CA3182088A1 - Substituted coumarin dyes and uses as fluorescent labels - Google Patents

Substituted coumarin dyes and uses as fluorescent labels

Info

Publication number
CA3182088A1
CA3182088A1 CA3182088A CA3182088A CA3182088A1 CA 3182088 A1 CA3182088 A1 CA 3182088A1 CA 3182088 A CA3182088 A CA 3182088A CA 3182088 A CA3182088 A CA 3182088A CA 3182088 A1 CA3182088 A1 CA 3182088A1
Authority
CA
Canada
Prior art keywords
alkyl
compound
optionally substituted
nucleotide
substituted
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
CA3182088A
Other languages
English (en)
French (fr)
Inventor
Nikolai Nikolaevich Romanov
Michael Callingham
Carole ANASTASI
Patrick Mccauley
Niall HYNES
Natasha CRAKE
Xiaolin Wu
Xiaohai Liu
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Illumina Cambridge Ltd
Original Assignee
Individual
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Publication of CA3182088A1 publication Critical patent/CA3182088A1/en
Pending legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
    • C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
    • C12Q1/68—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving nucleic acids
    • C12Q1/6876—Nucleic acid products used in the analysis of nucleic acids, e.g. primers or probes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • 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
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent materials, e.g. electroluminescent or chemiluminescent
    • C09K11/06—Luminescent materials, e.g. electroluminescent or chemiluminescent containing organic luminescent materials
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
    • C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
    • C12Q1/68—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving nucleic acids
    • C12Q1/6869—Methods for sequencing
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
    • C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
    • C12Q1/68—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving nucleic acids
    • C12Q1/6869—Methods for sequencing
    • C12Q1/6874—Methods for sequencing involving nucleic acid arrays, e.g. sequencing by hybridisation
    • 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
    • C09K2211/1018—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
    • C09K2211/1088—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
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
    • C12Q2535/00—Reactions characterised by the assay type for determining the identity of a nucleotide base or a sequence of oligonucleotides
    • C12Q2535/101—Sanger sequencing method, i.e. oligonucleotide sequencing using primer elongation and dideoxynucleotides as chain terminators
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
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    • C12Q2563/00—Nucleic acid detection characterized by the use of physical, structural and functional properties
    • C12Q2563/107—Nucleic acid detection characterized by the use of physical, structural and functional properties fluorescence
    • 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"
    • G01N2021/6439—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" with indicators, stains, dyes, tags, labels, marks

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Physics & Mathematics (AREA)
  • Analytical Chemistry (AREA)
  • Immunology (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Biophysics (AREA)
  • Molecular Biology (AREA)
  • Microbiology (AREA)
  • Biotechnology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • Genetics & Genomics (AREA)
  • Materials Engineering (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pathology (AREA)
  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
  • Pyrane Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Luminescent Compositions (AREA)
  • Saccharide Compounds (AREA)
  • Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
  • Apparatus Associated With Microorganisms And Enzymes (AREA)
CA3182088A 2020-07-28 2021-07-27 Substituted coumarin dyes and uses as fluorescent labels Pending CA3182088A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US202063057758P 2020-07-28 2020-07-28
US63/057,758 2020-07-28
PCT/EP2021/071024 WO2022023353A1 (en) 2020-07-28 2021-07-27 Substituted coumarin dyes and uses as fluorescent labels

Publications (1)

Publication Number Publication Date
CA3182088A1 true CA3182088A1 (en) 2022-02-03

Family

ID=77447854

Family Applications (1)

Application Number Title Priority Date Filing Date
CA3182088A Pending CA3182088A1 (en) 2020-07-28 2021-07-27 Substituted coumarin dyes and uses as fluorescent labels

Country Status (12)

