JP2010024257A - 生体適合性重合性化合物、生体適合性ポリマー、及び、ポリマー粒子 - Google Patents
生体適合性重合性化合物、生体適合性ポリマー、及び、ポリマー粒子 Download PDFInfo
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- JP2010024257A JP2010024257A JP2008183441A JP2008183441A JP2010024257A JP 2010024257 A JP2010024257 A JP 2010024257A JP 2008183441 A JP2008183441 A JP 2008183441A JP 2008183441 A JP2008183441 A JP 2008183441A JP 2010024257 A JP2010024257 A JP 2010024257A
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- iodine
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- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- DSXQWLYNLIETTE-UHFFFAOYSA-N thiaziridine Chemical compound C1NS1 DSXQWLYNLIETTE-UHFFFAOYSA-N 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/59—Hydrogenated pyridine rings
-
- 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
- C08F30/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F30/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing phosphorus
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
天然の親水性高分子としては、アルギネイト、コラーゲン、ヒアルロン酸、コンドロイチン硫酸、フィブリン、キトサン、又は絹などが挙げられる。これらの高分子は、生体適合性が高いが、生分解性が高く機械強度が弱いという問題がある。また、病原体の混入も懸念される。
しかし、2−メタクロイルオキシエチルホスホリルコリンの水溶性が高いために、合成が煩雑であり、また、2−メタクロイルオキシエチルホスホリルコリンの比率が高いポリマーは親水性が高すぎて水中では粒子を形成せず、また、機械的強度が低いという問題があった。
例えば、リポソームやミセルのような粒子の中に造影剤の薬剤等を内包させ、その粒子の表面をリガンド分子等で修飾することや、ポリマーで薬剤を覆うことが報告されている(特許文献2〜7、非特許文献2〜4)。しかしながら、このような造影剤は安定性が低いこと、安全性が低いこと、粒子の粒径が大きく細網内皮系に捕捉されやすいことなどが造影性能の悪化につながっている。
[1] 下記一般式(I)で示される化合物:
[2]Xが−O(C=O)−である[1]に記載の化合物。
[3]Rが置換又は無置換のアルキル基である[1]又は[2]に記載の化合物。
[4]RがC1−C20の無置換のアルキル基である[3]に記載の化合物。
[5]Rが、置換又は無置換のアリール基である[1]又は[2]に記載の化合物。
[6]Rが、二つ以上のヨウ素原子を少なくとも含む[5]に記載の化合物。
[8]Rが、3つのヨウ素原子で置換されたヨウ素置換フェニル基である[7]に記載の化合物。
[9][1]〜[8]のいずれか一項に記載の化合物を含む重合性化合物の重合反応により得られるポリマー。
[10] 下記一般式(11)で示される構造単位を含むポリマー。
[11]下記一般式(12)で示される構造単位を含むポリマー。
[12] 下記一般式(11)で示される構造単位及び下記一般式(12)で示される構造単位を含むポリマー。
なお、本明細書において「〜」とはその前後に記載される数値を下限値及び上限値として含む意味で使用される。
一般式(I)においてXは、−O−、−S−、−NR2−、又は−O(C=O)−を表す(R2は水素原子、置換もしくは無置換のアルキル基、又は置換もしくは無置換の又はアリール基を表す)。Xは、−O−、−NH−、又は−O(C=O)−であることが好ましく、−O(C=O)−であることがより好ましい。
Rで表されるシクロアルケニル基の総炭素数は、4〜20が好ましく、5〜10がより好ましい。無置換シクロアルケニル基の例としては、シクロヘキセニル基等が挙げられる。Rは上記無置換シクロアルケニル基が置換基を有する置換シクロアルケニル基であってもよい。
反応溶媒(アルコール系、アセトン、メチルエチルケトン、シクロヘキサノン、ジメチルアセトアミド、ジメチルホルムアミド、ジメチルスルホキシド、スルホラン、N-メチルピロリドンなど)にグリシジル(メタ)アクリレートとカルボン酸を加え、さらに必要に応じて触媒(テトラブチルアンモニウムブロミドなどアンモニウム塩)を加えて、50度以上120度以下で加熱反応させて中間体を作製する。
さらに、中間体と2-クロロ−2−オキソ−1,3,2−ジオキサホスホランを反応させて、一般式(I)で表される化合物を得ることができる。この反応は実施例の方法などで適宜行うことができる。反応の際の温度は0度以下、−70度以上であればよい。反応溶媒としては、塩化メチレン、クロロホルム、アセトン、テトラヒドロフラン、ジエチルエーテル、1,2−ジクロロエタン、クロロベンゼンなどを適宜選択して用いればよい。
一般式(I)で表される化合物と一般式(I)で表される化合物以外の化合物とを共重合させる場合の両者のモル比率としては100:0〜20:80が好ましく、100:0〜30:70がより好ましく、100:0〜50:50がさらに好ましい。
下記一般式(12)で示される構造単位を含むポリマー:
例えば、ヨウ素を含む一般式(I)で表される化合物を用いて作製されたポリマー粒子を用いてX線造影剤を作成することが可能である。
また、例えば造影効果を有する成分とともにポリマー粒子を形成することによって生体適合性の高い造影剤を作製することができる。造影効果を有する成分としては、例えば常磁性金属化合物が挙げられる。上記粒子においては、上記ポリマーが造影効果を有する成分を内包していてもよく、上記ポリマーが造影効果を有する成分とともに粒子の膜を形成していてもよい。
(実施例1)
反応容器にグリシジルメタクリレート(東京化成社製)(3質量部)、ドデカン酸(東京化成社製)(4.3質量部)、テトラブチルアンモニウムブロミド(和光純薬社製)(0.7質量部)、及びジメチルアセトアミド(和光純薬社製)(50質量部)を入れた。得られた混合物を、オイルバスで90度に加熱して2時間撹拌した。その後、水300質量部と酢酸エチル(和光純薬社製)80質量部を加えて分液操作を行った。有機溶媒層を飽和食塩水200質量部で洗浄後、硫酸マグネシウムで乾燥した。硫酸マグネシウムを濾過により除去し、有機溶媒を真空留去した。得られた粗生成物をシリカゲルカラムクロマトグラフィーで精製し、オイル状中間体1Aを5.4質量部(収率75%)得た。
1H−NMR(300 MHz)CDCl3
6.11 (s, 1H), 5.58 (s, 1H), 4.65-4.50 (m, 1H), 4.40-4.24 (m, 6H), 3.75 (s, 2H), 3.35 (s, 9H), 2.30 (t, 2H), 1.91 (s, 3H), 1.60 (t, 2H), 1.35-1.20 (m, 16H), 0.89 (t, 3H)
反応容器にグリシジルメタクリレート(東京化成社製)(3質量部)、パルチミン酸(東京化成社製)(5.4質量部)、テトラブチルアンモニウムブロミド(和光純薬社製)(0.7質量部)、及びジメチルアセトアミド(和光純薬社製)(50質量部)を入れた。得られた混合物を、オイルバスで90度に加熱して2時間撹拌した。その後、水(300質量部)及び酢酸エチル(和光純薬社製)(80質量部)を加えて分液操作を行った。有機溶媒層を飽和食塩水(200質量部)で洗浄後、硫酸マグネシウムで乾燥した。硫酸マグネシウムを濾過により除去し、有機溶媒を真空留去した。得られた粗生成物をシリカゲルカラムクロマトグラフィーで精製し、オイル状中間体2Aを4.6質量部(収率55%)得た。
1H−NMR(300 MHz)CDCl3
6.11 (s, 1H), 5.58 (s, 1H), 4.65-4.50 (m, 1H), 4.40-4.24 (m, 6H), 3.75 (s, 2H), 3.35 (s, 9H), 2.30 (t, 2H), 1.91 (s, 3H), 1.60 (t, 2H), 1.35-1.20 (m, 24H), 0.89 (t, 3H)
反応容器に、グリシジルメタクリレート(東京化成社製)(3質量部)、2,3,5−トリヨード安息香酸(東京化成社製)(10.6質量部)、テトラブチルアンモニウムブロミド(和光純薬社製)(0.7質量部)、及びジメチルアセトアミド(和光純薬社製)(50質量部)を入れた。得られた混合物を、オイルバスで90度に加熱して2時間撹拌した。その後、水(300質量部)及び酢酸エチル(和光純薬社製)(80質量部)を加えて分液操作を行った。有機溶媒層を飽和食塩水(200質量部)で洗浄後、硫酸マグネシウムで乾燥した。硫酸マグネシウムを濾過により除去し、有機溶媒を真空留去した。得られた粗生成物をシリカゲルカラムクロマトグラフィーで精製し、オイル状中間体3Aを10.9質量部(収率80%)得た。
1H−NMR(300 MHz)CDCl3
8.25 (s, 1H), 7.76 (s, 1H), 6.11 (s, 1H), 5.58 (s, 1H), 4.75-4.28 (m, 7H), 3.75 (s, 2H), 3.30 (s, 9H), 1.91 (s, 3H)
反応容器にグリシジルメタクリレート(東京化成社製)(3質量部)、アセトリゾン酸
(CAS 85-36-9)(東京化成社製)(11.8質量部)、テトラブチルアンモニウムブロミド(和光純薬社製)(0.7質量部)、及びジメチルアセトアミド(和光純薬社製)(50質量部)を入れた。オイルバスで90度に加熱して2時間撹拌した。その後、水(300質量部)及び酢酸エチル(和光純薬社製)(80質量部)を加えて分液操作を行った。有機溶媒層を飽和食塩水(200質量部)で洗浄後、硫酸マグネシウムで乾燥した。硫酸マグネシウムを濾過により除去し、有機溶媒を真空留去した。得られた粗生成物をシリカゲルカラムクロマトグラフィーで精製し、オイル状中間体4Aを9.4質量部(収率64%)得た。
1H−NMR(300 MHz)CDCl3
8.25 (s, 1H), 7.90 (br, 1H), 6.11 (s, 1H), 5.58 (s, 1H), 4.75-4.28 (m, 7H), 3.75 (s, 2H), 2.17 (s, 3H), 1.91 (s, 3H)
反応容器に、具体的化合物例3(3質量部)、ステアリルメタクリレート(東京化成社製)(1.8質量部)、n−プロパノール(和光純薬社製)2質量部、及びV−601(和光純薬社製)0.002質量部を入れた。窒素雰囲気下にし、内温を80度で8時間撹拌した。反応終了後、反応溶液をアセトン(100質量部)にゆっくりと入れ、白色固体2.6質量部を得た。
この白色固体0.1質量部をn−プロパノール(和光純薬社製)0.4質量部に溶解させ、60度に加熱した状態で純水1.6質量部を加えた。その後20分間撹拌し、ポリマー粒子分散液を得た。この分散液に存在するポリマー粒子の平均粒径は、粒径測定器(日機装社製UPA-EX150)を用いて測定したところ、153nmであった。
反応容器に具体的化合物例28(0.025質量部)、n−プロパノール(和光純薬社製)(0.5質量部)、純水(9.5質量部)、及びV−601(和光純薬社製)(0.002質量部)を入れた。窒素雰囲気下にし、内温を80度で8時間撹拌した。得られた反応溶液をゲル濾過(PD-10 columns:GEヘルスケア製)し、ポリマー粒子分散液を得た。このポリマー粒子分散液におけるポリマー粒子の平均粒径は、粒径測定器(日機装社製UPA-EX150)を用いて測定したところ、101nmであった。
Claims (12)
- Xが−O(C=O)−である請求項1に記載の化合物。
- Rが置換又は無置換のアルキル基である請求項1又は2に記載の化合物。
- RがC1−C20の無置換のアルキル基である請求項3に記載の化合物。
- Rが、置換又は無置換のアリール基である請求項1又は2に記載の化合物。
- Rが、二つ以上のヨウ素原子を少なくとも含む請求項5に記載の化合物。
- Rが、二つ以上のヨウ素原子を少なくとも含むヨウ素置換フェニル基であり、該ヨウ素置換フェニル基は、アミノ基、カルボキシル基、ハロゲン原子、-NR3(C=O)R4、-(C=O)OR5、-(C=O)NR6R7(R3〜R7は水素原子、置換もしくは無置換のアルキル基置換もしくは無置換の又はアリール基を表す)、置換もしくは無置換のアルキル基、及び置換もしくは無置換のアリール基からなる群から選択される置換基で置換されていてもよい請求項5に記載の化合物。
- Rが、3つのヨウ素原子で置換されたヨウ素置換フェニル基である請求項7に記載の化合物。
- 請求項1〜8のいずれか一項に記載の化合物を含む重合性化合物の重合反応により得られるポリマー。
- 下記一般式(11)で示される構造単位及び下記一般式(12)で示される構造単位を含むポリマー。
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JP2008115282A (ja) * | 2006-11-06 | 2008-05-22 | Konica Minolta Holdings Inc | ヨウド原子含有ポリマー及びx線用造影剤 |
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US5019370A (en) | 1989-07-10 | 1991-05-28 | University Of Kentucky Research Foundation | Biodegradable, low biological toxicity radiographic contrast medium and method of x-ray imaging |
US5686061A (en) | 1994-04-11 | 1997-11-11 | The Board Of Regents Of The University Of Texas System | Particulate contrast media derived from non-ionic water soluble contrast agents for CT enhancement of hepatic tumors |
JP2870727B2 (ja) | 1996-07-04 | 1999-03-17 | 科学技術振興事業団 | 2−メタクリロイルオキシエチルホスホリルコリン共重合体 |
EP1866155A2 (en) | 2005-04-05 | 2007-12-19 | Bar-Ilan University | New core and core-shell nanoparticles containing iodine for x-ray imaging |
US20070098642A1 (en) | 2005-11-02 | 2007-05-03 | General Electric Company | Nanoparticle-based imaging agents for X-ray/computed tomography |
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JPS60204791A (ja) * | 1984-03-30 | 1985-10-16 | Mitsubishi Chem Ind Ltd | リン脂質類似モノマ−の製造方法 |
JPH06506494A (ja) * | 1991-04-12 | 1994-07-21 | イェック, ユリアーネ | 工業材料 |
JPH07502053A (ja) * | 1991-07-05 | 1995-03-02 | バイオコンパテイブルズ・リミテツド | ポリマーの表面コーティング |
JPH08325203A (ja) * | 1994-05-30 | 1996-12-10 | Ivoclar Ag | X線不透過性歯科用材料 |
JP2002529484A (ja) * | 1998-11-13 | 2002-09-10 | バイオコンパテイブルズ・リミテツド | ポリマーの治療的使用 |
JP2008115282A (ja) * | 2006-11-06 | 2008-05-22 | Konica Minolta Holdings Inc | ヨウド原子含有ポリマー及びx線用造影剤 |
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WO2017169445A1 (ja) * | 2016-03-28 | 2017-10-05 | 国立大学法人大阪大学 | 重原子化化合物、膜タンパク質の結晶化を促進するための組成物、および該組成物を用いた膜タンパク質の構造解析方法 |
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US7964683B2 (en) | 2011-06-21 |
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