Effect of crown ether ring size on binding and fluorescence response to saxitoxin in anthracylmethyl monoazacrown ether chemosensors

by Mao, H.; Thorne, J. B.; Pharr, J. S.; Gawley, R. E.

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 x 10(5) (mol/L)(-1)). Fluorescence enhancements of 100% were observed at saxitoxin concentrations of 5 mu mol/L, which is close to the detection limit in mouse bioassay.

Journal
Canadian Journal of Chemistry-Revue Canadienne de Chimie
Volume
84
Issue
10
Year
2006
Start Page
1273-1279
URL
https://dx.doi.org/10.1139/v06-093
ISBN/ISSN
1480-3291; 0008-4042
DOI
10.1139/v06-093