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1. 发明授权

US5658751A Substituted unsymmetrical cyanine dyes with selected permeability 失效
标题翻译：取代的不对称花青染料具有选择的渗透性
公开(公告)号：US5658751A
公开(公告)日：1997-08-19
申请号：US331031
申请日：1994-10-27
申请人： Stephen T. Yue , Victoria L. Singer , Bruce L. Roth , Thomas J. Mozer , Paul J. Millard , Laurie J. Jones , Xiaokui Jin , Richard P. Haugland
发明人： Stephen T. Yue , Victoria L. Singer , Bruce L. Roth , Thomas J. Mozer , Paul J. Millard , Laurie J. Jones , Xiaokui Jin , Richard P. Haugland
IPC分类号： G01N33/48 , C07D215/18 , C07D413/06 , C07D417/06 , C07D417/14 , C09B23/00 , C09B23/02 , C12Q1/68 , G01N21/76 , G01N33/58 , C12Q1/04 , C07H19/20 , C12Q1/02 , G01N33/00
CPC分类号： C07D417/14 , C07D215/18 , C07D413/06 , C07D417/06 , C09B23/02 , C12Q1/6816 , G01N15/1459 , G01N2015/1402 , Y10S436/80 , Y10T436/143333
摘要： The invention describes the preparation and use of fluorescent stains for nucleic acids derived from unsymmetrical cyanine dyes comprising a substituted benzazolium ring system linked by a methine bridge to a pyridinium or quinolinium ring system having at least one substituent on the pyridinium or quinolinium ring that contains a heteroatom. The presence of the heteroatom-containing substituent results in higher sensitivity to oligonucleotides and larger nucleic acid polymers in a wide range of cells and gels, and for use in analysis of cell structure, membrane integrity or function.
摘要翻译：本发明描述了衍生自不对称花青染料的核酸的荧光染料的制备和用途，其包含通过次甲基桥连接到吡啶鎓或喹啉鎓环系统的取代的苯并唑鎓环系统，所述吡啶鎓或喹啉环体系在吡啶鎓或喹啉环上具有至少一个取代基，杂原子。含杂原子的取代基的存在导致在宽范围的细胞和凝胶中对寡核苷酸和较大核酸聚合物的更高的敏感性，并且用于分析细胞结构，膜完整性或功能。

2. 发明授权

US5545535A Fluorescent assay for bacterial gram reaction 失效
标题翻译：荧光测定细菌克反应
公开(公告)号：US5545535A
公开(公告)日：1996-08-13
申请号：US146328
申请日：1993-11-01
申请人： Bruce L. Roth , Paul J. Millard , Stephen T. Yue , K. Sam Wells , Richard P. Haugland
发明人： Bruce L. Roth , Paul J. Millard , Stephen T. Yue , K. Sam Wells , Richard P. Haugland
IPC分类号： C07D211/76 , C07D215/18 , C07D215/22 , C07D215/227 , C07D417/06 , C07D417/14 , C09B23/02 , C12Q1/04 , C07H1/00 , C12Q1/68 , G01N33/00
CPC分类号： C07D215/227 , C07D211/76 , C07D215/18 , C07D417/06 , C07D417/14 , C09B23/02 , Y10S436/80 , Y10T436/143333
摘要： The invention relates to a method of analyzing a sample thought to contain bacteria using an aqueous solution comprising one or more fluorescent dyes: a fluorescent dye of formula I, a fluorescent dye of formula II, a fluorescent dye of formula III, and a fluorescent dye of formula IV. Each of the dyes differ each from the other in their affinity for nucleic acids and in their spectral response to different types of bacteria in the sample. The first three dyes are nucleic acid stains and the fourth dye is a fluorescent reagent that binds selectively to cell surface components. The fluorescent dyes of formula I are highly membrane-permeant cyanine dye derivatives and label all bacteria, whether live or dead, whether Gram positive or Gram negative. The dyes of formula II label only live Gram positive bacteria and label all dead bacteria, whether Gram positive or negative. The dyes of formula II bind to nucleic acids preferentially with respect to the dyes of formula I. Fluorescent formula III dyes are membrane impermeant dyes that give a fluorescent signal only in cells with compromised plasma membrane integrity, whether Gram negative or Gram positive, and have a much higher binding affinity for nucleic acids than the fluorescent dyes of either formula I or formula II. Formula IV fluorescent dyes preferentially bind to an exterior component of a bacterium. The dyes are combined with a sample suspected of containing bacteria and illuminated at an appropriate wavelength to differentiate, according to the fluorescence response, live Gram negative, dead Gram negative, live Gram positive and dead Gram positive bacteria in the sample.
摘要翻译：本发明涉及使用包含一种或多种荧光染料的水溶液分析包含细菌的样品的方法：式I的荧光染料，式II的荧光染料，式III的荧光染料和荧光染料的式IV。每种染料在其对核酸的亲和力和对样品中不同类型的细菌的光谱响应方面各自不同。前三种染料是核酸污渍，第四种染料是与细胞表面组分有选择性结合的荧光试剂。式I的荧光染料是高度透膜的花青染料衍生物，并标记所有细菌，无论是活还是死，无论革兰氏阳性或革兰氏阴性。式II的染料仅标记活的革兰氏阳性细菌，并标记所有死亡细菌，无论是革兰氏阳性还是阴性。式II的染料优选结合式I的染料。荧光剂III染料是仅在具有损伤的质膜完整性的细胞中产生荧光信号的膜不透明染料，无论是革兰氏阴性还是革兰氏阳性，并具有与核酸的结合亲和力高于式I或式II的荧光染料。式IV荧光染料优先结合细菌的外部组分。染料与怀疑含有细菌的样品结合，并以适当的波长照射，以根据荧光响应分辨样品中的活革兰氏阴性，死革兰氏阴性，活的革兰氏阳性和死的革兰氏阳性细菌。

3. 发明授权

US5534416A Fluorescent viability assay using cyclic-substituted unsymmetrical cyanine dyes 失效
公开(公告)号：US5534416A
公开(公告)日：1996-07-09
申请号：US148847
申请日：1993-11-08
申请人： Paul J. Millard , Bruce L. Roth , Stephen T. Yue , Richard P. Haugland
发明人： Paul J. Millard , Bruce L. Roth , Stephen T. Yue , Richard P. Haugland
IPC分类号： C07D215/22 , C07D211/76 , C07D213/60 , C07D213/61 , C07D213/64 , C07D215/16 , C07D215/18 , C07D215/227 , C07D277/64 , C07D413/06 , C07D417/06 , C07D417/14 , C09B23/00 , C09B23/02 , C09B23/04 , C09B69/06 , C12Q1/68 , G01N21/64 , G01N21/78 , G01N27/26 , G01N31/22 , G01N33/48 , G01N33/50 , G01N33/52 , G01N33/58 , G01N33/00 , C07H1/00 , C12Q1/04
CPC分类号： C07D211/76 , C07D215/18 , C07D215/227 , C07D417/06 , C07D417/14 , C09B23/02 , Y10S436/80 , Y10T436/143333
摘要： The invention relates to a method of analyzing the viability of a sample of cells using an aqueous solution comprising two fluorescent dyes. Dye I has the formula: ##STR1## where R.sup.2 is C.sub.1-6 alkyl; Z.sup.- is a biologically compatible counterion;X is O; S; Se; or NR.sup.15, where R.sup.15 is H or C.sub.1-6 alkyl; or CR.sup.16 R.sup.17, where R.sup.16 and R.sup.17, which may be the same or different, are independently H or C.sub.1-6 alkyl, or the carbons of R.sup.16 and R.sup.17 taken in combination complete a five or six membered saturated ring; and the benzazolium is optionally further substituted;n=0, 1, or 2;Y is --CR.sup.3 .dbd.CR.sup.4 --; p and m=0 or 1, such that p+m=1;R.sup.5 is a C.sub.1-6 alkyl, C.sub.1-6 alkenyl, C.sub.1-6 polyalkenyl, C.sub.1-6 alkynyl or C.sub.1-6 polyalkynyl group; or R.sup.5 is an OMEGA;R.sup.3, R.sup.4, R.sup.6 and R.sup.7, which may be the same or different, are independently H; or a C.sub.1-6 alkyl, C.sub.1-6 alkenyl, C.sub.1-6 polyalkenyl, C.sub.1-6 alkynyl or C.sub.1-6 polyalkynyl group; or halogen; or --OR.sup.8, --SR.sup.8, --(NR.sup.8 R.sup.9), where R.sup.8 and R.sup.9, which may be the same or different, are independently H; or alkyl groups having 1-6 carbons; or 1-2 substituted or unsubstituted alicyclic, heteroalicyclic, aromatic, or heteroaromatic rings, containing 1-4 heteroatoms, wherein the heteroatoms are O, N, or S; or R.sup.8 and R.sup.9 taken in combination are --(CH.sub.2).sub.2 --L--(CH.sub.2).sub.2 -- where L=--O--, --NR.sup.10 --, --CH.sub.2 -- or a single bond where R.sup.10 is H or an alkyl group having 1-6 carbons; or --OSO.sub.2 R.sup.19 where R.sup.19 is C.sub.1-6 alkyl, or C.sub.1-6 perfluoroalkyl, or aryl; or an OMEGA; or R.sup.6 and R.sup.7, taken in combination are --(CH.sub.2).sub.v -- where v=3 or 4, or R.sup.6 and R.sup.7 form a fused aromatic ring that is optionally further substituted;such that at least one of R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7, or a substituent on the aromatic ring formed by R.sup.6 and R.sup.7, is an OMEGA; where OMEGA is a cyclic substituent that is attached by a single bond.Fluorescent Dye II selectively stains either viable or non-viable cells with a detectable fluorescent response that is different from the fluorescent response of Dye I. The stained cells are illuminated at a suitable absorption wavelength, and the fluorescent response is detected to distinguish viable and non-viable cells based on the fluorescent response.

