JPH10509740A - カチオン性オリゴヌクレオチド、ならびに関連の合成および使用の方法 - Google Patents
カチオン性オリゴヌクレオチド、ならびに関連の合成および使用の方法Info
- Publication number
- JPH10509740A JPH10509740A JP9508693A JP50869397A JPH10509740A JP H10509740 A JPH10509740 A JP H10509740A JP 9508693 A JP9508693 A JP 9508693A JP 50869397 A JP50869397 A JP 50869397A JP H10509740 A JPH10509740 A JP H10509740A
- Authority
- JP
- Japan
- Prior art keywords
- group
- alkyl
- cationic
- independently selected
- bond
- 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
Links
- 108091034117 Oligonucleotide Proteins 0.000 title claims abstract description 116
- 125000002091 cationic group Chemical group 0.000 title claims abstract description 100
- 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 claims abstract description 76
- 238000000034 method Methods 0.000 title claims abstract description 29
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- 238000003786 synthesis reaction Methods 0.000 title description 11
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 29
- 125000000129 anionic group Chemical group 0.000 claims abstract description 23
- 125000004437 phosphorous atom Chemical group 0.000 claims abstract description 21
- 238000007899 nucleic acid hybridization Methods 0.000 claims abstract description 15
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- 229910052760 oxygen Inorganic materials 0.000 claims description 48
- 229910052717 sulfur Inorganic materials 0.000 claims description 46
- -1 phospho Chemical class 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 26
- 102000039446 nucleic acids Human genes 0.000 claims description 26
- 108020004707 nucleic acids Proteins 0.000 claims description 26
- 150000007523 nucleic acids Chemical class 0.000 claims description 26
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- 125000003729 nucleotide group Chemical group 0.000 claims description 18
- 239000002773 nucleotide Substances 0.000 claims description 17
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 125000000732 arylene group Chemical group 0.000 claims description 10
- 229910052711 selenium Inorganic materials 0.000 claims description 10
- 125000002950 monocyclic group Chemical group 0.000 claims description 9
- 150000008300 phosphoramidites Chemical class 0.000 claims description 6
- 238000010898 silica gel chromatography Methods 0.000 claims description 5
- 108020005187 Oligonucleotide Probes Proteins 0.000 claims description 4
- 239000012491 analyte Substances 0.000 claims description 4
- 239000002751 oligonucleotide probe Substances 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 230000000692 anti-sense effect Effects 0.000 abstract description 12
- 150000001875 compounds Chemical class 0.000 abstract description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 74
- 239000011780 sodium chloride Substances 0.000 description 39
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 24
- PTMHPRAIXMAOOB-UHFFFAOYSA-L phosphoramidate Chemical compound NP([O-])([O-])=O PTMHPRAIXMAOOB-UHFFFAOYSA-L 0.000 description 23
- 150000003839 salts Chemical class 0.000 description 23
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 22
- 230000007704 transition Effects 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 20
- 108020004414 DNA Proteins 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 description 14
- 238000010828 elution Methods 0.000 description 14
- 239000000539 dimer Substances 0.000 description 13
- 238000009396 hybridization Methods 0.000 description 13
- 238000004679 31P NMR spectroscopy Methods 0.000 description 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 12
- 238000004809 thin layer chromatography Methods 0.000 description 12
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 10
