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WO2020124688A9 - Full-spectrum high-brightness and high-stability fluorescent dyes, and synthesis and application thereof - Google Patents

Full-spectrum high-brightness and high-stability fluorescent dyes, and synthesis and application thereof Download PDF

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Publication number
WO2020124688A9
WO2020124688A9 PCT/CN2019/000193 CN2019000193W WO2020124688A9 WO 2020124688 A9 WO2020124688 A9 WO 2020124688A9 CN 2019000193 W CN2019000193 W CN 2019000193W WO 2020124688 A9 WO2020124688 A9 WO 2020124688A9
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WO
WIPO (PCT)
Prior art keywords
dye
fluorescent
dyes
brightness
full
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Ceased
Application number
PCT/CN2019/000193
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French (fr)
Chinese (zh)
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WO2020124688A1 (en
Inventor
徐兆超
乔庆龙
周伟
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Dalian Institute of Chemical Physics of CAS
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Dalian Institute of Chemical Physics of CAS
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Publication of WO2020124688A1 publication Critical patent/WO2020124688A1/en
Publication of WO2020124688A9 publication Critical patent/WO2020124688A9/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • 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
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/10—Amino derivatives of triarylmethanes
    • C09B11/24—Phthaleins containing amino groups ; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/06—Ring systems of three rings
    • C07D221/14—Aza-phenalenes, e.g. 1,8-naphthalimide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
    • C07D473/18—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 one oxygen and one nitrogen atom, e.g. guanine
    • 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
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/28—Pyronines ; Xanthon, thioxanthon, selenoxanthan, telluroxanthon 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
    • 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
    • C09B57/08—Naphthalimide dyes; Phthalimide dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
    • G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
    • G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
    • G01N21/64—Fluorescence; Phosphorescence
    • G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1074—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1096—Heterocyclic compounds characterised by ligands containing other heteroatoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Immunology (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Analytical Chemistry (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Pathology (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)

Abstract

Provided in the present invention are full-spectrum high-brightness and high-stability fluorescent dyes, the dyes being one or several of the following mixed according to any ratio: 4-amido substituted naphthalimide dye, bisalkoxy substituted naphthalimide fluorescent dye, bisamino substituted naphthalimide fluorescent dye, 9, 10-bisamino substituted perylene imide, six-membered ring rhodamine dye, five-membered ring rhodamine dye, and silicon-based rhodamine dye. Compared to current commercial dyes, the fluorescent dyes of the present invention have higher photostability and narrower full width at half maximum (25 nm), and are not sensitive to various external environments including pH, polarity, and temperature. By means of the introduction of active groups such as click groups, protein tags, and drug molecules, the obtained functionalised fluorescent molecules have high biocompatibility, and can quickly and specifically dye living cells and bodies. Due to the increased photostability and fluorescent brightness, the present series of dyes can implement super-resolution fluorescence imaging in Storm, STED, and SIM modes.
PCT/CN2019/000193 2018-12-18 2019-10-10 Full-spectrum high-brightness and high-stability fluorescent dyes, and synthesis and application thereof Ceased WO2020124688A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN201811554135.7A CN111334079A (en) 2018-12-18 2018-12-18 Full-spectrum high-brightness and high-stability fluorescent dye and synthesis and application thereof
CN201811554135.7 2018-12-18

Publications (2)

Publication Number Publication Date
WO2020124688A1 WO2020124688A1 (en) 2020-06-25
WO2020124688A9 true WO2020124688A9 (en) 2020-07-30

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PCT/CN2019/000193 Ceased WO2020124688A1 (en) 2018-12-18 2019-10-10 Full-spectrum high-brightness and high-stability fluorescent dyes, and synthesis and application thereof

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CN (1) CN111334079A (en)
WO (1) WO2020124688A1 (en)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111825787B (en) * 2020-07-17 2022-04-05 苏州大学 Fluorescent Perchloroethylene for Analysis of Solvent Composition of H2O/DMF Mixed Solutions
CN112724085B (en) * 2021-01-11 2022-05-13 浙江大学 Pyrrole isoquinoline aggregation-induced fluorescent molecular probe and preparation and application thereof
CN113717544B (en) * 2021-09-23 2022-04-22 四川大学 Rapid and long-term lysosome or nucleus-targeted near-infrared staining reagent based on aminofluorene skeleton, preparation method and application thereof
CN116199662B (en) * 2021-11-30 2024-10-11 中国科学院大连化学物理研究所 Visible light and near infrared light rhodamine fluorescent quenching agent and synthesis and application thereof
CN115057853B (en) * 2022-06-08 2024-03-29 大连理工大学 A kind of naphthalimide donor-acceptor pure organic small molecule, its preparation method and charge transfer characterization method
CN115728280B (en) * 2022-12-07 2024-09-24 中国科学院新疆理化技术研究所 On-site detection method for synthesizing cannabinoid JWH-018
CN116621758B (en) * 2023-03-08 2025-07-29 东南大学 Multicolor fluorescent molecular switch and preparation method thereof
CN116144218B (en) * 2023-04-17 2023-07-14 北京高德品创科技有限公司 Infrared invisible ink for confidentiality and anti-counterfeiting and preparation method thereof
CN117143049B (en) * 2023-08-29 2025-02-14 浙江工业大学 A paclitaxel C(sp2)-H arylated derivative and its preparation method and application
WO2025090596A1 (en) * 2023-10-26 2025-05-01 Illumina, Inc. 4,5-substituted naphthalimide dyes and uses in nucleic acid sequencing
CN119320355B (en) * 2023-12-30 2025-11-21 中国医学科学院基础医学研究所 HnRNPA2B1 agonist and tumor prevention and treatment application thereof in combination with immune checkpoint inhibitor
CN119320353B (en) * 2023-12-30 2025-10-28 中国医学科学院基础医学研究所 HnRNPA2B1 agonist compound and application thereof in tumor prevention and treatment
CN119408274B (en) * 2025-01-07 2025-05-16 黄山天之都环境科技发展有限公司 Multi-spectrum composite profiling camouflage material and processing method thereof

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2012300319B8 (en) * 2011-08-26 2017-07-27 Alan Marc Kleinfeld Development and use of fluorescent probes of unbound bilirubin
WO2015102541A1 (en) * 2013-12-31 2015-07-09 Agency For Science, Technology And Research Optical biosensors for diagnosis and high-throughput drug screening using unique conformational changes of recombinant tagged g protein-coupled receptors for activation
CN106867515B (en) * 2015-12-11 2019-02-01 中国科学院大连化学物理研究所 A kind of fluorescence probe and its synthetic method and application for protein labeling and detection
CN107603269B (en) * 2016-07-11 2019-12-20 华东理工大学 Fluorescent dye based on naphthalimide, preparation method and application thereof
CN108069967B (en) * 2016-11-15 2020-03-27 中国科学院大连化学物理研究所 Fluorescent probe for intracellular protein labeling and synthetic method and application thereof
EP3548506A1 (en) * 2016-11-30 2019-10-09 Howard Hughes Medical Institute Chemigenetic voltage indicators

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CN111334079A (en) 2020-06-26
WO2020124688A1 (en) 2020-06-25

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