HPTS-Mono and BIS Cys-Ma polymerizable fluorescent dyes for use in analyte sensors

• US 7,824,918 B2
• Filed: 08/06/2008
• Issued: 11/02/2010
• Est. Priority Date: 08/06/2007
• Status: Active Grant

• Current Assignee: Medtronic Minimed Incorporated (Medtronic Plc)
• Original Assignee: GluMetrics, Inc.
• Inventors: Suri, Jeff T.
• Primary Examiner(s): Soderquist; Arlen
• Application Number:
  US12/187,248
• Publication Number:
  US 20090061528A1
• Time in Patent Office: 818 Days
• Field of Search: 422/68.1, 422 8205- 8208, 436 94- 95, 436/166, 436/172, 562/14, 562 30- 31, 562/35, 562/37, 562 43- 44, 562/80, 562/89, 562/430, 564/15, 564 83- 84, 564/89
• US Class Current: 436/95
• CPC Class Codes: C09B 57/001 Pyrene dyes
• CPC Class Codes: C09B 69/109 containing other specific dyes
• CPC Class Codes: Y10T 436/143333 Saccharide [e.g., DNA, etc.]
• CPC Class Codes: Y10T 436/144444 Glucose

Abstract

Novel fluorescent dyes are disclosed for use in analyte detection. In particular, mono- and bis-substituted HPTS dyes and methods of making them are provided.

Claims

1. The compound

2. The compound of claim 1, wherein the anionic group is sulfonic acid.

3. The compound of claim 1 wherein said reactive group is an ethylenically unsaturated polymerizable group selected from the group consisting of acryloyl, methacryloyl, acrylamide, methacrylamido and styryl.

4. The compound of claim 1 wherein said reactive group comprises a coupling group selected from the group consisting of a carboxylic acid, aldehyde, alkyne, azide, activated ester, succinimide and nitrobenzoate, and wherein said coupling group is capable of binding the compound to a polymer or substrate.

5. The compound of claim 1, wherein R¹ and R² are bonded together in a cyclic structure.

19. The compound of claim 1 or 14 comprising L, D, or L and D sterioisomers of cysteic acid.

20. A hydrogel comprising a compound of claim 1 or 14.

21. A glucose sensor comprising a compound of claim 1 or claim 14.

22. The glucose sensor of claim 21, further comprising a quencher moiety comprising boronic acid.

23. The glucose sensor of claim 22, wherein said quencher moiety comprising boronic acid is 3,3′

-oBBV;

24. A hydrogel comprising a glucose sensor of claim 21.

6. The compound:

7. The compound:

8. The compound:

9. The compound:

10. The compound:

11. A method of making the compound of claim 10, wherein M is Na, comprising the steps of:

27. The compound of claim 10, 12 or 25, wherein M is Na.

12. The compound:

13. A method of making the compound of claim 12, wherein M is Na, comprising the steps of:

14. The compound:

15. The compound of claim 14, wherein the anionic group is sulfonic acid.

16. The compound of claim 14 wherein said reactive group is an ethylenically unsaturated polymerizable group selected from the group consisting of acryloyl, methacryloyl, acrylamide, methacrylamido and styryl.

17. The compound of claim 14 wherein said reactive group comprises a coupling group selected from the group consisting of a carboxylic acid, aldehyde, alkyne, azide, activated ester, succinimide and nitrobenzoate, and wherein said coupling group is capable of binding the compound to a polymer or substrate.

18. The compound of claim 14, wherein R¹ and R² are bonded together in a cyclic structure.

25. The compound:

26. A method of making the compound of claim 25, wherein M is Na, comprising the steps of:

28. The compound:

29. The compound:

30. The compound:

31. The compound: