JP2001514492A - 生物学的サンプル中のプロテアーゼの検出のための組成物及びその使用方法 - Google Patents
生物学的サンプル中のプロテアーゼの検出のための組成物及びその使用方法Info
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- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
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- C12Q1/34—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving hydrolase
- C12Q1/37—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving hydrolase involving peptidase or proteinase
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- G01N33/536—Immunoassay; Biospecific binding assay; Materials therefor with immune complex formed in liquid phase
- G01N33/542—Immunoassay; Biospecific binding assay; Materials therefor with immune complex formed in liquid phase with steric inhibition or signal modification, e.g. fluorescent quenching
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- G01N2333/964—Proteinases, i.e. endopeptidases (3.4.21-3.4.99) derived from animal tissue
- G01N2333/96425—Proteinases, i.e. endopeptidases (3.4.21-3.4.99) derived from animal tissue from mammals
- G01N2333/96427—Proteinases, i.e. endopeptidases (3.4.21-3.4.99) derived from animal tissue from mammals in general
- G01N2333/9643—Proteinases, i.e. endopeptidases (3.4.21-3.4.99) derived from animal tissue from mammals in general with EC number
- G01N2333/96466—Cysteine endopeptidases (3.4.22)
- G01N2333/96469—Interleukin 1-beta convertase-like enzymes
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Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.プロテアーゼの活性の検出のための螢光原組成物であって、 下記式: 〔式中、Pは、前記プロテアーゼのためのプロテアーゼ結合部位を含んで成るペ プチドであり、前記結合部位は、約2〜約8個のアミノ酸から成り; F1及びF2は螢光団であり、そしてF1はアミノ末端アミノ酸に結合され、そ してF2はカルボキシル末端アミノ酸に結合され; S及びS2は、存在する場合、1〜約50個の長さのアミノ酸の範囲のペプチド スペーサーであり、そしてS1は、存在する場合、アミノ末端アミノ酸に結合さ れ、そしてS2は、存在する場合、カルボキシル末端アミノ酸に結合され; i,j,k,l,m,n,o p,q及びrは独立して、0又は1であり; aa1及びaa10は、リジン、オルニチン及びシステインから成る群から独立して 選択され; aa2,a3,aa8及びaa9は、Asp、Glu、Lys、オルニチン、Arg、シトルリン、ホ モシトルリン、Ser、ホモセリン、Thr及びTyrから成るアミノ酸又はジペプチド から成る群から独立して選択され; aa5,aa4,aa6及びaa7は、プロリン、3,4−デヒドロプロリン、ヒドロキシ プロリン、α−アミノイソ酪酸及びN−メチルアラニンから成る群から独立して 選択され; Xは、Gly,βAla,γAbu,Gly-Gly,Ahx,βAla-Gly,βAla-βAla, γAbu-Gly,βAla-γAbu,Gly-Gly-Gly,γAbu-γAbu,Ahx-Gly,βAla-Gly-Gly, Ahx-βAla,βAla-βAla-Gly,Gly-Gly-Gly-Gly,Ahx-γAbu,βAla-βAla-βAla, γAbu-βAla-Gly,γAbu-γAbu-Gly,Ahx-Ahx,γAbu-γAbu-βAla、及びAhx-Ahx -Glyから成る群から選択され; Yは、Gly,βAla,γAbu,Gly-Gly,Ahx,Gly-βAla,βAla-βAla,Gly-γAbu,γ Abu-βAla,Gly-Gly-Gly,γAbu-γAbu,Gly-Ahx,Gly-Gly-βAla,βAla-Ahx,Gl y-βAla-βAla,Gly-Gly-Gly-Gly,γAbu-Ahx,βAla-βAla-βAla,Gly-βAla- γAbu,Gly-γAbu-γAbu,Ahx-Ahx,βAla-γAbu-γAbu、及びGly-Ahx-Ahxから成 る群から選択され; iが1である場合、S1は、aa1の末端αアミノ基を通してペプチド結合により aa1に結合され;そして γが1である場合、S2は、aa10の末端αカルボキシル基を通してペプチド結 合によりaa12に結合される〕を 有する組成物。 2.Pが、TGRTG,DEVDGID,DEVNGID,EVDGID,ADGID,DEVDGID,AIPMSI,GDE VDGID,GDEVDGIN,ADGID,GNEVDGID,GNEVDGIN,ODEVDGID,dODEVDGID,WDEVDGI D,dVVDEVDGID,dOdODEVDGID,dWdWDEVDGID,YVADGID,YVADGIN,YVANGIN,YVAD GID,YVANGIN、及びdYVADGINから成る群から選択される請求の範囲第1項記載の 組成物。 3.Pが、LVEIDNG,LVEINNG,GIETDSGVDD,GIETNSGVDD,GIETNSGV,GIETDSGV ,GSESMDSGISLD,GSESMDSG,DVVCCSMS,DVVCDSMS,DVVCSdMS,DVVCCPdMS,EDVVC CS,EDdVVCCP,EDdVVCDP,DdVVCCSdMS,DVdVCDSdMS,DdVVCCPdMS,DVVCCSM,DVV CDSM,VCCSM、及びVCDSMから成る群から選択される請求の範囲第1項記載の組成 物。 4.Pが、DEMEECSQHL,DEMEECPQHL,EMEECSQHL,EMEECPQHL,EM EEDSQHL,VMTGRTG,VdMTGRTG,VMTGRG,VdMTGRG,VMTGRVG,VdMTGRVG,VMTGRAG ,VdMTGRAG,SEVNLDAEF,SEVKLDAEF,SEVKMDAEF,SEVKMDDEF,SEVNLDDEF,GVVIA TVIVT,YGVVIATVIVIT,VIATVI,YGVVIA,QQLLNH,SIQYTY,SSQYSN、及びSSIYSQ から成る群から選択される請求の範囲第1項記載の組成物。 5.前記F1及びF2が同じ螢光団である請求の範囲第1項記載の組成物。 6.前記F1及びF2が約315nm〜約700nmの間での励起波長を有する請求の範囲 第5項記載の組成物。 7.前記F1分子が、aa1アミノ酸のα−アミノ基、aa1アミノ酸の側鎖アミノ 基、又はaa1アミノ酸の側鎖のスルフヒドリル基のいづれかを通して結合される 請求の範囲第1項記載の組成物。 8.前記F2分子が、aa10アミノ酸の側鎖アミノ基、aa10アミノ酸のカルボキ シル基、又はaa10アミノ酸の側鎖のスルフヒドリル基のいづれかを通して結合さ れる請求の範囲第1項記載の組成物。 9.前記螢光団が、カルボキシテトラメチルローダミン、カルボキシローダミ ン−X及びジエチルアミノクマリン、9−(2,5−ジカルボキシフェニル)− 3,6−ビス(ジメチルアミノ)キサンリウムクロリド(5−TMR)、9−(2, 6−ジカルボキシフェニル)−3,6−ビス(ジメチルアミノ)キサンチリウム クロリド(6−TMR)、9−(2−カルボキシフェニル)−2,7−ジメチル−3 ,6−ビス(エチルアミノ)キサンチリウム、9−(2−カルボキシフェニル) −3,6−ビス(ジメチルアミノ)キサンチリウム及び9−(2−カルボキシフ ェニル)キサンチリウムから成る群から選択される請求の範囲第1項記載の組成 物。 10.前記組成物が、疎水性基を担持する請求の範囲第1項記載の組成物。 11.前記疎水性基が、Fmoc、ベンジルオキシカルボニル、キサンチル(Xan)、 トリチル(Trt)、4−メチルトリチル(Mtt)、4−メトキシトリチル(Mmt)、4− メトキシ−2,3,6−トリメチル−ベンゼンスルホニル(Mtr)、メシチレン− 2−スルホニル(Mts)、4,4’−ジメトキシベンズヒドリル(Mbh)、トシル(Tos )、2,2,5,7,8−ペンタメチルクロマン−6−スルホニル(Pmc)、4−メ チルベンジル(MeBzl)、4−メトキシベンジル(MeOBzl)、ベンジルオキシ(Bzl O)、ベンジル(Bzl)、ベンゾイル(Bz)、3−ニトロ−2−ピリジンスルフェニ ル(Npys)、1−(4, 4−ジメチル−2,6−ジアキソシクロヘキシリデン )エチル(Dde)、2,6−ジクロロベンジル(2,6−DiCl−Bzl)、2−クロロベ ンジルオキシカルボニル(2−Cl−Z)、2−ブロモベンジルオキシカルボニル (2−Br−Z)、ベンジルオキシメチル(Bom)、t−ブトキシカルボニル(Boc)、 シクロヘキシルオキシ(cHxO)、t−ブトキシメチル(Bum)、t−ブトキシ(tBU O)、t−ブチル(tBu)、アセチル(Ac)、及びトリフルオロアセチル(TFA)から 成る群から選択される請求の範囲第10項記載の組成物。 12.前記疎水性基がFmocである請求の範囲第11項目記載の組成物。 13.前記疎水性基が、前記分子のアミノ末端に結合される請求の範囲第11項記 載の組成物。 14.前記組成物が、PAI−2,DEVD,DEVN,PARP,ICE,Fm-DEVD,Fm-FmDEVN, Fm-PARP,Fm-KNFES,Fm-G2D2D,Fm-CGD2D,Z-CGD2D、及びFm-ICEと称する組成物 から成る群から選択される請求の範囲第1項記載の組成物。 15.プロテアーゼの活性を検出するための方法であって、前記プロテアーゼと 請求の範囲第1項記載の組成物とを接触せしめること を含んで成る方法。 16.前記接触が組織学的断片において存在する請求の範囲第15項記載の方法。 17.前記接触が、組織、血液、尿、唾液、リンパ、生検体から成る群から選択 された生物学的サンプルに由来する細胞懸濁液において存在する請求の範囲第15 項記載の方法。 18.前記検出が、螢光顕微鏡、螢光マイクロプレートリーダー、フローサイト メトリー(流動細胞計測)法、螢光測定法、吸収分光分析法から成る群から選択 された方法による請求の範囲第15項記載の方法。 19.分子のコンホメーションの変化を検出するための方法であって、 第1螢光団及び第2螢光団をそれに結合している第1分子を用意し、ここで前 記第1螢光団及び前記第2螢光団は同じ種の螢光団であり、そして前記螢光団が 、同じ位置で前記分子に結合される単一の螢光団の螢光強度に比較して、前記螢 光団の個々の螢光強度を検出できるほどに低めるために前記螢光団の相互作用の ための十分な距離で並置され;そして 前記螢光団間の空間が、前記分子のコンホメーションの前記変化により広くさ れるにつれて、螢光の変化を検出することを含んで成る方法。 20.前記螢光団が、空間の広がりの前、H−タイプのダイマーを形成する請求 の範囲第19項記載の方法。 21.前記螢光団がお互い約10Å以下の距離で存在する請求の範囲第19項記載の 方法。 22.前記螢光団が、カルボキシテトラメチルローダミン、カルボキシローダミ ン−X及びジエチルアミノクマリン、テトラメチルロ ーダミン、ジエチルローダミン、及びローダミン110から成る群から選択される 請求の範囲第19項記載の方法。 23.前記コンホメーションの変化が、螢光団の1つをそれぞれ担持する2種の 異なった分子に前記分子を分割する請求の範囲第19項記載の方法。 24.前記コンホメーションの変化が、前記第1分子への第2分子の結合により 生成される請求の範囲第19項記載の方法。 25.前記分子が、核酸、多糖、ペプチド、タンパク質、脂質、リン脂質、糖脂 質、糖タンパク質、ステロイドから成る群から選択される請求の範囲第19項記載 の方法。 26.前記分子が核酸であり、そして前記コンホメーションの変化がもう1つの 核酸への前記核酸のハイブリダイゼーションにより生成される請求の範囲第19項 記載の方法。 27.前記分子が核酸であり、そして前記コンホメーションの変化が前記核酸の 分解により生成される請求の範囲第19項記載の方法。 28.前記分子が多糖であり、そして前記コンホメーションの変化が前記多糖の 分解により生成される請求の範囲第19項記載の方法。 29.組成物のコンホメーションの変化を検出するための螢光原組成物であって 、第1螢光団及び第2螢光団をそれに結合している分子を含んで成り、ここで前 記第1螢光団及び第2螢光団は同じ種の螢光団であり、そして前記螢光団が、同 じ位置で前記分子に結合されるそれぞれ個々の螢光団の螢光強度に比較して、前 記螢光団の個々の螢光強度を検出できるほどに低めるために前記螢光団の相互作 用のための十分な距離で並置されることを特徴とする組成物。 30.細胞中に分子を供給するための方法であって、 疎水性基に、及び2種の螢光団に又は少なくとも1つの融合された環構造体の いづれかに結合される前記分子を用意し;そして 前記細胞と前記分子とを接触せしめ、それによって、前記分子が前記細胞中に 侵入する方法。 31.前記分子が、核酸及びポリペプチドから成る群から選択される請求の範囲 第30項記載の方法。 32.前記融合された環構造体が、生物学的に不活性化されたステロイドである 請求の範囲第30項記載の方法。 33.前記疎水性基が、Fmoc、ベンジルオキシカルボニル、キサンチル(Xan)、 トリチル(Trt)、4−メチルトリチル(Mtt)、4−メトキシトリチル(Mmt)、4− メトキシ−2,3,6−トリメチル−ベンゼンスルホニル(Mtr)、メシチレン− 2−スルホニル(Mts)、4,4’−ジメトキシベンズヒドリル(Mbh)、トシル(Tos )、2,2,5,7,8−ペンタメチルクロマン−6−スルホニル(Pmc)、4−メチ ルベンジル(MeBzl)、4−メトキシベンジル(MeOBzl)、ベンジルオキシ(BzlO )、ベンジル(Bzl)、ベンゾイル(Bz)、3−ニトロ−2−ピリジンスルフェニ ル(Npys)、1−(4,4−ジメチル−2,6−ジアキソシクロヘキシリデン) エチル(Dde)、2,6−ジクロロベンジル(2,6−DiCl−Bzl)、2−クロロベン ジルオキシカルボニル(2−Cl−Z)、2−ブロモベンジルオキシカルボニル( 2−Br−Z)、ベンジルオキシメチル(Bom)、t−ブトキシカルボニル(Boc)、シ クロヘキシルオキシ(cHxO)、t−ブトキシメチル(Bum)、t−ブトキシ(tBuO )、t−ブチル(tBu)、アセチル(Ac)、及びトリフルオロアセチル(TFA)から成 る群から選択される請求の範囲第30項記載の方法。 34.前記螢光団が、カルボキシテトラメチルローダミン、カルボキシローダミ ン−X及びジエチルアミノクマリンから成る群から選択される請求の範囲第30項 記載の方法。 35.前記細胞が哺乳類細胞である請求の範囲第30項記載の方法。
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US08/802,981 US6037137A (en) | 1997-02-20 | 1997-02-20 | Fluorogenic peptides for the detection of protease activity |
PCT/US1998/003000 WO1998037226A1 (en) | 1997-02-20 | 1998-02-20 | Compositions for the detection of enzyme activity in biological samples and methods of use thereof |
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1997
- 1997-02-20 US US08/802,981 patent/US6037137A/en not_active Expired - Lifetime
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1998
- 1998-02-20 WO PCT/US1998/003000 patent/WO1998037226A1/en active IP Right Grant
- 1998-02-20 AU AU66567/98A patent/AU745148B2/en not_active Ceased
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- 1998-02-20 JP JP53677898A patent/JP4298796B2/ja not_active Expired - Fee Related
- 1998-02-20 EP EP98908564A patent/EP0988394B1/en not_active Expired - Lifetime
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1999
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DE69841419D1 (de) | 2010-02-11 |
WO1998037226A1 (en) | 1998-08-27 |
US6936687B1 (en) | 2005-08-30 |
JP4298796B2 (ja) | 2009-07-22 |
US6037137A (en) | 2000-03-14 |
CA2280811C (en) | 2015-11-03 |
AU745148B2 (en) | 2002-03-14 |
US7879574B2 (en) | 2011-02-01 |
EP0988394A1 (en) | 2000-03-29 |
EP0988394A4 (en) | 2003-04-23 |
ATE453722T1 (de) | 2010-01-15 |
EP0988394B1 (en) | 2009-12-30 |
AU6656798A (en) | 1998-09-09 |
CA2280811A1 (en) | 1998-08-27 |
US20080199898A1 (en) | 2008-08-21 |
JP2008167757A (ja) | 2008-07-24 |
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