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1. 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。

2. 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.

3. 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。

4. 发明授权

US6004536A Lipophilic cyanine dyes with enchanced aqueous solubilty 失效
标题翻译：具有增溶水溶性的亲油花青染料
公开(公告)号：US6004536A
公开(公告)日：1999-12-21
申请号：US702396
申请日：1996-08-14
申请人： Wai-Yee Leung , Richard P. Haugland , Fei Mao
发明人： Wai-Yee Leung , Richard P. Haugland , Fei Mao
IPC分类号： A61K49/00 , C07D209/14 , C07D263/56 , C07D413/06 , C07D413/14 , C09B23/01 , C09B23/02 , G01N1/30 , C07D209/04 , C07D403/06 , G01N33/48
CPC分类号： C07D263/56 , A61K49/006 , C07D209/14 , C07D413/06 , C07D413/14 , C09B23/0066 , C09B23/02 , G01N1/30 , Y10T436/14 , Y10T436/141111 , Y10T436/142222 , Y10T436/145555
摘要： The present invention relates to a family of cyanine dyes possessing lipophilic alkyl chains and either one or more reactive functional groups, bromo or chloro, or phenyl, sulfophenyl or polysulfophenyl substituents or combinations thereof. The dyes of the invention are useful for staining membranes in cells or isolated from cells, and are well-retained therein. Additionally, the reactive dyes of the invention are useful for preparing dye-conjugates, thereby conferring the membrane staining ability of the subject dye onto the resulting dye-conjugate.
摘要翻译：本发明涉及一种具有亲脂性烷基链和一个或多个反应性官能团，溴或氯或苯基，磺基苯基或多磺基苯基取代基或其组合的花青染料族。本发明的染料可用于染色细胞中的膜或从细胞中分离，并且保留在其中。此外，本发明的活性染料可用于制备染料缀合物，从而赋予受试染料在所得染料缀合物上的膜染色能力。

5. 发明授权

US6130101A Sulfonated xanthene derivatives 失效
标题翻译：磺化呫吨衍生物
公开(公告)号：US6130101A
公开(公告)日：2000-10-10
申请号：US935963
申请日：1997-09-23
申请人： Fei Mao , Wai-Yee Leung , Richard P. Haugland
发明人： Fei Mao , Wai-Yee Leung , Richard P. Haugland
IPC分类号： G01N33/48 , C07D311/82 , C07D405/12 , C07D491/14 , C07D491/147 , C07D491/22 , C07H21/00 , C07H21/04 , C09B11/08 , C09B11/24 , C09B11/28 , G01N1/30 , G01N33/533 , C07K16/12 , C07K16/18 , G01N33/554
CPC分类号： C07D405/12 , C07D311/82 , C07D491/14 , C07H21/00 , C09B11/08 , C09B11/24 , Y10S436/80 , Y10S436/827 , Y10S436/829
摘要： The present invention describes xanthene dyes, including rhodamines, rhodols and fluoresceins that are substituted one or more times by a sulfonic acid or a salt of a sulfonic acid. The dyes of the invention, including chemically reactive dyes and dye-conjugates are useful as fluorescent probes, particularly in biological samples.
摘要翻译：本发明描述了呫吨染料，包括被磺酸或磺酸盐一次或多次取代的罗丹明，罗丹明和荧光素。本发明的染料，包括化学活性染料和染料缀合物，可用作荧光探针，特别是在生物样品中。

