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Synfacts 2006(11): 1126-1126  
DOI: 10.1055/s-2006-949470
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Fluorescence-Based Detection of Nitrating Agents in vivo

Contributor(s): Timothy M. Swager, Mark S. Taylor
T. Ueno, Y. Urano, H. Kojima, T. Nagano*
The University of Tokyo, CREST, JST, and Presto, JST, Saitama, Japan
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Publication History

Publication Date:
24 October 2006 (online)

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Significance

A reactivity-based probe for the detection of nitrating agents is described. Probe molecule 1 is nonfluorescent due to efficient photoinduced electron transfer from the electron-rich phenol substituent to the electron-deficient dicyano-BODIPY ring system. Upon exposure to nitrosonium tetrafluoroborate or peroxynitrite in aqueous solution, the phenol ring undergoes rapid nitration. The resulting decrease in electron density suppresses photoinduced electron-transfer, and thus the nitration product 2 is highly fluorescent.