JPS6317463B2 - - Google Patents
Info
- Publication number
- JPS6317463B2 JPS6317463B2 JP59172072A JP17207284A JPS6317463B2 JP S6317463 B2 JPS6317463 B2 JP S6317463B2 JP 59172072 A JP59172072 A JP 59172072A JP 17207284 A JP17207284 A JP 17207284A JP S6317463 B2 JPS6317463 B2 JP S6317463B2
- Authority
- JP
- Japan
- Prior art keywords
- film
- polyglutamic acid
- blood
- acid derivative
- cells
- 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
Links
- 108010020346 Polyglutamic Acid Proteins 0.000 claims description 15
- 239000008280 blood Substances 0.000 claims description 13
- 210000004369 blood Anatomy 0.000 claims description 13
- 229920002643 polyglutamic acid Polymers 0.000 claims description 13
- 150000001414 amino alcohols Chemical class 0.000 claims description 9
- 210000004027 cell Anatomy 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 230000021164 cell adhesion Effects 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 238000004381 surface treatment Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 230000017531 blood circulation Effects 0.000 description 2
- DHQUQYYPAWHGAR-UHFFFAOYSA-N dibenzyl 2-aminopentanedioate Chemical compound C=1C=CC=CC=1COC(=O)C(N)CCC(=O)OCC1=CC=CC=C1 DHQUQYYPAWHGAR-UHFFFAOYSA-N 0.000 description 2
- 229920000370 gamma-poly(glutamate) polymer Polymers 0.000 description 2
- -1 polytetrafluoroethylene Polymers 0.000 description 2
- 229920002379 silicone rubber Polymers 0.000 description 2
- 239000004945 silicone rubber Substances 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- MXZROAOUCUVNHX-UHFFFAOYSA-N 2-Aminopropanol Chemical compound CCC(N)O MXZROAOUCUVNHX-UHFFFAOYSA-N 0.000 description 1
- 238000000944 Soxhlet extraction Methods 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 238000007098 aminolysis reaction Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000002473 artificial blood Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- YEJSPQZHMWGIGP-UHFFFAOYSA-N dl-glutamic acid dimethyl ester Natural products COC(=O)CCC(N)C(=O)OC YEJSPQZHMWGIGP-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 210000002919 epithelial cell Anatomy 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- SEWIYICDCVPBEW-UHFFFAOYSA-N methyl glutamate Chemical compound COC(=O)C(N)CCC(O)=O SEWIYICDCVPBEW-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012758 nuclear staining Methods 0.000 description 1
- 239000008363 phosphate buffer Substances 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
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
Landscapes
- Materials For Medical Uses (AREA)
Description
(a) 発明の技術分野
本発明は、アミノアルコールで表面処理された
ポリグルタミン酸誘導体を内表面に有することに
より、細胞が付着しにくいことを特徴とする血液
導管に関するものである。
血液導管とは人工血管、カテーテル、シヤント
（血液を体外に導き出すために用いるもの）、透析
型人工腎臓、膜型人工肺、人工心臓などに用いら
れている管状の血液の流路を包含するものであ
る。
(b) 従来技術の説明
従来、血液導管は、シリコーンゴム、ポリウレ
タン、ポリテトラフルオロエチレン等の合成高分
子材料を用いて作製されているが、これらの材料
を用いた血液導管では、その材料表面に細胞が付
着し、すなわち血栓が生じ、血流を阻害する。し
たがつて、血液導管においては細胞の付着しない
材料が求められている。
(c) 発明の目的
本発明は上記の問題を、アミノアルコールで表
面処理されたポリグルタミン酸誘導体を用いるこ
とにより、細胞付着性の少ない血液導管を提供す
ることを目的とする。
(d) 発明の構成
本発明者は細胞の付着しにくい性質を有する材
料について種々研究を重ねたところ、アミノアル
コールで表面処理されたポリグルタミン酸誘導体
は、細胞を著しく付着させない性質を有してお
り、血液導管として好適であることを見い出し、
本発明を完成するに到つた。
即ち、本発明の血液導管は、ポリグルタミン酸
誘導体を目的とする管状に成型した後、その管状
物をアミノアルコールで表面処理して得るか、あ
るいはあらかじめ他の高分子材料で管状に成型し
た後、その内表面にポリグルタミン酸誘導体を塗
布した後、アミノアルコールで表面処理して得
る。
本発明のポリグルタミン酸誘導体は、Ｄ体、Ｌ
体、ラセミ体でもよく、ポリグルタミン酸誘導体
として、ポリグルタミン酸メチル、ポリグルタミ
ン酸ベンジルなどの脂肪族炭化水素及び芳香族炭
化水素のエステルなどが用いられる。ポリグルタ
ミン酸誘導体の分子量はその皮膜が形成される程
度であればよい。
アミノアルコールとして、エタノールアミン、
アミノプロパノールなどの他、
H2NC2H4OC2H4OHなどのアルキレングリコー
ル誘導体などが用いられる。表面処理時間はアミ
ノアルコールの種類・濃度及びポリグルタミン酸
誘導体の種類に応じて適宜選択するが、いずれに
しても表面処理により、管状物の内表面の水に対
する接触角が45゜以下になるのが望ましい。
(e) 発明の実施例
次に本発明を実施例によりさらに詳細に説明す
る。
実施例 １
グルタミン酸ベンジル単独重合体のジオキサン
溶液をガラス板上に流延し、風乾して皮膜（膜厚
約0.05mm）を得た。この皮膜をエタノールでソツ
クスレー抽出を行つた後、乾燥した。
この皮膜を３―アミノ―１―プロパノール中55
℃で４時間アミノリシス反応させた。反応後エタ
ノールで皮膜を洗浄した。この皮膜を80℃以上の
熱水中に８時間以上浸漬し、乾燥して表面処理皮
膜を得た。この表面処理皮膜の水に対する接触角
を第１表に示す。
(a) Technical Field of the Invention The present invention relates to a blood conduit characterized by having a polyglutamic acid derivative surface-treated with amino alcohol on its inner surface, thereby making it difficult for cells to adhere to the conduit. Blood conduits include tubular blood flow paths used in artificial blood vessels, catheters, shunts (used to lead blood out of the body), dialysis-type artificial kidneys, membrane-type oxygenators, artificial hearts, etc. It is. (b) Description of the prior art Conventionally, blood conduits have been made using synthetic polymer materials such as silicone rubber, polyurethane, and polytetrafluoroethylene. Cells attach to the bloodstream, forming a blood clot, which obstructs blood flow. Therefore, materials to which cells do not adhere are required for blood conduits. (c) Object of the Invention The object of the present invention is to solve the above problem by providing a blood conduit with less cell adhesion by using a polyglutamic acid derivative surface-treated with amino alcohol. (d) Structure of the Invention The present inventor has conducted various studies on materials that have properties that make it difficult for cells to adhere to them, and has found that polyglutamic acid derivatives surface-treated with amino alcohol have properties that do not allow cells to adhere to a large extent. , found that it is suitable as a blood conduit,
The present invention has now been completed. That is, the blood conduit of the present invention is obtained by molding a polyglutamic acid derivative into a desired tubular shape and then surface-treating the tubular material with amino alcohol, or by molding the polyglutamic acid derivative into a tubular shape in advance with other polymeric materials, After applying a polyglutamic acid derivative to its inner surface, it is obtained by surface treatment with amino alcohol. The polyglutamic acid derivative of the present invention is D-form, L-form
The polyglutamic acid derivatives may include esters of aliphatic hydrocarbons and aromatic hydrocarbons such as methyl polyglutamate and benzyl polyglutamate. The molecular weight of the polyglutamic acid derivative is sufficient as long as it forms a film. As amino alcohol, ethanolamine,
In addition to aminopropanol,
Alkylene glycol derivatives such as H 2 NC 2 H 4 OC 2 H 4 OH are used. The surface treatment time is appropriately selected depending on the type and concentration of the amino alcohol and the type of polyglutamic acid derivative, but in any case, the surface treatment should reduce the contact angle of the inner surface of the tubular object to water to 45° or less. desirable. (e) Examples of the invention Next, the present invention will be explained in more detail using examples. Example 1 A dioxane solution of benzyl glutamate homopolymer was cast onto a glass plate and air-dried to obtain a film (film thickness: approximately 0.05 mm). This film was subjected to Soxhlet extraction with ethanol and then dried. This film was dissolved in 3-amino-1-propanol at 55%
Aminolysis reaction was carried out at ℃ for 4 hours. After the reaction, the film was washed with ethanol. This film was immersed in hot water of 80°C or higher for 8 hours or more and dried to obtain a surface-treated film. Table 1 shows the contact angle of this surface treated film with water.
【表】
実施例 ２
グルタミン酸ベンジル単独重合体のジオキサン
溶液のかわりにグルタミン酸メチル単独重合体の
ジクロルエタン溶液を用いた以外は実施例１と同
様にして表面処理皮膜を得た。
実施例 ３
実施例１で得た皮膜上で、人由来の上皮性細胞
を含む培養液（約10万個／ml）を接触させたま
ま、炭酸ガス濃度５％、湿度100％、37℃の部屋
に静置した。17時間後、皮膜をリン酸緩衝液でか
るく洗浄し、皮膜上に付着している細胞の量を核
染色法により定量した。比較のため、血液導管に
使用されているシリコーンゴム、標準試料として
市販の細胞培養シートを用いて、同様の細胞付着
試験を行つた。皮膜に付着した細胞の量を、標準
試料に付着した細胞の量で割ることにより、細胞
付着率を求め、その結果を第２表に示す。[Table] Example 2 A surface treated film was obtained in the same manner as in Example 1, except that a dichloroethane solution of methyl glutamate homopolymer was used instead of the dioxane solution of benzyl glutamate homopolymer. Example 3 A culture solution containing human-derived epithelial cells (approximately 100,000 cells/ml) was placed on the film obtained in Example 1 at a temperature of 5% carbon dioxide gas concentration, 100% humidity, and 37°C. I left it in the room. After 17 hours, the film was gently washed with phosphate buffer, and the amount of cells adhering to the film was quantified by nuclear staining. For comparison, a similar cell adhesion test was conducted using silicone rubber used for blood conduits and a commercially available cell culture sheet as a standard sample. The cell attachment rate was determined by dividing the amount of cells attached to the film by the amount of cells attached to the standard sample, and the results are shown in Table 2.
【表】
実施例 ４
３―アミノ―１―プロパノール中55℃で４時間
の処理のかわりにH2NC2H4OC2H4OH中60℃で
４時間の処理を行つた以外は実施例１と同様にし
て表面処理皮膜を得た。
実施例 ５
ガラス管の内表面にポリグルタミン酸誘導体を
塗布し、乾燥させたのち、３―アミノ―１―プロ
パノール中55℃で４時間処理し、エタノールで洗
浄したのち、さらに80℃以上の熱水中に８時間以
上浸漬させ、乾燥後ガラス管からはずし、管状物
を得た。
(f) 発明の効果
本発明は以上説明したように、細胞付着性の少
ないことを必要とする血液導管において、アミノ
アルコールで表面処理されたポリグルタミン酸誘
導体を内表面に成型することにより細胞の付着を
抑え、かつ、この血液導管を任意の形状で得るこ
とが可能である。[Table] Example 4 Example except that instead of treatment in 3-amino-1-propanol at 55°C for 4 hours, treatment in H 2 NC 2 H 4 OC 2 H 4 OH at 60°C for 4 hours was performed. A surface treated film was obtained in the same manner as in Example 1. Example 5 A polyglutamic acid derivative was applied to the inner surface of a glass tube, dried, treated in 3-amino-1-propanol at 55°C for 4 hours, washed with ethanol, and further heated with hot water at 80°C or higher. The tube was immersed in the glass for 8 hours or more, and after drying, it was removed from the glass tube to obtain a tube. (f) Effects of the Invention As explained above, the present invention improves cell adhesion by molding a polyglutamic acid derivative surface-treated with amino alcohol on the inner surface of a blood conduit that requires low cell adhesion. It is possible to obtain this blood conduit in any shape while suppressing the amount of the blood conduit.
Claims (1)
タミン酸誘導体を内表面に有する血液導管。1 A blood conduit having a polyglutamic acid derivative surface-treated with amino alcohol on its inner surface.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59172072A JPS6150562A (en) | 1984-08-17 | 1984-08-17 | Blood conduit |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59172072A JPS6150562A (en) | 1984-08-17 | 1984-08-17 | Blood conduit |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6150562A JPS6150562A (en) | 1986-03-12 |
| JPS6317463B2 true JPS6317463B2 (en) | 1988-04-13 |
Family
ID=15935019
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59172072A Granted JPS6150562A (en) | 1984-08-17 | 1984-08-17 | Blood conduit |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6150562A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0458159A (en) * | 1990-06-27 | 1992-02-25 | Sharp Corp | Multiprober |
-
1984
- 1984-08-17 JP JP59172072A patent/JPS6150562A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0458159A (en) * | 1990-06-27 | 1992-02-25 | Sharp Corp | Multiprober |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6150562A (en) | 1986-03-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |