DE102013016750A1 - Neue Poly(ethylenimin) basierte Copolymere zur Anbindung und Freisetzung von genetischem Material, insbesondere von DNA/RNA, sowie Verfahren zu deren Herstellung und Verwendung - Google Patents
Neue Poly(ethylenimin) basierte Copolymere zur Anbindung und Freisetzung von genetischem Material, insbesondere von DNA/RNA, sowie Verfahren zu deren Herstellung und Verwendung Download PDFInfo
- Publication number
- DE102013016750A1 DE102013016750A1 DE102013016750.7A DE102013016750A DE102013016750A1 DE 102013016750 A1 DE102013016750 A1 DE 102013016750A1 DE 102013016750 A DE102013016750 A DE 102013016750A DE 102013016750 A1 DE102013016750 A1 DE 102013016750A1
- Authority
- DE
- Germany
- Prior art keywords
- ethyleneimine
- release
- genetic material
- based copolymers
- units
- 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.)
- Pending
Links
- 229920001577 copolymer Polymers 0.000 title claims abstract description 55
- 108090000623 proteins and genes Proteins 0.000 title claims abstract description 24
- 102000004169 proteins and genes Human genes 0.000 title claims abstract description 23
- 229920002873 Polyethylenimine Polymers 0.000 title claims description 40
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 5
- 230000027455 binding Effects 0.000 claims abstract description 23
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 15
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 3
- 239000000017 hydrogel Substances 0.000 claims description 36
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 20
- 238000007306 functionalization reaction Methods 0.000 claims description 15
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims description 10
- 125000003504 2-oxazolinyl group Chemical group O1C(=NCC1)* 0.000 claims description 10
- 239000011324 bead Substances 0.000 claims description 9
- 125000000524 functional group Chemical group 0.000 claims description 6
- 239000000178 monomer Substances 0.000 claims description 6
- 239000002245 particle Substances 0.000 claims description 5
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 239000000758 substrate Substances 0.000 claims description 3
- 150000008065 acid anhydrides Chemical class 0.000 claims description 2
- 230000003213 activating effect Effects 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- 239000000470 constituent Substances 0.000 claims 1
- 108091032973 (ribonucleotides)n+m Proteins 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- OXBLVCZKDOZZOJ-UHFFFAOYSA-N 2,3-Dihydrothiophene Chemical compound C1CC=CS1 OXBLVCZKDOZZOJ-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 238000004132 cross linking Methods 0.000 description 6
- 239000000499 gel Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- HCZMHWVFVZAHCR-UHFFFAOYSA-N 2-[2-(2-sulfanylethoxy)ethoxy]ethanethiol Chemical compound SCCOCCOCCS HCZMHWVFVZAHCR-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 150000004662 dithiols Chemical class 0.000 description 4
- VYYANIUXTTXFJR-UHFFFAOYSA-N 2-but-3-enyl-4,5-dihydro-1,3-oxazole Chemical compound C=CCCC1=NCCO1 VYYANIUXTTXFJR-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 239000004971 Cross linker Substances 0.000 description 3
- 230000004568 DNA-binding Effects 0.000 description 3
- 238000006845 Michael addition reaction Methods 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- -1 aminoacyl esters Chemical class 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000013612 plasmid Substances 0.000 description 3
