CA2694610A1 - Method for manufacturing linear polyethylenimine (pei) for transfection purpose and linear pei obtained with such method - Google Patents
Method for manufacturing linear polyethylenimine (pei) for transfection purpose and linear pei obtained with such method Download PDFInfo
- Publication number
- CA2694610A1 CA2694610A1 CA2694610A CA2694610A CA2694610A1 CA 2694610 A1 CA2694610 A1 CA 2694610A1 CA 2694610 A CA2694610 A CA 2694610A CA 2694610 A CA2694610 A CA 2694610A CA 2694610 A1 CA2694610 A1 CA 2694610A1
- Authority
- CA
- Canada
- Prior art keywords
- peox
- monomer
- pei
- oxazoline
- linear
- 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.)
- Abandoned
Links
- 229920002873 Polyethylenimine Polymers 0.000 title claims abstract description 101
- 238000000034 method Methods 0.000 title claims abstract description 54
- 238000001890 transfection Methods 0.000 title claims abstract description 22
- 238000004519 manufacturing process Methods 0.000 title description 17
- 229920006187 aquazol Polymers 0.000 claims abstract description 77
- 239000012861 aquazol Substances 0.000 claims abstract description 77
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 66
- 239000000178 monomer Substances 0.000 claims abstract description 58
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 35
- 239000002904 solvent Substances 0.000 claims abstract description 33
- 238000005227 gel permeation chromatography Methods 0.000 claims abstract description 22
- 239000003999 initiator Substances 0.000 claims abstract description 21
- 229920000642 polymer Polymers 0.000 claims abstract description 19
- 238000006243 chemical reaction Methods 0.000 claims abstract description 18
- 238000005160 1H NMR spectroscopy Methods 0.000 claims abstract description 17
- NYEZZYQZRQDLEH-UHFFFAOYSA-N 2-ethyl-4,5-dihydro-1,3-oxazole Chemical compound CCC1=NCCO1 NYEZZYQZRQDLEH-UHFFFAOYSA-N 0.000 claims abstract description 17
- 238000012360 testing method Methods 0.000 claims abstract description 15
- 238000001914 filtration Methods 0.000 claims abstract description 14
- 238000001035 drying Methods 0.000 claims abstract description 11
- 238000001704 evaporation Methods 0.000 claims abstract description 8
- 230000008020 evaporation Effects 0.000 claims abstract description 8
- 238000005406 washing Methods 0.000 claims abstract description 7
- 238000012790 confirmation Methods 0.000 claims abstract description 6
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract description 5
- 238000001556 precipitation Methods 0.000 claims abstract description 5
- 238000002156 mixing Methods 0.000 claims abstract description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- -1 poly(2-ethyl-2-oxazoline) Polymers 0.000 claims description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 20
- 235000019260 propionic acid Nutrition 0.000 claims description 13
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 13
- 230000008569 process Effects 0.000 claims description 10
- 238000000746 purification Methods 0.000 claims description 8
- 239000012528 membrane Substances 0.000 claims description 5
- 238000010533 azeotropic distillation Methods 0.000 claims description 4
- 238000004108 freeze drying Methods 0.000 claims description 4
- 239000013067 intermediate product Substances 0.000 claims description 4
- 238000012544 monitoring process Methods 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 229920002301 cellulose acetate Polymers 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 238000003556 assay Methods 0.000 description 23
- 210000004027 cell Anatomy 0.000 description 14
- 238000006116 polymerization reaction Methods 0.000 description 13
- 238000004821 distillation Methods 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 9
- 239000002158 endotoxin Substances 0.000 description 9
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 9
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 7
- 239000012535 impurity Substances 0.000 description 7
- 238000001727 in vivo Methods 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 229960004132 diethyl ether Drugs 0.000 description 6
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 238000000569 multi-angle light scattering Methods 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 239000013612 plasmid Substances 0.000 description 4
- 229920000765 poly(2-oxazolines) Polymers 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 238000010626 work up procedure Methods 0.000 description 4
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 238000000149 argon plasma sintering Methods 0.000 description 3
- 238000011049 filling Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 101150041968 CDC13 gene Proteins 0.000 description 2
- 208000034628 Celiac artery compression syndrome Diseases 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 108060001084 Luciferase Proteins 0.000 description 2
- 102000016611 Proteoglycans Human genes 0.000 description 2
- 108010067787 Proteoglycans Proteins 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 241000700605 Viruses Species 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- 230000001464 adherent effect Effects 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000010923 batch production Methods 0.000 description 2
- BBWBEZAMXFGUGK-UHFFFAOYSA-N bis(dodecylsulfanyl)-methylarsane Chemical compound CCCCCCCCCCCCS[As](C)SCCCCCCCCCCCC BBWBEZAMXFGUGK-UHFFFAOYSA-N 0.000 description 2
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 2
- 238000004113 cell culture Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000003365 glass fiber Substances 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 230000036512 infertility Effects 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 239000006166 lysate Substances 0.000 description 2
- 239000012139 lysis buffer Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000013641 positive control Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000003908 quality control method Methods 0.000 description 2
- 238000012372 quality testing Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000004611 spectroscopical analysis Methods 0.000 description 2
- 239000008223 sterile water Substances 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- JHALWMSZGCVVEM-UHFFFAOYSA-N 2-[4,7-bis(carboxymethyl)-1,4,7-triazonan-1-yl]acetic acid Chemical compound OC(=O)CN1CCN(CC(O)=O)CCN(CC(O)=O)CC1 JHALWMSZGCVVEM-UHFFFAOYSA-N 0.000 description 1
- 125000003504 2-oxazolinyl group Chemical group O1C(=NCC1)* 0.000 description 1
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- IGXWBGJHJZYPQS-SSDOTTSWSA-N D-Luciferin Chemical compound OC(=O)[C@H]1CSC(C=2SC3=CC=C(O)C=C3N=2)=N1 IGXWBGJHJZYPQS-SSDOTTSWSA-N 0.000 description 1
- CYCGRDQQIOGCKX-UHFFFAOYSA-N Dehydro-luciferin Natural products OC(=O)C1=CSC(C=2SC3=CC(O)=CC=C3N=2)=N1 CYCGRDQQIOGCKX-UHFFFAOYSA-N 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- BJGNCJDXODQBOB-UHFFFAOYSA-N Fivefly Luciferin Natural products OC(=O)C1CSC(C=2SC3=CC(O)=CC=C3N=2)=N1 BJGNCJDXODQBOB-UHFFFAOYSA-N 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- 241000239218 Limulus Species 0.000 description 1
- 239000005089 Luciferase Substances 0.000 description 1
- DDWFXDSYGUXRAY-UHFFFAOYSA-N Luciferin Natural products CCc1c(C)c(CC2NC(=O)C(=C2C=C)C)[nH]c1Cc3[nH]c4C(=C5/NC(CC(=O)O)C(C)C5CC(=O)O)CC(=O)c4c3C DDWFXDSYGUXRAY-UHFFFAOYSA-N 0.000 description 1
