JP5346340B2 - 創傷を治癒するため制御された酸化窒素放出を提供する超高分子ポリマー複合体 - Google Patents
創傷を治癒するため制御された酸化窒素放出を提供する超高分子ポリマー複合体 Download PDFInfo
- Publication number
- JP5346340B2 JP5346340B2 JP2010522143A JP2010522143A JP5346340B2 JP 5346340 B2 JP5346340 B2 JP 5346340B2 JP 2010522143 A JP2010522143 A JP 2010522143A JP 2010522143 A JP2010522143 A JP 2010522143A JP 5346340 B2 JP5346340 B2 JP 5346340B2
- Authority
- JP
- Japan
- Prior art keywords
- glu
- cys
- pvmma
- polymer
- poly
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 title claims abstract description 297
- 239000002131 composite material Substances 0.000 title claims description 75
- 208000027418 Wounds and injury Diseases 0.000 title description 40
- 206010052428 Wound Diseases 0.000 title description 36
- 229920000642 polymer Polymers 0.000 claims abstract description 93
- 238000000034 method Methods 0.000 claims abstract description 47
- 239000000203 mixture Substances 0.000 claims abstract description 47
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 28
- 239000000227 bioadhesive Substances 0.000 claims abstract description 22
- 238000000576 coating method Methods 0.000 claims abstract description 16
- 239000011248 coating agent Substances 0.000 claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- 238000001523 electrospinning Methods 0.000 claims abstract description 9
- 125000000524 functional group Chemical group 0.000 claims abstract description 8
- 125000005647 linker group Chemical group 0.000 claims abstract description 7
- 108090000765 processed proteins & peptides Proteins 0.000 claims abstract description 6
- 238000000707 layer-by-layer assembly Methods 0.000 claims abstract description 4
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 108
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 claims description 51
- 239000001856 Ethyl cellulose Substances 0.000 claims description 49
- 229920001249 ethyl cellulose Polymers 0.000 claims description 49
- 235000019325 ethyl cellulose Nutrition 0.000 claims description 49
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 claims description 33
- PABVKUJVLNMOJP-WHFBIAKZSA-N Glu-Cys Chemical compound OC(=O)CC[C@H](N)C(=O)N[C@@H](CS)C(O)=O PABVKUJVLNMOJP-WHFBIAKZSA-N 0.000 claims description 30
- RITKHVBHSGLULN-WHFBIAKZSA-N L-gamma-glutamyl-L-cysteine Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(O)=O RITKHVBHSGLULN-WHFBIAKZSA-N 0.000 claims description 30
- 108010068906 gamma-glutamylcysteine Proteins 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 27
- -1 alkyl vinyl ether Chemical compound 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 239000004005 microsphere Substances 0.000 claims description 17
- 229920001577 copolymer Polymers 0.000 claims description 13
- 229960003180 glutathione Drugs 0.000 claims description 13
- 239000011976 maleic acid Substances 0.000 claims description 13
- 239000002121 nanofiber Substances 0.000 claims description 13
- 239000002840 nitric oxide donor Substances 0.000 claims description 13
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical group O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 12
- 230000003993 interaction Effects 0.000 claims description 11
- 229920001223 polyethylene glycol Polymers 0.000 claims description 11
- 108010024636 Glutathione Proteins 0.000 claims description 10
- 230000002209 hydrophobic effect Effects 0.000 claims description 10
- 229920002732 Polyanhydride Polymers 0.000 claims description 9
- 239000002202 Polyethylene glycol Substances 0.000 claims description 8
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 8
- 229920002554 vinyl polymer Polymers 0.000 claims description 8
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical class OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 229920001983 poloxamer Polymers 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 239000007921 spray Substances 0.000 claims description 6
- 238000005507 spraying Methods 0.000 claims description 6
- OJGVRWVZHGUOLY-BQBZGAKWSA-N (2s)-5-[[(2r)-1-(carboxymethylamino)-1-oxo-3-sulfanylpropan-2-yl]amino]-2-(hydroxymethylamino)-5-oxopentanoic acid Chemical compound OCN[C@H](C(O)=O)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O OJGVRWVZHGUOLY-BQBZGAKWSA-N 0.000 claims description 5
- PKYAVRMYTBBRLS-FXQIFTODSA-N Glu-Cys-Glu Chemical compound OC(=O)CC[C@H](N)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCC(O)=O)C(O)=O PKYAVRMYTBBRLS-FXQIFTODSA-N 0.000 claims description 5
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims description 5
- HKBNQXMLSMKLJV-BQBZGAKWSA-N L-gamma-glutamyl-L-cysteinyl-beta-alanine Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCCC(O)=O HKBNQXMLSMKLJV-BQBZGAKWSA-N 0.000 claims description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 5
- 150000004007 S-nitroso compounds Chemical class 0.000 claims description 5
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims description 5
- 235000018417 cysteine Nutrition 0.000 claims description 5
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 5
- 239000000194 fatty acid Substances 0.000 claims description 5
- 229930195729 fatty acid Natural products 0.000 claims description 5
- HKBNQXMLSMKLJV-UHFFFAOYSA-N gamma-L-glutamyl-L-cysteinyl-beta-alanine Natural products OC(=O)C(N)CCC(=O)NC(CS)C(=O)NCCC(O)=O HKBNQXMLSMKLJV-UHFFFAOYSA-N 0.000 claims description 5
- 108700031574 gamma-glutamyl-cysteinyl-glutamic acid Proteins 0.000 claims description 5
- 230000035876 healing Effects 0.000 claims description 5
- 108700020537 homoglutathione Proteins 0.000 claims description 5
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 4
- 239000004698 Polyethylene Substances 0.000 claims description 4
- 206010072170 Skin wound Diseases 0.000 claims description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 4
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadec-1-ene Chemical compound CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 claims description 4
- 229940074982 poly(vinylpyrrolidone-co-vinyl-acetate) Drugs 0.000 claims description 4
- 229920000573 polyethylene Polymers 0.000 claims description 4
- 229920001661 Chitosan Polymers 0.000 claims description 3
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 claims description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 3
- 229920001400 block copolymer Polymers 0.000 claims description 3
- 150000002191 fatty alcohols Chemical class 0.000 claims description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 3
- 229960000502 poloxamer Drugs 0.000 claims description 3
- 229920000141 poly(maleic anhydride) Polymers 0.000 claims description 3
- 229920001451 polypropylene glycol Polymers 0.000 claims description 3
- 230000001737 promoting effect Effects 0.000 claims description 3
- 206010040872 skin infection Diseases 0.000 claims description 3
- ICRHORQIUXBEPA-UHFFFAOYSA-N thionitrous acid Chemical compound SN=O ICRHORQIUXBEPA-UHFFFAOYSA-N 0.000 claims description 3
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical class N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 claims description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 2
- DUKURNFHYQXCJG-UHFFFAOYSA-N Lewis A pentasaccharide Chemical class OC1C(O)C(O)C(C)OC1OC1C(OC2C(C(O)C(O)C(CO)O2)O)C(NC(C)=O)C(OC2C(C(OC3C(OC(O)C(O)C3O)CO)OC(CO)C2O)O)OC1CO DUKURNFHYQXCJG-UHFFFAOYSA-N 0.000 claims description 2
- OVRNDRQMDRJTHS-FMDGEEDCSA-N N-acetyl-beta-D-glucosamine Chemical class CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-FMDGEEDCSA-N 0.000 claims description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Chemical class NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 claims description 2
- 229960002442 glucosamine Drugs 0.000 claims description 2
- 229950006780 n-acetylglucosamine Drugs 0.000 claims description 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 2
- 238000009987 spinning Methods 0.000 claims description 2
- 229920002959 polymer blend Polymers 0.000 claims 3
- 238000000151 deposition Methods 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 16
- 150000001335 aliphatic alkanes Chemical class 0.000 abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 abstract description 2
- 150000001408 amides Chemical class 0.000 abstract description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 238000000889 atomisation Methods 0.000 abstract 1
- 125000003262 carboxylic acid ester group Chemical class [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 92
- HYHSBSXUHZOYLX-WDSKDSINSA-N S-nitrosoglutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CSN=O)C(=O)NCC(O)=O HYHSBSXUHZOYLX-WDSKDSINSA-N 0.000 description 67
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 66
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
