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11. 发明授权

US5316906A Enzymatic analysis using substrates that yield fluorescent precipitates 失效
标题翻译：使用产生荧光沉淀物的底物的酶分析
公开(公告)号：US5316906A
公开(公告)日：1994-05-31
申请号：US748860
申请日：1991-08-23
申请人： Richard P. Haugland , Yu-zhong Zhang , Stephen T. Yue , Ewald Terpetschnig , Nels A. Olson , John J. Naleway , Karen D. Larison , Zhijian Huang
发明人： Richard P. Haugland , Yu-zhong Zhang , Stephen T. Yue , Ewald Terpetschnig , Nels A. Olson , John J. Naleway , Karen D. Larison , Zhijian Huang
IPC分类号： C12Q1/00 , C07D215/14 , C07D235/18 , C07D239/91 , C07D263/56 , C07D263/57 , C07D277/64 , C07D277/66 , C07F9/6512 , C07F9/6541 , C07H15/04 , C07H15/26 , C07K4/00 , C08B37/00 , C12Q1/34 , C12Q1/42 , C12Q1/44 , C12Q1/68 , A61K37/02 , C04B35/00 , C08G63/48
CPC分类号： C07D263/57 , C07D235/18 , C07D239/91 , C07D277/66 , C07F9/65128 , C07F9/6541 , C07H15/26 , C12Q1/34 , C12Q1/42 , C12Q2334/00
摘要： Novel fluorescent precipitating substrates made from a class of fluorophores, generally including quinazolinones (quinazolones), benzimidazoles, benzothiazoles, benzoxazoles, quinolines, indolines, and phenanthridines, having the general formula: ##STR1## where carbon atoms of --C.sup.1 .dbd.C.sup.2 -- are further joined so as to complete a first 5- or 6-membered aromatic ring which may contain at least one of the hetero atoms N, O or S,where carbon atoms of --C.sup.4 --N.dbd.C.sup.3 -- are further joined so as to complete a second 5- or 6-membered aromatic ring that contains at least the nitrogen between C.sup.3 and C.sup.4 and may contain at least one additional hetero atom N, O or S,where the first and second aromatic rings may be joined by a 5- or 6-membered bridging ring that contains at least the C.sup.2 from the first aromatic ring and the C.sup.3 from the second aromatic ring, which bridging ring may be saturated or unsaturated and may contain a hetero atom N, O, or S,where each of the first and second aromatic rings may be fused to at least one additional aromatic ring that may contain at least one of the hetero atoms N, O or S, andwhere each of said aromatic rings may be further modified by substitution of any hydrogens on an aromatic carbon by substituents that are halogen, nitro, cyano, aryl, lower alkyl (1-4 carbons), perfluoroalkyl (1-4 carbons), or alkoxy (1-4 carbons), or any combination thereof; andX.sub.fl is covalently linked to the oxygen --O-- at C.sub.1.
摘要翻译：通常包括喹唑啉酮（喹唑啉酮），苯并咪唑，苯并噻唑，苯并恶唑，喹啉，吲哚啉和菲啶的一类荧光团制备的新型荧光沉淀基质，其具有-C1 = C2-的碳原子的通式为：以便完成可含有至少一个杂原子N，O或S的第一个5-或6-元芳环，其中-C4-N = C3-的碳原子进一步连接，以便完成一个第二个5-或6-元芳环，其至少包含C3和C4之间的氮，并且可以含有至少一个另外的杂原子N，O或S，其中第一和第二芳环可以通过5-或6 至少含有来自第一芳环的C2和来自第二芳环的C3，所述桥连环可以是饱和或不饱和的，并且可以含有杂原子N，O或S，其中第一个并且第二芳环可以稠合 o至少一个可以含有至少一个杂原子N，O或S的另外的芳环，并且其中每个所述芳环可以通过用芳基碳上的任何氢取代而被进一步修饰，所述取代基是卤素，硝基，氰基，芳基，低级烷基（1-4个碳），全氟烷基（1-4个碳）或烷氧基（1-4个碳），或其任何组合; 并且Xfl在C1处与氧-O-共价连接。

