ArticleChembiochem : a European journal of chemical biology2019
Photoinducible Oncometabolite Detection.
Article in Chembiochem : a European journal of chemical biology, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed.
- Rewiring of RNA methylation by the oncometabolite fumarate in renal cell carcinoma.NAR cancer · 2024Article
- Cryptic splice mutation in the fumarate hydratase gene in patients with clinical manifestations of Hereditary Leiomyomatosis and Renal Cell Cancer.Human molecular genetics · 2023Article
- Light-Triggered Click Chemistry.Chemical reviews · 2021Review
- Bioorthogonal chemistry.Nature reviews. Methods primers · 2021Article
- Photocaged Cell-Permeable Ubiquitin Probe for Temporal Profiling of Deubiquitinating Enzymes.Journal of the American Chemical Society · 2020Article
- Heterogeneous adaptation of cysteine reactivity to a covalent oncometabolite.The Journal of biological chemistry · 2020Article
- An Oncometabolite Isomer Rapidly Induces a Pathophysiological Protein Modification.ACS chemical biology · 2020Article
- Epigenetic regulation by endogenous metabolite pharmacology.Current opinion in chemical biology · 2019Review
- Bioorthogonal oncometabolite ligation.Methods in enzymology · 2019Article
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Authors and funding
11 authors.
Funding
Abstract
Dysregulated metabolism can fuel cancer by altering the production of bioenergetic building blocks and directly stimulating oncogenic gene-expression programs. However, relatively few optical methods for the direct study of metabolites in cells exist. To address this need and facilitate new approaches to cancer treatment and diagnosis, herein we report an optimized chemical approach to detect the oncometabolite fumarate. Our strategy employs diaryl tetrazoles as cell-permeable photoinducible precursors to nitrileimines. Uncaging these species in cells and cell extracts enables them to undergo 1,3-dipolar cycloadditions with endogenous dipolarophile metabolites such as fumarate to form pyrazoline cycloadducts that can be readily detected by their intrinsic fluorescence. The ability to photolytically uncage diaryl tetrazoles provides greatly improved sensitivity relative to previous methods, and enables the facile detection of dysregulated fumarate metabolism through biochemical activity assays, intracellular imaging, and flow cytometry. Our studies showcase an intersection of bioorthogonal chemistry and metabolite reactivity that can be applied for biological profiling, imaging, and diagnostics.
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