AU762212C - Oligonucleotides having A-DNA form and B-DNA form conformational geometry - Google Patents
Oligonucleotides having A-DNA form and B-DNA form conformational geometryInfo
- Publication number
- AU762212C AU762212C AU46910/00A AU4691000A AU762212C AU 762212 C AU762212 C AU 762212C AU 46910/00 A AU46910/00 A AU 46910/00A AU 4691000 A AU4691000 A AU 4691000A AU 762212 C AU762212 C AU 762212C
- Authority
- AU
- Australia
- Prior art keywords
- nucleotides
- oligonucleotide
- ribonucleotide
- linkage
- joined together
- 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.)
- Ceased
Links
- 108091034117 Oligonucleotide Proteins 0.000 title claims description 349
- JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 title description 189
- 108091092742 A-DNA Proteins 0.000 title description 7
- 239000002773 nucleotide Substances 0.000 claims description 193
- 125000003729 nucleotide group Chemical group 0.000 claims description 193
- 239000002336 ribonucleotide Substances 0.000 claims description 118
- 108091028664 Ribonucleotide Proteins 0.000 claims description 117
- 239000002214 arabinonucleotide Substances 0.000 claims description 61
- 125000002652 ribonucleotide group Chemical group 0.000 claims description 57
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 claims description 50
- -1 methylene(methylimino) Chemical class 0.000 claims description 46
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 32
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 26
- 150000004713 phosphodiesters Chemical class 0.000 claims description 25
- 239000007787 solid Substances 0.000 claims description 23
- 238000006467 substitution reaction Methods 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 229910019142 PO4 Inorganic materials 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 239000010452 phosphate Substances 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 150000003568 thioethers Chemical class 0.000 claims description 10
- 125000001931 aliphatic group Chemical group 0.000 claims description 9
- 125000004122 cyclic group Chemical group 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- ASFAFOSQXBRFMV-LJQANCHMSA-N 3-n-(2-benzyl-1,3-dihydroxypropan-2-yl)-1-n-[(1r)-1-(4-fluorophenyl)ethyl]-5-[methyl(methylsulfonyl)amino]benzene-1,3-dicarboxamide Chemical compound N([C@H](C)C=1C=CC(F)=CC=1)C(=O)C(C=1)=CC(N(C)S(C)(=O)=O)=CC=1C(=O)NC(CO)(CO)CC1=CC=CC=C1 ASFAFOSQXBRFMV-LJQANCHMSA-N 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 8
- 150000001408 amides Chemical class 0.000 claims description 7
- 125000001188 haloalkyl group Chemical group 0.000 claims description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 229910052717 sulfur Chemical group 0.000 claims description 6
- 239000011593 sulfur Chemical group 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000001246 bromo group Chemical group Br* 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- NAGJZTKCGNOGPW-UHFFFAOYSA-K dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [O-]P([O-])([S-])=S NAGJZTKCGNOGPW-UHFFFAOYSA-K 0.000 claims description 5
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- BYDUPHGNAAJNJO-UHFFFAOYSA-N [hydrazinyl(methyl)amino]methane Chemical compound CN(C)NN BYDUPHGNAAJNJO-UHFFFAOYSA-N 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 128
- 210000004027 cell Anatomy 0.000 description 103
- 108091032973 (ribonucleotides)n+m Proteins 0.000 description 95
- 150000001875 compounds Chemical class 0.000 description 93
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- 239000005289 controlled pore glass Substances 0.000 description 74
- 238000012986 modification Methods 0.000 description 74
- 238000000034 method Methods 0.000 description 72
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
