ACS Publications. Most Trusted. Most Cited. Most Read
Chemical Proteomic Profiling of Human Methyltransferases
My Activity

Figure 1Loading Img
    Article

    Chemical Proteomic Profiling of Human Methyltransferases
    Click to copy article linkArticle link copied!

    View Author Information
    Departments of Chemical Physiology, The Scripps Research Institute, La Jolla, California 92307, United States
    Other Access OptionsSupporting Information (2)

    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2016, 138, 40, 13335–13343
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jacs.6b07830
    Published September 30, 2016
    Copyright © 2016 American Chemical Society

    Abstract

    Click to copy section linkSection link copied!
    Abstract Image

    Methylation is a fundamental mechanism used in Nature to modify the structure and function of biomolecules, including proteins, DNA, RNA, and metabolites. Methyl groups are predominantly installed into biomolecules by a large and diverse class of S-adenosyl methionine (SAM)-dependent methyltransferases (MTs), of which there are ∼200 known or putative members in the human proteome. Deregulated MT activity contributes to numerous diseases, including cancer, and several MT inhibitors are in clinical development. Nonetheless, a large fraction of the human MT family remains poorly characterized, underscoring the need for new technologies to characterize MTs and their inhibitors in native biological systems. Here, we describe a suite of S-adenosyl homocysteine (SAH) photoreactive probes and their application in chemical proteomic experiments to profile and enrich a large number of MTs (>50) from human cancer cell lysates with remarkable specificity over other classes of proteins. We further demonstrate that the SAH probes can enrich MT-associated proteins and be used to screen for and assess the selectivity of MT inhibitors, leading to the discovery of a covalent inhibitor of nicotinamide N-methyltransferase (NNMT), an enzyme implicated in cancer and metabolic disorders. The chemical proteomics probes and methods for their utilization reported herein should prove of value for the functional characterization of MTs, MT complexes, and MT inhibitors in mammalian biology and disease.

    Copyright © 2016 American Chemical Society

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. Add or change your institution or let them know you’d like them to include access.

    Supporting Information

    Click to copy section linkSection link copied!

    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/jacs.6b07830.

    • Detailed synthetic and experimental procedures, analytical (NMR, HRMS) characterization of compounds, and supplementary figures (PDF)

    • Supplementary tables containing proteomic data (XLSX)

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    Click to copy section linkSection link copied!
    Citation Statements
    Explore this article's citation statements on scite.ai

    This article is cited by 80 publications.

    1. Lei Gao, Qi Ding, Xiaoguang Lei. Hunting for the Intermolecular Diels–Alderase. Accounts of Chemical Research 2024, 57 (15) , 2166-2183. https://doi.org/10.1021/acs.accounts.4c00315
    2. Laura Hillebrand, Xiaojun Julia Liang, Ricardo A. M. Serafim, Matthias Gehringer. Emerging and Re-emerging Warheads for Targeted Covalent Inhibitors: An Update. Journal of Medicinal Chemistry 2024, 67 (10) , 7668-7758. https://doi.org/10.1021/acs.jmedchem.3c01825
    3. Wei Dai, Nathan J. Yu, Ralph E. Kleiner. Chemoproteomic Approaches to Studying RNA Modification-Associated Proteins. Accounts of Chemical Research 2023, 56 (19) , 2726-2739. https://doi.org/10.1021/acs.accounts.3c00450
    4. Quinlin M. Hanson, Nate Hoxie, Min Shen, Hui Guo, Ig-Jun Cho, Ipsita Chakraborty, Brooklyn M. Aragon, Ganesha Rai, Samarjit Patnaik, John S. Janiszewski, Matthew D. Hall. Target Class Profiling of Small-Molecule Methyltransferases. ACS Chemical Biology 2023, 18 (4) , 969-981. https://doi.org/10.1021/acschembio.3c00124
    5. Zhuoyuan Zhang, Jianwei Lin, Zheng Liu, Gaofei Tian, Xiao-Meng Li, Yihang Jing, Xin Li, Xiang David Li. Photo-Cross-Linking To Delineate Epigenetic Interactome. Journal of the American Chemical Society 2022, 144 (46) , 20979-20997. https://doi.org/10.1021/jacs.2c06135
    6. Kyohei Hayashi, Shota Uehara, Shiho Yamamoto, Douglas R. Cary, Junichi Nishikawa, Taichi Ueda, Hiroki Ozasa, Kousuke Mihara, Norito Yoshimura, Taeko Kawai, Takashi Ono, Saki Yamamoto, Masataka Fumoto, Hidenori Mikamiyama. Macrocyclic Peptides as a Novel Class of NNMT Inhibitors: A SAR Study Aimed at Inhibitory Activity in the Cell. ACS Medicinal Chemistry Letters 2021, 12 (7) , 1093-1101. https://doi.org/10.1021/acsmedchemlett.1c00134
    7. Justina Šileikytė, Sunil Sundalam, Larry L. David, Michael S. Cohen. Chemical Proteomics Approach for Profiling the NAD Interactome. Journal of the American Chemical Society 2021, 143 (18) , 6787-6791. https://doi.org/10.1021/jacs.1c01302
    8. Hitoshi Ouchi, Takuya Namiki, Kenji Iwamoto, Nobuo Matsuzaki, Makoto Inai, Mihaya Kotajima, Jing Wu, Jae-Hoon Choi, Yoko Kimura, Hirofumi Hirai, Xiaonan Xie, Hirokazu Kawagishi, Toshiyuki Kan. S-Adenosylhomocysteine Analogue of a Fairy Chemical, Imidazole-4-carboxamide, as its Metabolite in Rice and Yeast and Synthetic Investigations of Related Compounds. Journal of Natural Products 2021, 84 (2) , 453-458. https://doi.org/10.1021/acs.jnatprod.0c01269
    9. Jian Cao, Lisa M. Boatner, Heta S. Desai, Nikolas R. Burton, Ernest Armenta, Neil J. Chan, José O. Castellón, Keriann M. Backus. Multiplexed CuAAC Suzuki–Miyaura Labeling for Tandem Activity-Based Chemoproteomic Profiling. Analytical Chemistry 2021, 93 (4) , 2610-2618. https://doi.org/10.1021/acs.analchem.0c04726
    10. Yihang Jing, Jose L. Montano, Michaella Levy, Jeffrey E. Lopez, Pei-Pei Kung, Paul Richardson, Krzysztof Krajewski, Laurence Florens, Michael P. Washburn, Jordan L. Meier. Harnessing Ionic Selectivity in Acetyltransferase Chemoproteomic Probes. ACS Chemical Biology 2021, 16 (1) , 27-34. https://doi.org/10.1021/acschembio.0c00766
    11. Jeffrey W. Brulet, Adam L. Borne, Kun Yuan, Adam H. Libby, Ku-Lung Hsu. Liganding Functional Tyrosine Sites on Proteins Using Sulfur–Triazole Exchange Chemistry. Journal of the American Chemical Society 2020, 142 (18) , 8270-8280. https://doi.org/10.1021/jacs.0c00648
