CA2368495A1 - Electron-deficient nitrogen heterocycle-substituted fluorescein dyes - Google Patents

Electron-deficient nitrogen heterocycle-substituted fluorescein dyes Download PDF

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Publication number
CA2368495A1
CA2368495A1 CA002368495A CA2368495A CA2368495A1 CA 2368495 A1 CA2368495 A1 CA 2368495A1 CA 002368495 A CA002368495 A CA 002368495A CA 2368495 A CA2368495 A CA 2368495A CA 2368495 A1 CA2368495 A1 CA 2368495A1
Authority
CA
Canada
Prior art keywords
electron
nitrogen heterocycle
fluorescein dyes
deficient nitrogen
substituted fluorescein
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.)
Granted
Application number
CA002368495A
Other languages
French (fr)
Other versions
CA2368495C (en
Inventor
Krishna G. Upadhya
Steven M. Menchen
Weiguo Zhen
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.)
Applied Biosystems LLC
Original Assignee
Applera Corporation
Krishna G. Upadhya
Steven M. Menchen
Weiguo Zhen
Pe Corporation
Applied Biosystems Inc.
Applied Biosystems, Llc
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 Applera Corporation, Krishna G. Upadhya, Steven M. Menchen, Weiguo Zhen, Pe Corporation, Applied Biosystems Inc., Applied Biosystems, Llc filed Critical Applera Corporation
Publication of CA2368495A1 publication Critical patent/CA2368495A1/en
Application granted granted Critical
Publication of CA2368495C publication Critical patent/CA2368495C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • 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
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/06—Hydroxy derivatives of triarylmethanes in which at least one OH group is bound to an aryl nucleus and their ethers or esters
    • C09B11/08—Phthaleins; Phenolphthaleins; Fluorescein
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S436/00—Chemistry: analytical and immunological testing
    • Y10S436/80—Fluorescent dyes, e.g. rhodamine

Abstract

The invention provides compositions electron-deficient nitrogen heterocycle-substituted fluorescein dyes and meth-ods in which the dyes are conjugated to substrates and used as detection labels in molecular biology experiments. The electron-de-ficient nitrogen heterocycles include pyridine, quinoline, pyrazine, and the like. Substrates include polynucleotides, nucleosides, nucleotides, peptides, proteins, carbohydrates, and ligands.
CA002368495A 2000-02-07 2001-02-05 Electron-deficient nitrogen heterocycle-substituted fluorescein dyes Expired - Lifetime CA2368495C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US09/498,702 2000-02-07
US09/498,702 US6221604B1 (en) 2000-02-07 2000-02-07 Electron-deficient nitrogen heterocycle-substituted fluorescein dyes
PCT/US2001/003772 WO2001057264A2 (en) 2000-02-07 2001-02-05 Electron-deficient nitrogen heterocycle-substituted fluorescein dyes

Publications (2)

Publication Number Publication Date
CA2368495A1 true CA2368495A1 (en) 2001-08-09
CA2368495C CA2368495C (en) 2009-09-29

Family

ID=23982139

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002368495A Expired - Lifetime CA2368495C (en) 2000-02-07 2001-02-05 Electron-deficient nitrogen heterocycle-substituted fluorescein dyes

Country Status (9)

Country Link
US (2) US6221604B1 (en)
EP (1) EP1196640B1 (en)
JP (5) JP2003521571A (en)
AT (1) ATE258992T1 (en)
AU (1) AU772739B2 (en)
CA (1) CA2368495C (en)
DE (1) DE60101939T2 (en)
ES (1) ES2211768T3 (en)
WO (1) WO2001057264A2 (en)

