Effect of crown ether ring size on binding and fluorescence response to saxitoxin in anthracylmethyl monoazacrown ether chemosensors
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 crown...
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Published in | Canadian journal of chemistry Vol. 84; no. 10; pp. 1273 - 1279 |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
Published |
Ottawa, Canada
NRC Research Press
01.10.2006
NATL RESEARCH COUNCIL CANADA-N R C RESEARCH PRESS |
Subjects | |
Online Access | Get full text |
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Summary: | 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 × 10
5
(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. |
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Bibliography: | Medline NIH RePORTER |
ISSN: | 0008-4042 1480-3291 |
DOI: | 10.1139/v06-093 |