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US 8,540,521 B2Granted
Benzoxazole-based fluorescent metal ion indicators
AssigneeLife Technologies Corporation
InventorsKyle Gee, Vladimir Martin
Life of this patent
Estimating the term…
Abstract
Disclosed are benzoxazole-based compounds, kits, and methods of producing and using the described compounds in fluorescence-based detection of analytes (e.g., metal ions). Also disclosed are uses of benzoxazole-based compounds as ratiometric metal ion indicators.
Claims28
A compound of the formula:
- or a salt thereof,
- wherein M is —NCH2-Py or —N(CH2COOR5)2, wherein R5 is H, an alkyl having 1-6 carbons, —CH2OCOCH3, or a counterion;
- Y is —CH3, —CH2COOH, —CH2COOPy, or
- X is —N(CH2COOR5)2, —NCH2Py, —OCH2Py, or —OCH2COOR5;
- R7, R8, R9, and R10 are independently selected from the group consisting of an alkyl having 1-6 carbons, halogen, amino, nitro, cyano, trifluoromethyl, sulfo, and sulfonamide;
- R1 and R2 are independently H, an alkyl having 1-6 carbons, halogen, or sulfo;
- R4 is a 5 or 6-membered aromatic ring or a fused ring system comprising at least one 6-membered aromatic ring;
- L is an alkylene having 2-6 carbons;
- and
- p is 0 or 1.
7 more elements
A compound of the formula:
- or a salt thereof,
- wherein M is —NR3—, wherein R3 is —CH2-Py, —CH2Py, —CH2CH2OR5, or —CH2COOR5, wherein R5 is H, an alkyl having 1-6 carbons, —CH2OCOCH3, or a counterion;
- Z is
- wherein n is 1, 2, or 3;
- R6 is —CH2COOR6, —CH2CH2OR5, —CH2Py, or, when taken in combination with M, forms a structure
- wherein m is 1, 2, or 3;
- R7, R8, R9, and R10 are independently selected from the group consisting of an alkyl having 1-6 carbons, halogen, amino, nitro, cyano, trifluoromethyl, sulfo, and sulfonamide;
- R1 and R2 are independently H, an alkyl having 1-6 carbons, halogen, or sulfo;
- R4 is a 5 or 6-membered aromatic ring or a fused ring system comprising at least one 6-membered aromatic ring;
- L is an alkylene having 2-6 carbons;
- and
- p is 0 or 1.
9 more elements
A compound of the formula
- or a salt thereof,
- wherein M is —NCH2-Py, —N(CH2COOR5)2, wherein R5 is H, an alkyl having 1-6 carbons, —CH2OCOCH3, or a counterion;
- X is —N(CH2COOR5)2, —NCH2Py, —OCH2Py, or —OCH2COOR5;
- R7, R8, R9, and R10 are independently selected from the group consisting of an alkyl having 1-6 carbons, halogen, amino, nitro, cyano, trifluoromethyl, sulfo, and sulfonamide;
- R1 and R2 are independently H, an alkyl having 1-6 carbons, halogen, or sulfo;
- R4 is a 5 or 6-membered aromatic ring or a fused ring system comprising at least one 6-membered aromatic ring;
- L is an alkylene having 2-6 carbons;
- and
- p is 0 or 1.
6 more elements
Dependencies are inferred from the claim text.