JPWO2013038901A1 - 有機ケイ素化合物及びそれを含むシランカップリング剤 - Google Patents
有機ケイ素化合物及びそれを含むシランカップリング剤 Download PDFInfo
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- JPWO2013038901A1 JPWO2013038901A1 JP2013533597A JP2013533597A JPWO2013038901A1 JP WO2013038901 A1 JPWO2013038901 A1 JP WO2013038901A1 JP 2013533597 A JP2013533597 A JP 2013533597A JP 2013533597 A JP2013533597 A JP 2013533597A JP WO2013038901 A1 JPWO2013038901 A1 JP WO2013038901A1
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- silane coupling
- cells
- coupling agent
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- organosilicon compound
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Abstract
Description
すなわち、本発明の態様の一つは、下記式(1):
で表される有機ケイ素化合物である。
また、本発明の他の態様は、前記シランカップリング剤を基材に塗布又は該シランカップリング剤中に基材を浸漬させる工程を含む、シランカップリング剤固定化方法である。
前記式(1)で表される有機ケイ素化合物の原料であるベタインとしては、例えば、N−メタクリロイルオキシエチル−N,N−ジメチルアンモニウム−α−N−メチルカルボキシベタイン、N−メタクリロイルオキシエチル−N,N−ジメチルアンモニウム−α−N−プロピルスルホキシベタイン、N−メタクリロイルアミノプロピル−N,N−ジメチルアンモニウム−α−N−プロピルスルホキシベタインが好ましい。
PGME(プロピレングリコールモノメチルエーテル)/水=9/1体積%濃度の溶媒に酢酸を加えて、pH4.0に調製した。その後、合成例1及び合成例2で得られた有機ケイ素化合物それぞれを、1質量%濃度となるように前記溶媒に溶解させ、シランカップリング剤を調製した。
合成例1で得られた化合物2を含むシランカップリング剤10ml中にガラス基板(TEMPAX Float〔登録商標〕、50×50mm、厚さ1mm)を浸漬させ、40℃で24時間静置した。そのガラス基板を前記シランカップリング剤から取り出した後、PGMEで洗浄し、風乾した。
合成例2で得られた化合物4を含むシランカップリング剤10ml中に、実施例1で使用したガラス基板と同種のガラス基板を浸漬させ、40℃で24時間静置した。そのガラス基板を前記シランカップリング剤から取り出した後、PGMEで洗浄し、風乾した。
合成例1で得られた化合物2を含むシランカップリング剤0.5mlを、実施例1で使用したガラス基板と同種のガラス基板上にスピンコーターを用いて塗布し、ホットプレート上にて100℃で15分間ベークした。その後、PGMEで洗浄し、風乾した。
合成例2で得られた化合物4を含むシランカップリング剤0.5mlを、実施例1で使用したガラス基板と同種のガラス基板上にスピンコーターを用いて塗布し、ホットプレート上にて100℃で15分間ベークした。その後、PGMEで洗浄し、風乾した。
実施例1で使用したガラス基板と同種のガラス基板をPGMEにて洗浄し、風乾した。
実施例1乃至実施例4及び比較例1で処理した各ガラス基板の表面に対する接触角測定を、水及びジヨードメタンを用いて行った。接触角計(協和界面科学(株)製)を用いて液滴法にて測定し、θ/2法にて接触角を算出した。その結果を下記表1に示す。
蛍光標識されたウシ血清アルブミン(FITC−BSA、シグマアルドリッチ社製)をリン酸生理食塩水(PBS、pH7.4)に溶解させ、100μg/mlのFITC−BSA溶液を調製した。このFITC−BSA溶液0.5mlを、実施例1乃至実施例4及び比較例1で処理した各ガラス基板の表面に添加し、37℃で30分間静置した。その後、前記各ガラス基板の表面からFITC−BSA溶液を除き、溶媒として用いたPBSにて洗浄し、風乾した。
合成例1及び合成例2で得られた有機ケイ素化合物それぞれを、10mM溶液となるように99.5体積%エタノール(0.5体積%の水含有)に溶解させ、シランカップリング剤を調製した。
合成例1で得られた化合物2を含む10mMエタノール溶液100ml中に、O2エッチングにて表面洗浄したガラス基板(TEMPAX Float〔登録商標〕、Φ12mm、厚さ1mm)を浸漬させ、室温で48時間静置した。そのガラス基板を前記の溶液から取り出した後、エタノールで洗浄し、風乾した。
合成例2で得られた化合物4を含む10mMエタノール溶液100ml中に、実施例5で使用したガラス基板と同種のガラス基板を浸漬させ、室温で48時間静置した。そのガラス基板を前記の溶液から取り出した後、エタノールで洗浄し、風乾した。
実施例5で使用したガラス基板と同種のガラス基板をプラスチックケース内に1週間保管した。
3.8質量%クエン酸ナトリウム溶液0.5mlに対して、健康なボランティアより採血した血液4.5mLを混和した後、遠心分離にて[冷却遠心機5900((株)久保田製作所製)、1000rpm/10分、室温]上層の多血小板血漿(PRP)を回収した。引き続き、下層について遠心分離を行い(上記遠心機、3500rpm/10分、室温)、上層の乏血小板血漿(PPP)を回収した。多項目自動赤血球分析装置(XT−2000i、シスメックス(株)製)にてPRPの血小板数を計測後、PPPを用いてPRPの血小板濃度が30×104cells/μLになるように調製した。
24穴平底マイクロプレート(コーニング社製)に実施例5、実施例6及び比較例2で処理した各ガラス基板を配置し、上記血小板濃度に調製したPRP溶液300μLを添加した。5%二酸化炭素濃度を保った状態で、37℃で90分間CO2インキュベーター内にて静置した。プレート内のPRPを除いた後、リン酸緩衝生理食塩水(PBS)3mLにて5回洗浄した。その後、2.5体積%グルタルアルデヒドのPBS溶液2mLを添加し、4℃で一昼夜静置後、グルタルアルデヒドのPBS溶液を除き、超純水(Milli−Q水)3mLで5回洗浄した。さらに、70%エタノール水(v/v)1mLで3回洗浄し、風乾した。この実験を2回行った(Run−1、Run−2)。
上記血小板付着実験を行った実施例5、実施例6及び比較例2で処理した各ガラス基板に、イオンスパッター(E−1030、(株)日立ハイテクノロジーズ製)にてPt−Pdを1分間蒸着した。その後、電子顕微鏡(S−4800、(株)日立ハイテクノロジーズ製)にて血小板の付着を1,000倍で観察した。
細胞は、ヒト胎児腎細胞株Hek293(DSファーマバイオメディカル社製)、ヒト肝癌細胞株HepG2(DSファーマバイオメディカル社製)、ヒト子宮頸癌細胞株HeLa(DSファーマバイオメディカル社製)、ヒト胎児肺細胞株MRC5(DSファーマバイオメディカル社製)、及びチャイニーズハムスター卵巣細胞株CHO(DSファーマバイオメディカル社製)を用いた。それらの細胞の培養に用いた培地は、HeLa、Hek293及びMRC5:10%(v/v)FBSを含むEMEM培地(和光純薬工業(株)製)、HepG2:10%(v/v)FBSを含むDMEM培地(和光純薬工業(株)製)、CHO:10%(v/v)FBSを含むDMEM/F−12培地(シグマアルドリッチ社製)を用いた。細胞は、37℃CO2インキュベーター内にて5%二酸化炭素濃度を保った状態で、直径10cmのシャーレ(培地10mL)を用いて2日間以上静置培養した。引き続き、本細胞をPBS5mlで洗浄した後、トリプシン−EDTA溶液 (インビトロジェン社製)1mLを添加して細胞を剥がし、上記の培地10mLにて懸濁した。本懸濁液を遠心分離(上記血小板溶液の調製で用いた遠心機、1500rpm/3分、室温)後、上清を除き、上記の培地を添加して細胞懸濁液を調製した。
24穴平底マイクロプレート(コーニング社製)に実施例5、実施例6及び比較例2で処理した各ガラス基板を配置し、調製した上記細胞懸濁液を2.5×105cells/wellとなるように各1mL加えた。その後、5%二酸化炭素濃度を保った状態で、37℃で24時間CO2インキュベーター内にて静置した。
24時間後、上記細胞付着実験を行った実施例5、実施例6及び比較例2で処理した各ガラス基板を別の24穴平底マイクロプレートに移し、PBS1mLで洗浄した。PBSを除いた後、トリプシン−EDTA溶液 (インビトロジェン社製)500μLを添加した。5分〜10分後、10%(v/v)FBSを含むDMEM培地(和光純薬工業(株)製)を500μL添加し、剥がれた細胞を1.5mLマイクロテストチューブ(エッペンドルフ社製)に移した。遠心分離((株)トミー精工製、型番:MX−307、1500rpm/3分、室温)後、上清を除き、10%(v/v)FBSを含むDMEM培地(和光純薬工業(株)製)100μLを添加して細胞懸濁液を調製した。本懸濁液にトリパンブルー染色液を等量添加後、血球計測板(エルマ販売株式会社製)にて生細胞数(細胞付着数)を計測した。
Claims (8)
- 請求項1に記載の有機ケイ素化合物、極性有機溶媒及び水を含むシランカップリング剤。
- さらに有機酸を含む請求項2に記載のシランカップリング剤。
- 請求項2又は請求項3に記載のシランカップリング剤からなる生体物質又は細胞の付着抑制剤。
- 前記細胞が生体を構成する体細胞、生体から分離された癌細胞、又は生体から分離され不死化能を獲得して体外で安定して維持される細胞である、請求項4に記載の付着抑制剤。
- 前記細胞が血小板である請求項4に記載の付着抑制剤。
- 請求項2又は請求項3に記載のシランカップリング剤を基材上に塗布しベークする工程、その後極性溶媒で前記基材を洗浄する工程、及び前記基材を乾燥させる工程を含むシランカップリング剤固定化方法。
- 基材を請求項2又は請求項3に記載のシランカップリング剤中に浸漬する工程、その後極性溶媒で前記基材を洗浄する工程、及び前記基材を乾燥させる工程を含むシランカップリング剤固定化方法。
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JP6150071B2 (ja) | 2017-06-21 |
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US20140370182A1 (en) | 2014-12-18 |
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