- 239000000843 powder Substances 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 238000000338 in vitro Methods 0.000 description 23
- 230000029663 wound healing Effects 0.000 description 20
- 239000000835 fiber Substances 0.000 description 15
- 238000011068 loading method Methods 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 14
- 239000002953 phosphate buffered saline Substances 0.000 description 14
- 230000009918 complex formation Effects 0.000 description 13
- 206010012601 diabetes mellitus Diseases 0.000 description 13
- 239000010408 film Substances 0.000 description 12
- 241001465754 Metazoa Species 0.000 description 11
- 238000001228 spectrum Methods 0.000 description 11
- MUMXDRRTIYLYMY-YJKCNMNRSA-N (Z)-[dodecyl-[6-(dodecylazaniumyl)hexyl]amino]-oxido-oxidoiminoazanium Chemical compound CCCCCCCCCCCC[NH2+]CCCCCCN(CCCCCCCCCCCC)[N+](\[O-])=N\[O-] MUMXDRRTIYLYMY-YJKCNMNRSA-N 0.000 description 9
- 210000001519 tissue Anatomy 0.000 description 9
- 239000012736 aqueous medium Substances 0.000 description 8
- 239000008280 blood Substances 0.000 description 7
- 210000004369 blood Anatomy 0.000 description 7
- 239000004744 fabric Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000000523 sample Substances 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 210000003491 skin Anatomy 0.000 description 6
- 238000002791 soaking Methods 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- JKRODHBGNBKZLE-YUMQZZPRSA-N (2s)-2-amino-5-[[(2r)-1-[(2-ethoxy-2-oxoethyl)amino]-1-oxo-3-sulfanylpropan-2-yl]amino]-5-oxopentanoic acid Chemical compound CCOC(=O)CNC(=O)[C@H](CS)NC(=O)CC[C@H](N)C(O)=O JKRODHBGNBKZLE-YUMQZZPRSA-N 0.000 description 5
- 108700024319 S-ethyl glutathione Proteins 0.000 description 5
- 239000004809 Teflon Substances 0.000 description 5
- 229920006362 Teflon® Polymers 0.000 description 5
- 238000002835 absorbance Methods 0.000 description 5
- 150000008065 acid anhydrides Chemical group 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- 238000005102 attenuated total reflection Methods 0.000 description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
- 230000006378 damage Effects 0.000 description 5
- 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 5
- 238000002474 experimental method Methods 0.000 description 5
- 239000003517 fume Substances 0.000 description 5
- 239000008103 glucose Substances 0.000 description 5
- 208000014674 injury Diseases 0.000 description 5
- 230000007774 longterm Effects 0.000 description 5
- 238000007034 nitrosation reaction Methods 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- 239000000651 prodrug Substances 0.000 description 5
- 229940002612 prodrug Drugs 0.000 description 5
- 230000002459 sustained effect Effects 0.000 description 5
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 5
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 229940098773 bovine serum albumin Drugs 0.000 description 4
- 235000011089 carbon dioxide Nutrition 0.000 description 4
- 230000015556 catabolic process Effects 0.000 description 4
- 238000006731 degradation reaction Methods 0.000 description 4
- 239000011888 foil Substances 0.000 description 4
- UPBDXRPQPOWRKR-UHFFFAOYSA-N furan-2,5-dione;methoxyethene Chemical compound COC=C.O=C1OC(=O)C=C1 UPBDXRPQPOWRKR-UHFFFAOYSA-N 0.000 description 4
- 229920001600 hydrophobic polymer Polymers 0.000 description 4
- 230000006698 induction Effects 0.000 description 4
- 208000015181 infectious disease Diseases 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000001356 surgical procedure Methods 0.000 description 4
- 238000013268 sustained release Methods 0.000 description 4
- 239000012730 sustained-release form Substances 0.000 description 4
- 229920002873 Polyethylenimine Polymers 0.000 description 3
- 239000012190 activator Substances 0.000 description 3
- 238000007605 air drying Methods 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 125000002843 carboxylic acid group Chemical group 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 238000012512 characterization method Methods 0.000 description 3
- 230000001684 chronic effect Effects 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 208000035475 disorder Diseases 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000001879 gelation Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000000017 hydrogel Substances 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 150000003141 primary amines Chemical group 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- 230000002269 spontaneous effect Effects 0.000 description 3
