Analyte detection system
First Claim
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1. A use of a fluorescent label in a particle comprising incorporating one or more fluorescent label into a particle, at least one fluorescent label being a compound of the formula:
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wherein;
A and B each independently represent ring structures with sufficient carbon atoms to make up a cyanine nuclei;
X and Y are each independently selected from the group consisting of O, S, NR9, and CR9R10;
R1 and R2 are each independently selected from the group consisting of H, C1-C20 alkyl, C1-C20 haloalkyl, C1-C20 alkylene, and C1-C20 haloalkylene;
R3 is selected from the group consisting of H, halogen, OH, OR11, SR11, NR11R12, C1-C6 alkyl, C1-C6 alkylene, C3-C6 cycloalkyl, C3-C6 cycloheteroalkyl, C3-C6 cycloalkylene, C3-C6 cycloheteroalkylene, phenyl, biaryl, heteroaryl, and heterobiaryl, wherein the C1-C6 alkyl, C1-C6 alkylene, C3-C6 cycloalkyl, C3-C6 cycloheteroalkyl, C3-C6 cycloalkylene, C3-C6 cycloheteroalkylene, phenyl, biaryl, heteroaryl and heterobiaryl groups are unsubstituted or substituted with halogen, OH, C1-C4 alkyl, or C1-C4 haloalkyl;
R8 is selected from the group consisting of C1-C4 alkyl, and C1-C4 haloalkyl;
R9 and R10 are each independently selected from the group consisting of hydrogen, C1-C4 alkyl, and C1-C4 haloalkyl; and
R11 and R12 are each independently selected from the group consisting of C1-C6 alkyl, C3-C6 cycloalkyl, phenyl, biaryl, heteroaryl, or heterobiaryl, wherein the C1-C6 alky1, C1-C6 cycloalkyl, phenyl, biaryl, hereroaryl, and heterobiaryl groups are unsubstituted or substituted with halogen, OH, C1-C4 alkyl, or C1-C4 haloalkyl, or when R3 represents NR11R12, R11 and R12 may be taken together to form an optionally substituted C3-C6 aliphatic or C3-C6 aromatic heterocyclic ring.
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Abstract
An analyte detection system utilizing a combination of fluorescent labels for labeling particles and an analyte specific fluorescent analyte detection dye. The particles contain a combination of fluorescent labels for coding the particles and an analyte specific fluorescent dye. The particles can be used to identify and quantify analytes in an analytical sample by reaction of the analytical sample with the particles. An analytical device can identify the particles according to the combination of fluorescent labels. The device can then correlate the identified particle with the analyte specific fluorescent analyte detection dye. Multiple subpopulations of particles can be used to identify and quantify multi-analytes in a single analytical sample. Near infrared (NIR) fluorescent labels useful in the detection system are also provided.
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Citations
24 Claims
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1. A use of a fluorescent label in a particle comprising incorporating one or more fluorescent label into a particle, at least one fluorescent label being a compound of the formula:
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wherein; A and B each independently represent ring structures with sufficient carbon atoms to make up a cyanine nuclei;
X and Y are each independently selected from the group consisting of O, S, NR9, and CR9R10;
R1 and R2 are each independently selected from the group consisting of H, C1-C20 alkyl, C1-C20 haloalkyl, C1-C20 alkylene, and C1-C20 haloalkylene;
R3 is selected from the group consisting of H, halogen, OH, OR11, SR11, NR11R12, C1-C6 alkyl, C1-C6 alkylene, C3-C6 cycloalkyl, C3-C6 cycloheteroalkyl, C3-C6 cycloalkylene, C3-C6 cycloheteroalkylene, phenyl, biaryl, heteroaryl, and heterobiaryl, wherein the C1-C6 alkyl, C1-C6 alkylene, C3-C6 cycloalkyl, C3-C6 cycloheteroalkyl, C3-C6 cycloalkylene, C3-C6 cycloheteroalkylene, phenyl, biaryl, heteroaryl and heterobiaryl groups are unsubstituted or substituted with halogen, OH, C1-C4 alkyl, or C1-C4 haloalkyl;
R8 is selected from the group consisting of C1-C4 alkyl, and C1-C4 haloalkyl;
R9 and R10 are each independently selected from the group consisting of hydrogen, C1-C4 alkyl, and C1-C4 haloalkyl; and
R11 and R12 are each independently selected from the group consisting of C1-C6 alkyl, C3-C6 cycloalkyl, phenyl, biaryl, heteroaryl, or heterobiaryl, wherein the C1-C6 alky1, C1-C6 cycloalkyl, phenyl, biaryl, hereroaryl, and heterobiaryl groups are unsubstituted or substituted with halogen, OH, C1-C4 alkyl, or C1-C4 haloalkyl, or when R3 represents NR11R12, R11 and R12 may be taken together to form an optionally substituted C3-C6 aliphatic or C3-C6 aromatic heterocyclic ring. - View Dependent Claims (2, 3, 4, 5, 6, 7)
wherein; R4, R5, R6, and R7 are each independently selected from the group consisting of hydrogen, halogen, OH, C1-C4 alkyl, or C1-C4 haloalkyl, phenyl, and heteroaryl.
