JP2001515060A5 - - Google Patents
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- JP2001515060A5 JP2001515060A5 JP2000509683A JP2000509683A JP2001515060A5 JP 2001515060 A5 JP2001515060 A5 JP 2001515060A5 JP 2000509683 A JP2000509683 A JP 2000509683A JP 2000509683 A JP2000509683 A JP 2000509683A JP 2001515060 A5 JP2001515060 A5 JP 2001515060A5
- Authority
- JP
- Japan
- Prior art keywords
- dna
- embedded image
- lipid
- lipids
- liposome
- 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.)
- Granted
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- 239000000203 mixture Substances 0.000 description 17
- 150000002632 lipids Chemical class 0.000 description 13
- 238000009472 formulation Methods 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 10
- 239000002502 liposome Substances 0.000 description 10
- 108020004414 DNA Proteins 0.000 description 9
- 210000004027 cell Anatomy 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 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 description 4
- 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 4
- -1 hexadecenyl Chemical group 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 108091032973 (ribonucleotides)n+m Proteins 0.000 description 3
- 108020004491 Antisense DNA Proteins 0.000 description 3
- 101001007348 Arachis hypogaea Galactose-binding lectin Proteins 0.000 description 3
- 102000053642 Catalytic RNA Human genes 0.000 description 3
- 108090000994 Catalytic RNA Proteins 0.000 description 3
- 102000003886 Glycoproteins Human genes 0.000 description 3
- 108090000288 Glycoproteins Proteins 0.000 description 3
- 108010043958 Peptoids Proteins 0.000 description 3
- 239000003816 antisense DNA Substances 0.000 description 3
- 210000003527 eukaryotic cell Anatomy 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 239000000693 micelle Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 108090000765 processed proteins & peptides Proteins 0.000 description 3
- 102000004196 processed proteins & peptides Human genes 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 108091092562 ribozyme Proteins 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000001890 transfection Methods 0.000 description 3
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 2
- YGPZWPHDULZYFR-DPAQBDIFSA-N (3s,8s,9s,10r,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-amine Chemical compound C1C=C2C[C@@H](N)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 YGPZWPHDULZYFR-DPAQBDIFSA-N 0.000 description 2
- 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 description 2
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 235000012000 cholesterol Nutrition 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 239000008174 sterile solution Substances 0.000 description 2
- 239000012096 transfection reagent Substances 0.000 description 2
- RQOHILYYSYHRAR-UHFFFAOYSA-N 2,5-bis(3-aminopropylamino)-n-[2-(dioctadecylamino)ethyl]pentanamide Chemical compound CCCCCCCCCCCCCCCCCCN(CCNC(=O)C(CCCNCCCN)NCCCN)CCCCCCCCCCCCCCCCCC RQOHILYYSYHRAR-UHFFFAOYSA-N 0.000 description 1
- 102100033312 Alpha-2-macroglobulin Human genes 0.000 description 1
- 108010001857 Cell Surface Receptors Proteins 0.000 description 1
- 108010026206 Conalbumin Proteins 0.000 description 1
- NBSCHQHZLSJFNQ-QTVWNMPRSA-N D-Mannose-6-phosphate Chemical compound OC1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@@H]1O NBSCHQHZLSJFNQ-QTVWNMPRSA-N 0.000 description 1
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 102000004856 Lectins Human genes 0.000 description 1
- 108090001090 Lectins Proteins 0.000 description 1
- OVBPIULPVIDEAO-UHFFFAOYSA-N N-Pteroyl-L-glutaminsaeure Natural products C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-UHFFFAOYSA-N 0.000 description 1
- 108010039918 Polylysine Proteins 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 108010015078 Pregnancy-Associated alpha 2-Macroglobulins Proteins 0.000 description 1
- 102000011409 Transcobalamins Human genes 0.000 description 1
- 108010023603 Transcobalamins Proteins 0.000 description 1
- 102000004338 Transferrin Human genes 0.000 description 1
- 108090000901 Transferrin Proteins 0.000 description 1
- 238000005411 Van der Waals force Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000012062 aqueous buffer Substances 0.000 description 1
