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J Am Chem Soc. 2002 Nov 13;124(45):13448-53.

Chemosensors for the marine toxin saxitoxin.

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Department of Chemistry, and NIEHS Marine and Freshwater Biomedical Sciences Center, University of Miami, P.O. Box 249118, Coral Gables, Florida 33124-0431, USA.


Eleven anthracylmethyl crown ethers have been synthesized and evaluated as fluorescence sensors for the marine toxin saxitoxin. Fluorescence enhancement data are consistent with a 1:1 binding complex for all crowns. The binding constants are in the range of 10(4) M(-)(1) in ammonium phosphate buffer (pH 7.1) in 80% ethanol solvent. Selectivity for sensing saxitoxin versus several organic analytes has been demonstrated for the first time. Possible modes of binding are presented, and relevance to saxitoxin monitoring programs are discussed.

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