    12. Rocco L. Policarpo, Ludovic Decultot, Elizabeth May, Petr Kuzmič, Samuel Carlson, Danny Huang, Vincent Chu, Brandon A. Wright, Saravanakumar Dhakshinamoorthy, Aimo Kannt, Shilpa Rani, Sreekanth Dittakavi, Joseph D. Panarese, Rachelle Gaudet, Matthew D. Shair. High-Affinity Alkynyl Bisubstrate Inhibitors of Nicotinamide N-Methyltransferase (NNMT). Journal of Medicinal Chemistry 2019, 62 (21) , 9837-9873. https://doi.org/10.1021/acs.jmedchem.9b01238
    13. Lucas A. Morrill, Robert B. Susick, Jason V. Chari, Neil K. Garg. Total Synthesis as a Vehicle for Collaboration. Journal of the American Chemical Society 2019, 141 (32) , 12423-12443. https://doi.org/10.1021/jacs.9b05588
    14. Yongzhi Gao, Matthijs J. van Haren, Ed E. Moret, Johannes J. M. Rood, Davide Sartini, Alessia Salvucci, Monica Emanuelli, Pierrick Craveur, Nicolas Babault, Jian Jin, Nathaniel I. Martin. Bisubstrate Inhibitors of Nicotinamide N-Methyltransferase (NNMT) with Enhanced Activity. Journal of Medicinal Chemistry 2019, 62 (14) , 6597-6614. https://doi.org/10.1021/acs.jmedchem.9b00413
    15. Sudeshna Sen, Santanu Mondal, Li Zheng, Ari J. Salinger, Walter Fast, Eranthie Weerapana, Paul R. Thompson. Development of a Suicide Inhibition-Based Protein Labeling Strategy for Nicotinamide N-Methyltransferase. ACS Chemical Biology 2019, 14 (4) , 613-618. https://doi.org/10.1021/acschembio.9b00211
    16. Heather S. Loring, Paul R. Thompson. Kinetic Mechanism of Nicotinamide N-Methyltransferase. Biochemistry 2018, 57 (38) , 5524-5532. https://doi.org/10.1021/acs.biochem.8b00775
    17. Weichao Li, Yiqing Zhou, Wenjing You, Mengquan Yang, Yanrong Ma, Mingli Wang, Yong Wang, Shuguang Yuan, Youli Xiao. Development of Photoaffinity Probe for the Discovery of Steviol Glycosides Biosynthesis Pathway in Stevia rebuadiana and Rapid Substrate Screening. ACS Chemical Biology 2018, 13 (8) , 1944-1949. https://doi.org/10.1021/acschembio.8b00285
    18. Nicolas Babault, Abdellah Allali-Hassani, Fengling Li, Jie Fan, Alex Yue, Kevin Ju, Feng Liu, Masoud Vedadi, Jing Liu, and Jian Jin . Discovery of Bisubstrate Inhibitors of Nicotinamide N-Methyltransferase (NNMT). Journal of Medicinal Chemistry 2018, 61 (4) , 1541-1551. https://doi.org/10.1021/acs.jmedchem.7b01422
    19. Hope A. Flaxman and Christina M. Woo . Mapping the Small Molecule Interactome by Mass Spectrometry. Biochemistry 2018, 57 (2) , 186-193. https://doi.org/10.1021/acs.biochem.7b01038
    20. David E. Mortenson, Gabriel J. Brighty, Lars Plate, Grant Bare, Wentao Chen, Suhua Li, Hua Wang, Benjamin F. Cravatt, Stefano Forli, Evan T. Powers, K. Barry Sharpless, Ian A. Wilson, and Jeffery W. Kelly . “Inverse Drug Discovery” Strategy To Identify Proteins That Are Targeted by Latent Electrophiles As Exemplified by Aryl Fluorosulfates. Journal of the American Chemical Society 2018, 140 (1) , 200-210. https://doi.org/10.1021/jacs.7b08366
    21. Christopher G. Parker, Christian A. Kuttruff, Andrea Galmozzi, Lars Jørgensen, Chien-Hung Yeh, Daniel J. Hermanson, Yujia Wang, Marta Artola, Steven J. McKerrall, Christopher M. Josyln, Bjarne Nørremark, Georg Dünstl, Jakob Felding, Enrique Saez, Phil S. Baran, and Benjamin F. Cravatt . Chemical Proteomics Identifies SLC25A20 as a Functional Target of the Ingenol Class of Actinic Keratosis Drugs. ACS Central Science 2017, 3 (12) , 1276-1285. https://doi.org/10.1021/acscentsci.7b00420
    22. Kenneth M. Lum, Yoshiaki Sato, Brittney A. Beyer, Warren C. Plaisted, Justin L. Anglin, Luke L. Lairson, and Benjamin F. Cravatt . Mapping Protein Targets of Bioactive Small Molecules Using Lipid-Based Chemical Proteomics. ACS Chemical Biology 2017, 12 (10) , 2671-2681. https://doi.org/10.1021/acschembio.7b00581
    23. Ludwig G. Bauer, Jennifer A. Ward, Laura Díaz‐Sáez, Yvonne Sundström, Tuomas Tolvanen, Juan Carlos Alarcón Barrera, Sarantos Kostidis, Catherine M. Rogers, Ioanna Panagakou, Usha Singh, Elisabeth M. Rothweiler, Alejandro Gonzalez Orta, H. Ümit Kaniskan, Jianping Hu, Jian Jin, Sonja Sievers, Herbert Waldmann, Martin Giera, Michael Sundström, Louise Berg, Kilian V. M. Huber. Phänomik‐basierte Entdeckung neuer orthosterischer Cholinkinase Inhibitoren. Angewandte Chemie 2025, 137 (7) https://doi.org/10.1002/ange.202420149
    24. Ludwig G. Bauer, Jennifer A. Ward, Laura Díaz‐Sáez, Yvonne Sundström, Tuomas Tolvanen, Juan Carlos Alarcón Barrera, Sarantos Kostidis, Catherine M. Rogers, Ioanna Panagakou, Usha Singh, Elisabeth M. Rothweiler, Alejandro Gonzalez Orta, H. Ümit Kaniskan, Jianping Hu, Jian Jin, Sonja Sievers, Herbert Waldmann, Martin Giera, Michael Sundström, Louise Berg, Kilian V. M. Huber. Phenomics‐Based Discovery of Novel Orthosteric Choline Kinase Inhibitors. Angewandte Chemie International Edition 2025, 64 (7) https://doi.org/10.1002/anie.202420149
    25. Jeongwoo Park, Eun Jin Shin, Tae Hyun Kim, Ji Hye Yang, Sung Hwan Ki, Keon Wook Kang, Kyu Min Kim. Exploring NNMT: from metabolic pathways to therapeutic targets. Archives of Pharmacal Research 2024, 47 (12) , 893-913. https://doi.org/10.1007/s12272-024-01519-9
    26. Rick A. Homan, John D. Lapek, Christina M. Woo, Sherry Niessen, Lyn H. Jones, Christopher G. Parker. Photoaffinity labelling with small molecules. Nature Reviews Methods Primers 2024, 4 (1) https://doi.org/10.1038/s43586-024-00308-4
    27. Antony J. Burton, Ghaith M. Hamza, Anthony A. Iannetta, Eric Miele, Andrew X. Zhang. Mass Spectrometry and Chemical Biology Approaches for Deconvoluting Epigenetic Targets. 2024, 50-83. https://doi.org/10.1039/9781837674916-00050
    28. . Emerging Technologies for Epigenetic Drug Discovery. 2024https://doi.org/10.1039/9781837674916-part2
    29. Micah J. Niphakis, Benjamin F. Cravatt. Ligand discovery by activity-based protein profiling. Cell Chemical Biology 2024, 31 (9) , 1636-1651. https://doi.org/10.1016/j.chembiol.2024.08.006
    30. Wei-Dong Sun, Xiao-Juan Zhu, Jing-Jing Li, Ya-Zhong Mei, Wen-Song Li, Jiang-Hua Li. Nicotinamide N-methyltransferase (NNMT): a novel therapeutic target for metabolic syndrome. Frontiers in Pharmacology 2024, 15 https://doi.org/10.3389/fphar.2024.1410479
    31. José M. González Dalmasy, Christina M. Fitzsimmons, William J.E. Frye, Andrew J. Perciaccante, Connor P. Jewell, Lisa M. Jenkins, Pedro J. Batista, Robert W. Robey, Michael M. Gottesman. The thiol methyltransferase activity of TMT1A (METTL7A) is conserved across species. Chemico-Biological Interactions 2024, 394 , 110989. https://doi.org/10.1016/j.cbi.2024.110989
    32. Drake A. Russell, Taeyoon Jung, Rheem A. Totah. Methyltransferases. 2024https://doi.org/10.1016/B978-0-323-95488-4.00064-4
    33. José M. González Dalmasy, Christina M. Fitzsimmons, William J.E. Frye, Andrew J. Perciaccante, Connor P. Jewell, Lisa M. Jenkins, Pedro J. Batista, Robert W. Robey, Michael M. Gottesman. The thiol methyltransferase activity of TMT1A (METTL7A) is conserved across species. 2023https://doi.org/10.1101/2023.11.17.567538
    34. Tyler Brown, Terry Nguyen, Bo Zhou, Y. George Zheng. Chemical probes and methods for the study of protein arginine methylation. RSC Chemical Biology 2023, 4 (9) , 647-669. https://doi.org/10.1039/D3CB00018D
