Quaternary nitrogen heterocyclic compounds for detecting aqueous monosaccharides in physiological fluids

• US 8,338,602 B2
• Filed: 05/18/2010
• Issued: 12/25/2012
• Est. Priority Date: 06/27/2003
• Status: Expired due to Fees

• Current Assignee: Chris Geddes
• Original Assignee: University of Maryland Baltimore County (University of Maryland)
• Inventors: Geddes, Chris D., Badugu, Ramachandram, Lakowicz, Joseph R.
• Primary Examiner(s): Seaman, D M
• Application Number:
  US12/781,899
• Publication Number:
  US 20100297016A1
• Time in Patent Office: 952 Days
• Field of Search: 546/13, 546/339
• US Class Current: 546/13
• CPC Class Codes: A61K 49/0021 the fluorescent group being a small organic molecule
• CPC Class Codes: C07F 5/025 Boronic and borinic acid compounds
• CPC Class Codes: Y10T 436/143333 Saccharide [e.g., DNA, etc.]
• CPC Class Codes: Y10T 436/144444 Glucose
• CPC Class Codes: Y10T 436/193333 In aqueous solution

Abstract

Quaternary nitrogen heterocyclic boronic acid-containing compounds are described, which are sensitive to glucose and fructose, as well as a variety of other physiologically important analytes, such as aqueous chloride and iodide, and a method of using the compounds. Also disclosed is a contact lens doped with the quaternary nitrogen heterocyclic boronic acid-containing compound, and a method of using the doped contact lens to measure the concentration of analyte in tears under physiological conditions.

Claims

1. A fluorescence compound having the following structure:

2. The compound of claim 1, wherein the fluorescence intensity of the compound changes in the presence of glucose and wherein the fluorescence intensity of the compound decreases in the presence of glucose.

3. An assay kit for measuring the concentration of glucose in a physiological fluid comprising a container containing a fluorescence compound having the structure:

4. The kit of claim 3, wherein the physiological fluid is blood.

5. A fluorescence compound having the following structure