CA2506797C - Detectable labeled nucleoside analogs and methods of use thereof - Google Patents

Detectable labeled nucleoside analogs and methods of use thereof Download PDF

Info

Publication number
CA2506797C
CA2506797C CA002506797A CA2506797A CA2506797C CA 2506797 C CA2506797 C CA 2506797C CA 002506797 A CA002506797 A CA 002506797A CA 2506797 A CA2506797 A CA 2506797A CA 2506797 C CA2506797 C CA 2506797C
Authority
CA
Canada
Prior art keywords
compound
formula
reaction mixture
metal
oligonucleotide
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.)
Expired - Lifetime
Application number
CA002506797A
Other languages
English (en)
French (fr)
Other versions
CA2506797A1 (en
Inventor
Veeraiah Bodepudi
Amar Gupta
Stephen Will
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
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 F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of CA2506797A1 publication Critical patent/CA2506797A1/en
Application granted granted Critical
Publication of CA2506797C publication Critical patent/CA2506797C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H21/00Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/052Imidazole radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06Pyrimidine radicals
    • C07H19/067Pyrimidine radicals with ribosyl as the saccharide radical
    • 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
    • C12Q1/34Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving hydrolase
    • GPHYSICS
    • G01MEASURING; TESTING
    • G01NINVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/53Immunoassay; Biospecific binding assay; Materials therefor
    • G01N33/531Production of immunochemical test materials
    • G01N33/532Production of labelled immunochemicals
    • G01N33/533Production of labelled immunochemicals with fluorescent label
CA002506797A 2002-11-22 2003-11-20 Detectable labeled nucleoside analogs and methods of use thereof Expired - Lifetime CA2506797C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US42848402P 2002-11-22 2002-11-22
US60/428,484 2002-11-22
PCT/EP2003/013014 WO2004048397A2 (en) 2002-11-22 2003-11-20 Detectable labeled nucleoside analogs and methods of use thereof

Publications (2)

Publication Number Publication Date
CA2506797A1 CA2506797A1 (en) 2004-06-10
CA2506797C true CA2506797C (en) 2009-02-10

Family

ID=32393412

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002506797A Expired - Lifetime CA2506797C (en) 2002-11-22 2003-11-20 Detectable labeled nucleoside analogs and methods of use thereof

Country Status (6)

Country Link
US (3) US7220847B2 (US07220847-20070522-C00086.png)
EP (1) EP1565480B1 (US07220847-20070522-C00086.png)
JP (1) JP4898119B2 (US07220847-20070522-C00086.png)
AU (1) AU2003294716A1 (US07220847-20070522-C00086.png)
CA (1) CA2506797C (US07220847-20070522-C00086.png)
WO (1) WO2004048397A2 (US07220847-20070522-C00086.png)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1725572B1 (de) * 2003-11-05 2017-05-31 AGCT GmbH Makromolekulare nukleotidverbindungen und methoden zu deren anwendung
US20050147965A1 (en) * 2003-12-31 2005-07-07 Zhong Zhandong D. Compositions and methods for detecting reverse transcriptase in a sample
US7745125B2 (en) 2004-06-28 2010-06-29 Roche Molecular Systems, Inc. 2′-terminator related pyrophosphorolysis activated polymerization
WO2006048262A2 (en) * 2004-11-04 2006-05-11 Roche Diagnostics Gmbh Classification of acute myeloid leukemia
US9035035B2 (en) * 2004-11-05 2015-05-19 Genovoxx Gmbh Macromolecular nucleotide compounds and methods for using the same
EP1908848B1 (en) * 2005-05-17 2013-04-17 Sumitomo Bakelite Company, Ltd. Method for detection of gene
US7919242B2 (en) 2005-06-30 2011-04-05 Roche Molecular Systems, Inc. Light emission modifiers and their uses in nucleic acid detection, amplification and analysis
GB0517097D0 (en) 2005-08-19 2005-09-28 Solexa Ltd Modified nucleosides and nucleotides and uses thereof
WO2009100382A1 (en) * 2008-02-07 2009-08-13 Pacific Biosciences Of California, Inc. Cis reactive oxygen quenchers integrated into linkers
WO2009105258A1 (en) 2008-02-22 2009-08-27 Nektar Therapeutics Al, Corporation Oligomer conjugates of heteropentacyclic nucleosides
JP5850746B2 (ja) * 2008-11-17 2016-02-03 ヘッドウェイ テクノロジーズ, インク.Headway Technologies, Inc. 連結分子を用いた標的分子の粒子ベースの検出における方法および組成物
JP5744743B2 (ja) * 2008-11-17 2015-07-08 ヘッドウェイ テクノロジーズ, インク.Headway Technologies, Inc. 共有結合形成反応ペアを用いた標的分子の粒子ベースの検出における方法および組成物
US9092965B2 (en) 2010-08-10 2015-07-28 Christopher Thomas Lyons System and method of detecting sleep disorders
WO2012112563A2 (en) * 2011-02-16 2012-08-23 Magic Technologies, Inc. Methods and compositions for the target-localized anchoring of detectable label
FR3020071B1 (fr) 2014-04-17 2017-12-22 Dna Script Procede de synthese d'acides nucleiques, notamment d'acides nucleiques de grande longueur, utilisation du procede et kit pour la mise en œuvre du procede
FR3025201B1 (fr) * 2014-09-02 2018-10-12 Dna Script Nucleotides modifies pour la synthese d'acides nucleiques, un kit renfermant de tels nucleotides et leur utilisation pour la production de genes ou sequences d'acides nucleiques synthetiques
US11384376B2 (en) 2018-05-31 2022-07-12 Roche Molecular Systems, Inc. Reagents and methods for post-synthetic modification of nucleic acids

