CA2262618C - Novel boronic acid-containing nucleic acids and their use as diagnostic agents - Google Patents

Novel boronic acid-containing nucleic acids and their use as diagnostic agents Download PDF

Info

Publication number
CA2262618C
CA2262618C CA002262618A CA2262618A CA2262618C CA 2262618 C CA2262618 C CA 2262618C CA 002262618 A CA002262618 A CA 002262618A CA 2262618 A CA2262618 A CA 2262618A CA 2262618 C CA2262618 C CA 2262618C
Authority
CA
Canada
Prior art keywords
group
ester
accordance
carbon atoms
hydroxyl
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 - Fee Related
Application number
CA002262618A
Other languages
English (en)
French (fr)
Other versions
CA2262618A1 (en
Inventor
Mark L. Stolowitz
Robert J. Kaiser
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.)
Cambrex Bio Science Rockland Inc
Original Assignee
Cambrex Bio Science Rockland Inc
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 Cambrex Bio Science Rockland Inc filed Critical Cambrex Bio Science Rockland Inc
Publication of CA2262618A1 publication Critical patent/CA2262618A1/en
Application granted granted Critical
Publication of CA2262618C publication Critical patent/CA2262618C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H23/00Compounds containing boron, silicon or a metal, e.g. chelates or vitamin B12
    • 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
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12PFERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P19/00Preparation of compounds containing saccharide radicals
    • C12P19/26Preparation of nitrogen-containing carbohydrates
    • C12P19/28N-glycosides
    • C12P19/30Nucleotides
    • C12P19/34Polynucleotides, e.g. nucleic acids, oligoribonucleotides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Genetics & Genomics (AREA)
  • General Health & Medical Sciences (AREA)
  • Biotechnology (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Microbiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
  • Saccharide Compounds (AREA)
CA002262618A 1996-08-05 1997-07-31 Novel boronic acid-containing nucleic acids and their use as diagnostic agents Expired - Fee Related CA2262618C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US08/692,429 1996-08-05
US08/692,429 US5831046A (en) 1996-08-05 1996-08-05 Boronic acid-contaning nucleic acid monomers
PCT/US1997/012834 WO1998005672A1 (en) 1996-08-05 1997-07-31 Novel boronic acid-containing nucleic acids and their use as diagnostic agents

Publications (2)

Publication Number Publication Date
CA2262618A1 CA2262618A1 (en) 1998-02-12
CA2262618C true CA2262618C (en) 2007-10-02

Family

ID=24780549

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002262618A Expired - Fee Related CA2262618C (en) 1996-08-05 1997-07-31 Novel boronic acid-containing nucleic acids and their use as diagnostic agents

Country Status (6)

Country Link
US (3) US5831046A (2)
EP (1) EP0923591A4 (2)
JP (1) JP2000515546A (2)
AU (1) AU729907B2 (2)
CA (1) CA2262618C (2)
WO (1) WO1998005672A1 (2)

Families Citing this family (90)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4034351B2 (ja) 1996-04-25 2008-01-16 バイオアレイ ソリューションズ エルエルシー 粒子近接表面の光制御した動電学的アッセンブリ
US7041510B2 (en) * 1996-04-25 2006-05-09 Bioarray Solutions Ltd. System and method for programmable illumination pattern generation
US6630577B2 (en) 1996-08-05 2003-10-07 Prolinx, Inc. 1,2-Phenylenediboronic acid reagents and complexes
US6051251A (en) * 1997-11-20 2000-04-18 Alza Corporation Liposome loading method using a boronic acid compound
WO1999049082A2 (en) * 1998-03-23 1999-09-30 Invitrogen Corporation Modified nucleotides and methods useful for nucleic acid sequencing
US20010049438A1 (en) * 1999-03-19 2001-12-06 Dix Connie Kim Purification of primer extension products
DE60021862D1 (de) * 1999-03-19 2005-09-15 Agilent Technologies Inc Boronsäurehaltige reagenzien und oligonukleotide
US6013783A (en) * 1999-03-19 2000-01-11 Prolinx Incorporated Boronic acid containing oligonucleotides and polynucleotides
US6248884B1 (en) 1999-06-03 2001-06-19 The Perkin-Elmer Corporation Extended rhodamine compounds useful as fluorescent labels
JP2001183368A (ja) * 1999-12-27 2001-07-06 Fuji Photo Film Co Ltd 固相担体表面へのdna断片の固定方法及びdnaチップ
US6686461B1 (en) 2000-03-22 2004-02-03 Solulink Bioscience, Inc. Triphosphate oligonucleotide modification reagents and uses thereof
US7102024B1 (en) 2000-08-01 2006-09-05 Schwartz David A Functional biopolymer modification reagents and uses thereof
DE60117556T2 (de) 2000-06-21 2006-11-02 Bioarray Solutions Ltd. Multianalytische molekularanalyse durch verwendung anwendungsspezifischer zufallspartikelarrays
US9709559B2 (en) 2000-06-21 2017-07-18 Bioarray Solutions, Ltd. Multianalyte molecular analysis using application-specific random particle arrays
AU2001287399A1 (en) * 2000-08-16 2002-02-25 University Of Alberta Non-pressurized methods for the preparation of conjugated solid supports for boronic acids
US6919382B2 (en) 2000-08-31 2005-07-19 The Governors Of The University Of Alberta Preparation and uses of conjugated solid supports for boronic acids
US20030027135A1 (en) * 2001-03-02 2003-02-06 Ecker David J. Method for rapid detection and identification of bioagents
US20040121309A1 (en) 2002-12-06 2004-06-24 Ecker David J. Methods for rapid detection and identification of bioagents in blood, bodily fluids, and bodily tissues
US7226739B2 (en) 2001-03-02 2007-06-05 Isis Pharmaceuticals, Inc Methods for rapid detection and identification of bioagents in epidemiological and forensic investigations
US7666588B2 (en) * 2001-03-02 2010-02-23 Ibis Biosciences, Inc. Methods for rapid forensic analysis of mitochondrial DNA and characterization of mitochondrial DNA heteroplasmy
PL373962A1 (en) * 2001-05-21 2005-09-19 Aclara Biosciences, Inc. Methods and compositions for analyzing proteins
US7262063B2 (en) 2001-06-21 2007-08-28 Bio Array Solutions, Ltd. Directed assembly of functional heterostructures
US7217510B2 (en) * 2001-06-26 2007-05-15 Isis Pharmaceuticals, Inc. Methods for providing bacterial bioagent characterizing information
US8073627B2 (en) * 2001-06-26 2011-12-06 Ibis Biosciences, Inc. System for indentification of pathogens
EP1463825B1 (en) 2001-10-15 2017-12-06 BioArray Solutions Ltd. Multiplexed analysis of polymorphic loci by concurrent interrogation and enzyme-mediated detection
AU2002362013B2 (en) 2001-11-21 2008-04-24 Applied Biosystems, Llc. Digital assay
US20050221318A1 (en) * 2002-03-15 2005-10-06 Gouliaev Alex H Building block forming a c-c bond upon reaction
US7526114B2 (en) 2002-11-15 2009-04-28 Bioarray Solutions Ltd. Analysis, secure access to, and transmission of array images
JP2006516193A (ja) 2002-12-06 2006-06-29 アイシス・ファーマシューティカルス・インコーポレーテッド ヒトおよび動物における病原体の迅速な同定方法
WO2004065000A1 (en) * 2003-01-21 2004-08-05 Illumina Inc. Chemical reaction monitor
US8046171B2 (en) 2003-04-18 2011-10-25 Ibis Biosciences, Inc. Methods and apparatus for genetic evaluation
US8057993B2 (en) 2003-04-26 2011-11-15 Ibis Biosciences, Inc. Methods for identification of coronaviruses
US8158354B2 (en) 2003-05-13 2012-04-17 Ibis Biosciences, Inc. Methods for rapid purification of nucleic acids for subsequent analysis by mass spectrometry by solution capture
US7964343B2 (en) * 2003-05-13 2011-06-21 Ibis Biosciences, Inc. Method for rapid purification of nucleic acids for subsequent analysis by mass spectrometry by solution capture
US20060240412A1 (en) * 2003-09-11 2006-10-26 Hall Thomas A Compositions for use in identification of adenoviruses
US20080138808A1 (en) * 2003-09-11 2008-06-12 Hall Thomas A Methods for identification of sepsis-causing bacteria
US8546082B2 (en) 2003-09-11 2013-10-01 Ibis Biosciences, Inc. Methods for identification of sepsis-causing bacteria
US8097416B2 (en) 2003-09-11 2012-01-17 Ibis Biosciences, Inc. Methods for identification of sepsis-causing bacteria
US7956175B2 (en) * 2003-09-11 2011-06-07 Ibis Biosciences, Inc. Compositions for use in identification of bacteria
WO2005029705A2 (en) 2003-09-18 2005-03-31 Bioarray Solutions, Ltd. Number coding for identification of subtypes of coded types of solid phase carriers
CA2539824C (en) 2003-09-22 2015-02-03 Xinwen Wang Surface immobilized polyelectrolyte with multiple functional groups capable of covalently bonding to biomolecules
CA2899287A1 (en) 2003-10-28 2005-05-12 Bioarray Solutions Ltd. Optimization of gene expression analysis using immobilized capture probes
WO2005045060A2 (en) 2003-10-29 2005-05-19 Bioarray Solutions, Ltd. Multiplexed nucleic acid analysis by fragmentation of double-stranded dna
