CN117295751A - 含有双硼稠合杂环的荧光染料及其在测序中的用途 - Google Patents

含有双硼稠合杂环的荧光染料及其在测序中的用途 Download PDF

Info

Publication number
CN117295751A
CN117295751A CN202280032974.0A CN202280032974A CN117295751A CN 117295751 A CN117295751 A CN 117295751A CN 202280032974 A CN202280032974 A CN 202280032974A CN 117295751 A CN117295751 A CN 117295751A
Authority
CN
China
Prior art keywords
nucleotide
substituted
group
unsubstituted
alkyl
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
CN202280032974.0A
Other languages
English (en)
Chinese (zh)
Inventor
M·卡灵厄姆
N·N·罗曼诺夫
刘小海
J·皮科斯
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
Illumina Cambridge Ltd
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 Illumina Cambridge Ltd filed Critical Illumina Cambridge Ltd
Publication of CN117295751A publication Critical patent/CN117295751A/zh
Pending legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02Boron compounds
    • C07F5/027Organoboranes and organoborohydrides
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02Boron compounds
    • C07F5/022Boron compounds without C-boron linkages
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H23/00Compounds containing boron, silicon or a metal, e.g. chelates or vitamin B12
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/02Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
    • C09B23/04Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00Other synthetic dyes of known constitution
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12QMEASURING 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
    • C12Q1/00Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
    • C12Q1/68Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving nucleic acids
    • C12Q1/6869Methods for sequencing
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12QMEASURING 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
    • C12Q2563/00Nucleic acid detection characterized by the use of physical, structural and functional properties
    • C12Q2563/107Nucleic acid detection characterized by the use of physical, structural and functional properties fluorescence

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Analytical Chemistry (AREA)
  • Immunology (AREA)
  • Microbiology (AREA)
  • Biophysics (AREA)
  • Physics & Mathematics (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
CN202280032974.0A 2021-05-05 2022-05-02 含有双硼稠合杂环的荧光染料及其在测序中的用途 Pending CN117295751A (zh)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US202163184429P 2021-05-05 2021-05-05
US63/184,429 2021-05-05
PCT/EP2022/061723 WO2022233795A1 (en) 2021-05-05 2022-05-02 Fluorescent dyes containing bis-boron fused heterocycles and uses in sequencing

Publications (1)

Publication Number Publication Date
CN117295751A true CN117295751A (zh) 2023-12-26

Family

ID=81940432

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202280032974.0A Pending CN117295751A (zh) 2021-05-05 2022-05-02 含有双硼稠合杂环的荧光染料及其在测序中的用途

Country Status (8)

Country Link
US (2) US12043637B2 (enExample)
EP (1) EP4334327A1 (enExample)
JP (1) JP2024516191A (enExample)
KR (1) KR102884006B1 (enExample)
CN (1) CN117295751A (enExample)
AU (1) AU2022269804A1 (enExample)
CA (1) CA3215598A1 (enExample)
WO (1) WO2022233795A1 (enExample)

Families Citing this family (17)

* 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
EP4499862A1 (en) 2022-03-28 2025-02-05 Illumina, Inc. Labeled avidin and methods for sequencing
AU2023244351A1 (en) 2022-03-31 2024-01-18 Illumina, Inc. Nucleosides and nucleotides with 3' vinyl blocking group useful in sequencing by synthesis
EP4499870A1 (en) 2022-03-31 2025-02-05 Illumina, Inc. Compositions and methods for improving sequencing signals
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
CA3246536A1 (en) * 2022-12-22 2024-06-27 Illumina, Inc. TRANSITION METAL CATALYST COMPOSITIONS AND SYNTHETIC SEQUENCE PROCESSES
AU2023409219A1 (en) 2022-12-22 2024-10-03 Illumina, Inc. Palladium catalyst compositions and methods for sequencing by synthesis
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
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
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

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108516985A (zh) * 2018-05-23 2018-09-11 安徽师范大学 吡咯吡啶肼双氟硼强荧光染料及其制备方法和应用
CN108530474A (zh) * 2018-05-23 2018-09-14 安徽师范大学 一类吡咯腙肼双氟硼强荧光染料及其制备方法

Family Cites Families (58)