Family Cites Families (73)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1167387A (en) * 1913-11-01 1916-01-11 Percy Gordon Eckersley Daniel Golf-club and the like.
US1683916A (en) * 1922-12-18 1928-09-11 Rca Corp Interference-reducing means for radio receiving apparatus
US1780625A (en) * 1924-04-17 1930-11-04 Crawford Mcgregor & Canby Co Golf-club head
US1972091A (en) * 1931-06-10 1934-09-04 Du Pont Cellulose derivative composition
US2750194A (en) * 1955-01-24 1956-06-12 Austin N Clark Golf club head with weight adjustment
US3975023A (en) * 1971-12-13 1976-08-17 Kyoto Ceramic Co., Ltd. Golf club head with ceramic face plate
US3897066A (en) * 1973-11-28 1975-07-29 Peter A Belmont Golf club heads and process
US3989248A (en) * 1974-12-26 1976-11-02 Pepsico, Inc. Golf club having insert capable of elastic flexing
US4021047A (en) * 1976-02-25 1977-05-03 Mader Robert J Golf driver club
US4398965A (en) * 1976-10-26 1983-08-16 Pepsico, Inc. Method of making iron golf clubs with flexible impact surface
JPS5985677A (ja) * 1982-10-19 1984-05-17 住友ゴム工業株式会社 ウツドクラブのヘツド
FI79124C (fi) * 1986-05-28 1989-11-10 Neste Oy Modifierad polyolefin.
US4872685A (en) * 1988-11-14 1989-10-10 Sun Donald J C Golf club head with impact insert member
USD318087S (en) * 1989-02-10 1991-07-09 Callaway Golf Company Golf driver head
FR2647685A1 (fr) * 1989-06-01 1990-12-07 Salomon Sa Tete de club de golf et procede de fabrication de celle-ci
US5344140A (en) * 1989-06-12 1994-09-06 Donald A. Anderson Golf club head and method of forming same
FR2657531A1 (fr) * 1990-01-31 1991-08-02 Salomon Sa Tete de club de golf.
US5210051A (en) * 1990-03-27 1993-05-11 Cree Research, Inc. High efficiency light emitting diodes from bipolar gallium nitride
US5210015A (en) 1990-08-06 1993-05-11 Hoffman-La Roche Inc. Homogeneous assay system using the nuclease activity of a nucleic acid polymerase
USD340492S (en) * 1990-09-17 1993-10-19 Odyssey Sports, Inc. Golf driver head
US5067715A (en) * 1990-10-16 1991-11-26 Callaway Golf Company Hollow, metallic golf club head with dendritic structure
US5193811A (en) * 1990-11-09 1993-03-16 The Yokohama Rubber Co., Ltd. Wood type golf club head
JPH04197276A (ja) * 1990-11-29 1992-07-16 Maruman Golf Corp ゴルフのウッドクラブヘッド
US5994056A (en) 1991-05-02 1999-11-30 Roche Molecular Systems, Inc. Homogeneous methods for nucleic acid amplification and detection
FR2678843A1 (fr) * 1991-07-11 1993-01-15 Taylor Made Golf Co Tete de club de golf.
US5306450A (en) * 1991-08-13 1994-04-26 The Yokohama Rubber Co., Ltd. Method of producing wood type golf club head
USD344117S (en) * 1991-11-26 1994-02-08 Callaway Golf Company Golf club head
USD343434S (en) * 1992-01-13 1994-01-18 Callaway Golf Company Golf club head
JP2521221Y2 (ja) * 1992-02-27 1996-12-25 ダイワゴルフ株式会社 ゴルフクラブヘッド
FR2689407A1 (fr) * 1992-04-01 1993-10-08 Taylor Made Golf Co Tête de club de golf composée d'un corps creux plastique et d'un élément d'obturation.
FR2689406B1 (fr) * 1992-04-01 1994-06-03 Taylor Made Golf Co Tete de club de golf composee d'un sous-ensemble interne et d'une enveloppe externe.
FR2695836A1 (fr) * 1992-09-18 1994-03-25 Taylor Made Golf Co Procédé de fabrication d'une tête de club de golf comprenant des masselottes d'inertie.
US5288344A (en) * 1993-04-07 1994-02-22 California Institute Of Technology Berylllium bearing amorphous metallic alloys formed by low cooling rates
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
US5410798A (en) * 1994-01-06 1995-05-02 Lo; Kun-Nan Method for producing a composite golf club head
USD364906S (en) * 1994-07-11 1995-12-05 Callaway Golf Company Golf club head
US5491063A (en) 1994-09-01 1996-02-13 Hoffmann-La Roche Inc. Methods for in-solution quenching of fluorescently labeled oligonucleotide probes
