JP4175667B2 - トランスフェクションのためのカチオン試薬 - Google Patents
トランスフェクションのためのカチオン試薬 Download PDFInfo
- Publication number
- JP4175667B2 JP4175667B2 JP52084398A JP52084398A JP4175667B2 JP 4175667 B2 JP4175667 B2 JP 4175667B2 JP 52084398 A JP52084398 A JP 52084398A JP 52084398 A JP52084398 A JP 52084398A JP 4175667 B2 JP4175667 B2 JP 4175667B2
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- liposome
- branched
- dna
- alkynyl
- 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
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- 238000001890 transfection Methods 0.000 title claims description 58
- 239000003153 chemical reaction reagent Substances 0.000 title description 6
- 150000001768 cations Chemical class 0.000 title 1
- 239000002502 liposome Substances 0.000 claims description 93
- 150000001875 compounds Chemical class 0.000 claims description 79
- 210000004027 cell Anatomy 0.000 claims description 67
- -1 oxalate Anion Chemical class 0.000 claims description 48
- 108020004414 DNA Proteins 0.000 claims description 43
- 238000000338 in vitro Methods 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 12
- 239000013612 plasmid Substances 0.000 claims description 11
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims description 8
- 108091034117 Oligonucleotide Proteins 0.000 claims description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 claims description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 claims description 7
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 claims description 7
- 108091032973 (ribonucleotides)n+m Proteins 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 6
- 239000003446 ligand Substances 0.000 claims description 6
- 230000008685 targeting Effects 0.000 claims description 6
- JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 claims description 5
- 230000037396 body weight Effects 0.000 claims description 5
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
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- 239000000460 chlorine Substances 0.000 claims description 4
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- 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims 4
- 102000053602 DNA Human genes 0.000 claims 2
- 150000001261 hydroxy acids Chemical class 0.000 claims 2
- 108020004682 Single-Stranded DNA Proteins 0.000 claims 1
- 102000006255 nuclear receptors Human genes 0.000 claims 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 description 59
- MWRBNPKJOOWZPW-CLFAGFIQSA-N dioleoyl phosphatidylethanolamine Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(COP(O)(=O)OCCN)OC(=O)CCCCCCC\C=C/CCCCCCCC MWRBNPKJOOWZPW-CLFAGFIQSA-N 0.000 description 29
- 238000002360 preparation method Methods 0.000 description 29
- 150000002632 lipids Chemical class 0.000 description 21
- 238000000034 method Methods 0.000 description 20
- 125000002091 cationic group Chemical group 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- 239000002609 medium Substances 0.000 description 16
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 108090000623 proteins and genes Proteins 0.000 description 13
- 125000000304 alkynyl group Chemical group 0.000 description 12
- 238000001727 in vivo Methods 0.000 description 11
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- 125000000217 alkyl group Chemical group 0.000 description 7
- SRESKMPUIWAGML-UHFFFAOYSA-N n,n-dimethyldecan-1-amine;hydrobromide Chemical compound Br.CCCCCCCCCCN(C)C SRESKMPUIWAGML-UHFFFAOYSA-N 0.000 description 7
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 6
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- WQZGKKKJIJFFOK-FPRJBGLDSA-N beta-D-galactose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-FPRJBGLDSA-N 0.000 description 5
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 3
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- 108020004635 Complementary DNA Proteins 0.000 description 3
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- 150000001720 carbohydrates Chemical class 0.000 description 3
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Classifications
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- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N15/00—Mutation or genetic engineering; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification; Use of hosts therefor
- C12N15/09—Recombinant DNA-technology
- C12N15/87—Introduction of foreign genetic material using processes not otherwise provided for, e.g. co-transformation
