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Expanded Coverage of Phytocompounds by Mass Spectrometry Imaging Using On-Tissue Chemical Derivatization by 4-APEBA
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    Expanded Coverage of Phytocompounds by Mass Spectrometry Imaging Using On-Tissue Chemical Derivatization by 4-APEBA
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    Analytical Chemistry

    Cite this: Anal. Chem. 2023, 95, 34, 12701–12709
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    https://doi.org/10.1021/acs.analchem.3c01345
    Published August 18, 2023
    Copyright © 2023 American Chemical Society

    Abstract

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    Probing the entirety of any species metabolome is an analytical grand challenge, especially on a cellular scale. Matrix-assisted laser desorption/ionization mass spectrometry imaging (MALDI-MSI) is a common spatial metabolomics assay, but this technique has limited molecular coverage for several reasons. To expand the application space of spatial metabolomics, we developed an on-tissue chemical derivatization (OTCD) workflow using 4-APEBA for the confident identification of several dozen elusive phytocompounds. Overall, this new OTCD method enabled the annotation of roughly 280 metabolites, with only a 10% overlap in metabolic coverage when compared to analog negative ion mode MALDI-MSI on serial sections. We demonstrate that 4-APEBA outperforms other derivatization agents by providing: (1) broad specificity toward carbonyls, (2) low background, and (3) introduction of bromine isotopes. Notably, the latter two attributes also facilitate more confidence in our bioinformatics for data processing. The workflow detailed here trailblazes a path toward spatial hormonomics within plant samples, enhancing the detection of carboxylates, aldehydes, and plausibly other carbonyls. As such, several phytohormones, which have various roles within stress responses and cellular communication, can now be spatially profiled, as demonstrated in poplar root and soybean root nodule.

    Copyright © 2023 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.analchem.3c01345.

    • Supporting Information contains extended methods, figures, and tables (PDF); workbook containing METASPACE annotations from all presented MALDI-MSI data sets (XLSX)

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    Cited By

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    This article is cited by 10 publications.

    1. Gregory W. Vandergrift, William Kew, Amity Andersen, Jessica K. Lukowski, Young Ah Goo, Christopher R. Anderton. Experimental and Computational Evaluation of Lipidomic In-Source Fragmentation as a Result of Postionization with Matrix-Assisted Laser Desorption/Ionization. Analytical Chemistry 2024, 96 (41) , 16127-16133. https://doi.org/10.1021/acs.analchem.4c00258
    2. Rahuljeet S Chadha, Jason A. Guerrero, Lu Wei, Laura M. Sanchez. Seeing is Believing: Developing Multimodal Metabolic Insights at the Molecular Level. ACS Central Science 2024, 10 (4) , 758-774. https://doi.org/10.1021/acscentsci.3c01438
    3. Lulu Chen, Yue Zhang, Yufen Bu, Junhui Zhou, Yi Man, Xinyuan Wu, Haobo Yang, Jinxing Lin, Xiaodong Wang, Yanping Jing, . Imaging the spatial distribution of structurally diverse plant hormones. Journal of Experimental Botany 2024, 75 (22) , 6980-6997. https://doi.org/10.1093/jxb/erae384
    4. Andreas Dannhorn, Emine Kazanc, Lucy Flint, Fei Guo, Alfie Carter, Andrew R. Hall, Stewart A. Jones, George Poulogiannis, Simon T. Barry, Owen J. Sansom, Josephine Bunch, Zoltan Takats, Richard J. A. Goodwin. Morphological and molecular preservation through universal preparation of fresh-frozen tissue samples for multimodal imaging workflows. Nature Protocols 2024, 19 (9) , 2685-2711. https://doi.org/10.1038/s41596-024-00987-z
    5. Lulu Chen, Yue Zhang, Qichen Hao, Jinxiang Fu, Zhibin Bao, Yufen Bu, Na Sun, Xinyuan Wu, Liang Lu, Zhaosheng Kong, Liang Qin, Yijun Zhou, Yanping Jing, Xiaodong Wang. Enhancement of in situ detection and imaging of phytohormones in plant tissues by MALDI ‐ MSI using 2,4‐dihydroxy‐5‐nitrobenzoic acid as a novel matrix. New Phytologist 2024, 243 (5) , 2021-2036. https://doi.org/10.1111/nph.19964
    6. Marija Veličković, Ruonan Wu, Yuqian Gao, Margaret W. Thairu, Dušan Veličković, Nathalie Munoz, Chaevien S. Clendinen, Aivett Bilbao, Rosalie K. Chu, Priscila M. Lalli, Kevin Zemaitis, Carrie D. Nicora, Jennifer E. Kyle, Daniel Orton, Sarai Williams, Ying Zhu, Rui Zhao, Matthew E. Monroe, Ronald J. Moore, Bobbie-Jo M. Webb-Robertson, Lisa M. Bramer, Cameron R. Currie, Paul D. Piehowski, Kristin E. Burnum-Johnson. Mapping microhabitats of lignocellulose decomposition by a microbial consortium. Nature Chemical Biology 2024, 20 (8) , 1033-1043. https://doi.org/10.1038/s41589-023-01536-7
    7. Nancy Shyrley García-Rojas, Carlos Daniel Sierra-Álvarez, Hilda E. Ramos-Aboites, Abigail Moreno-Pedraza, Robert Winkler. Identification of Plant Compounds with Mass Spectrometry Imaging (MSI). Metabolites 2024, 14 (8) , 419. https://doi.org/10.3390/metabo14080419
    8. Kevin J Zemaitis, Christopher R Anderton, Dusan Velickovic. A selective process for application of EDC and 4-APEBA for cabonyl containing metabolites by MALDI-MSI v1. 2024https://doi.org/10.17504/protocols.io.ewov19d9ylr2/v1
    9. Kevin J Zemaitis, Christopher R Anderton, Dusan Velickovic. A selective process for application of EDC and 4-APEBA for carbonyl containing metabolites by MALDI-MSI v2. 2024https://doi.org/10.17504/protocols.io.ewov19d9ylr2/v2
    10. Zhi Sun, Fangfang Wang, Yuwei Liu, Bowen Deng, Ruobing Ren, Yifei Wang, Di Chen, Lihua Zuo. Recent strategies for improving MALDI mass spectrometry imaging performance towards low molecular weight compounds. TrAC Trends in Analytical Chemistry 2024, 175 , 117727. https://doi.org/10.1016/j.trac.2024.117727
    11. Vimal Kumar Balasubramanian, Dušan Veličković, Maria Del Mar Rubio Wilhelmi, Christopher R. Anderton, C. Neal Stewart, Stephen DiFazio, Eduardo Blumwald, Amir H. Ahkami. Spatiotemporal metabolic responses to water deficit stress in distinct leaf cell-types of poplar. Frontiers in Plant Science 2024, 15 https://doi.org/10.3389/fpls.2024.1346853
    12. Dušan Veličković, Kevin J. Zemaitis, Arunima Bhattacharjee, Christopher R. Anderton, . Mass spectrometry imaging of natural carbonyl products directly from agar-based microbial interactions using 4-APEBA derivatization. mSystems 2024, 9 (1) https://doi.org/10.1128/msystems.00803-23
    13. Vimal Kumar Balasubramanian, Dusan Velickovic, Maria Del Mar Rubio Wilhelmi, Christopher R Anderton, C. Neal Stewart, Stephen DiFazio, Eduardo Blumwald, Amir H. Ahkami. Spatiotemporal Metabolic Responses to Water Deficit Stress in Distinct Leaf Cell-types of Poplar. 2023https://doi.org/10.1101/2023.11.30.569476

    Analytical Chemistry

    Cite this: Anal. Chem. 2023, 95, 34, 12701–12709
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.analchem.3c01345
    Published August 18, 2023
    Copyright © 2023 American Chemical Society

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