US5499814A (en) * 1994-09-08 1996-03-19 Lu; Clive S. Hollow club head with deflecting insert face plate
USD377674S (en) * 1995-01-13 1997-01-28 Callaway Golf Company Golf club head
US5618359A (en) * 1995-02-08 1997-04-08 California Institute Of Technology Metallic glass alloys of Zr, Ti, Cu and Ni
US5843655A (en) 1995-09-18 1998-12-01 Affymetrix, Inc. Methods for testing oligonucleotide arrays
US20010018514A1 (en) * 1998-07-31 2001-08-30 Mcgall Glenn H. Nucleic acid labeling compounds
US5863261A (en) * 1996-03-27 1999-01-26 Demarini Sports, Inc. Golf club head with elastically deforming face and back plates
US5896642A (en) * 1996-07-17 1999-04-27 Amorphous Technologies International Die-formed amorphous metallic articles and their fabrication
US5776011A (en) * 1996-09-27 1998-07-07 Echelon Golf Golf club head
US5797443A (en) * 1996-09-30 1998-08-25 Amorphous Technologies International Method of casting articles of a bulk-solidifying amorphous alloy
US5830084A (en) * 1996-10-23 1998-11-03 Callaway Golf Company Contoured golf club face
US5743813A (en) * 1997-02-19 1998-04-28 Chien Ting Precision Casting Co., Ltd. Golf club head
US5888148A (en) * 1997-05-19 1999-03-30 Vardon Golf Company, Inc. Golf club head with power shaft and method of making
US6406381B2 (en) * 1997-10-23 2002-06-18 Callaway Golf Company Composite golf club head and method of manufacturing
US6248025B1 (en) * 1997-10-23 2001-06-19 Callaway Golf Company Composite golf club head and method of manufacturing
US6386990B1 (en) * 1997-10-23 2002-05-14 Callaway Golf Company Composite golf club head with integral weight strip
US6021840A (en) * 1998-01-23 2000-02-08 Howmet Research Corporation Vacuum die casting of amorphous alloys
JPH11280512A (ja) * 1998-03-30 1999-10-12 Nissan Motor Co Ltd ハイブリッド車両
US6152833A (en) * 1998-06-15 2000-11-28 Frank D. Werner Large face golf club construction
US6149534A (en) * 1998-11-02 2000-11-21 Taylor Made Golf Company, Inc. Bi-metallic golf club head with single plane interface
US6332848B1 (en) * 1999-01-28 2001-12-25 Cobra Golf Incorporated Metal wood golf club head
US6165081A (en) * 1999-02-24 2000-12-26 Chou; Pei Chi Golf club head for controlling launch velocity of a ball
US6310081B1 (en) * 1999-05-10 2001-10-30 American Home Products Corporation Biphenyl sulfonyl aryl carboxylic acids useful in the treatment of insulin resistance and hyperglycemia
AU7019200A (en) * 1999-08-31 2001-03-26 Nycomed Amersham Plc Nucleoside analogues
US6491592B2 (en) * 1999-11-01 2002-12-10 Callaway Golf Company Multiple material golf club head
US6390933B1 (en) * 1999-11-01 2002-05-21 Callaway Golf Company High cofficient of restitution golf club head
US6565452B2 (en) * 1999-11-01 2003-05-20 Callaway Golf Company Multiple material golf club head with face insert
US6354962B1 (en) * 1999-11-01 2002-03-12 Callaway Golf Company Golf club head with a face composed of a forged material
US6368234B1 (en) * 1999-11-01 2002-04-09 Callaway Golf Company Golf club striking plate having elliptical regions of thickness
US6383092B1 (en) * 1999-11-18 2002-05-07 Callaway Golf Company Golf ball with pyramidal protrusions
USD445863S1 (en) * 2000-01-24 2001-07-31 Callaway Golf Company Golf club head
USD441819S1 (en) * 2000-08-04 2001-05-08 Callaway Golf Company Golf club head
USD444196S1 (en) * 2000-08-04 2001-06-26 Callaway Golf Company Golf club sole plate
USD457209S1 (en) * 2001-07-12 2002-05-14 Callaway Golf Company Golf club head
USD471244S1 (en) * 2002-02-21 2003-03-04 Callaway Golf Company Golf club head
USD472593S1 (en) * 2002-03-27 2003-04-01 Callaway Golf Company Golf club head
USD481774S1 (en) * 2003-05-29 2003-11-04 Callaway Golf Company Golf club head

