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US 10,647,723 B2Granted
Thiochromene type compound and use thereof
AssigneeSogang University Research Foundation
InventorsBong-Jin Moon, Han-Bin Oh, Na-Na Kang, Ae-Ran Jeon, Kye-Shin Park, Je-Hyun Baek
Life of this patent
Estimating the term…
Abstract
This invention relates to a photocleavable mass tag and the use thereof, and particularly to a thiochromene-type compound useful for MALDI-TOF (Matrix-Assisted Laser Desorption/Ionization Time-Of-Flight) mass spectrometry or matrix-less LDI-TOF (Laser Desorption/Ionization Time-Of-Flight) mass spectrometry and the use thereof.
Claims9
A compound represented by Formula I below:
- In Formula I, R1 is a C1-12 alkyl group, a C6-60 aryl group, or a C2-60 heteroaryl group containing at least one heteroatom selected from among N, S and O, having a reactive group at a terminal thereof, the reactive group being any one of a N-hydroxysuccinimide ester group, a N-hydroxysulfosuccinimide ester group, a pentafluorophenyl ester group, a 4-sulfo-2,3,5,6-tetrafluorophenyl ester group, a nitrophenyl ester group, a 2,4,5-trichlorophenyl ester group, a phthalimido ester group, a N-hydroxy-5-norbornen-endo-2,3-dicarboimide ester group, and a maleimide group,
- R2 and R3 are independently hydrogen, a C1-12 alkyl, a C6-60 aryl, a C1-12 alkoxy, a C1-12 alkylamino, a C1-12 alkylthio or a fused ring, the fused ring being any one selected from among pyrrole, thiophene, indole, furan, imidazole, triazole, diazole, and pyrimidine, and
- Ar is benzene or a heteroaromatic ring selected from among pyrrole, thiophene, indole, furan, imidazole, triazole, diazole, and pyrimidine.
A compound represented by Formula II below:
- in Formula II, R1 is a C1-12 alkyl group, a C6-60 aryl group, or a C2-60 heteroaryl group containing at least one heteroatom selected from among N, S and O, having a reactive group at a terminal thereof, the reactive group being any one of a N-hydroxysuccinimide ester group, a N-hydroxysulfosuccinimide ester group, a pentafluorophenyl ester group, a 4-sulfo-2,3,5,6-tetrafluorophenyl ester group, a nitrophenyl ester group, a 2,4,5-trichlorophenyl ester group, a phthalimido ester group, a N-hydroxy-5-norbornen-endo-2,3-dicarboimide ester group, and a maleimide group, and
- R2 and R3 are independently hydrogen, a C1-12 alkyl, a C6-60 aryl, a C1-12 alkoxy, a C1-12 alkylamino, a C1-12 alkylthio or a fused ring, the fused ring being any one selected from among pyrrole, thiophene, indole, furan, imidazole, triazole, diazole, and pyrimidine.
A compound represented by Formula III below:
- in Formula III, R2 and R3 are independently hydrogen, a C1-12 alkyl, a C6-60 aryl, a C1-12 alkoxy, a C1-12 alkylamino, a C1-12 alkylthio or a fused ring,
- C(═O)R4 is N-hydroxysuccinimidyl, N-hydroxy sulfosuccinimidyl, pentafluorophenyloxy, 4-sulfo-2,3,5,6-tetrafluorophenyloxy, nitrophenyloxy, 2,4,5-trichlorophenyloxy, phthalimidoyloxy, N-hydroxy-5-norbornen-endo-2,3-dicarboimidyloxy, or maleimide, and
- n is an integer of 1-12,
- the fused ring being any one selected from among pyrrole, thiophene, indole, furan, imidazole, triazole, diazole, and pyrimidine.
1 more element
A compound represented by Formula IV below:
- in Formula IV, R1 is a C1-12 alkyl group, a C6-60 aryl group, or a C2-60 heteroaryl group containing at least one heteroatom selected from among N, S and O, having a reactive group at a terminal thereof, the reactive group being any one of a N-hydroxysuccinimide ester group, a N-hydroxysulfosuccinimide ester group, a pentafluorophenyl ester group, a 4-sulfo-2,3,5,6-tetrafluorophenyl ester group, a nitrophenyl ester group, a 2,4,5-trichlorophenyl ester group, a phthalimido ester group, a N-hydroxy-5-norbornen-endo-2,3-dicarboimide ester group, and a maleimide group, and
- R2 and R3 are independently hydrogen, a C1-12 alkyl, a C6-60 aryl, a C1-12 alkoxy, a C1-12 alkylamino, a C1-12 alkylthio or a fused ring, the fused ring being any one selected from among pyrrole, thiophene, indole, furan, imidazole, triazole, diazole, and pyrimidine.
A compound represented by Formula V below:
- in Formula V, A is a C1-12 alkyl group, a C6-60 aryl group, or a C2-60 heteroaryl group containing at least one heteroatom selected from among N, S and O, having a reactive group at a terminal thereof, the reactive group being any one of a N-hydroxysuccinimide ester group, a N-hydroxysulfosuccinimide ester group, a pentafluorophenyl ester group, a 4-sulfo-2,3,5,6-tetrafluorophenyl ester group, a nitrophenyl ester group, a 2,4,5-trichlorophenyl ester group, a phthalimido ester group, a N-hydroxy-5-norbornen-endo-2,3-dicarboimide ester group, and a maleimide group,
- R2 and R3 are independently hydrogen, a C1-12 alkyl, a C6-60 aryl, a C1-12 alkoxy, a C1-12 alkylamino, a C1-12 alkylthio or a fused ring, the fused ring being any one selected from among pyrrole, thiophene, indole, furan, imidazole, triazole, diazole, and pyrimidine, and
- Ar is benzene or a heteroaromatic ring selected from among pyrrole, thiophene, indole, furan, imidazole, triazole, diazole, and pyrimidine.
A conjugate compound of a biomaterial and a compound represented by Formula Ia below:
- in Formula Ia, A is a C1-12 alkyl group, a C6-60 aryl group, or a C2-60 heteroaryl group containing at least one heteroatom selected from among N, S and O, having a reactive group at a terminal thereof, the reactive group being any one of a N-hydroxysuccinimide ester group, a N-hydroxysulfosuccinimide ester group, a pentafluorophenyl ester group, a 4-sulfo-2,3,5,6-tetrafluorophenyl ester group, a nitrophenyl ester group, a 2,4,5-trichlorophenyl ester group, a phthalimido ester group, a N-hydroxy-5-norbornen-endo-2,3-dicarboimide ester group, and a maleimide group,
- R2 and R3 are independently hydrogen, a C1-12 alkyl, a C6-60 aryl, a C1-12 alkoxy, a C1-12 alkylamino, a C1-12 alkylthio or a fused ring, the fused ring being any one selected from among pyrrole, thiophene, indole, furan, imidazole, triazole, diazole, and pyrimidine, and
- Ar is benzene or a heteroaromatic ring selected from among pyrrole, thiophene, indole, imidazole, triazole, and pyrimidine,
- wherein the biomaterial is an antigen, an antibody, a biomarker, a peptide, a nucleic acid, or a glycan.
1 more element
Dependencies are inferred from the claim text.