* 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
US6156501A (en) 1993-10-26 2000-12-05 Affymetrix, Inc. Arrays of modified nucleic acid probes and methods of use
DE69433180T2 (de) 1993-10-26 2004-06-24 Affymetrix, Inc., Santa Clara Felder von nukleinsaeuresonden auf biologischen chips
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
US6031078A (en) 1998-06-16 2000-02-29 Millennium Pharmaceuticals, Inc. MTbx protein and nucleic acid molecules and uses therefor
GB0002310D0 (en) 2000-02-01 2000-03-22 Solexa Ltd Polynucleotide sequencing
WO2000006770A1 (en) 1998-07-30 2000-02-10 Solexa Ltd. Arrayed biomolecules and their use in 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
CA2370976C (en) 1999-04-20 2009-10-20 Illumina, Inc. Detection of nucleic acid reactions on bead arrays
US6355431B1 (en) 1999-04-20 2002-03-12 Illumina, Inc. Detection of nucleic acid amplification reactions using 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
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
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
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
US20160272657A1 (en) 2013-11-20 2016-09-22 Christopher J. Ziegler Highly fluorescent pyrrole-bf2 chromophores
GB201414098D0 (en) 2014-08-08 2014-09-24 Illumina Cambridge Ltd Modified nucleotide linkers
CA3048486A1 (en) 2017-01-04 2018-07-12 Complete Genomics, Inc. Stepwise sequencing by non-labeled reversible terminators or natural nucleotides
RU2736384C1 (ru) 2017-03-07 2020-11-16 Иллюмина, Инк. Секвенирование с помощью одиночного источника света и двух оптических каналов
CA3103719A1 (en) 2018-10-31 2020-05-07 Illumina, Inc. Polymerases, compositions, and methods of use
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
CA3103739A1 (en) 2018-12-05 2020-06-11 Illumina, Inc. Polymerases, compositions, and methods of use
US11293061B2 (en) 2018-12-26 2022-04-05 Illumina Cambridge Limited Sequencing methods using nucleotides with 3′ AOM blocking group
US20220403450A1 (en) 2021-06-03 2022-12-22 Illumina Software, Inc. Systems and methods for sequencing nucleotides using two optical channels

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108516985A (zh) * 2018-05-23 2018-09-11 安徽师范大学 吡咯吡啶肼双氟硼强荧光染料及其制备方法和应用
CN108530474A (zh) * 2018-05-23 2018-09-14 安徽师范大学 一类吡咯腙肼双氟硼强荧光染料及其制备方法

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
JIANG, XINDONG等: "Synthesis, properties and application of novel 5, 6, 5, 6-tetracyclic pyrazine/pyrrole-fused unsymmetric bis(BF2) fluorescent dyes: BOPYPYs", CHINESE CHEMICAL LETTERS, vol. 30, no. 12, 31 December 2019 (2019-12-31), pages 2271 - 2273, XP085964301, DOI: 10.1016/j.cclet.2019.07.027 *

Also Published As

Publication number Publication date
EP4334327A1 (en) 2024-03-13
US20240352048A1 (en) 2024-10-24
KR20240004502A (ko) 2024-01-11
CA3215598A1 (en) 2022-11-10
WO2022233795A1 (en) 2022-11-10
KR102884006B1 (ko) 2025-11-10
US20220380389A1 (en) 2022-12-01
JP2024516191A (ja) 2024-04-12
AU2022269804A1 (en) 2023-11-02
US12043637B2 (en) 2024-07-23

Similar Documents

Publication Publication Date Title
CN115916908B (zh) 长斯托克斯位移色烯并喹啉染料及其在测序应用中的用途
KR102884006B1 (ko) 비스-붕소 융합 헤테로사이클을 함유하는 형광 염료 및 서열분석에서의 용도
KR102865446B1 (ko) 삼차 아민 치환된 쿠마린 화합물 및 형광 표지로서의 이의 용도
KR102829192B1 (ko) 엑소사이클릭 아민 치환된 쿠마린 화합물 및 형광 표지로서의 이의 용도
JP7307686B2 (ja) 第二級アミン置換クマリン化合物、および蛍光標識としてのそれらの使用
EP3559004B1 (en) Coumarin compounds and their uses as fluorescent labels
JP2023539411A (ja) 置換クマリン色素及び蛍光標識としての使用
US12552814B2 (en) Fluorescent dyes containing fused tetracyclic bis-boron heterocycle and uses in sequencing
CN115996937B (zh) 烷基吡啶正离子香豆素染料和在测序应用中的用途
CN119301275A (zh) 用于核酸测序的组合物和方法
CN119213083A (zh) 用于减少测序期间的光损伤的组合物和方法
US12631560B2 (en) Chromenoquinoline dyes and uses in sequencing
US20260138994A1 (en) Fluorescent dyes containing fused tetracyclic bis-boron heterocycle and uses in sequencing
US20230313292A1 (en) Chromenoquinoline dyes and uses in sequencing
US20250215494A1 (en) Tricyclic polymethine dyes for nucleic acid sequencing
CN119452044A (zh) 萘酰亚胺染料以及其在核酸测序中的用途
HK40008386B (en) Coumarin compounds and their uses as fluorescent labels
HK40008386A (en) Coumarin compounds and their uses as fluorescent labels
HK1218752A1 (en) Polymethine compounds and their use as fluorescent labels
HK1218752B (en) Polymethine compounds and their use as fluorescent labels

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
WD01 Invention patent application deemed withdrawn after publication
WD01 Invention patent application deemed withdrawn after publication

Application publication date: 20231226