JP5718815B2 - 重合可能なアルキレングリコール(メタ)アクリレートモノマーから調製されるポリマー粒子 - Google Patents
重合可能なアルキレングリコール(メタ)アクリレートモノマーから調製されるポリマー粒子 Download PDFInfo
- Publication number
- JP5718815B2 JP5718815B2 JP2011531565A JP2011531565A JP5718815B2 JP 5718815 B2 JP5718815 B2 JP 5718815B2 JP 2011531565 A JP2011531565 A JP 2011531565A JP 2011531565 A JP2011531565 A JP 2011531565A JP 5718815 B2 JP5718815 B2 JP 5718815B2
- Authority
- JP
- Japan
- Prior art keywords
- polymer
- methacrylate
- poly
- ethylene glycol
- acrylate
- 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.)
- Active
Links
- 229920000642 polymer Polymers 0.000 title claims description 166
- 239000002245 particle Substances 0.000 title claims description 125
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title claims description 109
- 239000000178 monomer Substances 0.000 title claims description 67
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 title claims description 19
- -1 alkylene glycol Chemical compound 0.000 title claims description 19
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 title claims description 19
- 238000000034 method Methods 0.000 claims description 58
- 229920001577 copolymer Polymers 0.000 claims description 50
- 229920001606 poly(lactic acid-co-glycolic acid) Polymers 0.000 claims description 37
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 30
- 238000006116 polymerization reaction Methods 0.000 claims description 26
- 239000011859 microparticle Substances 0.000 claims description 23
- 229920001223 polyethylene glycol Polymers 0.000 claims description 20
- 229920001451 polypropylene glycol Polymers 0.000 claims description 20
- 239000000725 suspension Substances 0.000 claims description 20
- 125000002947 alkylene group Chemical group 0.000 claims description 18
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 17
- 239000012736 aqueous medium Substances 0.000 claims description 12
- 230000036760 body temperature Effects 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- 229920002988 biodegradable polymer Polymers 0.000 claims description 11
- 239000004621 biodegradable polymer Substances 0.000 claims description 11
- 238000009792 diffusion process Methods 0.000 claims description 11
- 230000005496 eutectics Effects 0.000 claims description 11
- 239000011159 matrix material Substances 0.000 claims description 11
- 239000012620 biological material Substances 0.000 claims description 10
- 230000010261 cell growth Effects 0.000 claims description 10
- 239000011557 critical solution Substances 0.000 claims description 10
- 238000004945 emulsification Methods 0.000 claims description 10
- 238000011049 filling Methods 0.000 claims description 9
- 239000012530 fluid Substances 0.000 claims description 9
- 230000008467 tissue growth Effects 0.000 claims description 8
- 230000001747 exhibiting effect Effects 0.000 claims description 7
- 239000004094 surface-active agent Substances 0.000 claims description 7
- 238000007740 vapor deposition Methods 0.000 claims description 7
- 229960000074 biopharmaceutical Drugs 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 239000003102 growth factor Substances 0.000 claims description 6
- 150000003254 radicals Chemical class 0.000 claims description 6
- 230000001172 regenerating effect Effects 0.000 claims description 6
- 229940126586 small molecule drug Drugs 0.000 claims description 6
- 238000004381 surface treatment Methods 0.000 claims description 6
- 239000010419 fine particle Substances 0.000 claims description 5
- 239000000796 flavoring agent Substances 0.000 claims description 5
- 210000000056 organ Anatomy 0.000 claims description 5
- 230000008439 repair process Effects 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 238000013270 controlled release Methods 0.000 claims description 4
- 239000003205 fragrance Substances 0.000 claims description 4
- 229920000747 poly(lactic acid) Polymers 0.000 claims description 4
- 229920000954 Polyglycolide Polymers 0.000 claims description 3
- 235000013355 food flavoring agent Nutrition 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 230000009969 flowable effect Effects 0.000 claims 1
- 210000004027 cell Anatomy 0.000 description 55
