Claims
- 1. A polymer composition comprising a fluorescent boronic acid of the general formula:
- 2. The polymer composition of claim 1, wherein the polymer composition further includes an additional polymer that is coupled to the polymer matrix after polymerization; and wherein the additional polymer enhances the biocompatibility, swellability or hydrophllicity of the polymer composition.
- 3. The polymer composition of claim 2, wherein the polymer matrix is a block copolymer.
- 4. The polymer composition of claim 2, wherein the additional polymer is grafted on to the polymer matrix.
- 5. The polymer composition of claim 2, wherein the additional polymer is a polyethyleneoxide or polyethyleneoxide-polypropyleneoxide compound.
- 6. The polymer composition of claim 2, wherein the polymer matrix is crosslinked.
- 7. The polymer composition of claim 6, wherein the polymer matrix is crosslinked with polyethyleneoxide or polyethyleneoxide-polypropyleneoxide compounds.
- 8. The polymer composition of claim 1, wherein the nitrogen atom in the fluorescent boronic acid is covalently coupled to the polymer matrix after polymerization via the group designated R3.
- 9. The polymer composition of claim 8, wherein the atoms that link the fluorescent boronic acid to the polymer matrix of the polymer composition enhance the solubility of the polymer composition.
- 10. The polymer composition of claim 1, wherein the polymerized matrix is a polyvinylalcohol.
- 11. The polymer composition of claim 1, wherein the polymerized matrix is a polystyrene.
- 12. The polymer composition of claim 11, wherein the tether that links the polymer matrix (PM) to the fluorescent boronic acid (FBA) includes the following atoms: PM-CO-NH-FBA; PM-SO2—NH-FBA; PM-CO—NH-FBA; PM-COO-FBA; PM-NH—COO-FBA; PM-NH—CO—N-FBA or PM-NH—SO2-FBA, wherein C denotes carbon, N denotes nitrogen, 0 denotes oxygen, S denotes sulfur and H denotes hydrogen.
- 13. The polymer composition of claim 1, wherein the fluorophore is highly soluble in water.
- 14. The polymer composition of claim 13, wherein the fluorophore is Nile Blue.
- 15. A polymer composition comprising a fluorescent boronic acid and a reference fluorophore; wherein the composition is produced by a process of covalently coupling the fluorescent boronic acid and the reference fluorophore to a polymerized matrix, wherein the fluorescent boronic acid has the general formula:
- 16. The polymer composition of claim 15, wherein the polymer composition further includes an additional polymer that is covalently coupled to the polymerized matrix; and wherein the additional polymer enhances the solubility of the polymer composition.
- 17. The polymer composition of claim 16, wherein the polymerized matrix is a block copolymer.
- 18. The polymer composition of claim 16, wherein the additional polymer is grafted on to the polymerized matrix.
- 19. The polymer composition of claim 16, wherein the additional polymer is a polyethyleneoxide or polyethyleneoxide-polypropyleneoxide compound.
- 20. The polymer composition of claim 16, wherein the polymerized matrix is crosslinked.
- 21. The polymer composition of claim 20, wherein the polymerized matrix is crosslinked with polyethyleneoxide or polyethyleneoxide-polypropyleneoxide compounds.
- 22. The polymer composition of claim 15, wherein the nitrogen atom in the fluorescent boronic acid is covalently coupled to the polymerized matrix via the group designated R3.
- 23. The polymer composition of claim 22, wherein the atoms that link the fluorescent boronic acid to the polymerized matrix of polymer composition enhance the solubility of the polymer composition.
- 24. The polymer composition of claim 15, wherein the polymerized matrix is a polyvinylalcohol.
- 25. The polymer composition of claim 15, wherein the polymerized matrix is a polystyrene.
- 26. The polymer composition of claim 25, wherein the tether that links the polymer matrix (PM) to the fluorescent boronic acid (FBA) includes the following atoms: PM-CO—NH-FBA; PM—SO2-NH-FBA; PM-CO—NH-FBA; PM-COO-FBA; PM-NH—COO-FBA; PM-NH—CO—N-FBA or PM-NH—SO2-FBA, wherein C denotes carbon, N denotes nitrogen, O denotes oxygen, S denotes sulfur and H denotes hydrogen.
- 27. The polymer composition of claim 15, wherein the fluorophore is highly soluble in water.
- 28. The polymer composition of claim 27, wherein the fluorophore is Nile Blue.
- 29. A method of making a polymer composition comprising a fluorescent boronic acid and a reference fluorophore, the method comprising the steps of:
covalently coupling the fluorescent boronic acid and the reference fluorophore to a polymerized matrix, wherein the fluorescent boronic acid has the general formula: 7wherein: F is a fluorophore; N is a nitrogen atom; B is a boron atom; R1 is selected ftom the functional group consisting of hydrogen, aliphatic and aromatic groups, wherein the functional group (R1O)2B is capable of binding glucose; R2, R3 and R4 are optional and independent hydrogen, aliphatic or aromatic groups, further functionalized aliphatic or aromatic groups or groups that are capable of forming a covalent linkage to the polymer matrix; L1 and L2 are optional linking groups having from zero to four atoms selected from the group consisting of nitrogen, carbon, oxygen, sulfur and phosphorous; and
wherein the polymer composition including the covalently coupled reference fluorophore and the covalently coupled fluorescent boronic acid is soluble in an aqueous environment; and the fluorescence of the polymer composition including the covalently coupled reference fluorophore and the covalendy coupled fluorescent boronic acid increases in the presence of bound glucose.
- 30. The method of claim 29, further including the step of covalently coupling an additional polymer to the polymerized matrix; and wherein the additional polymer enhances the solubility of the polymer composition.
- 31. The method of claim 30, wherein the additional polymer is grafted on to the polymerized matrix.
- 32. The method of claim 31, wherein the additional polymer is a polyethyleneoxide or polyethyleneoxide-polypropyleneoxide compound.
- 33. The method of claim 29, further including the step of covalently crosslinking the polymer composition.
- 34. The method of claim 33, wherein the polymer matrix is crosslinked with polyethyleneoxide or polyethyleneoxide-polypropyleneoxide compounds.
- 35. The method of claim 29, wherein the nitrogen atom in the fluorescent boronic acid is covalently coupled to the polymerized matrix via the group designated R3.
- 36. The method of claim 35, wherein the atoms that link the fluorescent boronic acid to the polymerized matrix of polymer composition enhance the solubility of the polymer composition.
- 37. The method of claim 29, wherein the polymerized matrix is a polyvinylalcohol.
- 38. The method of claim 29, wherein the polymerized matrix is a polystyrene.
- 39. The method of claim 38, wherein the atomic group that is used to covalently couple the fluorescent boronic acid (FBA) to the polymer matrix (PM) is: HO—(CH2)-FBA; NH2—(CH2)-FBA or NH2—(CH2)—(O—CH2)-FBA wherein H is hydrogen, C is carbon, N is nitrogen, O is oxygen and n is an integer greater than or equal to 1.
- 40. The method of claim 38, wherein the tether that links the polymer matrix (PM) to the fluorescent boronic acid (FBA) includes the following atoms: PM-CO—NH-FBA; PM-SO2—NH-FBA; PM-CO—NH-FBA; PM-COO-FBA; PM-NH—COO-FBA; PM-NH—CO—N-FBA or PM-NH—SO2-FBA, wherein C denotes carbon, N denotes nitrogen, O denotes oxygen, S denotes sulfut and H denotes hydrogen.
- 41. The method of claim 29, wherein the fluorophore is highly soluble in water.
- 42. The method of claim 42, wherein the fluorophore is Nile Blue.
- 43. A method of coupling a fluorescent boronic acid (FBA) compound to a polymerized matrix (PM) to generate a polymerized matrix composition (PMC), wherein the fluorescent boronic acid compound has the general formula:
RELATED APPLICATIONS
[0001] This application claims priority under Section 119(e) from U.S. Provisional Application Serial No. 60/269,226, filed Feb. 15, 2001; and this application is related to U.S. patent application Ser. No. 08/721,262, filed Sept. 26, 1996, now U.S. Pat. No. 5,777,060 which is a Continuation-in-Part of U.S. patent application Ser. No. 08/410,775, filed Mar. 27, 1995, now abandoned; and this application is related to U.S. patent application Ser. No. 09/934,390, filed Aug. 21, 2001, which is a Divisional application of U.S. patent application Ser. No. 09/401,147, filed Sept. 22, 1999 which is a Continuation Application of U.S. patent application Ser. No. 08/752,945, filed Nov. 21, 1996, now U.S. Pat. No. 6,011,984, which is a Continuation-in-Part of U.S. Provisional Application Serial No. 60/007,515; and this application is related to U.S. patent application Ser. No. 10/033,240, filed Dec. 28, 2001; and this application is related to U.S. patent application Ser. No. 09/823,522, filed Mar. 30, 2001, which claims priority to provisional application No. 60/194,673, filed Apr. 4, 2000, and is a Continuation-in-part Application of U.S. patent application Ser. No. 09/663,567, filed Sept. 15, 2000, which claims priority to provisional application number 60/154,103, filed Sept. 15, 1999; the disclosures of each of which are incorporated herein by reference.
Provisional Applications (1)
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Number |
Date |
Country |
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60269226 |
Feb 2001 |
US |