Transition metal complexes with (pyridyl)imidazole ligands

• US 7,074,308 B2
• Filed: 11/14/2003
• Issued: 07/11/2006
• Est. Priority Date: 05/11/2001
• Status: Expired due to Term

• Current Assignee: Abbott Diabetes Care Incorporated (Abbott Laboratories Incorporated)
• Original Assignee: Therasense Incorporated (Abbott Laboratories Incorporated)
• Inventors: Heller, Adam, Mao, Fei
• Primary Examiner(s): Olsen, Kaj K.
• Application Number:
  US10/714,835
• Publication Number:
  US 20040099529A1
• Time in Patent Office: 970 Days
• Field of Search: 204/403.1, 204/403.04, 204/403.14, 204/418, 526/161, 546/2, 548/101
• US Class Current: 204/403.14
• CPC Class Codes: C07F 15/0026 without a metal-carbon linkage

Abstract

Novel transition metal complexes of iron, cobalt, ruthenium, osmium, and vanadium are described. The transition metal complexes can be used as redox mediators in enzyme-based electrochemical sensors. The transition metal complexes include substituted or unsubstituted (pyridyl)imidazole ligands. Transition metal complexes attached to polymeric backbones are also described.

Claims

1. A complex having the formula:

2. The complex of claim 1, wherein R₇ is a C5 alkyl.

3. The complex of any one of claims 1 and 2, wherein R₈ is methyl.

4. The complex of any one of claims 1 and 2, wherein a combination of R₉ and R₁₀ forms a fused, saturated or unsaturated, 6-membered ring.

5. The complex of any one of claims 1 and 2, wherein a combination of R₉ and R₁₀ forms a fused, unsaturated, 6-membered ring.

6. The complex of any one of claims 1 and 2, wherein L₂ is —

F, —

Cl, or —

Br.

7. The complex of any one of claims 1 and 2, wherein L₂ is —

Cl.

8. The complex of any one of claims 1 and 2, wherein R′

₁ is a C1–

C2 alkyl.

9. The complex of any one of claims 1 and 2, wherein R′

₁ is a Cl alkyl.

10. The complex of any one of claims 1 and 2, wherein each of R_a and R_c is —

H.

11. The complex of any one of claims 1 and 2, wherein each of R_a, R_b, and R_c is —

H.

12. The complex of any one of claims 1 and 2, wherein each of R_a, R_b, R_c, and R_d is —

H.

13. The complex of any one of claims 1 and 2, wherein X is a halide.

14. The complex of any one of claims 1 and 2, wherein X is chloride.

17. The complex of any one of claims 1, 2, 15, and 16, wherein at least one ligand selected from L, L′

, L₁ and L₂ is coupled to a polymeric backbone.

18. The complex of claim 17, wherein the polymeric backbone comprises at least one functional group that is a ligand of the complex.

19. The complex of claim 18, wherein the functional group is selected from pyridine and imidazole groups.

20. A sensor comprising:

a working electrode;

a counter electrode;

an enzyme disposed proximate to the working electrode; and

the complex of any one of claims 1, 2, 15, and 16 disposed proximate to the working electrode.

21. The sensor of claim 20, wherein the complex is coupled to a polymeric backbone via at least one ligand selected from L, L′

, L₁ and L₂.

22. The sensor of claim 21, wherein the polymeric backbone comprises at least one functional group that is a ligand of the complex.

23. The sensor of claim 22, wherein the functional group is selected from pyridine and imidazole groups.

24. The sensor of claim 20, wherein the complex is crosslinked on the working electrode.

25. The sensor of claim 20, wherein the complex and the enzyme are crosslinked on the working electrode.

15. A complex having the formula:

16. The complex of claim 15, wherein R₇ is a C5 alkyl.