KR102676814B1 - 접합 그룹을 포함하는 수용성 형광 또는 착색 염료 - Google Patents
접합 그룹을 포함하는 수용성 형광 또는 착색 염료 Download PDFInfo
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- KR102676814B1 KR102676814B1 KR1020177027123A KR20177027123A KR102676814B1 KR 102676814 B1 KR102676814 B1 KR 102676814B1 KR 1020177027123 A KR1020177027123 A KR 1020177027123A KR 20177027123 A KR20177027123 A KR 20177027123A KR 102676814 B1 KR102676814 B1 KR 102676814B1
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- 239000000975 dye Substances 0.000 title claims abstract description 49
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- 150000001875 compounds Chemical class 0.000 claims abstract description 163
- 150000003839 salts Chemical class 0.000 claims abstract description 34
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 151
- -1 sulfhydryl alkyl ether Chemical class 0.000 claims description 136
- 125000000217 alkyl group Chemical group 0.000 claims description 64
- 229910019142 PO4 Inorganic materials 0.000 claims description 59
- 239000010452 phosphate Substances 0.000 claims description 59
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 52
- 125000003118 aryl group Chemical group 0.000 claims description 43
- 125000001072 heteroaryl group Chemical group 0.000 claims description 33
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 claims description 31
- 125000001424 substituent group Chemical group 0.000 claims description 25
- 125000002947 alkylene group Chemical group 0.000 claims description 24
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- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 2
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- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
- WZYNTGFFWDNWGG-UHFFFAOYSA-N n,n-dimethyl-2-(2-phenylethenyl)aniline Chemical compound CN(C)C1=CC=CC=C1C=CC1=CC=CC=C1 WZYNTGFFWDNWGG-UHFFFAOYSA-N 0.000 claims description 2
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- 239000005020 polyethylene terephthalate Substances 0.000 claims description 2
- HSSLDCABUXLXKM-UHFFFAOYSA-N resorufin Chemical compound C1=CC(=O)C=C2OC3=CC(O)=CC=C3N=C21 HSSLDCABUXLXKM-UHFFFAOYSA-N 0.000 claims description 2
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052707 ruthenium Inorganic materials 0.000 claims description 2
- ACOJCCLIDPZYJC-UHFFFAOYSA-M thiazole orange Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.C1=CC=C2C(C=C3N(C4=CC=CC=C4S3)C)=CC=[N+](C)C2=C1 ACOJCCLIDPZYJC-UHFFFAOYSA-M 0.000 claims description 2
- 125000003342 alkenyl group Chemical class 0.000 claims 6
- 125000000304 alkynyl group Chemical class 0.000 claims 6
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 claims 6
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical compound C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 claims 1
- 125000004057 biotinyl group Chemical group [H]N1C(=O)N([H])[C@]2([H])[C@@]([H])(SC([H])([H])[C@]12[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 claims 1
- 125000001207 fluorophenyl group Chemical group 0.000 claims 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 claims 1
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- FPKVOQKZMBDBKP-UHFFFAOYSA-N 1-[4-[(2,5-dioxopyrrol-1-yl)methyl]cyclohexanecarbonyl]oxy-2,5-dioxopyrrolidine-3-sulfonic acid Chemical compound O=C1C(S(=O)(=O)O)CC(=O)N1OC(=O)C1CCC(CN2C(C=CC2=O)=O)CC1 FPKVOQKZMBDBKP-UHFFFAOYSA-N 0.000 description 15
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- 125000005580 triphenylene group Chemical group 0.000 description 1
- 239000001226 triphosphate Substances 0.000 description 1
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- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/65515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/572—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/093—Polyol derivatives esterified at least twice by phosphoric acid groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/094—Esters of phosphoric acids with arylalkanols
