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41. 发明授权

US5830912A Derivatives of 6,8-difluoro-7-hydroxycoumarin 失效
标题翻译： 6,8-二氟-7-羟基香豆素的衍生物
公开(公告)号：US5830912A
公开(公告)日：1998-11-03
申请号：US749684
申请日：1996-11-15
申请人： Kyle R. Gee , Richard P. Haugland , Wei-Chuan Sun
发明人： Kyle R. Gee , Richard P. Haugland , Wei-Chuan Sun
IPC分类号： C07D311/16 , C07D311/54 , C07F9/655 , C09B57/02 , A61K31/37 , C07D311/14
CPC分类号： C07D311/16 , C07D311/54 , C07F9/65522 , C09B57/02
摘要： The present invention comprises 6,8-difluoro-7-hydroxycoumarins and derivatives of 6,8-difluoro-7-hydroxycoumarins, including reactive dyes, dye-conjugates and enzyme substrates. These fluorine-substituted fluorescent dyes typically possess greater photostability and lower pH sensitivity in the physiological pH range than their nonfluorinated analogs, exhibit less fluorescence quenching when conjugated to a substance, possess absorption and emission spectra that closely match those of their nonfluorinated analogs, and also exhibit higher quantum yields than their nonfluorinated analogs.
摘要翻译：本发明包括6,8-二氟-7-羟基香豆素和6,8-二氟-7-羟基香豆素的衍生物，包括活性染料，染料共轭物和酶底物。这些氟取代的荧光染料通常在生理pH范围内比其非氟化类似物具有更高的光稳定性和较低的pH敏感性，当与物质缀合时显示较少的荧光猝灭，具有与其非氟化类似物的吸收和发射光谱非常接近的吸收和发射光谱，以及表现出比其非氟化类似物更高的量子产率。

42. 发明授权

US5516864A Fluorescent ion-selective diaryldiaza crown ether conjugates 失效
公开(公告)号：US5516864A
公开(公告)日：1996-05-14
申请号：US375360
申请日：1995-01-19
申请人： Michael A. Kuhn , Richard P. Haugland
发明人： Michael A. Kuhn , Richard P. Haugland
IPC分类号： C07D273/00 , C07D273/08 , C09K11/06 , G01N31/22 , G01N33/84 , C07D321/00 , C08F26/08
CPC分类号： C07D273/00 , C09K11/06 , G01N31/22 , G01N33/84
摘要： This invention describes novel sensors for ions that are based on the combination of xanthylium-based dyes with metal-binding N,N'-diaryldiaza crown ethers. These sensors are primarily useful for detection and quantitation of alkali-metal ions in aqueous solution. Binding of the ion results in a change in the fluorescence properties of the indicating dye that can be correlated with the ion concentration. Methods are provided for attaching reactive groups on these sensors for conjugation to dyes, lipids and polymers and for enhancing entry of the indicators into living cells.

43. 发明授权

US5514710A Photocleavable derivatives of hydroxyprenesulfonic acids 失效
标题翻译：羟基磺酸的可透光衍生物
公开(公告)号：US5514710A
公开(公告)日：1996-05-07
申请号：US180543
申请日：1994-01-11
申请人： Richard P. Haugland , Kyle R. Gee
发明人： Richard P. Haugland , Kyle R. Gee
IPC分类号： C07C309/43 , A61K31/265 , A61K31/185 , C07C69/96 , C07C309/38
CPC分类号： C07C309/43
摘要： The invention describes the synthesis and use of photoactivated (or caged) fluorescent dyes. Upon illumination at less than about 400 nm the caged dyes release highly fluorescent, water soluble hydroxypyrenesulfonic acid dyes according to the following equation: ##STR1## X, Y, and Z are independently sulfonic acid, a sulfonic acid salt, a hydroxyl group, or hydrogen, with at least one of X, Y, and Z being a sulfonic acid or sulfonic acid salt. LINK is either an ether linkage or a carbonate linkage. BLOCK is a caging group whose photolysis results in liberation of a free hydroxypyrenesulfonic acid dye.The caged fluorescent dyes are useful for application in aqueous solutions, including fluids of biological origin. The caged dyes of the present invention are especially useful for flow tagging velocimetry.
摘要翻译：本发明描述了光活化（或笼式）荧光染料的合成和应用。在小于约400nm的照射下，笼状染料根据以下等式释放高度荧光的水溶性羟基苯磺酸染料：X，Y和Z独立地为磺酸，磺酸盐，羟基或氢，X，Y和Z中的至少一个为磺酸或磺酸盐。 LINK是醚键或碳酸酯键。 BLOCK是一种闭孔组，其光解导致游离羟基苯磺酸染料的释放。笼式荧光染料可用于水溶液，包括生物来源的流体。本发明的笼状染料特别适用于流动标签测速。

