Glucose sensing molecules having selected fluorescent...

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G01N 33/533 (2006.01) A61B 5/00 (2006.01) G01N 33/52 (2006.01) G01N 33/58 (2006.01) G01N 33/66 (2006.01)

Patent

CA 2381539

An analyte sensing fluorescent molecule that employs intramolecular electron transfer is designed to exhibit selected fluorescent properties in the presence of analytes such as saccharides. The selected fluorescent properties include excitation wavelength, emission wavelength, fluorescence lifetime, quantum yield, photostability, solubility, and temperature or pH sensitivity. The compound comprises an aryl or a substituted phenyl boronic acid that acts as a substrate recognition component, a fluorescence switch component, and a fluorophore. The fluorophore and switch component are selected such that the value of the free energy for electron transfer is less than about 3.0 kcal mol- 1. Fluorescent compounds are described that are excited at wavelengths greater than 400 nm and emit at wavelengths greater than 450 nm, which is advantageous for optical transmission through skin. The fluorophore is typically selected from transition metal-ligand complexes and thiazine, oxazine, oxazone, or oxazine-one as well as anthracene compounds. The fluorescent compound can be immobilized in a glucose permeable biocompatible polymer matrix that is implantable below the skin.

L'invention concerne une molécule fluorescente de détection d'une substance à analyser, utilisant le transfert d'électrons intramoléculaire. Cette molécule est conçue pour présenter des propriétés fluorescentes choisies en présence de substances à analyser telles que les saccharides. Ces propriétés fluorescentes choisies comprennent la longueur d'onde d'excitation, la longueur d'onde d'émission, la durée de vie de la fluorescence, le rendement quantique, la photostabilité, la solubilité, et la sensibilité à la température ou au pH. Le composé comprend un aryle ou un acide boronique substitué en phényl qui agit comme un composant reconnaissant le substrat; un composant d'activation de la fluorescence et un fluorophore. Le fluorophore et le composant d'activation sont choisis de sorte que la valeur de l'énergie libre destinée au transfert d'électrons soit inférieure à environ 3,0 kcal mol?-1¿. L'invention concerne également des composés fluorescents excités à des longueurs d'onde supérieures à 400 nm et émettant à des longueurs d'onde supérieures à 450 nm, ce qui est avantageux pour les transmissions optiques percutanées. Le fluorophore est généralement choisi parmi des complexes de transition métal-ligand et des composés de thiazine, oxazine, oxazone, ou oxazine-un ainsi que des composés d'anthracène. Le composé fluorescent peut être immobilisé dans une matrice polymère biocompatible perméable au glucose pouvant être implantée sous la peau.

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