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WO1997000967A1 - Nouvelles amorces marquees au colorant, ribonucleotides, desoxyribonucleotides et didesoxyribonucleotides servant a effectuer une analyse automatique d'adn et a mettre en application des methodes de detection et d'amplification homogenes - Google Patents

Nouvelles amorces marquees au colorant, ribonucleotides, desoxyribonucleotides et didesoxyribonucleotides servant a effectuer une analyse automatique d'adn et a mettre en application des methodes de detection et d'amplification homogenes Download PDF

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Publication number
WO1997000967A1
WO1997000967A1 PCT/US1996/010729 US9610729W WO9700967A1 WO 1997000967 A1 WO1997000967 A1 WO 1997000967A1 US 9610729 W US9610729 W US 9610729W WO 9700967 A1 WO9700967 A1 WO 9700967A1
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WO
WIPO (PCT)
Prior art keywords
bodipy
fluorophore
fluorophores
labeled
polynucleotides
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.)
Ceased
Application number
PCT/US1996/010729
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English (en)
Inventor
Michael L. Metzker
Richard A. Gibbs
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.)
Baylor College of Medicine
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Baylor College of Medicine
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
Priority claimed from US08/494,216 external-priority patent/US5614386A/en
Priority claimed from US08/540,228 external-priority patent/US5861287A/en
Priority claimed from US08/553,936 external-priority patent/US5728529A/en
Priority claimed from US08/612,036 external-priority patent/US5994063A/en
Application filed by Baylor College of Medicine filed Critical Baylor College of Medicine
Priority to EP96921749A priority Critical patent/EP0833936A4/fr
Priority to AU62886/96A priority patent/AU699939B2/en
Publication of WO1997000967A1 publication Critical patent/WO1997000967A1/fr
Anticipated expiration legal-status Critical
Ceased 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
    • C12Q1/6813—Hybridisation assays
    • C12Q1/6816—Hybridisation assays characterised by the detection means
    • C12Q1/6818—Hybridisation assays characterised by the detection means involving interaction of two or more labels, e.g. resonant energy transfer
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H21/00—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
    • 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
    • C12Q1/6813—Hybridisation assays
    • C12Q1/6816—Hybridisation assays characterised by the detection means
    • 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

Definitions

  • This invention relates generally to methods for the use of a class of substituted 4,4-difluoro-4-bora-3A,4A-diaza-s-indacene (BODIPY ® fluorophore) compounds for improved DNA sequencing by chemical cleavage and by hybridization, labelling of DNA fragments for genetic analysis, improved DNA sequencing by the chain termination method of BODIPY ® fluorophore
  • a fluorescence detector then can be used to detect the fluorophore-labeled DNA fragments.
  • the four different dideoxy-terminated samples can be run in four separate lanes or, if labeled differentially, in the same lane.
  • BODIPY® dyes can replace one or more prior art dyes.
  • Dye-labeled oligonucleotides were purified using the following gradient conditions: 20% B, 5 minutes; 20% B-40% B, 30 minutes; 40% B- 100% B, 18 minutes; 100% B, ⁇ minutes at a flow rate of 1.0 ml per minute.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Immunology (AREA)
  • Microbiology (AREA)
  • Biophysics (AREA)
  • Analytical Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)