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3. The use of a fluoresecut label according to claim 2 wherein R1 and R2 are identical.
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4. The use of a fluorescent label according to claim 3, wherein at least one fluorescent label is a compound of the formula:
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wherein; R1 and R2 are each independently a C1-C20 alkyl; and
R3 is H, halogen, or —
S—
phenyl.
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5. The use of a fluorescent label according to claim 1 wherein the ring structures represented by A and B are each independently a benzoindole ring.
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6. The use of a fluorescent label according to claim 1 wherein each fluorescent label has a near-infrared excitation wavelength.
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7. The use of a fluorescent label according to claim 1 wherein each fluorescent label has an emitting light greater than 750 nm.
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8. A method for incorporating a fluorescent label into a particle comprising:
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a) preparing a suspension of particles; and
b) adding a solution of two or more fluorescent labels to the suspension, thereby incorporating the fluorescent labels into the particles, where at least one fluorescent label is a compound of the formula;
wherein; A and B each independently represent ring structures with sufficient carbon atoms to make up a cyanine nuclei;
X and Y are each independently selected from the group consisting of O, S, NR9, and CR9R10;
R1 and R2 are each independently selected from the group consisting of H, C1-C20 alkyl, C1-C20 haloalkyl, C1-C20 alkylene, and C1-C20 haloalkylene;
R3 is selected from the group consisting of H, halogen, OH, OR11, SR11, NR11R12, C1-C6 alkyl, C1-C6 alkylene, C3-C6 cycloalkyl, C3-C6 cycloheteroalkyl, C3-C6 cycloalkylene, C3-C6 cycloheteroalkylene, phenyl, biaryl, heteroaryl, and heterobiaryl, wherein the C1-C6 alkyl, C1-C6 alkylene, C3-C6 cycloalkyl, C3-C6 cycloheteroalkyl, C3-C6 cycloalkylene, C3-C6 cycloheteroalkylene, phenyl, biaryl, heteroaryl and heterobiaryl groups are unsubstituted or substituted with halogen, OH, C1-C4 alkyl, or C1-C4 haloalkyl;
R8 is selected from the group consisting of C1-C4 alkyl, and C1-C4 haloalkyl;
R9 and R10 are each independently selected from the group consisting of hydrogen, C1-C4 alkyl, and C1-C4 haloalkyl; and
R11 and R12 are each independently selected from the group consisting of C1-C6 alkyl, C3-C6 cycloalkyl, phenyl, biaryl, heteroaryl, or heterobiaryl, wherein the C1-C6 alky1, C1-C6 cycloalkyl, phenyl, biaryl, hereroaryl, and heterobiaryl groups are unsubstituted or substituted with halogen, OH, C1-C4 alkyl, or C1-C4 haloalkyl, or when R3 represents NR11R12, R11 and R12 may be taken together to form an optionally substituted C3-C6 aliphatic or C3-C6 aromatic heterocyclic ring. - View Dependent Claims (9, 10, 11, 12, 13, 14, 15)
wherein; R1 and R2 are each independently a C1-C20 alkyl; and
R3 is H, halogen, or —
S—
phenyl.
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13. A method according to claim 8 wherein in at least one of the fluorescent labels, the ring structures represented by A and B are each independently a benzoindole ring.
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14. A method according to claim 8 wherein at least one of the fluorescent labels has a near-infrared excitation wavelength.
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15. A method according to claim 8 wherein at least one of the fluorescent labels has an emitting light greater than 750 nm.
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16. A particle comprising a fluorescent label of the formula:
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wherein; A and B each independently represent ring structures with sufficient carbon atoms to make up a cyanine nuclei;
X and Y are each independently selected from the group consisting of O, S, NR9, and CR9R10;
R1 and R2 are each independently selected from the group consisting of H, C1-C20 alkyl, C1-C20 haloalkyl, C1-C20 alkylene, and C1-C20 haloalkylene;
R3 is selected from the group consisting of H, halogen, OH, OR11, SR11, NR11R12C1-C6 alkyl, C1-C6 alkylene, C3-C6 cycloalkyl, C3-C6 cycloheteroalkyl, C3-C6 cycloalkylene, C3-C6 cycloheteroalkylene, phenyl, biaryl, heteroaxyl, and heterobiaryl, wherein the C1-C6 alkyl, C1-C6 alkylene, C3-C6 cycloalkyl, C3-C6 cycloheteroalkyl, C3-C6 cycloalkylene, C3-C6 cycloheteroalkylene, phenyl, biaryl, heteroaryl and heterobiaryl groups are unsubstituted or substituted with halogen, OH, C1-C4 alkyl, or C1-C4 haloalkyl;
R6 is selected from the group consisting of C1-C4 alkyl, and C1-C4 haloalkyl;
R9 and R10 are each independently selected from the group consisting of hydrogen, C1-C4 alkyl, and C1-C4 haloalkyl; and
R11 and R12 are each independently selected from the group consisting of C1-C6 alkyl, C3-C6 cycloalkyl, phenyl, biaryl, heteroaryl, or heterobiaryl, wherein the C1-C6 alky1, C1-C6 cycloalkyl, phenyl, biaryl, heteroaryl, and heterobiaryl groups are unsubstituted or substituted with halogen, OH, C1-C4 alkyl, or C1-C4 haloalkyl, or when R3 represents NR11R12, R11 and R12 may be taken together to form an optionally substituted C3-C6 aliphatic or C3-C6 aromatic heterocyclic ring. - View Dependent Claims (17, 18, 19, 20, 21, 22)
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23. A particle prepared by a process comprising:
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a) preparing a particle suspension; and
b) adding a solution of two or more fluorescent labels to the suspension, thereby incorporating the fluorescent labels into the particle, where at least one fluorescent label is a compound of the formula;
wherein; A and B each independently represent ring structures with sufficient carbon atoms to make up a cyanine nuclei;
X and Y are each independently selected from the group consisting of O, S, NR9, and CR9R10;
R1 and R2 are each independently selected from the group consisting of H, C1-C20 alkyl, C1-C20 haloalkyl, C1-C20 alkylene, and C1-C20 haloalkylene;
R3 is selected from the group consisting of H, halogen, OH, OR11, SR11, NR11R12, C1-C6 alkyl, C1-C6 alkylene, C3-C6 cycloalkyl, C3-C6 cycloheteroalkyl, C3-C6 cycloalkylene, C3-C6 cycloheteroalkylene, phenyl, biaryl, heteroaryl, and heterobiaryl, wherein the C1-C6 alkyl, C1-C6 alkylene, C3-C6 cycloalkyl, C3-C6 cycloheteroalkyl, C3-C6 cycloalkylene, C3-C6 cycloheteroalkylene, phenyl, biaryl, heteroaryl and heterobiaryl groups are unsubstituted or substituted with halogen, OH, C1-C4 alkyl, or C1-C4 haloalkyl;
R8 is selected from the group consisting of C1-C4 alkyl, and C1-C4 haloalkyl;
R9 and R10 are each independently selected from the group consisting of hydrogen, C1-C4 alkyl, and C1-C4 haloalkyl; and
R11 and R12 are each independently selected from the group consisting of C1-C6 alkyl, C3-C6 cycloalkyl, phenyl, biaryl, heteroaryl, or heterobiaryl, wherein the C1-C6 alky1, C1-C6 cycloalkyl, phenyl, biaryl, heteroaryl, and heterobiaryl groups are unsubstituted or substituted with halogen, OH, C1-C4 alkyl, or C1-C4 haloalkyl, or when R3 represents NR11R12, R11 and R12 may be taken together to form an optionally substituted C3-C6 aliphatic or C3-C6 aromatic heterocyclic ring. - View Dependent Claims (24)
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Specification
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Current AssigneeBeckman Coulter Incorporated (Danaher Corporation)
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Original AssigneeBeckman Coulter Incorporated (Danaher Corporation)
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InventorsLin, Yuan, Michael, Josephine M., Pentoney, Stephen L. Jr., Bell, Michael L., Tsay, Tsong-Tseh
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Primary Examiner(s)Snay, Jeffrey R.
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Application NumberUS10/779,357Publication NumberTime in Patent Office635 DaysField of Search536/26.1, 536/18.7, 536/22.1, 436/172, 436/523, 436/546, 422/82.07, 422/82.08, 250/458.1, 250/459.1US Class Current436/172CPC Class CodesG01N 15/1459 the analysis being performe...G01N 2015/1438 Using two lasers in successionG01N 33/542 with steric inhibition or s...G01N 33/582 with fluorescent labelG01N 33/587 NanoparticlesY10T 436/13 Tracers or tags
