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Related Experiment Video

Updated: Feb 3, 2026

Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization

Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization

Published on: November 29, 2018

Photoinducible Oncometabolite Detection.

Rhushikesh A Kulkarni¹, Chloe A Briney¹, Daniel R Crooks²

¹Chemical Biology Laboratory, National Cancer Institute, NIH, Frederick, MD, 21702, USA.

Chembiochem : a European Journal of Chemical Biology

|October 26, 2018

Summary

This summary is machine-generated.

Researchers developed a new chemical method to detect fumarate, an oncometabolite linked to cancer. This optical technique uses photoinducible precursors to visualize fumarate levels in cells, aiding cancer diagnosis and treatment strategies.

Keywords:

bioorthogonal chemistry cycloaddition epigenetics fluorescent detection metabolism

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Area of Science:

Biochemistry
Chemical Biology
Cancer Metabolism

Background:

Dysregulated cellular metabolism fuels cancer progression by altering bioenergetic pathways and gene expression.
Limited optical methods exist for direct metabolite detection within cells, hindering cancer research.
Fumarate is an oncometabolite implicated in various cancers, but its detection is challenging.

Purpose of the Study:

To develop an optimized chemical approach for the direct optical detection of the oncometabolite fumarate in cells.
To create a sensitive and facile method for identifying dysregulated fumarate metabolism.
To facilitate new diagnostic and therapeutic strategies for cancer.

Main Methods:

Utilized diaryl tetrazoles as cell-permeable, photoinducible precursors to nitrileimines.
Employed 1,3-dipolar cycloaddition reactions between uncaged nitrileimines and endogenous fumarate.
Formed fluorescent pyrazoline cycloadducts for detection via intrinsic fluorescence.

Main Results:

Achieved highly sensitive detection of fumarate through photolytic uncaging of diaryl tetrazoles.
Demonstrated the ability to detect dysregulated fumarate metabolism using biochemical assays.
Successfully applied the method for intracellular imaging and flow cytometry analysis of fumarate.

Conclusions:

Developed a novel bioorthogonal chemistry approach for sensitive fumarate detection.
The method enables facile biological profiling, imaging, and diagnostics related to cancer metabolism.
This strategy offers a promising tool for advancing cancer research and clinical applications.