SMMR (small molecule metabolite reporters) for use as in vivo glucose biosensors
First Claim
Patent Images
1. A small molecule metabolite reporter compound of the following formula:
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wherein D is a heteroatom;
R1 and R2 are different and are selected from the group consisting of H, OH, NH2, NO2, OCH3, N(CH3)2, A, or, R1 and R2, taken together with the ring to which they are attached, form R7;
R3 and R4 are different and are selected from the group consisting of H,
OH, B(OH)2, M, or R3 and R4, taken together with the ring to which they are attached, form R8;
R5 and R6 are different and are selected from the group consisting of H or
wherein Q is H, COOH, B(OH)2, or M;
A isR7 is
R8 is
M is
L, when present, is an amino-containing linking moiety;
R1 and R2, and R3 and R4, are adjacent to each other on the rings on which they reside; and
at least one boronic acid moiety is present; and
salts thereof.
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Abstract
Small Molecule Metabolite Reporters (SMMRs) for use as in vivo glucose biosensors, sensor compositions, and methods of use, are described. The SMMRs include boronic acid-containing xanthene, coumarin, carbostyril and phenalene-based small molecules which are used for monitoring glucose in vivo, advantageously on the skin.
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Citations
15 Claims
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1. A small molecule metabolite reporter compound of the following formula:
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wherein D is a heteroatom;
R1 and R2 are different and are selected from the group consisting of H, OH, NH2, NO2, OCH3, N(CH3)2, A, or, R1 and R2, taken together with the ring to which they are attached, form R7;
R3 and R4 are different and are selected from the group consisting of H,
OH, B(OH)2, M, or R3 and R4, taken together with the ring to which they are attached, form R8;
R5 and R6 are different and are selected from the group consisting of H or
wherein Q is H, COOH, B(OH)2, or M;
A is R7 is R8 is M is L, when present, is an amino-containing linking moiety;
R1 and R2, and R3 and R4, are adjacent to each other on the rings on which they reside; and
at least one boronic acid moiety is present; and
salts thereof.- View Dependent Claims (2, 7)
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3. A small molecule metabolite reporter compound of the following formula:
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wherein R1 and R2 are different and may be A, or, R1 and R2, taken together with the ring to which they are attached, form R7;
R3 and R4 are different and are selected from the group consisting of H,
OH, B(OH)2, M, or R3 and R4, taken together with the ring to which they are attached, form R8;
R6 is A is R7 is R8 is M is L, when present, is an amino-containing linking moiety; and
R1 and R2, and R3 and R4, are adjacent to each other on the rings on which they reside; and
salts thereof.
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4. A small molecule metabolite reporter compound of the following formula:
-
wherein R1 and R2 are different and are selected from the group consisting of H, OH, NH2, NO2, OCH3, N(CH3)2, A, or, R1 and R2, taken together with the ring to which they are attached, form R7;
R3 and R4 are different and are selected from the group consisting of H, OH, M, or R3 and R4, taken together with the ring to which they are attached, form R8;
R5 and R6 are different and are selected from the group consisting of H or
wherein Q is H or M;
A is R7 is R8 is M is L, when present, is an amino-containing linking moiety; and
R1 and R2, and R3 and R4, are adjacent to each other on the rings on which they reside; and
salts thereof.
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5. A small molecule metabolite reporter compound of the following formula:
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wherein M is L, when present, is an amino-containing linking moiety; and
salts thereof.
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6. A small molecule metabolite reporter compound of the following formula:
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wherein D is a heteroatom (e.g., O or N);
R9 is H, OH, CH3, CF3, M, or an amino or substituted amino group;
R10 is H, CH3, or M;
R11, R12, and R13 are individually H, OH, alkoxy, M, or an amino or substituted amino group;
R14, when present, is H or CH3;
M is at least one boronic acid moiety is present; and
salts thereof.
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8. A method of measuring a compound or metabolite thereof, comprising contacting a reporter compound of the following formula:
-
wherein D is a heteroatom;
R1 and R2 are different and are selected from the group consisting of H, OH, NH2, NO2, OCH3, N(CH3)2, A, or, R1 and R2, taken together with the ring to which they are attached, form R7;
R3 and R4 are different and are selected from the group consisting of H,
OH, B(OH)2, M, or R3 and R4, taken together with the ring to which they are attached, form R8;
R5 and R6 are different and are selected from the group consisting of H or
wherein Q is H, COOH, B(OH)2, or M;
A is R7 is R8 is M is L, when present, is an amino-containing linking moiety;
R1 and R2, and R3 and R4, are adjacent to each other on the rings on which they reside; and
at least one boronic acid moiety is present; and
salts thereof;
which reporter compound is sensitive to the presence of said compound or metabolite thereof, with an area of the body where said metabolites may be found, and detecting a photometric change in said reporter compound indicative of said metabolite.
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9. A method of measuring a compound or metabolite thereof, comprising contacting a reporter compound of the following formula:
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wherein R1 and R2 are different and may be A, or, R1 and R2, taken together with the ring to which they are attached, form R7;
R3 and R4 are different and are selected from the group consisting of H, OH, B(OH)2, M, or R3 and R4, taken together with the ring to which they are attached, form R8;
R6 is A is or R7 is R8 is M is L, when present, is an amino-containing linking moiety; and
R1 and R2, and R3 and R4, are adjacent to each other on the rings on which they reside; and
salts thereof;
which reporter compound is sensitive to the presence of said compound or metabolite thereof, with an area of the body where said metabolites may be found, and detecting a photometric change in said reporter compound indicative of said metabolite.
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10. A method of measuring a compound or metabolite thereof, comprising contacting a reporter compound of the following formula:
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wherein R1 and R2 are different and are selected from the group consisting of H, OH, NH2, NO2, OCH3, N(CH3)2, A, or, R1 and R2, taken together with the ring to which they are attached, form R7;
R3 and R4 are different and are selected from the group consisting of H,
OH, M, or R3 and R4, taken together with the ring to which they are attached, form R8;
R5 and R6 are different and are selected from the group consisting of H or
wherein Q is H or M;
A is R7 is R8 is M is L, when present, is an amino-containing linking moiety; and
R1 and R2, and R3 and R4, are adjacent to each other on the rings on which they reside; and
salts thereof;
which reporter compound is sensitive to the presence of said compound or metabolite thereof, with an area of the body where said metabolites may be found, and detecting a photometric change in said reporter compound indicative of said metabolite.- View Dependent Claims (11, 12, 13, 14, 15)
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Specification
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Current AssigneeCercacor Laboratories
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Original AssigneeCercacor Laboratories
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InventorsLambert, Christopher, Bu, Dongsheng, Wang, Zhaolin, Bellott, Emile, Childs, James, Workman, Jerome, Zelenchuk, Alex, Nienaber, Hubert, Shi, Shirley
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Granted Patent
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Time in Patent OfficeDays
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Field of Search
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US Class Current424/9.600
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CPC Class CodesA61K 49/0021 the fluorescent group being...A61K 49/0041 Xanthene dyes, used in vivo...A61K 49/0052 Small organic molecules oli...C07F 5/025 Boronic and borinic acid co...C07F 7/1804 Compounds having Si-O-C lin...Y10T 436/144444 Glucose
