Analyte sensor incorporating negatively charged moieties

• US 9,739,746 B1
• Filed: 12/23/2013
• Issued: 08/22/2017
• Est. Priority Date: 12/23/2013
• Status: Active Grant

• Current Assignee: Google LLC (Alphabet Inc.)
• Original Assignee: Google Inc. (Alphabet Inc.)
• Inventors: Liu, Zenghe, Yao, Huanfen
• Primary Examiner(s): Kaur, Gurpreet
• Application Number:
  US14/138,373
• Time in Patent Office: 1,338 Days
• CPC Class Codes: G01N 27/3275 Sensing specific biomolecules, e.g. nucleic acid strands, based on an electrode surface reaction

Abstract

An analyte sensor and a method for making the analyte sensor are disclosed. The analyte sensor includes a crosslinked, hydrophilic copolymer having a methacrylate-derived backbone and a side chain having a negatively charged group. The copolymer can include an embedded analyte sensing component, and can be adjacent to a surface of an electrode, or be adjacent to a sensing membrane that that has an embedded analyte sensing component and is adjacent to a surface of an electrode. The sensing membrane can have a crosslinked network of crosslinked proteins.

Claims

1. A crosslinked, hydrophilic copolymer comprising:

backbone chains comprising;

first methacrylate-derived units, each having a hydrophilic side chain;

second methacrylate-derived units having the structure of formula (III);

2. An analyte sensor comprising:

an analyte sensing component embedded within the crosslinked, hydrophilic copolymer of claim 1, wherein the crosslinked, hydrophilic copolymer is adjacent to an electrode.

3. The analyte sensor claim 2, wherein the analyte sensing component comprises glucose oxidase.

4. An analyte sensor comprising:

a sensing membrane comprising;

a crosslinked network comprising one or more proteins and crosslinks, wherein the proteins are crosslinked through carbon-nitrogen double bonds between amine group nitrogen atoms on the proteins and carbon atoms on the crosslinks, and an analyte sensing component embedded in the crosslinked network; and

a crosslinked, hydrophilic copolymer of claim 1,

wherein the sensing membrane is adjacent to an electrode.

5. The analyte sensor of claim 4, wherein the sensing membrane is between the electrode and the crosslinked, hydrophilic copolymer.

6. The analyte sensor of claim 2, wherein the first methacrylate-derived units have the structure of formula (Ia):

7. The analyte sensor of claim 6, wherein the first methacrylate-derived units have the structure:

8. The analyte sensor of claim 2, wherein L is C₁-C₆alkyl or —

O—

C₁-C₆alkyl, where C₁-C₆alkyl is methylene, ethylene, propylene, butylene, pentylene or hexylene.

9. The analyte sensor of claim 2, wherein the second methacrylate-derived units have the structure of formula (IIIa):

10. The analyte sensor of claim 2, further comprising fourth methacrylate-derived units, each having a hydrophilic side chain that is different than the hydrophilic side chain of the first methacrylate-derived unit.

11. The analyte sensor of claim 10, wherein the fourth methacrylate-derived units have the structure of formula (II):

13. The analyte sensor of claim 10, wherein

the first methacrylate-derived units are derived from 2-hydroxyethylmethacrylate;

the fourth methacrylate-derived units have the structure of formula (II);

14. The analyte sensor of claim 4, wherein in the crosslinks are C₂-C₆alkyl.

15. The analyte sensor of claim 4, wherein the proteins are bovine serum albumin.

16. The analyte sensor according to claim 4, wherein the analyte sensing component comprises glucose oxidase.

17. The analyte sensor of claim 4, wherein the crosslinked, hydrophilic copolymer further comprises fourth methacrylate-derived units, each having a hydrophilic side chain that is different than the hydrophilic side chains of the first methacrylate-derived unit.

18. The analyte sensor of claim 17, wherein

the proteins are BSA;

the crosslinks are C₂-C₆alkyl;

the analyte sensing component comprises glucose oxidase;

the first methacrylate-derived units are derived from 2-hydroxyethylmethacrylate;

the fourth methacrylate-derived units have the structure of formula (II);

19. The analyte sensor of claim 2, wherein the second methacrylate-derived units have the structure of formula (III):

20. The analyte sensor of claim 4, wherein the second methacrylate-derived units have the structure of formula (III):

21. The analyte sensor of claim 4, wherein the second methacrylate-derived units have the structure of formula (IIIa):

12. The analyte sensor of 10, wherein the fourth methacrylate-derived units have the structure of formula (II):