CN101454315B - 用于合成罗丹明-标记的寡核苷酸的试剂 - Google Patents

用于合成罗丹明-标记的寡核苷酸的试剂 Download PDF

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Publication number
CN101454315B
CN101454315B CN200780019599.1A CN200780019599A CN101454315B CN 101454315 B CN101454315 B CN 101454315B CN 200780019599 A CN200780019599 A CN 200780019599A CN 101454315 B CN101454315 B CN 101454315B
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group
protected
moiety
reagent
rhodamine
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Expired - Fee Related
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Chinese (zh)
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CN101454315A (zh
Inventor
斯科特·C·本森
瑞明·N·邹
克利须那·G·优波达亚
保罗·M·肯尼
乔纳森·M·卡塞尔
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Applied Biosystems Inc
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Applied Biosystems Inc
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/96—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings spiro-condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/22—Amides of acids of phosphorus
    • C07F9/24—Esteramides
    • C07F9/2404—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/2408—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic of hydroxyalkyl compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/22—Amides of acids of phosphorus
    • C07F9/24—Esteramides
    • C07F9/2404—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/242—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic of hydroxyaryl compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
    • C07F9/6509—Six-membered rings
    • C07F9/650952—Six-membered rings having the nitrogen atoms in the positions 1 and 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6527—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07F9/653—Five-membered rings
    • C07F9/65306—Five-membered rings containing two nitrogen atoms
    • C07F9/65312—Five-membered rings containing two nitrogen atoms having the two nitrogen atoms in positions 1 and 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
    • C07F9/65515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • 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
    • C07H21/04—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids with deoxyribosyl as saccharide radical
    • 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
    • C09B11/10—Amino derivatives of triarylmethanes
    • C09B11/24—Phthaleins containing amino groups ; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Biotechnology (AREA)
  • Engineering & Computer Science (AREA)
  • Saccharide Compounds (AREA)
  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Investigating Or Analysing Biological Materials (AREA)
CN200780019599.1A 2006-03-31 2007-04-02 用于合成罗丹明-标记的寡核苷酸的试剂 Expired - Fee Related CN101454315B (zh)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US78777706P 2006-03-31 2006-03-31
US60/787,777 2006-03-31
PCT/US2007/065798 WO2007115265A2 (en) 2006-03-31 2007-04-02 Reagents useful for synthesizing rhodamine-labeled oligonucleotides

Publications (2)

Publication Number Publication Date
CN101454315A CN101454315A (zh) 2009-06-10
CN101454315B true CN101454315B (zh) 2016-08-17

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Country Status (7)

Country Link
US (5) US9040674B2 (https=)
EP (1) EP2001871B1 (https=)
JP (3) JP2009533022A (https=)
CN (1) CN101454315B (https=)
AU (1) AU2007234451A1 (https=)
CA (1) CA2647827A1 (https=)
WO (1) WO2007115265A2 (https=)

Families Citing this family (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2572826C2 (ru) 2008-12-02 2016-01-20 Чиралджен, Лтд. Способ синтеза модифицированных по атому фосфора нуклеиновых кислот
CA2767253A1 (en) 2009-07-06 2011-01-13 Ontorii, Inc. Novel nucleic acid prodrugs and methods of use thereof
JP5868324B2 (ja) 2010-09-24 2016-02-24 株式会社Wave Life Sciences Japan 不斉補助基
CN107326073A (zh) * 2010-12-29 2017-11-07 生命技术公司 作为荧光参考标准品的 ddao 化合物
AU2012284265B2 (en) 2011-07-19 2017-08-17 Wave Life Sciences Ltd. Methods for the synthesis of functionalized nucleic acids
WO2013134686A1 (en) * 2012-03-09 2013-09-12 Promega Corporation pH SENSORS
JP6453212B2 (ja) 2012-07-13 2019-01-16 ウェイブ ライフ サイエンシズ リミテッドＷａｖｅ Ｌｉｆｅ Ｓｃｉｅｎｃｅｓ Ｌｔｄ． キラル制御
SG11201500239VA (en) 2012-07-13 2015-03-30 Wave Life Sciences Japan Asymmetric auxiliary group
CN104684923B (zh) 2012-07-13 2018-09-28 株式会社新日本科学 手性核酸佐剂
CN103122379A (zh) * 2012-12-24 2013-05-29 深圳先进技术研究院 基因转染实时监测的方法
CN103232489B (zh) * 2013-02-18 2016-09-28 常州津坛生物科技有限公司 一种荧光探针化合物及其制备方法和用途
CA2902992C (en) * 2013-03-08 2020-08-25 Illumina Cambridge Ltd Rhodamine compounds and their use as fluorescent labels
WO2015108047A1 (ja) 2014-01-15 2015-07-23 株式会社新日本科学 免疫誘導活性を有するキラル核酸アジュバンド及び免疫誘導活性剤
JPWO2015108046A1 (ja) 2014-01-15 2017-03-23 株式会社新日本科学 抗アレルギー作用を有するキラル核酸アジュバンド及び抗アレルギー剤
WO2015108048A1 (ja) 2014-01-15 2015-07-23 株式会社新日本科学 抗腫瘍作用を有するキラル核酸アジュバンド及び抗腫瘍剤
ES2917473T3 (es) 2014-01-16 2022-07-08 Wave Life Sciences Ltd Diseño quiral
CN106281309B (zh) * 2016-08-03 2018-07-10 陕西师范大学 硼酸衍生物功能化荧光探针在检测5-羟甲基胞嘧啶中的应用
CN106350064B (zh) * 2016-08-30 2019-03-29 上海大学 利用微波加热法水热炭化造纸黑液制备水溶性荧光碳材料的方法
CA3099701A1 (en) * 2018-05-07 2019-11-14 Cepheid Sulforhodamine phosphoramidite dyes
EP3833715B1 (en) 2018-08-10 2026-01-07 Life Technologies Corporation Silicon-substituted rhodamine dyes and dye conjugates
SG11202106124UA (en) * 2018-12-20 2021-07-29 Life Technologies Corp Modified rhodamine dye and use thereof in biological assays
KR20230034333A (ko) 2020-07-02 2023-03-09 라이프 테크놀로지스 코포레이션 트리뉴클레오티드 캡 유사체, 제조 및 이의 용도
WO2022020731A2 (en) 2020-07-23 2022-01-27 Life Technologies Corporation Compositions, systems and methods for biological analysis involving energy transfer dye conjugates and analytes comprising the same
CA3186955A1 (en) 2020-07-23 2022-01-27 Scott Benson Energy transfer dye conjugates for use in biological assays
US20250092261A1 (en) 2021-07-21 2025-03-20 Life Technologies Corporation Dibenzoxanthene Quenchers, Uses, and Methods of Preparation
CN116333006A (zh) * 2023-04-07 2023-06-27 苏州欧利生物医药科技有限公司 一种带有荧光标记物的寡核苷酸的固相合成方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5942610A (en) * 1989-08-28 1999-08-24 Clontech Laboratories, Inc. Non-nucleoside 1,3-diol reagents and their use to label or modify synthetic oligonucleotides
WO2000058406A1 (en) * 1999-03-27 2000-10-05 Pe Corporation (Ny) 4,7-dichlororhodamine dyes useful as molecular probes
WO2006020947A2 (en) * 2004-08-13 2006-02-23 Epoch Biosciences, Inc. Phosphonate fluorescent dyes and conjugates