Families Citing this family (53)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6221604B1 (en) * 2000-02-07 2001-04-24 Pe Corporation Electron-deficient nitrogen heterocycle-substituted fluorescein dyes
US6811979B2 (en) * 2000-10-11 2004-11-02 Applera Corporation Fluorescent nucleobase conjugates having anionic linkers
US6887690B2 (en) 2001-06-22 2005-05-03 Pe Corporation Dye-labeled ribonucleotide triphosphates
US6972339B2 (en) 2001-09-07 2005-12-06 Epoch Biosciences, Inc. Compounds and methods for fluorescent labeling
US8569516B2 (en) * 2001-09-07 2013-10-29 Elitech Holding B.V. Compounds and methods for fluorescent labeling
WO2003040395A2 (en) * 2001-11-07 2003-05-15 Applera Corporation Universal nucleotides for nucleic acid analysis
US20030148284A1 (en) * 2001-12-17 2003-08-07 Vision Todd J. Solid phase detection of nucleic acid molecules
US7026166B2 (en) * 2002-01-22 2006-04-11 Chiron Corporation Fluorogenic dyes
US7074597B2 (en) * 2002-07-12 2006-07-11 The Trustees Of Columbia University In The City Of New York Multiplex genotyping using solid phase capturable dideoxynucleotides and mass spectrometry
US7704756B2 (en) * 2003-01-21 2010-04-27 Novartis Vaccines And Diagnostics, Inc. Fluorogenic dyes
WO2004092412A2 (en) 2003-03-31 2004-10-28 Roche Diagnostics Gmbh Compositions and methods for detecting certain flaviviruses, including members of the japanese encephalitis virus serogroup
US7399639B2 (en) * 2003-05-04 2008-07-15 Massachusetts Institute Of Technology Sensors, and methods of making and using the same
US7417726B2 (en) * 2003-09-19 2008-08-26 Applied Biosystems Inc. Normalization of data using controls
US20060029948A1 (en) * 2003-09-19 2006-02-09 Gary Lim Sealing cover and dye compatibility selection
US7570443B2 (en) 2003-09-19 2009-08-04 Applied Biosystems, Llc Optical camera alignment
US7541454B2 (en) * 2003-10-24 2009-06-02 Epoch Biosciences, Inc. Compounds and methods for fluorescent labeling
WO2005056613A2 (en) * 2003-12-08 2005-06-23 The Research Foundation Of State University Of New York Site selectively tagged and templated molecularly imprinted polymers for sensor applications
JP4127204B2 (en) * 2003-12-17 2008-07-30 セイコーエプソン株式会社 Manufacturing method of liquid crystal display device
CA2552520A1 (en) * 2004-01-07 2005-07-28 The Research Foundation Of State University Of New York Protein imprinted polymers with integrated emission sites
WO2005077125A2 (en) * 2004-02-11 2005-08-25 Applera Corporation Methods and compositions for detecting nucleic acids
US7939251B2 (en) 2004-05-06 2011-05-10 Roche Molecular Systems, Inc. SENP1 as a marker for cancer
US20050255485A1 (en) * 2004-05-14 2005-11-17 Livak Kenneth J Detection of gene duplications
PL1748767T3 (en) 2004-05-28 2012-08-31 Unigen Inc 1-(3-methyl-2,4-dimethoxyphenyl)-3-(2',4'-dihydroxyphenyl)-propane as a potent tyrosinase inhibitor
US7767834B2 (en) * 2004-08-13 2010-08-03 Elitech Holding B.V. Phosphonylated fluorescent dyes and conjugates
CA2577053A1 (en) * 2004-08-13 2006-02-23 Epoch Biosciences, Inc. Phosphonate fluorescent dyes and conjugates
US20060252079A1 (en) * 2005-05-03 2006-11-09 Applera Corporation Fluorescent detection system and dye set for use therewith
JP2011504505A (en) * 2007-11-21 2011-02-10 デコード ジェネティクス イーエイチエフ Biaryl PDE4 inhibitors for treating pulmonary and cardiovascular disorders
