ANALYTE SENSING VIA ACRIDINE-BASED BORONATE BIOSENSORS
First Claim
1. A biosensor molecule, The biosensor molecule comprising:
- an acridine-based fluorophore;
a boronate binding moiety that is capable of specifically and reversibly binding a polyhydroxylate analyte in a sample; and
a linker moiety that links the fluorophore to the boronate binding moiety, wherein the biosensor molecule is capable of emitting a light signal in the visible to near infrared region of the spectrum that can be correlated to a polyhydroxylate analyte concentration in a sample and further wherein the biosensor molecule comprises a molecule of the formula;
wherein F is an acridine-based fluorophore;
R1 is selected from the group consisting of hydrogen, and aromatic moieties;
R2 and R4 are optional moieties selected from the group consisting of hydrogen, aliphatic and aromatic moieties and groups that are capable of forming covalent bonds to a biocompatible matrix;
L1 and L2 are —
CH3—
;
Z is nitrogen;
R3 is an optional group selected from the group consisting of hydrogen, aliphatic and aromatic moieties and groups that are capable of forming covalent bonds to a biocomparible matrix; and
wherein F and Z are capable of being involved in an intramolecular photo-induced electron transfer process that quenches the fluorescence of F in the absence of bound polyhydroxylate analyte.
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Accused Products
Abstract
Fluorescent biosensor molecules, fluorescent biosensors and systems, as well as methods of making and using these biosensor molecules and systems are described. These biosensor molecules address the problem of obtaining fluorescence emission at wavelengths greater than about 500 nm. Biosensor molecules generally include an (1) an acridine-based fluorophore, (2) a linker moiety and (3) a boronate substrate recognition/binding moiety, which binds polyhydroxylate analytes, such as glucose. These biosensor molecules further include a “switch” element that is drawn from the electronic interactions among these submolecular components. This fluorescent switch is generally “off” in the absence of bound polyhydroxylate analyte and is generally “on” in the presence of bound polyhydroxylate analyte. Thus, the reversible binding of a polyhydroxylate analyte essentially turns the fluorescent switch “on” and “off”. This property of the biosensor molecules, as well as their ability to emit fluorescent light at greater than about 500 nm, renders these biosensor molecules particularly well-suited for detecting and measuring in-vivo glucose concentrations.
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Citations
54 Claims
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1. A biosensor molecule, The biosensor molecule comprising:
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an acridine-based fluorophore;
a boronate binding moiety that is capable of specifically and reversibly binding a polyhydroxylate analyte in a sample; and
a linker moiety that links the fluorophore to the boronate binding moiety, wherein the biosensor molecule is capable of emitting a light signal in the visible to near infrared region of the spectrum that can be correlated to a polyhydroxylate analyte concentration in a sample and further wherein the biosensor molecule comprises a molecule of the formula;
wherein F is an acridine-based fluorophore;
R1 is selected from the group consisting of hydrogen, and aromatic moieties;
R2 and R4 are optional moieties selected from the group consisting of hydrogen, aliphatic and aromatic moieties and groups that are capable of forming covalent bonds to a biocompatible matrix;
L1 and L2 are —
CH3—
;
Z is nitrogen;
R3 is an optional group selected from the group consisting of hydrogen, aliphatic and aromatic moieties and groups that are capable of forming covalent bonds to a biocomparible matrix; and
wherein F and Z are capable of being involved in an intramolecular photo-induced electron transfer process that quenches the fluorescence of F in the absence of bound polyhydroxylate analyte. - View Dependent Claims (2, 3, 5, 6, 7, 8, 9, 10, 11, 12, 21, 46, 47, 48, 49, 50, 51, 52, 53, 54)
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4. (canceled)
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13-20. -20. (canceled)
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22-45. -45. (canceled)
Specification