JPH11502714A - β−ラクタマーゼ用の基質およびその使用 - Google Patents
β−ラクタマーゼ用の基質およびその使用Info
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- JPH11502714A JPH11502714A JP8529573A JP52957396A JPH11502714A JP H11502714 A JPH11502714 A JP H11502714A JP 8529573 A JP8529573 A JP 8529573A JP 52957396 A JP52957396 A JP 52957396A JP H11502714 A JPH11502714 A JP H11502714A
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Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.式(I): 〔式中、 XおよびYの一方は蛍光供与体部分またはその膜透過性誘導体であり、他方 は消光体部分、受容体蛍光団部分またはその膜透過性誘導体であり; R'はH、低級アルキル、(CH2)nOH、(CH2)nCOOR”および =NOJ よりなる群か ら選ばれ、ここで nは0または1〜5の整数であり、J はH、Me、CH2COOH、CHM eCOOHまたはCMe2COOHであり; R"はH、生理学的に許容される金属およびアンモニウムカチオン、-CHR2OCO (CH2)nCH3、-CHR2OCOC(CH3)3、アシルチオメチル、アシルオキシ-α-ベンジル、 δ−ブチロラクトニル、メトキシカルボニルオキシメチル、フェニル、メチルス ルフィニルメチル、β−モルホリノエチル、ジアルキルアミノエチル、ジアルキ ルアミノカルボニルオキシメチルよりなる群から選ばれ、ここでR2はHおよび低 級アルキルよりなる群から選ばれ; AはS、O、SO、SO2およびCH2よりなる群から選ばれ; Z'はXのためのリンカーであり;そして Z"はYのためのリンカーである〕 で表される化合物。 2.Z'が直接結合、 〔ここで、R2およびn は先に定義したとおりであり、R3は水素および低級アル キルよりなる群から選ばれ、そして mおよびp はそれぞれが0〜4の整数よりな る群から独立に選ばれる〕よりなる群から選ばれる、請求項1に記載の化合物。 3.Z"が発色団中のO、NおよびSよりなる群から選ばれるヘテロ原子への直接 結合、 〔ここで、R2およびn は先に定義したとおりであり、m は0〜4の整数である 〕よりなる群から選ばれる、請求項1に記載の化合物。 4.R'がHおよびメチルよりなる群から選ばれる、請求項1に記載の化合物。 5.R'がHである、請求項4に記載の化合物。 6.R"がHおよびアセトキシメチルよりなる群から選ばれる、請求項1に記載の 化合物。 7.R2がHである、請求項1に記載の化合物。 8.Aが−S−である、請求項1に記載の化合物。 9.XおよびYの1つが蛍光供与体部分の膜透過性誘導体、または消光体部分も しくは受容体蛍光団部分の膜透過性誘導体であり、XおよびYの少なくとも1つ が少なくとも1つのアシル化芳香族ヒドロキシル、アシル化アミン、またはアル キル化芳香族ヒドロキシルを含み、ここで該アシル基は1〜5個の炭素原 子を含み、該アルキル基は-CH2OC(O)alk、-CH2SC(O)alk、-CH2OC(O)Oalk 、低級 アシルオキシ−α−ベンジル、およびδブチロラクトニルよりなる群から選ばれ 、alk は1〜4個の炭素原子の低級アルキルである、請求項1に記載の化合物。 10.XおよびYの少なくとも1つが少なくとも1つのアシル化芳香族ヒドロキシ ルを含み、該アシル基がアセチル、n-プロピオニルまたはn-ブチリルである、請 求項9に記載の化合物。 11.前記の供与体が式II-VIIのクマリンであり、前記の消光体または受容体が式 VIII-XII、XLVII およびXLVII のフルオレセイン、ロドールおよびローダミンよ りなる群から選ばれる、請求項1に記載の化合物。 12.前記の供与体が式II-VIIのクマリンおよび式VIIIのフルオレセインよりなる 群から選ばれる、請求項11に記載の化合物。 13.前記の消光体または受容体が式VIII-XIIのフルオレセイン、ロドールおよび ローダミンよりなる群から選ばれる、請求項1に記載の化合物。 14.前記の供与体が式VIIIのフルオレセインであり、前記の消光体または受容体 が式VIII-XIIのロドールおよびローダミンよりなる群から選ばれる、請求項13に 記載の化合物。 15.前記のクマリンが7-ヒドロキシクマリンおよび7-ヒドロキシ-6-クロロクマ リンよりなる群から選ばれ、前記のフルオレセインがフルオレセインおよびジク ロロフルオレセインよりなる群から選ばれる、請求項12に記載の化合物。 16.前記の供与体がフルオレセインであり、前記の消光体または受容体がエオシ ンまたは式VIII(式中 Ra、Rb、RcおよびRdはBrまたはClである)のテトラクロ ロフルオレセインよりなる群から選ばれる、請求項13に記載の化合物。 17.前記の消光体または受容体が式VIII、IXまたはXIのロドールである、請求項 13に記載の化合物。 18.前記の消光体または受容体が式VIII、X またはXII のローダミンである、請 求項13に記載の化合物。 19.XおよびYの少なくとも1つが芳香族ヒドロキシル基上にアセトキシメチル 基を含む膜透過性誘導体である、請求項9に記載の化合物。 20.Z'が-(CH2)nCONR2(CH2)m- である、請求項2に記載の化合物。 21.n およびm が0である、請求項20に記載の化合物。 22.R2がHである、請求項20に記載の化合物。 23.Z"が-S(CH2)n- である、請求項3に記載の化合物。 24.nが0である、請求項23に記載の化合物。 25.式: 〔式中、 RYはH、ClおよびBrよりなる群から選ばれ、 RXはHおよびメチルよりなる群から選ばれ、 RZおよびRZ1は-C(O)alk、-CH2OC(O)alk、-CH2SC(O)alk、-CH2OC(O)Oalk、低 級アシルオキシ-α-ベンジル、およびδブチロラクトニルよりなる群から独立に 選ばれ、ここでalk は1〜4個の炭素原子の低級アルキルであり、 R"は1-(アシルオキシ)アルキルである〕 で表される、請求項12に記載の化合物。 26.RZおよびRZ1がアセチル、ブチリルおよびアセトキシメチルよりなる群から 選ばれる、請求項25に記載の化合物。 27.式: 〔式中、 RYはH、ClおよびBrよりなる群から選ばれ、そして RXはHおよびメチルよりなる群から選ばれる〕 で表される、請求項12に記載の化合物。 28.式(11): で表される請求項14に記載の化合物またはその膜透過性蛍光原誘導体。 29.式(16): 〔式中、RZおよびRZ1は-C(O)alk、-CH2OC(O)alk、-CH2SC(O)alk、-CH2OC(O)Oa lk、低級アシルオキシ-α-ベンジル、およびδブチロラクトニルよりなる群から 独立に選ばれ、ここでalk は1〜4個の炭素原子の低級アルキルである〕 で表される、請求項16に記載の化合物。 30.式(22): で表される請求項14に記載の化合物またはその膜透過性蛍光原誘導体。 31.式(25): で表される請求項1に記載の化合物またはその膜透過性蛍光原誘導体。 32.RYがClで、RXがHである(CCF2 または76)、請求項27に記載の化合物。 33.式: で表される、請求項15に記載の化合物。 34.RZおよびR"がアセトキシメチルであり、RXがHであり、そして各RZ1がアセ チルである、請求項26に記載の化合物。 35.RYがHであり、そしてRXがメチルである(CCF1 7a)、請求項27に記載の化合 物。 36.前記の供与体が蛍光ユウロピウムおよびテルビウム錯体よりなる群から選ば れる、請求項1に記載の化合物。 37.前記の供与体がユウロピウムおよびテルビウムトリス-(ビピリジン)クリプ タンドおよび関連染料よりなる群から選ばれる、請求項36に記載の化合物。 38.前記の消光体または受容体がフタロシアニンおよび関連染料よりなる群から 選ばれる、請求項1に記載の化合物。 39.前記の消光体または受容体がフタロシアニンおよび関連染料よりなる群から 選ばれる、請求項37に記載の化合物。 40.式: で表される、請求項39に記載の化合物。 41.前記のクマリンが式(III): 〔式中、 EはH、OH、ORkおよびNRgRhよりなる群から選ばれ、 TはOおよびNRkよりなる群から選ばれ、 RaおよびRbは結合点、H、ハロゲンおよび低級アルキルよりなる群から独立 に選ばれ、 Rg、RhおよびRkは結合点、H、低級アルキルおよび-CH2(CH2)na よりなる群 から独立に選ばれ、 Riは結合点、H、ハロゲン、低級アルキル、CN、CF3、フェニル、CO2Hおよ びCONRgRhよりなる群から選ばれ、そして a はHおよび結合点よりなる群から選ばれる〕 の化合物またはその膜透過性蛍光原誘導体である、請求項10に記載の化合物。 42.前記の受容体または消光体が式(VIII): 〔式中、 EはH、OH、ORkおよびNRgRhよりなる群から選ばれ、 GはOおよびN+RgRhよりなる群から選ばれ、 Q'はO、CH2、C(CH3)2およびNRgよりなる群から選ばれ、 Ra、Rb、RcおよびRdは結合点、H、ハロゲンおよび低級アルキルよりなる群 から独立に選ばれ、 Reは結合点、H、低級アルキル、(CH2)nCO2H、(CH2)nCHaCO2H 、CHa(CH2)nC O2H、(CH2)nCOa 、CH=CHCOa、 よりなる群から選ばれ、 Rg、RhおよびRkは結合点、H、低級アルキルおよび-CH2(CH2)na よりなる群 から独立に選ばれ、 n は0〜5の整数であり、 a およびa'はHおよび結合点よりなる群から独立に選ばれる〕 の化合物またはその膜透過性蛍光原誘導体である、請求項11に記載の化合物。 43.前記の供与体が式II-VIIのクマリンおよびその膜透過性蛍光原誘導体よりな る群から選ばれる、請求項42に記載の化合物。 44.Q'がC(CMe2)2で、GがOである請求項43に記載の化合物またはその膜透過性 蛍光原誘導体。 45. よりなる群から選ばれる、請求項43に記載の化合物。 46.試料がβ−ラクタマーゼ活性を含むか否かを判定する方法であって、 試料を、励起した際に蛍光共鳴エネルギー転移を示す請求項1に記載の化合 物と接触させ、 該化合物を励起させ、そして 該試料における蛍光共鳴エネルギー転移の度合を測定する、 ことを含んでなり、その場合、期待量よりも低い蛍光共鳴エネルギー転移度が β−ラクタマーゼ活性の存在を示すことを特徴とする方法。 47.試料中の蛍光共鳴エネルギー転移度の測定が、試料を基質と接触させた後に 第1の時期と第2の時期に蛍光共鳴エネルギー転移度を測定し、その蛍光共鳴エ ネルギー転移度の差を調べることを含んでなり、その場合、蛍光共鳴エネルギー 転移度の差が試料中の酵素の量を表していることを特徴とする、試料中の酵素の 量を測定するための、請求項1に記載の方法。 48.β−ラクタマーゼの発現をコードするヌクレオチド配列に機能的に連結させ た、脊椎動物細胞内で機能するように適合させた発現制御配列を含んでなる組換 え核酸分子。 49.前記のヌクレオチド配列がクラスAβ−ラクタマーゼをコードする、請求項 48に記載の組換え核酸分子。 50.リボソーム結合部位のための哺乳動物Kozak 配列をさらに含む、請求項49に 記載の組換え核酸分子。 51.前記のヌクレオチド配列が図7の配列3または配列4である、請求項50に記 載の組換え核酸分子。 52.前記のヌクレオチド配列が図7の配列1または配列5である、請求項49に記 載の組換え核酸分子。 53.発現制御配列が誘導性の発現制御配列である、請求項48に記載の組換え核酸 分子。 54.発現制御配列が構成的に活性の発現制御配列である、請求項48に記載の組換 え核酸分子。 55.発現制御配列が c-fosプロモーターまたは c-junプロモーターを含む、請求 項48に記載の組換え核酸分子。 56.発現制御配列が環状AMP-応答エレメント、フォルボールエステル応答エレメ ント、血清応答エレメント、または活性化T細胞応答エレメントの核因子を含む 、請求項48に記載の組換え核酸分子。 57.発現制御配列が細胞表面レセプターをモジュレートする物質に応答する、請 求項48に記載の組換え核酸分子。 58.発現制御配列が細胞内レセプターをモジュレートする物質に応答する、請求 項48に記載の組換え核酸分子。 59.β−ラクタマーゼが細胞外分泌のためのシグナル配列を含む、請求項48に記 載の組換え核酸分子。 60.前記のヌクレオチド配列が図7の配列2である、請求項59に記載の組換え核 酸分子。 61.β−ラクタマーゼが細胞質ゾルのβ=ラクタマーゼである、請求項48に記載 の組換え核酸分子。 62.前記のヌクレオチド配列が図7の配列1、配列3、配列4または配列5であ る、請求項61に記載の組換え核酸分子。 63.細胞質ゾルのβ−ラクタマーゼの発現をコードするヌクレオチド配列に機能 的に連結させた、脊椎動物細胞内で機能するように適合させた発現制御配列を含 んでなる組換え核酸分子。 64.前記のヌクレオチド配列がクラスAβ−ラクタマーゼをコードする、請求項 63に記載の組換え核酸分子。 65.前記のヌクレオチド配列が図7の配列1、配列3、配列4または配列5であ る、請求項64に記載の組換え核酸分子。 66.発現制御配列が誘導性の発現制御配列である、請求項63に記載の組換え核酸 分子。 66.発現制御配列が構成的に活性の発現制御配列である、請求項63に記載の組換 え核酸分子。 67.発現制御配列が c-fosプロモーターまたは c-junプロモーターを含む、請求 項63に記載の組換え核酸分子。 68.発現制御配列が環状AMP-応答エレメント、フォルボールエステル応答エレメ ント、血清応答エレメント、または活性化T細胞応答エレメントの核因子を含む 、請求項63に記載の組換え核酸分子。 69.発現制御配列が細胞表面レセプターをモジュレートする物質に応答する、請 求項63に記載の組換え核酸分子。 70.発現制御配列が細胞内レセプターをモジュレートする物質に応答する、請求 項63に記載の組換え核酸分子。 71.β−ラクタマーゼの発現をコードするヌクレオチド配列に機能的に連結させ た、哺乳動物細胞内で機能するように適合させた発現制御配列を含んでなる組換 え核酸分子でトランスフェクトされた哺乳動物宿主細胞。 72.細胞中のβ−ラクタマーゼ活性の量を測定する方法であって、 β−ラクタマーゼの発現をコードする核酸配列に機能的に連結させた発現制 御配列を含んでなる組換え核酸分子でトランスフェクトされた宿主細胞を用意し 、 該細胞もしくは該細胞の抽出物またはならし培地を含む試料をβ−ラクタマ ーゼの基質と接触させ、そして 切断された基質の量を測定する、 ことを含んでなり、その場合、切断された基質の量がβ−ラクタマーゼ活性の 量に関係していることを特徴とする方法。 73.一組の発現制御配列に機能的に連結させた遺伝子の発現をモニターする方法 であって、 β−ラクタマーゼの発現をコードする核酸配列に機能的に連結させた発現制 御配列を含んでなる組換え核酸分子でトランスフェクトされた真核宿主細胞を用 意し、ただし、該真核細胞が真菌である場合はβ−ラクタマーゼが細胞質ゾルの β−ラクタマーゼであり、 該細胞もしくは該細胞の抽出物またはならし培地を含む試料をβ−ラクタマ ーゼの基質と接触させ、そして 切断された基質の量を測定する、 ことを含んでなり、その場合、切断された基質の量がβ−ラクタマーゼ活性の 量に関係していることを特徴とする方法。 74.真核細胞が哺乳動物細胞である、請求項73に記載の方法。 75.試料がならし培地を伴うまたは伴わない前記細胞からの抽出物を含む、請求 項73に記載の方法。 76.試料が細胞を含む、請求項73に記載の方法。 77.前記の基質が請求項1に記載の化合物であり、切断された基質の量を測定す るステップが該化合物を励起させて試料中の蛍光共鳴エネルギー転移度を測定す ることを含み、その場合、期待量よりも低い蛍光共鳴エネルギー転移度がβ−ラ クタマーゼ活性の存在を示す、請求項73に記載の方法。 78.前記のヌクレオチド配列がクラスAβ−ラクタマーゼをコードする、請求項 73に記載の方法。 79.前記のヌクレオチド配列が図7の配列1、配列2、配列3、配列4または配 列5である、請求項78に記載の方法。 80.発現制御配列が誘導性の発現制御配列である、請求項73に記載の方法。 81.前記の細胞が動物細胞であり、β−ラクタマーゼが細胞質ゾルのβ−ラクタ マーゼである、請求項73に記載の方法。 82.試験化合物が一組の発現制御配列に機能的に連結させた遺伝子の発現を変更 するか否かを判定する方法であって、 β−ラクタマーゼの発現をコードする核酸配列に機能的に連結させた発現制 御配列を含んでなる組換え核酸構築物でトランスフェクトされた真核宿主細胞を 用意し、ただし、該真核細胞が真菌である場合はβ−ラクタマーゼが細胞質ゾル のβ−ラクタマーゼであり、 該細胞を試験化合物と接触させ、 該細胞または該細胞の抽出物を含む試料をβ−ラクタマーゼの基質と接触さ せ、そして 切断された基質の量を測定する、 ことを含んでなり、その場合、切断された基質の量がβ−ラクタマーゼ活性の 量に関係していることを特徴とする方法。 83.真核宿主細胞が哺乳動物細胞である、請求項82に記載の方法。 84.試料が細胞からの抽出物を含む、請求項82に記載の方法。 85.試料が細胞を含む、請求項82に記載の方法。 86.前記の基質が請求項1に記載の化合物であり、切断された基質の量を測定す るステップが該化合物を励起させて試料中の蛍光共鳴エネルギー転移度を測定す ることを含み、その場合、期待量よりも低い蛍光共鳴エネルギー転移度がβ−ラ クタマーゼ活性の存在を示す、請求項82に記載の方法。 87.前記のヌクレオチド配列がクラスAβ−ラクタマーゼをコードする、請求項 82に記載の方法。 88.前記のヌクレオチド配列が図7の配列1、配列2、配列3、配列4または配 列5である、請求項87に記載の方法。 89.発現制御配列が誘導性の発現制御配列である、請求項85に記載の方法。 90.前記の細胞が動物細胞であり、β−ラクタマーゼが細胞質ゾルのβ−ラクタ マーゼである、請求項85に記載の方法。 91.β−ラクタマーゼの発現が細胞内レセプター、細胞表面レセプターまたは細 胞内シグナル伝達経路の成分の活性化または活性化の阻害により機能的に調節さ れる、請求項82に記載の方法。 92.細胞質ゾルβ−ラクタマーゼの発現をコードする核酸配列に機能的に連結さ せた発現制御配列を含んでなる組換え核酸分子でトランスフェクトされた細胞を 用意し、 該細胞を該発現制御配列の活性化を活性化するかまたは阻害する物質と接触 させ、 該細胞を、基質に変換される請求項9の化合物と接触させ、 基質が個々の各細胞内で切断されるか否かを調べ、その場合、切断がβ−ラ クタマーゼ活性を示しており、そして 所定のレベルのβ−ラクタマーゼ活性を有する細胞を選択し増殖させる、 ことを含んでなるクローン選択法。 93.選ばれた細胞を、活性化剤の不在下で、切断された基質が該細胞から実質的 に消失しかつβ−ラクタマーゼのレベルが非活性化レベルに戻るのに十分な時間 培養し、 その選ばれた細胞を、基質に変換される請求項9の化合物とともにインキュ ベートし、そして 基質を実質的に切断しなかった細胞を選択する、 ステップをさらに含む請求項92に記載の方法。
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JP2004305450A Expired - Lifetime JP3856807B2 (ja) | 1995-03-20 | 2004-10-20 | β−ラクタマーゼリポーター遺伝子 |
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EP (3) | EP0982398B1 (ja) |
JP (2) | JP3633940B2 (ja) |
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AT (3) | ATE253632T1 (ja) |
AU (1) | AU723164B2 (ja) |
CA (1) | CA2215310C (ja) |
DE (2) | DE69630622T2 (ja) |
DK (2) | DK0982398T3 (ja) |
ES (2) | ES2156994T3 (ja) |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2004043819A (ja) * | 1996-05-03 | 2004-02-12 | Applera Corp | 硬質リンカ―を有するエネルギ―転移色素 |
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