4. 发明授权

US5445946A Intravacuolar stains for yeast and other fungi 失效
标题翻译：阴道内污渍用于酵母和其他真菌
公开(公告)号：US5445946A
公开(公告)日：1995-08-29
申请号：US206081
申请日：1994-03-03
申请人： Bruce L. Roth , Paul J. Millard , Stephen T. Yue , Richard P. Haugland
发明人： Bruce L. Roth , Paul J. Millard , Stephen T. Yue , Richard P. Haugland
IPC分类号： C07D211/76 , C07D215/18 , C07D215/22 , C07D215/227 , C07D417/06 , C07D417/14 , C09B23/02 , C12Q1/04 , C07H17/00 , C12Q1/02 , C12Q1/68
CPC分类号： C07D211/76 , C07D215/18 , C07D215/227 , C07D417/06 , C07D417/14 , C09B23/02
摘要： The invention relates to a method of forming distinctive intravacuolar structures that are unique to fungal cells and can be correlated with cell viability. The preferred dyes of the present invention are described by the formula: ##STR1## wherein each R.sup.1 is independently H; or an alkyl group having from 1-6 carbons; or a trifluoromethyl; or a halogen; or --OR.sup.6, --SR.sup.6 or --(NR.sup.6 R.sup.7) where R.sup.6 and R.sup.7, which can be the same or different, are independently H; or alkyl groups having 1-6 carbons; or 1-2 alicyclic, heteroalicyclic, aromatic or heteroaromatic rings, containing 1-4 heteroatoms, wherein the heteroatoms are O, N or S; or R.sup.6 and R.sup.7 taken in combination are --(CH.sub.2).sub.2 --M--(CH.sub.2).sub.2 -- where M=a single bond, --O--, --CH.sub.2 --, or --NR.sup.8 -- where R.sup.8 is H or an alkyl having 1-6 carbons; and t=1-4;R.sup.2 is an alkyl group having 1-6 carbons;X is O, S, Se or NR.sup.9, where R.sup.9 is H or an alkyl group having 1-6 carbons; or X is CR.sup.10 R.sup.11 where R.sup.10 and R.sup.11, which may be the same or different, are independently alkyl groups having 1-6 carbons, or R.sup.10 and R.sup.11 taken in combination complete a five or six membered saturated ring;R.sup.3, R.sup.4 and R.sup.5, which may be the same or different, are independently H; or an alkyl, alkenyl, polyalkenyl, alkynyl or polyalkynyl group having 1-6 carbons; or a halogen; or --OH, --OR.sup.6, --SR.sup.6 or --(NR.sup.6 R.sup.7); or R.sup.4 and R.sup.5, taken in combination form a quinolinium ring system that is optionally similarly substituted or unsubstituted;Z.sup.- is a biologically compatible counterion;L is a halogen or good leaving group; andOMEGA is a saturated or unsaturated, substituted or unsubstituted, cyclic substituent.
