Effect of crown ether ring size on binding and fluorescence response to saxitoxin in anthracylmethyl monoazacrown ether chemosensors
- 1 October 2006
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 84 (10), 1273-1279
- https://doi.org/10.1139/v06-093
Abstract
Convenient macrocyclization synthetic routes for the preparation of different-sized monoaza anthracylmethyl crown ether chemosensors (15-crown-5, 18-crown-6, 21-crown-7, 24-crown-8, and 27-crown-9) are described. Evaluation of these crowns as chemosensors for saxitoxin revealed that the larger crowns have moderately higher binding constants, with the 27-crown-9 chemosensor having the largest binding constant (2.29 × 105 (mol/L)–1). Fluorescence enhancements of 100% were observed at saxitoxin concentrations of 5 µmol/L, which is close to the detection limit in mouse bioassay.Key words: anthracene, crown ethers, saxitoxin, paralytic shellfish poison (PSP), binding constants; chemosensors.Keywords
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