- 150000004713 phosphodiesters Chemical class 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 238000001228 spectrum Methods 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
- 108091034057 RNA (poly(A)) Proteins 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 108091032973 (ribonucleotides)n+m Proteins 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 102000053602 DNA Human genes 0.000 description 7
- 125000002947 alkylene group Chemical group 0.000 description 7
- 239000011574 phosphorus Substances 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 6
- DWRXFEITVBNRMK-UHFFFAOYSA-N Beta-D-1-Arabinofuranosylthymine Natural products O=C1NC(=O)C(C)=CN1C1C(O)C(O)C(CO)O1 DWRXFEITVBNRMK-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 6
- IQFYYKKMVGJFEH-UHFFFAOYSA-N beta-L-thymidine Natural products O=C1NC(=O)C(C)=CN1C1OC(CO)C(O)C1 IQFYYKKMVGJFEH-UHFFFAOYSA-N 0.000 description 6
- 238000010494 dissociation reaction Methods 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 235000000346 sugar Nutrition 0.000 description 6
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 6
- 229940104230 thymidine Drugs 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 5
- 238000001142 circular dichroism spectrum Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 230000005593 dissociations Effects 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 150000003833 nucleoside derivatives Chemical class 0.000 description 5
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- 238000004007 reversed phase HPLC Methods 0.000 description 5
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- SXUXMRMBWZCMEN-ZOQUXTDFSA-N 2'-O-methyluridine Chemical compound CO[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=C1 SXUXMRMBWZCMEN-ZOQUXTDFSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 101710163270 Nuclease Proteins 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- PYMYPHUHKUWMLA-LMVFSUKVSA-N aldehydo-D-ribose Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 description 4
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- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 4
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
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- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
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- QQVDJLLNRSOCEL-UHFFFAOYSA-N (2-aminoethyl)phosphonic acid Chemical compound [NH3+]CCP(O)([O-])=O QQVDJLLNRSOCEL-UHFFFAOYSA-N 0.000 description 1
- KFYRJJBUHYILSO-YFKPBYRVSA-N (2s)-2-amino-3-dimethylarsanylsulfanyl-3-methylbutanoic acid Chemical compound C[As](C)SC(C)(C)[C@@H](N)C(O)=O KFYRJJBUHYILSO-YFKPBYRVSA-N 0.000 description 1
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Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Q—MEASURING 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
- C12Q1/00—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
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Q—MEASURING 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
- C12Q1/00—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
- C12Q1/6839—Triple helix formation or other higher order conformations in hybridisation assays
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Immunology (AREA)
- Microbiology (AREA)
- Analytical Chemistry (AREA)
- Physics & Mathematics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US190195P | 1995-08-04 | 1995-08-04 | |
| US60/001,901 | 1995-08-04 | ||
| US08/693,831 | 1996-07-31 | ||
| US08/693,831 US6017700A (en) | 1995-08-04 | 1996-07-31 | Cationic oligonucleotides, and related methods of synthesis and use |