摘要翻译：本发明涉及形成与真菌细胞独特的独特的血管内结构的方法，并且可以与细胞活力相关。本发明优选的染料用下式描述：其中每个R 1独立地是H; 或具有1-6个碳原子的烷基; 或三氟甲基; 或卤素; 或-OR 6，-SR 6或 - （NR 6 R 7）其中R 6和R 7可以相同或不同，独立地为H; 或具有1-6个碳的烷基; 或1-2个含有1-4个杂原子的脂环族，杂脂环，芳族或杂芳环，其中杂原子是O，N或S; 或R 6和R 7组合是 - （CH 2）2-M-（CH 2）2 - ，其中M =单键，-O-，-CH 2 - 或-NR 8 - ，其中R 8是H或具有1- 6个碳; 和t = 1-4; R2是具有1-6个碳原子的烷基; X是O，S，Se或NR 9，其中R 9是H或具有1-6个碳的烷基; 或X为CR10R11，其中R10和R11可以相同或不同，独立地为具有1-6个碳原子的烷基，或R10和R11组合完成一个五或六元饱和环; R 3，R 4和R 5可以相同或不同，独立地为H; 或具有1-6个碳原子的烷基，链烯基，聚链烯基，炔基或聚炔基; 或卤素; 或-OH，-OR 6，-SR 6或 - （NR 6 R 7）; 或R 4和R 5组合形成任选相似取代或未取代的喹啉鎓环系; Z-是一种生物相容的抗衡离子; L是卤素或良好的离去基团; 并且OMEGA是饱和或不饱和的，取代或未取代的环状取代基。

5. 发明授权

US5436134A Cyclic-substituted unsymmetrical cyanine dyes 失效
标题翻译：环状取代的不对称花青染料
公开(公告)号：US5436134A
公开(公告)日：1995-07-25
申请号：US90890
申请日：1993-07-12
申请人： Richard P. Haugland , Stephen T. Yue , Paul J. Millard , Bruce L. Roth
发明人： Richard P. Haugland , Stephen T. Yue , Paul J. Millard , Bruce L. Roth
IPC分类号： C07D211/76 , C07D215/18 , C07D215/22 , C07D215/227 , C07D417/06 , C07D417/14 , C09B23/02 , C12Q1/04 , C07H1/00 , C12Q1/68 , G01N33/00
CPC分类号： C07D215/227 , C07D213/64 , C07D215/18 , C07D409/04 , C07D413/06 , C07D417/06 , C07D417/14 , C09B23/02 , Y10S436/80 , Y10T436/143333
摘要： The invention describes the preparation and use of fluorescent stains for nucleic acids derived from unsymmetrical cyanine dyes. In particular, the invention describes unsymmetrical cyanine dyes having a saturated or unsaturated cyclic substituent. The dyes of the invention possess superior fluorescent characteristics when complexed with nucleic acids, and have utility in any application which requires detection of nucleic acids. The presence of the cyclic substituent results in improved permeability in a wide range of living cells, resulting in improved detection of intracellular nucleic acids.
摘要翻译：本发明描述了衍生自不对称花青染料的核酸的荧光染料的制备和用途。特别地，本发明描述了具有饱和或不饱和环状取代基的不对称花青染料。当与核酸复合时，本发明的染料具有优异的荧光特性，并且在需要检测核酸的任何应用中具有效用。环状取代基的存在导致在广泛范围的活细胞中改善的渗透性，导致细胞内核酸的改进的检测。

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