Method for detecting polyhydroxyl compounds

• US 5,137,833 A
• Filed: 09/21/1989
• Issued: 08/11/1992
• Est. Priority Date: 09/21/1989
• Status: Expired due to Term

• Current Assignee: Medtronic Minimed Incorporated (Medtronic Plc)
• Original Assignee: Anthony P. Russell
• Inventors: Russell, Anthony P.
• Primary Examiner(s): Lee, Mary C.
• Assistant Examiner(s): POWERS, FIONA
• Application Number:
  US07/410,657
• Time in Patent Office: 1,055 Days
• Field of Search: 534/573 P, 534/582, 534/583, 534/692, 534/694, 534/713, 534/726, 436/95, 436/57, 436/94, 436/172, 436/800, 436/131
• US Class Current: 436/94
• CPC Class Codes: G01N 33/521 Single-layer analytical elements
• CPC Class Codes: G01N 33/523 the element being adapted for a specific analyte
• CPC Class Codes: G01N 33/66 involving blood sugars, e.g. galactose
• CPC Class Codes: Y10T 436/143333 Saccharide [e.g., DNA, etc.]
• CPC Class Codes: Y10T 436/203332 Hydroxyl containing

Abstract

A method for detecting and measuring the concentration in solution of polyhydroxyl compounds, such as sugars. The invention makes use of certain dyes that, when linked to a derivative of boronic acid (or boronate ion), arsenious acid (or arsenite ion), or germanic acid (or germanate ion), exhibit quantitative responses to the presence of polyhydroxyl species.

Claims

1. A method of detecting the presence of vicinal polyhydroxyl compounds in a solvent, comprising the steps of:

a. establishing the emission characteristics, as a function of polyhydroxyl-compound concentration, of a dye compound comprising a binding moiety selected from the group consisting of boronic acid, boronate ion, arsenious acid, arsenite ion, telluric acid, tellurate ion, germanic acid and germanic ion, covalently linked to a chemical group such that the compound exhibits the properties of a fluorescent dye and wherein binding of said compound to a compound containing vicinal hydroxyl groups results in quantitative attenuation of dye properties;

b. contacting said solvent with a sample carrier;

c. introducing said dye into said solvent;

d. without removing the unbound dye, determining the concentration of polyhydroxyl compound by measuring at least one characteristic of the emitted radiation, the characteristic being selected from the intensity and wavelength.

4. The method of claim 1 wherein said binding moiety is selected from the group consisting of m-aminophenylboronic acid, m-aminophenylboronate, m-aminophenylarsenious acid, m-aminophenylarsenite, m-aminophenyltelluric acid, m-aminophenyltellurate, m-aminophenylgermanic acid and m-aminophenylgermanate.

7. The method of claim 1 wherein said one or more polyhydroxyl compound are monosaccharides or disaccharides.

2. A method of detecting the presence of vicinal polyhydroxyl compounds in a solvent, comprising the steps of:

a. contacting said solvent with a sample carrier;

b. introducing into said solvent a fluorescent dye compound comprising a binding moiety selected from the group consisting of boronic acid, boronate ion, arsenious acid, arsenite ion, telluric acid, tellurate ion, germanic acid and germanate ion, covalently linked to a chemical group such that the compound exhibits the properties of a fluorescent dye and wherein biding of said compound to a compound containing vicinal hydroxyl groups results in attenuation of dye properties;

c. without removing the unbound dye, measuring at least one characteristic of the emitted radiation, the characteristic being selected from the intensity and wavelength,

wherein the step of introducing said dye compound into said solvent is accomplished by means of test paper to which said dye compound has been bound.

3. A method of detecting the presence of vicinal polyhydroxyl compounds in a solvent, comprising the steps of:

a. contacting said solvent with a sample carrier;

b. introducing into said solvent a fluorescent dye compound comprising a binding moiety selected from the group consisting of boronic acid, boronate ion, arsenious acid, arsenite ion, telluric acid, tellurate ion, germanic acid and germanate ion, covalently linked to a chemical group such that the compound exhibits the properties of a fluorescent dye and wherein biding of said compound to a compound containing vicinal hydroxyl groups results in attenuation of dye properties;

c. without removing the unbound dye, measuring at least one characteristic of the emitted radiation, the characteristic being selected from the intensity and wavelength,

wherein the step of introducing said dye compound into said solvent is accomplished by means of fiber-optic material to which said dye compound has been bound.

