2-anthraquinonecarboxylic acid N-hydroxysuccinimide ester | 152773-20-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-anthraquinonecarboxylic acid N-hydroxysuccinimide ester
• 英文别名: Anthraquinone 2-carboxylic acid N-hydroxysuccinimide；anthraquinone-2-carboxylic acid N-hydroxysuccinimide ester；2,5-dioxopyrrolidin-1-yl 9,10-dioxo-4a,9,9a,10-tetrahydroanthracene-2-carboxylate；anthraquinonecarboxylic acid N-hydroxysuccinimidyl ester；2,5-Dioxopyrrolidin-1-yl 9,10-dioxo-9,10-dihydroanthracene-2-carboxylate；(2,5-dioxopyrrolidin-1-yl) 9,10-dioxoanthracene-2-carboxylate
• CAS: 152773-20-1
• 化学式: C₁₉H₁₁NO₆
• 分子量: 349.299
• InChiKey: QQYRRDQGFRUNIJ-UHFFFAOYSA-N

物化性质

• 沸点：
  575.3±60.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  97.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  、 2-anthraquinonecarboxylic acid N-hydroxysuccinimide ester 以 水 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Direct Labeling of 5-Methylcytosine and Its Applications

  摘要：

  Cytosine methylation is one of the most important epigenetic events, and much effort has been directed to develop a simple reaction for methylcytosine detection. In this paper, we describe the design of tag-attachable ligands for direct methylcytosine labeling and their application to fluorescent and electrochemical assays. The effect of the location of bipyridine substituents on the efficiency of osmium complexation at methylcytosine was initially investigated. As a result, a bipyridine derivative with a substituent at the C4 position showed efficient complexation at the methylcytosine residue of single-stranded DNA in a reaction mixture containing potassium osmate and potassium hexacyanoferrate(III). On the basis of this result, a bipyridine derivative with a tag-attachable amino linker at the C4 position was synthesized. The efficiency of metal complex formation in the presence of the osmate and the synthetic ligand was clearly changed by the presence/absence of a methyl group at the C5 position of cytosine. The succinimidyl esters of functional labeling units were then attached to the bipyridine ligand fixed on the methylcytosine. These labels attached to methylcytosine enabled us to detect the target methylcytosine in DNA both fluorometrically and electrochemically. For example, we were able to fluorometrically obtain information on the methylation status at a specific site by means of fluorescence resonance energy transfer from a hybridized fluorescent DNA probe to a fluorescent label on methylcytosine. In addition, by the combination of electrochemically labeled methylcytosine and an electrode modified by probe DNAs, a methylcytosine-selective characteristic current signal was observed. This direct labeling of methylcytosine is a conceptually new methylation detection assay with many merits different from conventional assays.

  DOI：

  10.1021/ja068660c
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 蒽醌-2-羧酸 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-anthraquinonecarboxylic acid N-hydroxysuccinimide ester
  参考文献：
  名称：

  使用新型二氧化硅负载的敏化剂对α-萜品烯进行可见光光敏氧化：光氧化与光脱氢

  摘要：

  制备并表征了三种基于玫瑰红（RB），蒽醌-2-羧酸（ANT-COOH）和新型氰基蒽衍生物（DBTP-COOH）的二氧化硅固定的有机光催化剂。比较了它们对α-萜品烯的光氧化效率与可溶对应物的光氧化效率。在溶液中，这三种敏化剂显示出单重态氧产生的高量子产率。在没有催化剂的情况下，对对甲基异丙基苯会发生明显的自氧化作用，而敏化反应的机理则主要取决于敏化剂的结构。使用DBTP和RB材料，通过单线态氧的添加迅速生成了scar啶。相反，基于ANT的敏化剂有利于将光脱氢成p通过电子转移步骤引起的异丁香精引发自由基链反应，然后在长时间照射下进一步进行对丁香精氧化。使用基于DBTP的材料进行光氧合，以及使用基于ANT的材料进行光脱氢，均获得了最高的效率和选择性，这些性能使其成为太阳能合成，废物处理和微流反应器中固定化光催化剂的未来应用之选。

  DOI：

  10.1016/j.jcat.2013.04.001

文献信息

• Electrochemical primer extension for the detection of single nucleotide polymorphisms in the cardiomyopathy associated MYH7 gene
  作者：A. M. Debela、S. Thorimbert、B. Hasenknopf、C. K. O'Sullivan、M. Ortiz

  DOI：10.1039/c5cc07762a

  日期：——

  We report the labelling of dideoxy nucleotides (ddNTPs) for use in electrochemical array based primer extension for the detection of single nucleotide polymorphisms (SNPs).

  我们报道了二氧基核苷酸（ddNTPs）的标记，用于基于电化学阵列的引物延伸，用于检测单核苷酸多态性（SNPs）。
• Intraduplex DNA-Mediated Electrochemistry of Covalently Tethered Redox-Active Reporters
  作者：Catrina G. Pheeney、Jacqueline K. Barton

  DOI：10.1021/ja408135g

  日期：2013.10.9

  Intraduplex DNA-mediated reduction is established as a general mechanism for the reduction of distally bound stacked redox-active species covalently tethered to DNA through flexible alkane linkages. Methylene Blue (MB), Nile Blue (NB), and Anthraquinone (AQ) were covalently tethered to DNA with three different covalent linkages. Using these reporters DNA electrochemistry was shown to be both DNA-mediated

  双链内 DNA 介导的还原被确立为减少远端结合的堆叠氧化还原活性物质通过灵活的烷烃键共价连接到 DNA 的一般机制。亚甲蓝 (MB)、尼罗蓝 (NB) 和蒽醌 (AQ) 通过三个不同的共价键共价连接到 DNA。使用这些报告基因的 DNA 电化学被证明是 DNA 介导的和内部双链体，而不是内部双链体。重要的是，通过 DNA π-stack 发生的电荷传输路径是通过使用介入的 AC 错配来打破这条路径来建立的。DNA 介导的 MB 减少主要通过双链内插入发生，这一事实是通过改变相邻双链 DNA 的接近度和完整性来确定的。
• DNA duplexes covalently labeled at two sites: synthesis and characterization by steady-state and time-resolved optical spectroscopies
  作者：Joshua Telser、Kenneth A. Cruickshank、Larry E. Morrison、Thomas L. Netzel、Chi Kin Chan

  DOI：10.1021/ja00200a050

  日期：1989.8

  Synthese d'oligonucleotides ayant comme sequence de base 5'-G-C-A-G(T*-L)-C-A-G-3' et 5'-C-T-G-A-G(T*-L)-G-C-3' ou T* est la thymidine modifiee (la thymine possede un groupement NH 2 terminal) permettant la liaison avec soit le pyrenebutyrate ou le pyrenesulfonate ou avec des anthraquinones (L)

  合成这些 d'寡核苷酸 5'-GCAG(T*-L)-CAG-3' 和 5'-CTGAG(T*-L)-GC-3' 或 T* est la thymidine modifiee (la thymine拥有联合国集团 NH 2 终端）permettant la liaison avec soit le pyrenebutyrate ou le 芘磺酸 ou avec des anthraquinones (L)
• Probe Unit, Apparatus for Identifying Nucleotide Region and Method of Identifying Nucleotide Region
  申请人：Okamoto Akimitsu

  公开号：US20080302674A1

  公开（公告）日：2008-12-11

  A probe unit for identifying a target nucleotide region in a target nucleic acid, the unit being provided with an electrode, a probe bound to the electrode and recognizes the target nucleic acid, and a hole-transfer-inducing agent bound to the probe, wherein a nucleotide region corresponding to the target nucleotide region is located between the hole-transfer-inducing-agent-binding site and the electrode-binding end of the probe. A state of the target nucleotide region in the target nucleic acid can be identified by comparing electrochemical signal levels by energy-induced hole transfers before and after the hybridization of such a probe unit with the target nucleic acid.

  一种用于识别目标核酸中的目标核苷酸区域的探针单元，该单元具有电极、与电极结合并识别目标核酸的探针和结合于探针上的孔传输诱导剂，其中与目标核苷酸区域相对应的核苷酸区域位于孔传输诱导剂结合位点和探针的电极结合端之间。通过比较探针单元与目标核酸杂交前后通过能量诱导的孔传输产生的电化学信号水平，可以确定目标核酸中目标核苷酸区域的状态。
• PROBE UNIT, APPARATUS FOR IDENTIFYING NUCLEOTIDE REGION AND METHOD OF IDENTIFYING NUCLEOTIDE REGION
  申请人：Kyoto University

  公开号：EP1830183A1

  公开（公告）日：2007-09-05

  A probe unit for identifying a target nucleotide region in a target nucleic acid, the unit being provided with an electrode, a probe bound to the electrode and recognizes the target nucleic acid, and a hole-transfer-inducing agent bound to the probe, wherein a nucleotide region corresponding to the target nucleotide region is located between the hole-transfer-inducing-agent-binding site and the electrode-binding end of the probe. A state of the target nucleotide region in the target nucleic acid can be identified by comparing electrochemical signal levels by energy-induced hole transfers before and after the hybridization of such a probe unit with the target nucleic acid.

  一种用于识别靶核酸中靶核苷酸区的探针单元，该单元具有一个电极、一个与电极结合并能识别靶核酸的探针和一个与探针结合的空穴转移诱导剂，其中与靶核苷酸区相对应的核苷酸区位于空穴转移诱导剂结合位点和探针的电极结合端之间。通过比较这种探针单元与目标核酸杂交前后的能量诱导空穴转移电化学信号水平，可以确定目标核酸中目标核苷酸区的状态。