- C12N15/88—Introduction of foreign genetic material using processes not otherwise provided for, e.g. co-transformation using microencapsulation, e.g. using amphiphile liposome vesicle
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- A—HUMAN NECESSITIES
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- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/54—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
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- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/54—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
- A61K47/543—Lipids, e.g. triglycerides; Polyamines, e.g. spermine or spermidine
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- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/54—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K48/00—Medicinal preparations containing genetic material which is inserted into cells of the living body to treat genetic diseases; Gene therapy
Landscapes
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- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
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- Bioinformatics & Cheminformatics (AREA)
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- Dispersion Chemistry (AREA)
- Biochemistry (AREA)
- Plant Pathology (AREA)
- Medicinal Preparation (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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3031596P | 1996-11-04 | 1996-11-04 | |
| US60/030,315 | 1996-11-04 | ||
| PCT/EP1997/006035 WO1998019709A2 (en) | 1996-11-04 | 1997-11-03 | Cationic reagents for transfection |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2001503751A JP2001503751A (ja) | 2001-03-21 |
| JP2001503751A5 JP2001503751A5 (enExample) | 2005-03-10 |
| JP4175667B2 true JP4175667B2 (ja) | 2008-11-05 |
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|---|---|---|---|
| JP52084398A Expired - Lifetime JP4175667B2 (ja) | 1996-11-04 | 1997-11-03 | トランスフェクションのためのカチオン試薬 |
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| US (2) | US6733777B2 (enExample) |
| EP (1) | EP1003556B1 (enExample) |
| JP (1) | JP4175667B2 (enExample) |
| AU (1) | AU738384B2 (enExample) |
| CA (1) | CA2270396C (enExample) |
| DE (1) | DE69735382T2 (enExample) |
| WO (1) | WO1998019709A2 (enExample) |
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| US5674908A (en) | 1993-12-20 | 1997-10-07 | Life Technologies, Inc. | Highly packed polycationic ammonium, sulfonium and phosphonium lipids |
| US6989434B1 (en) | 1994-02-11 | 2006-01-24 | Invitrogen Corporation | Reagents for intracellular delivery of macromolecules |
| AU738384B2 (en) * | 1996-11-04 | 2001-09-20 | Qiagen Gmbh | Cationic reagents for transfection |
| CA2350882C (en) | 1998-11-12 | 2011-02-22 | Life Technologies Corporation | Transfection reagents |
| US7683035B1 (en) | 1999-02-23 | 2010-03-23 | Qiagen, Gmbh | Method of stabilizing and/or isolating nucleic acids |
| US20030096414A1 (en) | 2001-03-27 | 2003-05-22 | Invitrogen Corporation | Culture medium for cell growth and transfection |
| US7906122B2 (en) | 2003-06-18 | 2011-03-15 | Yissum Research Development Company Of The Hebrew University Of Jersusalem | Sphingoid polyalkylamine conjugates for Hepatitis B virus vaccination |
| JP2006527763A (ja) * | 2003-06-18 | 2006-12-07 | イッスム・リサーチ・ディベロップメント・カンパニー・オブ・ザ・ヘブルー・ユニバーシティ・オブ・エルサレム | スフィンゴ脂質のポリアルキルアミン抱合体 |
| US20060211004A1 (en) | 2005-02-15 | 2006-09-21 | Ilsley Diane D | Methods and compositions for determining non-specific cytotoxicity of a transfection agent |
| WO2006110358A2 (en) * | 2005-04-01 | 2006-10-19 | Invitrogen Corporation | Methods and compositions for introducing biopolymers into cells |
| EP2366787B1 (en) | 2006-01-13 | 2019-12-11 | The Government Of The U.S.A, As Represented By The Secretary, Dept. Of Health And Human Services | Codon optimized IL-15 and IL-15R-Alpha genes for expression in mammalian cells |
| EP3434259A1 (en) | 2007-05-04 | 2019-01-30 | Marina Biotech, Inc. | Amino acid lipids and uses thereof |
| US20110212021A1 (en) | 2008-05-30 | 2011-09-01 | Slack Frank J | Targeted oligonucleotide compositions for modifying gene expression |
| CN104382853A (zh) | 2008-10-16 | 2015-03-04 | 玛瑞纳生物技术有限公司 | 基因沉默治疗剂的脂质体有效递送方法和组合物 |
| SI2506857T1 (en) | 2009-12-01 | 2018-08-31 | Translate Bio, Inc. | Delivery of mRNA for the enrichment of proteins and enzymes in human genetic diseases |
| WO2011106705A2 (en) | 2010-02-26 | 2011-09-01 | The Government Of The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services | Dna-protein vaccination protocols |
| WO2011120023A1 (en) | 2010-03-26 | 2011-09-29 | Marina Biotech, Inc. | Nucleic acid compounds for inhibiting survivin gene expression uses thereof |
| WO2011133584A2 (en) | 2010-04-19 | 2011-10-27 | Marina Biotech, Inc. | Nucleic acid compounds for inhibiting hras gene expression and uses thereof |
| WO2011139842A2 (en) | 2010-04-28 | 2011-11-10 | Marina Biotech, Inc. | Nucleic acid compounds for inhibiting fgfr3 gene expression and uses thereof |
| FR2964569B1 (fr) | 2010-09-10 | 2012-10-19 | Ct De Cooperation Internationale En Rech Agronomique Pour Le Dev Cirad | Nouveaux liposomes de vaccination genique |
| US8853377B2 (en) | 2010-11-30 | 2014-10-07 | Shire Human Genetic Therapies, Inc. | mRNA for use in treatment of human genetic diseases |
| EP2648706A4 (en) | 2010-12-06 | 2014-07-23 | Penn State Res Found | COMPOSITIONS AND METHODS RELATING TO PROLIFERATIVE DISEASES |
| KR20220025112A (ko) | 2011-06-08 | 2022-03-03 | 샤이어 휴먼 지네틱 테라피즈 인크. | Mrna 전달을 위한 지질 나노입자 조성물 및 방법 |
| ES2567091T3 (es) | 2012-04-05 | 2016-04-19 | F. Hoffmann-La Roche Ag | Compuestos de amina para la preparación selectiva de muestras biológicas |
| EP3536787A1 (en) | 2012-06-08 | 2019-09-11 | Translate Bio, Inc. | Nuclease resistant polynucleotides and uses thereof |
| EA201591229A1 (ru) | 2013-03-14 | 2016-01-29 | Шир Хьюман Дженетик Терапис, Инк. | Способы очистки матричной рнк |
| KR102311614B1 (ko) | 2013-03-14 | 2021-10-08 | 샤이어 휴먼 지네틱 테라피즈 인크. | Cftr mrna 조성물 및 관련 방법 및 사용 |
| CA2905649A1 (en) | 2013-03-15 | 2014-09-18 | The Penn State Research Foundation | Compositions and methods including celecoxib and plumbagin relating to treatment of cancer |
| EP2968216A1 (en) | 2013-03-15 | 2016-01-20 | The Penn State Research Foundation | Compositions and methods including leelamine and arachidonyl trifluoromethyl ketone relating to treatment of cancer |
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| US3966630A (en) * | 1972-03-24 | 1976-06-29 | Petrolite Corporation | Use of polyquaternary ammonium methylene phosphonates in chelating or scale inhibition |
| US4022833A (en) * | 1973-02-14 | 1977-05-10 | Sterling Drug Inc. | N,N'-bridged-bis[2-alkyl-2-hydroxyethylamines] |
| US5733572A (en) * | 1989-12-22 | 1998-03-31 | Imarx Pharmaceutical Corp. | Gas and gaseous precursor filled microspheres as topical and subcutaneous delivery vehicles |
| US5220454A (en) * | 1990-03-30 | 1993-06-15 | Nikon Corporation | Cata-dioptric reduction projection optical system |
| US5283185A (en) * | 1991-08-28 | 1994-02-01 | University Of Tennessee Research Corporation | Method for delivering nucleic acids into cells |
| DE19505368A1 (de) * | 1995-02-17 | 1996-08-22 | Huels Chemische Werke Ag | Amphiphile Verbindungen mit mindestens zwei hydrophilen und mindestens zwei hydrophoben Gruppen auf der Basis von Dicarbonsäurediamiden |
| JPH11504631A (ja) * | 1995-04-25 | 1999-04-27 | バイカル インコーポレイテッド | Ｄｎａ／脂質複合体の単一バイアル製剤 |
| US5744335A (en) * | 1995-09-19 | 1998-04-28 | Mirus Corporation | Process of transfecting a cell with a polynucleotide mixed with an amphipathic compound and a DNA-binding protein |
| US5780448A (en) * | 1995-11-07 | 1998-07-14 | Ottawa Civic Hospital Loeb Research | DNA-based vaccination of fish |
| AU738384B2 (en) * | 1996-11-04 | 2001-09-20 | Qiagen Gmbh | Cationic reagents for transfection |
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- 1997-11-03 JP JP52084398A patent/JP4175667B2/ja not_active Expired - Lifetime
- 1997-11-03 DE DE69735382T patent/DE69735382T2/de not_active Expired - Lifetime
- 1997-11-03 EP EP97950064A patent/EP1003556B1/en not_active Expired - Lifetime
- 1997-11-03 CA CA002270396A patent/CA2270396C/en not_active Expired - Lifetime
- 1997-11-03 WO PCT/EP1997/006035 patent/WO1998019709A2/en not_active Ceased
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| AU738384B2 (en) | 2001-09-20 |
| WO1998019709A3 (en) | 1998-07-30 |
| DE69735382D1 (de) | 2006-04-27 |
| DE69735382T2 (de) | 2006-11-30 |
| US20040077582A1 (en) | 2004-04-22 |
| EP1003556B1 (en) | 2006-03-01 |
| JP2001503751A (ja) | 2001-03-21 |
| EP1003556A2 (en) | 2000-05-31 |
| AU5315698A (en) | 1998-05-29 |
| CA2270396A1 (en) | 1998-05-14 |
| US20010048939A1 (en) | 2001-12-06 |
| WO1998019709A2 (en) | 1998-05-14 |
| US6733777B2 (en) | 2004-05-11 |
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