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1. 发明授权

US5362628A Fluorescent haloalkyl derivatives of reporter molecules well retained in cells 失效
标题翻译：报道分子的荧光卤代烷基衍生物保留在细胞中
公开(公告)号：US5362628A
公开(公告)日：1994-11-08
申请号：US26633
申请日：1993-03-05
申请人： Richard P. Haugland , Yu-Zhong Zhang , Ram Sabnis , Nels A. Olson , John J. Naleway , Rosaria P. Haugland
发明人： Richard P. Haugland , Yu-Zhong Zhang , Ram Sabnis , Nels A. Olson , John J. Naleway , Rosaria P. Haugland
IPC分类号： C12Q1/04 , C12Q1/34 , G01N33/535 , C12Q1/00 , A61K37/02 , C07H15/24 , G01N33/40
CPC分类号： C12Q1/04 , C12Q1/34 , G01N33/535 , C12Q2334/00 , C12Q2334/20 , C12Q2334/40 , C12Q2337/20 , G01N2333/924 , Y10S530/802
摘要： The subject invention provides a method for analyzing the metabolic activity in cells by improving the retention of a detectable reporter molecule only in intact cells where a particular enzyme is present. In particular, improved retention results from a two part process involving conjugation of haloalkyl-substituted derivatives of a reporter molecule with intracellular cysteine-containing peptides while unblocking the reporter molecule. The method for analyzing metabolic activity of cells involves the use of a substrate having the formXR-REPORTER-BLOCKwherein -BLOCK is a group selected to be removable by action of a specific analyte, to give REPORTER spectral properties different from those of the substrate,-REPORTER- is a molecule that, when no longer bound to BLOCK by a BLOCK-REPORTER bond, has spectral properities different from those of the substrate, andXR-- is a haloalkyl moiety that can covalently react with an intracellular thiol (Z--S--H) to form a thioether conjugate (Z--S--R--).After the substrate enters the cells, the analyte removes BLOCK to make REPORTER detectable by the change in spectral properties, and the haloalkyl XR reacts with the intracellular thiol to form the thioether conjugate inside the cells, which is well-retained in the cells.
摘要翻译：本发明提供了通过仅在存在特定酶的完整细胞中改善可检测报道分子的保留来分析细胞中的代谢活性的方法。特别地，涉及将报道分子的卤代烷基取代的衍生物与含细胞内半胱氨酸的肽结合的两部分方法的改进的保留结果，同时解除报道分子的阻断。用于分析细胞代谢活性的方法涉及使用具有XR-REPORTER-BLOCK形式的底物，其中-BLOCK是通过特定分析物的作用被选择为可去除的基团，以产生与底物的不同的REPORTER光谱性质 -REPORTER-是一个分子，当不再通过BLOCK-REPORTER键与BLOCK结合时，具有与底物不同的光谱性质，XR-是可以与胞内硫醇（ZSH）共价反应的卤代烷基部分，以形成硫醚缀合物（ZSR-）。在底物进入细胞后，分析物除去BLOCK以通过光谱性质的变化使REPORTER可检测到，并且卤代烷基XR与细胞内硫醇反应以在细胞内形成硫醚缀合物，其在细胞中良好保留。

