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    AZA-BENZAZOLIUM CONTAINING CYANINE DYES
    1.
    发明申请
    AZA-BENZAZOLIUM CONTAINING CYANINE DYES 有权
    含AZA-BENZAZOLIUM含有氰基染料

    公开(公告)号：US20110217696A1

    公开(公告)日：2011-09-08

    申请号：US12984380

    申请日：2011-01-04

    Applicant: Richard P. HAUGLAND ,  Stephen T. Yue

    Inventor： Richard P. HAUGLAND ,  Stephen T. Yue

    IPC: C12Q1/68 ,  C07D498/04 ,  G01N33/50 ,  C07D513/04

    CPC classification number: 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

    Abstract: 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.

    Abstract translation: 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。

    Fluorescent viability assay using cyclic-substituted unsymmetrical cyanine dyes
    5.
    发明授权
    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

    Applicant: Paul J. Millard ,  Bruce L. Roth ,  Stephen T. Yue ,  Richard P. Haugland

    Inventor： Paul J. Millard ,  Bruce L. Roth ,  Stephen T. Yue ,  Richard P. Haugland

    IPC: 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 classification number: C07D211/76 ,  C07D215/18 ,  C07D215/227 ,  C07D417/06 ,  C07D417/14 ,  C09B23/02 ,  Y10S436/80 ,  Y10T436/143333

    Abstract: 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.

    Intravacuolar stains for yeast and other fungi
    6.
    发明授权
    Intravacuolar stains for yeast and other fungi 失效
    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

    Applicant: Bruce L. Roth ,  Paul J. Millard ,  Stephen T. Yue ,  Richard P. Haugland

    Inventor： Bruce L. Roth ,  Paul J. Millard ,  Stephen T. Yue ,  Richard P. Haugland

    IPC: C07D211/76 ,  C07D215/18 ,  C07D215/22 ,  C07D215/227 ,  C07D417/06 ,  C07D417/14 ,  C09B23/02 ,  C12Q1/04 ,  C07H17/00 ,  C12Q1/02 ,  C12Q1/68

    CPC classification number: C07D211/76 ,  C07D215/18 ,  C07D215/227 ,  C07D417/06 ,  C07D417/14 ,  C09B23/02

    Abstract: 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.

    Abstract translation: 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。

    Aza-benzazolium containing cyanine dyes
    9.
    发明授权
    Aza-benzazolium containing cyanine dyes 有权
    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

    Applicant: Richard P. Haugland ,  Stephen T. Yue

    Inventor： Richard P. Haugland ,  Stephen T. Yue

    IPC: C12Q168

    CPC classification number: 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

    Abstract: 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.

    Abstract translation: 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。

    Neutral unsymmetrical cyanine dyes
    10.
    发明授权
    Neutral unsymmetrical cyanine dyes 失效
    中性不对称花青染料

    公开(公告)号：US5656449A

    公开(公告)日：1997-08-12

    申请号：US400026

    申请日：1995-03-06

    Applicant: Stephen T. Yue

    Inventor： Stephen T. Yue

    IPC: C07D413/06 ,  C07D417/06 ,  G01N33/50 ,  C12Q1/04 ,  C12Q1/00 ,  C12Q1/32 ,  G01N33/53

    CPC classification number: C07D413/06 ,  C07D417/06 ,  G01N33/5005 ,  Y10S435/968 ,  Y10S435/975 ,  Y10S436/80 ,  Y10T436/143333

    Abstract: The invention describes the preparation and use of fluorescent stains for nucleic acids derived from neutral unsymmetrical cyanine dyes comprising a substituted benzazolium ring system linked to a methine bridge to a pyridine or quinoline ring system. The fluorescence characteristics of the dyes when complexed with nucleic acids give the dyes utility for the detection of oligonucleotides and nucleic acids in cells, gels and solutions. The dyes have particular utility in the staining of reticulocytes.

    Abstract translation: 本发明描述了衍生自中性非对称花青染料的核酸的荧光染料的制备和用途，其包含连接到次甲基桥与吡啶或喹啉环系统的取代的苯并唑鎓环系统。 当与核酸复合时，染料的荧光特性使得染料可用于检测细胞，凝胶和溶液中的寡核苷酸和核酸。 这些染料在网织红细胞的染色中具有特殊的用途。

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