- 108091034117 Oligonucleotide Proteins 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical group C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 239000004614 Process Aid Substances 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 241000607142 Salmonella Species 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 230000001668 ameliorated effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000011213 bioburden testing Methods 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- 239000008364 bulk solution Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 238000012656 cationic ring opening polymerization Methods 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000001332 colony forming effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 210000000805 cytoplasm Anatomy 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000005293 duran Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012039 electrophile Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000012202 endocytosis Effects 0.000 description 1
- 210000001163 endosome Anatomy 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012909 foetal bovine serum Substances 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
- 238000012988 high-throughput synthesis Methods 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000013339 in-process testing Methods 0.000 description 1
- 230000004941 influx Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 238000010552 living cationic polymerization reaction Methods 0.000 description 1
- 238000003670 luciferase enzyme activity assay Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 230000003278 mimic effect Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 238000013148 permeation assay Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000010966 qNMR Methods 0.000 description 1
- 238000000275 quality assurance Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 238000011146 sterile filtration Methods 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/0233—Polyamines derived from (poly)oxazolines, (poly)oxazines or having pendant acyl groups
-
- C—CHEMISTRY; METALLURGY
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Genetics & Genomics (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Wood Science & Technology (AREA)
- General Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Zoology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biophysics (AREA)
- Microbiology (AREA)
- Plant Pathology (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US95299307P | 2007-07-31 | 2007-07-31 | |
| US60/952,993 | 2007-07-31 | ||
| PCT/IB2008/002339 WO2009016507A2 (en) | 2007-07-31 | 2008-07-31 | Method for manufacturing linear polyethylenimine (pei) for transfection purpose and linear pei obtained with such method |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2694610A1 true CA2694610A1 (en) | 2009-02-05 |
Family
ID=40304983
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2694610A Abandoned CA2694610A1 (en) | 2007-07-31 | 2008-07-31 | Method for manufacturing linear polyethylenimine (pei) for transfection purpose and linear pei obtained with such method |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20100197888A1 (https=) |
| EP (1) | EP2183297A2 (https=) |
| JP (1) | JP2010535264A (https=) |
| KR (1) | KR20100050523A (https=) |
| CN (1) | CN101821317A (https=) |
| CA (1) | CA2694610A1 (https=) |
| WO (1) | WO2009016507A2 (https=) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2464388B1 (en) * | 2009-08-11 | 2017-05-10 | Agency for Science, Technology and Research | Particulate hyaluronic acid formulations for cellular delivery of bioactive agents |
| CA2851617A1 (en) | 2011-10-14 | 2013-04-18 | University Of Georgia Research Foundation, Inc. | Synthesis and application reactive antimicrobial copolymers for textile fibers |
| CN102399267B (zh) * | 2011-11-22 | 2013-06-12 | 上海海洋大学 | 一种双功能肽修饰的基因载体及其制备方法 |
| ES2919864T3 (es) | 2012-10-05 | 2022-07-28 | Biontech Delivery Tech Gmbh | Derivados de poliamina hidroxilada como reactivos de transfección |
| CN112370532B (zh) | 2012-10-08 | 2024-11-01 | 生物技术传送科技有限责任公司 | 作为转染试剂的羧化多胺衍生物 |
| US8909530B2 (en) | 2013-03-15 | 2014-12-09 | Orcam Technologies Ltd. | Apparatus, method, and computer readable medium for expedited text reading using staged OCR technique |
