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61. 发明授权

US4774339A Chemically reactive dipyrrometheneboron difluoride dyes 失效
标题翻译：化学反应性二吡咯亚甲基二氟化物染料
公开(公告)号：US4774339A
公开(公告)日：1988-09-27
申请号：US83458
申请日：1987-08-10
申请人： Richard P. Haugland , Hee C. Kang
发明人： Richard P. Haugland , Hee C. Kang
IPC分类号： C07F5/02 , G01N33/58 , C07D209/00 , C07D209/56
CPC分类号： C07F5/022 , G01N33/582
摘要： Novel fluorescent dyes based on the dipyrrometheneboron difluoride structure are provided. The new reagents contain functional groups capable of forming a stable fluorescent product with functional groups typically found in biomolecules or polymers including amines, phenols, thiols, acids, aldehydes and ketones. Reactive groups in the dipyrrometheneboron difluoride dyes include activated esters, isocyanates, amines, hydrazines, sulfonyl halides, acids, aldehydes, alcohols and haloacetamides. The products are detected by their absorbance or fluorescence properties. The spectral properties of the fluorescent dyes are sufficiently similar in wavelengths and intensity to fluorescein as to permit use of the same euqipment. The dyes, however, have narrower spectral bandwidths than fluorescein, do not show appreciable sensitivity to pH, have higher solubility in non-polar solvents and have improved photostability.
摘要翻译：提供了基于二吡咯亚甲基二氟化物结构的新型荧光染料。新试剂含有能够形成稳定荧光产物的官能团，其具有通常在生物分子或聚合物中发现的官能团，包括胺，酚，硫醇，酸，醛和酮。二吡咯甲烷二氟化物染料中的活性基团包括活性酯，异氰酸酯，胺，肼，磺酰卤，酸，醛，醇和卤代乙酰胺。通过其吸光度或荧光特性检测产物。荧光染料的光谱性质在荧光素的波长和强度上足够相似，以允许使用相同的设备。然而，染料具有比荧光素更窄的光谱带宽，不显示对pH的明显敏感性，在非极性溶剂中具有更高的溶解度并具有改善的光稳定性。

62. 发明申请

US20130072666A1 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：US20130072666A1
公开(公告)日：2013-03-21
申请号：US13610009
申请日：2012-09-11
申请人： Robert M. Archer , Joseph M. Beechem , David C. Hagen , Richard P. Haugland , Rosaria P. Haugland
发明人： Robert M. Archer , Joseph M. Beechem , David C. Hagen , Richard P. Haugland , Rosaria P. Haugland
IPC分类号： C07K1/113 , C07K16/00 , C12P21/06
CPC分类号： B82Y5/00 , B82Y10/00 , G01N33/53
摘要： Provided are labeling reagents and methods for labeling primary antibodies and for detecting a target in a sample using an immuno-labeled complex that comprises a target-binding antibody and one or more labeling reagents. The labeling reagents comprise monovalent antibody fragments or non-antibody monomeric proteins whereby the labeling proteins have affinity for a specific region of the target-binding antibody and are covalently attached to a label. Discrete subsets of labeling reagent and immune-labeled complexes are provided that facilitate the simultaneous detection of multiple targets in a sample-complexes are distinguished by i) a ratio of label to labeling reagent, or ii) a physical property of said label, or iii) a ratio of labeling reagent to said target-binding antibody, or iv) by said target-binding antibody. This is particularly useful for fluorophore labels that can be attached to labeling reagents and subsequently immuno-labeled complexes in ratios for the detection of multiple targets.
摘要翻译：提供标记试剂和用于标记一抗的标记试剂和用于使用包含靶结合抗体和一种或多种标记试剂的免疫标记复合物检测样品中的靶标的方法。标记试剂包括单价抗体片段或非抗体单体蛋白质，由此标记的蛋白质对靶标结合抗体的特定区域具有亲和力，并且共价连接到标记物上。提供标记试剂和免疫标记复合物的离散子集，其有利于同时检测样品中多个靶标的复合物，其特征在于i）标记与标记试剂的比例，或ii）所述标记的物理性质，或iii ）标记试剂与所述靶结合抗体的比例，或iv）所述靶结合抗体。这对于可以连接到标记试剂和随后的用于检测多个靶的比例的免疫标记的复合物的荧光团标记物特别有用。

63. 发明申请

US20090124511A1 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：US20090124511A1
公开(公告)日：2009-05-14
申请号：US12047131
申请日：2008-03-12
申请人： Robert M. Archer , Joseph M. Beechem , David C. Hagen , Richard P. Haugland , Rosaria P. Haugland
发明人： Robert M. Archer , Joseph M. Beechem , David C. Hagen , Richard P. Haugland , Rosaria P. Haugland
IPC分类号： C40B30/04 , C07K1/13 , C40B50/00 , C12N9/00 , C12N9/08 , C12N9/02 , C40B50/08 , C40B40/10 , C07K16/00 , C12P21/06 , C12N9/16 , C12N9/24 , G01N33/567 , G01N33/543
CPC分类号： B82Y5/00 , B82Y10/00 , G01N33/53
摘要： The present invention provides labeling reagents and methods for labeling primary antibodies and for detecting a target in a sample using an immuno-labeled complex that comprises a target-binding antibody and one or more labeling reagents. The labeling reagents comprise monovalent antibody fragments or non-antibody monomeric proteins whereby the labeling proteins have affinity for a specific region of the target-binding antibody and are covalently attached to a label. Typically, the labeling reagent is an anti-Fc Fab or Fab′ fragment that was generated by immunizing a goat or rabbit with the Fc fragment of an antibody. The present invention provides for discrete subsets of labeling reagent and immuno-labeled complexes that facilitate the simultaneous detection of multiple targets in a sample wherein the immuno-labeled complexes are distinguished by i) a ratio of label to labeling reagent, or ii) a physical property of said label, or iii) a ratio of labeling reagent to said target-binding antibody, or iv) by said target-binding antibody. This is particularly useful for fluorophore labels that can be attached to labeling reagents and subsequently immuno-labeled complexes in ratios for the detection of multiple targets.
摘要翻译：本发明提供标记试剂和用于标记一抗的标记试剂和使用包含靶结合抗体和一种或多种标记试剂的免疫标记复合物检测样品中靶标的方法。标记试剂包括单价抗体片段或非抗体单体蛋白质，由此标记的蛋白质对靶标结合抗体的特定区域具有亲和力，并且共价连接到标记物上。通常，标记试剂是通过用抗体的Fc片段免疫山羊或兔而产生的抗Fc Fab或Fab'片段。本发明提供标记试剂和免疫标记的复合物的离散子集，其有助于同时检测样品中的多个靶标，其中通过i）标记物与标记试剂的比率来区分免疫标记的复合物，或ii）物理或iii）标记试剂与所述靶结合抗体的比例，或iv）所述靶结合抗体。这对于可以连接到标记试剂和随后的用于检测多个靶的比例的免疫标记的复合物的荧光团标记物特别有用。

64. 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.

65. 发明授权

US06562632B1 Reactive derivatives of sulforhodamine 101 with enhanced hydrolytic stability 有权
标题翻译：具有增强的水解稳定性的磺酰罗丹胺101的活性衍生物
公开(公告)号：US06562632B1
公开(公告)日：2003-05-13
申请号：US09129015
申请日：1998-08-04
申请人： Wojciech Szalecki , Richard P. Haugland
发明人： Wojciech Szalecki , Richard P. Haugland
IPC分类号： G01N33533
CPC分类号： C07H19/10 , C07H21/00 , C07K7/06 , C07K14/36 , C07K14/765 , C07K16/4283 , C08B37/0021 , C09B11/24 , C09B62/002 , Y10S436/80
摘要： The invention describes reactive dyes having an alkyl spacer attached via a sulfonamide bond to a sulforhodamine 101 fluorophore, and a variety of useful conjugates prepared therefrom. The increased length of the covalent linkage due to the alkyl spacer results in dye-conjugates having a number of surprisingly advantageous properties relative to previous sulforhodamine 101-labeled conjugates, including enhanced solubility and increased fluorescence. The reactive dyes of the present invention are more stable than the known compound sulforhodamine 101 sulfonyl chloride. Novel reactive dyes are described for selective modification of groups other than amines, including thiols and photoreactive derivatives.
摘要翻译：本发明描述了具有通过磺酰胺键与硫代罗丹明101荧光团连接的烷基间隔基的活性染料和由其制备的各种有用的缀合物。由于烷基间隔物引起的共价连接的长度增加导致染料缀合物相对于先前的磺酰罗丹明101标记的缀合物具有许多令人惊奇的有利性质，包括增强的溶解度和增加的荧光。本发明的活性染料比已知的化合物磺酰罗丹胺101磺酰氯更稳定。描述了新型活性染料用于选择性改性除胺以外的基团，包括硫醇和光反应性衍生物。

66. 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。

67. 发明授权

US5786219A Microspheres with fluorescent spherical zones 失效
标题翻译：具有荧光球形区域的微球
公开(公告)号：US5786219A
公开(公告)日：1998-07-28
申请号：US740184
申请日：1996-10-28
申请人： Yu-Zhong Zhang , Courtenay R. Kemper , Richard P. Haugland
发明人： Yu-Zhong Zhang , Courtenay R. Kemper , Richard P. Haugland
IPC分类号： G01N15/10 , G01N33/58 , G01Q60/18 , G01N33/546 , G01N33/533
CPC分类号： G01N15/1012 , G01N33/585 , Y10T428/2982 , Y10T428/2989 , Y10T428/2991 , Y10T428/2998
摘要： The invention describes novel fluorescently labeled microspheres, where the microspheres possess at least one internal fluorescent spherical zone. The invention also describes the method of preparing the novel microspheres, the method of calibrating microscopy instrumentation using the novel microspheres, the method of using the novel microspheres as distinct labels for combinatorial analysis and the use of the labeled microspheres as tagging agents and tracers.
摘要翻译：本发明描述了新颖的荧光标记微球，其中微球体具有至少一个内部荧光球形区域。本发明还描述了制备新型微球的方法，使用新型微球校准显微镜仪器的方法，使用新型微球作为组合分析的不同标签的方法，以及使用标记的微球作标记剂和示踪剂。

68. 发明授权

US5723218A Dipyrrometheneboron difluoride labeled flourescent microparticles 失效
标题翻译：二吡咯甲烷二氟化物标记的荧光微粒
公开(公告)号：US5723218A
公开(公告)日：1998-03-03
申请号：US484151
申请日：1995-06-07
申请人： Richard P. Haugland , Rosaria P. Haugland , John Michael Brinkley , Hee Chol Kang , Michael Kuhn , K. Sam Wells , Yu Zhong Zhang
发明人： Richard P. Haugland , Rosaria P. Haugland , John Michael Brinkley , Hee Chol Kang , Michael Kuhn , K. Sam Wells , Yu Zhong Zhang
IPC分类号： C09K11/06 , G01N33/533 , B32B27/18
CPC分类号： G01N33/533 , C09K11/06 , Y10T428/2982 , Y10T428/2991 , Y10T428/2998
摘要： The invention is a novel fluorescently labeled microparticle, where the microparticle internally incorporates at least one dipyrrometheneboron difluoride dye. Appropriate selection of substituents results in dipyrrometheneboron difluoride derivatives that, when incorporated into polymer microparticles, give the desired excitation and emission wavelengths. The spectral characteristics of the labeling dyes in liquid are not greatly changed when the dye is incorporated into the particles, and the spectral excitation and emission wavelengths are compatible with commonly used filter sets. Other embodiments of the fluorescent microparticles include additional dyes and/or bioreactive substances.
摘要翻译：本发明是一种新型荧光标记微粒，其中微粒内部掺入至少一种二吡咯亚甲基二氟化物染料。取代基的适当选择导致二吡咯亚甲基二氟化物衍生物，当掺入聚合物微粒中时，得到期望的激发和发射波长。当染料掺入颗粒中时，液体中标记染料的光谱特性没有大的变化，光谱激发和发射波长与通常使用的滤光片组兼容。荧光微粒的其它实施方案包括另外的染料和/或生物反应性物质。

69. 发明授权

US5719031A Dye labeled polymers as reagents for measuring polymer degradation 失效
标题翻译：染料标记的聚合物作为测量聚合物降解的试剂
公开(公告)号：US5719031A
公开(公告)日：1998-02-17
申请号：US696544
申请日：1996-08-14
申请人： Richard P. Haugland , Mingjie Zhou
发明人： Richard P. Haugland , Mingjie Zhou
IPC分类号： G01N33/533 , G01N33/58 , G01N33/573 , C07K17/00 , G01N33/68
CPC分类号： G01N33/582 , G01N33/533 , Y10S530/81 , Y10S530/813 , Y10S530/814
摘要： This invention relates to polymers labeled with fluorescent dye to the point that significant fluorescence quenching occurs, such that degradation of the polymer results in fluorescence enhancement. The resulting fluorescence enhancement is useful for measuring the degradation of such polymers, for example as a result of enzymatic hydrolyis of a protein, carbohydrate, nucleic acid, or other natural or synthetic polymer.
摘要翻译：本发明涉及用荧光染料标记的聚合物，使得发生显着的荧光猝灭，使得聚合物的降解导致荧光增强。所得到的荧光增强可用于测量这种聚合物的降解，例如由于蛋白质，碳水化合物，核酸或其它天然或合成聚合物的酶促水解。

70. 发明授权

US5442045A Biological conjugates of fluorescent rhodol dyes 失效
标题翻译：荧光色罗兰染料的生物共轭物
公开(公告)号：US5442045A
公开(公告)日：1995-08-15
申请号：US28319
申请日：1993-03-08
申请人： Richard P. Haugland , James E. Whitaker
发明人： Richard P. Haugland , James E. Whitaker
IPC分类号： C07D311/82 , C07D491/14 , C07D491/22 , C09B11/10 , C09K11/06 , G01N37/00 , C07D211/00 , C07K1/13
CPC分类号： C07D491/14 , C07D311/82 , C09B11/10 , C09K11/06
摘要： Novel fluorescent dyes based on the rhodol structure are provided. The new reagents contain functional groups capable of forming a stable fluorescent product with functional groups typically found in biomolecules or polymers including amines, phenols, thiols, acids, aldehydes and ketones. Reactive groups in the rhodol dyes include activated esters, isothiocyanates, amines, hydrazines, halides, acids, azides, maleimides, aldehydes, alcohols, acrylamides and haloacetamides. The products are detected by their absorbance or fluorescence properties. The spectral properties of the fluorescent dyes are sufficiently similar in wavelengths and intensity to fluorescein or rhodamine derivatives as to permit use of the same equipment. The dyes, however, show less spectral sensitivity to pH in the physiological range than does fluorescein, have higher solubility in non-polar solvents and have improved photostability and quantum yields.
摘要翻译：提供了基于rhodol结构的新型荧光染料。新试剂含有能够形成稳定荧光产物的官能团，其具有通常在生物分子或聚合物中发现的官能团，包括胺，酚，硫醇，酸，醛和酮。罗丹明染料中的活性基团包括活性酯，异硫氰酸酯，胺，肼，卤化物，酸，叠氮化物，马来酰亚胺，醛，醇，丙烯酰胺和卤代乙酰胺。通过其吸光度或荧光特性检测产物。荧光染料的光谱性质在波长和强度上与荧光素或罗丹明衍生物足够相似，以允许使用相同的设备。然而，染料在生理范围内对荧光素的pH值的敏感性较低，在非极性溶剂中具有较高的溶解度，并具有改善的光稳定性和量子产率。

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