Pyridinium boronic acid quenchers for use in analyte sensors

• US 7,939,664 B2
• Filed: 05/01/2008
• Issued: 05/10/2011
• Est. Priority Date: 05/01/2007
• Status: Active Grant

• Current Assignee: Medtronic Minimed Incorporated (Medtronic Plc)
• Original Assignee: GluMetrics, Inc.
• Inventors: Wessling, Ritchie A., Gamsey, Soya
• Primary Examiner(s): AULAKH, CHARANJIT
• Application Number:
  US12/113,876
• Publication Number:
  US 20080305009A1
• Time in Patent Office: 1,104 Days
• Field of Search: 546/13, 424/9.6, 424/9.1
• US Class Current: 546/13
• CPC Class Codes: C07F 5/025 Boronic and borinic acid compounds
• CPC Class Codes: G01N 2400/00 Assays, e.g. immunoassays or enzyme assays, involving carbohydrates
• CPC Class Codes: G01N 33/523 the element being adapted for a specific analyte
• CPC Class Codes: Y10T 436/104998 Glucose, ketone, nitrate standard or control
• CPC Class Codes: Y10T 436/144444 Glucose
• CPC Class Codes: Y10T 436/145555 Hetero-N

Abstract

Novel pyridinium salts functionalized with boronic acid and methods of making them are disclosed. When combined with a fluorescent dye, the compounds are useful in the detection of polyhydroxyl-substituted organic molecules.

Claims

1. The reactive compound:

2. The compound of claim 1, wherein Z is a reactive, ethylenically unsaturated group selected from the group consisting of methacrylamido-, acrylamido-, methacryloyl-, acryloyl- and styryl-.

3. The compound of claim 1, wherein Z is a reactive functional group capable of forming a covalent bond with a polymer or matrix selected from the group consisting of —

Br, —

OH, —

SH, —

CO₂H, and —

NH₂.

4. The compound of claim 1, wherein Z is

5. The reactive compound of claim 1, wherein said compound is:

6. A method of making the compound of claim 5, comprising the steps of:

20. A glucose sensor comprising one or more of the compounds of any one of the claims 1, 4, 5, 7, 10, 12, 13, and 15-18, and a fluorescent dye.

21. The glucose sensor of claim 20, wherein said one or more of the compounds are in the form of a polymer.

22. The glucose sensor of claim 20, further comprising a glucose permeable immobilizing means, e.g., a polymer matrix or a semipermeable membrane.

7. The compound:

8. The compound of claim 7, wherein Z is a polymerizable, ethylenically unsaturated group selected from the group consisting of methacrylamido-, acrylamido-, methacryloyl-, acryloyl- and styryl-.

9. The compound of claim 7, wherein Z is a reactive functional group capable of forming a covalent bond with a polymer or matrix selected from the group consisting of —

Br, —

OH, —

SH, —

CO₂H, and —

NH₂.

10. The compound:

11. A method of making the compound of claim 10, comprising the steps of:

12. The compound:

13. The compound:

14. A method of making the compound of claim 13, comprising the steps of:

15. The compound:

16. The compound of claim 15, wherein Z is

17. The compound of claim 15, wherein Z is selected from the group consisting of —

Br, —

OH, —

SH, —

CO₂H, and —

NH₂.

18. The compound:

19. A method of making the compound of claim 18, comprising the steps of: