AU2002250262B9 - Methods, kits and compositions of combination oligomers - Google Patents
Methods, kits and compositions of combination oligomers Download PDFInfo
- Publication number
- AU2002250262B9 AU2002250262B9 AU2002250262A AU2002250262A AU2002250262B9 AU 2002250262 B9 AU2002250262 B9 AU 2002250262B9 AU 2002250262 A AU2002250262 A AU 2002250262A AU 2002250262 A AU2002250262 A AU 2002250262A AU 2002250262 B9 AU2002250262 B9 AU 2002250262B9
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- Prior art keywords
- oligomer
- combination
- linker
- amino acid
- gly
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- IKAIKUBBJHFNBZ-LURJTMIESA-N Gly-Lys Chemical compound NCCCC[C@@H](C(O)=O)NC(=O)CN IKAIKUBBJHFNBZ-LURJTMIESA-N 0.000 claims description 7
- ZUKPVRWZDMRIEO-VKHMYHEASA-N L-cysteinylglycine Chemical compound SC[C@H]([NH3+])C(=O)NCC([O-])=O ZUKPVRWZDMRIEO-VKHMYHEASA-N 0.000 claims description 7
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- 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
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- C—CHEMISTRY; METALLURGY
- C40—COMBINATORIAL TECHNOLOGY
- C40B—COMBINATORIAL CHEMISTRY; LIBRARIES, e.g. CHEMICAL LIBRARIES
- C40B20/00—Methods specially adapted for identifying library members
- C40B20/04—Identifying library members by means of a tag, label, or other readable or detectable entity associated with the library members, e.g. decoding processes
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- C—CHEMISTRY; METALLURGY
- C40—COMBINATORIAL TECHNOLOGY
- C40B—COMBINATORIAL CHEMISTRY; LIBRARIES, e.g. CHEMICAL LIBRARIES
- C40B30/00—Methods of screening libraries
- C40B30/04—Methods of screening libraries by measuring the ability to specifically bind a target molecule, e.g. antibody-antigen binding, receptor-ligand binding
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- C—CHEMISTRY; METALLURGY
- C40—COMBINATORIAL TECHNOLOGY
- C40B—COMBINATORIAL CHEMISTRY; LIBRARIES, e.g. CHEMICAL LIBRARIES
- C40B40/00—Libraries per se, e.g. arrays, mixtures
- C40B40/04—Libraries containing only organic compounds
- C40B40/06—Libraries containing nucleotides or polynucleotides, or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/11—Compounds covalently bound to a solid support
-
- C—CHEMISTRY; METALLURGY
- C40—COMBINATORIAL TECHNOLOGY
- C40B—COMBINATORIAL CHEMISTRY; LIBRARIES, e.g. CHEMICAL LIBRARIES
- C40B40/00—Libraries per se, e.g. arrays, mixtures
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- 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
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/81—Packaged device or kit
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| AU2007200335A AU2007200335B2 (en) | 2001-03-09 | 2007-01-25 | Methods, kits and compositions pertaining to combination oligomers and libraries for their preparation |
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| US7256275B2 (en) * | 2001-03-09 | 2007-08-14 | Boston Probes, Inc. | Methods, kits and compositions pertaining to combination oligomers and libraries for their preparation |
| DE60330182D1 (de) | 2002-09-08 | 2009-12-31 | Applera Corp | Festphasengebundene PNA-Dimere und deren Synthese |
| EP1594984A2 (en) * | 2003-02-18 | 2005-11-16 | Applera Corporation | Compositions and methods for multiplex analysis of polynucleotides |
| EP1674581A1 (en) * | 2004-12-21 | 2006-06-28 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. | Twin probes, a tool for the detection of SNPs |
| US7892737B2 (en) * | 2005-06-30 | 2011-02-22 | Life Technologies Corporation | Compositions, kits and methods pertaining to stability modulation of PNA oligomer/nucleic acid complexes |
| GB2433591A (en) * | 2005-12-20 | 2007-06-27 | Sharp Kk | Method for functionalising a hydrophobic substrate |
| GB2433505A (en) * | 2005-12-20 | 2007-06-27 | Sharp Kk | Capture agents for binding a ligand |
| GB2433506A (en) * | 2005-12-20 | 2007-06-27 | Sharp Kk | A method of producing a multimeric capture agent |
| US9677123B2 (en) * | 2006-03-15 | 2017-06-13 | Siemens Healthcare Diagnostics Inc. | Degenerate nucleobase analogs |
| EP2031074A4 (en) * | 2006-08-08 | 2010-09-08 | Arkray Inc | METHOD FOR VARIATION DETECTION AND KIT THEREFOR |
| US20100120031A1 (en) * | 2006-09-22 | 2010-05-13 | The United States Of America, As Represented By The Secretary, Dept. Of | Synthesis of trans-tert-butyl-2-aminocyclopentylcarbamate |
| GB0718255D0 (en) * | 2007-09-19 | 2007-10-31 | Univ Edinburgh | Nucleobase characterisation |
| JP2012502911A (ja) * | 2008-09-14 | 2012-02-02 | インサイター インコーポレイテッド | ナノスケール分子合成 |
| US9506057B2 (en) | 2010-03-26 | 2016-11-29 | Integrated Dna Technologies, Inc. | Modifications for antisense compounds |
| EP2553123B1 (en) * | 2010-03-26 | 2016-08-24 | Integrated DNA Technologies, Inc. | Methods for enhancing nucleic acid hybridization |
| AU2011299233B2 (en) | 2010-09-07 | 2016-09-15 | Integrated Dna Technologies, Inc. | Modifications for antisense compounds |
| JP5852222B2 (ja) * | 2011-03-29 | 2016-02-03 | シージーン アイエヌシー | Ｐｔｏ切断及び延長−依存的切断によるターゲット核酸配列の検出 |
| CN104039961A (zh) * | 2012-01-07 | 2014-09-10 | 株式会社博纳克 | 具有氨基酸骨架的单链核酸分子 |
| EP2823061B1 (en) * | 2012-03-05 | 2018-02-14 | Seegene, Inc. | Detection of nucleotide variation on target nucleic acid sequence by pto cleavage and extension assay |
| WO2013180038A1 (ja) | 2012-05-26 | 2013-12-05 | 株式会社ボナック | デリバリー機能を有する遺伝子発現制御用の一本鎖核酸分子 |
| CN104703971B (zh) | 2012-08-02 | 2018-08-21 | 株式会社百奥尼 | 新型偶氮化合物及其利用、以及其制造方法 |
| GB201316644D0 (en) * | 2013-09-19 | 2013-11-06 | Kymab Ltd | Expression vector production & High-Throughput cell screening |
| WO2015099122A1 (ja) | 2013-12-26 | 2015-07-02 | 学校法人東京医科大学 | 遺伝子発現制御のための人工ミミックｍｉＲＮＡおよびその用途 |
| CN106068324B (zh) | 2013-12-27 | 2020-12-29 | 株式会社博纳克 | 控制基因表达的人工匹配型miRNA及其用途 |
| KR20170098914A (ko) | 2014-12-27 | 2017-08-30 | 가부시키가이샤 보낙 | 유전자 발현 제어를 위한 천연형 miRNA 및 그의 용도 |
| WO2016158809A1 (ja) | 2015-03-27 | 2016-10-06 | 株式会社ボナック | デリバリー機能と遺伝子発現制御能を有する一本鎖核酸分子 |
| JP2019508037A (ja) | 2016-02-16 | 2019-03-28 | イェール ユニバーシティーＹａｌｅ Ｕｎｉｖｅｒｓｉｔ | 標的化遺伝子編集を増強するための組成物およびその使用方法 |
| WO2018187493A1 (en) | 2017-04-04 | 2018-10-11 | Yale University | Compositions and methods for in utero delivery |
| KR102403904B1 (ko) * | 2019-12-24 | 2022-06-02 | 주식회사 시선바이오머티리얼스 | 용액공정상 pna 올리고머의 제조방법 |
| JP2023542867A (ja) * | 2020-09-11 | 2023-10-12 | グリンプス バイオ， インコーポレイテッド | 疾患の検出／診断、病期分類、モニタリング及び処置のための生体外でのプロテアーゼ活性検出 |
| CN113322523B (zh) * | 2021-06-17 | 2024-03-19 | 翌圣生物科技(上海)股份有限公司 | Rna快速建库方法及其应用 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999021881A1 (en) * | 1997-10-27 | 1999-05-06 | Boston Probes, Inc. | Methods, kits and compositions pertaining to linear beacons |
Family Cites Families (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4683202A (en) | 1985-03-28 | 1987-07-28 | Cetus Corporation | Process for amplifying nucleic acid sequences |
| CA1284931C (en) | 1986-03-13 | 1991-06-18 | Henry A. Erlich | Process for detecting specific nucleotide variations and genetic polymorphisms present in nucleic acids |
| US5252293A (en) | 1989-01-17 | 1993-10-12 | Vladimir Drbal | Analytical slide with porous filter membrane |
| DE3943522A1 (de) * | 1989-07-26 | 1991-02-07 | Boehringer Mannheim Gmbh | Heterobifunktionelle verbindungen |
| US5366860A (en) | 1989-09-29 | 1994-11-22 | Applied Biosystems, Inc. | Spectrally resolvable rhodamine dyes for nucleic acid sequence determination |
