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US 9,315,864 B2Granted
Heteroarylcyanine dyes with sulfonic acid substituents
AssigneePacific Biosciences of California, Inc.
InventorsStephen Yue, Gene Shen, Wei-Chuan Sun
Life of this patent
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Abstract
Heteroaryl cyanine dyes bearing sulfonic acid substituents are of use in various assays, including single molecule nucleic acid sequencing. Exemplary heteroaryl cyanines dyes include or more reactive functional group, which is of use to covalently conjugate the cyanine dye to a carrier molecule. An exemplary carrier molecule is an analyte molecule or other molecule of interest, for example, a nucleotide oligophosphate.
Claims29
A fluorescent cyanine compound, or a covalent conjugate thereof, having a formula selected from:
- wherein
- R1, R2 and R3 are independently CH2R7;
- wherein
- R4, R5, R6, R6′, and R7 are members independently selected from H, R28, R28Z2, SO3H, CO2H, R28SO3H, C(O)NHR28SO3H, CONHR28C(O)Z2,
- wherein
- Z2 is selected from OH, O—, a reactive functional group, and a linker covalently bound to a carrier molecule;
- Rg1 and Rg2 are members independently selected from H, R38, R38Z3, SO3H, CO2H, R38SO3H, CONHR38SO3H, CONHR38C(O)Z2,
- wherein
- R28 and R38 are independently selected from a bond, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl and substituted or unsubstituted heterocycloalkyl;
- Z3 is selected from OH, O—, a reactive functional group, and a linker covalently bound to a carrier molecule;
- wherein
- R1′, R2′ and R3′ are independently CH2R7′;
- wherein
- R4′, R5′, and R7′ are members independently selected from H, R28′, R28′Z2′, SO3H, CO2H, R28′SO3H, CONHR28′SO3H, CONHR28′C(O)Z2′, and
- wherein
- Z2′ is selected from OH, O—, a reactive functional group, and a linker covalently bound to a carrier molecule;
- Rg1′ and Rg2′ are members independently selected from H, R38′, R38′Z3′, SO3H, CO2H, R38′SO3H, CONHR38′SO3H, CONHR38′C(O)Z3′,
- wherein
- R28′ and R38′ are independently selected from a bond, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl and substituted or unsubstituted heterocycloalkyl;
- and
- Z3′ is selected from OH, O—, a reactive functional group, and a linker covalently bound to a carrier molecule,
- at least one of Z2, Z2′, Z3, Z3′, R1, R1′, R2, R2′, R3, R3′, R4, R4′, R5, R5′, R6 and R6′ is a reactive functional group, or is a linker covalently bound to a carrier molecule;
- and
- said compound comprises at least three SO3H moieties.
21 more elements
A fluorescent cyanine compound, or a covalent conjugate thereof, having a formula selected from:
- wherein
- R1, R2 and R3 are independently CH2R7;
- wherein
- R4, R5, R6, R6′, and R7 are members independently selected from H, R28, R28Z2, SO3H, CO2H, R28SO3H, C(O)NHR28SO3H, CONHR28C(O)Z2,
- wherein
- Z2 is selected from OH, O—, COOH, an activated carboxyl moiety, and a linker covalently bound to a carrier molecule;
- Rg1 and Rg2 are members independently selected from H, R38, R38Z3, SO3H, CO2H, R38SO3H, CONHR38SO3H, CONHR38C(O)Z2,
- wherein
- R28 and R38 are independently selected from a bond, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl and substituted or unsubstituted heterocycloalkyl;
- Z3 is selected from OH, O—, COOH, an activated carboxyl moiety, and a linker covalently bound to a carrier molecule;
- in which wherein
- R1′, R2′ and R3′ are independently CH2R7′;
- wherein
- R4′, R5′, and R7′ are members independently selected from H, R28′, R28′Z2′, SO3H, CO2H, R28′SO3H, CONHR28′SO3H, CONHR28′C(O)Z2′, and
- wherein
- Z2′ is selected from OH, O—, COOH, an activated carboxyl moiety, and a linker covalently bound to a carrier molecule;
- Rg1′ and Rg2′ are members independently selected from H, R38′, R38′Z3′, SO3H, CO2H, R38′SO3H, CONHR38′SO3H, CONHR38′C(O)Z3′,
- wherein
- R28′ and R38′ are independently selected from a bond, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl and substituted or unsubstituted heterocycloalkyl;
- and
- Z3′ is selected from OH, O—, COOH, an activated carboxyl moiety, a reactive functional group, and a linker covalently bound to a carrier molecule,
- at least one of Z2, Z2′, Z3, Z3′, R1, R1′, R2, R2′, R3, R3′, R4, R4′, R5, R5′, R6 and R6′ is a linker covalently bound to a carrier molecule;
- and
- said compound comprises at least three SO3H moieties.
21 more elements
Dependencies are inferred from the claim text.