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US 11,597,842 B2Granted
Labeling dye and kit including same
AssigneeSfc Co., Ltd.
InventorsBong-Ki Shin, Tae-Young Kim, Ju-Man Song, Hee-Jung Yang, Jong-Tae Je
Life of this patent
Estimating the term…
Abstract
The present invention relates to: a labeling dye having excellent fluorescent intensity and photostability; and a kit.
Claims17
A labeling dye represented by the following [Chemical Formula 1] or [Chemical Formula 2]:
- in [Chemical Formula 1] or [Chemical Formula 2],
- X is CR6R7, S, or O,
- Q is a polymethine in which a ring selectively including at least one heteroatom selected from nitrogen, oxygen, and sulfur is substituted, or a polyene in which a ring selectively including at least one heteroatom selected from nitrogen, oxygen, and sulfur is substituted,
- R1 is selected from the following [Chemical Formula 3] to [Chemical Formula 5], or -L-X functional group,
- R2 to R7 are each independently selected from hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl, a substituted or unsubstituted C1-C10 heteroalkyl including at least one heteroatom, a substituted or unsubstituted C2-C10 alkenyl, a substituted or unsubstituted C2-C10 alkynyl, a substituted or unsubstituted C1-C10 alkoxy, a substituted or unsubstituted aryloxy, a substituted or unsubstituted C1-C10 haloalkyl, a halogen, cyano, hydroxyl, a substituted or unsubstituted amino, a substituted or unsubstituted amide, carbamates, sulfhydryl, nitro, carboxyl, carboxylates, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted aralkyl, quaternary ammonium, phosphoric acid, phosphates, ketones (—CO), aldehydes, esters (—COO), acyl chloride, sulfonic acid, sulfonates, hydrazine, thiols, acetals, ketals, phosphonates (phosphites), hypophosphite, sulfohydroxyl, sulfates, azido, guanidium, carbonyl, thiocarbonyl, aminothiocarbonyl, polyalkylene oxides, a -L-X functional group, a -L-Z functional group, and the following [Chemical Formula 3] to [Chemical Formula 5], or two or more selected from R1 to R7 are linked to each other to form a fused ring,
- L is a linker including 1 to 150 non-hydrogen atoms,
- X is a reactive group selected from carboxyl, succinimidyl ester, sulfo-succinimidyl ester, isothiocyanate, maleimide, haloacetamide, hydrazide, vinyl sulphone, dichlorotriazine, phosphoramidite, alkyl halides, acyl halides, carbohydrazide, hydroxylamine, ketones, alkynes, azide, aliphatic and aromatic amines, sulfotetrafluorophenyl ester, sulfodichlorophenyl ester, carbonyl azide, sulfonyl chloride, sulfonyl fluoride, boronic acid, isocyanate, a halogen-substituted triazine, a halogen-substituted pyridine, a halogen-substituted diazine, tetrafluorophenyl ester, imido ester, azidonitrophenyl, glyoxal, and aldehydes,
- Z is a fluorophore capable of generating a fluorescence signal,
- at least one or more of R1 to R7 are one selected from the following [Chemical Formula 3] to [Chemical Formula 5],
- in [Chemical Formula 3] to [Chemical Formula 5],
- L1 is a linker including 1 to 150 non-hydrogen atoms,
- L1 in [Chemical Formula 3] to [Chemical Formula 5] is present or not present,
- L2 is a C1-C20 alkylene, or a C1-C20 heteroalkylene including at least one heteroatom,
- A is hydrogen or M+ (M+ is a counter ion),
- R is selected from hydrogen, a substituted or unsubstituted C1-C10 alkyl, a substituted or unsubstituted C1-C10 heteroalkyl including at least one heteroatom, a substituted or unsubstituted C2-C10 alkenyl, a substituted or unsubstituted C2-C10 alkynyl, a substituted or unsubstituted C1-C10 alkoxy, and a substituted or unsubstituted C1-C10 haloalkyl,
- R′ represents a site bonded to at least one of R1 to R7, and
- at least one or more of R and R1 to R7 are a -L-X functional group.