| JP6765363B2 (ja) * | 2014-07-11 | 2020-10-07 | ジェンザイム・コーポレーション | 主鎖ポリアミン |
| EP3204442B1 (en) | 2014-07-18 | 2018-09-12 | Universiteit Gent | Method for the preparation of uniform, high molar mass cyclic imino ether polymers |
| CN106832270A (zh) * | 2017-01-18 | 2017-06-13 | 南京工业大学 | 一种聚（2‑r‑噁唑啉）嵌段聚（乙撑亚胺）的制备方法 |
| CN109794175A (zh) * | 2018-12-26 | 2019-05-24 | 浙江大学 | 具有pH响应性的氧化石墨烯复合膜及其制备方法和用途 |
| US11559477B2 (en) | 2019-03-01 | 2023-01-24 | Shanghai Cheermore Biological Technology Co., Ltd. | Preparation method and use of artificial exosome complex |
| CN110638690B (zh) * | 2019-03-01 | 2021-06-04 | 上海澄穆生物科技有限公司 | 一种人工外泌体复合物的制备方法及应用 |
| IT202000012055A1 (it) | 2020-05-22 | 2021-11-22 | Milano Politecnico | Dispositivo, metodo e composizione per la trasfezione di cellule con acidi nucleici |
| US11879031B2 (en) * | 2020-10-22 | 2024-01-23 | Solenis Technologies, L.P. | Low critical solution temperature purification of oxazoline polymer solutions |
| IT202100000149A1 (it) * | 2021-01-05 | 2022-07-05 | Themis S R L | Sistema e metodo per il tracciamento e per garantire la qualità di materie prime |
| ES2989849T3 (es) * | 2022-02-25 | 2024-11-27 | Polyplus Transfection | Métodos de purificación, detección y cuantificación de reactivos de transfección residuales basados en PEI |
| CN116854908B (zh) * | 2023-07-10 | 2026-02-13 | 中国科学院长春应用化学研究所 | 一种阳离子聚合物、其制备方法及应用 |
Family Cites Families (13)
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|---|---|---|---|---|
| US3640909A (en) * | 1969-02-17 | 1972-02-08 | Dow Chemical Co | Substituted acylated polyimine resins |
| JPS5223000B2 (https=) * | 1971-08-21 | 1977-06-21 | ||
| US4857599A (en) * | 1988-02-08 | 1989-08-15 | The Dow Chemical Company | Modified dense star polymers |
| JPH02255725A (ja) * | 1989-03-29 | 1990-10-16 | Kao Corp | ポリ（ｎ―アシルエチレンイミン）系重合体の製造方法 |
| US5017644A (en) * | 1989-05-22 | 1991-05-21 | Xerox Corporation | Ink jet ink compositions |
| US6025104A (en) * | 1992-07-29 | 2000-02-15 | Xerox Corporation | Toner and developer compositions with polyoxazoline resin particles |
| CA2226299A1 (en) * | 1995-08-11 | 1997-02-27 | Dendritech, Inc. | Hyper comb-branched polymer conjugates |
| DE19743135A1 (de) * | 1997-09-30 | 1999-04-01 | Hoechst Marion Roussel De Gmbh | Biologisch verträgliche niedermolekular Polyethylenimine |
| CA2395636A1 (en) * | 1999-12-30 | 2001-07-12 | Novartis Ag | Novel colloid synthetic vectors for gene therapy |
| CN1479632A (zh) * | 2000-10-09 | 2004-03-03 | 用于将核酸导入细胞的复合物 | |
| US20050038197A1 (en) * | 2003-08-13 | 2005-02-17 | Tomalia Donald A. | Ultra_high molecular weight hybrid dendrigraft architectures |
| WO2005075527A1 (en) * | 2004-01-30 | 2005-08-18 | The General Hospital Corporation | Hyperbranched polymers |
| WO2007084797A1 (en) * | 2006-01-23 | 2007-07-26 | Abbott Laboratories | Chemically modified polycation polymer for sirna delivery |
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2008
- 2008-07-31 JP JP2010518773A patent/JP2010535264A/ja active Pending
- 2008-07-31 CA CA2694610A patent/CA2694610A1/en not_active Abandoned
- 2008-07-31 WO PCT/IB2008/002339 patent/WO2009016507A2/en not_active Ceased
- 2008-07-31 CN CN200880104653A patent/CN101821317A/zh active Pending
- 2008-07-31 KR KR1020107004337A patent/KR20100050523A/ko not_active Withdrawn
- 2008-07-31 EP EP08807030A patent/EP2183297A2/en not_active Withdrawn
- 2008-07-31 US US12/671,312 patent/US20100197888A1/en not_active Abandoned
Also Published As
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|---|---|
| WO2009016507A2 (en) | 2009-02-05 |
| EP2183297A2 (en) | 2010-05-12 |
| CN101821317A (zh) | 2010-09-01 |
| KR20100050523A (ko) | 2010-05-13 |
| JP2010535264A (ja) | 2010-11-18 |
| WO2009016507A3 (en) | 2009-09-03 |
| US20100197888A1 (en) | 2010-08-05 |
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