9-(2,6-dinitrophenoxycarbonyl)-10-(10-succinimidyloxycarbonyldecyl)acridinium trifluoromethanesulfonate | 845536-54-1

• 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: 9-(2,6-dinitrophenoxycarbonyl)-10-(10-succinimidyloxycarbonyldecyl)acridinium trifluoromethanesulfonate
• 英文别名: (2,6-Dinitrophenyl) 10-[11-(2,5-dioxopyrrolidin-1-yl)oxy-11-oxoundecyl]acridin-10-ium-9-carboxylate;trifluoromethanesulfonate
• CAS: 845536-54-1
• 化学式: CF₃O₃S*C₃₅H₃₅N₄O₁₀
• 分子量: 820.754
• InChiKey: HZIUGYZNSYRWAH-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  6.49
• 重原子数：
  57
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  251
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  9-吖啶羧酸 在 吡啶 、 氯化亚砜 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 1.0h， 生成 9-(2,6-dinitrophenoxycarbonyl)-10-(10-succinimidyloxycarbonyldecyl)acridinium trifluoromethanesulfonate
  参考文献：
  名称：

  新型 9-取代 10-(ω-(琥珀酰亚胺氧羰基)烷基)吖啶酯的合成、结构解析和化学发光活性

  摘要：

  几种新的吖啶酯2 – 9的中心吖啶环带有 9-(2,5-二甲基苯氧羰基)、9-(2,6-双(三氟甲基)苯氧羰基)或 9-(2,6-二硝基苯氧羰基)基团，以及合成了 10-甲基、10-(3-(琥珀酰亚胺氧羰基)丙基)、10-(5-(琥珀酰亚胺氧羰基)戊基)或 10-(10-(琥珀酰亚胺氧羰基)癸基)基团，并测试了它们的化学发光特性. 当用碱性过氧化氢处理时，2,5-二甲基苯基吖啶酯会缓慢发光（发光），而 2,6-二硝基苯基和 2,6-双（三氟甲基）苯基酯会快速发光（闪光）。10位的取代基影响化合物的水解稳定性。

  DOI：

  10.1002/bio.4474

文献信息

• Development and application of a novel acridinium ester for use as a chemiluminescent emitter in nucleic acid hybridisation assays using chemiluminescence quenching
  作者：Richard C. Brown、Zhaoqiang Li、Andrew J. Rutter、Xiaojing Mu、Owen H. Weeks、Keith Smith、Ian Weeks

  DOI：10.1039/b811947c

  日期：——

  Chemiluminescent acridinium esters (AEs) permit the development of high sensitivity ligand binding assays due to a combination of high intensity light emission and very low backgrounds. Here these advantages are exploited for use in homogeneous nucleic acid hybridisation assays using quenched chemiluminescence. AE chemiluminescence is conventionally initiated at highly alkaline pH. Novel “active” AEs were designed that permit initiation under conditions compatible with maintenance of nucleic acid hybrids (i.e. pH less than 9). Methyl red was found to be a dark quencher species capable of functioning at this pH. Practical application of the chemiluminescence quenching assay system has been demonstrated using two model nucleic acid hybridisation assays based on intra- and intermolecular emitter/quencher pairs.

  化学发光吖啶鎓酯（AE）具有高强度发光和极低背景的特点，因此可以开发高灵敏度的配体结合检测方法。在这里，我们将利用这些优势，使用淬灭化学发光法进行均相核酸杂交检测。AE 化学发光通常在高碱性 pH 下启动。我们设计了新型 "活性 "AE，可在与维持核酸杂交相适应的条件下（即 pH 值小于 9）启动。研究发现，甲基红是一种能在这种 pH 值下发挥作用的暗色淬灭剂。化学发光淬灭测定系统的实际应用已通过两种基于分子内和分子间发射器/淬灭器对的核酸杂交测定模型得到了验证。
• Chemiluminescent compounds
  申请人：Weeks Ian

  公开号：US20070166759A1

  公开（公告）日：2007-07-19

  The invention relates to chemiluminescent compounds of general formula: (I) wherein: either: R 1 is a reactive group capable of reacting with an amine or thiol moiety; L 1 is a hydrocarbon linker moiety comprising 2-12 carbon atoms, optionally substituted with hydroxy, halo, nitro or C 1 -C 4 alkoxy; and R 2 is hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, aryl, fused aryl, C 1 -C 4 alkoxy, C 1 -C 4 acyl, halide, hydroxy or nitro; or, alternatively: the combination R 1 -L 1 - comprises a C 1 -C 4 alkyl group optionally substituted with hydroxy, halo, nitro or C 1 -C 4 alkoxy; and R 2 comprises a group R 4 -L 1 -, where R 4 is a reactive group capable of reacting with an amine or thiol moiety; and L 1 is as defined above; L 2 is —C(═O)O—, —C(═O)—S— or —C(═O)N(SO 2 R 5 )—, wherein, in each case, the —C(═O) is linked to the ring carbon atom, and R 5 is C 1 -C 8 alkyl, aryl, C 1 -C 8 alkoxy or C 1 -C 8 acyl; R 3 a substituted C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 1 -C 8 alkynyl or aryl group wherein at least one of the said substituents is electron-withdrawing such that the pKa of the conjugate acid of the leaving group formed from R 3 and the —O, —S or —N(SO 2 R 5 ) of the L 2 group is ≦ about 9.5; and X − is an anion formed as the result of the synthesis and processing of the molecule; wherein the compound may contain one or more additional R 2 moieties on either or both outer rings, provided that only one of said R 2 moieties may comprise an R 4 -L 1 -group.

  该发明涉及通式为（I）的化学发光化合物，其中：要么：R1是能够与胺或硫醇基团反应的反应性基团；L1是包含2-12个碳原子的烃链连接基团，可选地被羟基，卤素，硝基或C1-C4烷氧基取代；R2是氢，C1-C4烷基，C1-C4卤代烷基，芳基，融合的芳基，C1-C4烷氧基，C1-C4酰基，卤素，羟基或硝基；或者，R1-L1-的组合包括一个可选地被羟基，卤素，硝基或C1-C4烷氧基取代的C1-C4烷基；R2包括一个R4-L1-基团，其中R4是能够与胺或硫醇基团反应的反应性基团；L1如上所定义；L2是—C(═O)O—，—C(═O)—S—或—C(═O)N(SO2R5)—，其中，在每种情况下，—C(═O)与环上的碳原子连接，并且R5是C1-C8烷基，芳基，C1-C8烷氧基或C1-C8酰基；R3是取代的C1-C8烷基，C2-C8烯基，C1-C8炔基或芳基基团，其中至少一个取代基是电子提取基团，使得由R3和L2中的—O，—S或—N(SO2R5)形成的离去基的共轭酸的pKa≤约9.5；X-是分子合成和处理的结果形成的阴离子；其中化合物可以在一个或两个外环上包含一个或多个额外的R2基团，只有一个该R2基团可以包含一个R4-L1-基团。
• Chemiluminescent Compounds
  申请人：WEEKS Ian

  公开号：US20110082279A1

  公开（公告）日：2011-04-07

  The invention relates to chemiluminescent compounds of general formula (I) wherein: either: R 1 is a reactive group capable of reacting with an amine or thiol moiety; L 1 is a hydrocarbon linker moiety comprising 2-12 carbon atoms, optionally substituted with hydroxy, halo, nitro or C 1 -C 4 alkoxy; and R 2 is hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, aryl, fused aryl, C 1 -C 4 alkoxy, C 1 -C 4 acyl, halide, hydroxy or nitro; or, alternatively: the combination R 1 -L 1 - comprises a C 1 -C 4 alkyl group optionally substituted with hydroxy, halo, nitro or C 1 -C 4 alkoxy; and R 2 comprises a group R 4 -L 1 -, where R 4 is a reactive group capable of reacting with an amine or thiol moiety; and L 1 is as defined above; L 2 is —C(═O)O—, —C(═O)—S— or —C(═O)N(SO 2 R 5 )—, wherein, in each case, the —C(═O) is linked to the ring carbon atom, and R 5 is C 1 -C 8 alkyl, aryl, C 1 -C 8 alkoxy or C 1 -C 8 acyl; R 3 is a substituted C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl or aryl group wherein at least one of the said substituents is electron-withdrawing such that the pKa of the conjugate acid of the leaving group formed from R 3 and the —O, —S or —N(SO 2 R 5 ) of the L 2 group is ≦about 9.5; and X − is an anion formed as the result of the synthesis and processing of the molecule; wherein the compound may contain one or more additional R 2 moieties on either or both outer rings, provided that only one of said R 2 moieties may comprise an R 4 -L 1 -group.

  本发明涉及通式（I）的化学发光化合物，其中： 要么： R1是能够与胺或硫醇基团反应的反应性基团； L1是一个含有2-12个碳原子的烃链连接基团，可选地被羟基，卤素，硝基或C1-C4烷氧基取代； R2是氢，C1-C4烷基，C1-C4卤代烷基，芳基，融合芳基，C1-C4烷氧基，C1-C4酰基，卤素，羟基或硝基； 或者，另一种情况是： 组合R1-L1-包括一个C1-C4烷基，可选地被羟基，卤素，硝基或C1-C4烷氧基取代； R2包括一个R4-L1-基团，其中R4是能够与胺或硫醇基团反应的反应性基团；L1如上定义； L2是-C（═O）O-，-C（═O）-S-或-C（═O）N（SO2R5）-，在每种情况下，-C（═O）连接到环碳原子，并且R5是C1-C8烷基，芳基，C1-C8烷氧基或C1-C8酰基； R3是取代的C1-C8烷基，C2-C8烯基，C2-C8炔基或芳基，其中至少一个取代基是电子吸引基团，使得由R3和L2基团的-O，-S或-N（SO2R5）形成的离去基的共轭酸的pKa ≦约9.5； X-是分子合成和处理的结果形成的阴离子；其中化合物可以在一个或两个外环上包含一个或多个额外的R2基团，只有其中一个R2基团可以包含一个R4-L1-基团。
• ESTIMATION OF ACTIVITY OR INHIBITION OF PROCESSES INVOLVED IN NUCLEIC ACID MODIFICATION USING CHEMILUMINESCENCE QUENCHING
  申请人：Molecular Light Technology Research Limited

  公开号：EP1658381A2

  公开（公告）日：2006-05-24
• CHEMILUMINESCENT COMPOUNDS
  申请人：Molecular Light Technology Research Limited

  公开号：EP1658503A1

  公开（公告）日：2006-05-24