(4-Methoxycarbonyl-2,6-dimethylphenyl) 2,7-dihydroxyacridine-9-carboxylate | 866365-92-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (4-Methoxycarbonyl-2,6-dimethylphenyl) 2,7-dihydroxyacridine-9-carboxylate
• CAS: 866365-92-6
• 化学式: C₂₄H₁₉NO₆
• 分子量: 417.418
• InChiKey: BDEUKELOGBVKOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (4-Methoxycarbonyl-2,6-dimethylphenyl) 2,7-dihydroxyacridine-9-carboxylate 在 盐酸 、 2,6-二叔丁基吡啶 、 偶氮二甲酸二异丙酯 、 三苯基膦 、 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 42.0h， 生成 3,3'-((((9-((4-carboxy-2,6-dimethylphenoxy)carbonyl)-10-(3-sulfonatopropyl)acridine-10-ium-2,7-diyl)bis(oxy))bis(hexane-6,1-diyl))bis(dimethylammoniumdiyl))bis(propane-1-sulfonate)
  参考文献：
  名称：

  [EN] ZWITTERION-CONTAINING ACRIDINIUM COMPOUNDS
  [FR] COMPOSÉS D'ACRIDINIUM CONTENANT DU ZWITTERION

  摘要：

  透明性好、亲水性强的含有带电离子的吖啶化合物被揭示。这些吖啶化合物在免疫化学分析等领域中作为化学发光标记物时，表现出对固相的非特异性结合减少，提供了增加的分析灵敏度。

  公开号：

  WO2011060228A1

文献信息

• Effect of branching in remote substituents on light emission and stability of chemiluminescent acridinium esters
  作者：Anand Natrajan、David Wen

  DOI：10.1039/c4ra02516d

  日期：——

  Acridinium dimethylphenyl esters are widely used as chemiluminescent labels in automated immunoassays for clinical diagnostics in Siemens Healthcare Diagnostics' ADVIA Centaur® systems.

  乙酰胺二甲基苯酯在西门子医疗诊断的ADVIA Centaur®系统中被广泛用作自动免疫分析中的化学发光标记剂，用于临床诊断。
• [EN] N-ALKYLATION OF ACRIDANS<br/>[FR] N-ALKYLATION D'ACRIDANES
  申请人：SIEMENS HEALTHCARE DIAGNOSTICS INC

  公开号：WO2020005920A1

  公开（公告）日：2020-01-02

  The present invention provides compounds used in the synthesis of chemiluminescent acridinium compounds and methods of producing these compounds. Specifically, methods are provided for the N-alkylation of acridan compounds using alkylating reagents. Typically, these alkylating reagents comprise a protected sulfonate group protected with an acid-labile protecting group.

  本发明提供了用于合成化学发光吖啶化合物的化合物以及制备这些化合物的方法。具体而言，提供了使用烷基化试剂对吖啶化合物进行N-烷基化的方法。通常，这些烷基化试剂包括一个受酸稳定保护基保护的受保护磺酸酯基。
• HYDROPHILIC HIGH QUANTUM YIELD ACRIDINIUM ESTERS WITH IMPROVED STABILITY AND FAST LIGHT EMISSION
  申请人：SIEMENS HEALTHCARE DIAGNOSTICS INC.

  公开号：US20170320830A1

  公开（公告）日：2017-11-09

  Hydrophilic, high quantum yield, chemiluminescent acridinium compounds with increased light output, improved stability, fast light emission and decreased non specific binding are disclosed. The chemiluminescent acridinium esters possess hydrophilic, branched, electron-donating functional groups at the C2 and/or C7 positions of the acridinium nucleus.

