Mediators suitable for the electrochemical regeneration of NADH, NADPH or analogs thereof

• US 5,393,615 A
• Filed: 02/03/1994
• Issued: 02/28/1995
• Est. Priority Date: 02/03/1994
• Status: Expired due to Term

• Current Assignee: Miles, Inc. (Bayer AG)
• Original Assignee: Miles, Inc. (Bayer AG)
• Inventors: Musho, Matthew K., Corey, Paul F.
• Primary Examiner(s): GORGOS, KATHRYN L
• Application Number:
  US08/190,855
• Time in Patent Office: 390 Days
• Field of Search: 204/403, 204/418, 204/290 R, 435/877, 435/888, 429/43, 429/50
• US Class Current: 429/401
• CPC Class Codes: C12Q 1/004 mediator-assisted
• CPC Class Codes: H01M 4/9008 Organic or organo-metallic compounds
• 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

Abstract

Disclosed is the use of 9H-acridin-2-one and 11H-dibenz-[b,f][1,4]oxazepin-8-one compounds as mediators suitable for the electrochemical regeneration of the co-enzymes dihydronicotinamide adenine dinucleotide (NADH), dihydronicotinamide adenine dinucleotide phosphate (NADPH) or analogs thereof.

Claims

1. An electrode having a surface used for electrochemical regeneration of coenzymes dihydronicotinamide adenine dinucleotide (NADH), dihydronicotinamide adenine dinucleotide phosphate (NADPH) or analogs thereof characterized in that there has been imparted to the electrode surface a mediator function comprising one or more mediator compounds selected from the group consisting of substituted or unsubstituted 9H-acridin-2-ones and 11H-dibenz[b,e][1,4,]oxazepine-2-ones.

2. An electrode as characterized by claim 1 wherein the mediator is characterized by the formula:

##STR9## wherein X is ##STR10## where R'"'"' and R" are lower alkyl of 1 to 6 carbon atoms ##STR11## Y and Z are independently H or another monovalent substituent, Q is (→

O)_n where n=0 or 1 and R is H or lower alkyl of 1 to 6 carbon atoms.

3. The electrode of claim 2 wherein Y and Z are independently hydrogen, substituted or unsubstituted aryl, alkoxy, aryloxy, halo, nitro, substituted amino, keto, carboxy, alkoxycarbonyl or amino.

4. The electrode of claim 1 wherein one or more enzyme are present at the electrode surface.

5. The electrode of claim 4 wherein the enzyme is a dehydrogenase.

6. The electrode of claim 1 wherein the electrode is comprised of graphite, pyrolytic carbon, glassy carbon, platinum or gold.

7. The electrode of claim 1 wherein the mediator compound is 7-hydroxy-9,9-dimethyl-9H-acridin-2-one.

8. A method of improving the performance of a biochemical fuel cell which operates with dehydrogenase as a catalyst and a co-enzyme as an energy-transferring redox couple, which method involves using the electrode described in claim 1 as an anode in said fuel cell.

9. The method of claim 8 wherein the mediator compound is:

##STR12## wherein X is ##STR13## where R'"'"' and R" are lower alkyl of 1 to 6 carbon atoms or ##STR14## Y and Z are independently H or another monovalent substituent, Q is (→

O)_n where n=0 or 1 and R is H or lower alkyl of 1 to 6 carbon atoms.

10. The method of claim 8 wherein the electrode is comprised of graphite, pyrolytic carbon, glassy carbon, platinum or gold and the mediator compound is 7-hydroxy-9,9-dimethyl-9H-acridin-2-one.