- 239000000499 gel Substances 0.000 description 38
- 239000000243 solution Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 11
- 239000000463 material Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 230000008859 change Effects 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 description 7
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 7
- 238000005538 encapsulation Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
- 239000002953 phosphate buffered saline Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 210000001519 tissue Anatomy 0.000 description 7
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000000872 buffer Substances 0.000 description 6
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 230000006870 function Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 229920000208 temperature-responsive polymer Polymers 0.000 description 5
- 230000007704 transition Effects 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000012669 compression test Methods 0.000 description 4
- 238000012377 drug delivery Methods 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 238000011065 in-situ storage Methods 0.000 description 4
- 238000010603 microCT Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 230000035899 viability Effects 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000003349 alamar blue assay Methods 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000000149 argon plasma sintering Methods 0.000 description 3
- 229920001400 block copolymer Polymers 0.000 description 3
- 230000003833 cell viability Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000000799 fluorescence microscopy Methods 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 230000033001 locomotion Effects 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- VOFUROIFQGPCGE-UHFFFAOYSA-N nile red Chemical compound C1=CC=C2C3=NC4=CC=C(N(CC)CC)C=C4OC3=CC(=O)C2=C1 VOFUROIFQGPCGE-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000010526 radical polymerization reaction Methods 0.000 description 3
- 238000004626 scanning electron microscopy Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 2
- 239000012981 Hank's balanced salt solution Substances 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 230000004931 aggregating effect Effects 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 239000012986 chain transfer agent Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000012258 culturing Methods 0.000 description 2
- 125000001295 dansyl group Chemical group [H]C1=C([H])C(N(C([H])([H])[H])C([H])([H])[H])=C2C([H])=C([H])C([H])=C(C2=C1[H])S(*)(=O)=O 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000000502 dialysis Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 2
- 238000002296 dynamic light scattering Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000012091 fetal bovine serum Substances 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000693 micelle Substances 0.000 description 2
- 230000037361 pathway Effects 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920003213 poly(N-isopropyl acrylamide) Polymers 0.000 description 2
- 229920001610 polycaprolactone Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 238000001878 scanning electron micrograph Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- MPLHNVLQVRSVEE-UHFFFAOYSA-N texas red Chemical compound [O-]S(=O)(=O)C1=CC(S(Cl)(=O)=O)=CC=C1C(C1=CC=2CCCN3CCCC(C=23)=C1O1)=C2C1=C(CCC1)C3=[N+]1CCCC3=C2 MPLHNVLQVRSVEE-UHFFFAOYSA-N 0.000 description 2
- 238000001248 thermal gelation Methods 0.000 description 2
- 239000002407 tissue scaffold Substances 0.000 description 2
- RKDVKSZUMVYZHH-UHFFFAOYSA-N 1,4-dioxane-2,5-dione Chemical compound O=C1COC(=O)CO1 RKDVKSZUMVYZHH-UHFFFAOYSA-N 0.000 description 1
- FWBHETKCLVMNFS-UHFFFAOYSA-N 4',6-Diamino-2-phenylindol Chemical compound C1=CC(C(=N)N)=CC=C1C1=CC2=CC=C(C(N)=N)C=C2N1 FWBHETKCLVMNFS-UHFFFAOYSA-N 0.000 description 1
- APKFDSVGJQXUKY-KKGHZKTASA-N Amphotericin-B Natural products O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1C=CC=CC=CC=CC=CC=CC=C[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-KKGHZKTASA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- XPDXVDYUQZHFPV-UHFFFAOYSA-N Dansyl Chloride Chemical compound C1=CC=C2C(N(C)C)=CC=CC2=C1S(Cl)(=O)=O XPDXVDYUQZHFPV-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 102000010834 Extracellular Matrix Proteins Human genes 0.000 description 1
- 108010037362 Extracellular Matrix Proteins Proteins 0.000 description 1
- 101000606535 Homo sapiens Receptor-type tyrosine-protein phosphatase epsilon Proteins 0.000 description 1
- 102100039665 Receptor-type tyrosine-protein phosphatase epsilon Human genes 0.000 description 1
- 102000004142 Trypsin Human genes 0.000 description 1
- 108090000631 Trypsin Proteins 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 238000010669 acid-base reaction Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- APKFDSVGJQXUKY-INPOYWNPSA-N amphotericin B Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-INPOYWNPSA-N 0.000 description 1
- 229960003942 amphotericin b Drugs 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 229920005601 base polymer Polymers 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000012867 bioactive agent Substances 0.000 description 1
- 239000000227 bioadhesive Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000003592 biomimetic effect Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- PBAYDYUZOSNJGU-UHFFFAOYSA-N chelidonic acid Natural products OC(=O)C1=CC(=O)C=C(C(O)=O)O1 PBAYDYUZOSNJGU-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 210000002744 extracellular matrix Anatomy 0.000 description 1
- 238000002073 fluorescence micrograph Methods 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 230000037323 metabolic rate Effects 0.000 description 1
- ACEONLNNWKIPTM-UHFFFAOYSA-N methyl 2-bromopropanoate Chemical compound COC(=O)C(C)Br ACEONLNNWKIPTM-UHFFFAOYSA-N 0.000 description 1
- 230000003278 mimic effect Effects 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 238000004172 nitrogen cycle Methods 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229940065514 poly(lactide) Drugs 0.000 description 1
- 239000004633 polyglycolic acid Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000012798 spherical particle Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 230000017423 tissue regeneration Effects 0.000 description 1
- 229940043263 traditional drug Drugs 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
Classifications
-
- 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
- C12N5/00—Undifferentiated human, animal or plant cells, e.g. cell lines; Tissues; Cultivation or maintenance thereof; Culture media therefor
- C12N5/0068—General culture methods using substrates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12M—APPARATUS FOR ENZYMOLOGY OR MICROBIOLOGY; APPARATUS FOR CULTURING MICROORGANISMS FOR PRODUCING BIOMASS, FOR GROWING CELLS OR FOR OBTAINING FERMENTATION OR METABOLIC PRODUCTS, i.e. BIOREACTORS OR FERMENTERS
- C12M25/00—Means for supporting, enclosing or fixing the microorganisms, e.g. immunocoatings
- C12M25/14—Scaffolds; Matrices
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
- C08F220/285—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing a polyether chain in the alcohol moiety
- C08F220/286—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing a polyether chain in the alcohol moiety and containing polyethylene oxide in the alcohol moiety, e.g. methoxy polyethylene glycol (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
- C08F220/285—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing a polyether chain in the alcohol moiety
- C08F220/287—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing a polyether chain in the alcohol moiety and containing polypropylene oxide in the alcohol moiety
-
- 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
- C12N2533/00—Supports or coatings for cell culture, characterised by material
- C12N2533/30—Synthetic polymers
- C12N2533/40—Polyhydroxyacids, e.g. polymers of glycolic or lactic acid (PGA, PLA, PLGA); Bioresorbable polymers
-
- 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
- C12N2539/00—Supports and/or coatings for cell culture characterised by properties
- C12N2539/10—Coating allowing for selective detachment of cells, e.g. thermoreactive coating
Landscapes
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Biotechnology (AREA)
- Biomedical Technology (AREA)
- Genetics & Genomics (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- General Engineering & Computer Science (AREA)
- Microbiology (AREA)
- Immunology (AREA)
- Sustainable Development (AREA)
- Cell Biology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Preparation (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0818747.8A GB0818747D0 (en) | 2008-10-13 | 2008-10-13 | Biocompatible responsive materials |
| GB0818747.8 | 2008-10-13 | ||
| PCT/GB2009/051362 WO2010043892A1 (en) | 2008-10-13 | 2009-10-13 | Polymer particles prepared from polymerisable alkylene glycol (meth) acrylate monomers |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012505305A JP2012505305A (ja) | 2012-03-01 |
| JP2012505305A5 JP2012505305A5 (enExample) | 2013-07-25 |
| JP5718815B2 true JP5718815B2 (ja) | 2015-05-13 |
Family
ID=40083948
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011531565A Active JP5718815B2 (ja) | 2008-10-13 | 2009-10-13 | 重合可能なアルキレングリコール(メタ)アクリレートモノマーから調製されるポリマー粒子 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8940336B2 (enExample) |
| EP (1) | EP2346914B1 (enExample) |
| JP (1) | JP5718815B2 (enExample) |
| DK (1) | DK2346914T3 (enExample) |
| ES (1) | ES2573941T3 (enExample) |
| GB (1) | GB0818747D0 (enExample) |
| WO (1) | WO2010043892A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10465147B2 (en) * | 2011-10-17 | 2019-11-05 | Agency For Science, Technology And Research | Copolymers |
| WO2014013238A1 (en) | 2012-07-16 | 2014-01-23 | The University Of Nottingham | Scaffold |
| US9205175B2 (en) | 2012-07-27 | 2015-12-08 | Drexel University | Thermosensitive and crosslinkable polymer composite for three-dimensional soft tissue scaffold printing |
| US20170210840A1 (en) * | 2014-08-19 | 2017-07-27 | National University Of Singapore | Thermogelling graft copolymer and method of preparation thereof |
| JP5874859B1 (ja) * | 2014-12-12 | 2016-03-02 | 東洋インキScホールディングス株式会社 | 体液接触用医療用具および生体適合性重合体 |
| JP6815719B2 (ja) * | 2015-05-11 | 2021-01-20 | ポーラ化成工業株式会社 | 海島構造を有する被膜及びこれを形成する組成物 |
| EP3801600B1 (en) * | 2018-06-05 | 2025-04-30 | University of Mississippi Medical Center | PRODUCTION OF ELP MACROPARTICLES AND MICROPARTICLES FOR DRUG DELIVERY |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62224290A (ja) * | 1986-03-26 | 1987-10-02 | Hitachi Chem Co Ltd | 微生物菌体固定化法 |
| US5173421A (en) | 1988-12-14 | 1992-12-22 | Mitsubishi Kasei Corporation | Cell culture carriers |
| US20040195710A1 (en) | 1990-10-15 | 2004-10-07 | Hubbell Jeffrey A. | Gels for encapsulation of biological materials |
| US6103528A (en) | 1998-04-17 | 2000-08-15 | Battelle Memorial Institute | Reversible gelling culture media for in-vitro cell culture in three-dimensional matrices |
| JP2001261845A (ja) * | 2000-03-14 | 2001-09-26 | Mitsubishi Chemicals Corp | ハイドロゲル微粒子 |
| FR2810669B1 (fr) * | 2000-06-27 | 2002-08-30 | Atofina | Copolymeres hydrosolubles thermosensibles a base de (meth) acrylate (poly)ethoxyle, leur fabrication et leur utilisation pour la preparation de film, adhesifs et liants pour nappes fibreuses |
| JP2004087228A (ja) * | 2002-08-26 | 2004-03-18 | Teijin Ltd | リチウムイオン二次電池 |
| GB0228537D0 (en) * | 2002-12-06 | 2003-01-15 | Syngenta Ltd | Particulate suspensions |
| WO2004087228A1 (ja) | 2003-03-28 | 2004-10-14 | Japan Science And Technology Agency | 生体適合性と温度応答性を併せ持つ高分子 |
| JP4294506B2 (ja) * | 2004-01-30 | 2009-07-15 | 株式会社クラレ | 感熱ゲル化性エマルジョン |
| CA2626016A1 (en) * | 2005-10-21 | 2007-06-21 | Panacea Biotec Limited | Pharmaceutical composition comprising at least one anticancer drug and at least one polymer |
-
2008
- 2008-10-13 GB GBGB0818747.8A patent/GB0818747D0/en not_active Ceased
-
2009
- 2009-10-13 ES ES09748135.2T patent/ES2573941T3/es active Active
- 2009-10-13 JP JP2011531565A patent/JP5718815B2/ja active Active
- 2009-10-13 WO PCT/GB2009/051362 patent/WO2010043892A1/en not_active Ceased
- 2009-10-13 DK DK09748135.2T patent/DK2346914T3/en active
- 2009-10-13 EP EP09748135.2A patent/EP2346914B1/en not_active Not-in-force
- 2009-10-13 US US13/123,737 patent/US8940336B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DK2346914T3 (en) | 2016-07-04 |
