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US 11,292,798 B2Granted
Merocyanine-based compound and biomolecular labeling dye, kit and contrast agent composition comprising same
AssigneeSfc Co., Ltd.
InventorsBong-Ki Shin, Jong-Tae Je
Life of this patent
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Abstract
The present invention relates to: a novel merocyanine-based compound which exhibits a fluorescence signal at a visible light region of at least 380 nm, and which may be used for detecting biomolecules; and a biomolecular labeling dye, kit and contrast agent composition comprising the same.
Claims8
A merocyanine-based compound represented by the following Chemical Formula 1:
- wherein,
- Ar1 is a substituted or unsubstituted aryl or a substituted or unsubstituted heteroaryl,
- Y1 and Y2 are each independently selected from sulfur, oxygen, selenium, NR3, CR3R4, SiR3R4, and —CR3═CR4—,
- Q is sulfur, oxygen, or NRa,
- R1 is each independently selected from hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl, a substituted or unsubstituted C2-C10 alkenyl, a substituted or unsubstituted C1-C10 haloalkyl, a halogen, cyano, a substituted or unsubstituted amino, a substituted or unsubstituted amide, carboxyl, carboxylates, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, ketones (—COR5), aldehydes, esters (—COOR5), a -L-X functional group, and a -L-Z functional group,
- Ra and R2 to R4 are each independently selected from hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl, a substituted or unsubstituted C2-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 C2-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 (—COR5), aldehydes, esters (—COOR5), acyl chloride, sulfonic acid, sulfonates, a -L-X functional group, and a -L-Z functional group,
- when R1, R2, R3, or R4 is a ketone group (—COR5) or an ester group (—COOR5), R5 is selected from a substituted or unsubstituted C1-C10 alkyl, a substituted or unsubstituted C2-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 C2-C10 alkoxy, a substituted or unsubstituted C1-C10 haloalkyl, a substituted or unsubstituted heteroaryl, and a substituted or unsubstituted C1-C10 aminoalkyl,
- R9 and R10 are each independently selected from hydrogen and a substituted or unsubstituted alkyl, or R9 and R10 are bonded to each other to form a four-membered, five-membered, or a six-membered hydrocarbon ring,
- in the -L-X and -L-Z functional groups,
- L is a linker selected from 1-20 atoms selected from carbon, nitrogen, oxygen, and sulfur, —NHCOO—, —CONH—, —CH2NH—, —CH2NR6—, —COO—, —SO2NH—, —HN—C(═NH)—NH—, —NR6—, —(CH2—CH2—O—)p—, —CH═CH—, —C≡C—, —Ar—, and —CO—Ar—NR6—, R6 is selected from hydrogen, a substituted or unsubstituted C1-C6 alkyl, a substituted or unsubstituted C2-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 C2-C6 alkoxy, and a substituted or unsubstituted C1-C6 haloalkyl, Ar is an aryl or a heteroaryl, and p is an integer from 1 to 100,
- 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,
- when R1, R2, R3, R4, R5, or R6 is substituted, any carbon or terminal carbon in the functional group is substituted with at least one selected from sulfonic acid, sulfonates, carboxylic acids, carboxylates, phosphoric acid, phosphates, alkyls, heteroaryls, polyalkylene oxides, quaternary ammonium salts, esters, and amides, and
- m is an integer from 1 to 3.
11 more elements
Dependencies are inferred from the claim text.