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Synfacts 2008(11): 1162-1162  
DOI: 10.1055/s-0028-1083472
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

Fluorescence Indicator for Zn²+/Hg²+ Exchange

Contributor(s): Timothy M. Swager, Rebecca R. Parkhurst
J. W. Lee, H. S. Jung, P. S. Kwon, J. W. Kim*, R. A. Bartsch, Y. Kim, S.-J. Kim, J. S. Kim*
Dankook University Hospital, Cheonan and Korea University, Seoul, Korea; Texas Tech University, Lubbock, USA
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Publication History

Publication Date:
23 October 2008 (online)

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Significance

The authors synthesize 5-(4-nitro­benzene diazo)-8-benzenesulfonamidoquinaldine (NABQ) that fluoresces by an ICT (intramolecular charge transfer) mechanism. Fluorescence turns on with Zn²+ binding and turns off with Hg²+ binding. NABQ was synthesized in three steps with an overall yield of 33%. Under physiological conditions Zn²+ lead to an 11-fold increase in fluorescence, whereas Na+, K+, Ca²+, and Mg²+ had no effect. Addition of Hg²+ ions leads to irreversible fluorescence quenching.