CA2270396C - Cationic reagents for transfection - Google Patents
Cationic reagents for transfection Download PDFInfo
- Publication number
- CA2270396C CA2270396C CA002270396A CA2270396A CA2270396C CA 2270396 C CA2270396 C CA 2270396C CA 002270396 A CA002270396 A CA 002270396A CA 2270396 A CA2270396 A CA 2270396A CA 2270396 C CA2270396 C CA 2270396C
- Authority
- CA
- Canada
- Prior art keywords
- denotes
- chained
- straight
- alkyl
- dna
- 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 abstract description 66
- 125000002091 cationic group Chemical group 0.000 title abstract description 24
- 239000003153 chemical reaction reagent Substances 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 92
- 239000002502 liposome Substances 0.000 claims abstract description 80
- 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 claims abstract description 40
- 150000002632 lipids Chemical class 0.000 claims abstract description 27
- 238000000338 in vitro Methods 0.000 claims abstract description 19
- 238000001727 in vivo Methods 0.000 claims abstract description 12
- 230000007935 neutral effect Effects 0.000 claims abstract description 11
- 210000004027 cell Anatomy 0.000 claims description 68
- 108020004414 DNA Proteins 0.000 claims description 46
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 14
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 claims description 13
- 239000013612 plasmid Substances 0.000 claims description 12
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 10
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 10
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 claims description 10
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 7
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 7
- 150000001450 anions Chemical class 0.000 claims description 7
- 230000008685 targeting Effects 0.000 claims description 7
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
- 108091034117 Oligonucleotide Proteins 0.000 claims description 6
- 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 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
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- SNKAWJBJQDLSFF-NVKMUCNASA-N 1,2-dioleoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCC SNKAWJBJQDLSFF-NVKMUCNASA-N 0.000 claims 2
- 101100283604 Caenorhabditis elegans pigk-1 gene Proteins 0.000 claims 2
- 102000053602 DNA Human genes 0.000 claims 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims 2
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- YWWNNLPSZSEZNZ-UHFFFAOYSA-N n,n-dimethyldecan-1-amine Chemical compound CCCCCCCCCCN(C)C YWWNNLPSZSEZNZ-UHFFFAOYSA-N 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
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 101000600434 Homo sapiens Putative uncharacterized protein encoded by MIR7-3HG Proteins 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
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Classifications
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- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- 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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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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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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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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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- A61K9/127—Synthetic bilayered vehicles, e.g. liposomes or liposomes with cholesterol as the only non-phosphatidyl surfactant
- A61K9/1271—Non-conventional liposomes, e.g. PEGylated liposomes or liposomes coated or grafted with polymers
- A61K9/1272—Non-conventional liposomes, e.g. PEGylated liposomes or liposomes coated or grafted with polymers comprising non-phosphatidyl surfactants as bilayer-forming substances, e.g. cationic lipids or non-phosphatidyl liposomes coated or grafted with polymers
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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
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
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- Pharmacology & Pharmacy (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 (2)
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| CA2270396A1 CA2270396A1 (en) | 1998-05-14 |
| CA2270396C true CA2270396C (en) | 2008-03-11 |
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|---|---|---|---|
| CA002270396A Expired - Lifetime CA2270396C (en) | 1996-11-04 | 1997-11-03 | Cationic reagents for transfection |
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| 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 |
| EP3574923A1 (en) | 2013-10-22 | 2019-12-04 | Translate Bio, Inc. | Mrna therapy for phenylketonuria |
| ES2707966T3 (es) | 2013-10-22 | 2019-04-08 | Translate Bio Inc | Terapia de ARNm para la deficiencia en síntesis de argininosuccinato |
| EP4729528A3 (en) | 2014-04-25 | 2026-06-24 | Translate Bio, Inc. | Methods for purification of messenger rna |
| US10195280B2 (en) | 2014-07-15 | 2019-02-05 | Life Technologies Corporation | Compositions and methods for efficient delivery of molecules to cells |
| MX2019010155A (es) | 2017-02-27 | 2020-12-10 | Translate Bio Inc | Arnm de cftr optimizado por codón novedoso. |
| IL270631B2 (en) | 2017-05-16 | 2024-03-01 | Translate Bio Inc | Treatment of cystic fibrosis by delivery of codon-optimized mrna encoding cftr |
| US11174500B2 (en) | 2018-08-24 | 2021-11-16 | Translate Bio, Inc. | Methods for purification of messenger RNA |
| AU2019384557B2 (en) | 2018-11-21 | 2025-07-17 | Translate Bio, Inc. | Treatment of cystic fibrosis by delivery of nebulized mRNA encoding CFTR |
| US20220175723A1 (en) | 2019-04-22 | 2022-06-09 | The Penn State Research Foundation | Methods and compositions relating to inhibition of aldehyde dehydrogenases for treatment of cancer |
| CA3155003A1 (en) | 2019-09-20 | 2021-03-25 | Translate Bio, Inc. | Mrna encoding engineered cftr |
| US12616678B2 (en) | 2020-06-10 | 2026-05-05 | The Penn State Research Foundation | Methods to of aldehyde dehydrogenases for treatment of cancer |
| CN114656422B (zh) * | 2022-04-22 | 2023-05-23 | 重庆理工大学 | 一种新型氮杂冠醚化合物及其阳离子脂质体、制备方法与应用 |
| CN119301272A (zh) | 2022-06-02 | 2025-01-10 | 瑞孚迪健康科学公司 | 腺相关病毒衣壳的dna含量的电泳介导的表征 |
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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 |
-
1997
- 1997-11-03 AU AU53156/98A patent/AU738384B2/en not_active Expired
- 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
-
1999
- 1999-05-04 US US09/304,995 patent/US6733777B2/en not_active Expired - Lifetime
-
2003
- 2003-11-25 US US10/721,532 patent/US20040077582A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| AU738384B2 (en) | 2001-09-20 |
| WO1998019709A3 (en) | 1998-07-30 |
| JP4175667B2 (ja) | 2008-11-05 |
| 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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