Country Link
US (3) US11981964B2 (enExample)
EP (1) EP4188921A1 (enExample)
JP (1) JP2023539411A (enExample)
KR (1) KR102776582B1 (enExample)
CN (1) CN115867544A (enExample)
AU (1) AU2021314837A1 (enExample)
BR (1) BR112022026802A2 (enExample)
CA (1) CA3182088A1 (enExample)
IL (1) IL298805A (enExample)
MX (1) MX2022014722A (enExample)
WO (1) WO2022023353A1 (enExample)
ZA (1) ZA202213353B (enExample)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11293061B2 (en) 2018-12-26 2022-04-05 Illumina Cambridge Limited Sequencing methods using nucleotides with 3′ AOM blocking group
JP2023510454A (ja) 2019-11-27 2023-03-14 イルミナ ケンブリッジ リミテッド シクロオクタテトラエンを含有する色素及び組成物
WO2021259881A1 (en) 2020-06-22 2021-12-30 Illumina Cambridge Limited Nucleosides and nucleotides with 3' acetal blocking group
US11981964B2 (en) 2020-07-28 2024-05-14 Illumina Cambridge Limited Substituted coumarin dyes and uses as fluorescent labels
CN112778258B (zh) * 2021-01-05 2022-02-01 苏州大学 酰胺衍生物中性线粒体荧光标记物及其制备方法和应用
CN117916390A (zh) 2021-05-20 2024-04-19 伊鲁米纳公司 用于边合成边测序的组合物和方法
WO2023034079A1 (en) 2021-09-01 2023-03-09 Illumina Software, Inc. Amplitude modulation for accelerated base calling
EP4499862A1 (en) 2022-03-28 2025-02-05 Illumina, Inc. Labeled avidin and methods for sequencing
EP4499870A1 (en) 2022-03-31 2025-02-05 Illumina, Inc. Compositions and methods for improving sequencing signals
AU2023244351A1 (en) 2022-03-31 2024-01-18 Illumina, Inc. Nucleosides and nucleotides with 3' vinyl blocking group useful in sequencing by synthesis
AU2023281871A1 (en) 2022-05-31 2024-11-14 Illumina, Inc Compositions and methods for nucleic acid sequencing
CN119213083A (zh) 2022-09-30 2024-12-27 伊路米纳有限公司 用于减少测序期间的光损伤的组合物和方法
CN119095984A (zh) 2022-12-27 2024-12-06 伊路米纳有限公司 使用3'烯丙基封端的核苷酸的测序方法
AU2024247164A1 (en) * 2023-03-29 2024-12-12 Illumina, Inc. Naphthalimide dyes and uses in nucleic acid sequencing
EP4689181A1 (en) 2023-03-30 2026-02-11 Illumina, Inc. Compositions and methods for nucleic acid sequencing
US20250075269A1 (en) 2023-08-31 2025-03-06 Illumina, Inc. Compositions and methods for nucleic acid sequencing
WO2025136890A1 (en) 2023-12-18 2025-06-26 Illumina, Inc. Hydrogel nanoparticles as labeling scaffold in sequencing
US20250215493A1 (en) 2023-12-28 2025-07-03 Illumina, Inc. Nucleotides with enzymatically cleavable 3'-o-glycoside blocking groups for sequencing
WO2025184226A1 (en) 2024-02-28 2025-09-04 Illumina, Inc. Nucleotides with terminal phosphate capping
WO2025188906A1 (en) 2024-03-08 2025-09-12 Illumina, Inc. Modified adenosine nucleotides
WO2025221895A1 (en) 2024-04-19 2025-10-23 Illumina, Inc. Water soluble polymer scaffolds for dye labeling
WO2025230914A1 (en) 2024-04-29 2025-11-06 Illumina, Inc. Nucleotides with enzyme-triggered self-immolative linkers for sequencing by synthesis