| PCT/US1996/013056 WO1997006183A1 (en) | 1995-08-04 | 1996-08-01 | Cationic oligonucleotides, and related methods of synthesis and use |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007208670A Division JP2008013571A (ja) | 1995-08-04 | 2007-08-09 | カチオン性オリゴヌクレオチド、ならびに関連の合成および使用の方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH10509740A true JPH10509740A (ja) | 1998-09-22 |
| JPH10509740A5 JPH10509740A5 (enExample) | 2004-09-09 |
Family
ID=26669648
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9508693A Expired - Lifetime JPH10509740A (ja) | 1995-08-04 | 1996-08-01 | カチオン性オリゴヌクレオチド、ならびに関連の合成および使用の方法 |
| JP2007208670A Pending JP2008013571A (ja) | 1995-08-04 | 2007-08-09 | カチオン性オリゴヌクレオチド、ならびに関連の合成および使用の方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007208670A Pending JP2008013571A (ja) | 1995-08-04 | 2007-08-09 | カチオン性オリゴヌクレオチド、ならびに関連の合成および使用の方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6017700A (enExample) |
| EP (1) | EP0785942A1 (enExample) |
| JP (2) | JPH10509740A (enExample) |
| AU (1) | AU702309B2 (enExample) |
| CA (1) | CA2201963A1 (enExample) |
| WO (1) | WO1997006183A1 (enExample) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005200405A (ja) * | 2003-12-02 | 2005-07-28 | F Hoffmann La Roche Ag | 分子ロッドを含むオリゴヌクレオチド |
| JP2009543783A (ja) * | 2006-07-12 | 2009-12-10 | ザ レジェンツ オブ ザ ユニヴァースティ オブ カリフォルニア | 可逆的なホスホトリエステル電荷中和保護基による核酸の形質導入可能な送達 |
| JP2015528002A (ja) * | 2012-07-13 | 2015-09-24 | ウェイブ ライフ サイエンス プライベート リミテッド | キラル制御 |
| JPWO2022230990A1 (enExample) * | 2021-04-28 | 2022-11-03 | ||
| US11597744B2 (en) | 2017-06-30 | 2023-03-07 | Sirius Therapeutics, Inc. | Chiral phosphoramidite auxiliaries and methods of their use |
| US11981703B2 (en) | 2016-08-17 | 2024-05-14 | Sirius Therapeutics, Inc. | Polynucleotide constructs |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004537263A (ja) * | 2000-12-14 | 2004-12-16 | ジェン−プローブ・インコーポレーテッド | ポリヌクレオチドの会合速度を増強するための方法およびキット |
| BRPI0923225A2 (pt) | 2008-12-02 | 2016-10-04 | Chiralgen Ltd | metodo para sintese de acidos nucleicos modificados no atomo de fosforo |
| EP2451461A4 (en) | 2009-07-06 | 2013-05-29 | Ontorii Inc | NOVEL NUCLEIC ACID PRODRUGS AND METHOD OF USE THEREOF |
| DK2620428T3 (da) | 2010-09-24 | 2019-07-01 | Wave Life Sciences Ltd | Asymmetrisk hjælpegruppe |
| MX345065B (es) * | 2011-05-10 | 2017-01-16 | Bonac Corp | Proceso para preparar un compuesto de fosfato marcado con isotopos. |
| CN107365339A (zh) | 2011-07-19 | 2017-11-21 | 波涛生命科学有限公司 | 合成官能化核酸的方法 |
| SG11201500243WA (en) | 2012-07-13 | 2015-04-29 | Shin Nippon Biomedical Lab Ltd | Chiral nucleic acid adjuvant |
| WO2014010250A1 (en) | 2012-07-13 | 2014-01-16 | Chiralgen, Ltd. | Asymmetric auxiliary group |
| JP2015529073A (ja) | 2012-08-20 | 2015-10-05 | ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア | 生物可逆性基を有するポリヌクレオチド |
| KR102285326B1 (ko) | 2013-06-28 | 2021-08-04 | 에트리스 게엠베하 | Rna를 세포에 도입하기 위한 조성물 |
| US9410172B2 (en) | 2013-09-16 | 2016-08-09 | General Electric Company | Isothermal amplification using oligocation-conjugated primer sequences |
| EP3095459A4 (en) | 2014-01-15 | 2017-08-23 | Shin Nippon Biomedical Laboratories, Ltd. | Chiral nucleic acid adjuvant having antitumor effect and antitumor agent |
| WO2015108046A1 (ja) | 2014-01-15 | 2015-07-23 | 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 |
| EP3095461A4 (en) | 2014-01-15 | 2017-08-23 | Shin Nippon Biomedical Laboratories, Ltd. | Chiral nucleic acid adjuvant having immunity induction activity, and immunity induction activator |
| EP3094728B1 (en) | 2014-01-16 | 2022-03-09 | Wave Life Sciences Ltd. | Chiral design |
| JP2017507946A (ja) | 2014-02-26 | 2017-03-23 | エスリス ゲーエムベーハーｅｔｈｒｉｓ ＧｍｂＨ | Ｒｎａを胃腸内投与するための組成物 |
| EP3034539A1 (en) | 2014-12-19 | 2016-06-22 | Ethris GmbH | Compositions for introducing nucleic acid into cells |
