phenothiazin-5-ium tetraiodide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: phenothiazin-5-ium tetraiodide
• 英文别名: molecular iodine;phenothiazin-5-ium;iodide
• 化学式: 2C₁₂H₈NS*2I*3I₂
• 分子量: 1411.77
• InChiKey: VBBMPKAEKFMKOP-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.51
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  phenothiazin-5-ium tetraiodide 在 lithium hydroxide monohydrate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 42.0h， 生成 3,7-bis((2-(carboxyl)phenyl)amino)phenothiazin-5-ium chloride
  参考文献：
  名称：

  羧苯基片段官能化吩噻嗪的合成及超分子自组装

  摘要：

  以在近红外范围内具有强吸光度为特征的无毒化合物的分散体在光动力疗法中可用作有效的抗菌剂和抗癌剂。描述了一种制备具有受控形态的纳米颗粒的水分散体的方法。通过将邻氨基苯甲酸甲酯氧化加成到吩噻嗪-5-鎓四碘化物，随后酯基水解，首次合成了含有酯和羧基的 3,7-双(芳基氨基)吩噻嗪-5-鎓衍生物。对于合成的双（羧基）吩噻嗪衍生物，研究了与 3-苯基亚氨基-7-苯基氨基吩噻嗪的关联。获得的 1:1 关联的特征是红移。研究了所得纳米缔合物在甲醇-水体系中的纳米沉淀，

  DOI：

  10.1007/s11172-020-2765-z
• 作为产物：
  描述：

  吩噻嗪 在 碘 作用下， 以 氯仿 为溶剂， 以80%的产率得到phenothiazin-5-ium tetraiodide
  参考文献：
  名称：

  双吩噻嗪鎓光敏剂的合成和DNA相互作用。

  摘要：

  我们报告了N，N-双[（7-二甲基氨基）吩噻嗪-5-基-3-基] -4,4-乙烯二哌啶二碘化物（3）的合成和表征，该二碘化物由两个与中央乙烯二哌啶相连的光敏吩噻嗪鎓环组成链接器。在测试的所有时间点（10、30、60分钟）和所有波长（676、700、710 nm）下，pUC19质粒DNA（22摄氏度和pH 7.0）的光裂解显着增强了1 microM of 3（相比于1） microM的母体吩噻嗪亚甲基蓝（MB）。在吩噻嗪的浓度范围为5至0.5 microM时，化合物3产生的光裂解水平始终高于使用约两倍量的MB产生的裂解（例如710 nm的5 microM 3和10 microM MB裂解）。质粒DNA的产率分别为93％和71％）。清除剂测定法提供了单重态氧和较小程度的羟基自由基参与DNA损伤的证据。以核苷酸分辨率分析光解产物表明，直接的链断裂和碱不稳定的损伤主要发生在鸟嘌呤碱基上。虽然化合物

  DOI：

  10.1039/b810015b

文献信息

• 3,7-Bis(<i>N</i> -methyl-<i>N</i> -phenylamino)phenothiazinium Salt: Improved Synthesis and Aggregation Behavior in Solution
  作者：Martina Tiravia、Federica Sabuzi、Martina Cirulli、Silvia Pezzola、Graziano Di Carmine、Daniel Oscar Cicero、Barbara Floris、Valeria Conte、Pierluca Galloni

  DOI：10.1002/ejoc.201900504

  日期：2019.6.2

  Design and synthesis optimization of 3,7‐bis(N‐methyl‐N‐phenylamino)phenothiazinium chloride is reported. A detailed analysis by DFT calculations, UV/Vis, 1H NMR and electrochemical studies supports that, contrary to methylene blue, aggregation only occurs at concentrations of 1.0 × 10–3 M and higher.