Family Cites Families (78)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2807761A1 (de) * 1978-02-23 1979-08-30 Basf Ag Cumarinderivate
DE3609804A1 (de) * 1986-03-22 1987-09-24 Basf Ag Thiazolyl-cyan-cumarine und ihre verwendung zur flaechenmaessigen konzentrierung von licht
US5268486A (en) 1986-04-18 1993-12-07 Carnegie-Mellon Unversity Method for labeling and detecting materials employing arylsulfonate cyanine dyes
GB8822228D0 (en) 1988-09-21 1988-10-26 Southern E M Support-bound oligonucleotides
US5800992A (en) 1989-06-07 1998-09-01 Fodor; Stephen P.A. Method of detecting nucleic acids
US6346413B1 (en) 1989-06-07 2002-02-12 Affymetrix, Inc. Polymer arrays
DE3924454A1 (de) 1989-07-24 1991-02-07 Cornelis P Prof Dr Hollenberg Die anwendung von dna und dna-technologie fuer die konstruktion von netzwerken zur verwendung in der chip-konstruktion und chip-produktion (dna chips)
US5302509A (en) 1989-08-14 1994-04-12 Beckman Instruments, Inc. Method for sequencing polynucleotides
DE3933903A1 (de) 1989-10-11 1991-04-18 Basf Ag Fluoreszenzpigmente
DK0604552T3 (da) 1991-09-18 1997-08-04 Affymax Tech Nv Fremgangsmåde til syntese af forskellige samlinger af oligomerer
US5677195A (en) 1991-11-22 1997-10-14 Affymax Technologies N.V. Combinatorial strategies for polymer synthesis
AU3728093A (en) 1992-02-19 1993-09-13 Public Health Research Institute Of The City Of New York, Inc., The Novel oligonucleotide arrays and their use for sorting, isolating, sequencing, and manipulating nucleic acids
US5583211A (en) 1992-10-29 1996-12-10 Beckman Instruments, Inc. Surface activated organic polymers useful for location - specific attachment of nucleic acids, peptides, proteins and oligosaccharides
DE4302459A1 (de) * 1993-01-29 1994-08-04 Bayer Ag Sulfocumarinhaltige Nukleotide und deren Verwendung in Nachweisverfahren für Nukleinsäuren
US5472672A (en) 1993-10-22 1995-12-05 The Board Of Trustees Of The Leland Stanford Junior University Apparatus and method for polymer synthesis using arrays
DE69433180T2 (de) 1993-10-26 2004-06-24 Affymetrix, Inc., Santa Clara Felder von nukleinsaeuresonden auf biologischen chips
US6156501A (en) 1993-10-26 2000-12-05 Affymetrix, Inc. Arrays of modified nucleic acid probes and methods of use
US5429807A (en) 1993-10-28 1995-07-04 Beckman Instruments, Inc. Method and apparatus for creating biopolymer arrays on a solid support surface
US5807522A (en) 1994-06-17 1998-09-15 The Board Of Trustees Of The Leland Stanford Junior University Methods for fabricating microarrays of biological samples
US5846719A (en) 1994-10-13 1998-12-08 Lynx Therapeutics, Inc. Oligonucleotide tags for sorting and identification
US5556752A (en) 1994-10-24 1996-09-17 Affymetrix, Inc. Surface-bound, unimolecular, double-stranded DNA
US5624711A (en) 1995-04-27 1997-04-29 Affymax Technologies, N.V. Derivatization of solid supports and methods for oligomer synthesis
US5545531A (en) 1995-06-07 1996-08-13 Affymax Technologies N.V. Methods for making a device for concurrently processing multiple biological chip assays
WO1997014028A2 (en) 1995-10-11 1997-04-17 Luminex Corporation Multiplexed analysis of clinical specimens apparatus and method
US5658734A (en) 1995-10-17 1997-08-19 International Business Machines Corporation Process for synthesizing chemical compounds
US6458530B1 (en) 1996-04-04 2002-10-01 Affymetrix Inc. Selecting tag nucleic acids
US6297006B1 (en) 1997-01-16 2001-10-02 Hyseq, Inc. Methods for sequencing repetitive sequences and for determining the order of sequence subfragments
EP1591541B1 (en) 1997-04-01 2012-02-15 Illumina Cambridge Limited Method of nucleic acid sequencing
US6465178B2 (en) 1997-09-30 2002-10-15 Surmodics, Inc. Target molecule attachment to surfaces
US6485944B1 (en) 1997-10-10 2002-11-26 President And Fellows Of Harvard College Replica amplification of nucleic acid arrays
US6087102A (en) 1998-01-07 2000-07-11 Clontech Laboratories, Inc. Polymeric arrays and methods for their use in binding assays
US6287776B1 (en) 1998-02-02 2001-09-11 Signature Bioscience, Inc. Method for detecting and classifying nucleic acid hybridization
JP3944996B2 (ja) 1998-03-05 2007-07-18 株式会社日立製作所 Ｄｎａプローブアレー
US6780591B2 (en) * 1998-05-01 2004-08-24 Arizona Board Of Regents Method of determining the nucleotide sequence of oligonucleotides and DNA molecules
US6031078A (en) 1998-06-16 2000-02-29 Millennium Pharmaceuticals, Inc. MTbx protein and nucleic acid molecules and uses therefor
WO2000006770A1 (en) 1998-07-30 2000-02-10 Solexa Ltd. Arrayed biomolecules and their use in sequencing
GB0002310D0 (en) 2000-02-01 2000-03-22 Solexa Ltd Polynucleotide sequencing
AR021833A1 (es) 1998-09-30 2002-08-07 Applied Research Systems Metodos de amplificacion y secuenciacion de acido nucleico
US6277628B1 (en) 1998-10-02 2001-08-21 Incyte Genomics, Inc. Linear microarrays
US6391937B1 (en) 1998-11-25 2002-05-21 Motorola, Inc. Polyacrylamide hydrogels and hydrogel arrays made from polyacrylamide reactive prepolymers
US6355431B1 (en) 1999-04-20 2002-03-12 Illumina, Inc. Detection of nucleic acid amplification reactions using bead arrays
CA2370976C (en) 1999-04-20 2009-10-20 Illumina, Inc. Detection of nucleic acid reactions on bead arrays
US6372813B1 (en) 1999-06-25 2002-04-16 Motorola Methods and compositions for attachment of biomolecules to solid supports, hydrogels, and hydrogel arrays
US6664061B2 (en) 1999-06-25 2003-12-16 Amersham Biosciences Ab Use and evaluation of a [2+2] photoaddition in immobilization of oligonucleotides on a three-dimensional hydrogel matrix
US6770441B2 (en) 2000-02-10 2004-08-03 Illumina, Inc. Array compositions and methods of making same
AU2001279244A1 (en) 2000-08-09 2002-02-18 Motorola, Inc. The use and evaluation of a (2+2) photocycloaddition in immobilization of oligonucleotides on a three-dimensional hydrogel matrix
ATE352586T2 (de) 2000-09-29 2007-02-15 Molecular Probes Inc Modifizierte carbocyaninfarbstoffe und deren konjugate
US7057026B2 (en) * 2001-12-04 2006-06-06 Solexa Limited Labelled nucleotides
US20060122387A1 (en) * 2002-06-13 2006-06-08 Cti Europe S.R.L. Derivatives of chromen-2-one as inhibitors of vegf production in mammalian cells
AU2003259352A1 (en) 2002-08-23 2004-03-11 Solexa Limited Labelled nucleotides
EP2607369B1 (en) 2002-08-23 2015-09-23 Illumina Cambridge Limited Modified nucleotides for polynucleotide sequencing
DE10258150A1 (de) 2002-12-10 2004-07-08 Dyomics Gmbh Hydrophile Marker auf der Basis von Benzopyrylo-Polymethinen
GB0321306D0 (en) 2003-09-11 2003-10-15 Solexa Ltd Modified polymerases for improved incorporation of nucleotide analogues
GB0326073D0 (en) 2003-11-07 2003-12-10 Solexa Ltd Improvements in or relating to polynucleotide arrays
US20110059865A1 (en) 2004-01-07 2011-03-10 Mark Edward Brennan Smith Modified Molecular Arrays
US8623628B2 (en) 2005-05-10 2014-01-07 Illumina, Inc. Polymerases
GB0517097D0 (en) 2005-08-19 2005-09-28 Solexa Ltd Modified nucleosides and nucleotides and uses thereof
US8431416B2 (en) * 2009-04-01 2013-04-30 Becton, Dickinson And Company Reactive heterocycle-substituted 7-hydroxycoumarins and their conjugates
CN103079558B (zh) * 2010-04-05 2025-09-12 上海复星医药产业发展有限公司 IRE-1α抑制剂
EP3623481B1 (en) 2011-09-23 2021-08-25 Illumina, Inc. Compositions for nucleic acid sequencing
US9012022B2 (en) 2012-06-08 2015-04-21 Illumina, Inc. Polymer coatings
EP2964612B1 (en) 2013-03-08 2017-02-01 Illumina Cambridge Limited Polymethine compounds and their use as fluorescent labels
KR102230831B1 (ko) 2013-03-15 2021-03-22 일루미나 케임브리지 리미티드 변형된 뉴클레오사이드 또는 뉴클레오타이드
GB201414098D0 (en) 2014-08-08 2014-09-24 Illumina Cambridge Ltd Modified nucleotide linkers
CN104449669B (zh) * 2014-10-15 2016-11-23 中山大学 一种多芳基取代咪唑荧光探针及其制备方法和在检测g-四链体结构中的应用
JP6470984B2 (ja) * 2015-01-27 2019-02-13 学校法人東日本学園 アロマターゼ阻害剤及びこれを含む医薬
CN104610251B (zh) * 2015-01-29 2017-08-18 浙江工业大学 一种香豆素类化合物及其制备方法和应用
GB201516987D0 (en) 2015-09-25 2015-11-11 Illumina Cambridge Ltd Polymethine compounds and their use as fluorescent labels
ITUA20161706A1 (it) * 2016-03-15 2017-09-15 Cyanagen S R L Nuovi coloranti cumarinici e relativi coniugati
US10385214B2 (en) 2016-09-30 2019-08-20 Illumina Cambridge Limited Fluorescent dyes and their uses as biomarkers
CN109476674B (zh) * 2016-12-22 2021-12-10 伊鲁米纳剑桥有限公司 香豆素化合物及其作为荧光标记物的用途
CA3048486A1 (en) 2017-01-04 2018-07-12 Complete Genomics, Inc. Stepwise sequencing by non-labeled reversible terminators or natural nucleotides
GB201716931D0 (en) 2017-10-16 2017-11-29 Illumina Cambridge Ltd New fluorescent compounds and their use as biomarkers
CN120082639A (zh) 2018-11-09 2025-06-03 深圳华大智造科技股份有限公司 使用未标记的核苷酸进行大规模平行测序
US11293061B2 (en) 2018-12-26 2022-04-05 Illumina Cambridge Limited Sequencing methods using nucleotides with 3′ AOM blocking group
MY209343A (en) 2019-03-01 2025-07-03 Illumina Cambridge Ltd Exocyclic amine substituted coumarin compounds and uses as fluorescent labels
KR102865446B1 (ko) 2019-03-01 2025-09-29 일루미나 케임브리지 리미티드 삼차 아민 치환된 쿠마린 화합물 및 형광 표지로서의 이의 용도
US11981964B2 (en) 2020-07-28 2024-05-14 Illumina Cambridge Limited Substituted coumarin dyes and uses as fluorescent labels

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