Fluorescent probes for saccharrides

• US 20040087842A1
• Filed: 05/30/2003
• Published: 05/06/2004
• Est. Priority Date: 05/30/2002
• Status: Abandoned Application

• Current Assignee: Joseph R. Lakowicz, Nicolas Dicesare
• Original Assignee: Joseph R. Lakowicz, Nicolas Dicesare
• Inventors: Dicesare, Nicolas, Lakowicz, Joseph R.
• Application Number:
  US10/448,430
• Publication Number:
  US 20040087842A1
• Time in Patent Office: Days
• US Class Current: 600/317
• 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 formula

2. The fluorescent compound of claim 1 which is represented by the formula

3. The fluorescent compound of claim 2 which is represented by a chemical formula selected from the group consisting of

4. The fluorescent compound of claim 2 which is represented by the chemical formula

5. The fluorescent compound of claim 2 which is represented by the chemical formula

6. The fluorescent compound of claim 1 which is represented by the chemical formula

8. The compound of claim 1, wherein the compound is attached to a solid support.

9. The compound of claim 1, wherein the compound is immobilized in a polymer matrix.

10. The compound of claim 8, wherein the compound is covalently attached to the solid support.

11. The compound of claim 9, wherein the compound is covalently attached to the polymer matrix.

12. The compound of claim 9, wherein the compound is embedded within the polymer matrix.

13. The compound of claim 9, wherein the matrix is biocompatable.

14. 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 1;

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.

15. The method of claim 14 wherein the diol is a sugar.

16. The method of claim 15 wherein the sugar is selected from the group consisting of glucose, fructose and galactose.

17. The method of claim 14 wherein said change is a change in the intensity of fluorescence of said compound.

18. The method of claim 14 wherein said change is a change in the lifetime of fluorescence of said compound.

19. The method of claim 14 wherein said change is a change in the intensity ratio of said compound.

20. A method as in claim 14 which is performed in vivo in an animal.

21. A method as in claim 14 wherein said measuring step comprises a measurement of the anisotropy or polarization of the fluorescence emitted by the compound.

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

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

24. A method as in claim 14 wherein said measuring step comprises a measurement of the anisotropy differential phase angle of the fluorescence emitted by the compound.

25. A method as in claim 14 wherein said measuring step comprises a measurement of the anisotropy modulation ratio of the fluorescence emitted by the compound.

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

49. A kit for detecting the presence of a diol in a sample which comprises a compound as in claim 1 and packaging material, and optionally labeling material and instructions for using said compound to detect the presence of the diol.

50. A kit as in claim 49 wherein the compound is bound to a solid support.

7. A fluorescent compound represented by the chemical formula

27. 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 7;

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.

28. The method of claim 27 wherein the diol is a sugar.

29. The method of claim 28 wherein the sugar is selected from the group consisting of glucose, fructose and galactose.

30. The method of claim 27 wherein said change is a change in the intensity of fluorescence of said compound.

31. The method of claim 27 wherein said change is a change in the lifetime of fluorescence of said compound.

32. The method of claim 27 wherein said change is a change in the intensity ratio of said compound.

33. A method as in claim 27 which is performed in vivo in an animal.

34. A method as in claim 27 wherein said measuring step comprises a measurement of the anisotropy or polarization of the fluorescence emitted by the compound.

35. A method as in claim 27 wherein said measuring step comprises a measurement of the anisotropy decay time of the fluorescence emitted by the compound.

36. A method as in claim 27 wherein said measuring step comprises a measurement of the anisotropy correlation time of the fluorescence emitted by the compound.

37. A method as in claim 27 wherein said measuring step comprises a measurement of the anisotropy differential phase angle of the fluorescence emitted by the compound.

38. A method as in claim 27 wherein said measuring step comprises a measurement of the anisotropy modulation ratio of the fluorescence emitted by the compound.

39. A method as in claim 27 wherein said measuring step comprises a measurement of the modulated anisotropy of the fluorescence emitted by the compound.

51. A kit for detecting the presence of a diol in a sample which comprises a compound as in claim 7 and packaging material, and optionally labeling material and instructions for using said compound to detect the presence of the diol.

52. A kit as in claim 51 wherein the compound is bound to a solid support.

40. 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 a compound selected from the group consisting of

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

41. The method of claim 40 wherein the diol is a sugar.

42. The method of claim 41 wherein the sugar is selected from the group consisting of glucose, fructose and galactose.

43. A method as in claim 40 which is performed in vivo in an animal.

44. A method as in claim 40 wherein said change is a change in the intensity ratio of said compound.

45. A method as in claim 40 wherein said measuring step comprises a measurement of the anisotropy or polarization of the fluorescence emitted by the compound.

46. A method as in claim 40 wherein said measuring step comprises a measurement of the anisotropy decay time of the fluorescence emitted by the compound.

47. A method as in claim 40 wherein said measuring step comprises a measurement of the anisotropy correlation time of the fluorescence emitted by the compound.

48. A method as in claim 40 wherein the animal is a human.

53. A kit for detecting the presence of a diol in a sample which comprises a compound as in claim 40 and packaging material, and optionally labeling material and instructions for using said compound in a method as in claim 40.

54. A kit as in claim 53 wherein the compound is bound to a solid support.