JPS6352905B2 - - Google Patents
Info
- Publication number
- JPS6352905B2 JPS6352905B2 JP59205217A JP20521784A JPS6352905B2 JP S6352905 B2 JPS6352905 B2 JP S6352905B2 JP 59205217 A JP59205217 A JP 59205217A JP 20521784 A JP20521784 A JP 20521784A JP S6352905 B2 JPS6352905 B2 JP S6352905B2
- Authority
- JP
- Japan
- Prior art keywords
- leucine
- tube
- skin
- copolymer
- film
- 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
- 229920001577 copolymer Polymers 0.000 claims description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 210000004027 cell Anatomy 0.000 description 11
- 150000001414 amino alcohols Chemical group 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 6
- 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 5
- 229960003136 leucine Drugs 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000021164 cell adhesion Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 229920002379 silicone rubber Polymers 0.000 description 2
- 239000004945 silicone rubber Substances 0.000 description 2
- HFZKKJHBHCZXTQ-JTQLQIEISA-N (4s)-4-azaniumyl-5-oxo-5-phenylmethoxypentanoate Chemical compound OC(=O)CC[C@H](N)C(=O)OCC1=CC=CC=C1 HFZKKJHBHCZXTQ-JTQLQIEISA-N 0.000 description 1
- MXZROAOUCUVNHX-UHFFFAOYSA-N 2-Aminopropanol Chemical compound CCC(N)O MXZROAOUCUVNHX-UHFFFAOYSA-N 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- 235000019454 L-leucine Nutrition 0.000 description 1
- 239000004395 L-leucine Substances 0.000 description 1
- 238000000944 Soxhlet extraction Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229940024606 amino acid Drugs 0.000 description 1
- -1 aromatic amino alcohols Chemical class 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood 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
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 210000000959 ear middle Anatomy 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 210000002919 epithelial cell Anatomy 0.000 description 1
- 210000000981 epithelium Anatomy 0.000 description 1
- 150000002308 glutamine derivatives Chemical class 0.000 description 1
- 238000001631 haemodialysis Methods 0.000 description 1
- 230000000322 hemodialysis Effects 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- LVCDXCQFSONNDO-UHFFFAOYSA-N n-benzylhydroxylamine Chemical compound ONCC1=CC=CC=C1 LVCDXCQFSONNDO-UHFFFAOYSA-N 0.000 description 1
- 238000012758 nuclear staining Methods 0.000 description 1
- 125000000963 oxybis(methylene) group Chemical group [H]C([H])(*)OC([H])([H])* 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 230000035484 reaction time Effects 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変性されたロイ
シン−グルタミン酸ベンジル共重合体を外表面に
有することにより、細胞が付着しやすいことを特
徴とする皮膚貫通管に関するものである。
皮膚貫通管とは、血液、輸液、透析液、電気な
どを体外へ導出あるいは体内へ導入するために用
いられる管状物で、長期間にわたり皮膚を貫通し
て使用するものである。例えば、血液透析におけ
る外シヤント、カテーテル、腹膜透析用チユー
ブ、人工中耳のための電気コードなどを包含する
ものである。
(b) 従来技術の説明
従来、皮膚貫通管はシリコーンゴム、ポリウレ
タン、ポリ塩化ビニル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皮膚
貫通管では、その材料表面に細胞が付着しにく
く、すなわち管の外表面と皮膚の上皮組織とが密
着せず、この部分で菌感染が起こる。したがつ
て、皮膚貫通管においては細胞が付着する材料が
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変
性されたロイシン−グルタミン酸ベンジル共重合
体を用いることにより、細胞付着性の多い皮膚貫
通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やすい性質を有する材
料について種々研究を重ねたところ、アミノアル
コールで変性されたロイシン−グルタミン酸ベン
ジル共重合体は、細胞を多量に付着させる性質を
有しており、皮膚貫通管として好適であることを
見い出し、本発明を完成させるに到つた。
即ち、本発明の皮膚貫通管は、ロイシン−グル
タミン酸ベンジル共重合体を目的とする管状に成
型した後、その成型物をアミノアルコールで変性
させて得るか、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、その外表面に本発明のロ
イシン−グルタミン酸ベンジル共重合体を塗布
し、その後アミノアルコールで変性させて得る。
本発明の共重合体構成材料としてのロイシン及
びグルタミン酸ベンジルはＤ体、Ｌ体、ラセミ体
でもよい。アミノ酸共重合体の分子量はその皮膜
が形成される程度であればよく、また共重合体中
のグルタミン酸ベンジルの含量は５モル％から50
モル％が好ましい。変性剤としてのアミノアルコ
ールには、エタノールアミン、プロパノールアミ
ン、ヒドロキシベンジルアミンなどの脂肪族、あ
るいは芳香族のアミノアルコールの外、H2N
（C2H4O）2Hなどアミノ化ポリエチレングリコー
ルなども用いられる。アミノアルコールと共重合
体との反応時間はアミノアルコールの種類と濃
度、温度、及び共重合体組成に応じて適当に選定
するが、いずれにしても反応により、管状物の表
面部分のグルタミン酸ベンジル成分の一部分は、
グルタミン誘導体に変換されるのが望ましい。
(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
Ｌ−ロイシンとＬ−グルタミン酸ベンジルとの
共重合体（ロイシンとグルタミン酸ベンジルとの
モル比＝７：３）のベンゼン溶液をガラス板上に
流延し、風乾して皮膜（膜厚0.15mm）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
パノール中に浸漬し、60℃で80時間反応させ、エ
タノールで十分に洗浄後乾燥して膜を得た。３−
アミノ−１−プロパノールとの反応前後の膜の全
反射赤外吸収スペクトルの変化を比べると1730、
750、700cm-1のピーク強度が反応後減少した。
この皮膜上で、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、ロイシン−グルタミン酸
ベンジル共重合体皮膜及び皮膚貫通管に使用され
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
求めた。その結果を第１表に示す。
(a) Technical Field of the Invention The present invention relates to a skin-penetrating tube that is characterized by having a leucine-benzyl glutamate copolymer modified with amino alcohol on its outer surface, thereby making it easier for cells to adhere to the tube. A skin-penetrating tube is a tubular object used to lead blood, infusion, dialysate, electricity, etc. out of the body or into the body, and is used by penetrating the skin for a long period of time. Examples include external shunts for hemodialysis, catheters, tubes for peritoneal dialysis, electrical cords for middle ear implants, and the like. (b) Description of the prior art Conventionally, skin-penetrating tubes have been made using synthetic polymer materials such as silicone rubber, polyurethane, and polyvinyl chloride. It is difficult for cells to adhere to the tube, which means that the outer surface of the tube and the epithelial tissue of the skin do not come into close contact, and bacterial infection occurs in this area. Therefore, there is a need for materials to which cells can adhere in skin-penetrating tubes. (c) Object of the Invention The object of the present invention is to solve the above problem by providing a skin-penetrating tube with high cell adhesion by using a leucine-benzyl glutamate copolymer modified with amino alcohol. (d) Structure of the Invention The present inventor has conducted various studies on materials that have properties that allow cells to easily adhere to them, and has found that a leucine-benzyl glutamate copolymer modified with amino alcohol has the property of allowing a large amount of cells to adhere to it. The present inventors have discovered that the present invention is suitable for use as a skin-penetrating tube, and have completed the present invention. That is, the skin-penetrating tube of the present invention can be obtained by molding a leucine-benzyl glutamate copolymer into a desired tube shape and then denaturing the molded product with amino alcohol, or by forming the tube in advance with another polymeric material into a tube shape. After molding, the leucine-benzyl glutamate copolymer of the present invention is coated on the outer surface of the mold, and the mold is then modified with amino alcohol. Leucine and benzyl glutamate as constituent materials of the copolymer of the present invention may be D-form, L-form, or racemic form. The molecular weight of the amino acid copolymer may be sufficient to form a film, and the content of benzyl glutamate in the copolymer may range from 5 mol% to 50% by mole.
Mol% is preferred. Amino alcohols as denaturing agents include aliphatic or aromatic amino alcohols such as ethanolamine, propanolamine, and hydroxybenzylamine, as well as H 2 N
(C 2 H 4 O) 2 H and other aminated polyethylene glycols are also used. The reaction time between the amino alcohol and the copolymer is appropriately selected depending on the type and concentration of the amino alcohol, the temperature, and the composition of the copolymer. A part of
Preferably, it is converted to a glutamine derivative. (e) Examples of the invention Next, the present invention will be explained in more detail using examples. Example 1 A benzene solution of a copolymer of L-leucine and benzyl L-glutamate (molar ratio of leucine and benzyl glutamate = 7:3) was cast onto a glass plate and air-dried to form a film (thickness: 0.15 mm) was obtained. This film was subjected to Soxhlet extraction with ethanol and then dried. This film was immersed in 3-amino-1-propanol, reacted at 60°C for 80 hours, thoroughly washed with ethanol and dried to obtain a film. 3-
Comparing the changes in the total reflection infrared absorption spectrum of the film before and after reaction with amino-1-propanol, 1730,
The peak intensities at 750 and 700 cm -1 decreased after the reaction. A culture solution containing human-derived epithelial cells (approximately 100,000 cells/ml) was left in contact with this film in a room at 37°C with a carbon dioxide concentration of 5% and humidity of 100%.
After 17 hours, the film was lightly washed with phosphate buffer, and
The amount of cells adhering to the membrane was quantified by nuclear staining. For comparison, a similar cell adhesion test was conducted using the leucine-benzyl glutamate copolymer film, the silicone rubber used for the skin-penetrating tube, 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. The results are shown in Table 1.
【表】
実施例 ２
ロイシンとグルタミン酸ベンジルとのモル比＝
７：３のかわりにロイシンとグルタミン酸ベンジ
ルとのモル比＝85：15を用いた以外は実施例１と
同様にして皮膜を調製した。この膜をエタノール
アミン中に浸漬し、60℃で92時間反応させ、エタ
ノールで十分に洗浄後乾燥して膜を得た。
実施例 ３
実施例１におけるロイシン−グルタミン酸ベン
ジル共重合体皮膜をH2N（C2H4O）2H中に浸漬し、
70℃で88時間反応させ、エタノールで十分に洗浄
後乾燥して膜を得た。
実施例 ４
ガラス管の外表面にロイシン−グルタミン酸ベ
ンジル共重合体を塗布し、乾燥後ガラス管からは
ずし、アミノアルコールで処理をして管状物を得
た。
(f) 発明の効果
本発明は以上説明したように、細胞付着性の多
いことを必要とする皮膚貫通管において、アミノ
アルコールで変性されたロイシン−グルタミン酸
ベンジル共重合体を外表面に成型することにより
細胞の付着を増し、かつ、この皮膚貫通管を任意
の形状で得ることが可能である。[Table] Example 2 Molar ratio of leucine and benzyl glutamate =
A film was prepared in the same manner as in Example 1 except that the molar ratio of leucine to benzyl glutamate = 85:15 was used instead of 7:3. This membrane was immersed in ethanolamine, reacted at 60°C for 92 hours, thoroughly washed with ethanol, and dried to obtain a membrane. Example 3 The leucine-benzyl glutamate copolymer film in Example 1 was immersed in H2N ( C2H4O ) 2H ,
The reaction was carried out at 70°C for 88 hours, thoroughly washed with ethanol, and then dried to obtain a membrane. Example 4 A leucine-benzyl glutamate copolymer was applied to the outer surface of a glass tube, and after drying, it was removed from the glass tube and treated with amino alcohol to obtain a tube. (f) Effects of the Invention As explained above, the present invention is directed to forming a leucine-benzyl glutamate copolymer modified with amino alcohol on the outer surface of a skin-penetrating tube that requires high cell adhesion. This increases the adhesion of cells, and it is possible to obtain this skin-penetrating tube in any shape.
Claims (1)
ルタミン酸ベンジル共重合体を外表面に有する皮
膚貫通管。1. A skin-penetrating tube having an amino alcohol-modified leucine-benzyl glutamate copolymer on its outer surface.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59205217A JPS6182758A (en) | 1984-09-28 | 1984-09-28 | Skin piercing tube |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59205217A JPS6182758A (en) | 1984-09-28 | 1984-09-28 | Skin piercing tube |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6182758A JPS6182758A (en) | 1986-04-26 |
| JPS6352905B2 true JPS6352905B2 (en) | 1988-10-20 |
Family
ID=16503343
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59205217A Granted JPS6182758A (en) | 1984-09-28 | 1984-09-28 | Skin piercing tube |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6182758A (en) |
-
1984
- 1984-09-28 JP JP59205217A patent/JPS6182758A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6182758A (en) | 1986-04-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |