CN109476654B - 新的荧光染料及其作为生物标志物的用途 - Google Patents

新的荧光染料及其作为生物标志物的用途 Download PDF

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CN109476654B
CN109476654B CN201780042127.1A CN201780042127A CN109476654B CN 109476654 B CN109476654 B CN 109476654B CN 201780042127 A CN201780042127 A CN 201780042127A CN 109476654 B CN109476654 B CN 109476654B
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CN109476654A (zh
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尼古拉·罗曼诺夫
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Illumina Cambridge Ltd
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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
    • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
    • C09B62/36—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to some other heterocyclic ring
    • C09B62/365—Specific dyes not provided for in groups C09B62/38 - C09B62/42
    • 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
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-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
    • 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
    • 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

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  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
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  • Bioinformatics & Cheminformatics (AREA)
  • General Health & Medical Sciences (AREA)
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  • Immunology (AREA)
  • Biotechnology (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • General Engineering & Computer Science (AREA)
  • Microbiology (AREA)
  • Genetics & Genomics (AREA)
  • Analytical Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pyrane Compounds (AREA)
  • Luminescent Compositions (AREA)
  • Saccharide Compounds (AREA)
CN201780042127.1A 2016-09-30 2017-09-29 新的荧光染料及其作为生物标志物的用途 Active CN109476654B (zh)

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Application Number Priority Date Filing Date Title
US201662402635P 2016-09-30 2016-09-30
US62/402,635 2016-09-30
PCT/EP2017/074880 WO2018060482A1 (en) 2016-09-30 2017-09-29 New fluorescent dyes and their uses as biomarkers

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CN109476654A CN109476654A (zh) 2019-03-15
CN109476654B true CN109476654B (zh) 2022-06-10