12. 发明授权

US5208148A Lipophilic fluorescent glycosidase substrates 失效
标题翻译：亲脂性荧光糖苷酶底物
公开(公告)号：US5208148A
公开(公告)日：1993-05-04
申请号：US623600
申请日：1990-12-07
申请人： Richard P. Haugland , John J. Naleway , Yu-zhong Zhang
发明人： Richard P. Haugland , John J. Naleway , Yu-zhong Zhang
IPC分类号： C07H17/04 , C12Q1/34
CPC分类号： C07H17/04 , C12Q1/34 , C12Q2334/40
摘要： The claimed invention relates to a substrate for evaluating glycosidic enzymes comprising a fluorescein derivative of the general formula: ##STR1## wherein GlyX is a carbohydrate bonded to fluorescein by a glycosidic linkage;Y, which may be the same as GlyX or different, is an alkyl ether, an ester, or a glycosidically linked carbohydrate;R is a lipophilic residue containing from 1 to 21 carbon atoms; andL links the R residue to fluorescein.A preferred embodiment of the invention is a non-fluorescent substrate specifically hydrolyzable by a glycosidase inside a cell to yield, after greater than about 2 minutes, a fluorescent detection product excitable at between about 460 nm and 550 nm and with fluorescence observable at an emission wavelength longer than the excitation wavelength, which fluorescent detection product is retained inside a viable cell more than about 2 hours at greater than about 15.degree. C. and which is non-toxic to the cell. A further embodiment of the invention is a method for evaluating a glycosidic enzyme in living plant or animal cells whether the enzyme is present endogenously; present as a result of manipulation of the cell's genome, or added to the cell exogenously, such as by covalently binding the enzyme to a protein to form an enzyme-protein complex that enters the cell.
摘要翻译：所要求保护的发明涉及用于评估糖苷酶的底物，其包含以下通式的荧光素衍生物：其中GlyX是通过糖苷键与荧光素键合的碳水化合物; 可以与GlyX相同或不同的Y是烷基醚，酯或糖苷连接的碳水化合物; R是含有1至21个碳原子的亲脂性残基; 并且L将R残基连接到荧光素上。本发明的优选实施方案是由细胞内的糖苷酶特异性水解的非荧光底物，大于约2分钟后，可在约460nm至550nm之间激发荧光检测产物，并在发射时可观察到荧光波长比激发波长长，该荧光检测产物在大于约15℃下在活细胞内保留超过约2小时，对细胞无毒性。本发明的另一个实施方案是用于评价活体植物或动物细胞中糖苷酶是否内源性存在的方法; 作为细胞基因组的操作或外源性加入到细胞中的结果，例如通过将酶与蛋白质共价结合以形成进入细胞的酶 - 蛋白质复合物。

13. 发明授权

US5686261A Xanthylium dyes that are well retained in mitochondria 失效
标题翻译：良好保留在线粒体中的Xanthylium染料
公开(公告)号：US5686261A
公开(公告)日：1997-11-11
申请号：US383298
申请日：1995-02-03
申请人： Yu-Zhong Zhang , Richard P. Haugland
发明人： Yu-Zhong Zhang , Richard P. Haugland
IPC分类号： C07D311/82 , C09B11/12 , C12Q1/02 , C12Q1/68
CPC分类号： C09B11/12 , C07D311/82
摘要： The present invention describes a method of staining mitochondria, and analyzing mitochondrial function, using a class of fluorescent substituted 3',6'-diaminoxanthenes and their reduced analogs 3',6'-diaminodihydroxanthenes, which are oxidized to the fluorescent form of the dye in situ. In their oxidized form, the dyes selectively localize within mitochondria. The dyes of the invention are substituted by an alkylating group that allows their retention in mitochondria even after cell death, fixation, and permeabilization.
摘要翻译：本发明描述了使用一类荧光取代的3'，6'-二氨基呫吨及其还原的类似物3'，6'-二氨基二羟基呫吨染色线粒体并分析线粒体功能的方法，其被氧化成染料的荧光形式在原地。在其氧化形式中，染料选择性地定位在线粒体内。本发明的染料被烷基化基团取代，即使在细胞死亡，固定和透化后也能使它们保留在线粒体中。

