Title: Glucose sensing molecules having selected fluorescent properties

Abstract

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.sup.-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.

Inventors:

Satcher, Jr., Joe H.; Lane, Stephen M.; Darrow, Christopher B.; Cary, Douglas R.; Tran, Joe Anh

Issue Date:

Tue Jan 27 00:00:00 EST 2004

Research Org.:

University Of California, The Regents Of, Oakland, CA (United States); Lawrence Livermore National Laboratory (LLNL), Livermore, CA (United States)

Sponsoring Org.:

USDOE

OSTI Identifier:

1174703

Patent Number(s):

6682938

Application Number:

09/663,567

Assignee:

University Of California, The Regents Of

Patent Classifications (CPCs):

A - HUMAN NECESSITIES A61 - MEDICAL OR VETERINARY SCIENCE A61B - DIAGNOSIS

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07F - ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM

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A - HUMAN NECESSITIES A61 - MEDICAL OR VETERINARY SCIENCE A61B - DIAGNOSIS

A61B5/14532 - {for measuring glucose, e.g. by tissue impedance measurement}
A61B5/1459 - invasive, e.g. introduced into the body by a catheter {

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07F - ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM

C07F5/025 - {Boronic and borinic acid compounds}

C - CHEMISTRY C09 - DYES C09B - ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS},

C09B19/00 - Oxazine dyes
C09B57/08 - Naphthalimide dyes
C09B57/10 - Metal complexes of organic compounds not being dyes in uncomplexed form

G - PHYSICS G01 - MEASURING G01N - INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES

G01N33/52 - Use of compounds or compositions for colorimetric, spectrophotometric or fluorometric investigation, e.g. use of reagent paper {and including single- and multilayer analytical elements
G01N33/66 - involving blood sugars, e.g. galactose

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DOE Contract Number:  

W-7405-ENG-48

Resource Type:

Patent

Country of Publication:

United States

Language:

English

Subject:

42 ENGINEERING