- 229920000765 poly(2-oxazolines) Polymers 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 2
- GVJXGCIPWAVXJP-UHFFFAOYSA-N 2,5-dioxo-1-oxoniopyrrolidine-3-sulfonate Chemical compound ON1C(=O)CC(S(O)(=O)=O)C1=O GVJXGCIPWAVXJP-UHFFFAOYSA-N 0.000 description 2
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 241000252203 Clupea harengus Species 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical group OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 2
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 2
- 230000021736 acetylation Effects 0.000 description 2
- 238000006640 acetylation reaction Methods 0.000 description 2
- 230000001588 bifunctional effect Effects 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 229960005542 ethidium bromide Drugs 0.000 description 2
- 229960002897 heparin Drugs 0.000 description 2
- 229920000669 heparin Polymers 0.000 description 2
- 235000019514 herring Nutrition 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000001404 mediated effect Effects 0.000 description 2
- PSGAAPLEWMOORI-PEINSRQWSA-N medroxyprogesterone acetate Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](OC(C)=O)(C(C)=O)CC[C@H]21 PSGAAPLEWMOORI-PEINSRQWSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000003141 primary amines Chemical group 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000006557 surface reaction Methods 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- BUHVIAUBTBOHAG-FOYDDCNASA-N (2r,3r,4s,5r)-2-[6-[[2-(3,5-dimethoxyphenyl)-2-(2-methylphenyl)ethyl]amino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound COC1=CC(OC)=CC(C(CNC=2C=3N=CN(C=3N=CN=2)[C@H]2[C@@H]([C@H](O)[C@@H](CO)O2)O)C=2C(=CC=CC=2)C)=C1 BUHVIAUBTBOHAG-FOYDDCNASA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- ONRREFWJTRBDRA-UHFFFAOYSA-N 2-chloroethanamine;hydron;chloride Chemical compound [Cl-].[NH3+]CCCl ONRREFWJTRBDRA-UHFFFAOYSA-N 0.000 description 1
- GUXJXWKCUUWCLX-UHFFFAOYSA-N 2-methyl-2-oxazoline Chemical class CC1=NCCO1 GUXJXWKCUUWCLX-UHFFFAOYSA-N 0.000 description 1
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 238000000018 DNA microarray Methods 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 108020004459 Small interfering RNA Proteins 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000000266 alpha-aminoacyl group Chemical group 0.000 description 1
- 230000009435 amidation Effects 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 230000003373 anti-fouling effect Effects 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 235000019688 fish Nutrition 0.000 description 1
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 1
- 238000000799 fluorescence microscopy Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 238000001476 gene delivery Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 210000004962 mammalian cell Anatomy 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000813 microcontact printing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- QNILTEGFHQSKFF-UHFFFAOYSA-N n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)C=C QNILTEGFHQSKFF-UHFFFAOYSA-N 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 238000010943 off-gassing Methods 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000001890 transfection Methods 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 229920003169 water-soluble polymer Polymers 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
- C08G73/0206—Polyalkylene(poly)amines
-
- 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
- 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
- C08G73/0206—Polyalkylene(poly)amines
- C08G73/0213—Preparatory process
-
- 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
- C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102013016750.7A DE102013016750A1 (de) | 2013-10-02 | 2013-10-02 | Neue Poly(ethylenimin) basierte Copolymere zur Anbindung und Freisetzung von genetischem Material, insbesondere von DNA/RNA, sowie Verfahren zu deren Herstellung und Verwendung |
| CA2926154A CA2926154C (en) | 2013-10-02 | 2014-10-02 | New poly(ethylene imine)-based copolymers for bonding to and releasing genetic material, in particular dna/rna, and method for the production and use of same |
| JP2016519856A JP6431533B2 (ja) | 2013-10-02 | 2014-10-02 | 遺伝物質、特にｄｎａ／ｒｎａへの結合及びその放出のための新規ポリ（エチレンイミン）系コポリマー、並びに該コポリマーの製造方法及び使用 |
| CN201480059919.6A CN105683256B (zh) | 2013-10-02 | 2014-10-02 | 用于连接和释放遗传物质，特别是dna/rna，的新型聚乙烯亚胺‑基共聚物及其制备方法和用途 |
| US15/026,882 US10131747B2 (en) | 2013-10-02 | 2014-10-02 | Poly(ethylene imine)-based copolymers for bonding to and releasing genetic material, in particular DNA/RNA, and method for the production and use of same |
| DK14803038.0T DK3052545T3 (en) | 2013-10-02 | 2014-10-02 | New poly (ethyleneimine) -based copolymers for binding to and releasing genetic material, especially DNA / RNA, and methods for their preparation and use |
| ES14803038.0T ES2691094T3 (es) | 2013-10-02 | 2014-10-02 | Nuevos copolímeros basados en poli(etilenimina) para el enlace y liberación de material genético, particularmente de ADN/ARN, así como método para su fabricación y uso |
| PCT/DE2014/000500 WO2015048940A1 (de) | 2013-10-02 | 2014-10-02 | Neue poly(ethylenimin) basierte copolymere zur anbindung und freisetzung von genetischem material, insbesondere von dna/rna, sowie verfahren zu deren herstellung und verwendung |
| EP14803038.0A EP3052545B1 (de) | 2013-10-02 | 2014-10-02 | Neue poly(ethylenimin) basierte copolymere zur anbindung und freisetzung von genetischem material, insbesondere von dna/rna, sowie verfahren zu deren herstellung und verwendung |
| HUE14803038A HUE040402T2 (hu) | 2013-10-02 | 2014-10-02 | Új poli(etilénimin) alapú kopolimerek kötésre genetikai anyaghoz, elsõsorban DNS/RNS-hez, és annak elbocsátásához, és eljárás ezen kopolimerek elõállítására és alkalmazására |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102013016750.7A DE102013016750A1 (de) | 2013-10-02 | 2013-10-02 | Neue Poly(ethylenimin) basierte Copolymere zur Anbindung und Freisetzung von genetischem Material, insbesondere von DNA/RNA, sowie Verfahren zu deren Herstellung und Verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE102013016750A1 true DE102013016750A1 (de) | 2015-04-02 |
Family
ID=51986963
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE102013016750.7A Pending DE102013016750A1 (de) | 2013-10-02 | 2013-10-02 | Neue Poly(ethylenimin) basierte Copolymere zur Anbindung und Freisetzung von genetischem Material, insbesondere von DNA/RNA, sowie Verfahren zu deren Herstellung und Verwendung |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US10131747B2 (enExample) |
| EP (1) | EP3052545B1 (enExample) |
| JP (1) | JP6431533B2 (enExample) |
| CN (1) | CN105683256B (enExample) |
| CA (1) | CA2926154C (enExample) |
| DE (1) | DE102013016750A1 (enExample) |
| DK (1) | DK3052545T3 (enExample) |
| ES (1) | ES2691094T3 (enExample) |
| HU (1) | HUE040402T2 (enExample) |
| WO (1) | WO2015048940A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101892955B1 (ko) | 2017-01-25 | 2018-08-29 | 국방과학연구소 | 치환된 Poly[2-(3-butenyl)-2-oxazoline] 및 Nylon-6,6를 포함하는 섬유 및 그 제조방법 |
| CN116406394A (zh) * | 2020-10-19 | 2023-07-07 | 根特大学 | 可交联的烯丙基酰氨基聚合物 |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19726186A1 (de) * | 1997-06-20 | 1998-12-24 | Boehringer Ingelheim Int | Komplexe für den Transport von Nukleinsäure in höhere eukaryotische Zellen |
| JP2005137253A (ja) * | 2003-11-06 | 2005-06-02 | Kawamura Inst Of Chem Res | ポリイオン会合体およびポリイオン会合体からなる生体物質キャリアー |
| DE20122328U1 (de) * | 2001-12-07 | 2006-02-09 | Sandler Ag | Neue modifizierte Poly-2-oxazoline |
| WO2007084797A1 (en) | 2006-01-23 | 2007-07-26 | Abbott Laboratories | Chemically modified polycation polymer for sirna delivery |
| WO2009102952A2 (en) | 2008-02-13 | 2009-08-20 | Hyperbranch Medical Technology, Inc. | Crosslinked polyalkyleneimine hydrogels with tunable degradation rates |
| US20090215166A1 (en) * | 2005-08-17 | 2009-08-27 | Universitat Regensburg | Cationic Polymer for Transporting Nucleic Acids in Cells |
| WO2011162366A1 (ja) | 2010-06-25 | 2011-12-29 | 東レ株式会社 | 水溶性ポリマー及び水溶性ナノ粒子複合体 |
| WO2012149591A1 (de) | 2011-05-03 | 2012-11-08 | Ke-Kelit Kunststoffwerk Gesellschaft M.B.H. | Verwendung von kontaktbioziden basierend auf poly (2 - substituierten) oxazolinen |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3251778A (en) * | 1960-08-04 | 1966-05-17 | Petrolite Corp | Process of preventing scale |
| DE10029028A1 (de) * | 2000-06-13 | 2001-12-20 | Basf Ag | Verwendung von acylierten Polyaminen zur Modifizierung von Oberflächen |
| US20050238825A1 (en) * | 2004-04-26 | 2005-10-27 | Isp Investments Inc. | Crosslinked polymeric composition |
| CN102149749B (zh) * | 2008-07-10 | 2014-06-25 | 塞瑞纳治疗公司 | 具有惰性端基的聚噁唑啉、由被保护的引发基团制备的聚噁唑啉以及相关化合物 |
| CN101768276B (zh) * | 2008-12-26 | 2011-11-30 | 中国科学技术大学 | 聚乙二醇单甲醚-聚己内酯-聚乙烯亚胺三嵌段共聚物及其应用 |
| TR201909167T4 (tr) | 2011-01-04 | 2019-07-22 | Gatt Tech B V | Elektrofilik olarak aktive edilmiş polioksazolinden derive edilen çapraz bağlı polimerler ve implantlar. |
| EP2683420B1 (en) * | 2011-03-11 | 2018-05-23 | W. L. Gore & Associates, Inc. | Improvements to immobilised biological entities |
| WO2013137736A1 (en) | 2012-03-16 | 2013-09-19 | Bender Analytical Holding B.V. | Cross-linked polymers and medical products derived from nucleophilically activated polyoxazoline |
-
2013
- 2013-10-02 DE DE102013016750.7A patent/DE102013016750A1/de active Pending
-
2014
- 2014-10-02 US US15/026,882 patent/US10131747B2/en active Active
- 2014-10-02 WO PCT/DE2014/000500 patent/WO2015048940A1/de not_active Ceased
- 2014-10-02 CA CA2926154A patent/CA2926154C/en active Active
- 2014-10-02 EP EP14803038.0A patent/EP3052545B1/de active Active
- 2014-10-02 DK DK14803038.0T patent/DK3052545T3/en active
- 2014-10-02 ES ES14803038.0T patent/ES2691094T3/es active Active
- 2014-10-02 JP JP2016519856A patent/JP6431533B2/ja active Active
- 2014-10-02 CN CN201480059919.6A patent/CN105683256B/zh active Active
- 2014-10-02 HU HUE14803038A patent/HUE040402T2/hu unknown
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19726186A1 (de) * | 1997-06-20 | 1998-12-24 | Boehringer Ingelheim Int | Komplexe für den Transport von Nukleinsäure in höhere eukaryotische Zellen |
| DE20122328U1 (de) * | 2001-12-07 | 2006-02-09 | Sandler Ag | Neue modifizierte Poly-2-oxazoline |
| JP2005137253A (ja) * | 2003-11-06 | 2005-06-02 | Kawamura Inst Of Chem Res | ポリイオン会合体およびポリイオン会合体からなる生体物質キャリアー |
| US20090215166A1 (en) * | 2005-08-17 | 2009-08-27 | Universitat Regensburg | Cationic Polymer for Transporting Nucleic Acids in Cells |
| WO2007084797A1 (en) | 2006-01-23 | 2007-07-26 | Abbott Laboratories | Chemically modified polycation polymer for sirna delivery |
| US20080112916A1 (en) * | 2006-01-23 | 2008-05-15 | Ernst Wagner | CHEMICALLY MODIFIED POLYCATION POLYMER FOR siRNA DELIVERY |
| WO2009102952A2 (en) | 2008-02-13 | 2009-08-20 | Hyperbranch Medical Technology, Inc. | Crosslinked polyalkyleneimine hydrogels with tunable degradation rates |
| WO2011162366A1 (ja) | 2010-06-25 | 2011-12-29 | 東レ株式会社 | 水溶性ポリマー及び水溶性ナノ粒子複合体 |
| WO2012149591A1 (de) | 2011-05-03 | 2012-11-08 | Ke-Kelit Kunststoffwerk Gesellschaft M.B.H. | Verwendung von kontaktbioziden basierend auf poly (2 - substituierten) oxazolinen |
Non-Patent Citations (12)
| Title |
|---|
| A. Gress, A. Völkel, H. Schlaad; Thio-click modification of poly[2-(3-butenyl)-2-oxazoline] Macromolecules 40, 2007, 7928-7933 |
| A. M. Doody, J. N. Korley, K. P. Dang, P. N. Zawaneh, D. Putnam: Characterizing the structure/function parameter space of hydrocarbonconjugated branched polyethylenimine for DNA delivery in vitro, J. Control. Release 116, 2006, 227-237 |
| D. Sehgal, I. K. Vijay: A method for the high efficiency of water-soluble carbodiimide-mediated amidation, Anal. Biochem. 218, 1994, 87-91 |
| H. Tian, F. Li, J. Chen, Y. Huang, X. Chen: N-Isopropylacrylamide-Modified Polyethylenimines as Effective Gene Carriers, Macromolecular. Bioscience 12, 2012, 1680-1688 |
| L. Van, W. T. S. Huck, X. -M. Zhao, G. M. Whitesides: Patterning Thin Films of Poly(ethylene imine) an a Reactive SAM Using Microcontact Printing, Langmuir 15, 1999, 1208-1214 |
| M. L. Forrest, G. E. Meister, J. T. Koerber, D. W. Packl: Partial Acetylation of Polyethylenimin Enhances In Vitro Gene Delivery, Pharm. Res. 21, 2004, 365-371 |
| M. Thomas, A. M. Klibanov: Enhancing polyethylenimine's delivery of plasmid DNA into mammalian cells, PNAS 99, 2002, 14640-14645 |
| NIMESH, Surendra et. al.: Influence of acyl chain length on transfection mediated by acylated PEI nanoparticles. In: International Journal of Pharmaceutics, Vol. 337, (2007), 265-374 * |
| S. Nimesh, A. Aggarwal, P. Kumar, Y. Singh, K. C. Gupta, R. Chandra: Influence of acyl chain length an transfection mediated by acylated PEI nanoparticles, I. J. Pharm. 337, 2007, 265-274 |
| T. R. Dargaville et al.: Poly(2-oxazoline) hydrogel monoliths via thiol-ene coupling, Macromol. Rapid Commun. 33, 2012, 1695-700 |
| TIAN, Huayu et.a.: N-Isopropylacrylamide-Modified Polyethylenimines as Effective Gene Carriers. In: Macromol. Biosci., Vol. 12, (2012), 1680-1688 * |
| Y. Chujo, Y. Yoshifuji, K. Sada, T. Saegusa: A Novel Nonionic Hydrogel from 2-Methyl-2-oxazoline, Macromolecules 22, 1989, 1074-1077 |
Also Published As
| Publication number | Publication date |
|---|---|
| US20170166697A1 (en) | 2017-06-15 |
| EP3052545B1 (de) | 2018-07-25 |
| HUE040402T2 (hu) | 2019-03-28 |
| WO2015048940A1 (de) | 2015-04-09 |
| CN105683256B (zh) | 2018-02-23 |
| US10131747B2 (en) | 2018-11-20 |
| ES2691094T3 (es) | 2018-11-23 |
| JP6431533B2 (ja) | 2018-11-28 |
| EP3052545A1 (de) | 2016-08-10 |
| CN105683256A (zh) | 2016-06-15 |
| CA2926154A1 (en) | 2015-04-09 |
| JP2016533409A (ja) | 2016-10-27 |
| CA2926154C (en) | 2022-08-30 |
| DK3052545T3 (en) | 2018-10-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Gerhardt et al. | Development of chitosan/Spirulina sp. blend films as biosorbents for Cr6+ and Pb2+ removal | |
| DE3688922T2 (de) | Reaktive Acrylharzmikroteilchen, deren Herstellung und sie enthaltende vernetzbare Zusammensetzungen. | |
| US11149132B2 (en) | Composite for cellulose fiber dispersion and cellulose fiber composition | |
| EP1603973A1 (de) | Uv-härtender schmelzklebstoff | |
| Kyhoiesh et al. | Synthesis and characterization of polyacrylamide/crotonic acid and its composites with carbon nanotube and Rhodamine B | |
| Torabi et al. | Chitosan and functionalized acrylic nanoparticles as the precursor of new generation of bio-based antibacterial films | |
| Panic et al. | Methacrylic acid based polymer networks with a high content of unfunctionalized nanosilica: Particle distribution, swelling, and rheological properties | |
| EP3052545B1 (de) | Neue poly(ethylenimin) basierte copolymere zur anbindung und freisetzung von genetischem material, insbesondere von dna/rna, sowie verfahren zu deren herstellung und verwendung | |
| Singh et al. | Ultrasmall Sulfur‐Dots‐Mediated Facile Photopolymerization for the Production of Smart Injectable Ink for 3D Printing Applications | |
| WO2002068481A1 (de) | Phosphorhaltige polymere für optischen signalwandler | |
| US20210403683A1 (en) | Composite for cellulose fiber dispersion and cellulose fiber composition | |
| DE2640513B2 (de) | Emulsionsmasse | |
| DE102009029488A1 (de) | Polymerisationsinitiator mit Arylazid und Oberflächenmodifikationsverfahren eines cyclischen Olefincopolymers unter Verwendung desselben | |
| DE102018220125A1 (de) | Oberflächenmodifikation von Kathodenaktivmaterialien zur verbesserten Binderhaftung | |
| DE102017011013A1 (de) | Verfahren zur Erzeugung von biofunktionalen Polymerpartikeln | |
| DE102010004553A1 (de) | Oberflächenmodifizierungssystem für die Beschichtung von Substratoberflächen | |
| DE102005037979B4 (de) | Sensor mit mehrphasigem, segmentiertem Polymernetzwerk | |
| EP1278834A2 (de) | Verfahren für die komplexe nukleinsäureanalytik | |
| WO1999031189A1 (de) | Hydrophile polymerbeschichtungen auf hydrophoben oder hydrophobisierten oberflächen für biotechnologische anwendungen | |
| HK1225051B (zh) | 用於连接和释放遗传物质，特别是dna/rna，的新型聚乙烯亚胺-基共聚物及其制备方法和用途 | |
| EP3053905A1 (de) | Durch sichtbares Licht induzierte Zykloaddition zur Polymerisation bzw. Vernetzung mittels Azirin-Verbindungen | |
| WO2025131751A1 (de) | Verfahren und beschichtungssystem zur immobilisierung von biomolekülen | |
| DE102022112772A1 (de) | Verfahren zur Herstellung von CMP-beschichteten Siliziumdioxid-Sphären, CMP-beschichtete Siliziumdioxid-Sphären und deren Verwendung | |
| US20200239645A1 (en) | Method for activating the surface of polymer materials | |
| DE102017112012A1 (de) | Bioorthogonale 3D-in situ-Hydrogele in Form eines auf einem Träger immobilisierten Netzwerks für Biosensoren sowie Verfahren zu deren Herstellung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| R163 | Identified publications notified | ||
| R012 | Request for examination validly filed | ||
| R081 | Change of applicant/patentee |
Owner name: SMARTDYELIVERY GMBH, DE Free format text: FORMER OWNER: FRIEDRICH-SCHILLER-UNIVERSITAET JENA, 07743 JENA, DE |
|
| R082 | Change of representative |
Representative=s name: PATENT- UND RECHTSANWALTSKANZLEI BOCK BIEBER D, DE |
|
| R016 | Response to examination communication | ||
| R016 | Response to examination communication | ||
| R016 | Response to examination communication |