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US 9,745,336 B2Granted
Fluorescent dye compounds, conjugates and uses thereof
AssigneeApplied Biosystems, LLC
InventorsRonald Graham, Ruiming Zou, Krishna Upadhya, Scott Benson
Life of this patent
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Abstract
The present teachings generally relate to fluorescent dyes, linkable forms of fluorescent dyes, energy transfer dyes, reagents labeled with fluorescent dyes and uses thereof.
Claims18
A composition comprising:
- a) an oligonucleotide comprising a fluorescent dye;
- and
- b) an internal standard dye compound;
- wherein the fluorescent dye of the oligonucleotide and the internal standard dye compound are spectrally resolvable and further wherein the internal standard dye compound is selected from:
- wherein
- R1-R3 and R6-R16 are each independently selected from —H, halogen, aryl, substituted aryl, heteroaryl, —CO2H, —CO2R, —SO3H, —SO3R, —CH2CO2H, —CH2CO2R, —CH2SO3H, —CH2SO3R, —CH2NH2, —CH2NHR, —NO2, C1-C6 alkyl, substituted C1-C6 alkyl, C1-C6 alkoxy, substituted C1-C6 alkoxy, C1-C6 alkoxyaryl, substituted C1-C6 alkoxyaryl, biphenyl, substituted biphenyl, benzyl, substituted benzyl, benzoyl, and substituted benzoyl, wherein R is selected from C1-C6 alkyl, substituted C1-C6 alkyl, C1-C6 alkoxy, substituted C1-C6 alkoxy, C1-C6 alkoxyaryl, substituted C1-C6 alkoxyaryl, phenyl, substituted phenyl, biphenyl, substituted biphenyl, benzyl, substituted benzyl, benzoyl, and substituted benzoyl;
- and
- R4 and R5 taken separately are selected from C1-C6 alkyl and C1-C6 substituted alkyl, R4 and R5 taken together are selected from C3-C7 cycloalkyl, C4-C7 unsaturated cycloalkyl, C3-C7 substituted cycloalkyl and C4-C7 substituted unsaturated cycloalkyl;
- with the proviso that if the internal standard dye compound is selected from compounds of formula (I), then at least one of R1, R2, R3 or R8 is not —H.
6 more elements
A kit comprising:
- a) an oligonucleotide labeled with a fluorescent dye;
- and
- b) an internal standard dye compound;
- wherein the fluorescent dye of the oligonucleotide and the internal standard dye compound are spectrally resolvable and further wherein the internal standard dye compound is selected from:
- wherein
- R1-R3 and R6-R16 are each independently selected from —H, halogen, aryl, substituted aryl, heteroaryl, —CO2H, —CO2R, —SO3H, —SO3R, —CH2CO2H, —CH2CO2R, —CH2SO3H, —CH2SO3R, —CH2NH2, —CH2NHR, —NO2, C1-C6 alkyl, substituted C1-C6 alkyl, C1-C6 alkoxy, substituted C1-C6 alkoxy, C1-C6 alkoxyaryl, substituted C1-C6 alkoxyaryl, biphenyl, substituted biphenyl, benzyl, substituted benzyl, benzoyl, and substituted benzoyl, wherein R is selected from C1-C6 alkyl, substituted C1-C6 alkyl, C1-C6 alkoxy, substituted C1-C6 alkoxy, C1-C6 alkoxyaryl, substituted C1-C6 alkoxyaryl, phenyl, substituted phenyl, biphenyl, substituted biphenyl, benzyl, substituted benzyl, benzoyl, and substituted benzoyl;
- and
- R4 and R5 taken separately are selected from C1-C6 alkyl and C1-C6 substituted alkyl, R4 and R5 taken together are selected from C3-C7 cycloalkyl, C4-C7 unsaturated cycloalkyl, C3-C7 substituted cycloalkyl and C4-C7 substituted unsaturated cycloalkyl;
- with the proviso that if the internal standard dye compound is selected from compounds of formula (I), then at least one of R1, R2, R3 or R8 is not —H.
6 more elements
A composition comprising:
- a) an oligonucleotide comprising a fluorescent dye;
- and
- b) an internal standard dye compound;
- wherein the fluorescent dye of the oligonucleotide and the internal standard dye compound are spectrally resolvable and further wherein the internal standard dye compound is:
- wherein
- R1-R3 and R6-R8 are each independently selected from —H, halogen, aryl, substituted aryl, heteroaryl, —CO2H, —CO2R, —SO3H, —SO3R, —CH2CO2H, —CH2CO2R, —CH2SO3H, —CH2SO3R, —CH2NH2, —CH2NHR, —NO2, C1-C6 alkyl, substituted C1-C6 alkyl, C1-C6 alkoxy, substituted C1-C6 alkoxy, C1-C6 alkoxyaryl, substituted C1-C6 alkoxyaryl, biphenyl, substituted biphenyl, benzyl, substituted benzyl, benzoyl, and substituted benzoyl, wherein R is selected from C1-C6 alkyl, substituted C1-C6 alkyl, C1-C6 alkoxy, substituted C1-C6 alkoxy, C1-C6 alkoxyaryl, substituted C1-C6 alkoxyaryl, phenyl, substituted phenyl, biphenyl, substituted biphenyl, benzyl, substituted benzyl, benzoyl, and substituted benzoyl;
- and
- R4 and R5 taken separately are selected from C1-C6 alkyl and C1-C6 substituted alkyl, R4 and R5 taken together are selected from C3-C7 cycloalkyl, C4-C7 unsaturated cycloalkyl, C3-C7 substituted cycloalkyl and C4-C7 substituted unsaturated cycloalkyl;
- with the proviso that at least one of R1, R2, R3 or R8 is not —H.
6 more elements
A kit comprising:
- a) an oligonucleotide labeled with a fluorescent dye;
- and
- b) an internal standard dye compound;
- wherein the fluorescent dye of the oligonucleotide and the internal standard dye compound are spectrally resolvable and further wherein the internal standard dye compound is:
- wherein
- R1-R3 and R6-R8 are each independently selected from —H, halogen, aryl, substituted aryl, heteroaryl, —CO2H, —CO2R, —SO3H, —SO3R, —CH2CO2H, —CH2CO2R, —CH2SO3H, —CH2SO3R, —CH2NH2, —CH2NHR, —NO2, C1-C6 alkyl, substituted C1-C6 alkyl, C1-C6 alkoxy, substituted C1-C6 alkoxy, C1-C6 alkoxyaryl, substituted C1-C6 alkoxyaryl, biphenyl, substituted biphenyl, benzyl, substituted benzyl, benzoyl, and substituted benzoyl, wherein R is selected from C1-C6 alkyl, substituted C1-C6 alkyl, C1-C6 alkoxy, substituted C1-C6 alkoxy, C1-C6 alkoxyaryl, substituted C1-C6 alkoxyaryl, phenyl, substituted phenyl, biphenyl, substituted biphenyl, benzyl, substituted benzyl, benzoyl, and substituted benzoyl;
- and
- R4 and R5 taken separately are selected from C1-C6 alkyl and C1-C6 substituted alkyl, R4 and R5 taken together are selected from C3-C7 cycloalkyl, C4-C7 unsaturated cycloalkyl, C3-C7 substituted cycloalkyl and C4-C7 substituted unsaturated cycloalkyl;
- with the proviso that at least one of R1, R2, R3 or R8 is not —H.
6 more elements
Dependencies are inferred from the claim text.