JP4220513B2 - カチオン化ヒアルロン酸 - Google Patents
カチオン化ヒアルロン酸 Download PDFInfo
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- JP4220513B2 JP4220513B2 JP2005347501A JP2005347501A JP4220513B2 JP 4220513 B2 JP4220513 B2 JP 4220513B2 JP 2005347501 A JP2005347501 A JP 2005347501A JP 2005347501 A JP2005347501 A JP 2005347501A JP 4220513 B2 JP4220513 B2 JP 4220513B2
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- hyaluronic acid
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- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 title claims description 71
- 229920002674 hyaluronan Polymers 0.000 title claims description 69
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- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 5
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- 229910052740 iodine Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
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- 229950006780 n-acetylglucosamine Drugs 0.000 description 1
- YQFOHQBSENCNTR-UHFFFAOYSA-M oxiran-2-ylmethyl(tripropyl)azanium;chloride Chemical compound [Cl-].CCC[N+](CCC)(CCC)CC1CO1 YQFOHQBSENCNTR-UHFFFAOYSA-M 0.000 description 1
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- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
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- QVOJVKONBAJKMA-UHFFFAOYSA-M triethyl(oxiran-2-ylmethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1CO1 QVOJVKONBAJKMA-UHFFFAOYSA-M 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
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- 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
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- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
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- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
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- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
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- 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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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
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Description
例えば、特許文献1には、ヒアルロン酸ゲル表面にカチオン性物質によるポリイオンコンプレックス膜を形成した薬剤内包ヒアルロン酸ゲルカプセルが記載されている。
また、特許文献2には、ヒアルロン酸とカチオン性ポリアクリル酸誘導体とのポリイオンコンプレックスを製剤用担体として用いた徐放性製剤が記載されている。
また、医療用接着材や固定材、癒着防止材など医療用材料への適用も報告されている(特許文献3〜5)。
生体素材由来のカチオン性ポリマーとしては、キチンの脱アセチル化物であるキトサンやアミノ化セルロースなどが知られているが、より人体成分に近いものが求められていた。
すなわち、本発明にかかるカチオン化ヒアルロン酸は、ヒアルロン酸の水酸基の水素原子の少なくとも一部が、4級アンモニウムカチオン基を有する基で置換されたことを特徴とする。
本発明のカチオン化ヒアルロン酸は、下記一般式(1)で示される。
本発明のカチオン化ヒアルロン酸の好適な例として、前記一般式(1)で示される構造を有するものが挙げられる。
一般式(2)において、R1は炭素数3〜5のアルキレン基であるが、水酸基を有していてもよく、好適な例としては−CH2CH(OH)CH2−が挙げられる。
R2、R3及びR4はそれぞれ炭素数1〜3のアルキル基を示す。
nは重合度を示す正の整数である。ヒアルロン酸の分子量は特に制限されないが、通常は10〜300万程度のものが使用される。
原料となるヒアルロン酸の製造方法は特に制限されない。ヒアルロン酸は、例えば、鶏冠のトサカなどの生体組織からの抽出、あるいは微生物を用いた培養などにより工業的に生産されており、その塩(ナトリウム塩など)も市販されている。本発明においては、ヒアルロン酸あるいはその塩を用いることができる。
一般式(3)において、R2、R3及びR4は、それぞれ炭素数1〜3のアルキル基である。Xはハロゲン原子であり、Cl、Br、Iなどが挙げられるが、好ましくはClである。具体例としては、グリシジルトリメチルアンモニウムクロライド、グリシジルトリエチルアンモニウムクロライド、グリシジルトリプロピルアンモニウムクロライドなどが挙げられる。
反応温度は、原料や目的とする置換度に応じて適宜設定されるが、通常20〜50℃、好ましくは25〜40℃である。高温ではヒアルロン酸の加水分解が進行して低分子化することがあるので、低分子化を望まない場合には注意を要する。
カチオン化ヒアルロン酸とヒアルロン酸の混合比は、ポリイオンコンプレックスを形成する範囲であれば特に制限されず、目的に応じて適宜決定することができる。
また、目的や用途によっては、本発明のカチオン化ヒアルロン酸を他のアニオン性物質とのポリイオンコンプレックス形成に用いることも可能である。他のアニオン性物質としては分子内に複数のアニオン性基(例えば、カルボキシル基、硫酸基など)を有し、カチオン化ヒアルロン酸と水存在下でポリイオンコンプレックスを形成するものであれば制限されない。
以下、実施例を挙げて本発明を具体的に説明するが、本発明はこれらに限定されるものではない。
グリシジルトリメチルアンモニウムクロライド10.4mL(0.078mol)を水11.25mLと混合し、ヒアルロン酸(商品名:バイオヒアロ9、(株)資生堂製)5g(二糖ユニットとして0.013mol)、及び2M水酸化ナトリウム水溶液1.25mLを加えて溶解した。
この混合液を、室温で3日間反応させた。反応後、メタノールを加えて反応物を沈殿させ、アセトンで十分に洗浄し、白色粉末4.2gを得た。
得られた粉末について、GPCで低分子化合物(未反応試薬)が除去されていることを確認した。
また、1H−NMR(図1参照)で構造確認したところ、トリメチルアンモニウムのプロトンに由来するシグナルが検出され、2−ヒドロキシ−3−トリメチルアンモニウムプロピル基が導入されていることを確認した。
また、平均置換度は、1H−NMRの積分値から、ヒアルロン酸1ユニット当たり約1.4であった。
製造例1で得られたカチオン化ヒアルロン酸の1%(w/w)水溶液を調製した。別に、ヒアルロン酸(商品名:バイオヒアロ12、(株)資生堂製)の1%(w/w)水溶液を調製した。
両水溶液は何れも透明の液体であったが、これらを等量混合したところ、ゲル状の沈殿を生じた。このゲルは、カチオン化ヒアルロン酸のカチオン基と、ヒアルロン酸のアニオン基とがイオン対を形成したポリイオンコンプレックスであると考えられる。
製造例1で得られたカチオン化ヒアルロン酸の1%(w/w)水溶液を調製した。別に、カルボキシビニルポリマーの0.1%(w/w)水溶液を調製した。
両水溶液は何れも透明の液体であったが、これらを等量混合したところ、ゲル状の沈殿を生じた。このゲルは、カチオン化ヒアルロン酸のカチオン基と、カルボキシビニルポリマーのアニオン基とがイオン対を形成したポリイオンコンプレックスであると考えられる。
Claims (4)
- 請求項1又は2記載のカチオン化ヒアルロン酸と、アニオン性生体適合性素材とから形成されたことを特徴とするポリイオンコンプレックス。
- 請求項3記載のポリイオンコンプレックスにおいて、アニオン性生体適合性素材がヒアルロン酸であることを特徴とするポリイオンコンプレックス。
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US12/095,195 US20090281056A1 (en) | 2005-12-01 | 2006-11-17 | Cationized Hyaluronic Acid |
ES06832873T ES2409065T3 (es) | 2005-12-01 | 2006-11-17 | Ácido hialurónico cationizado |
EP06832873.1A EP1961772B1 (en) | 2005-12-01 | 2006-11-17 | Cationized hyaluronic acid |
PCT/JP2006/322995 WO2007063725A1 (ja) | 2005-12-01 | 2006-11-17 | カチオン化ヒアルロン酸 |
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KR101347961B1 (ko) | 2014-01-07 |
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CN101316864A (zh) | 2008-12-03 |
EP1961772A4 (en) | 2011-08-03 |
US20090281056A1 (en) | 2009-11-12 |
EP1961772A1 (en) | 2008-08-27 |
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