5. A method of detecting the presence of vicinal polyhydroxyl compounds in a solvent, comprising the steps of:

a. contacting said solvent with a sample carrier;

b. introducing into said solvent a fluorescent dye compound comprising a binding moiety selected from the group consisting of boronic acid, boronate ion, arsenious acid, arsenite ion, telluric acid, tellurate ion, germanic acid and germanate ion, covalently linked to a chemical group such that the compound exhibits the properties of a fluorescent dye and wherein biding of said compound to a compound containing vicinal hydroxyl groups results in attenuation of dye properties;

c. without removing the unbound dye, measuring at least one characteristic of the emitted radiation, the characteristic being selected from the intensity and wavelength,

wherein the dye compound is prepared by diazotizing an aryl compound selected from the group consisting of m-aminophenylboronic acid, m-aminophenylboronate, m-aminophenylarsenious acid, m-aminophenylarsenite, m-aminophenyltelluric acid, m-aminophenyltellurate, m-aminophenylgermanic acid and m-aminophenylgermanate, and coupling said diazotized aryl compound to an electron donating species, such that the compound formed thereby exhibits the properties of a dye and wherein binding of said compound to a polyhydroxyl compound results in attenuation of the dye properties of said compound.

6. The method of claim 5 wherein said electron donating species is selected from the group consisting of m-aminophenylboronic acid, m-aminophenylboronate, m-aminophenylarsenious and animated polystyrene polymers and copolymers.

8. A method of detecting the presence of vicinal polyhydroxyl compounds in a solvent, comprising the steps of:

a. contacting said solvent with a sample carrier;

b. introducing into said solvent a dye compound comprising a binding moiety selected from the group consisting of boronic acid, boronate ion, arsenious acid, arsenite ion, telluric acid, tellurate ion, germanic acid and germanate ion, covalently linked to a chemical group such that the compound exhibits the properties of a dye and wherein binding of said compound to a compound containing vicinal hydroxyl groups results in attenuation of dye properties;

c. exposing said sample carrier and said solvent to radiation; and

d. measuring the intensity of the radiation passing through the sample relative to that impinging on the sample,

wherein the step of introducing said dye compound into said solvent is accomplished by means of polymeric material to which said dye compound has been bound.

9. The method of claim 8 wherein said polymeric material is test paper.

10. A method of detecting the presence of vicinal polyhydroxyl compounds in a solvent, comprising the steps of:

a. contacting said solvent with a sample carrier;

b. introducing into said solvent a dye compound comprising a binding moiety selected from the group consisting of boronic acid, boronate ion, arsenious acid, arsenite ion, telluric acid, tellurate ion, germanic acid and germanate ion, covalently linked to a chemical group such that the compound exhibits the properties of a dye and wherein binding of said compound to a compound containing vicinal hydroxyl groups results in attenuation of dye properties;

c. exposing said sample carrier and said solvent to radiation; and

d. measuring the intensity of the radiation passing through the sample relative to that impinging on the sample,

wherein the step of introducing said dye compound into said solvent is accomplished by means of fiber-optic material to which said dye compound has been bound.

11. A method of detecting the presence of vicinal polyhydroxyl compounds in a solvent, comprising the steps of:

a. contacting said solvent with a sample carrier;

b. introducing into said solvent a dye compound comprising a binding moiety selected from the group consisting of boronic acid, boronate ion, arsenious acid, arsenite ion, telluric acid, tellurate ion, germanic acid and germanate ion, covalently linked to a chemical group such that the compound exhibits the properties of a dye and wherein biding of said compound to a compound containing vicinal hydroxyl groups results in attenuation of dye properties;

c. exposing said sample carrier and said solvent to radiation; and

d. measuring the intensity of the radiation passing through the sample relative to that impinging on the sample,

wherein the dye compound is prepared by diazotizing an aryl compound selected from the group consisting of m-aminophenylboronic acid, m-aminophenylboronate, m-aminophenylarsenious acid, m-aminophenylarsenite, m-aminophenyltelluric acid, m-aminophenyltellurate, m-aminophenylgermanic acid and m-aminophenylgermanate, and coupling said diazotized aryl compound to an electron donating species, such that the compound formed thereby exhibits the properties of a dye and wherein binding of said compound to a polyhydroxyl compound results in attenuation of the dye properties of said compound.

12. The method of claim 11 wherein said electron donating species is selected from the group consisting of m-aminophenylboronic acid, m-aminophenylboronate, and animated polystyrene polymers and copolymers.