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/02—Coumarine dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
- C09B69/101—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing an anthracene dye
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
- C09B69/101—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing an anthracene dye
- C09B69/102—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing an anthracene dye containing a perylene dye
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
- C09B69/103—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing a diaryl- or triarylmethane dye
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
- C09B69/109—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing other specific dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
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| US62/121,415 | 2015-02-26 | ||
| PCT/US2016/019907 WO2016138461A1 (en) | 2015-02-26 | 2016-02-26 | Water soluble fluorescent or colored dyes comprising conjugating groups |
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| KR20170120677A KR20170120677A (ko) | 2017-10-31 |
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| EP3094687B1 (en) | 2014-01-16 | 2020-02-12 | Sony Corporation | Water soluble fluorescent or colored dyes |
| CN107406353A (zh) | 2015-02-26 | 2017-11-28 | 索尼公司 | 苯基乙炔基萘染料和用于它们用途的方法 |
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| US11434377B2 (en) | 2016-04-01 | 2022-09-06 | Sony Corporation | Ultra bright dimeric or polymeric dyes with rigid spacing groups |
| EP3436529A1 (en) | 2016-04-01 | 2019-02-06 | Sony Corporation | Ultra bright dimeric or polymeric dyes |
| KR102756931B1 (ko) * | 2016-04-06 | 2025-01-21 | 소니그룹주식회사 | 스페이싱 링커 그룹을 포함하는 초고명도 이량체성 또는 중합체성 염료 |
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| CN109071961B (zh) | 2016-05-11 | 2021-04-27 | 索尼公司 | 超亮二聚或聚合染料 |
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| EP3639013A4 (en) | 2017-06-16 | 2021-06-30 | Duke University | Resonator networks for improved label detection, computation, analyte sensing, and tunable random number generation |
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| KR20200067132A (ko) | 2017-10-05 | 2020-06-11 | 소니 주식회사 | 프로그램가능한 중합체성 약물 |
| CN111836645A (zh) | 2017-11-16 | 2020-10-27 | 索尼公司 | 可编程的聚合药物 |
| US12194104B2 (en) | 2018-01-12 | 2025-01-14 | Sony Group Corporation | Phosphoalkyl ribose polymers comprising biologically active compounds |
| JP2021510696A (ja) | 2018-01-12 | 2021-04-30 | ソニー株式会社 | 生物学的に活性な化合物を含む剛性間隔基を有するポリマー |
| EP4137818B1 (en) | 2018-03-19 | 2025-12-10 | Sony Group Corporation | Use of divalent metals for enhancement of fluorescent signals |
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| JP2021519841A (ja) | 2018-03-30 | 2021-08-12 | ベクトン・ディキンソン・アンド・カンパニーＢｅｃｔｏｎ， Ｄｉｃｋｉｎｓｏｎ Ａｎｄ Ｃｏｍｐａｎｙ | ペンダントクロモフォアを有する水溶性ポリマー色素 |
| CN112313242A (zh) * | 2018-06-27 | 2021-02-02 | 索尼公司 | 具有含脱氧核糖的连接体基团的聚合物染料 |
| EP3952918A1 (en) | 2019-04-11 | 2022-02-16 | Sony Group Corporation | Programmable polymeric drugs |
| KR20210152524A (ko) | 2019-04-11 | 2021-12-15 | 소니그룹주식회사 | 프로그램 가능한 중합체성 약물 |
| KR20210152523A (ko) | 2019-04-11 | 2021-12-15 | 소니그룹주식회사 | 프로그램 가능한 중합체성 약물 |
| JP7239904B2 (ja) | 2019-09-26 | 2023-03-15 | ソニーグループ株式会社 | リンカー基を有するポリマータンデム色素 |
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| EP4251764A1 (en) | 2020-11-25 | 2023-10-04 | Sony Group Corporation | Polymer dyes |
| JP2023552448A (ja) | 2020-12-07 | 2023-12-15 | ソニーグループ株式会社 | 二量体色素又はポリマー色素における輝度を増強するためのスペーシングリンカー基の設計 |
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