14. 发明授权

US5242805A Long wavelength lipophilic fluorogenic glycosidase substrates 失效
标题翻译：长波长磷酸荧光蛋白酶底物
公开(公告)号：US5242805A
公开(公告)日：1993-09-07
申请号：US749255
申请日：1991-08-23
申请人： John J. Naleway , Yu-zhong Zhang , Richard P. Haugland
发明人： John J. Naleway , Yu-zhong Zhang , Richard P. Haugland
IPC分类号： C07H17/00 , C12Q1/34
CPC分类号： C12Q1/34 , C07H17/00 , C12Q2334/00 , G01N2333/924
摘要： The claimed invention relates to a substrate for evaluating glycosidic enzymes comprising a resorufin derivative of the general formula: ##STR1## wherein Gly is a carbohydrate bonded to resorufin by a glycosidic linkage; where at least one of substituents R.sub.1, R.sub.2, R.sub.4, R.sub.6, R.sub.8, and R.sub.9 is a lipophilic residue of the formula --L(CH.sub.2).sub.n CH.sub.3, where n is greater than 3 and less than 22, and where L is a methylene --CH.sub.2 --, an amide --NHCO--, a sulfonamide --NHSO.sub.2 --, a carboxamide --CONH--, a carboxylate ester --COO--, a urethane --NHCOO--, a urea --NHCONH--, or a thiourea --NHCSNH--; andwhere the remainder of substituents R.sub.1, R.sub.2, R.sub.4, R.sub.6, R.sub.8, and R.sub.9, which may be the same or different, are hydrogen, halogen, or other lipophilic residues, which may be the same or different, containing from about 1 to about 22 carbon atoms of the formula --L'(CH.sub.2).sub.m CH.sub.3, where m is less than 22, and where L' is a methylene --CH.sub.2 --, an amide --NHCO--, a sulfonamide --NHSO.sub.2 --, a carboxamide --CONH--, a carboxylate ester --COO--, a urethane --NHCOO--, a urea --NHCONH--, or a thiourea --NHCSNH--.A preferred embodiment of the invention is a non-fluorescent substrate specifically hydrolyzable by a glycosidase inside a cell to yield, after greater than about 2 minutes, an orange to red fluorescent detection product which is retained inside a viable cell more than about 2 hours at greater than about 15.degree. C. and which is non-toxic to the cell. The substrates are used for evaluating a glycosidic enzyme in living plant or animal cells whether the enzyme is present endogenously; present as a result of manipulation of the cell's genome, or added to the cell exogenously, such as by covalently binding the enzyme to a protein to form an enzyme-protein complex that enters the cell.
摘要翻译：所要求保护的发明涉及用于评估糖苷酶的底物，其包含通式如下的再生烯衍生物：其中Gly是通过糖苷键键合至残留的碳水化合物; 其中取代基R 1，R 2，R 4，R 6，R 8和R 9中的至少一个是式-L（CH 2）n CH 3的亲脂性残基，其中n大于3且小于22，并且其中L是亚甲基 - CH 2 - ，酰胺-NHCO-，磺酰胺-NHSO 2 - ，酰胺-CONH-，羧酸酯-COO-，氨基甲酸酯-NHCOO-，脲-NHCONH-或硫脲-NHCSNH-; 并且其中可以相同或不同的取代基R 1，R 2，R 4，R 6，R 8和R 9的其余部分是氢，卤素或可以相同或不同的其它亲脂性残基，其含有约1至约22个碳原子的式-L'（CH 2）m CH 3，其中m小于22，其中L'是亚甲基-CH 2 - ，酰胺-NHCO-，磺酰胺-NHSO 2 - ，甲酰胺-CONH- ，羧酸酯-COO-，氨基甲酸酯-NHCOO-，脲-NHCONH-或硫脲-NHCSNH-。本发明的优选实施方案是特异性可由细胞内的糖苷酶水解的非荧光底物，大于约2分钟后，产生橙色至红色荧光检测产物，其在活细胞内保留超过约2小时大于约15℃，对细胞无毒性。底物用于评价活体植物或动物细胞中的糖苷酶，无论酶是否内源性存在; 作为细胞基因组的操作或外源性加入到细胞中的结果，例如通过将酶与蛋白质共价结合以形成进入细胞的酶 - 蛋白质复合物。

15. 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。

16. 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。

17. 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。

18. 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。

19. 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。

20. 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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