Polymers functionalized with fluorescent boronate motifs and methods for making them
First Claim
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1. A polymer composition comprising a fluorescent boronic acid of the general formula:
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wherein;
F is a fluorophore;
N is a nitrogen atom;
B is a boron atom;
R1 is selected from 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, wherein the polymerized matrix is a polystyrene or a polyvinylalcohol;
L1 and L2 ate 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 futher includes a reference fluorophore; and
wherein the fluorescent boronic acid and the reference fluorophore are covalently coupled to the polymer matrix after polymerization; and
further 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 covalently coupled fluorescent boronic acid increases in the presence of bound glucose.
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Abstract
Improved polymer matrices which incorporate fluorescent biosensor molecules as well as methods of making and using these polymer matrices are described. Such matrices can be used in fluorescent biosensors and biosensor systems, including those which are used in the detection of polyhydroxylated analytes such as glucose. The properties of the polymer matrices of the invention renders biosensors utilizing such matrices particularly well-suited for detecting and measuring in-vivo glucose concentrations.
344 Citations
26 Claims
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1. A polymer composition comprising a fluorescent boronic acid of the general formula:
-
wherein;
F is a fluorophore;
N is a nitrogen atom;
B is a boron atom;
R1 is selected from 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, wherein the polymerized matrix is a polystyrene or a polyvinylalcohol;
L1 and L2 ate 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 futher includes a reference fluorophore; and
wherein the fluorescent boronic acid and the reference fluorophore are covalently coupled to the polymer matrix after polymerization; and
further 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 covalently coupled fluorescent boronic acid increases in the presence of bound glucose. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13)
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14. 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;
wherein;
F is a fluorophore;
N is a nitrogen atom;
B is a boron atom;
R1 is selected from 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, wherein the polymerized matrix is a polystyrene or a polyvinylalcohol;
L1 and L2 ate 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 covalendy coupled reference fluorophore and the covalently coupled fluorescent boronic acid increases in the presence of bound glucose. - View Dependent Claims (15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26)
- 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;
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Current AssigneeMedtronic Minimed Incorporated (Medtronic Plc)
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Original AssigneeMedtronic Minimed Incorporated (Medtronic Plc)
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InventorsHeiss, Aaron M., Cochran, Brooks, Walsh, Joseph C., Noronha, Glenn, Ponder, Bill C., Vachon, David J., Reilly, Jonathan
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Primary Examiner(s)Cheung, William K.
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Application NumberUS10/075,415Publication NumberTime in Patent Office1,272 DaysField of Search524/184, 525/259, 436/95US Class Current524/184CPC Class CodesC07F 5/025 Boronic and borinic acid co...G01N 33/66 involving blood sugars, e.g...Y10T 436/144444 Glucose
