JPH11508355A - 光学的方法による膜内外電位差の検出 - Google Patents
光学的方法による膜内外電位差の検出Info
- Publication number
- JPH11508355A JPH11508355A JP9501926A JP50192697A JPH11508355A JP H11508355 A JPH11508355 A JP H11508355A JP 9501926 A JP9501926 A JP 9501926A JP 50192697 A JP50192697 A JP 50192697A JP H11508355 A JPH11508355 A JP H11508355A
- Authority
- JP
- Japan
- Prior art keywords
- membrane
- group
- reagent
- fluorescent
- independently
- 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.)
- Granted
Links
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- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
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- IRYJRGCIQBGHIV-UHFFFAOYSA-N trimethadione Chemical compound CN1C(=O)OC(C)(C)C1=O IRYJRGCIQBGHIV-UHFFFAOYSA-N 0.000 description 1
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- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
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- 150000003732 xanthenes Chemical class 0.000 description 1
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Classifications
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.膜にかかる電気電位を測定する方法であって、 (a)膜電位の変化に応答して膜の第一表面から第二表面へ再分配しうる疎水 性蛍光イオンを含む第一試薬を導入し、 (b)(i)励起状態のエネルギーを蛍光イオンへ供与するか、または(ii)励起状 態のエネルギーを蛍光イオンより受容することによりエネルギー伝達を経験しう る発色団を含み、膜の第一表面または第二表面を標識する第二試薬を導入し、 (c)膜に励起光を当て、 (d)蛍光イオンと第二試薬との間のエネルギー伝達を測定し、 (e)エネルギー伝達を膜電位と関連づける ことを含む前記方法。 2.蛍光イオンと第二試薬の間のエネルギー伝達が蛍光共鳴エネルギー伝達(FRE T)によるものである請求項1記載の方法。 3.膜が生物細胞の形質膜である請求項1記載の方法。 4.細胞が哺乳類細胞である請求項3記載の方法。 5.膜が細胞内小器官のものである請求項4記載の方法。 6.細胞を、L−M(TK-)細胞、神経芽細胞腫細胞、神経膠星状芽細胞腫細 胞及び新生児心筋細胞よりなる群から選択する請求項4記載の方法。 7.膜がリン脂質二重層を含む請求項1記載の方法。 8.イオンがアニオンである請求項1記載の方法。 9.アニオンが1個の電荷を有する請求項8記載の方法。 10.アニオンを、ポリメチンオキソノール、テトラアリールボレート及び遷移金 属の錯体よりなる群から選択する請求項8記載の方法。 11.アニオンが式 (式中、Rは独立にH、ヒドロカルビル及びヘテロアルキルよりなる群から 選ばれ、Xは酸素または硫黄であり、nは1〜3の整数である) のオキソノール及びその塩である請求項10記載の方法。 12.Xが硫黄である請求項11記載の方法。 13.各Rが同一であり、C1-10アルキル基から選ばれるヒドロカルビル基であり 、n=2である請求項11記載の方法。 14.アニオンが式 [(Ar1)3B−Ar2−Y−FLU]- (式中、Ar1はアリール基であり、Ar2はアリーレン基であり、Bはホウ 素であり、Yは酸素または硫黄であり、FLUは中性発蛍光団である) のテトラアリールボレート及びその誘導体である請求項10記載の方法。 15.Ar1がトリフルオロメチルフェニルであり、Ar2がテトラフルオロフェニ ルであり、Yが酸素である請求項14記載の方法。 16.中性発蛍光を、ビマン、ジフルオロボラジアザインダセン及びクマリンより なる群から選択する請求項14記載の方法。 17.中性蛍光団が式 (式中、各R5は同一または異なっていてもよく、独立にH、低級アルキル またはアルキレン連結点である) のビマンである請求項16記載の方法。 18.中性発蛍光団が式 (式中、各R1は同一または異なっていてもよく、H、低級アルキル、アリ ール、ヘテロ芳香族、アラルケニル及びアルキレン連結点よりなる群から独立に 選ばれ、各R2は同一または異なっていてもよく、H、低級アルキル、フェニル 及びアルキレン連結点よりなる群から独立に選ばれる) のジフルオロボラジアザインダセンである請求項16記載の方法。 19.中性発蛍光団が式 (式中、各R3は同一または異なっていてもよく、H、ハロゲン、低級アル キル、CN、CF3及びOR5よりなる群から独立に選ばれ、R4は同一または異 なっていてもよく、H、OR5及びアルキレン連結点よりなる群から選ばれ、Z はO、SまたはNR”であり、R5はH、低級アルキル及びアルキレン連結点よ りなる群から選ばれる) のクマリンである請求項16記載の方法。 20.中性発蛍光団が式 (式中、Ln=Tb、Eu、またはSmであり、Rは独立にH、C1〜C8 アルキル、C1〜C8シクロアルキルまたはC1〜C4パーフルオロアルキルで あり、X及びYは独立にH、F、Cl、Br、I、NO2、CF3、低級(C1〜 C4)アルキル、CN、Ph、O−(低級アルキル)、またはOPhであるか、あ るいはX及びYは一緒になって−CH=CH−であり、Z=アルキレンジイル、 ヘテロアルキレンジイルまたはヘテロシクロジイルである) の遷移金属の錯体である請求項16記載の方法。 21.Z=1,2−エタンジイル、1,3−プロパンジイル、2,3−ブタンジイ ル、1,2−シクロヘキサンジイル、1,2−シクロペンタンジイル、1,2− シクロヘプタンジイル、1,2−フェニレンジイル、3−オキサ−1,5−ペン タンジイル、3−アザ−3−(低級アルキル)−1,5−ペンタンジイル、ピリジ ン−2,6−ビス(メチレン)またはテトラヒドロフラン−2,5−ビス(メチレ ン)である請求項20記載の方法。 22.中性発蛍光団が式 (式中、Ln=Tb、Eu、またはSmであり、Rは独立にH、C1〜C8 アルキル、C1〜C8シクロアルキルまたはC1〜C4パーフルオロアルキ ルであり、X'及びY'は独立にH、F、Cl、Br、I、NO2、CF3、低級( C1〜C4)アルキル、CN、Ph、O−(低級アルキル)、またはOPhである か、あるいはX'及びY'は一緒になって−CH=CH−であり、Z’は独立に原 子価結合、CR2、ピリジン−2−6−ジイルまたはテトラヒドロフラン−2, 5−ジイルである) の遷移金属の錯体である請求項16記載の方法。 23.第二試薬が発蛍光団である請求項1記載の方法。 24.第二試薬を、レクチン、脂質、炭水化物、チトクロム及び抗体(各々、発蛍 光団で標識されている)よりなる群から選択する請求項23記載の方法。 25.発蛍光団を、キサンテン、シアニン及びクマリンよりなる群から選択する請 求項24記載の方法。 26.第二試薬が脂質であり、リン脂質である請求項24記載の方法。 27.第一試薬と第二試薬がリンカーにより共有結合している請求項1記載の方法 。 28.リンカーが式 X−(CH2)m−Zq−(CH2)m'−Z'q'−(CH2)m"−Z"q"−Y (式中、Xはポリメチンオキソノール及び蛍光テトラアリールボレートより なる群から選ばれる疎水性蛍光アニオンであり、Yはレクチン及びリン脂質より なる群から選ばれる蛍光第二試薬であり、Z、Z'、Z"は独立にO、S、SS、 CO、COOであり、m、m'及びm"は0〜約32の整数であり、q、q'及び q"は独立に0または1であり、m+q+m'+q'+m"+q"は約20〜40で ある) の化合物である請求項27記載の方法。 29.リンカーがチオエーテルである請求項28記載の方法。 30.(a)膜電位の変化に応答して膜の第一表面から第二表面へ再分配しうる疎水 性蛍光イオンを含む第一試薬、及び (b)(i)励起状態のエネルギーを蛍光イオンへ供与するか、または(ii)励起状 態のエネルギーを蛍光イオンより受容することによりエネルギー伝達を経験しう る発色団を含み、膜の第一表面または第二表面を標識する第二試薬を含むキット 。 31.第一試薬をポリメチンオキソノール、テトラアリールボレート及び遷移金属 の錯体よりなる群から選択し、第二試薬をレクチン、脂質、炭水化物、チトクロ ム及び抗体(各々、発蛍光団で標識されている)よりなる群から選択する請求項 30記載のキット。 32.可溶化剤をさらに含む請求項30記載のキット。 33.式A−L−Bの化合物(式中、Aは独立にポリメチンオキソノールまたは発 蛍光団に結合したテトラアリールボレートであり、Lはリンカーであり、Bは膜 不透過性発蛍光団または発蛍光団の膜不透過性複合体である)。 34.Aが式 (式中、Rは独立にH、ヒドロカルビル及びヘテロアルキルよりなる群から 選ばれ、Xは酸素または硫黄であり、nは1〜3の整数である。但し、Rの少な くとも一つはアルキレン基である) のポリメチンオキソノールである請求項33記載の化合物。 35.式Cou-PEの化合物(式中、Couは式 (式中、各R3は同一または異なっていてもよく、H、ハロゲン、低級アル キル,CN、CF3、COOR5、CON(R5)2、OR5、及び連結点よりなる群 から独立に選ばれ、R4はOR5及びN(R5)2よりなる群から選ばれ、ZはO、S またはNR5であり、各R5は同一または異なっていてもよく、H、低級アルキル 及びアルキレン連結点よりなる群から独立に選ばれる)のクマリンであり、PEは N−結合ホスファチジルエタノールアミンである)。 36.式 (式中、Ln=Tb、Eu、またはSmであり、Rは独立にH、C1〜C8 アルキル、C1〜C8シクロアルキルまたはC1〜C4パーフルオロアルキルで あり、X及びYは独立にH、F、Cl、Br、I、NO2、CF3、低級(C1〜 C4)アルキル、CN、Ph、O−(低級アルキル)、またはOPhであるか、あ るいはX及びYは一緒になって−CH=CH−であり、Z=アルキレンジイル、 ヘテロアルキレンジイルまたはヘテロシクロジイルである)の化合物。 37.Z=1,2−エタンジイル、1,3−プロパンジイル、2,3−ブタンジイ ル、1,2−シクロヘキサンジイル、1,2−シクロペンタンジイル、1,2− シクロヘプタンジイル、1,2−フェニレンジイル、3−オキサ−1,5−ペン タンジイル、3−アザ−3−(低級アルキル)−1,5−ペンタンジイル、ピリジ ン−2,6−ビス(メチレン)またはテトラヒドロフラン−2,5−ビス(メチレ ン)である請求項36記載の化合物。 38.式 (式中、Ln=Tb、Eu、またはSmであり、Rは独立にH、C1〜C8 アルキル、C1〜C8シクロアルキルまたはC1〜C4パーフルオロアルキルで あり、X'及びY'は独立にH、F、Cl、Br、I、NO2、CF3、低級(C1 〜C4)アルキル、CN、Ph、O−(低級アルキル)、またはOPhであるか、 あるいはX'及びY'は一緒になって−CH=CH−であり、Z’は独立に原子価 結合、CR2、ピリジン−2−6−ジイルまたはテトラヒドロフラン−2,5− ジイルである)の化合物。 39.式 (式中、Xは酸素または硫黄であり、RはC4-12ヒドロカルビルであり、n は1〜3の整数である。但し、nが1の場合、RはC7-12ヒドロカルビルである ) のポリメチンオキソノール及びその塩。 40.式 (式中、PEはN−結合ホスファチジルエタノールアミンである)の化合物。 41.細胞の膜電位に作用する試験サンプルを同定する方法であって、 (a)第一試薬及び第二試薬(これらは共に、請求項1に記載の方法により膜 電位を測定するものである)を細胞にロードし、 (b)膜を試験サンプルに暴露し、 (c)膜の電位を測定し、 (d)(c)の電位を試験サンプルの不存在下での電位と比較し、試験サンプルの 膜電位に及ぼす効果を求める ことを含む前記方法。 42.(e)イオンチャネル、ポンプまたは交換体の活性を調節する刺激物質に膜を 暴露し、 (f)膜電位を測定し、 (g)試験サンプルの存在下での膜電位を再度測定し、 (h)(f)の膜電位をと(g)の膜電位を比較し、刺激物質に対する試験サンプル の効果を求める ことをさらに含む請求項41記載の方法。 43.細胞が哺乳類細胞である請求項41または42記載の方法。 44.膜中のイオンチャネル、ポンプまたは交換体の活性を調節する化合物を同定 するために試験サンプルをスクリーニングする方法であって、 (a)第一試薬及び第二試薬(これらは共に、請求項1記載の方法により膜電 位を測定するものである)を細胞の第一群及び第二群にロードし、 (b)任意に、細胞の第一群と第二群の両方をイオンチャネル、ポンプまた は交換体を調節する刺激物質に暴露し、 (c)細胞の第一群を試験サンプルに暴露し、 (d)細胞の第一群及び第二群の膜電位を測定し、 (e)細胞の第一群と第二群の間の膜電位の差を、試験サンプル中に含まれる 化合物の膜中のイオンチャネル、ポンプまたは交換体の活性を調節する能力に関 連づける ことを含む前記方法。 45.式 [(Ar1)3B−Ar2−Y−FLU]- (式中、Ar1はアリール基であり、Ar2はアリーレン基であり、Bはホウ 素であり、Yは酸素または硫黄であり、FLUは中性発蛍光団である) の蛍光テトラアリールボレートを合成する方法であって、 (a)トリアリールボラン(Ar1)3Bを式(P−Y−Ar2)−M(式中、Pは 保護基であり、Mは金属である)の有機金属試薬で処理して保護テトラアリール ボレート(Ar1)3B−Ar2−Y−Pを形成し、 (b)保護テトラアリールボレートから保護基を除去して(Ar1)3B−Ar2− YHを形成し、 (c)(Ar1)3B−Ar2−YHを、脱離基を有する発蛍光団FLUで処理して 蛍光テトラアリールボレートを形成する ことを含む前記方法。 46.式 (式中、各R'は独立にH、ヒドロカルビル、ハロゲン、CF3たはリンカー 基であり、nは0〜5の整数であり、各Xは独立にH、ハロゲンまたはCF3で あり、mは0〜4の整数であり、Yは酸素または硫黄であり、FLUはキサンテ ン、クマリン、シアニン、ビマン及びジフルオロボラジアザインダセンよりなる 群から選ばれる中性発蛍光団である)の化合物。
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JP2003518246A (ja) * | 1999-12-13 | 2003-06-03 | ザ リージェンツ オブ ザ ユニバーシティー オブ カリフォルニア | 光学的方法による膜貫通電位の検出 |
JP2004514115A (ja) * | 2000-07-10 | 2004-05-13 | ヴァーテックス ファーマシューティカルズ (サンディエゴ)エルエルシー | イオンチャネルアッセイ法 |
JP2012110327A (ja) * | 2000-07-10 | 2012-06-14 | Vertex Pharmaceuticals (San Diego) Llc | イオンチャネルアッセイ法 |
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JP2002532487A (ja) * | 1998-12-14 | 2002-10-02 | オーロラ バイオサイエンシーズ コーポレイション | シトクロムp450活性に対する光学分子センサ |
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JP2004514115A (ja) * | 2000-07-10 | 2004-05-13 | ヴァーテックス ファーマシューティカルズ (サンディエゴ)エルエルシー | イオンチャネルアッセイ法 |
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CA2223927A1 (en) | 1996-12-19 |
WO1996041166A3 (en) | 1997-05-15 |
JP4033899B2 (ja) | 2008-01-16 |
EP0834074A1 (en) | 1998-04-08 |
DE69605041T2 (de) | 2000-03-16 |
CA2223927C (en) | 2004-04-06 |
AU6264396A (en) | 1996-12-30 |
US6107066A (en) | 2000-08-22 |
DE69635193D1 (de) | 2005-10-20 |
ATE304706T1 (de) | 2005-09-15 |
JP2004231666A (ja) | 2004-08-19 |
HK1090422A1 (en) | 2006-12-22 |
ES2140870T3 (es) | 2000-03-01 |
DK0834074T4 (da) | 2005-12-12 |
EP0977035A3 (en) | 2000-03-01 |
DK0834074T3 (da) | 2000-04-03 |
EP0834074B2 (en) | 2005-11-16 |
EP1610126A1 (en) | 2005-12-28 |
DE69605041D1 (de) | 1999-12-09 |
EP0834074B1 (en) | 1999-11-03 |
WO1996041166A2 (en) | 1996-12-19 |
AU716130B2 (en) | 2000-02-17 |
US5661035A (en) | 1997-08-26 |
ATE186400T1 (de) | 1999-11-15 |
DE69605041T3 (de) | 2006-09-21 |
EP0977035B2 (en) | 2010-07-21 |
EP1610126B1 (en) | 2014-04-30 |
DE69635193T2 (de) | 2006-01-19 |
ES2140870T5 (es) | 2006-04-16 |
JP4064945B2 (ja) | 2008-03-19 |
EP0977035B1 (en) | 2005-09-14 |
DE69635193T3 (de) | 2011-03-10 |
EP0977035A2 (en) | 2000-02-02 |
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