PL3542780T3 (en) * 2008-07-21 2022-05-02 Unigen, Inc. Series of skin-whitening (lightening) compounds
KR101718994B1 (en) * 2009-09-16 2017-03-23 포항공과대학교 산학협력단 A chemodosimeter approach to fluorescent sensing and imaging of inorganic and methylmercury species
US20130078148A1 (en) 2010-06-07 2013-03-28 Konica Minolta Holdings, Inc. Near field-enhanced fluorescence sensor chip
WO2012023391A1 (en) 2010-08-17 2012-02-23 コニカミノルタホールディングス株式会社 Spfs sensor equipped with non-specific adsorption type purification mechanism
WO2012092403A1 (en) 2010-12-29 2012-07-05 Life Technologies Corporation Ddao compounds as fluorescent reference standards
EP2688860B1 (en) 2011-03-24 2020-12-09 Unigen, Inc. Compounds and methods for preparation of diarylpropanes
EP2801626B1 (en) 2011-05-24 2016-04-06 ELITechGroup B.V. Detection of methicillin-resistant staphylococcus aureus
CN102321063B (en) * 2011-07-19 2015-07-01 华东理工大学 Method for preparing unsymmetrical rhodamine
US20140170772A1 (en) 2011-07-28 2014-06-19 Konica Minolta Inc Method for Measuring Amount of Analyte and Device for SPFS
CN103012354A (en) * 2012-12-24 2013-04-03 广州医药研究总院 Preparation method of 5(6)-carboxyl carboxyl luciferin isomer
JP2016510991A (en) 2013-03-11 2016-04-14 エリテックグループ・ベスローテン・フェンノートシャップＥｌｉｔｅｃｈｇｒｏｕｐ Ｂ．Ｖ． Method for accurate strand displacement isothermal amplification
WO2014186147A2 (en) 2013-05-13 2014-11-20 Elitech Holding B.V. Droplet digital pcr with short minor groove probes
CN103508941B (en) * 2013-10-29 2015-07-22 郑州大学 2,4-diphenyl-5,6-bis(2-pyridyl)-phenol and preparation method thereof
EP3230467A1 (en) 2014-12-12 2017-10-18 ELITechGroup B.V. Methods and compositions for detecting antibiotic resistant bacteria
JP2017538418A (en) 2014-12-12 2017-12-28 エリテックグループ・ベスローテン・フェンノートシャップＥｌｉｔｅｃｈｇｒｏｕｐ Ｂ．Ｖ． Methods and compositions for detecting antibiotic-resistant bacteria
EP3247797B1 (en) 2015-01-12 2020-04-29 Life Technologies Corporation Methods, systems and compositions thereof for nucleic acid library quality control and quantification
JP6675758B2 (en) * 2015-02-20 2020-04-01 国立大学法人名古屋大学 Phosphafluorescein compound or salt thereof, or fluorescent dye using the same
WO2019069885A1 (en) 2017-10-02 2019-04-11 コニカミノルタ株式会社 Method for detecting analyte
KR20210107737A (en) 2018-12-20 2021-09-01 라이프 테크놀로지스 코포레이션 Modified rhodamine dyes and their use in biological assays
CN113195639A (en) 2018-12-20 2021-07-30 生命技术公司 Asymmetric rhodamine dyes and their use in bioassays
WO2021080629A1 (en) 2019-10-23 2021-04-29 Elitechgroup, Inc. Methods for true isothermal strand displacement amplification
WO2021092408A1 (en) * 2019-11-08 2021-05-14 The University Of North Carolina At Charlotte Asymmetric donor-acceptor molecular dyes
WO2021111820A1 (en) 2019-12-06 2021-06-10 コニカミノルタ株式会社 Standard substance for psa quantification, preparation method therefor, standard solution for psa quantification, and psa quantification method
CN116075597A (en) 2020-07-23 2023-05-05 生命技术公司 Energy transfer dye conjugates for use in bioassays
CA3186950A1 (en) 2020-07-23 2022-01-27 Scott Benson Compositions, systems and methods for biological analysis involving energy transfer dye conjugates and analytes comprising the same
CN113563360A (en) * 2021-08-16 2021-10-29 中国科学技术大学 Amphiphilic fluorescent dye and synthetic method and application thereof

Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4318846A (en) 1979-09-07 1982-03-09 Syva Company Novel ether substituted fluorescein polyamino acid compounds as fluorescers and quenchers
US5047519A (en) 1986-07-02 1991-09-10 E. I. Du Pont De Nemours And Company Alkynylamino-nucleotides
CA1340806C (en) 1986-07-02 1999-11-02 James Merrill Prober Method, system and reagents for dna sequencing
US5188934A (en) 1989-11-14 1993-02-23 Applied Biosystems, Inc. 4,7-dichlorofluorescein dyes as molecular probes
US5654442A (en) * 1989-11-14 1997-08-05 The Perkin-Elmer Corporation 4,7-dichlorofluorescein dyes as molecular probes
JPH08505121A (en) 1992-09-03 1996-06-04 アプライド バイオシステムズ，インコーポレイテッド 4,7-Dichlorofluorescein dye as molecular probe
US5538848A (en) 1994-11-16 1996-07-23 Applied Biosystems Division, Perkin-Elmer Corp. Method for detecting nucleic acid amplification using self-quenching fluorescence probe
US5654419A (en) 1994-02-01 1997-08-05 The Regents Of The University Of California Fluorescent labels and their use in separations
US5453505A (en) 1994-06-30 1995-09-26 Biometric Imaging, Inc. N-heteroaromatic ion and iminium ion substituted cyanine dyes for use as fluorescence labels
US6020481A (en) * 1996-04-01 2000-02-01 The Perkin-Elmer Corporation Asymmetric benzoxanthene dyes
US5945526A (en) 1996-05-03 1999-08-31 Perkin-Elmer Corporation Energy transfer dyes with enhanced fluorescence
US5863727A (en) 1996-05-03 1999-01-26 The Perkin-Elmer Corporation Energy transfer dyes with enhanced fluorescence
US5800996A (en) 1996-05-03 1998-09-01 The Perkin Elmer Corporation Energy transfer dyes with enchanced fluorescence
US5821356A (en) 1996-08-12 1998-10-13 The Perkin Elmer Corporation Propargylethoxyamino nucleotides
US5770716A (en) 1997-04-10 1998-06-23 The Perkin-Elmer Corporation Substituted propargylethoxyamido nucleosides, oligonucleotides and methods for using same
US6130101A (en) * 1997-09-23 2000-10-10 Molecular Probes, Inc. Sulfonated xanthene derivatives
US6008379A (en) 1997-10-01 1999-12-28 The Perkin-Elmer Corporation Aromatic-substituted xanthene dyes
US6221604B1 (en) * 2000-02-07 2001-04-24 Pe Corporation Electron-deficient nitrogen heterocycle-substituted fluorescein dyes

Also Published As

Publication number Publication date
WO2001057264A3 (en) 2002-02-21
EP1196640B1 (en) 2004-02-04
ATE258992T1 (en) 2004-02-15
JP2006257427A (en) 2006-09-28
ES2211768T3 (en) 2004-07-16
USRE39663E1 (en) 2007-05-29
JP2007277565A (en) 2007-10-25
JP2007277564A (en) 2007-10-25
US6221604B1 (en) 2001-04-24
JP2003521571A (en) 2003-07-15
WO2001057264A2 (en) 2001-08-09
EP1196640A2 (en) 2002-04-17
CA2368495C (en) 2009-09-29
DE60101939D1 (en) 2004-03-11
JP4942150B2 (en) 2012-05-30
DE60101939T2 (en) 2005-01-05
AU772739B2 (en) 2004-05-06
JP2006070270A (en) 2006-03-16
AU3483901A (en) 2001-08-14

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Effective date: 20210205