6. 发明授权

US6162931A Fluorinated xanthene derivatives 失效
标题翻译：氟化呫吨衍生物
公开(公告)号：US6162931A
公开(公告)日：2000-12-19
申请号：US631202
申请日：1996-04-12
申请人： Kyle R. Gee , Martin Poot , Dieter H. Klaubert , Wei-Chuan Sun , Richard P. Haugland , Fei Mao
发明人： Kyle R. Gee , Martin Poot , Dieter H. Klaubert , Wei-Chuan Sun , Richard P. Haugland , Fei Mao
IPC分类号： G01N33/48 , C07B61/00 , C07C37/00 , C07C37/055 , C07C39/27 , C07C205/26 , C07C205/37 , C07C209/36 , C07C213/00 , C07C217/82 , C07C245/20 , C07D311/82 , C07D493/10 , C07F9/6561 , C07K1/13 , C07K16/18 , C09B11/00 , C09B11/24 , C09B11/28 , G01N1/30 , G01N21/76 , C07D311/78 , C07D311/88 , C07D471/00
CPC分类号： C09B11/00 , C07C37/055 , C07C41/18 , C07C201/08 , C07C201/12 , C07C205/26 , C07C205/37 , C07C209/10 , C07C213/02 , C07C213/08 , C07C245/20 , C07D311/82 , C09B11/24 , G01N1/30 , Y10S430/116 , Y10S430/126 , C07C39/245 , C07C211/52 , C07C217/84 , C07C215/76 , C07C43/225
摘要： The family of dyes of the invention are fluoresceins and rhodols that are directly substituted on one or more aromatic carbons by fluorine. These fluorine-substituted fluorescent dyes possess greater photostability and have lower sensitivity to pH changes in the physiological range of 6-8 than do non-fluorinated dyes, exhibit less quenching when conjugated to a substance, and possess additional advantages. The dyes of the invention are useful as detectable tracers and for preparing conjugates of organic and inorganic substances.
摘要翻译：本发明的染料族是在一个或多个芳族碳上被氟直接取代的荧光素和二醇。这些氟取代的荧光染料具有更高的光稳定性，并且对于6-8生理范围内的pH变化的敏感性低于非氟化染料，当与物质缀合时表现出较少的淬灭，并且具有额外的优点。本发明的染料可用作可检测的示踪剂并用于制备有机和无机物质的共轭物。

7. 发明授权

US08323903B2 Antibody complexes and methods for immunolabeling 有权
标题翻译：抗体复合物和免疫标记方法
公开(公告)号：US08323903B2
公开(公告)日：2012-12-04
申请号：US10118204
申请日：2002-04-05
申请人： Robert A. Archer , Joseph M. Beechem , David C. Hagen , Richard P. Haugland , Rosaria P. Haugland
发明人： Robert A. Archer , Joseph M. Beechem , David C. Hagen , Richard P. Haugland , Rosaria P. Haugland
IPC分类号： G01N33/53
CPC分类号： B82Y30/00 , B82Y5/00 , B82Y10/00 , G01N33/53 , G01N33/58 , G01N33/6857
摘要： The present invention provides novel immunolabeling complexes and certain components of such complexes, as well as methods of preparing and using such complexes, and kits for use in preparing labeling proteins and for immunolabeling. The pre-formed immunolabeling complexes of the invention comprise both a target-binding antibody and a labeling protein that contains covalently attached labels, where the labeling protein binds selectively and with high affinity to a selected region of the target-binding antibody. Novel labeling proteins of the invention include non-antibody peptides and proteins, such as a complex of protein G and a labeled albumin, and monovalent antibody fragments, such as labeled Fab fragments of an anti-Fc antibody. In methods of the invention, the preformed immunolabeling complexes are added to the sample alone or in combination, for purposes of labeling and optionally detecting the target of interest.
摘要翻译：本发明提供了新的免疫标记复合物和这些复合物的某些成分，以及制备和使用这些复合物的方法，以及用于制备标记蛋白和免疫标记的试剂盒。本发明的预先形成的免疫粘附复合物包含靶结合抗体和含有共价连接的标记的标记蛋白，其中所述标记蛋白选择性地结合并且与靶结合抗体的选定区域具有高亲和力。本发明的新型标记蛋白包括非抗体肽和蛋白质，例如蛋白G和标记的白蛋白的复合物，以及单价抗体片段，例如抗Fc抗体的标记的Fab片段。在本发明的方法中，为了标记和任选地检测目的靶标，将预先形成的免疫标记复合物单独或组合加入到样品中。