2. 发明授权

US5576424A Haloalkyl derivatives of reporter molecules used to analyze metabolic activity in cells 失效
标题翻译：用于分析细胞代谢活性的报道分子的卤代烷基衍生物
公开(公告)号：US5576424A
公开(公告)日：1996-11-19
申请号：US336285
申请日：1994-11-08
申请人： Fei Mao , Ram Sabnis , John Naleway , Nels Olson , Richard P. Haugland
发明人： Fei Mao , Ram Sabnis , John Naleway , Nels Olson , Richard P. Haugland
IPC分类号： C12Q1/04 , C12Q1/34 , G01N33/535 , C07H17/00 , C07D309/00
CPC分类号： G01N33/535 , C12Q1/04 , C12Q1/34 , C12Q2334/00 , C12Q2334/20 , C12Q2334/40 , C12Q2337/20 , G01N2333/924
摘要： The subject invention provides substrates useful for analyzing the metabolic activity in cells by improving the retention of a detectable reporter molecule only in intact cells where a particular enzyme is present. In particular, improved retention results from a two part process involving conjugation of haloalkyl-substituted derivatives of a reporter molecule with intracellular cysteine-containing peptides while unblocking the reporter molecule. The substrates have the formXR-SPACER-REPORTER-BLOCKwherein -BLOCK is a group selected to be removable by action of a specific analyte, to give REPORTER spectral properties different from those of the substrate,-REPORTER- is a molecule that, when no longer bound to BLOCK by a BLOCK-REPORTER bond, has spectral properties different from those of the substrate,-SPACER- is a covalent linkage, andXR- is a haloalkyl moiety that can covalently react with an intracellular thiol (Z-S-H) to form a thioether conjugate (Z-S-R-).After the substrate enters the cells, the analyte removes BLOCK to make REPORTER detectable by the change in spectral properties, and the haloalkyl XR reacts with the intracellular thiol to form the thioether conjugate inside the cells, which is well-retained in the cells.
摘要翻译：本发明提供了用于通过仅在存在特定酶的完整细胞中改善可检测报道分子的保留来分析细胞中代谢活性的底物。特别地，涉及将报道分子的卤代烷基取代的衍生物与含细胞内半胱氨酸的肽结合的两部分方法的改进的保留结果，同时解除报道分子的阻断。底物具有形式XR-SPACER-REPORTER-BLOCK，其中-BLOCK是选择通过特定分析物的作用可除去的基团，使得REPORTER光谱性质与底物不同，-REPORTER-是不再存在的分子通过BLOCK-REPORTER键与BLOCK结合，具有与底物不同的光谱性质，-SPACER-是共价连接，XR-是可与胞内硫醇（ZSH）共价反应形成硫醚的卤代烷基部分缀合物（ZSR-）。在底物进入细胞后，分析物除去BLOCK以通过光谱性质的变化使REPORTER可检测到，并且卤代烷基XR与细胞内硫醇反应以在细胞内形成硫醚缀合物，其在细胞中良好保留。

3. 发明公开

EP0452330A1 METHOD AND APPARATUS FOR DIAGNOSING INTRACELLULAR PARASITE INFECTIONS USING AN ENZYME DETECTION SYSTEM 失效
标题翻译：装置和方法与使用酶活性检测系统故障诊断的细胞内寄生虫感染。
公开(公告)号：EP0452330A1
公开(公告)日：1991-10-23
申请号：EP89912177.0
申请日：1989-10-25
申请人： TOTEM HEALTH SCIENCES, INC. , MAKLER, Michael T.
发明人： MAKLER, Michael, T.
IPC分类号： C12M1 , A61K49 , C12Q1
CPC分类号： C12Q1/34 , C12Q2337/20 , G01N2333/445 , G01N2333/948 , Y02A50/58
摘要： The present invention involves a highly specific chemical system for detecting parasite-infected cells. The method is especially effective in detecting intraerythrocytic diseases, especially malaria. With respect to malaria, chemical agents are used to detect enzymes produced by the infecting parasites. Blood samples are combined with a plurality of substrates which are subjected to enzymatic hydrolysis. Hydrolysis is rapid and may be detected in two ways. The first method involves substrates having a fluorescent detecting group. Upon hydrolysis, the fluorescent group is cleaved and detected using a conventional fluorescent light source. Alternatively, substrates may be used having a detecting group which forms a visibly colored material when combined with a secondary reagent. These techniques produce a unique colored or fluorescent pattern which enables the rapid and accurate determination of parasite infection. Furthermore, parasite diagnosis is accomplished without the use of expensive and complex diagnostic equipment.

4. 发明申请

US20080026365A1 HEMOSTASIS ASSAY 有权
标题翻译： HEMOSTASIS测定
公开(公告)号：US20080026365A1
公开(公告)日：2008-01-31
申请号：US11774843
申请日：2007-07-09
申请人： Waander Van Heerde
发明人： Waander Van Heerde
IPC分类号： C12Q1/34 , C12Q1/70
CPC分类号： C12Q1/56 , C12Q2337/20
摘要： Provided is a hemostasis assay comprising a reaction mixture comprising a blood product to be tested, a trigger molecule for inducing thrombin generation, a thrombin-specific substrate which, upon cleavage by thrombin, produces a measurable thrombin-specific signal, a trigger molecule for inducing plasmin generation, a plasmin-specific substrate which, upon cleavage by plasmin, produces a measurable plasmin-specific signal, a phospholipid-containing surface, and calcium ions. The assay allows determination of the amount of thrombin and the amount of plasmin generated in the reaction mixture in time, starting at t=0, by measuring the thrombin-specific and plasmin-specific signals.
摘要翻译：提供一种止血测定法，其包括包含待测试的血液制品，用于诱导凝血酶产生的触发分子的反应混合物，凝血酶切割后产生可测量的凝血酶特异性信号的凝血酶特异性底物，用于诱导的触发分子纤溶酶产生，纤溶酶特异性底物，其在由纤溶酶切割后产生可测量的纤溶酶特异性信号，含磷脂的表面和钙离子。该测定法通过测量凝血酶特异性和纤溶酶原特异性信号，从t = 0开始测定凝血酶的量和反应混合物中产生的纤溶酶量。

5. 发明授权

US4388233A Synthetic substrates for enzyme analysis 失效
标题翻译：用于酶分析的合成底物
公开(公告)号：US4388233A
公开(公告)日：1983-06-14
申请号：US264118
申请日：1981-05-15
申请人： Eugene R. Bissell , Alexander R. Mitchell , Karen W. Pearson , Robert E. Smith
发明人： Eugene R. Bissell , Alexander R. Mitchell , Karen W. Pearson , Robert E. Smith
IPC分类号： C07D311/16 , C07D311/80 , C07K5/068 , C07K5/083 , C07K5/09 , C12Q1/34 , C07C103/52 , C07D311/06
CPC分类号： C07D311/16 , C07D311/80 , C07K5/06086 , C07K5/0806 , C07K5/0815 , C12Q1/34 , C12Q2337/20
摘要： Synthetic substrates are provided which may be represented as A-D. The A moiety thereof includes an amino acid, polypeptide, or derivative thereof. The D moiety thereof includes 7-amino coumarin derivatives having an electron withdrawing substituent group at the 3 position carbon or fused between the 3 and 4 position carbons.
摘要翻译：提供可以表示为A-D的合成基底。其A部分包括氨基酸，多肽或其衍生物。其D部分包括在3位碳上具有吸电子取代基或在3和4位碳之间融合的7-氨基香豆素衍生物。

6. 发明公开

EP0516532A1 Dérivés de coumarines hydrosolubles, leur préparation et leur utilisation comme substrat d'enzyme ou pour la préparation de tels substrats 失效
标题翻译：水溶性Cumarderivate，它们的制备以及它们作为酶的底物或用于这样的基材的制备中使用。
公开(公告)号：EP0516532A1
公开(公告)日：1992-12-02
申请号：EP92401443.4
申请日：1992-05-26
申请人： LABORATOIRES EUROBIO
发明人： Chalom, Joseph , Griffoul, Christine , Tod, Michel , Reveilleau, Stéphane
IPC分类号： C07D311/20 , C07D491/16 , C07C69/716 , C12Q1/37
CPC分类号： C12Q1/37 , C07C69/716 , C07D311/16 , C07D311/20 , C07D311/58 , C12Q2337/20
摘要： L'invention concerne des dérivés de coumarine hydrosolubles.
Ces dérivés répondent à la formule :

dans laquelle R¹ représente

(OCH₂CH₂) m OCH₂R⁷ ou
(OCH(CH₃)CH₂) m OCH₂R⁷

avec m=1 à 30 et R⁷ pouvent être un atome d'hydrogène ou divers groupements, R² à R⁶ pouvent être différents substituants, en particulier des substituants permettant d'introduire dans le dérivé un groupe approprié comme substrat d'enzyme ou pour la synthèse de substrats d'enzymes.
摘要翻译：水溶性香豆素衍生物。这些衍生物对应于下式：其中R <1> darstellt - （OCH2CH2）mOCH2R <7>或 - （OCH（CH 3）CH 2）mOCH2R <7>其中m = 1至30且R <7>可以是氢原子或各种基团，R <2>至R <6>可以是各种取代基，特别是取代基，其使得可以引入，进衍生物，组中的所有适合作为酶的底物或用于合成酶的底物。

7. 发明授权

US08809006B2 Hemostasis assay 有权
标题翻译：止血试验
公开(公告)号：US08809006B2
公开(公告)日：2014-08-19
申请号：US11774843
申请日：2007-07-09
申请人： Waander Laurens Van Heerde
发明人： Waander Laurens Van Heerde
IPC分类号： C12Q1/56
CPC分类号： C12Q1/56 , C12Q2337/20
摘要： Provided is a hemostasis assay comprising a reaction mixture comprising a blood product to be tested, a trigger molecule for inducing thrombin generation, a thrombin-specific substrate which, upon cleavage by thrombin, produces a measurable thrombin-specific signal, a trigger molecule for inducing plasmin generation, a plasmin-specific substrate which, upon cleavage by plasmin, produces a measurable plasmin-specific signal, a phospholipid-containing surface, and calcium ions. The assay allows determination of the amount of thrombin and the amount of plasmin generated in the reaction mixture in time, starting at t=0, by measuring the thrombin-specific and plasmin-specific signals.
摘要翻译：提供一种止血测定法，其包括包含待测试的血液制品，用于诱导凝血酶产生的触发分子的反应混合物，凝血酶切割后产生可测量的凝血酶特异性信号的凝血酶特异性底物，用于诱导的触发分子纤溶酶产生，纤溶酶特异性底物，其在由纤溶酶切割后产生可测量的纤溶酶特异性信号，含磷脂的表面和钙离子。该测定法通过测量凝血酶特异性和纤溶酶原特异性信号，从t = 0开始测定凝血酶的量和反应混合物中产生的纤溶酶量。

8. 再颁专利

USRE38723E1 Haloalkyl derivatives of reporter molecules used to analyze metabolic activity in cells 失效
标题翻译：用于分析细胞代谢活性的报道分子的卤代烷基衍生物
公开(公告)号：USRE38723E1
公开(公告)日：2005-04-12
申请号：US08910090
申请日：1997-08-12
申请人： Fei Mao , Ram Sabnis , John Naleway , Nels Olson , Richard P. Haugland
发明人： Fei Mao , Ram Sabnis , John Naleway , Nels Olson , Richard P. Haugland
IPC分类号： C12Q1/04 , C12Q1/34 , G01N33/535 , C07H17/00 , C07D309/00
CPC分类号： G01N33/535 , C12Q1/04 , C12Q1/34 , C12Q2334/00 , C12Q2334/20 , C12Q2334/40 , C12Q2337/20 , G01N2333/924
摘要： The subject invention provides substrates useful for analyzing the metabolic activity in cells by improving the retention of a detectable reporter molecule only in intact cells where a particular enzyme is present. In particular, improved retention results from a two part process involving conjugation of haloalkyl-substituted derivatives of a reporter molecule with intracellular cysteine-containing peptides while unblocking the reporter molecule. The substrates have the form XR-SPACER-REPORTER-BLOCK wherein -BLOCK is a group selected to be removable by action of a specific analyte, to give REPORTER spectral properties different from those of the substrate, -REPORTER- is a molecule that, when no longer bound to BLOCK by a BLOCK-REPORTER bond, has spectral properties different from those of the substrate, -SPACER- is a covalent linkage, and XR- is a haloalkyl moiety that can covalently react with an intracellular thiol (Z-S-H) to form a thioether conjugate (Z-S-R). After the substrate enters the cells, the analyte removes BLOCK to make REPORTER detectable by the change in spectral properties, and the haloalkyl XR reacts with the intracellular thiol to form the thioether conjugate inside the cells, which is well-retained in the cells.

9. 发明授权

US5342970A Hydrosoluble coumarin derivatives, their preparation and their use as an enzyme substrate or for the preparation of such substrates 失效
标题翻译：可溶性香豆素衍生物，它们的制备及其作为酶底物的用途或用于制备这些底物
公开(公告)号：US5342970A
公开(公告)日：1994-08-30
申请号：US887767
申请日：1992-05-22
申请人： Joseph Chalom , Christine Griffoul , Michel Tod , Stephane Reveilleau
发明人： Joseph Chalom , Christine Griffoul , Michel Tod , Stephane Reveilleau
IPC分类号： C07C69/716 , C07D311/06 , C07D311/16 , C07D311/20 , C07D311/58 , C07D405/12 , C07D491/16 , C12Q1/37 , G01N33/535 , C07D311/04
CPC分类号： C12Q1/37 , C07C69/716 , C07D311/16 , C07D311/20 , C07D311/58 , C12Q2337/20
摘要： The invention relates to hydrosoluble coumarin derivatives. These derivatives comply with the formula: ##STR1## in which R.sup.1 represents ##STR2## with m=1 to 30 and in which R.sup.7 can be a hydrogen atom or various groups, R.sup.2 to R.sup.6 can be different substituents, particularly substituents making it possible to introduce into the derivative an appropriate group as the enzyme substrate or for the synthesis of enzyme substrates.
摘要翻译：本发明涉及水溶性香豆素衍生物。这些衍生物符合下式：其中R1表示（OCH2CH2）mOCH2R7或（OCH（CH3）CH2）mOCH2R7，m = 1-30，其中R7可以是氢原子或各种基团，R2 到R6可以是不同的取代基，特别是取代基，使得可能将合适的基团引入衍生物作为酶底物或用于合成酶底物。

10. 发明申请

WO1993004192A1 USE OF HALOALKYL DERIVATIVES OF REPORTER MOLECULES TO ANALYZE METABOLIC ACTIVITY IN CELLS 审中-公开
标题翻译：报告分子的HALOALKYL衍生物用于分析细胞中的代谢活性
公开(公告)号：WO1993004192A1
公开(公告)日：1993-03-04
申请号：PCT/US1992007068
申请日：1992-08-21
申请人： MOLECULAR PROBES, INC.
发明人： MOLECULAR PROBES, INC. , HAUGLAND, Richard, P.
IPC分类号： C12Q01/00
CPC分类号： C12Q1/04 , C12Q1/34 , C12Q2334/00 , C12Q2334/20 , C12Q2334/40 , C12Q2337/20 , G01N33/535 , G01N2333/924 , Y10S530/802
摘要： The subject invention provides a method for analyzing the metabolic activity in cells by improving the retention of a detectable reporter molecule only in intact cells where a particular enzyme is present. In particular, improved retention results from a two part process involving conjugation of haloalkyl-substituted derivatives of a reporter molecule with intracellular cysteine-containing peptides while unblocking the reporter molecule. The method for analyzing metabolic activity of cells involves the use of a substrate having the form XR-REPORTER-BLOCK wherein -BLOCK is a group selected to be removable by action of a specific analyte, to give REPORTER spectral properties different from those of the substrate, -REPORTER- is a molecule that, when no longer bound to BLOCK by a BLOCK-REPORTER bond, has spectral properties different from those of the substrate, and XR- is a haloalkyl moiety that can covalently react with an intracellular thiol (Z-S-H) to form a thioether conjugate (Z-S-R-). After the substrate enters the cells, the analyte removes BLOCK to make REPORTER detectable by the change in spectral properties, and the haloalkyl XR reacts with the intracellular thiol to form the thioether conjugate inside the cells, which is well-retained in the cells.
摘要翻译：本发明提供了通过仅在存在特定酶的完整细胞中改善可检测报道分子的保留来分析细胞中的代谢活性的方法。特别地，涉及将报道分子的卤代烷基取代的衍生物与含细胞内半胱氨酸的肽结合的两部分方法的改进的保留结果，同时解除报道分子的阻断。用于分析细胞代谢活性的方法涉及使用具有XR-REPORTER-BLOCK形式的底物，其中-BLOCK是通过特定分析物的作用选择为可除去的基团，以产生与底物相反的REPORTER光谱性质，-REPORTER-是当不再通过BLOCK-REPORTER键与BLOCK结合的分子时，具有与底物不同的谱特性，XR-是可与胞内硫醇（ZSH）共价反应的卤代烷基部分，以形成硫醚缀合物（ZSR-）。在底物进入细胞后，分析物除去BLOCK以通过光谱性质的变化使REPORTER可检测到，并且卤代烷基XR与细胞内硫醇反应以在细胞内形成硫醚缀合物，其在细胞中良好保留。

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