ArticleJournal of the American Chemical Society2016
Co-opting a Bioorthogonal Reaction for Oncometabolite Detection.
Article in Journal of the American Chemical Society, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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Who cites it
12 citing papers in PubMed, 31 citations in OpenAlex.
- Profiling the proteome-wide selectivity of diverse electrophiles.Nature chemistry · 2025Article
- Cryptic splice mutation in the fumarate hydratase gene in patients with clinical manifestations of Hereditary Leiomyomatosis and Renal Cell Cancer.Human molecular genetics · 2023Article
- Fluorogenic Reactions in Chemical Biology: Seeing Chemistry in Cells.Chemical & biomedical imaging · 2023Review
- Research Progress and Application of Bioorthogonal Reactions in Biomolecular Analysis and Disease Diagnosis.Topics in current chemistry (Cham) · 2021Review
- Light-Triggered Click Chemistry.Chemical reviews · 2021Review
- Photocaged Cell-Permeable Ubiquitin Probe for Temporal Profiling of Deubiquitinating Enzymes.Journal of the American Chemical Society · 2020Article
- Light-Activatable, 2,5-Disubstituted Tetrazoles for the Proteome-wide Profiling of Aspartates and Glutamates in Living Bacteria.ACS central science · 2020Article
- Epigenetic regulation by endogenous metabolite pharmacology.Current opinion in chemical biology · 2019Review
- A chemoproteomic portrait of the oncometabolite fumarate.Nature chemical biology · 2019Article
- Photoinducible Oncometabolite Detection.Chembiochem : a European journal of chemical biology · 2019Article
- Bioorthogonal oncometabolite ligation.Methods in enzymology · 2019Article
- The Future of Bioorthogonal Chemistry.ACS central science · 2018Review
Corrections and comments
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Authors and funding
10 authors at 2 institutions in 1 country.
Funding
Abstract
Dysregulated metabolism is a hallmark of many diseases, including cancer. Methods to fluorescently detect metabolites have the potential to enable new approaches to cancer detection and imaging. However, fluorescent sensing methods for naturally occurring cellular metabolites are relatively unexplored. Here we report the development of a chemical approach to detect the oncometabolite fumarate. Our strategy exploits a known bioorthogonal reaction, the 1,3-dipolar cycloaddition of nitrileimines and electron-poor olefins, to detect fumarate via fluorescent pyrazoline cycloadduct formation. We demonstrate hydrazonyl chlorides serve as readily accessible nitrileimine precursors, whose reactivity and spectral properties can be tuned to enable detection of fumarate and other dipolarophile metabolites. Finally, we show this reaction can be used to detect enzyme activity changes caused by mutations in fumarate hydratase, which underlie the familial cancer predisposition syndrome hereditary leiomyomatosis and renal cell cancer. Our studies define a novel intersection of bioorthogonal chemistry and metabolite reactivity that may be harnessed to enable biological profiling, imaging, and diagnostic applications.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.