CN115996937B - 烷基吡啶正离子香豆素染料和在测序应用中的用途 - Google Patents

烷基吡啶正离子香豆素染料和在测序应用中的用途 Download PDF

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CN115996937B
CN115996937B CN202180045884.0A CN202180045884A CN115996937B CN 115996937 B CN115996937 B CN 115996937B CN 202180045884 A CN202180045884 A CN 202180045884A CN 115996937 B CN115996937 B CN 115996937B
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CN115996937A (zh
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E·克雷西娜
A·弗朗卡斯
刘小海
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Illumina Cambridge Ltd
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    • 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
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/14—Pyrrolo-pyrimidine radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
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    • 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"
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    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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    • 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
    • C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/1025—Heterocyclic compounds characterised by ligands
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    • G—PHYSICS
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    • 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)
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  • Genetics & Genomics (AREA)
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  • Wood Science & Technology (AREA)
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  • General Engineering & Computer Science (AREA)
  • General Physics & Mathematics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pathology (AREA)
  • Optics & Photonics (AREA)
  • Biophysics (AREA)
  • Microbiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Saccharide Compounds (AREA)
CN202180045884.0A 2020-12-17 2021-12-16 烷基吡啶正离子香豆素染料和在测序应用中的用途 Active CN115996937B (zh)

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US202063127044P 2020-12-17 2020-12-17
US63/127,044 2020-12-17
PCT/GB2021/053343 WO2022129930A1 (en) 2020-12-17 2021-12-16 Alkylpyridinium coumarin dyes and uses in sequencing applications

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CN115996937B true CN115996937B (zh) 2025-02-25

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Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
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
EP4689181A1 (en) 2023-03-30 2026-02-11 Illumina, Inc. Compositions and methods for nucleic acid 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
WO2026006985A1 (zh) * 2024-07-02 2026-01-08 深圳华大智造科技股份有限公司 一种红光区染料、其合成方法及其在基因测序中的应用

Family Cites Families (54)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8822228D0 (en) 1988-09-21 1988-10-26 Southern E M Support-bound oligonucleotides
US6346413B1 (en) 1989-06-07 2002-02-12 Affymetrix, Inc. Polymer arrays
US5800992A (en) 1989-06-07 1998-09-01 Fodor; Stephen P.A. Method of detecting nucleic acids
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
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
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
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
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
US6277628B1 (en) 1998-10-02 2001-08-21 Incyte Genomics, Inc. Linear microarrays
CA2370976C (en) 1999-04-20 2009-10-20 Illumina, Inc. Detection of nucleic acid reactions on bead 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
US6372813B1 (en) 1999-06-25 2002-04-16 Motorola Methods and compositions for attachment of biomolecules to solid supports, hydrogels, and hydrogel arrays
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
EP2607369B1 (en) 2002-08-23 2015-09-23 Illumina Cambridge Limited Modified nucleotides for polynucleotide sequencing
AU2003259352A1 (en) 2002-08-23 2004-03-11 Solexa Limited Labelled nucleotides
US7563907B2 (en) * 2002-12-05 2009-07-21 Dyomics Gmbh Compounds based on polymethines
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
FR2882059B1 (fr) * 2005-02-17 2007-03-23 Arkema Sa Objet moule presentant un effet multichromatique et dispositif lumineux associe
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
DE102008018132A1 (de) * 2008-04-09 2009-10-15 Henkel Ag & Co. Kgaa Kationische Direktzieher und Mittel zum Färben von keratinhaltigen Fasern
US9012022B2 (en) 2012-06-08 2015-04-21 Illumina, Inc. Polymer coatings
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
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
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

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CA3182253A1 (en) 2022-06-23
WO2022129930A1 (en) 2022-06-23
JP2023552933A (ja) 2023-12-20
US20220195196A1 (en) 2022-06-23
AU2021400060A1 (en) 2023-01-05
CN115996937A (zh) 2023-04-21
KR20230121555A (ko) 2023-08-18
EP4263721A1 (en) 2023-10-25

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