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EP (2) EP3519410B1 (enExample)
JP (2) JP7002478B2 (enExample)
KR (2) KR102582172B1 (enExample)
CN (1) CN109476654B (enExample)
AU (2) AU2017335223B2 (enExample)
CA (1) CA3026019C (enExample)
ES (2) ES2914688T3 (enExample)
IL (2) IL263871B2 (enExample)
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Families Citing this family (44)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10385214B2 (en) 2016-09-30 2019-08-20 Illumina Cambridge Limited Fluorescent dyes and their uses as biomarkers
GB201716931D0 (en) * 2017-10-16 2017-11-29 Illumina Cambridge Ltd New fluorescent compounds and their use as biomarkers
WO2020010495A1 (zh) * 2018-07-09 2020-01-16 深圳华大智造极创科技有限公司 核酸测序方法
US11293061B2 (en) 2018-12-26 2022-04-05 Illumina Cambridge Limited Sequencing methods using nucleotides with 3′ AOM blocking group
CA3103636A1 (en) * 2019-03-01 2020-09-10 Illumina Cambridge Limited Tertiary amine substituted coumarin compounds and their uses as fluorescent labels
CN112654681B (zh) * 2019-03-01 2023-01-06 伊卢米纳剑桥有限公司 环外胺取代的香豆素化合物及其作为荧光标记物的用途
NL2023327B1 (en) 2019-03-01 2020-09-17 Illumina Inc Multiplexed fluorescent detection of analytes
WO2020178231A1 (en) 2019-03-01 2020-09-10 Illumina, Inc. Multiplexed fluorescent detection of analytes
MY208607A (en) 2019-11-27 2025-05-20 Illumina Cambridge Ltd Cyclooctatetraene containing dyes and compositions
IL297992B2 (en) 2020-06-22 2025-03-01 Illumina Cambridge Ltd 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
US20220195196A1 (en) 2020-12-17 2022-06-23 Illumina Cambridge Limited Alkylpyridinium coumarin dyes and uses in sequencing applications
US20220195517A1 (en) 2020-12-17 2022-06-23 Illumina Cambridge Limited Long stokes shift chromenoquinoline dyes and uses in sequencing applications
US20220195516A1 (en) 2020-12-17 2022-06-23 Illumina Cambridge Limited Methods, systems and compositions for nucleic acid sequencing
US20220195518A1 (en) 2020-12-22 2022-06-23 Illumina Cambridge Limited Methods and compositions for nucleic acid sequencing
CN114671842B (zh) * 2020-12-24 2024-05-28 郑州思昆生物工程有限公司 一种荧光化合物及其制备方法、荧光修饰核苷酸、试剂盒
AU2022277632A1 (en) 2021-05-20 2023-11-09 Illumina Cambridge Limited Compositions and methods for sequencing by synthesis
US20220403450A1 (en) 2021-06-03 2022-12-22 Illumina Software, Inc. Systems and methods for sequencing nucleotides using two optical channels
CN117580961A (zh) 2021-09-01 2024-02-20 Illumina公司 用于加速碱基判读的幅度调制
US20230183799A1 (en) 2021-12-10 2023-06-15 Illumina, Inc. Parallel sample and index sequencing
JP2025509651A (ja) 2022-03-15 2025-04-11 イルミナ インコーポレイテッド 並行サンプル及びインデックス配列決定
US20230304086A1 (en) 2022-03-28 2023-09-28 Illumina Cambridge Limited Labeled avidin and methods for sequencing
US20230314322A1 (en) 2022-03-29 2023-10-05 Illumina, Inc. Systems and methods of sequencing polynucleotides
CA3223128A1 (en) 2022-03-31 2023-10-05 Illumina, Inc. Compositions and methods for improving sequencing signals
EP4499659A1 (en) 2022-03-31 2025-02-05 Illumina, Inc. Nucleosides and nucleotides with 3' vinyl blocking group useful in sequencing by synthesis
US20230383342A1 (en) 2022-05-31 2023-11-30 Illumina Cambridge Limited Compositions and methods for nucleic acid sequencing
CA3259955A1 (en) 2022-06-28 2024-01-04 Illumina, Inc. FLUORESCENT DYES CONTAINING A FUSIONED BIS-TETRACYCLIC BORON HETEROCYCLE AND THEIR USES IN SEQUENCED
EP4594428A2 (en) 2022-09-30 2025-08-06 Illumina, Inc. Compositions and methods for reducing photo damage during sequencing
AU2023409219A1 (en) 2022-12-22 2024-10-03 Illumina, Inc. Palladium catalyst compositions and methods for sequencing by synthesis
WO2024137765A1 (en) 2022-12-22 2024-06-27 Illumina, Inc. Transition-metal catalyst compositions and methods for sequencing by synthesis
US20240271206A1 (en) 2022-12-27 2024-08-15 Illumina, Inc. Methods of sequencing using 3' allyl blocked nucleotides
US20240327910A1 (en) 2023-03-29 2024-10-03 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
EP4781416A1 (en) 2023-09-20 2026-07-29 Illumina, Inc. Methods for sequencing
EP4781417A1 (en) 2023-09-20 2026-07-29 Illumina, Inc. Sequencing error identification and correction
US20250137048A1 (en) 2023-10-26 2025-05-01 Illumina, Inc. 4,5-substituted naphthalimide dyes and uses in 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
WO2026020407A1 (zh) * 2024-07-25 2026-01-29 深圳华大智造科技股份有限公司 一种提高分辨率的分子探针、其修饰的核酸以及在基因测序中的应用
WO2026136132A1 (en) 2024-12-16 2026-06-25 Illumina, Inc. Multi-dye attached polyphosphodiester scaffolds for use in sequencing

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4035740A (en) * 1974-03-13 1977-07-12 Bayer Aktiengesellschaft Dyestuff laser
WO2000050525A1 (en) * 1999-02-25 2000-08-31 Day-Glo Color Corp. Ink jet printing inks
WO2007135368A2 (en) * 2006-05-18 2007-11-29 Solexa Limited Dye compounds and the use of their labelled conjugates
CN105263918A (zh) * 2013-03-08 2016-01-20 伊鲁米纳剑桥有限公司 罗丹明化合物及其作为荧光标记物的用途