44. 发明授权

US5410030A Dimers of unsymmetrical cyanine dyes containing pyridinium moieties 失效
标题翻译：含有吡啶鎓部分的不对称花青染料的二聚体
公开(公告)号：US5410030A
公开(公告)日：1995-04-25
申请号：US43665
申请日：1993-04-05
申请人： Stephen T. Yue , Richard P. Haugland
发明人： Stephen T. Yue , Richard P. Haugland
IPC分类号： C09B23/02 , C07H21/02 , C07H21/04
CPC分类号： C09B23/02
摘要： The invention relates to nucleic acid stains that are homo- or heterodimers of unsymmetrical cyanine dyes, where at least one dye unit of the dimer is a substituted or unsubstituted benzazolium- or naphthazolium-pyridinium derivative, which dye unit is linked to another unsymmetrical cyanine dye unit, that is the same or different by an aliphatic chain containing one or more heteroatoms; such that the fluorescence of the dye molecules, when bound to nucleic acids, is enhanced. These dimers of unsymmetrical cyanine dyes have spectral properties and binding affinities superior to related monomers. In addition, the dyes can be tailored to absorb and emit in a wide range of wavelengths, which can be further varied by energy transfer mixtures, making the dyes useful for applications that involve simultaneous use of multiple dyes.
摘要翻译：本发明涉及作为不对称花青染料的同二聚体或异二聚体的核酸染色，其中二聚体的至少一个染料单元是取代或未取代的苯并唑鎓或萘并吡唑鎓 - 吡啶鎓衍生物，该染料单元与另一不对称花青染料单元，由含有一个或多个杂原子的脂族链相同或不同; 使得当与核酸结合时染料分子的荧光增强。这些不对称花青染料的二聚体具有优于相关单体的光谱性质和结合亲和力。此外，染料可以被定制为在宽范围的波长下吸收和发射，这可以通过能量转移混合物进一步变化，使得染料可用于涉及同时使用多种染料的应用。

45. 发明授权

US4855225A Method of detecting electrophoretically separated oligonucleotides 失效
标题翻译：检测电泳分离的寡核苷酸的方法
公开(公告)号：US4855225A
公开(公告)日：1989-08-08
申请号：US827348
申请日：1986-02-07
申请人： Steven Fung , Sam L. Woo , Richard P. Haugland , Steven M. Menchen , Charles R. Connell
发明人： Steven Fung , Sam L. Woo , Richard P. Haugland , Steven M. Menchen , Charles R. Connell
IPC分类号： C07H21/04 , C07H1/06 , C07H21/00 , C12Q1/68 , G01N27/26 , G01N27/447 , G01N33/50 , G01N33/58
CPC分类号： G01N33/582 , C07H21/00 , C12Q1/6816 , C12Q1/6874
摘要： A method is provided for detecting up to four classes of oligonucleotides which have been separated by gel electrophoresis. The method entails labeling members of each class of oligonucleotide with dyes selected from separate sets of dyes so that members of the same class are labeled with dyes from the same set. The four sets of dyes of the invention consist of derivatives of fluorescein, 2',7'-dimethoxy-4', 5'-dichlorofluorescein, tetramethylrhodamine, and rhodamine X carboxylic or sulfonic acid, respectively. Dyes from these sets are spectrally resolvable under conditions of gel electrophoresis.
摘要翻译：提供了一种用于检测多达四类通过凝胶电泳分离的寡核苷酸的方法。该方法需要用选自单独的染料组的染料标记每一类寡核苷酸的成员，使得同一类的成员用来自同一组的染料标记。本发明的四组染料分别由荧光素，2'，7'-二甲氧基-4'，5'-二氯荧光素，四甲基罗丹明和罗丹明X羧酸或磺酸的衍生物组成。来自这些组的染料在凝胶电泳条件下是光谱可分辨的。

46. 发明授权

US06972326B2 Labeling of immobilized proteins using dipyrrometheneboron difluoride dyes 有权
标题翻译：使用二吡咯亚甲基二氟化物染料标记固定化蛋白质
公开(公告)号：US06972326B2
公开(公告)日：2005-12-06
申请号：US10005050
申请日：2001-12-03
申请人： Richard P. Haugland , Karen J. Martin , Wayne F. Patton
发明人： Richard P. Haugland , Karen J. Martin , Wayne F. Patton
IPC分类号： C07F5/02 , C07K1/107 , C07K1/13 , C07K14/47 , C07K16/46 , C07K17/06 , G01N21/76 , G01N27/447 , G01N33/00 , G01N33/53 , G01N33/533 , G01N33/537 , G01N33/543 , G01N33/58 , G01N33/68
CPC分类号： G01N33/54306 , C07K1/1077 , C07K1/13 , G01N27/44726 , G01N33/581 , G01N33/583 , G01N33/6839
摘要： The invention describes methods for labeling or detecting of immobilized poly(amino acids), including peptides, polypeptides and proteins, on membranes and other solid supports, using fluorescent dipyrrometheneboron difluoride dyes. Such immobilized poly(amino acids) are labeled or detected on blots or on arrays of poly(amino acids), or are attached to immobilized aptamers.
摘要翻译：本发明描述了使用荧光二吡咯亚甲基二氟化物染料在膜和其它固体支持物上标记或检测固定的聚（氨基酸），包括肽，多肽和蛋白质的方法。这种固定的聚（氨基酸）在印迹或聚（氨基酸）阵列上被标记或检测，或连接到固定的适体。

47. 发明授权

US06664047B1 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：US06664047B1
公开(公告)日：2003-12-16
申请号：US09557275
申请日：2000-04-24
申请人： Richard P. Haugland , Stephen T. Yue
发明人： Richard P. Haugland , Stephen T. Yue
IPC分类号： C12Q168
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。

48. 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。

49. 发明授权

US5773236A Assay for glutathiane transferase using polyhaloaryl-substituted reporter molecules 失效
标题翻译：用于酶测定的多卤代芳基取代的报道分子
公开(公告)号：US5773236A
公开(公告)日：1998-06-30
申请号：US845301
申请日：1997-04-25
申请人： Zhenjun Diwu , Richard P. Haugland
发明人： Zhenjun Diwu , Richard P. Haugland
IPC分类号： C07C233/65 , C07C233/78 , C07D265/38 , C07D295/192 , C07D311/16 , C07D311/88 , C07D493/10 , C07F9/655 , C07F9/6561 , C07K5/02 , A61K38/06 , C07D311/82
CPC分类号： C07D295/192 , C07C233/65 , C07C233/78 , C07D265/38 , C07D311/16 , C07D311/88 , C07D493/10 , C07F9/65522 , C07F9/6561 , C07K5/0215
摘要： The subject invention describes compounds containing a polyhalogenated aryl moiety. The compounds of the invention are particularly useful for the assay of a variety of enzymes, including intracellular enzymes. The subject invention also describes assays for glutathione and/or glutathione transferase enzymes. Selected compounds of the invention are particularly useful for improving the retention of fluorescent products of enzyme metabolism in cells.
摘要翻译：本发明描述了含有多卤代芳基部分的化合物。本发明的化合物特别可用于各种酶的测定，包括细胞内酶。本发明还描述了对谷胱甘肽和/或谷胱甘肽转移酶的测定。本发明的选择的化合物特别可用于改善细胞中酶代谢的荧光产物的保留。

50. 发明授权

US5648270A Methods of sensing with fluorescent conjugates of metal-chelating nitrogen heterocycles 失效
标题翻译：用金属螯合氮杂环的荧光共轭物感测的方法
公开(公告)号：US5648270A
公开(公告)日：1997-07-15
申请号：US384945
申请日：1995-02-06
申请人： Michael A. Kuhn , Richard P. Haugland , Brian Matthew Hoyland
发明人： Michael A. Kuhn , Richard P. Haugland , Brian Matthew Hoyland
IPC分类号： C09K11/06 , G01N31/22 , G01N33/84 , G01N33/20
CPC分类号： C09K11/06 , G01N31/22 , G01N33/84 , G01N2800/04
摘要： The present invention describes the use of 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的用途。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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