14 more elements
A labeling dye represented by the following [Chemical Formula 1] or [Chemical Formula 2]:
- in [Chemical Formula 1] or [Chemical Formula 2],
- X is CR6R7, S, or O,
- Q is a polymethine in which a ring selectively including at least one heteroatom selected from nitrogen, oxygen, and sulfur is substituted, or a polyene in which a ring selectively including at least one heteroatom selected from nitrogen, oxygen, and sulfur is substituted,
- wherein any carbon in the polymethine or the polyene is substituted with a -L-Z functional group,
- R1 to R7 are each independently selected from hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl, a substituted or unsubstituted C1-C10 heteroalkyl including at least one heteroatom, a substituted or unsubstituted C2-C10 alkenyl, a substituted or unsubstituted C2-C10 alkynyl, a substituted or unsubstituted C1-C10 alkoxy, a substituted or unsubstituted aryloxy, a substituted or unsubstituted C1-C10 haloalkyl, a halogen, cyano, hydroxyl, a substituted or unsubstituted amino, a substituted or unsubstituted amide, carbamates, sulfhydryl, nitro, carboxyl, carboxylates, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted aralkyl, quaternary ammonium, phosphoric acid, phosphates, ketones (—CO), aldehydes, esters (—COO), acyl chloride, sulfonic acid, sulfonates, hydrazine, thiols, acetals, ketals, phosphonates (phosphites), hypophosphite, sulfohydroxyl, sulfates, azido, guanidium, carbonyl, thiocarbonyl, aminothiocarbonyl, polyalkylene oxides, a -L-X functional group, a -L-Z functional group, and the following [Chemical Formula 3] to [Chemical Formula 5], or two or more selected from R1 to R7 are linked to each other to form a fused ring,
- L is a linker including 1 to 150 non-hydrogen atoms,
- X is a reactive group selected from carboxyl, succinimidyl ester, sulfo-succinimidyl ester, isothiocyanate, maleimide, haloacetamide, hydrazide, vinyl sulphone, dichlorotriazine, phosphoramidite, alkyl halides, acyl halides, carbohydrazide, hydroxylamine, ketones, alkynes, azide, aliphatic and aromatic amines, sulfotetrafluorophenyl ester, sulfodichlorophenyl ester, carbonyl azide, sulfonyl chloride, sulfonyl fluoride, boronic acid, isocyanate, a halogen-substituted triazine, a halogen-substituted pyridine, a halogen-substituted diazine, tetrafluorophenyl ester, imido ester, azidonitrophenyl, glyoxal, and aldehydes,
- Z is a fluorophore capable of generating a fluorescence signal, and is selected from structures displayed by coumarins, cyanine, BODIPY, fluoresceins, rhodamines, pyrenes, carbopyronin, oxazines, xanthenes, thioxanthene, acridines, or a fluorophore selected from a structure represented by [Chemical Formula 1] or [Chemical Formula 2],
- at least one or more of R1 to R7 are one selected from the following [Chemical Formula 3] to [Chemical Formula 5],
- in [Chemical Formula 3] to [Chemical Formula 5],
- L1 is a linker including 1 to 150 non-hydrogen atoms,
- L1 in [Chemical Formula 3] to [Chemical Formula 5] is present or not present,
- L2 is a C1-C20 alkylene, or a C1-C20 heteroalkylene including at least one heteroatom,
- A is hydrogen or M+ (M+ is a counter ion),
- R is selected from hydrogen, a substituted or unsubstituted C1-C10 alkyl, a substituted or unsubstituted C1-C10 heteroalkyl including at least one heteroatom, a substituted or unsubstituted C2-C10 alkenyl, a substituted or unsubstituted C2-C10 alkynyl, a substituted or unsubstituted C1-C10 alkoxy, and a substituted or unsubstituted C1-C10 haloalkyl,
- R′ represents a site bonded to at least one of R1 to R7, and
- at least one or more of R and R1 to R7 are a -L-X functional group.
14 more elements
Dependencies are inferred from the claim text.