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4557862A (en) 1983-10-28 1985-12-10 University Patents, Inc. Rhodamine derivatives as fluorogenic substrates for proteinases
US5231191A (en) 1987-12-24 1993-07-27 Applied Biosystems, Inc. Rhodamine phosphoramidite compounds
US4965349A (en) 1987-12-24 1990-10-23 Applied Biosystems, Inc. Method of synthesizing oligonucleotides labeled with ammonia-labile groups on solid phase supports
US5366860A (en) * 1989-09-29 1994-11-22 Applied Biosystems, Inc. Spectrally resolvable rhodamine dyes for nucleic acid sequence determination
US6028190A (en) * 1994-02-01 2000-02-22 The Regents Of The University Of California Probes labeled with energy transfer coupled dyes
US6020481A (en) * 1996-04-01 2000-02-01 The Perkin-Elmer Corporation Asymmetric benzoxanthene dyes
US6583168B1 (en) * 1997-11-25 2003-06-24 Applera Corporation Sulfonated diarylrhodamine dyes
US6255476B1 (en) * 1999-02-22 2001-07-03 Pe Corporation (Ny) Methods and compositions for synthesis of labelled oligonucleotides and analogs on solid-supports
US6248884B1 (en) * 1999-06-03 2001-06-19 The Perkin-Elmer Corporation Extended rhodamine compounds useful as fluorescent labels
US7183405B2 (en) 1999-06-25 2007-02-27 Syn Gen, Inc. Compositions and methods for labeling oligonucleotides
US6750357B1 (en) 1999-06-25 2004-06-15 Syngen, Inc. Rhodamine-based fluorophores useful as labeling reagents
US20040014131A1 (en) * 2002-07-09 2004-01-22 Pfizer Inc. Assay methods
WO2005007678A2 (en) * 2003-07-14 2005-01-27 Irm Llc Methods for the preparation of rhodamine

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5942610A (en) * 1989-08-28 1999-08-24 Clontech Laboratories, Inc. Non-nucleoside 1,3-diol reagents and their use to label or modify synthetic oligonucleotides
WO2000058406A1 (en) * 1999-03-27 2000-10-05 Pe Corporation (Ny) 4,7-dichlororhodamine dyes useful as molecular probes
WO2006020947A2 (en) * 2004-08-13 2006-02-23 Epoch Biosciences, Inc. Phosphonate fluorescent dyes and conjugates

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Ravi Vinayak.A convenient, solid-phase coupling of rhodamine dye acids to 5’amino-oligonucleotides.《Tetrahedron Letters》.1999,第40卷(第43期),第7611-7613页. *

Also Published As

Publication number Publication date
CN101454315A (zh) 2009-06-10
JP5698206B2 (ja) 2015-04-08
WO2007115265A2 (en) 2007-10-11
US20080071070A1 (en) 2008-03-20
US20230096149A1 (en) 2023-03-30
EP2001871A2 (en) 2008-12-17
EP2001871B1 (en) 2014-07-16
WO2007115265A3 (en) 2008-01-17
US9040674B2 (en) 2015-05-26
US9783560B2 (en) 2017-10-10
CA2647827A1 (en) 2007-10-11
WO2007115265A9 (en) 2007-11-29
JP2009533022A (ja) 2009-09-17
JP2013048635A (ja) 2013-03-14
JP2014079254A (ja) 2014-05-08
US20180057516A1 (en) 2018-03-01
AU2007234451A1 (en) 2007-10-11
US20200270287A1 (en) 2020-08-27
US11407773B2 (en) 2022-08-09
EP2001871A4 (en) 2010-10-20
US20150232494A1 (en) 2015-08-20

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