Detection of glucose in solutions also containing an alpha-hydroxy acid or a beta-diketone

• US 6,800,451 B2
• Filed: 07/03/2002
• Issued: 10/05/2004
• Est. Priority Date: 01/05/2001
• Status: Expired due to Fees

• Current Assignee: Sensors For Medicine and Science Incorporated
• Original Assignee: Sensors For Medicine and Science Incorporated
• Inventors: Daniloff, George Y., Kalivretenos, Aristotle G., Nikolaitchik, Alexandre V.
• Primary Examiner(s): GITOMER, RALPH J
• Application Number:
  US10/187,903
• Publication Number:
  US 20030082663A1
• Time in Patent Office: 825 Days
• Field of Search: 435/14, 435/190, 536/18.5, 536/18.6, 546/269.7
• US Class Current: 435/14
• CPC Class Codes: C07F 5/025 Boronic and borinic acid compounds
• CPC Class Codes: G01N 33/533 with fluorescent label
• CPC Class Codes: G01N 33/542 with steric inhibition or signal modification, e.g. fluorescent quenching
• CPC Class Codes: G01N 33/582 with fluorescent label
• CPC Class Codes: G01N 33/66 involving blood sugars, e.g. galactose
• CPC Class Codes: Y10T 436/144444 Glucose

Abstract

Compositions and methods for determining the presence or concentration of glucose in a sample which may also contain an alpha-hydroxy acid or a beta-diketone. The method uses a compound having at least two recognition elements for glucose, oriented such that the interaction between the compound and glucose is more stable than the interaction between the compound and the alpha-hydroxy acid or beta-diketone, such that the presence of the alpha-hydroxy acid or the beta-diketone does not substantially interfere with said determination.

Claims

1. A method for detecting the presence or concentration of glucose in a sample which may also contain an alpha-hydroxy acid or a beta-diketone, which comprises:

a) exposing the sample to a compound having at least two recognition elements for glucose, oriented such that the interaction between the compound and glucose is more stable than the interaction between the compound and the alpha-hydroxy acid or beta-diketone, said compound also containing a detectable moiety having a detectable quality that changes in a concentration-dependent manner when said compound is exposed to glucose in said sample; and

b) measuring any change in said detectable quality to thereby determine the presence or concentration of glucose in said sample, wherein the presence of the alpha-hydroxy acid or the beta-diketone does not substantially interfere with said determination, wherein the compound is selected from the grout consisting of;

9-[N-(2-boronobenzyl)-N-[3-(methacrylamido) propylamino]methyl]-10-[N-(2-boronobenzyl)-N-[6-(cyclohexanecarboxamido) hexylamino]methyl]anthracene;

9-[N-(2-boronobenzyl)-N-[3-(methacrylamido)propylamino]-methyl]-10-[N-(2-boronobenzyl)-N-[2-(carboxyethyl)amino]methyl]-anthracene;

9-[N-(2-boronobenzyl)-N-[3-(methacrylamido)prorylamino]-methyl]-10-(N-(2-boronobenzyl)-N-[3-(N-6-(9-anthracenecarbox-amido) hexylamino carbonyl) ethylamino]methyl]anthracene;

9-[N-(2-boronobenzyl)-N-[3-(methacrylamido)propylamino]-methyl]-10-[N-(2-boronobenzyl)-N-[6-(3-carboxypropionamido)-hexylamino]methyl]anthracene;

N-(3-Methacrylamidopropyl)-4-[2-N-[[2-(borono)benzyl]-[6-(N-[2-(borono)benzyl]-6-N-(3-carboxypropanamidoethyl)aminohexyl]]-aminoethylamino]naphthalene-1,8-dicarboximide;

N-Butyl-4-[2-N-[[2-(borono)benzyl]-[6-(N-[2-(borono)benzyl]-6-N-(2-methacrylamidoethyl) aminohexyl]]aminoethylamino]-naphthalene-1,8-dicarboximide; and

salts thereof.

2. The method of claim 1, wherein the sample is a physiological fluid.

3. The method of claim 2, wherein the physiological fluid is selected from the group consisting of blood, plasma, serum, interstitial fluid, cerebrospinal fluid, urine, saliva, intraocular fluid, lymph, tears, sweat, and physiological buffers.

4. The method of claim 1, wherein the compound is exposed to the sample in solution.

5. The method of claim 1, wherein the compound is immobilized on or within a solid support.

6. The method of claim 5 wherein the solid support is a polymeric matrix.

7. The method of claim 1, wherein the compound is associated with an implantable device, and wherein step a) takes place in viva.