Jianqiang; Di Lorenzo, Alessandra; Lin, Kevin Cancer Research, Vol. 79, Issue 1 https://doi.org/10.1158/0008-5472.CAN-18-1995	journal	October 2018
The Arginine Methyltransferase PRMT6 Regulates DNA Methylation and Contributes to Global DNA Hypomethylation in Cancer Veland, Nicolas; Hardikar, Swanand; Zhong, Yi Cell Reports, Vol. 21, Issue 12 https://doi.org/10.1016/j.celrep.2017.11.082	journal	December 2017
A Potent, Selective, and Cell-Active Inhibitor of Human Type I Protein Arginine Methyltransferases Eram, Mohammad S.; Shen, Yudao; Szewczyk, Magdalena M. ACS Chemical Biology, Vol. 11, Issue 3 https://doi.org/10.1021/acschembio.5b00839	journal	December 2015
Discovery of a First-in-Class Protein Arginine Methyltransferase 6 (PRMT6) Covalent Inhibitor Shen, Yudao; Li, Fengling; Szewczyk, Magdalena M. Journal of Medicinal Chemistry, Vol. 63, Issue 10 https://doi.org/10.1021/acs.jmedchem.0c00406	journal	May 2020
Aryl Pyrazoles as Potent Inhibitors of Arginine Methyltransferases: Identification of the First PRMT6 Tool Compound Mitchell, Lorna H.; Drew, Allison E.; Ribich, Scott A. ACS Medicinal Chemistry Letters, Vol. 6, Issue 6 https://doi.org/10.1021/acsmedchemlett.5b00071	journal	April 2015
Allosteric Modulation of Protein Arginine Methyltransferase 5 (PRMT5) Palte, Rachel L.; Schneider, Sebastian E.; Altman, Michael D. ACS Medicinal Chemistry Letters, Vol. 11, Issue 9 https://doi.org/10.1021/acsmedchemlett.9b00525	journal	August 2020
Functional insights from high resolution structures of mouse protein arginine methyltransferase 6 Bonnefond, Luc; Stojko, Johann; Mailliot, Justine Journal of Structural Biology, Vol. 191, Issue 2 https://doi.org/10.1016/j.jsb.2015.06.017	journal	August 2015
Substituent Effects in π−π Interactions: Sandwich and T-Shaped Configurations Sinnokrot, Mutasem Omar; Sherrill, C. David Journal of the American Chemical Society, Vol. 126, Issue 24 https://doi.org/10.1021/ja049434a	journal	June 2004
Discovery of a Potent Class I Protein Arginine Methyltransferase Fragment Inhibitor Ferreira de Freitas, Renato; Eram, Mohammad S.; Szewczyk, Magdalena M. Journal of Medicinal Chemistry, Vol. 59, Issue 3 https://doi.org/10.1021/acs.jmedchem.5b01772	journal	January 2016
HKL -3000: the integration of data reduction and structure solution – from diffraction images to an initial model in minutes Minor, Wladek; Cymborowski, Marcin; Otwinowski, Zbyszek Acta Crystallographica Section D Biological Crystallography, Vol. 62, Issue 8 https://doi.org/10.1107/S0907444906019949	journal	July 2006
Refinement of Macromolecular Structures by the Maximum-Likelihood Method Murshudov, G. N.; Vagin, A. A.; Dodson, E. J. Acta Crystallographica Section D Biological Crystallography, Vol. 53, Issue 3 https://doi.org/10.1107/S0907444996012255	journal	May 1997
Exploiting structure similarity in refinement: automated NCS and target-structure restraints in BUSTER Smart, Oliver S.; Womack, Thomas O.; Flensburg, Claus Acta Crystallographica Section D Biological Crystallography, Vol. 68, Issue 4 https://doi.org/10.1107/S0907444911056058	journal	March 2012
Coot model-building tools for molecular graphics Emsley, Paul; Cowtan, Kevin Acta Crystallographica Section D Biological Crystallography, Vol. 60, Issue 12, p. 2126-2132 https://doi.org/10.1107/S0907444904019158	journal	November 2004
MOLPROBITY: structure validation and all-atom contact analysis for nucleic acids and their complexes Davis, I. W.; Murray, L. W.; Richardson, J. S. Nucleic Acids Research, Vol. 32, Issue Web Server https://doi.org/10.1093/nar/gkh398	journal	July 2004
Structural basis of arginine asymmetrical dimethylation by PRMT6 Wu, Hong; Zheng, Weihong; Eram, Mohammad S. Biochemical Journal, Vol. 473, Issue 19 https://doi.org/10.1042/BCJ20160537	journal	September 2016
Exploiting an Allosteric Binding Site of PRMT3 Yields Potent and Selective Inhibitors Liu, Feng; Li, Fengling; Ma, Anqi Journal of Medicinal Chemistry, Vol. 56, Issue 5 https://doi.org/10.1021/jm3018332	journal	February 2013
A chemical biology toolbox to study protein methyltransferases and epigenetic signaling Scheer, Sebastian; Ackloo, Suzanne; Medina, Tiago S. Nature Communications, Vol. 10, Issue 1 https://doi.org/10.1038/s41467-018-07905-4	journal	January 2019

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