8. 发明授权

US07226740B2 Aza-benzazolium containing cyanine dyes 有权
标题翻译：含有氰基染料的氮杂 -
公开(公告)号：US07226740B2
公开(公告)日：2007-06-05
申请号：US10683753
申请日：2003-10-13
申请人： Richard P. Haugland , Stephen T. Yue
发明人： Richard P. Haugland , Stephen T. Yue
IPC分类号： C12Q1/68 , C07D215/00 , C07D215/12
CPC分类号： C09B23/02 , C12Q1/6816 , C12Q1/6876 , G01N1/30 , G01N27/44726 , G01N33/52 , G01N33/5308 , G01N33/531 , G01N33/582 , G01N33/68 , G01N2001/302 , Y10S436/80 , Y10T436/143333 , C12Q2563/173 , C12Q2563/107
摘要： Unsymmetrical cyanine dyes that incorporate an aza-benzazolium ring moiety are described, including cyanine dyes substituted by a cationic side chain, monomeric and dimeric cyanine dyes, chemically reactive cyanine dyes, and conjugates of cyanine dyes. The subject dyes are virtually non-fluorescent when diluted in aqueous solution, but exhibit bright fluorescence when associated with nucleic acid polymers such as DNA or RNA, or when associated with detergent-complexed proteins. A variety of applications are described for detection and quantitation of nucleic acids and detergent-complexed proteins in a variety of samples, including solutions, electrophoretic gels, cells, and microorganisms.
摘要翻译：描述了包含氮杂 - 苯并唑鎓环部分的不对称花青染料，包括由阳离子侧链取代的花青染料，单体和二聚花青染料，化学反应性花青染料和花青染料的缀合物。当在水溶液中稀释时，受试染料实际上是非荧光的，但当与核酸聚合物如DNA或RNA相关联时或当与洗涤剂复合的蛋白质相关时，它们显示出明亮的荧光。描述了用于检测和定量多种样品中的核酸和洗涤剂复合蛋白质的各种应用，包括溶液，电泳凝胶，细胞和微生物。

9. 发明授权

US06265179B1 Detection of phosphate using coupled enzymatic reactions 有权
标题翻译：使用偶联酶反应检测磷酸盐
公开(公告)号：US06265179B1
公开(公告)日：2001-07-24
申请号：US09495882
申请日：2000-02-01
申请人： Mingjie Zhou , Richard P. Haugland
发明人： Mingjie Zhou , Richard P. Haugland
IPC分类号： C12Q128
CPC分类号： C12Q1/26 , C12Q1/42 , C12Q1/48 , G01N2333/91102 , G01N2333/91142 , G01N2333/916 , Y10S435/968 , Y10S435/975
摘要： Inorganic phosphate may be detected and optionally quantified via the coupling of a phosphate-dependent enzymatic reaction with an enzyme system that generates hydrogen peroxide in the presence of a chromogenic or fluorogenic peroxidase substrate. Phosphate consuming or phosphate-producing enzymes or their substrates may also be detected and/or quantified, including pyrophosphatase enzymes or pyrophosphatase.
摘要翻译：可以通过磷酸盐依赖性酶反应与在显色或荧光过氧化物酶底物存在下产生过氧化氢的酶系统的偶联来检测和任选地定量无机磷酸盐。磷酸盐消耗或磷酸盐生成酶或其底物也可被检测和/或定量，包括焦磷酸酶或焦磷酸酶。

10. 发明授权

US6013802A Fluorescent conjugates of metal-chelating nitrogen heterocycles 失效
标题翻译：金属螯合氮杂环的荧光偶联物
公开(公告)号：US6013802A
公开(公告)日：2000-01-11
申请号：US798390
申请日：1997-02-07
申请人： Brian Matthew Hoyland , Michael A. Kuhn , Richard P. Haugland
发明人： Brian Matthew Hoyland , Michael A. Kuhn , Richard P. Haugland
IPC分类号： C09K11/06 , G01N31/22 , G01N33/84 , C07D401/00
CPC分类号： C09K11/06 , G01N31/22 , G01N33/84 , G01N2800/04
摘要： The present invention describes a family of fluorescent indicators for metal cations. The indicators are fluorophore conjugates of pyridyl-based metal ion chelators. The indicators are very sensitive detection as quantification reagents for a variety of metals, in a variety of oxidation states, even in the presence of high concentrations of Ca.sup.2+, Na.sup.+, or K.sup.+ or other ions, such as is found in seawater, making them highly useful for assaying physiological samples, biological samples, or environmental samples.
摘要翻译：本发明描述了一系列用于金属阳离子的荧光指示剂。指标是吡啶基金属离子螯合剂的荧光团缀合物。这些指标作为各种金属的定量试剂，作为多种氧化态的定量试剂，即使在高浓度的Ca2 +，Na +或K +或其他离子存在下也是非常敏感的，例如在海水中发现，使其高度可用于测定生理样品，生物样品或环境样品。

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