| BR112019021520A2 (pt) | 2017-04-14 | 2020-08-04 | Tollnine, Inc. | oligonucleotídeo, composto, polinucleotídeo imunomodulador, composição, conjugado, método para modular um receptor, método de tratamento de um tumor, método de tratamento de câncer, método para tratar um tumor, método de prevenção de câncer, método para induzir uma resposta imune |
| JP7256824B2 (ja) | 2018-04-25 | 2023-04-12 | エスリス ゲーエムベーハー | 粒子状製剤用の凍結保護剤 |
| MX2023009757A (es) | 2021-02-26 | 2023-09-04 | Ethris Gmbh | Formulaciones para la formacion de aerosoles y aerosoles para la administracion de acido nucleico. |
| EP4327829A1 (en) | 2022-08-26 | 2024-02-28 | Ethris GmbH | Stabilization of lipid or lipidoid nanoparticle suspensions |
| EP4577243A1 (en) | 2022-08-26 | 2025-07-02 | Ethris GmbH | Stable lipid or lipidoid nanoparticle suspensions |
| CN121729225A (zh) | 2023-08-25 | 2026-03-24 | 埃泽瑞斯公司 | 具有增强药物应用的特定表面活性剂性质的稳定脂质和类脂质纳米颗粒制剂 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2586704B1 (fr) * | 1985-09-04 | 1987-12-18 | Centre Nat Rech Scient | Nouveaux composes comportant une sequence d'oligonucleotide liee a un agent d'intercalation et a un groupe chimique activable, leur synthese et leurs applications a titre de nucleases artificielles specifiques de sequences. centre national de la recherche scientifique (cnrs) |
| US4868105A (en) * | 1985-12-11 | 1989-09-19 | Chiron Corporation | Solution phase nucleic acid sandwich assay |
| DE3916871A1 (de) * | 1989-05-24 | 1990-11-29 | Boehringer Mannheim Gmbh | Modifiziertes phosphoramidit-verfahren zur herstellung von modifizierten nukleinsaeuren |
| US4958013A (en) * | 1989-06-06 | 1990-09-18 | Northwestern University | Cholesteryl modified oligonucleotides |
| WO1993011148A1 (en) * | 1991-11-25 | 1993-06-10 | Pharmagenics, Inc. | Oligonucleotides having aminohydrocarbon phosphonate moieties |
-
1996
- 1996-07-31 US US08/693,831 patent/US6017700A/en not_active Expired - Lifetime
- 1996-08-01 WO PCT/US1996/013056 patent/WO1997006183A1/en not_active Ceased
- 1996-08-01 JP JP9508693A patent/JPH10509740A/ja not_active Expired - Lifetime
- 1996-08-01 AU AU68971/96A patent/AU702309B2/en not_active Ceased
- 1996-08-01 EP EP96929675A patent/EP0785942A1/en not_active Withdrawn
- 1996-08-01 CA CA002201963A patent/CA2201963A1/en not_active Abandoned
-
2007
- 2007-08-09 JP JP2007208670A patent/JP2008013571A/ja active Pending
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005200405A (ja) * | 2003-12-02 | 2005-07-28 | F Hoffmann La Roche Ag | 分子ロッドを含むオリゴヌクレオチド |
| JP2009543783A (ja) * | 2006-07-12 | 2009-12-10 | ザ レジェンツ オブ ザ ユニヴァースティ オブ カリフォルニア | 可逆的なホスホトリエステル電荷中和保護基による核酸の形質導入可能な送達 |
| JP2015062421A (ja) * | 2006-07-12 | 2015-04-09 | ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア | 可逆的なホスホトリエステル電荷中和保護基による核酸の形質導入可能な送達 |
| JP2015528002A (ja) * | 2012-07-13 | 2015-09-24 | ウェイブ ライフ サイエンス プライベート リミテッド | キラル制御 |
| JP2019069971A (ja) * | 2012-07-13 | 2019-05-09 | 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 |
| US11981703B2 (en) | 2016-08-17 | 2024-05-14 | Sirius Therapeutics, Inc. | Polynucleotide constructs |
| US11597744B2 (en) | 2017-06-30 | 2023-03-07 | Sirius Therapeutics, Inc. | Chiral phosphoramidite auxiliaries and methods of their use |
| JPWO2022230990A1 (enExample) * | 2021-04-28 | 2022-11-03 | ||
| WO2022230990A1 (ja) * | 2021-04-28 | 2022-11-03 | 国立研究開発法人科学技術振興機構 | 人工核酸及びそれを用いた核酸の送達方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| US6017700A (en) | 2000-01-25 |
| AU702309B2 (en) | 1999-02-18 |
| WO1997006183A1 (en) | 1997-02-20 |
| JP2008013571A (ja) | 2008-01-24 |
| EP0785942A1 (en) | 1997-07-30 |
| AU6897196A (en) | 1997-03-05 |
| CA2201963A1 (en) | 1997-02-20 |
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