US7666592B2 (en) 2004-02-18 2010-02-23 Ibis Biosciences, Inc. Methods for concurrent identification and quantification of an unknown bioagent
US8119336B2 (en) * 2004-03-03 2012-02-21 Ibis Biosciences, Inc. Compositions for use in identification of alphaviruses
US7399645B2 (en) * 2004-05-12 2008-07-15 Applera Corporation Constrained cis-diol-borate bioconjugation system
EP2458619B1 (en) 2004-05-24 2017-08-02 Ibis Biosciences, Inc. Mass spectrometry with selective ion filtration by digital thresholding
US20050266411A1 (en) * 2004-05-25 2005-12-01 Hofstadler Steven A Methods for rapid forensic analysis of mitochondrial DNA
US7811753B2 (en) 2004-07-14 2010-10-12 Ibis Biosciences, Inc. Methods for repairing degraded DNA
US7848889B2 (en) 2004-08-02 2010-12-07 Bioarray Solutions, Ltd. Automated analysis of multiplexed probe-target interaction patterns: pattern matching and allele identification
WO2006135400A2 (en) 2004-08-24 2006-12-21 Isis Pharmaceuticals, Inc. Methods for rapid identification of recombinant organisms
NZ578297A (en) * 2005-02-16 2010-11-26 Anacor Pharmaceuticals Inc Boron-containing small molecules
WO2006094238A2 (en) 2005-03-03 2006-09-08 Isis Pharmaceuticals, Inc. Compositions for use in identification of adventitious viruses
US8084207B2 (en) * 2005-03-03 2011-12-27 Ibis Bioscience, Inc. Compositions for use in identification of papillomavirus
JP5162447B2 (ja) * 2005-04-13 2013-03-13 アイビス バイオサイエンシズ インコーポレイティッド アデノウイルスの同定に用いる組成物
US8486629B2 (en) 2005-06-01 2013-07-16 Bioarray Solutions, Ltd. Creation of functionalized microparticle libraries by oligonucleotide ligation or elongation
CA2616281C (en) * 2005-07-21 2014-04-22 Isis Pharmaceuticals, Inc. Methods for rapid identification and quantitation of mitochondrial dna variants
EP1976536A4 (en) 2005-12-30 2011-03-02 Anacor Pharmaceuticals Inc SMALL MOLECULES CONTAINING BORON
ME02188B (me) 2006-02-16 2016-02-20 Anacor Pharmaceuticals Inc Mali molekuli koji sadrže boron kao antiinflamatorni agensi
JP5420412B2 (ja) * 2006-09-14 2014-02-19 アイビス バイオサイエンシズ インコーポレイティッド 病原体の同定のための標的全ゲノム増幅方法
JP5680304B2 (ja) * 2007-02-23 2015-03-04 アイビス バイオサイエンシズ インコーポレイティッド 迅速な法医学的dna分析法
WO2008118809A1 (en) * 2007-03-23 2008-10-02 Ibis Biosciences, Inc. Compositions for use in identification of mixed populations of bioagents
US9598724B2 (en) 2007-06-01 2017-03-21 Ibis Biosciences, Inc. Methods and compositions for multiple displacement amplification of nucleic acids
JO3396B1 (ar) * 2007-06-20 2019-10-20 Anacor Pharmaceuticals Inc جزيئات صغيرة تحتوي على البورون
US8877156B2 (en) 2007-06-26 2014-11-04 New York University Contrast agents anchored by thiols on nanoparticles
WO2009012363A2 (en) * 2007-07-19 2009-01-22 Georgia State University Research Foundation, Inc. Nucleotides and aptamers containing boronic acid groups having biased binding to glycosylated proteins, and uses thereof
CN102014927A (zh) * 2008-03-06 2011-04-13 安纳考尔医药公司 作为抗炎药的含硼的小分子
WO2009140309A2 (en) * 2008-05-12 2009-11-19 Anacor Pharmaceuticals, Inc. Boron-containing small molecules
WO2010027975A1 (en) * 2008-09-04 2010-03-11 Anacor Pharmaceuticals, Inc. Boron-containing small molecules
US8461336B2 (en) 2008-09-04 2013-06-11 Anacor Pharmaceuticals, Inc. Boron-containing small molecules
US8148163B2 (en) 2008-09-16 2012-04-03 Ibis Biosciences, Inc. Sample processing units, systems, and related methods
EP2344893B1 (en) 2008-09-16 2014-10-15 Ibis Biosciences, Inc. Microplate handling systems and methods
WO2010033599A2 (en) 2008-09-16 2010-03-25 Ibis Biosciences, Inc. Mixing cartridges, mixing stations, and related kits, systems, and methods
US9493489B2 (en) * 2008-10-15 2016-11-15 Anacor Pharmaceuticals, Inc. Boron-containing small molecules as anti-protozoal agents
MX2011006334A (es) * 2008-12-17 2011-09-22 Anacor Pharmaceuticals Inc Polimorfos de (s)-3-amino-metil-7-(3-hidroxi-propoxi)-3h-benzo-[c] [1,2]-oxaborol-1-ol.
EP2396803A4 (en) 2009-02-12 2016-10-26 Ibis Biosciences Inc IONIZATION PROBE ASSEMBLIES
US8950604B2 (en) * 2009-07-17 2015-02-10 Ibis Biosciences, Inc. Lift and mount apparatus
US9194877B2 (en) 2009-07-17 2015-11-24 Ibis Biosciences, Inc. Systems for bioagent indentification
WO2011017125A1 (en) * 2009-07-28 2011-02-10 Anacor Pharmaceuticals, Inc. Trisubstituted boron-containing molecules
AP4039A (en) 2009-08-14 2017-02-28 Daitao Chen Boron-containing small molecules as antiprotozoal agents
WO2011022337A1 (en) * 2009-08-19 2011-02-24 Anacor Pharmaceuticals, Inc. Boron-containing small molecules as antiprotozoal agents
US20110124597A1 (en) * 2009-09-25 2011-05-26 Anacor Pharmaceuticals, Inc. Boron containing small molecules
WO2011041695A1 (en) * 2009-10-02 2011-04-07 Ibis Biosciences, Inc. Determination of methylation status of polynucleotides
ES2628739T3 (es) * 2009-10-15 2017-08-03 Ibis Biosciences, Inc. Amplificación por desplazamiento múltiple
WO2011049971A1 (en) 2009-10-20 2011-04-28 Anacor Pharmaceuticals, Inc. Boron-containing small molecules as antiprotozoal agents
US8461134B2 (en) * 2009-11-11 2013-06-11 Anacor Pharmaceuticals, Inc. Boron-containing small molecules
US8716478B2 (en) 2010-01-27 2014-05-06 Anacor Pharmaceuticals, Inc. Boron-containing small molecules
WO2011116348A1 (en) 2010-03-19 2011-09-22 Anacor Pharmaceuticals, Inc. Boron-containing small molecules as anti-protozoal agent
WO2012033858A2 (en) 2010-09-07 2012-03-15 Anacor Pharmaceuticals, Inc. Boron-containing small molecules
US11447506B2 (en) 2016-05-09 2022-09-20 Anacor Pharmaceuticals, Inc. Crystal forms of crisaborole in free form and preparation method and use thereof

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4711955A (en) * 1981-04-17 1987-12-08 Yale University Modified nucleotides and methods of preparing and using same
US5241060A (en) * 1982-06-23 1993-08-31 Enzo Diagnostics, Inc. Base moiety-labeled detectable nucleatide
US5177198A (en) * 1989-11-30 1993-01-05 University Of N.C. At Chapel Hill Process for preparing oligoribonucleoside and oligodeoxyribonucleoside boranophosphates
US5362732A (en) * 1989-12-20 1994-11-08 University Of North Carolina At Chapel Hill Boronated compounds
US5466679A (en) * 1993-05-17 1995-11-14 The Ohio State University Research Foundation Carboranyl uridines and their use in boron neutron capture therapy
US6180766B1 (en) * 1993-12-02 2001-01-30 Raymond F. Schinazi Nucleosides and oligonucleotides containing boron clusters
US5594111A (en) * 1994-01-28 1997-01-14 Prolinx, Inc. Phenylboronic acid complexes for bioconjugate preparation
CZ220196A3 (en) * 1994-01-28 1996-12-11 Prolinx Inc Bioconjugate complexes
US5594151A (en) * 1994-01-28 1997-01-14 Prolinx, Inc. Phenylboronic acid complexing reagents derived from aminosalicylic acid
US5473928A (en) * 1994-04-15 1995-12-12 Teitzel; Frederick E. Tool and method for straightening a panel
US5595878A (en) * 1995-06-02 1997-01-21 Boron Biologicals, Inc. Detection of biopolymers and biooligomers with boron hydride labels

Also Published As

Publication number Publication date
CA2262618A1 (en) 1998-02-12
AU729907B2 (en) 2001-02-15
US5876938A (en) 1999-03-02
JP2000515546A (ja) 2000-11-21
EP0923591A1 (en) 1999-06-23
US5831045A (en) 1998-11-03
EP0923591A4 (en) 2001-01-31
AU3809097A (en) 1998-02-25
WO1998005672A1 (en) 1998-02-12
US5831046A (en) 1998-11-03

Similar Documents

Publication Publication Date Title
CA2262618C (en) Novel boronic acid-containing nucleic acids and their use as diagnostic agents
EP0543913B1 (en) Oligo(alpha-arabinofuranosyl nucleotides) and alpha-arabinofuranosyl precursors thereof
US5817786A (en) Single-stranded labelled oligonucleotides of preselected sequences
Roget et al. Synthesis and use of labelled nudeoside phosphoramidite building blocks bearing a reporter group: biotinyl, dinitrophenyl, pyrenyl and dansyl
CA1303526C (en) Compositions and methods for functionalizing nucleic acids
KR100218113B1 (ko) 신규 염기쌍 설계를 이용한 비특이적 혼성화의 감소방법
US6107039A (en) Assays using base protected table 1
JPH0714954B2 (ja) ヌクレオチド架橋試薬として使用するためのクマリン誘導体
JPH07504087A (ja) 蛍光性n−ヌクレオシド及び蛍光性n−ヌクレオシド構造類似体の応用
JP2002527523A (ja) 機能付与したピリミジン誘導体
JPH04507402A (ja) 架橋オリゴヌクレオチド
WO1998003532A9 (en) Base-protected nucleotide analogs with protected thiol groups
US5646261A (en) 3'-derivatized oligonucleotide analogs with non-nucleotidic groupings, their preparation and use
EP2669291A1 (en) Modified Nucleotides Methods and Kits
US20070015725A1 (en) 2-azapurine compounds and their uses
JPH03505209A (ja) 標的付与されたオリゴヌクレオチド類の合成に使用できるヌクレオシド誘導体類、これ等誘導体類から得たオリゴヌクレオチド類及びそれ等の合成
JPH01500353A (ja) 2′‐デオキシアデノシン誘導体を含む核酸検出用プローブ
Nadeau et al. Use of ribonucleosides as protecting groups in synthesis of polynucleotides with phosphorylated terminals
JPH0374239B2 (2)
Davis et al. Introduction of hypermodified nucleotides in RNA
JPH064670B2 (ja) 酵素標識化されたポリヌクレオチドおよびその製法

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed