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    Measurement of hydride using chemiluminescent acridinium compounds and applications thereof
    12.
    发明授权
    Measurement of hydride using chemiluminescent acridinium compounds and applications thereof 有权
    使用化学发光吖啶化合物测量氢化物及其应用

    公开(公告)号：US06673560B1

    公开(公告)日：2004-01-06

    申请号：US09448522

    申请日：1999-11-23

    申请人： David Sharpe ,  Anand Natrajan ,  Qingping Jiang ,  George Parsons ,  Say-Jong Law

    发明人： David Sharpe ,  Anand Natrajan ,  Qingping Jiang ,  George Parsons ,  Say-Jong Law

    IPC分类号： G01N33536

    CPC分类号： G01N33/582 ,  C12Q1/008 ,  G01N33/581 ,  Y10S436/80 ,  Y10S436/815 ,  Y10T436/204165

    摘要： The present invention discloses a method for the measurement of hydride using a chemiluminescent compound. The preferred chemiluminescent molecule is an acridinium compound. The source of hydride for the reduction of acridinium compound may be of chemical or biochemical origin, or the result of enzymatic catalysis. The chemical source of hydride, for example, might be metal hydrides, such as NaBH4. A biochemical source of hydride might be that derived from NADH, or NADPH, while an enzymatic source would be the class of oxidoreductases termed dehydrogenases which convert NADH or NADPH from NAD or NADP. There are numerous potential applications for acridinium compounds as chemiluminescent indicators of hydride. Any applied tests or diagnostic assays, in which hydride is either present at the onset of or generated through the course of a reaction, would benefit from the present invention. Such tests, which could encompass many different formats as discussed below in detail, may involve the quantitation or detection of metal hydrides, or enzyme cofactors such as NADH, NADPH, FMNH2, or FADH2. Of particular importance, are those diagnostic assays which might use dehydrogenases as reagents, indicators, diagnostic markers or as labels. Ethanol, for example, might be detected with acridinium ester chemiluminescence through the reaction of alcohol dehydrogenase on ethanol, said reaction producing NADH. As a label, dehydrogenase might be used in an ELISA for the detection of a specific analyte with acridinium ester providing the signaling response. Nucleic acid assays using dehydrogenase as a label are also envisioned. Assays for the detection of clinically relevant dehydrogenases such as elevated glutamate dehydrogenase as an indicator of hepatocellular damage might also be developed.

    摘要翻译： 本发明公开了一种使用化学发光化合物测量氢化物的方法。 优选的化学发光分子是吖啶鎓化合物。 用于还原吖啶鎓化合物的氢化物源可以是化学或生物化学来源或酶催化的结果。 氢化物的化学源例如可以是金属氢化物，例如NaBH 4。 氢化物的生物化学来源可能是衍生自NADH或NADPH的酶，而酶源则是称为脱氢酶的氧化还原酶类，其从NAD或NADP转化NADH或NADPH。吖啶鎓化合物作为氢化物的化学发光指示剂有许多潜在应用 。 氢化物在反应过程中出现或产生的任何应用测试或诊断测定将从本发明中受益。 可以包括下面详细讨论的许多不同形式的这种测试可以涉及金属氢化物或酶辅因子如NADH，NADPH，FMNH 2或FADH 2的定量或检测。 特别重要的是那些可能使用脱氢酶作为试剂，指示剂，诊断标记物或标签的诊断测定法。 例如，乙醇可以通过醇脱氢酶对乙醇的反应用吖啶酯化学发光检测，所述反应产生NADH。 作为标记，脱氢酶可用于ELISA中，以检测具有吖啶酯的特异性分析物，从而提供信号反应。 也可以设想使用脱氢酶作为标记的核酸测定。 检测临床相关脱氢酶（如升高的谷氨酸脱氢酶作为肝细胞损伤指标）的检测也可能被开发出来。