- 230000004048 modification Effects 0.000 description 65
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 64
- 101710163270 Nuclease Proteins 0.000 description 61
- 125000003835 nucleoside group Chemical group 0.000 description 57
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 52
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- 108010093579 Arachidonate 5-lipoxygenase Proteins 0.000 description 40
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 40
- 238000006243 chemical reaction Methods 0.000 description 39
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- 239000002126 C01EB10 - Adenosine Substances 0.000 description 37
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 29
- 125000001424 substituent group Chemical group 0.000 description 29
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
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Classifications
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- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Enzymes And Modification Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
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| US09/303586 | 1999-05-03 | ||
| US09/303,586 US6369209B1 (en) | 1999-05-03 | 1999-05-03 | Oligonucleotides having A-DNA form and B-DNA form conformational geometry |
| PCT/US2000/011913 WO2000066609A1 (en) | 1999-05-03 | 2000-05-03 | Oligonucleotides having a-dna form and b-dna form conformational geometry |
Publications (3)
| Publication Number | Publication Date |
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| AU4691000A AU4691000A (en) | 2000-11-17 |
| AU762212B2 AU762212B2 (en) | 2003-06-19 |
| AU762212C true AU762212C (en) | 2004-02-12 |
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|---|---|---|---|
| AU46910/00A Ceased AU762212C (en) | 1999-05-03 | 2000-05-03 | Oligonucleotides having A-DNA form and B-DNA form conformational geometry |
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| US (2) | US6369209B1 (cg-RX-API-DMAC7.html) |
| EP (2) | EP1180113A4 (cg-RX-API-DMAC7.html) |
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| AU (1) | AU762212C (cg-RX-API-DMAC7.html) |
| CA (1) | CA2373225A1 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2000066609A1 (cg-RX-API-DMAC7.html) |
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| US7119184B2 (en) * | 1991-08-12 | 2006-10-10 | Isis Pharmaceuticals, Inc. | Oligonucleotides having A-DNA form and B-DNA form conformational geometry |
| US6271358B1 (en) * | 1998-07-27 | 2001-08-07 | Isis Pharmaceuticals, Inc. | RNA targeted 2′-modified oligonucleotides that are conformationally preorganized |
| EP1368495A4 (en) * | 2001-02-19 | 2005-12-14 | Genvartec Pty Ltd | METHOD FOR IDENTIFYING DIFFERENCES BETWEEN NUCLEIC ACID MOLECULES |
| US20040234992A1 (en) * | 2001-09-13 | 2004-11-25 | Cotton Richard G | Method of detection of conformational change in a nucleic acid duplex by treatment with oxidising or reactive agent as a result of exposure to environmental or chemical conditions |
| US20040009602A1 (en) * | 2002-05-13 | 2004-01-15 | The Government Of The U.S.A. As Represented By The Secretary Of The Dept. Of Health & Human Services | DNA modifying molecules and methods of use thereof |
| US20040198640A1 (en) * | 2003-04-02 | 2004-10-07 | Dharmacon, Inc. | Stabilized polynucleotides for use in RNA interference |
| US20050074801A1 (en) | 2003-09-09 | 2005-04-07 | Monia Brett P. | Chimeric oligomeric compounds comprising alternating regions of northern and southern conformational geometry |
| US20090280567A1 (en) * | 2004-02-06 | 2009-11-12 | Dharmacon, Inc. | Stabilized sirnas as transfection controls and silencing reagents |
| WO2005078094A2 (en) * | 2004-02-06 | 2005-08-25 | Dharmacon, Inc. | Stabilized rnas as transfection controls and silencing reagents |
