JP2016520157A - 低エンドトキシンのキトサンの製造方法 - Google Patents
低エンドトキシンのキトサンの製造方法 Download PDFInfo
- Publication number
- JP2016520157A JP2016520157A JP2016516244A JP2016516244A JP2016520157A JP 2016520157 A JP2016520157 A JP 2016520157A JP 2016516244 A JP2016516244 A JP 2016516244A JP 2016516244 A JP2016516244 A JP 2016516244A JP 2016520157 A JP2016520157 A JP 2016520157A
- Authority
- JP
- Japan
- Prior art keywords
- chitosan
- acid
- alkaline
- chitin
- derivative
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 229920001661 Chitosan Polymers 0.000 title claims abstract description 325
- 239000002158 endotoxin Substances 0.000 title claims abstract description 116
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 85
- 150000003839 salts Chemical class 0.000 claims abstract description 62
- 239000012670 alkaline solution Substances 0.000 claims abstract description 55
- 239000000203 mixture Substances 0.000 claims abstract description 50
- 229920002101 Chitin Polymers 0.000 claims abstract description 39
- 238000001035 drying Methods 0.000 claims abstract description 27
- 230000007935 neutral effect Effects 0.000 claims abstract description 26
- 239000002253 acid Substances 0.000 claims description 65
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 33
- 239000000243 solution Substances 0.000 claims description 26
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- 230000002439 hemostatic effect Effects 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
- 230000000740 bleeding effect Effects 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- 239000003513 alkali Substances 0.000 claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 239000002585 base Substances 0.000 claims description 8
- 235000011054 acetic acid Nutrition 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 7
- 230000017531 blood circulation Effects 0.000 claims description 7
- 238000012545 processing Methods 0.000 claims description 7
- -1 silver ions Chemical class 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000003755 preservative agent Substances 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 238000005406 washing Methods 0.000 claims description 6
- 229940030225 antihemorrhagics Drugs 0.000 claims description 5
- 239000002874 hemostatic agent Substances 0.000 claims description 5
- YWWVWXASSLXJHU-AATRIKPKSA-N (9E)-tetradecenoic acid Chemical compound CCCC\C=C\CCCCCCCC(O)=O YWWVWXASSLXJHU-AATRIKPKSA-N 0.000 claims description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 4
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 claims description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 4
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- MBMBGCFOFBJSGT-KUBAVDMBSA-N all-cis-docosa-4,7,10,13,16,19-hexaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 claims description 4
- 235000001014 amino acid Nutrition 0.000 claims description 4
- 150000001413 amino acids Chemical class 0.000 claims description 4
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 claims description 4
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 4
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 4
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 claims description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 4
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 claims description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical group CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 claims description 4
- 229930195729 fatty acid Natural products 0.000 claims description 4
- 239000000194 fatty acid Substances 0.000 claims description 4
- 150000004665 fatty acids Chemical class 0.000 claims description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 4
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 claims description 4
- 229910052500 inorganic mineral Chemical class 0.000 claims description 4
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 4
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 claims description 4
- 239000011707 mineral Chemical class 0.000 claims description 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 claims description 4
- 230000002335 preservative effect Effects 0.000 claims description 4
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 claims description 4
- 239000012298 atmosphere Substances 0.000 claims description 3
- 229940093915 gynecological organic acid Drugs 0.000 claims description 3
- 239000004310 lactic acid Substances 0.000 claims description 3
- 235000014655 lactic acid Nutrition 0.000 claims description 3
- 235000005985 organic acids Nutrition 0.000 claims description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 2
- BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical compound CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 claims description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 2
- YWWVWXASSLXJHU-UHFFFAOYSA-N 9E-tetradecenoic acid Natural products CCCCC=CCCCCCCCC(O)=O YWWVWXASSLXJHU-UHFFFAOYSA-N 0.000 claims description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 2
- 235000021357 Behenic acid Nutrition 0.000 claims description 2
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 claims description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 claims description 2
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 claims description 2
- GHXZTYHSJHQHIJ-UHFFFAOYSA-N Chlorhexidine Chemical compound C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 GHXZTYHSJHQHIJ-UHFFFAOYSA-N 0.000 claims description 2
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 claims description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 claims description 2
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 2
- 239000004471 Glycine Substances 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims description 2
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 2
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 claims description 2
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims description 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 2
- 239000005639 Lauric acid Substances 0.000 claims description 2
- 239000002841 Lewis acid Substances 0.000 claims description 2
- 235000021353 Lignoceric acid Nutrition 0.000 claims description 2
- CQXMAMUUWHYSIY-UHFFFAOYSA-N Lignoceric acid Natural products CCCCCCCCCCCCCCCCCCCCCCCC(=O)OCCC1=CC=C(O)C=C1 CQXMAMUUWHYSIY-UHFFFAOYSA-N 0.000 claims description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 2
- 239000004472 Lysine Substances 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
- 239000005642 Oleic acid Substances 0.000 claims description 2
- 235000021314 Palmitic acid Nutrition 0.000 claims description 2
- 235000021319 Palmitoleic acid Nutrition 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
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- JAZBEHYOTPTENJ-JLNKQSITSA-N all-cis-5,8,11,14,17-icosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JAZBEHYOTPTENJ-JLNKQSITSA-N 0.000 claims description 2
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- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims description 2
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- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 claims description 2
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- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
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- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
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- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0024—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Glucans; (beta-1,3)-D-Glucans, e.g. paramylon, coriolan, sclerotan, pachyman, callose, scleroglucan, schizophyllan, laminaran, lentinan or curdlan; (beta-1,6)-D-Glucans, e.g. pustulan; (beta-1,4)-D-Glucans; (beta-1,3)(beta-1,4)-D-Glucans, e.g. lichenan; Derivatives thereof
- C08B37/0027—2-Acetamido-2-deoxy-beta-glucans; Derivatives thereof
- C08B37/003—Chitin, i.e. 2-acetamido-2-deoxy-(beta-1,4)-D-glucan or N-acetyl-beta-1,4-D-glucosamine; Chitosan, i.e. deacetylated product of chitin or (beta-1,4)-D-glucosamine; Derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0003—General processes for their isolation or fractionation, e.g. purification or extraction from biomass
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Abstract
Description
a)無菌環境において、殺菌済みの発熱因子が存在しない(pyrogen-free)設備および材料を使用する工程、
b)エンドトキシンを含有するキトサンを最大24時間で膨潤させる工程、
c)1kg/25Lから1.5kg/25Lのキトサンを、0.01Mから4.0Mの塩基性水酸化物(hydroxide base)中に溶解させる工程、
d)得られた塩基性のキトサン溶液を継続的に撹拌する工程、
e)該溶液を撹拌しながら、60℃から100℃で45分間から4時間加熱する工程、
f)該溶液を、その容積の最大10倍のエンドトキシンフリーの(endotoxin-free)超純水で濯ぐ工程、
g)該溶液をpH6.8から7.5の範囲で中和する工程、
h)超高純度の低エンドトキシンのキトサンスラリーを形成させ、スラリーをエンドトキシンフリーの閉鎖系(closed system)に移す工程、および
i)スラリーから余分な水分を取り除く工程を含む。
(a)水不溶性のキトサンを塩基性溶液と、第1の期間である1時間を超えて接触させる工程、
(b)望ましくはエンドトキシンフリー水を用いて、残存する塩基性溶液を取り除くために水不溶性のキトサンを濯ぐ工程、
(c)相間移動剤を含む反応溶液中で、水不溶性のキトサンを部分的にアセチル化する工程、
(d)界面活性剤を含み、約7.0から約7.4のpHを有する水性溶液に、部分的にアセチル化された水溶性のキトサンを溶解させる工程、
(e)該水性溶液に水混和性溶媒を加え、さらに水性溶液のpHを少なくとも8.0に調整して、水性溶液/水混和性溶媒の混合液から、低濃度のエンドトキシンを含む水溶性キトサンを沈殿させる工程、および
(f)任意に、イソプロパノールなどの非溶媒中で洗浄する工程を含む。
(a)エンドトキシンを含むキトサンを水性溶液中に溶解させる工程、
(b)水性溶液を界面活性剤と接触させ、エンドトキシンの含有量が減少した水不溶性の固形物と水性溶液を形成させる工程、および
(c)固体/液体分離手段により、固形物を水性溶液から分離する工程を含む。
(a)キトサン、キチン、キトサン誘導体、またはキチン誘導体をアルカリ溶液と接触させて、混合物を形成する工程と、
(b)該混合物を1時間未満放置する工程とを含む。
(a)キトサン、キチン、キトサン誘導体、またはキチン誘導体をアルカリ溶液と接触させて、混合物を形成する工程と、
(b)該混合物を直ちに乾燥させる工程とを含む。
1.キトサンのエンドトキシン試験用に、USP(米国薬局方)に詳述されている通りの抽出溶液(4.6mlの1M HClと45.4mlのエンドトキシンフリー水)を調製し、
2.0.1gの試験用キトサン生成物を9.9mlのUSP抽出溶液に加えて抽出し、37℃で48時間放置し、
3.48時間後、100μlの抽出物を0.9mlのエンドトキシンフリー水で希釈し、
4.上記の希釈液100μlを、100μlのチャールズリバー(Charles River)社製のエンドトキシンスペシフィック(Endotoxin Specific)(ES)緩衝液と混合する。
実施例1
50gのキトサンを、50gの1M NaOHと10分間混合した。結果として得られた、湿ったアルカリ性キトサン団粒(crumb)を、直ちに流動層乾燥機(fluid bed drier)内で40℃で乾燥した。
乾燥処理済みのアルカリ性キトサン:<5EU/g
実施例2
50gのキトサンを、50gの0.1M NaOHと10分間混合した。結果として得られた、湿ったアルカリ性キトサン団粒を、直ちに流動層乾燥機内で40℃で乾燥した。
乾燥処理済みのアルカリ性キトサン:16.3EU/g
実施例3
50gのキトサンを、50gの0.05M NaOHと10分間混合した。結果として得られた、湿ったアルカリ性キトサン団粒を、直ちに流動層乾燥機内で40℃で乾燥した。
乾燥処理済みのアルカリ性キトサン:20.0EU/g
実施例4
50gのキトサンを、50gの0.01M NaOHと10分間混合した。結果として得られた、湿ったアルカリ性キトサン団粒を、直ちに流動層乾燥機内で40℃で乾燥した。
乾燥処理済みのアルカリ性キトサン:<30EU/g
本発明の方法は拡大適用(scale up)することができ、より大きなバッチサイズでの製造も可能である。
低エンドトキシンのアルカリ性キトサンを酸と反応させて、中性のpHを有するキトサンまたはキトサン塩を製造する場合、酸性塩が副産物として生成される。この副産物の存在は、キトサン生成物の性能に影響を与える可能性がある。たとえば、副産物の量によっては生理食塩水中のキトサンの粘度に影響を与えることがある。
本発明の低エンドトキシンのアルカリ性キトサンを試験することにより、酸による処理がキトサン重合体の粘度に与える影響を明らかに示すことができる。ここでは、粘度は分子量の測定単位と考える。試験は次の手順によって行う。
b)600mlのビーカーに4.95gの酢酸を量って入れ、
c)490.05gの脱イオン化水をビーカーに加え、1%の酢酸溶液を495g調製し、
d)ビーカーを撹拌用プレート(stirrer plate)に載せ、攪拌器をオンにし(溶液の粘度が増加するにしたがい、撹拌速度を速くする)、
e)キトサン顆粒を酢酸溶液に加え、
f)顆粒がすべて溶解するまで定期的に溶液を確認し、必要ならば、溶液の粘度が増加するにしたがい、撹拌速度を速くし、
g)キトサン顆粒を酢酸溶液に加えた時点から計測して合計で24時間、溶液を放置し、
h)ブルックフィールド(Brookfield)粘度計にスピンドル64を取り付け、
i)スピンドルを10rpmにセットし、
j)スピンドルに示された目印までスピンドルを溶液に浸し、粘度計をオンにして安定するまで待ち、
k)選んだ時間間隔で、粘度(cPs)を記録する。
本発明の方法において、より低濃度のアルカリ溶液を使用することの効果は、3つの実験により試験することができる。実験では、(1)生理食塩水の試験サンプルへの浸透率、(2)凝血塊が形成される(血液が凝固する)までの時間、および(3)生体モデルでの上腹部断絶における止血割合に焦点を合わせる。
Claims (39)
- 低エンドトキシンのアルカリ性キトサン、キチン、またはこれらの誘導体を製造する方法であって、
(a)キトサン、キチン、キトサン誘導体、またはキチン誘導体をアルカリ溶液と接触させて、混合物を形成する工程と、
(b)前記混合物を1時間未満放置する工程とを含む方法。 - 前記混合物を乾燥させる工程(c)をさらに含む請求項1に記載の方法。
- 前記アルカリ溶液の濃度が約0.01Mから約1Mまでである請求項1または2に記載の方法。
- 前記アルカリ溶液の濃度が約0.02Mから0.25Mまでである請求項3に記載の方法。
- 前記アルカリ溶液の濃度が約0.1Mである請求項4に記載の方法。
- 前記アルカリ溶液と、キトサン、キチン、キトサン誘導体、またはキチン誘導体とが、アルカリ溶液約10部に対してキトサン、キチン、キトサン誘導体、またはキチン誘導体約1部から、アルカリ溶液約1部に対してキトサン、キチン、キトサン誘導体、またはキチン誘導体約10部までの範囲内で存在する、前記いずれか一つの請求項に記載の方法。
- 前記アルカリ溶液が、金属水酸化物、金属炭酸塩、金属重亜硫酸塩、金属過ケイ酸塩、共役塩基、および水酸化アンモニウムから選ばれるアルカリ成分またはアルカリ土類成分を単独でまたは組み合わせて含む、前記いずれか一つの請求項に記載の方法。
- 前記金属が、ナトリウム、カリウム、カルシウム、またはマグネシウムから選ばれる請求項7に記載の方法。
- 前記アルカリ成分が、水酸化ナトリウム、水酸化カリウム、または炭酸ナトリウムから選ばれる請求項7または8に記載の方法。
- 前記アルカリ溶液を前記キトサン、キチン、キトサン誘導体、またはキチン誘導体に対し噴霧するか、または前記キトサン、キチン、キトサン誘導体、またはキチン誘導体を前記アルカリ溶液と混合する、前記いずれか一つの請求項に記載の方法。
- 前記混合物を3分間未満放置する前記いずれか一つの請求項に記載の方法。
- 前記工程(b)が、前記工程(a)に続いて直ちに前記混合物を乾燥させることを含む請求項11に記載の方法。
- 前記混合物を清潔な容器内に放置するか、および/または不活性雰囲気下で放置する、前記いずれか一つの請求項に記載の方法。
- 前記混合物が防腐剤をさらに含む前記いずれか一つの請求項に記載の方法。
- 前記防腐剤が、銀イオン、亜鉛イオン、クロルヘキシジン、またはこれらの組み合わせから選ばれる請求項14に記載の方法。
- 請求項1から15のいずれかに記載の方法によって得られる低エンドトキシンのアルカリ性キトサン、キチン、キトサン誘導体、またはキチン誘導体。
- エンドトキシンの濃度が50EU/g未満であるアルカリ性キトサン、キチン、キトサン誘導体、またはキチン誘導体。
- 請求項1から15のいずれかに記載の方法によって調製されるアルカリ性キトサンを酸と接触させる工程を含む、低エンドトキシンの中性キトサン、キトサン塩、またはキトサン誘導体を製造する方法。
- 前記アルカリ性キトサンを酸と接触させる工程を、請求項2から15のいずれかに記載の前記乾燥工程(c)の前に行う請求項18に記載の方法。
- 前記酸を前記アルカリ性キトサンに対し噴霧するか、または前記アルカリ性キトサンを前記酸と混合する請求項18または19に記載の方法。
- 前記酸が、有機酸、カルボン酸、脂肪酸、アミノ酸、ルイス酸、一塩基酸、二塩基酸、多塩基酸、核酸、および鉱酸から単独でまたは組み合わせて選ばれる請求項18から20のいずれかに記載の方法。
- 前記有機酸が、酢酸、酒石酸、クエン酸、アスコルビン酸、アセチルサリチル酸、グルコン酸、および乳酸から単独でまたは組み合わせて選ばれる請求項21に記載の方法。
- 前記脂肪酸が、ミリストレイン酸、パルミトレイン酸、サピエン酸、オレイン酸、エライジン酸、バクセン酸、リノール酸、リノエライジン酸、α−リノレン酸、アラキドン酸、エイコサペンタエン酸、エルシン酸、ドコサヘキサエン酸、カプリル酸、カプリン酸、ラウリン酸、ミリスチン酸、パルミチン酸、ステアリン酸、アラキジン酸、ベヘン酸、リグノセリン酸、およびセロチン酸から単独でまたは組み合わせて選ばれる請求項21に記載の方法。
- 前記アミノ酸が、ヒスチジン、リシン、アスパラギン酸、グルタミン酸、グルタミン、グリシン、プロリン、およびタウリンから単独でまたは組み合わせて選ばれる請求項21に記載の方法。
- 前記鉱酸が、塩酸、硫酸、および硝酸から単独でまたは組み合わせて選ばれる請求項21に記載の方法。
- 前記酸の濃度が約1Mである請求項18から25のいずれかに記載の方法。
- 前記酸が、前記酸と非溶媒とを含む酸液として存在する請求項18から26のいずれかに記載の方法。
- 前記非溶媒が、乳酸エチル、酢酸エチル、酢酸メチル、エタノール、アセトン、80:20の割合のエタノールと水の混合物、またはこれらの混合物から単独でまたは組み合わせて選ばれる請求項27に記載の方法。
- 酸液に対するキトサンの割合が約5:1から約1:5である請求項27または28に記載の方法。
- 前記アルカリ性キトサンを前記酸と約5分間混合する請求項18から29のいずれかに記載の方法。
- 前記反応物を乾燥させる工程をさらに含む請求項18から30のいずれかに記載の方法。
- 請求項18から31のいずれかに記載の方法により得られる低エンドトキシンの中性キトサン、キトサン塩、またはキトサン誘導体。
- エンドトキシンの濃度が50EU/g未満である中性キトサン、キトサン塩、またはキトサン誘導体。
- 血液の流れを止めることを目的とする請求項32に記載の低エンドトキシンのキトサン塩の使用。
- 血液の流れを止める止血剤として使用する請求項32に記載の低エンドトキシンのキトサン塩。
- 生命に別状のない表部の出血用または生死に関わる出血用の創傷被覆材に使用する請求項32に記載の低エンドトキシンのキトサン塩。
- 請求項32に記載の低エンドトキシンのキトサン塩を含む止血用創傷被覆材。
- 血液の流れを止める方法であって、可能であれば創傷領域を任意に洗浄する工程と、請求項32に記載の低エンドトキシンのキトサン塩を含む止血用創傷被覆材を前記創傷領域に適用する工程と、ゲル状凝血塊が形成されるまで前記創傷領域に一定の圧力を加える工程とを含む方法。
- 本明細書および図面に実質的に記載され示される、低エンドトキシンのアルカリ性キトサン、中性キトサン、キトサン塩、またはキトサン誘導体、あるいはこれらの処理工程または方法。
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JP2022068319A (ja) | 2022-05-09 |
CA2913678C (en) | 2022-01-25 |
BR112015029779A2 (pt) | 2017-07-25 |
JP7288108B2 (ja) | 2023-06-06 |
AU2014272886B2 (en) | 2018-11-15 |
CN105408359A (zh) | 2016-03-16 |
BR112015029779A8 (pt) | 2019-12-24 |
RU2015155299A (ru) | 2017-07-03 |
PL3004180T3 (pl) | 2023-08-07 |
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