| EP2346914A1 (en) | 2011-07-27 |
| ES2573941T3 (es) | 2016-06-13 |
| WO2010043892A1 (en) | 2010-04-22 |
| EP2346914B1 (en) | 2016-04-27 |
| US20110305767A1 (en) | 2011-12-15 |
| US8940336B2 (en) | 2015-01-27 |
| GB0818747D0 (en) | 2008-11-19 |
| JP2012505305A (ja) | 2012-03-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5718815B2 (ja) | 重合可能なアルキレングリコール(メタ)アクリレートモノマーから調製されるポリマー粒子 | |
| Qin et al. | Injectable superparamagnetic ferrogels for controlled release of hydrophobic drugs | |
| Gan et al. | Thermogelable PNIPAM microgel dispersion as 3D cell scaffold: effect of syneresis | |
| Chen et al. | Double stimuli-responsive cellulose nanocrystals reinforced electrospun PHBV composites membrane for intelligent drug release | |
| Müller | Sizing, shaping and pharmaceutical applications of polyelectrolyte complex nanoparticles | |
| Wang et al. | Poly (lactic acid)/chitosan hybrid nanoparticles for controlled release of anticancer drug | |
| CN101684174B (zh) | 两亲性可生物降解聚酯梳型接枝共聚物及其温敏原位凝胶体系 | |
| Ma et al. | Synthesis and biological response of casein-based silica nano-composite film for drug delivery system | |
| Wang et al. | Biodegradable thermoresponsive microparticle dispersions for injectable cell delivery prepared using a single-step process | |
| Pham et al. | Aqueous polymeric hollow particles as an opacifier by emulsion polymerization using macro-RAFT amphiphiles | |
| JP2008517878A (ja) | ゲル粒子の形状保持凝集塊の形成の方法とその使用 | |
| Weda et al. | Thermosensitive nanospheres of low-density core–An approach to hollow nanoparticles | |
| CN102138904A (zh) | 一种自固化微球及其制备方法和应用 | |
| CN101484482A (zh) | 两步细乳液工艺 | |
| Qiao et al. | Synthesis of thermosensitive micelles based on poly (N-isopropylacrylamide) and poly (l-alanine) for controlled release of adriamycin | |
| Wang et al. | Controlled long-term sustained release of poly (lactic acid) composite microspheres with dual-responsive cellulose nanocrystals | |
| Anzai et al. | Poly (ɛ-caprolactone)(PCL)–polymeric micelle hybrid sheets for the incorporation and release of hydrophilic proteins | |
| Mackiewicz et al. | Unusual swelling behavior of core-shell microgels built from polymers exhibiting lower critical solubility temperature | |
| ZA200609155B (en) | Polymer particles containing active agents | |
| Michailova et al. | Nanoparticles formed from PNIPAM-g-PEO copolymers in the presence of indomethacin | |
| Aliabadi et al. | Amphiphilic polylactic acid-b-poly (N-(3-aminopropyl) methacrylamide) copolymers: Self-assembly to polymeric micelles for gene delivery | |
| Wu et al. | Fabrication of microgels via supramolecular assembly of cyclodextrin-containing star polycations and oppositely charged linear polyanions | |
| Du et al. | Investigating the Formation of Polymer–Nanoparticle Complex Coacervate Hydrogels Using Polymerization-Induced Self-Assembly-Derived Nanogels with a Succinate-Functional Core | |
| Wang et al. | Synthesis of multicomponent and multiblock copolymers and their sustained release behavior for fluorescein sodium | |
| Baimark et al. | Biodegradable nanoparticles of methoxy poly (ethylene glycol)-b-poly (d, l-lactide)/methoxy poly (ethylene glycol)-b-poly (ϵ-caprolactone) blends for drug delivery |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20120330 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20130531 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20130606 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20130904 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20130910 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20131203 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20131210 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140307 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20140401 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20140620 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20140627 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20141001 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20150217 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20150319 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 5718815 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |