Electron mediator, electron mediator immobilized electrode, and biofuel cell using the electrode

• US 20050049313A1
• Filed: 03/23/2004
• Published: 03/03/2005
• Est. Priority Date: 09/02/2003
• Status: Active Grant

• Current Assignee: Sekisui Medical Company Limited (Sekisui)
• Original Assignee: Daiichi Pure Chemicals Co., Ltd.
• Inventors: Fukasaku, Noboru, Kosuge, Jun-ichi, Nishizawa, Matsuhiko, Matsue, Tomokazu
• Granted Patent: US 7,544,438 B2
• Time in Patent Office: Days
• US Class Current: 514/682
• CPC Class Codes: C07C 235/78 the carbon skeleton containing rings
• CPC Class Codes: C07C 66/02 Anthraquinone carboxylic acids
• CPC Class Codes: H01M 8/16 Biochemical fuel cells, i.e. cells in which microorganisms function as catalysts
• CPC Class Codes: Y02E 60/50 Fuel cells
• CPC Class Codes: Y10S 435/817 Enzyme or microbe electrode

Abstract

An object of the present invention is to provide a highly functional mediator capable of smoothly proceeding electron transfer between an electrode and a biocatalyst based on the premise that the mediator excels in safety and cost and to provide an electrode and a cell with sufficient amount of such a mediator molecule immobilized efficiently and strongly. The present invention provides a mediator mediating electron transfer between an enzyme and an electrode and containing a quinone molecule derivative, in particular, a mediator containing a VK₃ derivative. In addition, the present invention provides an electrode and a biofuel cell to which those mediators are applied.

Claims

1. A mediator which mediates electron transfer between an enzyme and an electrode, comprising a quinone molecule derivative.

2. A mediator according to claim 1, wherein the quinone molecule derivative is a naphthoquinone molecule derivative.

3. A mediator according to claim 2, wherein the naphthoquinone molecule derivative is one or more kinds of a naphthoquinone molecule chosen from the group consisting of a sodium anthraquinone-2-sulfonate (AQS) derivative and a 2-methyl-1,4-naphthoquionone (VK₃) derivative.

4. A mediator according to claim 2, wherein the naphthoquinone molecule derivative is a 2-methyl-1,4-naphthoquinone (VK₃) derivative.

5. A mediator according to claim 4, wherein the 2-methyl-1,4-naphthoquinone (VK₃) derivative is 2-methyl-1,4-naphthoquinone (VK₃) modified with one or more kinds of a functional group selected from the group consisting of an amino group, a carboxyl group, a chloroformyl group, a succinimide oxycarbonyl group, an alkyl metal sulfosuccinimide oxycarbonyl group, a pentafluorophenyl oxycarbonyl group, a p-nitrophenyl oxycarbonyl group, a hydroxyl group, a formyl group, a halogen group, a maleimide group, an isothiocyanate group, and an oxiranyl group.

6. A mediator according to claim 5, wherein the 2-methyl-1,4-naphthoquinone (VK3) derivative is one or more kinds of a quinone molecule selected from the group consisting of 2-(3-carboxypropyl)-3-methyl-1,4-naphthoquinone (CPVK₃) represented by the following formula (1), 2-{3-[N-(2-aminoethyl)aminocarbonyl]propyl}-3-methyl-1,4-naphthoquinone (AEACPVK₃) represented by the following formula (2), and 2-(3-aminopropyl)-3-methyl-1,4-naphthoquinone (APVK₃) represented by the following formula (3).

7. An electrode comprising a mediator according to any one of claims 1 to 6 immobilized.

8. An electrode according to claim 7, further comprising an enzyme immobilized.

9. An electrode according to claim 8, wherein the enzyme contains diaphorase.

10. An electrode according to claim 8, wherein the enzyme contains diaphorase and dehydrogenase.

11. An electrode according to claim 10, wherein the dehydrogenase is glucose dehydrogenase.

12. An electrode according to claim 10 or 11, further comprising NADH immobilized.

13. An electrode according to claim 8 comprising the mediator and the enzyme immobilized on the electrode by a polymer and a crosslinking agent.

14. An electrode according to claim 13, wherein the polymer is polyvinylimidazole.

15. An electrode according to claim 13 or 14, wherein the crosslinking agent is polyethylene glycol diglycidyl ether (PEGDGE).

16. An electrode according to claim 7, further comprising an oxygen separation membrane arranged in a vicinity of the mediator.

17. An electrode according to claim 7, used for one of a biofuel cell and a biosensor.

18. A biofuel cell including an enzyme, a substrate (fuel), and electrodes and utilizing electron transfer among the enzyme, the substrate (fuel), and the electrodes for electricity generation, comprising a cathode and an anode according to claim 7 for the electrodes.

19. A biofuel cell according to claim 18, wherein the substrate (fuel) is glucose.

20. A biofuel cell according to claim 18 or 19, wherein the cathode contains polydimethylsiloxane immobilized.

21. 2-{3-[N-(2-aminoethyl)aminocarbonyl]propyl}-3-methyl-1,4-naphthoquinone (AEACPVK₃) represented by the following formula (2).