    35. Aditi Dixit, Jeet Kalia. Protein‐Metabolite Interactions: Discovery and Significance. ChemBioChem 2023, 24 (13) https://doi.org/10.1002/cbic.202200755
    36. Yao Cheng, Haobo Wang, Hua Xu, Yuan Liu, Bin Ma, Xuemin Chen, Xin Zeng, Xianghe Wang, Bo Wang, Carina Shiau, Sergey Ovchinnikov, Xiao-Dong Su, Chu Wang. Co-evolution-based prediction of metal-binding sites in proteomes by machine learning. Nature Chemical Biology 2023, 19 (5) , 548-555. https://doi.org/10.1038/s41589-022-01223-z
    37. Felix Meissner, Jennifer Geddes-McAlister, Matthias Mann, Marcus Bantscheff. The emerging role of mass spectrometry-based proteomics in drug discovery. Nature Reviews Drug Discovery 2022, 21 (9) , 637-654. https://doi.org/10.1038/s41573-022-00409-3
    38. Isabel V. L. Wilkinson, Martin Pfanzelt, Stephan A. Sieber. Funktionalisierte Cofaktor‐Analoga für die Erforschung von Interaktomen und darüber hinaus. Angewandte Chemie 2022, 134 (29) https://doi.org/10.1002/ange.202201136
    39. Isabel V. L. Wilkinson, Martin Pfanzelt, Stephan A. Sieber. Functionalised Cofactor Mimics for Interactome Discovery and Beyond. Angewandte Chemie International Edition 2022, 61 (29) https://doi.org/10.1002/anie.202201136
    40. Xiao-Yu Li, Ya-Nan Pi, Yao Chen, Qi Zhu, Bai-Rong Xia. Nicotinamide N-Methyltransferase: A Promising Biomarker and Target for Human Cancer Therapy. Frontiers in Oncology 2022, 12 https://doi.org/10.3389/fonc.2022.894744
    41. Li Xu, Biao Peng, Haiqiang Wu, Yike Zheng, Qingwen Yu, Shuiqiao Fang. METTL7B contributes to the malignant progression of glioblastoma by inhibiting EGR1 expression. Metabolic Brain Disease 2022, 37 (4) , 1133-1143. https://doi.org/10.1007/s11011-022-00925-6
    42. Quinlin M Hanson, Min Shen, Hui Guo, Ig-Jun Cho, Matthew D Hall. Target class profiling of small molecule methyltransferases. 2022https://doi.org/10.1101/2022.03.24.485659
    43. Weixuan Wang, Changmei Yang, Tianxiang Wang, Haiteng Deng. Complex roles of nicotinamide N-methyltransferase in cancer progression. Cell Death & Disease 2022, 13 (3) https://doi.org/10.1038/s41419-022-04713-z
    44. Dhiraj P. Murale, Md Mamunul Haque, Seong Cheol Hong, Se-young Jang, Jung Hoon Lee, Seo Jeong An, Jun-Seok Lee. Development of a bifunctional BODIPY probe for mitochondria imaging and in situ photo-crosslinking in live cell. Dyes and Pigments 2021, 196 , 109830. https://doi.org/10.1016/j.dyepig.2021.109830
    45. Yongzhi Gao, Nathaniel I. Martin, Matthijs J. van Haren. Nicotinamide N-methyl transferase (NNMT): An emerging therapeutic target. Drug Discovery Today 2021, 26 (11) , 2699-2706. https://doi.org/10.1016/j.drudis.2021.05.011
    46. Richard B. Parsons, Paul D. Facey. Nicotinamide N-Methyltransferase: An Emerging Protagonist in Cancer Macro(r)evolution. Biomolecules 2021, 11 (10) , 1418. https://doi.org/10.3390/biom11101418
    47. Nikolas R. Burton, Phillip Kim, Keriann M. Backus. Photoaffinity labelling strategies for mapping the small molecule–protein interactome. Organic & Biomolecular Chemistry 2021, 19 (36) , 7792-7809. https://doi.org/10.1039/D1OB01353J
    48. Iredia D. Iyamu, Rong Huang. Mechanisms and inhibitors of nicotinamide N -methyltransferase. RSC Medicinal Chemistry 2021, 12 (8) , 1254-1261. https://doi.org/10.1039/D1MD00016K
    49. Haixiao Fang, Bo Peng, Sing Yee Ong, Qiong Wu, Lin Li, Shao Q. Yao. Recent advances in activity-based probes (ABPs) and affinity-based probes (A f BPs) for profiling of enzymes. Chemical Science 2021, 12 (24) , 8288-8310. https://doi.org/10.1039/D1SC01359A
    50. Tian-Hao Li, Cheng Qin, Bang-Bo Zhao, Hong-Tao Cao, Xiao-Ying Yang, Yuan-Yang Wang, Ze-Ru Li, Xing-Tong Zhou, Wei-Bin Wang. Identification METTL18 as a Potential Prognosis Biomarker and Associated With Immune Infiltrates in Hepatocellular Carcinoma. Frontiers in Oncology 2021, 11 https://doi.org/10.3389/fonc.2021.665192
    51. Kuan‐Yu Lin, Chak Hin Lam, Xin‐Hui Lin, Jung‐I Hsu, Syuan‐Yun Fan, Nitesh K. Gupta, Yu‐Chun Lin, Boon Khoon Tee, Jui‐Ping Li, Jen‐Kun Chen, Kui‐Thong Tan. Improved Stabilities of Labeling Probes for the Selective Modification of Endogenous Proteins in Living Cells and In Vivo. Chemistry – An Asian Journal 2021, 16 (8) , 937-948. https://doi.org/10.1002/asia.202100060
    52. Adam L. Borne, Jeffrey W. Brulet, Kun Yuan, Ku-Lung Hsu. Development and biological applications of sulfur–triazole exchange (SuTEx) chemistry. RSC Chemical Biology 2021, 2 (2) , 322-337. https://doi.org/10.1039/D0CB00180E
    53. Wei Li, Shi Xu, Naixiong Peng, Zejian Zhang, Hua He, Ruoyu Chen, Dong Chen, Jiqing Fan, Xisheng Wang. Downregulation of METTL7B Inhibits Proliferation of Human Clear Cell Renal Cancer Cells In Vivo and In Vitro. Frontiers in Oncology 2021, 11 https://doi.org/10.3389/fonc.2021.634542
    54. Jenna N. Beyer, Nicole R. Raniszewski, George M. Burslem. Advances and Opportunities in Epigenetic Chemical Biology. ChemBioChem 2021, 22 (1) , 17-42. https://doi.org/10.1002/cbic.202000459
    55. Masthan Thamim, Krishnan Thirumoorthy. Computational studies of selective N-methylation in nicotinamide: Epigenetic reprogramming in cancer. Computational and Theoretical Chemistry 2021, 1194 , 113058. https://doi.org/10.1016/j.comptc.2020.113058
    56. Anutthaman Parthasarathy, Pavan K. Mantravadi, Karunakaran Kalesh. Detectives and helpers: Natural products as resources for chemical probes and compound libraries. Pharmacology & Therapeutics 2020, 216 , 107688. https://doi.org/10.1016/j.pharmthera.2020.107688
    57. Anna Reustle, Moreno Di Marco, Carolin Meyerhoff, Annika Nelde, Juliane S. Walz, Stefan Winter, Siahei Kandabarau, Florian Büttner, Mathias Haag, Linus Backert, Daniel J. Kowalewski, Steffen Rausch, Jörg Hennenlotter, Viktoria Stühler, Marcus Scharpf, Falko Fend, Arnulf Stenzl, Hans-Georg Rammensee, Jens Bedke, Stefan Stevanović, Matthias Schwab, Elke Schaeffeler. Integrative -omics and HLA-ligandomics analysis to identify novel drug targets for ccRCC immunotherapy. Genome Medicine 2020, 12 (1) https://doi.org/10.1186/s13073-020-00731-8
    58. Hsin‐Ju Chan, Xin‐Hui Lin, Syuan‐Yun Fan, Jih Ru Hwu, Kui‐Thong Tan. Rapid and Selective Labeling of Endogenous Transmembrane Proteins in Living Cells with a Difluorophenyl Ester Affinity‐Based Probe. Chemistry – An Asian Journal 2020, 15 (21) , 3416-3420. https://doi.org/10.1002/asia.202001049
    59. Yihang Jing, Jose Montano, Michaella Levy, Jeff Lopez, Pei-Pei Kung, Paul Richardson, Krzysztof Krajewski, Laurence Florens, Michael Washburn, Jordan L. Meier. Harnessing Ionic Selectivity In Acetyltransferase Chemoproteomic Probes. 2020https://doi.org/10.1101/2020.09.24.311530
    60. Dongcheng Liu, Wei Li, Fuhua Zhong, Jianhua Yin, Wei Zhou, Shixuan Li, Xuefeng Sun, Jing Xu, Guofeng Li, Yuxin Wen, Jiaqing Wang, Malin Hong, Zhiqiang Cheng, Jimin Yuan, Lingyun Dai, Jichao Sun, Jigang Wang, Chen Qiu, Guangsuo Wang, Chang Zou. METTL7B Is Required for Cancer Cell Proliferation and Tumorigenesis in Non-Small Cell Lung Cancer. Frontiers in Pharmacology 2020, 11 https://doi.org/10.3389/fphar.2020.00178
    61. Christopher G. Parker, Matthew R. Pratt. Click Chemistry in Proteomic Investigations. Cell 2020, 180 (4) , 605-632. https://doi.org/10.1016/j.cell.2020.01.025
    62. Jason P. Holland, Melanie Gut, Simon Klingler, Rachael Fay, Amaury Guillou. Photochemical Reactions in the Synthesis of Protein–Drug Conjugates. Chemistry – A European Journal 2020, 26 (1) , 33-48. https://doi.org/10.1002/chem.201904059
    63. Toru Komatsu, Yasuteru Urano. Chemical toolbox for ‘live’ biochemistry to understand enzymatic functions in living systems. The Journal of Biochemistry 2019, 182 https://doi.org/10.1093/jb/mvz074
    64. Bumhee Lim, Jinah Lee, Byungjin Kim, Rang Lee, Jaehyun Park, Dong‐Chan Oh, Jongsik Gam, Jeeyeon Lee. Target Identification of a 1,3,4‐Oxadiazin‐5(6 H )‐One Anticancer Agent via Photoaffinity Labelling. Asian Journal of Organic Chemistry 2019, 8 (9) , 1626-1630. https://doi.org/10.1002/ajoc.201900258
    65. Chinh Ngo, Radhika Mehta, Kanchan Aggarwal, Audrey G. Fikes, Ines C. Santos, Sylvester M. Greer, Emily L. Que. Pull‐Down of Metalloproteins in Their Native States by Using Desthiobiotin‐Based Probes. ChemBioChem 2019, 20 (8) , 1003-1007. https://doi.org/10.1002/cbic.201800613
    66. Xiao Li, Chen Wang, Hao Jiang, Cheng Luo. A patent review of arginine methyltransferase inhibitors (2010–2018). Expert Opinion on Therapeutic Patents 2019, 29 (2) , 97-114. https://doi.org/10.1080/13543776.2019.1567711
    67. A. Emilia Arguello, Tharan Srikumar, Ralph E. Kleiner. A Photocrosslinking‐Based RNA Chemical Proteomics Approach to Profile m 6 A‐Regulated Protein‐RNA Interactions. Current Protocols in Nucleic Acid Chemistry 2018, 75 (1) https://doi.org/10.1002/cpnc.69
    68. Yoshihiro Sohtome, Mikiko Sodeoka. Development of Chaetocin and S ‐Adenosylmethionine Analogues as Tools for Studying Protein Methylation. The Chemical Record 2018, 18 (12) , 1660-1671. https://doi.org/10.1002/tcr.201800118
    69. Joshua J. Rosnow, Sungmin Hwang, Bryan J. Killinger, Young-Mo Kim, Ronald J. Moore, Stephen R. Lindemann, Julie A. Maupin-Furlow, Aaron T. Wright, . A Cobalamin Activity-Based Probe Enables Microbial Cell Growth and Finds New Cobalamin-Protein Interactions across Domains. Applied and Environmental Microbiology 2018, 84 (18) https://doi.org/10.1128/AEM.00955-18
    70. Hsin-Yu Lee, Radu M. Suciu, Benjamin D. Horning, Ekaterina V. Vinogradova, Olesya A. Ulanovskaya, Benjamin F. Cravatt. Covalent inhibitors of nicotinamide N-methyltransferase (NNMT) provide evidence for target engagement challenges in situ. Bioorganic & Medicinal Chemistry Letters 2018, 28 (16) , 2682-2687. https://doi.org/10.1016/j.bmcl.2018.04.017
    71. Celine Mulder, Niels Leijten, Simone Lemeer. Proteomic tools to study drug function. Current Opinion in Systems Biology 2018, 10 , 9-18. https://doi.org/10.1016/j.coisb.2018.05.002
    72. Yoshihiro Sohtome, Tadahiro Shimazu, Joaquin Barjau, Shinya Fujishiro, Mai Akakabe, Naoki Terayama, Kosuke Dodo, Akihiro Ito, Minoru Yoshida, Yoichi Shinkai, Mikiko Sodeoka. Unveiling epidithiodiketopiperazine as a non-histone arginine methyltransferase inhibitor by chemical protein methylome analyses. Chemical Communications 2018, 54 (66) , 9202-9205. https://doi.org/10.1039/C8CC03907K
    73. Sha-Sha Ge, Biao Chen, Yuan-Yuan Wu, Qing-Su Long, Yong-Liang Zhao, Pei-Yi Wang, Song Yang. Current advances of carbene-mediated photoaffinity labeling in medicinal chemistry. RSC Advances 2018, 8 (51) , 29428-29454. https://doi.org/10.1039/C8RA03538E
