Fluorescent probes for saccharrides

• US 7,635,595 B2
• Filed: 03/10/2005
• Issued: 12/22/2009
• Est. Priority Date: 05/30/2002
• Status: Expired due to Fees

• Current Assignee: Joseph R. Lakowicz, Nicolas Dicesare
• Original Assignee: Joseph R. Lakowicz, Nicolas Dicesare
• Inventors: Lakowicz, Joseph R., Dicesare, Nicolas
• Primary Examiner(s): Soderquist; Arlen
• Application Number:
  US11/075,817
• Publication Number:
  US 20050158245A1
• Time in Patent Office: 1,748 Days
• Field of Search: 250/485.1, 250/459.1, 422/61, 436 94- 95, 436/131, 436/172, 600316-317, 600/319, 548/110, 548/215, 548/235, 548/239, 558286-288, 562/7, 564 8- 11, 564/305, 568/1, 568/6
• US Class Current: 436/94
• CPC Class Codes: A61B 5/14532 for measuring glucose, e.g. by tissue impedance measurement
• CPC Class Codes: C07F 5/025 Boronic and borinic acid compounds
• CPC Class Codes: G01N 31/22 using chemical indicators G01N31/02 takes precedence
• CPC Class Codes: Y10T 436/143333 Saccharide [e.g., DNA, etc.]
• CPC Class Codes: Y10T 436/144444 Glucose
• CPC Class Codes: Y10T 436/203332 Hydroxyl containing

Abstract

The spectroscopic and photophysical properties of fluorescent probes comprising donor-acceptor derivatives comprising the boric acid group or a derivative of boric acid, B(OH)₃ (or borate ion, BO(OH)₂⁻¹), arsenious acid, H₃ AsO₃ (or arsenite ion, H₂AsO₃⁻¹), telluric acid, H₆TeO₆ (or tellurate ion, H₅ TeO₆⁻¹) or germanic acid, Ge(OH)₆ (or germanate ion, GeO(OH)₃⁻¹) are described. Method of using said probes are also provided.

Claims

1. A fluorescent compound which is represented by the chemical formula

2. A fluorescent compound which is represented by the chemical formula

3. A fluorescent compound which is represented by the chemical formula

4. A fluorescent compound represented by the chemical formula

5. A method for detecting the presence or concentration of a diol in a sample which comprises the following steps:

a) contacting the sample with a probe which comprises the compound of claim 4; and

b) measuring any change in fluorescence emitted by the probe upon binding of the diol to the probe, thereby detecting the presence or concentration of the diol.

6. The method of claim 5 wherein the diol is a sugar.

7. The method of claim 6 wherein the sugar is selected from the group consisting of glucose, fructose and galactose.

8. The method of claim 5 wherein said change is a change in the intensity of fluorescence of said compound.

9. The method of claim 5 wherein said change is a change in the lifetime of fluorescence of said compound.

10. The method of claim 5 wherein said change is a change in the intensity ratio of said compound.

11. A method as in claim 5 which is performed in vivo in an animal.

12. A method as in claim 5 wherein said measuring step comprises a measurement of the anisotropy or polarization of the fluorescence emitted by the compound.

13. A method as in claim 5 wherein said measuring step comprises a measurement of the anisotropy decay time of the fluorescence emitted by the compound.

14. A method as in claim 5 wherein said measuring step comprises a measurement of the anisotropy correlation time of the fluorescence emitted by the compound.

15. A method as in claim 5 wherein said measuring step comprises a measurement of the anisotropy differential phase angle of the fluorescence emitted by the compound.

16. A method as in claim 5 wherein said measuring step comprises a measurement of the anisotropy modulation ratio of the fluorescence emitted by the compound.

17. A method as in claim 5 wherein said measuring step comprises a measurement of the modulated anisotropy of the fluorescence emitted by the compound.

18. A kit for detecting the presence of a diol in a sample which comprises a compound as in claim 4 and packaging material, and optionally labeling material and instructions for using said compound to detect the presence of the diol.

19. A kit as in claim 18 wherein the compound is bound to a solid support.