    High quantum yield acridinium compounds and their uses in improving assay sensitivity
    16.
    发明授权
    High quantum yield acridinium compounds and their uses in improving assay sensitivity 有权
    高量子产率吖啶鎓化合物及其在提高测定灵敏度方面的应用

    公开(公告)号：US07309615B2

    公开(公告)日：2007-12-18

    申请号：US11142938

    申请日：2005-06-02

    申请人： Anand Natrajan ,  Qingping Jiang ,  David Sharpe ,  James Costello

    发明人： Anand Natrajan ,  Qingping Jiang ,  David Sharpe ,  James Costello

    IPC分类号： G01N33/533 ,  G01N33/537 ,  G01N33/53 ,  C07D219/00

    CPC分类号： G01N33/533 ,  B82Y15/00 ,  C07D219/04 ,  C07D219/06 ,  G01N33/542 ,  G01N33/582 ,  G01N33/588 ,  Y10S435/968 ,  Y10S436/80 ,  Y10S436/805

    摘要： The present invention relates to hydrophilic, high quantum yield acridinium compounds. It has been discovered that the placement of electron-donating groups in the acridinium ring system increases the amount of light that is emitted by the corresponding acridinium compound when its chemiluminescence is triggered by alkaline peroxide. More specifically, it has been found that the placement of one or two hydrophilic, alkoxy groups at the C-2 and/or C-7 position of the acridinium ring system of acridinium compounds increases their quantum yield and enhances the aqueous solubility of these compounds. The present hydrophilic, high quantum yield, acridinium compounds are useful chemiluminescent labels for improving the sensitivity of immunoassays.

    摘要翻译： 本发明涉及亲水性高量子产率吖啶鎓化合物。 已经发现，当其化学发光由碱性过氧化物触发时，电子给体基团在吖啶环体系中的放置增加了相应的吖啶鎓化合物发射的光的量。 更具体地，已经发现，在吖啶鎓化合物的吖啶环体系的C-2和/或C-7位置上放置一个或两个亲水性烷氧基增加其量子产率并增强这些化合物的水溶性 。 本发明的亲水性，高量子产率的吖啶化合物是有用的化学发光标记，用于提高免疫测定的灵敏度。

    Chemiluminescent acridinium compounds and analogues thereof as substrates of hydrolytic enzymes
    17.
    发明授权
    Chemiluminescent acridinium compounds and analogues thereof as substrates of hydrolytic enzymes 有权
    化学发光吖啶鎓化合物及其类似物作为水解酶的底物

    公开(公告)号：US07097995B2

    公开(公告)日：2006-08-29

    申请号：US10928300

    申请日：2004-08-27

    申请人： Qingping Jiang ,  Anand Natrajan ,  David J. Sharpe ,  Wen-Jee Wong ,  Say-Jong Law

    发明人： Qingping Jiang ,  Anand Natrajan ,  David J. Sharpe ,  Wen-Jee Wong ,  Say-Jong Law

    IPC分类号： C12Q1/34

    CPC分类号： C07D491/10 ,  C07D219/04 ,  C07F9/64 ,  C12Q1/42 ,  C12Q2334/00 ,  G01N33/533 ,  G01N33/582

    摘要： A chemiluminescent substrate of a hydrolytic enzyme having the following general Formula I is disclosed, as follows: Lumi-M-PFormula I where “Lumi” is a chemiluminescent moiety capable of producing light (a) by itself, (b) with MP attached and (c) with M attached. Examples of Lumi include chemiluminescent acridinium compounds, benzacridinium compounds, quinolinium compounds, isoquinolinium compounds, phenanthridinium compounds, and lucigenin compounds, spiroacridan compounds, luminol compounds and isoluminol compounds. M is a multivalent heteroatom having at least one lone pair of electrons selected from oxygen, nitrogen and sulfur, directly attached to the light emitting moiety of Lumi at one end and to P at the other end. P is a group that can be readily removed by hydrolytic enzymes. An enzymatic reaction utilizing the above compound is the following: where HE is a hydrolytic enzyme. Lumi-M is a chemiluminescent product having physical and/or chemical properties different from those of Lumi-M-P.

    摘要翻译： 公开了具有以下通式I的水解酶的化学发光底物，如下：<？在线公式描述=“在线公式”末端=“铅”→> Lumi-M-PFormula I < -line-formula description =“In-line Formulas”end =“tail”？>其中“Lumi”是能够自身产生光的化学发光部分（a），（b）MP附着和（c）M附着 。 Lumi的实例包括化学发光吖啶鎓化合物，苯并吖啶鎓化合物，喹啉鎓化合物，异喹啉鎓化合物，菲啶鎓化合物和光合精化合物，螺吡啶化合物，鲁米诺化合物和异鲁米诺化合物。 M是具有至少一个选自氧，氮和硫的孤对电子的多价杂原子，其一端直接连接到Lumi的发光部分，另一端直接附着于P。 P是可以通过水解酶容易地除去的基团。 使用上述化合物的酶反应如下：其中HE是水解酶。 Lumi-M是具有与Lumi-M-P不同的物理和/或化学性质的化学发光产物。

    Chemiluminescent acridinium compounds and analogues thereof as substrates of hydrolytic enzymes
    19.
    发明授权
    Chemiluminescent acridinium compounds and analogues thereof as substrates of hydrolytic enzymes 有权
    化学发光吖啶鎓化合物及其类似物作为水解酶的底物

    公开(公告)号：US06783948B1

    公开(公告)日：2004-08-31

    申请号：US09626566

    申请日：2000-07-27

    申请人： Qingping Jiang ,  Anand Natrajan ,  David J. Sharpe ,  Wen-Jee Wong ,  Say-Jong Law

    发明人： Qingping Jiang ,  Anand Natrajan ,  David J. Sharpe ,  Wen-Jee Wong ,  Say-Jong Law

    IPC分类号： C12Q134

    CPC分类号： C07D491/10 ,  C07D219/04 ,  C07F9/64 ,  C12Q1/42 ,  C12Q2334/00 ,  G01N33/533 ,  G01N33/582

    摘要： A chemiluminescent substrate of hydrolytic enzyme having the following general Formula I, as follows: Lumi-M-P  Formula I where “Lumi” is a chemiluminescent moiety capable of producing light (a) by itself, (b) with MP attached and (c) with M attached. Examples of Lumi include chemiluminescent acridinium compounds, benzacridinium compounds, quinolinium compounds, isoquinolinium compounds, phenanthridinium compounds, and lucigenin compounds, spiroacridan compounds, luminol compounds and isoluminol compounds. M is a multivalent heteroatom having at least one lone pair of electrons selected from oxygen, nitrogen and sulfur, directly attached to the light emitting moiety of Lumi at one end and to P at the other end. P it a group that can be readily removed by hydrolytic enzymes. An enzymatic reaction utilizing the above compound is the following: where HE is a hydrolytic enzyme Lumi-M is a chemiluminescent product having physical and/or chemical properties different from those of Lumi-M-P.

    摘要翻译： 具有以下通式I的水解酶的化学发光底物如下：其中“Lumi”是能够自身产生光的化学发光部分（a），（b）MP附着的（c）和M连接的化合物发光部分。 Lumi的实例包括化学发光吖啶鎓化合物，苯并吖啶鎓化合物，喹啉鎓化合物，异喹啉鎓化合物，菲啶鎓化合物和光合精化合物，螺吡啶化合物，鲁米诺化合物和异鲁米诺化合物。 M是具有至少一个选自氧，氮和硫的孤对电子的多价杂原子，其一端直接连接到Lumi的发光部分，另一端直接附着于P。 P是可以通过水解酶容易地除去的基团。 使用上述化合物的酶反应如下：其中HE是水解酶，Lumi-M是具有与Lumi-M-P不同的物理和/或化学性质的化学发光产物。