  本发明揭示了具有增强的光输出、改善稳定性、快速光发射和减少非特异性结合的亲水性、高量子产率、化学发光的蒽醌化合物。这些化学发光的蒽醌酯在蒽醌核的C2和/或C7位置具有亲水性、分支的电子给体功能团。
• Synthesis and properties of differently charged chemiluminescent acridinium ester labels
  作者：Anand Natrajan、David Sharpe

  DOI：10.1039/c2ob27190g

  日期：——

  Chemiluminescent acridinium dimethylphenyl esters containing N-sulfopropyl groups in the acridinium ring are highly sensitive, hydrophilic labels that are used in automated immunoassays for clinical diagnostics. Light emission from these labels is triggered with alkaline peroxide in the presence of a cationic surfactant. At physiological pH, N-sulfopropyl acridinium esters exist as water adducts that are commonly referred to as pseudobases. Pseudobase formation, which results from addition of water to the zwitterionic N-sulfopropyl acridinium ring, neutralizes the positive charge on the acridinium nitrogen and imparts a net negative charge to the label due to the sulfonate moiety. As a consequence, N-sulfopropyl acridinium ester conjugates of small molecule haptens as well as large molecules such as proteins gain negative charges at neutral pH. In the current study, we describe the synthesis and properties of two new hydrophilic acridinium dimethylphenyl ester labels where the net charge in the labels was altered. In one label, the structure of the hydrophilic N-alkyl group attached to the acridinium ring was changed so that the pseudobase of the label contains no net charge. In the second acridinium ester, two additional negative charges in the form of sulfopropyl groups were added to the acridinium ring to make this label's pseudobase strongly anionic. Chemiluminescence measurements of these labels, as well as their conjugates of an antibody with a neutral pI, indicate that acridinium ester charge while having a modest effect on emission kinetics has little influence on light output. However, our results demonstrate that acridinium ester charge can affect protein pI, apparent chemiluminescence stability and non-specific binding of protein conjugates to microparticles. These results emphasize the need for careful consideration of acridinium ester charge in order to optimize reagent stability and performance in immunoassays. In the current study, we observed that for a neutral protein, an acridinium ester with a hydrophilic but charge-neutral N-alkyl group afforded faster light emission, lower non-specific binding and better chemiluminescence stability than an analogous label with an anionic N-alkyl group.

  吖啶环中含有 N-磺丙基的化学发光吖啶二甲基苯酯是高度敏感的亲水性标记，用于临床诊断的自动免疫测定。这些标签的发光是在阳离子表面活性剂存在下用碱性过氧化物触发的。在生理 pH 值下，N-磺丙基吖啶酯以水加合物形式存在，通常称为假碱。假碱基的形成是由于向两性离子 N-磺丙基吖啶鎓环添加水而形成的，中和了吖啶鎓氮上的正电荷，并由于磺酸盐部分而赋予标记净负电荷。因此，小分子半抗原以及蛋白质等大分子的 N-磺丙基吖啶酯缀合物在中性 pH 下会获得负电荷。在当前的研究中，我们描述了两种新型亲水吖啶二甲基苯酯标签的合成和性质，其中标签中的净电荷发生了改变。在一种标记中，连接到吖啶鎓环上的亲水性N-烷基的结构发生了改变，使得标记的假碱基不含有净电荷。在第二种吖啶酯中，吖啶环上添加了两个额外的磺丙基形式的负电荷，使该标记的假碱具有强阴离子性。这些标记及其中性等电点抗体缀合物的化学发光测量表明，吖啶酯电荷虽然对发射动力学影响不大，但对光输出影响很小。然而，我们的结果表明吖啶酯电荷可以影响蛋白质 pI、表观化学发光稳定性以及蛋白质缀合物与微粒的非特异性结合。这些结果强调需要仔细考虑吖啶酯电荷，以优化免疫测定中试剂的稳定性和性能。在当前的研究中，我们观察到，对于中性蛋白质，具有亲水性但电荷中性的N-烷基的吖啶酯比具有阴离子N-烷基的类似标记具有更快的光发射、更低的非特异性结合和更好的化学发光稳定性。烷基。
• High quantum yield acridinium compounds and their uses in improving assay sensitivity
  申请人：Natrajan Anand

  公开号：US20050221390A1

  公开（公告）日：2005-10-06

  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.

  本发明涉及亲水性高、量子产率高的吖啶化合物。已经发现，在吖啶环系统中引入电子供体基团可以增加相应吖啶化合物在碱性过氧化物触发化学发光时发射的光量。更具体地说，已经发现，在吖啶化合物的吖啶环系统的C-2和/或C-7位置引入一个或两个亲水性的烷氧基团可以增加它们的量子产率并增强这些化合物的水溶性。本发明的亲水性高、量子产率高的吖啶化合物可用作化学发光标记物，以提高免疫测定的灵敏度。