| US5188934A (en) | 1989-11-14 | 1993-02-23 | Applied Biosystems, Inc. | 4,7-dichlorofluorescein dyes as molecular probes |
| US5714331A (en) | 1991-05-24 | 1998-02-03 | Buchardt, Deceased; Ole | Peptide nucleic acids having enhanced binding affinity, sequence specificity and solubility |
| US6451968B1 (en) | 1991-05-24 | 2002-09-17 | Isis Pharmaceuticals, Inc. | Peptide nucleic acids |
| US5766855A (en) | 1991-05-24 | 1998-06-16 | Buchardt, Deceased; Ole | Peptide nucleic acids having enhanced binding affinity and sequence specificity |
| US5641625A (en) | 1992-05-22 | 1997-06-24 | Isis Pharmaceuticals, Inc. | Cleaving double-stranded DNA with peptide nucleic acids |
| US5719262A (en) | 1993-11-22 | 1998-02-17 | Buchardt, Deceased; Ole | Peptide nucleic acids having amino acid side chains |
| US5539082A (en) | 1993-04-26 | 1996-07-23 | Nielsen; Peter E. | Peptide nucleic acids |
| DK51092D0 (da) * | 1991-05-24 | 1992-04-15 | Ole Buchardt | Oligonucleotid-analoge betegnet pna, monomere synthoner og fremgangsmaade til fremstilling deraf samt anvendelser deraf |
| US5700922A (en) | 1991-12-24 | 1997-12-23 | Isis Pharmaceuticals, Inc. | PNA-DNA-PNA chimeric macromolecules |
| GB9211979D0 (en) | 1992-06-05 | 1992-07-15 | Buchard Ole | Uses of nucleic acid analogues |
| US5527675A (en) | 1993-08-20 | 1996-06-18 | Millipore Corporation | Method for degradation and sequencing of polymers which sequentially eliminate terminal residues |
| DE4331012A1 (de) | 1993-09-13 | 1995-03-16 | Bayer Ag | Nukleinsäuren-bindende Oligomere mit N-Verzweigung für Therapie und Diagnostik |
| GB2284209A (en) | 1993-11-25 | 1995-05-31 | Ole Buchardt | Nucleic acid analogue-induced transcription of RNA from a double-stranded DNA template |
| GB2289677A (en) | 1993-12-06 | 1995-11-29 | Pna Diagnostics As | Labelling of nucleic acid analogue-peptide chimerae |
| DK145493D0 (da) | 1993-12-23 | 1993-12-23 | Dako As | Antistof |
| US5539083A (en) | 1994-02-23 | 1996-07-23 | Isis Pharmaceuticals, Inc. | Peptide nucleic acid combinatorial libraries and improved methods of synthesis |
| US5705333A (en) | 1994-08-05 | 1998-01-06 | The Regents Of The University Of California | Peptide-based nucleic acid mimics(PENAMS) |
| US6280964B1 (en) | 1995-04-14 | 2001-08-28 | The Regents Of The University Of California | Binding sites for phosphotyrosine binding domains |
| DE69632324T2 (de) | 1995-06-07 | 2005-06-16 | PerSeptive Biosystems, Inc., Framingham | Pna-dna-chimäre und pna-synthone zu deren herstellung |
| DE19532553A1 (de) | 1995-09-04 | 1997-03-06 | Hoechst Ag | Verfahren zur Herstellung substituierter N-Ethyl-Glycinderivate |
| US6020481A (en) | 1996-04-01 | 2000-02-01 | The Perkin-Elmer Corporation | Asymmetric benzoxanthene dyes |
| US5847162A (en) | 1996-06-27 | 1998-12-08 | The Perkin Elmer Corporation | 4, 7-Dichlororhodamine dyes |
| SE506700C2 (sv) | 1996-05-31 | 1998-02-02 | Mikael Kubista | Sond och förfaranden för analys av nukleinsyra |
| US6110676A (en) | 1996-12-04 | 2000-08-29 | Boston Probes, Inc. | Methods for suppressing the binding of detectable probes to non-target sequences in hybridization assays |
| CA2218440A1 (en) | 1996-12-21 | 1998-06-21 | Boehringer Mannheim Gmbh | Method of analysis using signal amplification |
| EP0857791B1 (en) * | 1996-12-21 | 2004-03-31 | PNA Diagnostics A/S | Method of analysis using signal amplification |
| US6080418A (en) | 1997-04-07 | 2000-06-27 | 3M Innovative Properties Company | Suspensions of microcapsules containing biologically active ingredients and adhesive microspheres |