- 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 1
- 108010005774 beta-Galactosidase Proteins 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 229960000074 biopharmaceutical Drugs 0.000 description 1
- 229960002685 biotin Drugs 0.000 description 1
- 235000020958 biotin Nutrition 0.000 description 1
- 239000011616 biotin Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000005066 dodecenyl group Chemical group C(=CCCCCCCCCCC)* 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical class OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 description 1
- 229960000304 folic acid Drugs 0.000 description 1
- 235000019152 folic acid Nutrition 0.000 description 1
- 239000011724 folic acid Substances 0.000 description 1
- 229930182830 galactose Natural products 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 239000002523 lectin Substances 0.000 description 1
- 102000006240 membrane receptors Human genes 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- HWBABUFLTDQOQD-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-[2-(dioctadecylamino)ethyl]propane-1,3-diamine Chemical compound CCCCCCCCCCCCCCCCCCN(CCN(CCCN)CCCN)CCCCCCCCCCCCCCCCCC HWBABUFLTDQOQD-UHFFFAOYSA-N 0.000 description 1
- 125000005064 octadecenyl group Chemical group C(=CCCCCCCCCCCCCCCCC)* 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920000656 polylysine Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- PFNFFQXMRSDOHW-UHFFFAOYSA-N spermine Chemical group NCCCNCCCCNCCCN PFNFFQXMRSDOHW-UHFFFAOYSA-N 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000005063 tetradecenyl group Chemical group C(=CCCCCCCCCCCCC)* 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 239000012581 transferrin Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19735125.5 | 1997-08-13 | ||
| DE19735125 | 1997-08-13 | ||
| DE19834683A DE19834683A1 (de) | 1997-08-13 | 1998-07-31 | Neue Lipopolyamine, deren Darstellung und Anwendung |
| DE19834683.2 | 1998-07-31 | ||
| PCT/EP1998/005156 WO1999008997A1 (de) | 1997-08-13 | 1998-08-13 | Neue lipopolyamine, deren darstellung und anwendung |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2001515060A JP2001515060A (ja) | 2001-09-18 |
| JP2001515060A5 true JP2001515060A5 (enExample) | 2010-05-06 |
| JP4504559B2 JP4504559B2 (ja) | 2010-07-14 |
Family
ID=26039111
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000509683A Expired - Fee Related JP4504559B2 (ja) | 1997-08-13 | 1998-08-13 | 新リポポリアミン、その調製および適用 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6281371B1 (enExample) |
| EP (1) | EP1003711B1 (enExample) |
| JP (1) | JP4504559B2 (enExample) |
| AT (1) | ATE208369T1 (enExample) |
| AU (1) | AU745958B2 (enExample) |
| CA (1) | CA2299429C (enExample) |
| ES (1) | ES2167939T3 (enExample) |
| WO (1) | WO1999008997A1 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU768542C (en) | 1998-04-08 | 2004-06-17 | Celltech R & D Limited | Lipids |
| US6852334B1 (en) * | 1999-04-20 | 2005-02-08 | The University Of British Columbia | Cationic peg-lipids and methods of use |
| DE60035687T2 (de) * | 1999-04-26 | 2008-06-05 | Ucb Pharma, S.A. | Bipolare lipide und ihre verwendung zum transport bioaktiver substanzen |
| EP1237581A1 (en) * | 1999-12-17 | 2002-09-11 | Gene Therapy Systems, Inc. | Use of cationic lipids for intracellular protein delivery |
| US7189705B2 (en) | 2000-04-20 | 2007-03-13 | The University Of British Columbia | Methods of enhancing SPLP-mediated transfection using endosomal membrane destabilizers |
| US7294511B2 (en) * | 2001-03-22 | 2007-11-13 | Chromos Molecular Systems, Inc. | Methods for delivering nucleic acid molecules into cells and assessment thereof |
| US7001925B1 (en) | 2002-09-27 | 2006-02-21 | University Of Central Florida Research Foundation, Inc. | Compounds and method for enhancing the efficacy of anti-cancer drugs |
| EP1638610B1 (en) * | 2003-06-18 | 2015-03-18 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Sphingoid polyalkylamine conjugates for vaccination |
| 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 |
| US20110045001A1 (en) * | 2008-03-28 | 2011-02-24 | Biontex Laboratories Gmbh | Transfection results of non-viral gene delivery systems by influencing of the innate immune system |
