Fluorescent dyes for use in glucose sensing

• US 7,417,164 B2
• Filed: 07/24/2007
• Issued: 08/26/2008
• Est. Priority Date: 07/25/2006
• Status: Active Grant

• Current Assignee: Medtronic Minimed Incorporated (Medtronic Plc)
• Original Assignee: GluMetrics, Inc.
• Inventors: Suri, Jeff T.
• Primary Examiner(s): O SULLIVAN, PETER G
• Application Number:
  US11/782,553
• Publication Number:
  US 20080027245A1
• Time in Patent Office: 399 Days
• Field of Search: 564/15, 564/83, 562/14, 562/31, 562/35, 562/43, 562/44, 562/430, 600/316, 600/317, 436/95
• US Class Current: 562/31
• CPC Class Codes: C09B 57/001 Pyrene dyes
• CPC Class Codes: C12Q 1/54 involving glucose or galactose
• CPC Class Codes: G01N 33/52 Use of compounds or compositions for colorimetric, spectrophotometric or fluorometric investigation, e.g. use of reagent paper and including single- and multilayer analytical elements immunological elements G01N33/54386; involving labelled immunochemicals G01N33/58; for haemoglobin or occult blood G01N33/72
• CPC Class Codes: G01N 33/531 Production of immunochemical test materials
• CPC Class Codes: G01N 33/66 involving blood sugars, e.g. galactose
• CPC Class Codes: Y10T 436/144444 Glucose

Abstract

A novel class of compounds that includes HPTS-Cys-MA, and methods of making them are disclosed herein. The class of compounds including HPTS-Cys-MA are useful as fluorescent dyes for analyte detection.

Claims

1. The compound:

6. A glucose sensor comprising the compound of claim 1.

7. The glucose sensor of claim 6, further comprising a quencher moiety.

8. The glucose sensor of claim 7, wherein said quencher moiety comprises boronic acid.

9. The glucose sensor of claim 8, wherein said boronic acid quencher is 3,3′

-oBBV.

10. A method of making the compound of claim 1, comprising the steps of:

2. The compound:

11. A method of making the compound of claim 2, comprising the steps of:

3. The compound:

4. The compound of claim 3, wherein NBu₄ is any other counterion.

5. The compound of claim 3, comprising L, D, or L and D stereoisomers of cysteine.

12. A method of making the compound of claim 3, comprising the steps of making HPTS-CysOH as follows;

and

13. A method of making the compound of claim 3, comprising the steps of:

making TBCys as follows;