| US8790919B2 (en) * | 2004-03-15 | 2014-07-29 | Isis Pharmaceuticals, Inc. | Compositions and methods for optimizing cleavage of RNA by RNase H |
| KR101147147B1 (ko) * | 2004-04-01 | 2012-05-25 | 머크 샤프 앤드 돔 코포레이션 | Ｒｎａ 간섭의 오프 타겟 효과 감소를 위한 변형된폴리뉴클레오타이드 |
| US20050244869A1 (en) * | 2004-04-05 | 2005-11-03 | Brown-Driver Vickie L | Modulation of transthyretin expression |
| KR20070101226A (ko) * | 2004-09-07 | 2007-10-16 | 아케믹스 코포레이션 | 앱타머의 약화학 |
| EP2302055B1 (en) | 2004-11-12 | 2014-08-27 | Asuragen, Inc. | Methods and compositions involving miRNA and miRNA inhibitor molecules |
| US7935811B2 (en) * | 2004-11-22 | 2011-05-03 | Dharmacon, Inc. | Apparatus and system having dry gene silencing compositions |
| US7923207B2 (en) | 2004-11-22 | 2011-04-12 | Dharmacon, Inc. | Apparatus and system having dry gene silencing pools |
| US20060166234A1 (en) * | 2004-11-22 | 2006-07-27 | Barbara Robertson | Apparatus and system having dry control gene silencing compositions |
| US7875352B2 (en) * | 2004-12-03 | 2011-01-25 | Japan Science And Technology Agency | Stabilized inorganic nanoparticle, stabilized inorganic nanoparticle material, method for producing stabilized inorganic nanoparticle, and method for using stabilized inorganic nanoparticle |
| US20060223777A1 (en) * | 2005-03-29 | 2006-10-05 | Dharmacon, Inc. | Highly functional short hairpin RNA |
| ES2911034T3 (es) | 2006-08-08 | 2022-05-17 | Univ Bonn Rheinische Friedrich Wilhelms | Estructura y uso de oligonucleótidos 5' fosfato |
| AU2007299705B2 (en) * | 2006-09-22 | 2012-09-06 | Dharmacon, Inc. | Duplex oligonucleotide complexes and methods for gene silencing by RNA interference |
| US8188060B2 (en) | 2008-02-11 | 2012-05-29 | Dharmacon, Inc. | Duplex oligonucleotides with enhanced functionality in gene regulation |
| WO2009141146A1 (en) | 2008-05-21 | 2009-11-26 | Gunther Hartmann | 5' triphosphate oligonucleotide with blunt end and uses thereof |
| EP2323667A4 (en) * | 2008-08-07 | 2012-07-25 | Isis Pharmaceuticals Inc | MODULATION OF TRANSTHYRETIN EXPRESSION BY TREATMENT OF CNS DISEASES |
| CN102282155B (zh) | 2008-12-02 | 2017-06-09 | 日本波涛生命科学公司 | 磷原子修饰的核酸的合成方法 |
| US20120149888A1 (en) * | 2009-02-22 | 2012-06-14 | Srivastava Suresh C | Synthesis of ara-2'-o-methyl-nucleosides, corresponding phosphoramidites and oligonucleotides incorporating novel modifications for biological application in therapeuctics, diagnostics, g- tetrad forming oligonucleotides and aptamers |
| RU2612521C2 (ru) | 2009-07-06 | 2017-03-09 | Онтории, Инк. | Новые пролекарства нуклеиновых кислот и способы их применения |
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- 1999-05-03 US US09/303,586 patent/US6369209B1/en not_active Expired - Lifetime
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2000
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- 2000-05-03 EP EP00928716A patent/EP1180113A4/en not_active Withdrawn
- 2000-05-03 JP JP2000615638A patent/JP2002543215A/ja active Pending
- 2000-05-03 CA CA002373225A patent/CA2373225A1/en not_active Abandoned
- 2000-05-03 EP EP06075012A patent/EP1743901A3/en not_active Withdrawn
- 2000-05-03 WO PCT/US2000/011913 patent/WO2000066609A1/en not_active Ceased
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2002
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|---|---|
| EP1180113A4 (en) | 2002-09-18 |
| US6737520B2 (en) | 2004-05-18 |
| US6369209B1 (en) | 2002-04-09 |
| EP1743901A2 (en) | 2007-01-17 |
| JP2002543215A (ja) | 2002-12-17 |
| EP1180113A1 (en) | 2002-02-20 |
| AU4691000A (en) | 2000-11-17 |
| AU762212B2 (en) | 2003-06-19 |
| US20030105311A1 (en) | 2003-06-05 |
| EP1743901A3 (en) | 2009-01-28 |
| WO2000066609A1 (en) | 2000-11-09 |
| CA2373225A1 (en) | 2000-11-09 |
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