Family Cites Families (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5302509A (en) 1989-08-14 1994-04-12 Beckman Instruments, Inc. Method for sequencing polynucleotides
US5846719A (en) 1994-10-13 1998-12-08 Lynx Therapeutics, Inc. Oligonucleotide tags for sorting and identification
EP2327797B1 (en) 1997-04-01 2015-11-25 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
AU770831B2 (en) 1998-07-30 2004-03-04 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
US6391937B1 (en) 1998-11-25 2002-05-21 Motorola, Inc. Polyacrylamide hydrogels and hydrogel arrays made from polyacrylamide reactive prepolymers
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
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
AU2003259350A1 (en) 2002-08-23 2004-03-11 Solexa Limited Modified nucleotides for polynucleotide sequencing
EP3147292B1 (en) 2002-08-23 2018-09-26 Illumina Cambridge Limited Labelled nucleotides
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
EP2789383B1 (en) 2004-01-07 2023-05-03 Illumina Cambridge Limited Molecular arrays
JP4990886B2 (ja) 2005-05-10 2012-08-01 ソレックサ リミテッド 改良ポリメラーゼ
GB0517097D0 (en) 2005-08-19 2005-09-28 Solexa Ltd Modified nucleosides and nucleotides and uses thereof
US9453258B2 (en) 2011-09-23 2016-09-27 Illumina, Inc. Methods and compositions for nucleic acid sequencing
US9085698B2 (en) 2011-09-23 2015-07-21 Illumina Cambridge Limited Dyes for labelling molecular ligands
US9012022B2 (en) 2012-06-08 2015-04-21 Illumina, Inc. Polymer coatings
ES2685549T3 (es) 2013-03-15 2018-10-09 Illumina Cambridge Limited Nucleósidos o nucleótidos modificados
US10385214B2 (en) 2016-09-30 2019-08-20 Illumina Cambridge Limited Fluorescent dyes and their uses as biomarkers

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4035740A (en) * 1974-03-13 1977-07-12 Bayer Aktiengesellschaft Dyestuff laser
WO2000050525A1 (en) * 1999-02-25 2000-08-31 Day-Glo Color Corp. Ink jet printing inks
WO2007135368A2 (en) * 2006-05-18 2007-11-29 Solexa Limited Dye compounds and the use of their labelled conjugates
CN105263918A (zh) * 2013-03-08 2016-01-20 伊鲁米纳剑桥有限公司 罗丹明化合物及其作为荧光标记物的用途

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Inhibition of amyloid-β aggregation by coumarin analogs can be manipulated by functionalization of the aromatic center;Deborah D. Soto-Ortega et al.;《Bioorganic & Medicinal Chemistry》;20110312;第19卷;第2596-2602页 *

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ES2988726T3 (es) 2024-11-21
IL263871B2 (en) 2023-04-01
AU2022268273B2 (en) 2024-06-13
JP2019531255A (ja) 2019-10-31
CA3026019A1 (en) 2018-04-05
US11370920B2 (en) 2022-06-28
US20210071005A1 (en) 2021-03-11
US20190367738A1 (en) 2019-12-05
EP3974425A1 (en) 2022-03-30
EP3974425B1 (en) 2024-07-10
AU2017335223A1 (en) 2018-12-20
CA3026019C (en) 2022-05-17
WO2018060482A1 (en) 2018-04-05
JP2022050495A (ja) 2022-03-30
NZ748812A (en) 2020-11-27
IL297749A (en) 2022-12-01
US10844225B2 (en) 2020-11-24
US20180094140A1 (en) 2018-04-05
KR102473054B1 (ko) 2022-11-30
KR20190057021A (ko) 2019-05-27
ES2914688T3 (es) 2022-06-15
KR20220160714A (ko) 2022-12-06
EP3519410B1 (en) 2022-03-30
IL297749B2 (en) 2025-10-01
EP3519410A1 (en) 2019-08-07
AU2017335223B2 (en) 2022-08-11
JP7002478B2 (ja) 2022-02-10
IL297749B1 (en) 2025-06-01
AU2022268273A1 (en) 2022-12-15
IL263871B (en) 2022-12-01
CN109476654A (zh) 2019-03-15
SG11201810633WA (en) 2018-12-28
KR102582172B1 (ko) 2023-09-22
IL263871A (en) 2019-01-31
US10385214B2 (en) 2019-08-20

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