| WO2013016058A1 (en) * | 2011-07-22 | 2013-01-31 | Merck Sharp & Dohme Corp. | Novel bis-nitrogen containing cationic lipids for oligonucleotide delivery |
| KR102647743B1 (ko) | 2014-11-10 | 2024-03-14 | 에트리스 게엠베하 | Bmp 인코딩 rna의 전달에 의한 골형성 유도 |
| CN113423418B (zh) | 2019-02-14 | 2025-01-10 | 埃泽瑞斯公司 | 纤毛疾病的治疗 |
| US20240181011A1 (en) | 2020-11-04 | 2024-06-06 | Ethris Gmbh | Use of ifn-lambda mrna for treating viral infections |
| WO2024121160A1 (en) | 2022-12-05 | 2024-06-13 | Ethris Gmbh | Regulator(s) of energy homeostasis-encoding rna molecule(s) with increased translation efficiency |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1963189A1 (de) | 1969-12-17 | 1971-06-24 | Bayer Ag | Verfahren zur Herstellung von flammfesten,Urethangruppen aufweisenden Schaumstoffen |
| US4339767A (en) | 1980-05-05 | 1982-07-13 | International Business Machines Corporation | High performance PNP and NPN transistor structure |
| DE69034078T2 (de) | 1989-03-21 | 2004-04-01 | Vical, Inc., San Diego | Expression von exogenen Polynukleotidsequenzen in Wirbeltieren |
| FR2645866B1 (fr) * | 1989-04-17 | 1991-07-05 | Centre Nat Rech Scient | Nouvelles lipopolyamines, leur preparation et leur emploi |
| US5538722A (en) | 1989-06-13 | 1996-07-23 | Stanford University | Isolation, growth, differentiation and genetic engineering of human muscle cells |
| US5264618A (en) | 1990-04-19 | 1993-11-23 | Vical, Inc. | Cationic lipids for intracellular delivery of biologically active molecules |
| IL103059A0 (en) | 1991-09-30 | 1993-02-21 | Boehringer Ingelheim Int | Conjugates for introducing nucleic acid into higher eucaryotic cells |
| DE4139001A1 (de) * | 1991-11-27 | 1993-06-03 | Boehringer Mannheim Gmbh | Verfahren zur einschleusung von nukleinsaeuren in zellen |
| US5972600A (en) | 1992-04-03 | 1999-10-26 | The Regents Of The University Of California | Separation of active complexes |
| US5334761A (en) * | 1992-08-28 | 1994-08-02 | Life Technologies, Inc. | Cationic lipids |
| GB9218762D0 (en) | 1992-09-04 | 1992-10-21 | Exxon Chemical Patents Inc | Esters |
| CN1119459A (zh) | 1993-03-19 | 1996-03-27 | 柏伦格-英格尔海姆国际股份公司 | 肿瘤疫苗的制备方法 |
| US5777153A (en) | 1994-07-08 | 1998-07-07 | Gilead Sciences, Inc. | Cationic lipids |
| US5939401A (en) | 1994-12-09 | 1999-08-17 | Genzyme Corporation | Cationic amphiphile compositions for intracellular delivery of therapeutic molecules |
| US6071890A (en) | 1994-12-09 | 2000-06-06 | Genzyme Corporation | Organ-specific targeting of cationic amphiphile/DNA complexes for gene therapy |
| US5650096A (en) * | 1994-12-09 | 1997-07-22 | Genzyme Corporation | Cationic amphiphiles for intracellular delivery of therapeutic molecules |
| JPH11507815A (ja) | 1995-06-07 | 1999-07-13 | ジンタ・インコーポレイテッド | ホスホン酸基本カチオン性脂質 |
| US5811406A (en) | 1995-06-07 | 1998-09-22 | Regents Of The University Of California | Dry powder formulations of polynucleotide complexes |
| EP0833667A4 (en) | 1995-06-07 | 2001-11-21 | Univ California | STABILIZATION OF POLYNUCLEOTIDE COMPLEXES |
| JPH11507352A (ja) | 1995-06-07 | 1999-06-29 | ジンタ・インコーポレイテッド | 新規カルバメート基本カチオン性脂質 |
| DE19521412A1 (de) * | 1995-06-14 | 1996-12-19 | Boehringer Mannheim Gmbh | Neue kationische und polykationische Amphiphile, diese enthaltende Reagenzien und deren Verwendung |
| EP0869937A4 (en) | 1995-07-21 | 2004-07-21 | Promega Biosciences Inc | AMID BASED CATIONIC LIPIDS |
| DE19607686A1 (de) | 1996-02-29 | 1997-09-04 | Chemicon Lab Gmbh | Neue metabolisierbare Lipopolyamine, deren Darstellung und Anwendung |
| US5747509A (en) | 1996-06-03 | 1998-05-05 | Schering Aktiengesellschaft | Method for lowering plasma levels of lipoprotein(a) |
-
1998
- 1998-08-13 CA CA2299429A patent/CA2299429C/en not_active Expired - Fee Related
- 1998-08-13 EP EP98946333A patent/EP1003711B1/de not_active Expired - Lifetime
- 1998-08-13 WO PCT/EP1998/005156 patent/WO1999008997A1/de not_active Ceased
- 1998-08-13 US US09/463,172 patent/US6281371B1/en not_active Expired - Lifetime
- 1998-08-13 JP JP2000509683A patent/JP4504559B2/ja not_active Expired - Fee Related
- 1998-08-13 ES ES98946333T patent/ES2167939T3/es not_active Expired - Lifetime
- 1998-08-13 AT AT98946333T patent/ATE208369T1/de not_active IP Right Cessation
- 1998-08-13 AU AU93421/98A patent/AU745958B2/en not_active Ceased
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