Abstract

L'invention concerne des procédés d'utilisation d'une catégorie de colorants, afin d'améliorer le séquençage d'ADN. On a décrit récemment une nouvelle catégorie de colorants, les fluorophores BODIPY®. La molécule hétérocyclique parente des fluorophores BODIPY® est un composé de difluorure de dipyrrométhènebore, qui est modifié afin de créer une catégorie importante de fluorophores à sélection spectrale. L'invention concerne des procédés d'utilisation d'ADN marqué au fluorophore BODIPY® servant à effectuer le séquençage d'amorces marquées au colorant, dans lequel les fluorophores BODIPY® sont fixés à l'extrémité 5' d'amorces de séquençage, des procédés de séquençage d'ADN utilisant de séquençage d'ADN en terminaison de chaîne, ainsi que de marquage interne de polynucléotides par incorporation enzymatique de ribonucléotides ou de désoxyribonucléotides à marquage fluorescent, ainsi que des oligonucléotides marqués par des composés de 4,4-difluoro-4-bora-3A,4A-diaza-s-indacène substitué (fluorophore BODIPY®), afin de mettre en application la méthode de Taqman. Les fluorophores BODIPY® présentent des caractéristiques spectrales améliorées par rapport aux colorants classiques de fluorescéine et de rhodamine. Les fluorophores BODIPY® possèdent une largeur de bande plus étroite, une insensibilité au solvant ou au pH, ainsi qu'une photostabilité améliorée et, de ce fait, permettent d'améliorer le séquençage et/ou la détection de l'ADN dans tout procédé nécessitant l'électrophorèse et la détection de l'ADN. De plus, les propriétés spectrales des fluorophores BODIPY® sont suffisamment semblables en longueur d'ondes et en intensité pour être utilisées avec l'équipement classique de l'état actuel de la technique.
PCT/US1996/010729 1995-06-23 1996-06-21 Nouvelles amorces marquees au colorant, ribonucleotides, desoxyribonucleotides et didesoxyribonucleotides servant a effectuer une analyse automatique d'adn et a mettre en application des methodes de detection et d'amplification homogenes Ceased WO1997000967A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP96921749A EP0833936A4 (fr) 1995-06-23 1996-06-21 Nouvelles amorces marquees au colorant, ribonucleotides, desoxyribonucleotides et didesoxyribonucleotides servant a effectuer une analyse automatique d'adn et a mettre en application des methodes de detection et d'amplification homogenes
AU62886/96A AU699939B2 (en) 1995-06-23 1996-06-21 Alternative dye-labeled primers, ribonucleotides, deoxyribonucleotides, and dideoxyribonucleotides for automated DNA analysis and homogeneous amplification/detection assays

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
US08/494,216 1995-06-23
US08/494,216 US5614386A (en) 1995-06-23 1995-06-23 Alternative dye-labeled primers for automated DNA sequencing
US08/540,228 US5861287A (en) 1995-06-23 1995-10-06 Alternative dye-labeled primers for automated DNA sequencing
US08/540,228 1995-10-06
US08/553,936 US5728529A (en) 1995-06-23 1995-11-06 Alternative dye-labeled ribonucleotides, deoxyribonucleotides, and dideoxyribonucleotides for automated DNA analysis
US08/553,936 1995-11-06
US08/612,036 1996-03-07
US08/612,036 US5994063A (en) 1995-06-23 1996-03-07 Substituted 4,4-difluoro-4-bora-3A,4A-diaza-s-indacene compounds for homogenous amplification/detection assays

Publications (1)

Publication Number Publication Date
WO1997000967A1 true WO1997000967A1 (fr) 1997-01-09

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1996/010729 Ceased WO1997000967A1 (fr) 1995-06-23 1996-06-21 Nouvelles amorces marquees au colorant, ribonucleotides, desoxyribonucleotides et didesoxyribonucleotides servant a effectuer une analyse automatique d'adn et a mettre en application des methodes de detection et d'amplification homogenes

Country Status (4)

Country Link
EP (1) EP0833936A4 (fr)
AU (1) AU699939B2 (fr)
CA (1) CA2225531A1 (fr)
WO (1) WO1997000967A1 (fr)

Cited By (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999016832A1 (fr) * 1997-10-01 1999-04-08 The Perkin-Elmer Corporation Colorants a base de xanthene a substitution aromatique
WO1999011813A3 (fr) * 1997-09-04 1999-05-06 Chiron Diagnostics Corp Sondes oligonucleotidiques portant des marqueurs a fluorescence extinguible et leurs procedes d'utilisation
WO2003048178A3 (fr) * 2001-11-29 2003-11-27 Amersham Biosciences Uk Ltd Analogues de nucleotides
WO2005054859A1 (fr) * 2003-12-01 2005-06-16 Fujirebio Inc. Biocapteur optique
US7155601B2 (en) 2001-02-14 2006-12-26 Intel Corporation Multi-element operand sub-portion shuffle instruction execution
EP2226330A1 (fr) * 2000-06-07 2010-09-08 Pacific Biosciences of California, Inc. Nucléotides à commutation de charge
US7893227B2 (en) 2006-12-05 2011-02-22 Lasergen, Inc. 3′-OH unblocked nucleotides and nucleosides base modified with non-cleavable, terminating groups and methods for their use in DNA sequencing
US7897737B2 (en) 2006-12-05 2011-03-01 Lasergen, Inc. 3′-OH unblocked, nucleotides and nucleosides, base modified with photocleavable, terminating groups and methods for their use in DNA sequencing
WO2011123820A2 (fr) 2010-04-02 2011-10-06 Pharmacophotonics, Inc. Nouveaux colorants à la rhodamine et conjugués
WO2011157432A1 (fr) 2010-06-18 2011-12-22 Roche Diagnostics Gmbh Adn polymérases présentant une discrimination accrue des mésappariements à l'extrémité 3'
WO2011157438A1 (fr) 2010-06-18 2011-12-22 Roche Diagnostics Gmbh Adn polymérases présentant une discrimination accrue des mésappariements à l'extrémité 3'
WO2011157435A1 (fr) 2010-06-18 2011-12-22 Roche Diagnostics Gmbh Adn polymérases présentant une discrimination accrue des mésappariements à l'extrémité 3'
WO2011157430A1 (fr) 2010-06-18 2011-12-22 Roche Diagnostics Gmbh Adn polymérases présentant une discrimination accrue des mésappariements à l'extrémité 3'
WO2011157437A1 (fr) 2010-06-18 2011-12-22 Roche Diagnostics Gmbh Adn polymérases présentant une discrimination accrue des mésappariements à l'extrémité 3'
WO2011157433A1 (fr) 2010-06-18 2011-12-22 Roche Diagnostics Gmbh Polymérases d'adn à discrimination accrue des non-concordances en 3'
WO2011157434A1 (fr) 2010-06-18 2011-12-22 Roche Diagnostics Gmbh Adn polymérases présentant une discrimination accrue des mésappariements à l'extrémité 3'
WO2011157436A1 (fr) 2010-06-18 2011-12-22 Roche Diagnostics Gmbh Adn polymérases présentant une discrimination accrue des mésappariements à l'extrémité 3'
US8148516B2 (en) 2000-06-07 2012-04-03 Pacific Biosciences Of California, Inc. Flowcell systems for single molecule detection
US8148503B2 (en) 2008-06-11 2012-04-03 Lasergen, Inc. Nucleotides and nucleosides and methods for their use in DNA sequencing
EP1816130A4 (fr) * 2004-11-08 2012-04-25 Riken Nouveau derive de nucleoside ou de nucleotide et son utilisation
WO2012110061A1 (fr) 2011-02-15 2012-08-23 Roche Diagnostics Gmbh Adn polymérases avec discrimination accrue des mésappariements à l'extrémité 3'
US8889860B2 (en) 2011-09-13 2014-11-18 Lasergen, Inc. 3′-OH unblocked, fast photocleavable terminating nucleotides and methods for nucleic acid sequencing
WO2025188906A1 (fr) * 2024-03-08 2025-09-12 Illumina, Inc. Nucléotides d'adénosine modifiés

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EP0233053A2 (fr) * 1986-02-07 1987-08-19 Applied Biosystems, Inc. Procédé pour la détection d'oligonucléotides séparés par électrophorèse
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NUCLEIC ACIDS RESEARCH, Volume 20, Number 10, issued 1992, L.G. LEE et al., "DNA Sequencing with Dye-Labeled Terminators and T7 DNA Polymerase: Effects of Dyes and dNTPs on Incorporation of Dye-Terminators and Probability Analysis of Termination Fragments", pages 2471-2483. *
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See also references of EP0833936A4 *

Cited By (40)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6465175B2 (en) 1997-09-04 2002-10-15 Bayer Corporation Oligonucleotide probes bearing quenchable fluorescent labels, and methods of use thereof
WO1999011813A3 (fr) * 1997-09-04 1999-05-06 Chiron Diagnostics Corp Sondes oligonucleotidiques portant des marqueurs a fluorescence extinguible et leurs procedes d'utilisation
WO1999016832A1 (fr) * 1997-10-01 1999-04-08 The Perkin-Elmer Corporation Colorants a base de xanthene a substitution aromatique
EP1441011A1 (fr) * 1997-10-01 2004-07-28 Applera Corporation Colorant à transfert d'énergie contenant un colorant xanthène à substitution aromatique comme colorant donneur et/ou accepteur
US6008379A (en) * 1997-10-01 1999-12-28 The Perkin-Elmer Corporation Aromatic-substituted xanthene dyes
EP3112478A1 (fr) * 2000-06-07 2017-01-04 Pacific Biosciences of California, Inc. Procédé de séquençage d'acides nucléiques basé sur des nucléotides à commutation de charges
EP2634263A1 (fr) * 2000-06-07 2013-09-04 Pacific Biosciences of California, Inc. Procédé de séquençage d'acides nucléiques à base de nucléotides à commutation de charge
US8148516B2 (en) 2000-06-07 2012-04-03 Pacific Biosciences Of California, Inc. Flowcell systems for single molecule detection
EP2226330A1 (fr) * 2000-06-07 2010-09-08 Pacific Biosciences of California, Inc. Nucléotides à commutation de charge
EP1287154A4 (fr) * 2000-06-07 2010-12-15 Pacific Biosciences California Nucleotides a commutation de charges
US7155601B2 (en) 2001-02-14 2006-12-26 Intel Corporation Multi-element operand sub-portion shuffle instruction execution
WO2003048178A3 (fr) * 2001-11-29 2003-11-27 Amersham Biosciences Uk Ltd Analogues de nucleotides
WO2005054859A1 (fr) * 2003-12-01 2005-06-16 Fujirebio Inc. Biocapteur optique
EP1816130A4 (fr) * 2004-11-08 2012-04-25 Riken Nouveau derive de nucleoside ou de nucleotide et son utilisation
US7897737B2 (en) 2006-12-05 2011-03-01 Lasergen, Inc. 3′-OH unblocked, nucleotides and nucleosides, base modified with photocleavable, terminating groups and methods for their use in DNA sequencing
US7964352B2 (en) 2006-12-05 2011-06-21 Lasergen, Inc. 3′-OH unblocked nucleotides and nucleosides, base modified with labels and photocleavable, terminating groups and methods for their use in DNA sequencing
US7893227B2 (en) 2006-12-05 2011-02-22 Lasergen, Inc. 3′-OH unblocked nucleotides and nucleosides base modified with non-cleavable, terminating groups and methods for their use in DNA sequencing
US8969535B2 (en) 2006-12-05 2015-03-03 Lasergen, Inc. Photocleavable labeled nucleotides and nucleosides and methods for their use in DNA sequencing
US8361727B2 (en) 2006-12-05 2013-01-29 Lasergen, Inc. 3′OH-unblocked, nucleotides and nucleosides base modified with labels and photocleavable, terminating groups and methods for their use in DNA sequencing
US8198029B2 (en) 2006-12-05 2012-06-12 Lasergen, Inc 3'-OH unblocked nucleotides and nucleosides base modified with non-cleavable, terminating groups and methods for their use in DNA sequencing
US8877905B2 (en) 2008-06-11 2014-11-04 Lasergen, Inc. Nucleotides and nucleosides and methods for their use in DNA sequencing
US8497360B2 (en) 2008-06-11 2013-07-30 Lasergen, Inc. Nucleotides and nucleosides and methods for their use in DNA sequencing
US8148503B2 (en) 2008-06-11 2012-04-03 Lasergen, Inc. Nucleotides and nucleosides and methods for their use in DNA sequencing
US9200319B2 (en) 2008-06-11 2015-12-01 Lasergen, Inc. Nucleotides and nucleosides and methods for their use in DNA sequencing
WO2011123820A2 (fr) 2010-04-02 2011-10-06 Pharmacophotonics, Inc. Nouveaux colorants à la rhodamine et conjugués
WO2011157437A1 (fr) 2010-06-18 2011-12-22 Roche Diagnostics Gmbh Adn polymérases présentant une discrimination accrue des mésappariements à l'extrémité 3'
WO2011157432A1 (fr) 2010-06-18 2011-12-22 Roche Diagnostics Gmbh Adn polymérases présentant une discrimination accrue des mésappariements à l'extrémité 3'
WO2011157430A1 (fr) 2010-06-18 2011-12-22 Roche Diagnostics Gmbh Adn polymérases présentant une discrimination accrue des mésappariements à l'extrémité 3'
WO2011157436A1 (fr) 2010-06-18 2011-12-22 Roche Diagnostics Gmbh Adn polymérases présentant une discrimination accrue des mésappariements à l'extrémité 3'
WO2011157435A1 (fr) 2010-06-18 2011-12-22 Roche Diagnostics Gmbh Adn polymérases présentant une discrimination accrue des mésappariements à l'extrémité 3'
WO2011157438A1 (fr) 2010-06-18 2011-12-22 Roche Diagnostics Gmbh Adn polymérases présentant une discrimination accrue des mésappariements à l'extrémité 3'
WO2011157434A1 (fr) 2010-06-18 2011-12-22 Roche Diagnostics Gmbh Adn polymérases présentant une discrimination accrue des mésappariements à l'extrémité 3'
WO2011157433A1 (fr) 2010-06-18 2011-12-22 Roche Diagnostics Gmbh Polymérases d'adn à discrimination accrue des non-concordances en 3'
WO2012110061A1 (fr) 2011-02-15 2012-08-23 Roche Diagnostics Gmbh Adn polymérases avec discrimination accrue des mésappariements à l'extrémité 3'
US9399798B2 (en) 2011-09-13 2016-07-26 Lasergen, Inc. 3′-OH unblocked, fast photocleavable terminating nucleotides and methods for nucleic acid sequencing
US8889860B2 (en) 2011-09-13 2014-11-18 Lasergen, Inc. 3′-OH unblocked, fast photocleavable terminating nucleotides and methods for nucleic acid sequencing
US9689035B2 (en) 2011-09-13 2017-06-27 Lasergen, Inc. 3′-OH unblocked, fast photocleavable terminating nucleotides and methods for nucleic acid sequencing
US10041115B2 (en) 2011-09-13 2018-08-07 Lasergen, Inc. 3′-OH unblocked, fast photocleavable terminating nucleotides and methods for nucleic acid sequencing
US11001886B2 (en) 2011-09-13 2021-05-11 Agilent Technologies, Inc. 3′-OH unblocked, fast photocleavable terminating nucleotides and methods for nucleic acid sequencing
WO2025188906A1 (fr) * 2024-03-08 2025-09-12 Illumina, Inc. Nucléotides d'adénosine modifiés

Also Published As

Publication number Publication date
EP0833936A1 (fr) 1998-04-08
EP0833936A4 (fr) 2005-03-02
AU6288696A (en) 1997-01-22
AU699939B2 (en) 1998-12-17
CA2225531A1 (fr) 1997-01-09

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