  报道了3,7-双（N-甲基-N-苯基氨基）吩噻嗪氯化物的设计和合成优化。通过DFT计算，UV / Vis，1 H NMR和电化学研究进行的详细分析支持，与亚甲基蓝相反，聚集仅在1.0×10 –3 M或更高的浓度下发生。
• A synthetic route to 3-(dialkylamino)phenothiazin-5-ium salts and 3,7-disubstituted derivatives containing two different amino groups
  作者：Lucjan Strekowski、Dong-Feng Hou、Roman L. Wydra、Raymond F. Schinazi

  DOI：10.1002/jhet.5570300641

  日期：1993.12

  Phenothiazin-5-ium tetraiodide hydrate (2), the suggested oxidation product of phenothiazine with iodine, is treated with two equivalents of a dialkylamine to give 3-(dialkylamino)phenothiazin-5-ium triiodides, 3-6. 3,7-Disubstituted phenothiazin-5-ium iodides, 7-9, are obtained by the reaction of 3-6 with an amine.

  吩噻嗪5碘化四碘化物水合物（2），是吩噻嗪与碘的氧化产物，用两当量的二烷基胺处理，得到3-（二烷基氨基）吩噻嗪5碘化三碘化物3-6。通过3-6与胺的反应获得3，7-二取代的吩噻嗪-5-碘化物碘化物7-9。
• Structure-based optimization of FDA-approved drug methylene blue as a c-myc G-quadruplex DNA stabilizer
  作者：Daniel Shiu-Hin Chan、Hui Yang、Maria Hiu-Tung Kwan、Zhen Cheng、Paul Lee、Li-Ping Bai、Zhi-Hong Jiang、Chun-Yuen Wong、Wang-Fun Fong、Chung-Hang Leung、Dik-Lung Ma

  DOI：10.1016/j.biochi.2011.02.013

  日期：2011.6

  G-quadruplexes are non-canonical DNA secondary structures putatively present in the promoter regions of oncogenes in the human genome. The targeting of promoter G-quadruplex structures to repress oncogene transcription represents a potential anticancer strategy. Here, we have used high-throughput virtual screening to identify FDA-approved drug methylene blue (MB) as a promising scaffold for binding the c-myc oncogene G-quadruplex DNA. Based on molecular docking analysis of MB to the c-myc G-quadruplex, we designed and screened 50 MB derivatives containing side chains that could interact with the G-quadruplex grooves. As a proof-of-concept, the highest-scoring compounds were synthesized and the interactions with the c-myc G-quadruplex were investigated using the FID assay. The results showed that the methylene blue derivatives 6a-c were able to bind to the c-myc G-quadruplex with greater binding affinity compared to the known G-quadruplex binding ligand, crystal violet. The activity of the most potent compound identified from the FID assay, 6b, as an inhibitor for polymerase-drive DNA extension was examined using a PCR-stop assay and compared against that of the parent compound methylene blue. The results of the PCR-stop assay showed that the addition of the side chain improved the activity of the derivatives as an inhibitor compared to the parent compound. The MB derivative 6b was shown to be highly selective towards c-myc G-quadruplex over double-stranded DNA and other cellular biological models, and displayed higher cytoxicity against human hepatocarcinoma cells compared to the parent compound, MB. biologically relevant G-quadruplexes using UV-visible spectroscopy and mass spectrometry, respectively. The MB derivative 6b could induce or stabilize c-myc G-quadruplex formation in both cell-free and (C) 2011 Elsevier Masson SAS. All rights reserved.
• Syntheses and DNA photocleavage by mono- and bis-phenothiazinium–piperazinexylene intercalators
  作者：Beth Wilson、María-José Fernández、Antonio Lorente、Kathryn B. Grant

  DOI：10.1016/j.tet.2008.01.105

  日期：2008.4

  Chromophore systems consisting of one (compound 5) or two (compound 6) phenothiazine rings covalently attached to a bis-piperazinexylene chain were synthesized and evaluated as DNA photocleaving agents. In the presence of DNA, the compounds were shown to monointercalate in their deaggregated forms and to strongly absorb red wavelengths of light. Reactions containing micromolar concentrations of compound produced robust photocleavage of plasmid DNA under near-physiological conditions of temperature and pH (22 degrees C and pH 7.0). Phenothiazines 5 and 6 increased the T-m of calf thymus DNA by 17 and 19 degrees C, indicating that significant levels of duplex stabilization were produced. (c) 2008 Elsevier Ltd. All rights reserved.