| US6107470A (en) | 1997-05-29 | 2000-08-22 | Nielsen; Peter E. | Histidine-containing peptide nucleic acids |
| AU745094B2 (en) | 1997-06-13 | 2002-03-14 | Gryphon Sciences | Solid phase native chemical ligation of unprotected or N-terminal cysteine protected peptides in aqueous solution |
| EP0897991B1 (en) | 1997-08-22 | 2004-12-08 | PNA Diagnostics ApS | Small Triplex Forming PNA Oligos |
| US6008379A (en) | 1997-10-01 | 1999-12-28 | The Perkin-Elmer Corporation | Aromatic-substituted xanthene dyes |
| ATE478090T1 (de) | 1997-10-27 | 2010-09-15 | Boston Probes Inc | SICH AUF ßPNA MOLECULAR BEACONSß BEZIEHENDE VERFAHREN, TESTSÄTZE UND ZUSAMMENSETZUNGEN |
| US5936087A (en) | 1997-11-25 | 1999-08-10 | The Perkin-Elmer Corporation | Dibenzorhodamine dyes |
| US6080868A (en) | 1998-01-23 | 2000-06-27 | The Perkin-Elmer Corporation | Nitro-substituted non-fluorescent asymmetric cyanine dye compounds |
| US6326479B1 (en) | 1998-01-27 | 2001-12-04 | Boston Probes, Inc. | Synthetic polymers and methods, kits or compositions for modulating the solubility of same |
| CA2320390C (en) | 1998-02-11 | 2010-06-08 | Applied Biosystems, Llc | Pna and dna conjugates and methods for preparation thereof |
| WO1999049293A2 (en) | 1998-03-24 | 1999-09-30 | Boston Probes, Inc. | Methods, kits and compositions pertaining to detection complexes |
| DE69941690D1 (de) | 1998-04-29 | 2010-01-07 | Boston Probes Inc | Methoden, testsätze und kompositionen zur detektion und quantifizierung von zielsequenzen |
| US6287772B1 (en) | 1998-04-29 | 2001-09-11 | Boston Probes, Inc. | Methods, kits and compositions for detecting and quantitating target sequences |
| AU4965499A (en) | 1998-07-09 | 2000-02-01 | Biocept, Inc. | Method of using an improved peptide nucleic acid universal library to optimize dna sequence hybridation |
| US6248884B1 (en) | 1999-06-03 | 2001-06-19 | The Perkin-Elmer Corporation | Extended rhodamine compounds useful as fluorescent labels |
| US6316230B1 (en) | 1999-08-13 | 2001-11-13 | Applera Corporation | Polymerase extension at 3′ terminus of PNA-DNA chimera |
| US6140500A (en) | 1999-09-03 | 2000-10-31 | Pe Corporation | Red-emitting [8,9]benzophenoxazine nucleic acid dyes and methods for their use |
| US6297016B1 (en) * | 1999-10-08 | 2001-10-02 | Applera Corporation | Template-dependent ligation with PNA-DNA chimeric probes |
| US6472153B1 (en) | 1999-10-26 | 2002-10-29 | Epoch Biosciences, Inc. | Hybridization-triggered fluorescent detection of nucleic acids |
| US6191278B1 (en) | 1999-11-03 | 2001-02-20 | Pe Corporation | Water-soluble rhodamine dyes and conjugates thereof |
| US7256275B2 (en) * | 2001-03-09 | 2007-08-14 | Boston Probes, Inc. | Methods, kits and compositions pertaining to combination oligomers and libraries for their preparation |
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2002
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- 2002-03-09 AT AT06023675T patent/ATE496139T1/de not_active IP Right Cessation
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- 2002-03-09 EP EP06023675A patent/EP1748078B1/en not_active Expired - Lifetime
- 2002-03-09 AT AT02719163T patent/ATE346950T1/de not_active IP Right Cessation
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999021881A1 (en) * | 1997-10-27 | 1999-05-06 | Boston Probes, Inc. | Methods, kits and compositions pertaining to linear beacons |
Non-Patent Citations (3)
| Title |
|---|
| Bioorganic and Medicinal Chemistry Letters (1998) 8(6): 663-668, van der Laan et al, 17 March 1998 * |
| Nucleic Acids Research (1995) 23(2): 217-222, Egholm et al, 1995. * |
| Nucleic Acids Research (1996) 24(3): 494-500, Knudsen et al, 1996. * |
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