- 238000007619 statistical method Methods 0.000 description 3
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 3
- 229940124530 sulfonamide Drugs 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 description 3
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 3
- 238000001291 vacuum drying Methods 0.000 description 3
- QTJKCQPXTOYYHJ-BYPYZUCNSA-N (2r)-2-acetamido-3-nitrososulfanylpropanoic acid Chemical compound CC(=O)N[C@H](C(O)=O)CSN=O QTJKCQPXTOYYHJ-BYPYZUCNSA-N 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- PIWKPBJCKXDKJR-UHFFFAOYSA-N Isoflurane Chemical compound FC(F)OC(Cl)C(F)(F)F PIWKPBJCKXDKJR-UHFFFAOYSA-N 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
- 229920003072 Plasdone™ povidone Polymers 0.000 description 2
- XOWVFANEOZMPKG-REOHCLBHSA-N S-nitroso-L-cysteine Chemical compound OC(=O)[C@@H](N)CSN=O XOWVFANEOZMPKG-REOHCLBHSA-N 0.000 description 2
- ZSJLQEPLLKMAKR-UHFFFAOYSA-N Streptozotocin Natural products O=NN(C)C(=O)NC1C(O)OC(CO)C(O)C1O ZSJLQEPLLKMAKR-UHFFFAOYSA-N 0.000 description 2
- 238000000692 Student's t-test Methods 0.000 description 2
- 125000004018 acid anhydride group Chemical group 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000035587 bioadhesion Effects 0.000 description 2
- 230000017531 blood circulation Effects 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 238000012377 drug delivery Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000005274 electronic transitions Effects 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 230000002949 hemolytic effect Effects 0.000 description 2
- 230000002779 inactivation Effects 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 229960002725 isoflurane Drugs 0.000 description 2
- 238000002386 leaching Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000003595 mist Substances 0.000 description 2
- 230000000877 morphologic effect Effects 0.000 description 2
- 150000004005 nitrosamines Chemical class 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 238000011552 rat model Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 238000004062 sedimentation Methods 0.000 description 2
- 150000003384 small molecules Chemical class 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ZSJLQEPLLKMAKR-GKHCUFPYSA-N streptozocin Chemical compound O=NN(C)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O ZSJLQEPLLKMAKR-GKHCUFPYSA-N 0.000 description 2
- 229960001052 streptozocin Drugs 0.000 description 2
- 238000009864 tensile test Methods 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- 230000000304 vasodilatating effect Effects 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- NAFSOHFQRKIHBJ-WDSKDSINSA-N (2s)-5-[[(2r)-1-(carboxymethylamino)-3-nitrososulfanyl-1-oxopropan-2-yl]amino]-2-hydrazinyl-5-oxopentanoic acid Chemical compound NN[C@H](C(O)=O)CCC(=O)N[C@@H](CSN=O)C(=O)NCC(O)=O NAFSOHFQRKIHBJ-WDSKDSINSA-N 0.000 description 1
- MZAGXDHQGXUDDX-JSRXJHBZSA-N (e,2z)-4-ethyl-2-hydroxyimino-5-nitrohex-3-enamide Chemical compound [O-][N+](=O)C(C)C(/CC)=C/C(=N/O)/C(N)=O MZAGXDHQGXUDDX-JSRXJHBZSA-N 0.000 description 1
- OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- WKRBZXGRENYWJO-USPAICOZSA-M C(CC(=O)N[C@@H](CS)C(=O)NCC(=O)O)[C@@H](C(=O)O)N.N(=O)[O-].[Na+] Chemical compound C(CC(=O)N[C@@H](CS)C(=O)NCC(=O)O)[C@@H](C(=O)O)N.N(=O)[O-].[Na+] WKRBZXGRENYWJO-USPAICOZSA-M 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 1
- 208000008960 Diabetic foot Diseases 0.000 description 1
- 206010056340 Diabetic ulcer Diseases 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- 102000001554 Hemoglobins Human genes 0.000 description 1
- 108010054147 Hemoglobins Proteins 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 1
- 229930064664 L-arginine Natural products 0.000 description 1
- 235000014852 L-arginine Nutrition 0.000 description 1
- MZNYWPRCVDMOJG-UHFFFAOYSA-N N-(1-naphthyl)ethylenediamine dihydrochloride Chemical compound [Cl-].[Cl-].C1=CC=C2C([NH2+]CC[NH3+])=CC=CC2=C1 MZNYWPRCVDMOJG-UHFFFAOYSA-N 0.000 description 1
- WNYADZVDBIBLJJ-UHFFFAOYSA-N N-Nitrosopyrrolidine Chemical compound O=NN1CCCC1 WNYADZVDBIBLJJ-UHFFFAOYSA-N 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- 108010001742 S-Nitrosoglutathione Proteins 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 208000002847 Surgical Wound Diseases 0.000 description 1
- 206010057040 Temperature intolerance Diseases 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 108010073929 Vascular Endothelial Growth Factor A Proteins 0.000 description 1
- 102000005789 Vascular Endothelial Growth Factors Human genes 0.000 description 1
- 108010019530 Vascular Endothelial Growth Factors Proteins 0.000 description 1
- 206010048038 Wound infection Diseases 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 150000008064 anhydrides Chemical group 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000002785 anti-thrombosis Effects 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 239000012867 bioactive agent Substances 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 239000012620 biological material Substances 0.000 description 1
- 238000001574 biopsy Methods 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000006664 bond formation reaction Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 231100000357 carcinogen Toxicity 0.000 description 1
- 239000003183 carcinogenic agent Substances 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 230000005779 cell damage Effects 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 239000007979 citrate buffer Substances 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 239000003479 dental cement Substances 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- RAABOESOVLLHRU-UHFFFAOYSA-O diazenium Chemical compound [NH2+]=N RAABOESOVLLHRU-UHFFFAOYSA-O 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000000066 endothelium dependent relaxing factor Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 210000002950 fibroblast Anatomy 0.000 description 1
- 230000019305 fibroblast migration Effects 0.000 description 1
- 238000009501 film coating Methods 0.000 description 1
- 239000013020 final formulation Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 230000008543 heat sensitivity Effects 0.000 description 1
- 231100000700 hepatocarcinogen Toxicity 0.000 description 1
- 238000006897 homolysis reaction Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000010191 image analysis Methods 0.000 description 1
- 125000005462 imide group Chemical group 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 230000003100 immobilizing effect Effects 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000012606 in vitro cell culture Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 230000029774 keratinocyte migration Effects 0.000 description 1
- DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 description 1
- 229960000991 ketoprofen Drugs 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000012633 leachable Substances 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 239000011859 microparticle Substances 0.000 description 1
- 230000027939 micturition Effects 0.000 description 1
- 239000002114 nanocomposite Substances 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 230000009935 nitrosation Effects 0.000 description 1
- FBUKVWPVBMHYJY-UHFFFAOYSA-M nonanoate Chemical compound CCCCCCCCC([O-])=O FBUKVWPVBMHYJY-UHFFFAOYSA-M 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 238000011275 oncology therapy Methods 0.000 description 1
- 229940082615 organic nitrates used in cardiac disease Drugs 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 208000002815 pulmonary hypertension Diseases 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000037309 reepithelialization Effects 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- 208000037803 restenosis Diseases 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 238000001878 scanning electron micrograph Methods 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 210000000329 smooth muscle myocyte Anatomy 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 210000004872 soft tissue Anatomy 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 235000000891 standard diet Nutrition 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 230000009469 supplementation Effects 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- 229940098465 tincture Drugs 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 230000003827 upregulation Effects 0.000 description 1
- 210000003556 vascular endothelial cell Anatomy 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
Images
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/74—Synthetic polymeric materials
- A61K31/785—Polymers containing nitrogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/56—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
- A61K47/58—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. poly[meth]acrylate, polyacrylamide, polystyrene, polyvinylpyrrolidone, polyvinylalcohol or polystyrene sulfonic acid resin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/42—Use of materials characterised by their function or physical properties
- A61L15/44—Medicaments
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
- A61L29/14—Materials characterised by their function or physical properties, e.g. lubricating compositions
- A61L29/16—Biologically active materials, e.g. therapeutic substances
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
- A61L31/14—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
- A61L31/16—Biologically active materials, e.g. therapeutic substances
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L39/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions of derivatives of such polymers
- C08L39/04—Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member
- C08L39/08—Homopolymers or copolymers of vinyl-pyridine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/10—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing inorganic materials
- A61L2300/114—Nitric oxide, i.e. NO
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L35/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L35/02—Homopolymers or copolymers of esters
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Diabetes (AREA)
- Surgery (AREA)
- Materials Engineering (AREA)
- Polymers & Plastics (AREA)
- Vascular Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Emergency Medicine (AREA)
- Dermatology (AREA)
- Communicable Diseases (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Oncology (AREA)
- Medicinal Preparation (AREA)
- Materials For Medical Uses (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (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 |
|---|---|---|---|
| CA2,599,082 | 2007-08-27 | ||
| CA002599082A CA2599082A1 (en) | 2007-08-27 | 2007-08-27 | Supramacromolecular polymer complexes providing controlled nitric oxide release for healing wounds |
| PCT/CA2008/001484 WO2009026680A1 (en) | 2007-08-27 | 2008-08-20 | Supramacrqmolecular polymer complexes providing controlled nitric oxide release for healing wounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010537008A JP2010537008A (ja) | 2010-12-02 |
| JP2010537008A5 JP2010537008A5 (https=) | 2011-10-13 |
| JP5346340B2 true JP5346340B2 (ja) | 2013-11-20 |
Family
ID=40385170
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010522143A Expired - Fee Related JP5346340B2 (ja) | 2007-08-27 | 2008-08-20 | 創傷を治癒するため制御された酸化窒素放出を提供する超高分子ポリマー複合体 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US8992945B2 (https=) |
| EP (1) | EP2201077A4 (https=) |
| JP (1) | JP5346340B2 (https=) |
| CA (2) | CA2599082A1 (https=) |
| WO (1) | WO2009026680A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102024102999A1 (de) * | 2024-02-02 | 2025-08-07 | Acandis Gmbh | Liner für einen medizinischen Katheter; Medizinischer Katheter mit einem Liner; Verfahren zur Herstellung eines Liners für einen medizinischen Katheter |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2731298T3 (es) | 2005-05-27 | 2019-11-14 | Univ North Carolina Chapel Hill | Partículas de liberación de óxido nítrico para agentes terapéuticos de óxido nítrico y aplicaciones biomédicas |
| CA2671595A1 (en) * | 2009-07-09 | 2011-01-09 | Ping I. Lee | Controlled nitric oxide delivery from aqueous s-nitrosothiol conjugated polymers and their complexes |
| WO2011022652A1 (en) | 2009-08-21 | 2011-02-24 | Novan, Inc. | Topical gels |
| CA2771389C (en) | 2009-08-21 | 2019-04-09 | Novan, Inc. | Wound dressings, methods of using the same and methods of forming the same |
| US8591876B2 (en) | 2010-12-15 | 2013-11-26 | Novan, Inc. | Methods of decreasing sebum production in the skin |
| WO2012118829A2 (en) | 2011-02-28 | 2012-09-07 | Novan, Inc. | Tertiary s-nitrosothiol-modified nitricoxide-releasing xerogels and methods of using the same |
| AU2013300035A1 (en) * | 2012-08-06 | 2015-02-26 | South Dakota Board Of Regents | Directional eluting implantable medical device |
| US9884943B2 (en) | 2012-09-21 | 2018-02-06 | Michigan Technological University | No-releasing polymers and uses thereof |
| JP2016514171A (ja) * | 2013-02-07 | 2016-05-19 | ザ リージェンツ オブ ザ ユニバーシティ オブ ミシガン | Ｓ−ニトロソ−ｎ−アセチルペニシラミン（ｓｎａｐ）をドープした安定性の向上した血栓形成抵抗性／殺菌性の酸化窒素放出性ポリマー |
| EP3016613B1 (en) * | 2013-07-03 | 2018-10-10 | The American University in Cairo | Bio-compatible apitherapeutic nanofibers |
| JP6357156B2 (ja) | 2013-09-02 | 2018-07-11 | テルモ株式会社 | 医療用具およびその製造方法 |
| EP3139962B1 (en) | 2014-05-05 | 2020-12-23 | Advanced Medical Solutions Israel (Sealantis) Ltd | Biological adhesives and sealants and methods of using the same |
| WO2016025550A1 (en) * | 2014-08-14 | 2016-02-18 | Rohm And Haas Company | Polymer with releasable gas |
| GB201506236D0 (en) * | 2015-04-13 | 2015-05-27 | Jellagen Pty Ltd | Modified collagen, methods of manufacture thereof |
| CN105568401A (zh) * | 2015-12-12 | 2016-05-11 | 大连理工大学 | 一种超声雾化辅助静电纺丝技术 |
| US11111362B2 (en) * | 2016-09-26 | 2021-09-07 | Becton, Dickinson And Company | Breathable films with microbial barrier properties |
| EP3570927A4 (en) | 2017-01-21 | 2020-12-23 | Biocrede Inc. | MEDICAL PRODUCTS AND METHODS FOR THE CONTROLLED RELEASE OF NITROGEN OXIDE |
| CN108498879B (zh) | 2017-02-28 | 2021-12-28 | 苏州安德佳生物科技有限公司 | 黏膜下注射用组合物和试剂组合及其应用 |
| EP3395377A1 (en) * | 2017-04-28 | 2018-10-31 | Borealis AG | Soft polypropylene composition with improved properties |
| CN109694887A (zh) * | 2017-10-24 | 2019-04-30 | 朱一民 | 重组酵母菌及其用于制造生物质酒精的用途 |
| CN110025821A (zh) * | 2018-01-12 | 2019-07-19 | 北京环球利康科技有限公司 | 使用生物相容性止血剂和组织封闭剂的组合物处理活动性出血的方法 |
| CN110284263B (zh) * | 2019-06-13 | 2022-03-08 | 上海交通大学 | 叠层复合纳米纤维的制备方法 |
| US11814519B2 (en) * | 2020-03-26 | 2023-11-14 | Virginia Commonwealth University | Nitric oxide-releasing 3D-printing compositions and uses thereof |
| CN114146880B (zh) * | 2021-12-06 | 2023-02-28 | 中国石油大学(华东) | 一种超声雾化辅助层层自组装制备氢气阻隔涂层的方法 |
| CN115125669B (zh) * | 2022-07-15 | 2023-08-11 | 华中科技大学同济医学院附属协和医院 | 一种超声响应性释放一氧化氮电纺膜及其制备方法 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61186309A (ja) * | 1985-02-13 | 1986-08-20 | Toyobo Co Ltd | 口腔粘膜適用組成物 |
| US6255277B1 (en) * | 1993-09-17 | 2001-07-03 | Brigham And Women's Hospital | Localized use of nitric oxide-adducts to prevent internal tissue damage |
| US5770645A (en) * | 1996-08-02 | 1998-06-23 | Duke University Medical Center | Polymers for delivering nitric oxide in vivo |
| US6221425B1 (en) * | 1998-01-30 | 2001-04-24 | Advanced Cardiovascular Systems, Inc. | Lubricious hydrophilic coating for an intracorporeal medical device |
| IT1303793B1 (it) * | 1998-11-27 | 2001-02-23 | Promefarm S R L | "composizione farmaceutica comprendente un composto organico donatoredi ossido nitrico (no)" |
| US6706274B2 (en) * | 2001-01-18 | 2004-03-16 | Scimed Life Systems, Inc. | Differential delivery of nitric oxide |
| US20050113510A1 (en) * | 2001-05-01 | 2005-05-26 | Feldstein Mikhail M. | Method of preparing polymeric adhesive compositions utilizing the mechanism of interaction between the polymer components |
| CA2446064A1 (en) * | 2001-05-02 | 2002-11-07 | Nitromed, Inc. | Nitrosated and nitrosylated nebivolol and its metabolites, compositions and methods of use |
| GB0125222D0 (en) * | 2001-10-19 | 2001-12-12 | Barts & London Nhs Trust | Composition for the treatment of microbial infections |
| AU2003240164A1 (en) * | 2002-06-07 | 2003-12-22 | Ranbaxy Laboratories Limited | Extended release formulation of divalproex sodium |
| US8211455B2 (en) * | 2002-06-19 | 2012-07-03 | Boston Scientific Scimed, Inc. | Implantable or insertable medical devices for controlled delivery of a therapeutic agent |
| US20060240065A1 (en) * | 2005-04-26 | 2006-10-26 | Yung-Ming Chen | Compositions for medical devices containing agent combinations in controlled volumes |
| ES2540929T3 (es) * | 2005-02-01 | 2015-07-14 | Emisphere Technologies, Inc. | Sistema de administración de retención gástrica y liberación controlada |
| GB0505035D0 (en) * | 2005-03-11 | 2005-04-20 | Insense Ltd | Improvements relating to skin dressings |
| US7517914B2 (en) * | 2005-04-04 | 2009-04-14 | Boston Scientificscimed, Inc. | Controlled degradation materials for therapeutic agent delivery |
| BRPI0503201B8 (pt) * | 2005-07-28 | 2021-05-25 | Sci Tech Produtos Medicos Ltda | stents revestidos com blendas poliméricas hidrofílicas, eluidoras de óxido nítrico e s-nitrosotióis |
| JP4812394B2 (ja) * | 2005-10-19 | 2011-11-09 | 扶桑薬品工業株式会社 | 鎮痛用組成物 |
-
2007
- 2007-08-27 CA CA002599082A patent/CA2599082A1/en not_active Abandoned
-
2008
- 2008-08-20 CA CA2697862A patent/CA2697862A1/en not_active Abandoned
- 2008-08-20 EP EP08783394A patent/EP2201077A4/en not_active Withdrawn
- 2008-08-20 JP JP2010522143A patent/JP5346340B2/ja not_active Expired - Fee Related
- 2008-08-20 US US12/675,498 patent/US8992945B2/en not_active Expired - Fee Related
- 2008-08-20 WO PCT/CA2008/001484 patent/WO2009026680A1/en not_active Ceased
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102024102999A1 (de) * | 2024-02-02 | 2025-08-07 | Acandis Gmbh | Liner für einen medizinischen Katheter; Medizinischer Katheter mit einem Liner; Verfahren zur Herstellung eines Liners für einen medizinischen Katheter |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2010537008A (ja) | 2010-12-02 |
| WO2009026680A1 (en) | 2009-03-05 |
| US20100303891A1 (en) | 2010-12-02 |
| US8992945B2 (en) | 2015-03-31 |
| EP2201077A1 (en) | 2010-06-30 |
| EP2201077A4 (en) | 2013-01-09 |
| CA2599082A1 (en) | 2009-02-27 |
| CA2697862A1 (en) | 2009-03-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5346340B2 (ja) | 創傷を治癒するため制御された酸化窒素放出を提供する超高分子ポリマー複合体 | |
| US11857701B2 (en) | Anti-adhesive barrier membrane using alginate and hyaluronic acid for biomedical applications | |
| Zhang et al. | Copper-based metal–organic framework as a controllable nitric oxide-releasing vehicle for enhanced diabetic wound healing | |
| Sadeghi et al. | Carboxymethyl cellulose-human hair keratin hydrogel with controlled clindamycin release as antibacterial wound dressing | |
| Li et al. | Controlled nitric oxide delivery platform based on S-nitrosothiol conjugated interpolymer complexes for diabetic wound healing | |
| US6458386B1 (en) | Medicaments based on polymers composed of methacrylamide-modified gelatin | |
| CN101420989B (zh) | 用于医疗器械和治疗的聚合物no供体前药纳米纤维涂层 | |
| EP1824531B1 (fr) | Biomateriaux porteurs de cyclodextrines aux proprietes d'absorption ameliorees et de liberation progressive et retardee de molecules therapeutiques | |
| JP3404557B2 (ja) | 架橋ヒアルロン酸及びこれらの複合材料 | |
| Qian et al. | Antioxidant biocompatible composite collagen dressing for diabetic wound healing in rat model | |
| Wold et al. | Fabrication of biodegradable polymeric nanofibers with covalently attached NO donors | |
| EP1861130A2 (en) | Device and method for treatment of dermatomycosis, and in particular onychomycosis | |
| GB2526897A (en) | Pharmaceutical formulations for the treatment of pulmonary arterial hypertension | |
| EP1846057A1 (en) | Device for treatment of disorders in the oral cavity with nitric oxide, and manufacturing process for the same | |
| WO2007058190A1 (ja) | 薬剤放出制御組成物および薬剤放出性医療器具 | |
| Zhao et al. | Hydroxypropyl methylcellulose reinforced bilayer hydrogel dressings containing L-arginine-modified polyoxometalate nanoclusters to promote healing of chronic diabetic wounds | |
| CN107141345A (zh) | 一种角蛋白生物大分子一氧化氮供体及其合成与应用 | |
| CN116920165B (zh) | 一种原位产氧的水凝胶及其制备方法和应用 | |
| US8858972B2 (en) | Antimicrobial medicotechnical product, process for its preparation and use | |
| Ali et al. | Exogenous and endogenous nitric oxide eluting polylactic acid-based nanofibrous scaffolds for enhancing angiogenesis of diabetic wounds | |
| Workman et al. | Covalently bound S-nitroso-N-acetylpenicillamine to electrospun polyacrylonitrile nanofibers for multifunctional tissue engineering applications | |
| CN115869459A (zh) | 促伤口愈合的多肽水凝胶及其制备方法与应用 | |
| Cheaburu-Yilmaz et al. | Polysaccharide containing gels for pharmaceutical applications | |
| CN115232305B (zh) | 可释放no气体的聚谷氨酸基水凝胶及其制备方法和应用 | |
| Ajaz et al. | Usra; Hussain, G.; Shahzad, Y.; et al |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20110822 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20110822 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20130123 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20130124 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20130424 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20130502 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20130517 |
|
| 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: 20130717 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20130816 |
|
| R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| LAPS | Cancellation because of no payment of annual fees |