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Assignment of Endogenous Substrates to Enzymes by Global Metabolite Profiling†

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The Skaggs Institute for Chemical Biology and Departments of Cell Biology and Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037
Cite this: Biochemistry 2004, 43, 45, 14332–14339
Publication Date (Web):October 19, 2004
https://doi.org/10.1021/bi0480335
Copyright © 2004 American Chemical Society
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    Abstract

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    Enzymes regulate biological processes through the conversion of specific substrates to products. Therefore, of fundamental interest for every enzyme is the elucidation of its natural substrates. Here, we describe a general strategy for identifying endogenous substrates of enzymes by untargeted liquid chromatography−mass spectrometry (LC−MS) analysis of tissue metabolomes from wild-type and enzyme-inactivated organisms. We use this method to discover several brain lipids regulated by the mammalian enzyme fatty acid amide hydrolase (FAAH) in vivo, including known signaling molecules (e.g., the endogenous cannabinoid anandamide) and a novel family of nervous system-enriched natural products, the taurine-conjugated fatty acids. Remarkably, the relative hydrolytic activity that FAAH exhibited for lipid metabolites in vitro was not predictive of the identity of specific FAAH substrates in vivo. Thus, global metabolite profiling establishes unanticipated connections between the proteome and metabolome that enable assignment of an enzyme's unique biochemical functions in vivo.

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    †

     This work was supported by the NIH (Grants DA015197 and DA017259), the Helen L. Dorris Child and Adolescent Neurological and Psychiatric Disorder Institute, and the Skaggs Institute for Chemical Biology. A.S. is supported by a Merck Fellowship of the Life Sciences Research Foundation.

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     To whom correspondence should be addressed. Phone:  (858) 784-8633. Fax:  (858) 784-8023. E-mail:  [email protected].

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    Tables of ion intensities, a table of exact mass data for C22:0, C24:1, and C24:0, and three figures depicting MS/MS spectra of compounds from FAAH(−/−) mice, the acyl chain distribution of NAEs and NATs, and substrate concentration versus velocity plots. This material is available free of charge via the Internet at http://pubs.acs.org.

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    64. Jasmine Chong, David S. Wishart, Jianguo Xia. Using MetaboAnalyst 4.0 for Comprehensive and Integrative Metabolomics Data Analysis. Current Protocols in Bioinformatics 2019, 68 (1) https://doi.org/10.1002/cpbi.86
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    70. Myungsun Shin, Timothy B. Ware, Hyeon-Cheol Lee, Ku-Lung Hsu. Lipid-metabolizing serine hydrolases in the mammalian central nervous system: endocannabinoids and beyond. Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids 2019, 1864 (6) , 907-921. https://doi.org/10.1016/j.bbalip.2018.08.007
    71. Yelena Sterlin, Oded Pri‐Tal, Gil Zimran, Sang‐Youl Park, Julius Ben‐Ari, Jiorgos Kourelis, Inge Verstraeten, Maayan Gal, Sean R. Cutler, Assaf Mosquna. Optimized small‐molecule pull‐downs define MLBP 1 as an acyl‐lipid‐binding protein. The Plant Journal 2019, 98 (5) , 928-941. https://doi.org/10.1111/tpj.14272
    72. Jiaqi Huang, Stephanie J Weinstein, Steven C Moore, Andriy Derkach, Xing Hua, Alison M Mondul, Joshua N Sampson, Demetrius Albanes. Pre-diagnostic Serum Metabolomic Profiling of Prostate Cancer Survival. The Journals of Gerontology: Series A 2019, 74 (6) , 853-859. https://doi.org/10.1093/gerona/gly128
    73. Robert Ramer, Rico Schwarz, Burkhard Hinz. Modulation of the Endocannabinoid System as a Potential Anticancer Strategy. Frontiers in Pharmacology 2019, 10 https://doi.org/10.3389/fphar.2019.00430
    74. Amy A. Caudy, Julia A. Hanchard, Alan Hsieh, Saravannan Shaan, Adam P. Rosebrock. Functional genetic discovery of enzymes using full-scan mass spectrometry metabolomics. Biochemistry and Cell Biology 2019, 97 (1) , 73-84. https://doi.org/10.1139/bcb-2018-0058
    75. Takashi Ito, Shigeru Murakami, Stephen W. Schaffer. Taurine-Conjugated Metabolites in Hearts. 2019, 523-529. https://doi.org/10.1007/978-981-13-8023-5_48
    76. Ewa Harasim-Symbor, Agnieszka Polak, Anna Pędzińska-Betiuk, Jolanta Weresa, Barbara Malinowska, Alicja Lewandowska, Irena Kasacka, Adrian Chabowski. Fatty acid amide hydrolase inhibitor (URB597) as a regulator of myocardial lipid metabolism in spontaneously hypertensive rats. Chemistry and Physics of Lipids 2019, 218 , 141-148. https://doi.org/10.1016/j.chemphyslip.2018.12.007
    77. Timothy B. Ware, Myungsun Shin, Ku-Lung Hsu. Metabolomics analysis of lipid metabolizing enzyme activity. 2019, 407-428. https://doi.org/10.1016/bs.mie.2019.06.027
    78. Iannotti Fabio Arturo, Piscitelli Fabiana. Endocannabinoidome. 2018, 1-10. https://doi.org/10.1002/9780470015902.a0028301
    79. Hyeon-Cheol Lee, Takehiko Yokomizo. Applications of mass spectrometry-based targeted and non-targeted lipidomics. Biochemical and Biophysical Research Communications 2018, 504 (3) , 576-581. https://doi.org/10.1016/j.bbrc.2018.03.081
    80. Viktor Brovkovych, Yasir Izhar, Jeanne M. Danes, Oleskii Dubrovskyi, Isin T. Sakallioglu, Lauren M. Morrow, G. Ekin Atilla-Gokcumen, Jonna Frasor. Fatostatin induces pro- and anti-apoptotic lipid accumulation in breast cancer. Oncogenesis 2018, 7 (8) https://doi.org/10.1038/s41389-018-0076-0
    81. Danielle M.M. Harris, Fabrice Berrué, Russell Kerr, Cheryl L. Patten. Metabolomic analysis of indolepyruvate decarboxylase pathway derivatives in the rhizobacterium Enterobacter cloacae. Rhizosphere 2018, 6 , 98-111. https://doi.org/10.1016/j.rhisph.2018.06.002
    82. Roland Wohlgemuth. Horizons of Systems Biocatalysis and Renaissance of Metabolite Synthesis. Biotechnology Journal 2018, 88 , 1700620. https://doi.org/10.1002/biot.201700620
    83. Cholsoon Jang, Li Chen, Joshua D. Rabinowitz. Metabolomics and Isotope Tracing. Cell 2018, 173 (4) , 822-837. https://doi.org/10.1016/j.cell.2018.03.055
    84. Sonia Liggi, Christine Hinz, Zoe Hall, Maria Laura Santoru, Simone Poddighe, John Fjeldsted, Luigi Atzori, Julian L. Griffin. KniMet: a pipeline for the processing of chromatography–mass spectrometry metabolomics data. Metabolomics 2018, 14 (4) https://doi.org/10.1007/s11306-018-1349-5
    85. Rico Schwarz, Robert Ramer, Burkhard Hinz. Targeting the endocannabinoid system as a potential anticancer approach. Drug Metabolism Reviews 2018, 50 (1) , 26-53. https://doi.org/10.1080/03602532.2018.1428344
