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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Bibliographic Details
Published inCanadian journal of chemistry Vol. 84; no. 10; pp. 1273 - 1279
Main Authors Mao, Hua, Thorne, John B, Pharr, Jennifer S, Gawley, Robert E
Format Journal Article
LanguageEnglish
Published Ottawa, Canada NRC Research Press 01.10.2006
NATL RESEARCH COUNCIL CANADA-N R C RESEARCH PRESS
Subjects
Chemical properties
Chemistry
Chemistry, Multidisciplinary
Crown ethers
Paralytic shellfish poisoning
Physical Sciences
Science & Technology
Canada
anthracene
crown ethers
chemosensors
ELECTRON-TRANSFER SENSORS
GUEST
ION
binding constants
saxitoxin
SELECTIVE DETECTION
paralytic shellfish poison (PSP)
COMPLEXATION
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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.
Bibliography:Medline
NIH RePORTER
ISSN:0008-4042
1480-3291
DOI:10.1139/v06-093