Azo mediators and methods of use thereof

• US 9,840,729 B2
• Filed: 03/27/2014
• Issued: 12/12/2017
• Est. Priority Date: 09/28/2011
• Status: Active Grant

• Current Assignee: Roche Diabetes Care Inc. (Roche Holding AG)
• Original Assignee: Roche Diabetes Care Inc. (Roche Holding AG)
• Inventors: Duvall, Stacy H., Gebauer, Peter, Heindl, Dieter, Horn, Carina, Kratzsch, Peter, Marquant, Michael, Meier, Thomas
• Primary Examiner(s): Kosack, Joseph R
• Application Number:
  US14/226,884
• Publication Number:
  US 20140212903A1
• Time in Patent Office: 1,356 Days
• CPC Class Codes: C07C 281/20 the two nitrogen atoms of the functional groups being doubly-bound to each other, e.g. azoformamide
• CPC Class Codes: C07D 295/215 Radicals derived from nitrogen analogues of carbonic acid
• CPC Class Codes: C12Q 1/54 involving glucose or galactose

Abstract

Azo compounds are disclosed that do not form azoxy dimers and that do not have any reactive nitroso groups. Also disclosed are use of the azo compounds as mediators in optical and electrochemical diagnostic methods, as well as detection reagents, kits and test elements that include such azo compounds and that can be used in the diagnostic methods.

Claims

1. A detection reagent for determining presence or concentration of glucose, the detection reagent comprising:

(a) a flavine-, nicotinamide- or pyrroloquinoline quinone-dependent oxidoreductase;

(b) a reducible flavine, nicotinamide or pyrroloquinoline quinone coenzyme;

(c) an azo compound of the general formula (I);

2. The detection reagent of claim 1, wherein the flavine-, nicotinamide- or pyrroloquinoline quinone-dependent oxidoreductase is a flavine-, nicotinamide- or pyrroloquinoline quinone-dependent dehydrogenase.

3. The detection reagent of claim 2, wherein the flavine-, nicotinamide- or pyrroloquinoline quinone-dependent glucose dehydrogenase is a glucose-6-phosphate dehydrogenase.

4. The detection reagent of claim 1, wherein the reducible flavine, nicotinamide or pyrroloquinoline quinone coenzyme is selected from the group consisting of carbaNAD⁺, carbaNADP⁺, FAD, FMN, NAD⁺, NADP⁺, PQQ and derivatives thereof.

5. The detection reagent of claim 1, wherein the azo compound is 4-[bis-(2-hydroxyethyl)-amino]-benzenediazocarbamide.

6. A kit for determining presence or concentration of glucose, the kit comprising:

(a) the detection reagent of claim 1; and

(b) an optical test element or an electrochemical test element.

7. A test element for determining presence or concentration of glucose, the test element comprising the detection reagent of claim 1.

8. The test element of claim 6, wherein the test element is an optical sensor or an electrochemical sensor.

9. A method of determining presence or concentration of glucose, the method comprising the steps of:

(a) contacting a sample comprising glucose with the test element of claim 7; and

(b) determining a presence and/or a concentration of glucose in the sample.