    86. Takashi Ito, Koei Okazaki, Daisuke Nakajima, Daisuke Shibata, Shigeru Murakami, Stephen Schaffer. Mass spectrometry-based metabolomics to identify taurine-modified metabolites in heart. Amino Acids 2018, 50 (1) , 117-124. https://doi.org/10.1007/s00726-017-2498-y
    87. Gabriele Sulli, Amy Rommel, Xiaojie Wang, Matthew J. Kolar, Francesca Puca, Alan Saghatelian, Maksim V. Plikus, Inder M. Verma, Satchidananda Panda. Pharmacological activation of REV-ERBs is lethal in cancer and oncogene-induced senescence. Nature 2018, 553 (7688) , 351-355. https://doi.org/10.1038/nature25170
    88. Maya Saison-Ridinger, Kathleen E. DelGiorno, Tejia Zhang, Annabelle Kraus, Randall French, Dawn Jaquish, Crystal Tsui, Galina Erikson, Benjamin T. Spike, Maxim N. Shokhirev, Christopher Liddle, Ruth T. Yu, Michael Downes, Ronald M. Evans, Alan Saghatelian, Andrew M. Lowy, Geoffrey M. Wahl, . Reprogramming pancreatic stellate cells via p53 activation: A putative target for pancreatic cancer therapy. PLOS ONE 2017, 12 (12) , e0189051. https://doi.org/10.1371/journal.pone.0189051
    89. Laura R. Parisi, Nasi Li, G. Ekin Atilla-Gokcumen. Very Long Chain Fatty Acids Are Functionally Involved in Necroptosis. Cell Chemical Biology 2017, 24 (12) , 1445-1454.e8. https://doi.org/10.1016/j.chembiol.2017.08.026
    90. Joanne Tan, Armand B. Cognetta III, Diego B. Diaz, Kenneth M. Lum, Shinya Adachi, Soumajit Kundu, Benjamin F. Cravatt, Andrei K. Yudin. Multicomponent mapping of boron chemotypes furnishes selective enzyme inhibitors. Nature Communications 2017, 8 (1) https://doi.org/10.1038/s41467-017-01319-4
    91. S. Hess, G. Baker, G. Gyenes, R. Tsuyuki, S. Newman, Jean-Michel Le Melledo. Decreased serum L-arginine and L-citrulline levels in major depression. Psychopharmacology 2017, 234 (21) , 3241-3247. https://doi.org/10.1007/s00213-017-4712-8
    92. Nicholas C. Harris, Michio Sato, Nicolaus A. Herman, Frederick Twigg, Wenlong Cai, Joyce Liu, Xuejun Zhu, Jordan Downey, Ryan Khalaf, Joelle Martin, Hiroyuki Koshino, Wenjun Zhang. Biosynthesis of isonitrile lipopeptides by conserved nonribosomal peptide synthetase gene clusters in Actinobacteria. Proceedings of the National Academy of Sciences 2017, 114 (27) , 7025-7030. https://doi.org/10.1073/pnas.1705016114
    93. Michaela Aichler, Daniela Borgmann, Jan Krumsiek, Achim Buck, Patrick E. MacDonald, Jocelyn E. Manning Fox, James Lyon, Peter E. Light, Susanne Keipert, Martin Jastroch, Annette Feuchtinger, Nikola S. Mueller, Na Sun, Andrew Palmer, Theodore Alexandrov, Martin Hrabe de Angelis, Susanne Neschen, Matthias H. Tschöp, Axel Walch. N-acyl Taurines and Acylcarnitines Cause an Imbalance in Insulin Synthesis and Secretion Provoking β Cell Dysfunction in Type 2 Diabetes. Cell Metabolism 2017, 25 (6) , 1334-1347.e4. https://doi.org/10.1016/j.cmet.2017.04.012
    94. Sengan Megarajan, Pothiappan Vairaprakash, Veerappan Anbazhagan. Synthesis, characterization, and determination of critical micellar concentration and thermotropic phase transition of taurolipids. Journal of Molecular Liquids 2017, 234 , 104-110. https://doi.org/10.1016/j.molliq.2017.03.064
    95. Robert S. Jansen, Kyu Y. Rhee. Emerging Approaches to Tuberculosis Drug Development: At Home in the Metabolome. Trends in Pharmacological Sciences 2017, 38 (4) , 393-405. https://doi.org/10.1016/j.tips.2017.01.005
    96. Jing Y. Krzeszinski, Adam G. Schwaid, Wing Yin Cheng, Zixue Jin, Zachary R. Gallegos, Alan Saghatelian, Yihong Wan. Lipid Osteoclastokines Regulate Breast Cancer Bone Metastasis. Endocrinology 2017, 158 (3) , 477-489. https://doi.org/10.1210/en.2016-1570
    97. Sonia R. Salvatore, Dario A. Vitturi, Marco Fazzari, Diane K. Jorkasky, Francisco J. Schopfer. Evaluation of 10-Nitro Oleic Acid Bio-Elimination in Rats and Humans. Scientific Reports 2017, 7 (1) https://doi.org/10.1038/srep39900
    98. Robert Ramer, Burkhard Hinz. Cannabinoids as Anticancer Drugs. 2017, 397-436. https://doi.org/10.1016/bs.apha.2017.04.002
    99. Fabiana Piscitelli, Heather B. Bradshaw. Endocannabinoid Analytical Methodologies: Techniques That Drive Discoveries That Drive Techniques. 2017, 1-30. https://doi.org/10.1016/bs.apha.2017.04.003
    100. Darleny Y. Lizardo, Yen-Lung Lin, Omer Gokcumen, G. Ekin Atilla-Gokcumen. Regulation of lipids is central to replicative senescence. Molecular BioSystems 2017, 13 (3) , 498-509. https://doi.org/10.1039/C6MB00842A
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