Also Published As

Publication number Publication date
US7456266B2 (en) 2008-11-25
JP4898119B2 (ja) 2012-03-14
US20040171040A1 (en) 2004-09-02
AU2003294716A1 (en) 2004-06-18
CA2506797A1 (en) 2004-06-10
US7501504B2 (en) 2009-03-10
JP2006510623A (ja) 2006-03-30
WO2004048397A2 (en) 2004-06-10
WO2004048397A3 (en) 2004-07-01
EP1565480B1 (en) 2018-08-22
US20070208169A1 (en) 2007-09-06
EP1565480A2 (en) 2005-08-24
US7220847B2 (en) 2007-05-22
AU2003294716A8 (en) 2004-06-18
US20070202576A1 (en) 2007-08-30

Similar Documents

Publication Publication Date Title
US7456266B2 (en) Detectable labeled nucleoside analogs and methods of use thereof
US6117986A (en) Pyrimidines linked to a quencher
JP2966524B2 (ja) 赤外染料で標識されたヌクレオチド及び核酸検出におけるそれらの使用
US7223541B2 (en) Terminal-phosphate-labeled nucleotides and methods of use
US7041812B2 (en) Labeled nucleoside polyphosphates
US5998593A (en) Fluorescent enzyme substrates
EP0608737B1 (de) Sulfocumarinhaltige Nukleotide und deren Verwendung in Nachweisverfahren für Nukleinsäuren
CA2774344A1 (en) Terminal-phosphate-labeled nucleotides and methods of use
NO832292L (no) Modifiserte merkede nukleotider og polynukleotider samt deres fremstilling, anvendelse og paavisning
US20080038745A1 (en) Nucleotide analogs with six-membered rings
JPH07184696A (ja) 核酸固定化方法
CN109790196A (zh) 可逆封闭的核苷类似物及其用途
JP2540482B2 (ja) ポリヌクレオチド配列の生体内標識化
US7452674B1 (en) Detectable labeled nucleoside analogs and methods of use thereof
EP1296997B1 (en) Base analogues
US20050239073A1 (en) Fluorescent entity comprising a fluorophore covalently attached to at least one oligonucleotide and comprising at least one functional group, and uses thereof
US20230050863A1 (en) Dicationic fluorescent dyes
Silverman et al. Quenched autoligation probes

Legal Events

Date Code Title Description
EEER Examination request
MKEX Expiry

Effective date: 20231120