Polymer bonded redox molecules and methods of making the same

• US 8,742,063 B2
• Filed: 05/26/2011
• Issued: 06/03/2014
• Est. Priority Date: 05/28/2010
• Status: Active Grant

• Current Assignee: Ascensia Diabetes Care Holdings AG (PHC Holdings Corporation)
• Original Assignee: Bayer Healthcare LLC (Bayer AG)
• Inventors: Fei, Jiangfeng, Chiang, William, Kerrigan, Frank, Green, Stuart, Robson, Craig, Easterfield, Howard
• Primary Examiner(s): Truong, Duc
• Application Number:
  US13/116,427
• Publication Number:
  US 20110294959A1
• Time in Patent Office: 1,104 Days
• Field of Search: 528/373, 528/377, 528/378, 528/391, 528/350, 528/351, 528/403, 528/408, 528/423
• US Class Current: 528/391
• CPC Class Codes: A61K 49/0004 Screening or testing of compounds for diagnosis of disorders, assessment of conditions, e.g. renal clearance, gastric emptying, testing for diabetes, allergy, rheuma, pancreas functions
• CPC Class Codes: C07D 279/08 condensed with carbocyclic rings or ring systems
• CPC Class Codes: C07D 279/20 with hydrogen atoms directly attached to the ring nitrogen atom
• CPC Class Codes: C07D 417/14 containing three or more hetero rings
• CPC Class Codes: C08F 8/30 Introducing nitrogen atoms or nitrogen-containing groups
• CPC Class Codes: C08F 8/34 Introducing sulfur atoms or sulfur-containing groups
• CPC Class Codes: C08G 59/4007 Curing agents not provided for by the groups C08G59/42 - C08G59/66
• CPC Class Codes: C08G 59/4064 sulfur containing compounds C08G59/4021, C08G59/4028 take precedence
• CPC Class Codes: C08G 73/024 Polyamines containing oxygen in the form of ether bonds in the main chain
• CPC Class Codes: C08G 75/24 Polysulfonates
• CPC Class Codes: C12Q 1/004 mediator-assisted
• CPC Class Codes: G01N 27/3272 Test elements therefor, i.e. disposable laminated substrates with electrodes, reagent and channels optical biosensors G01N33/52

Abstract

A non-leaching mediator may include a polymer having a polymeric backbone, and a plurality of phenothiazine groups bonded to the polymeric backbone. The plurality of phenothiazine groups may include at least one of a phenothiazine group having the general formula (IV):

and salts thereof, where n is about 9 and “R” represents the polymeric backbone to which the phenothiazine group is bonded, and a phenothiazine group having the general formula (V):

and salts thereof, where n is about 9 and “R” represents the polymeric backbone to which the phenothiazine group is bonded.

Claims

1. A polymer, comprising:

a polymeric backbone, and

a plurality of phenothiazine groups bonded to the polymeric backbone;

where the plurality of phenothiazine groups includes at least one of a phenothiazine group having the general formula (IV);

2. The polymer of claim 1, where the phenothiazine group is bonded to the polymeric backbone through a carbon-heteroatom bond.

3. The polymer of claim 1, where the phenothiazine group is bonded to the polymeric backbone through a group selected from the group consisting of an ether group, an ester group, a carbonate group, a urea group, a urethane group, an amine group, an amide group, a thioether group, a thiourea group and a sulfonamide group.

4. A method of making the polymer of claim 1, comprising:

forming the polymer from

a polymer comprising a precursor polymeric backbone and a plurality of nucleophilic side groups bonded to the precursor polymeric backbone, and

a mixture of 2-(8-(ω

-haloalkyl)-3H-phenothiazin-3-ylideneamino)benzene-1,4-disulfonic acid and 2-(2-(ω

-haloalkyl)-3H-phenothiazin-3-ylideneamino)benzene-1,4-disulfonic acid.

5. The method of claim 4, further comprising:

forming the mixture of 2-(8-(ω

-haloalkyl)-3H-phenothiazin-3-ylideneamino)-benzene-1,4-disulfonic acid and 2-(2-(ω

-haloalkyl)-3H-phenothiazin-3-ylideneamino)-benzene-1,4-disulfonic acid.

6. A method of making the polymer of claim 1, comprising:

forming the polymer from

a compound comprising a plurality of epoxide groups, and

a mixture of 2-(8-(ω

-(bis(ω

-hydroxyalkyl)amino)alkyl)-3H-phenothiazin-3-ylideneamino)benzene-1,4-disulfonic acid and 2-(2-(ω

-(bis(ω

-hydroxyalkyl)amino)alkyl)-3H-phenothiazin-3-ylideneamino)benzene-1,4-disulfonic acid.

7. The method of claim 6, further comprising:

forming the mixture of 2-(8-(ω

-(bis(ω

-hydroxyalkyl)amino)alkyl)-3H-phenothiazin-3-ylideneamino)benzene-1,4-disulfonic acid and 2-(2-(ω

-(bis(ω

-hydroxyalkyl)amino)alkyl)-3H-phenothiazin-3-ylideneamino)benzene-1,4-disulfonic acid.