    74. Nan Chen, Jinmin Liu, Zeyu Qiao, Yuan Liu, Yue Yang, Changtao Jiang, Xian Wang, Chu Wang. Chemical proteomic profiling of protein N -homocysteinylation with a thioester probe. Chemical Science 2018, 9 (10) , 2826-2830. https://doi.org/10.1039/C8SC00221E
    75. Alleyn T. Plowright, Christian Ottmann, Michelle Arkin, Yves P. Auberson, Henk Timmerman, Herbert Waldmann. Joining Forces: The Chemical Biology–Medicinal Chemistry Continuum. Cell Chemical Biology 2017, 24 (9) , 1058-1065. https://doi.org/10.1016/j.chembiol.2017.05.019
    76. Magnus E. Jakobsson, Jędrzej Małecki, Benedikt S. Nilges, Anders Moen, Sebastian A. Leidel, Pål Ø. Falnes. Methylation of human eukaryotic elongation factor alpha (eEF1A) by a member of a novel protein lysine methyltransferase family modulates mRNA translation. Nucleic Acids Research 2017, 45 (14) , 8239-8254. https://doi.org/10.1093/nar/gkx432
    77. Fabian Muttach, Florian Mäsing, Armido Studer, Andrea Rentmeister. New AdoMet Analogues as Tools for Enzymatic Transfer of Photo‐Cross‐Linkers and Capturing RNA–Protein Interactions. Chemistry – A European Journal 2017, 23 (25) , 5988-5993. https://doi.org/10.1002/chem.201605663
    78. Kazuma Amaike, Tomonori Tamura, Itaru Hamachi. Recognition-driven chemical labeling of endogenous proteins in multi-molecular crowding in live cells. Chemical Communications 2017, 53 (88) , 11972-11983. https://doi.org/10.1039/C7CC07177A
    79. Matthijs J. van Haren, Rebecca Taig, Jilles Kuppens, Javier Sastre Toraño, Ed E. Moret, Richard B. Parsons, Davide Sartini, Monica Emanuelli, Nathaniel I. Martin. Inhibitors of nicotinamide N-methyltransferase designed to mimic the methylation reaction transition state. Organic & Biomolecular Chemistry 2017, 15 (31) , 6656-6667. https://doi.org/10.1039/C7OB01357D
    80. Jong-Ah Hong, Na-Eun Choi, Yeo-Kyoung La, Ho Yeon Nam, Jiwon Seo, Jiyoun Lee. Development of a smart activity-based probe to detect subcellular activity of asparaginyl endopeptidase in living cells. Organic & Biomolecular Chemistry 2017, 15 (38) , 8018-8022. https://doi.org/10.1039/C7OB01467H
    81. Miklós Bege, Ilona Bereczki, Mihály Herczeg, Máté Kicsák, Dániel Eszenyi, Pál Herczegh, Anikó Borbás. A low-temperature, photoinduced thiol–ene click reaction: a mild and efficient method for the synthesis of sugar-modified nucleosides. Organic & Biomolecular Chemistry 2017, 15 (43) , 9226-9233. https://doi.org/10.1039/C7OB02184D
    82. Toru Komatsu. Potential of Enzymomics Methodologies to Characterize Disease-Related Protein Functions. CHEMICAL & PHARMACEUTICAL BULLETIN 2017, 65 (7) , 605-610. https://doi.org/10.1248/cpb.c17-00144
    83. Dhiraj P. Murale, Seong Cheol Hong, Md. Mamunul Haque, Jun-Seok Lee. Photo-affinity labeling (PAL) in chemical proteomics: a handy tool to investigate protein-protein interactions (PPIs). Proteome Science 2016, 15 (1) https://doi.org/10.1186/s12953-017-0123-3

    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2016, 138, 40, 13335–13343
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jacs.6b07830
    Published September 30, 2016
    Copyright © 2016 American Chemical Society

    Article Views

    5666

    Altmetric

    -

    Citations

    Learn about these metrics

    Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.

    Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.

    The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.