N3,N3,N7,N7-tetraethyl-3,7-diaminophenothiazin-5-ium iodide

• 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: N3,N3,N7,N7-tetraethyl-3,7-diaminophenothiazin-5-ium iodide
• 英文别名: ethylene blue；3,7-bis(diethylamino)-phenothiazin-5-ium iodide；ethylthionium iodide；ethyl-thioninium iodide；3,7-Bis(diethylamino)phenothiazin-5-ium iodide；[7-(diethylamino)phenothiazin-3-ylidene]-diethylazanium;iodide
• 化学式: C₂₀H₂₆N₃S*I
• 分子量: 467.417
• InChiKey: PJZLRFOCVIZYGB-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.06
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  43.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N3,N3,N7,N7-tetraethyl-3,7-diaminophenothiazin-5-ium iodide 在 乙醇 、 碘乙烷 作用下， 反应 18.0h， 以40%的产率得到ethylthionium iodide hydrogen iodide
  参考文献：
  名称：

  WO2007/110629

  摘要：

  公开号：
• 作为产物：
  描述：

  N,N-二乙基对苯二胺 在 盐酸 、 manganese(IV) oxide 、 sodium dichromate dihydrate 、 硫酸 、 copper(II) sulfate 、 zinc(II) chloride 作用下， 以 水 为溶剂， 反应 1.5h， 生成 N3,N3,N7,N7-tetraethyl-3,7-diaminophenothiazin-5-ium iodide
  参考文献：
  名称：

  Thioninium compounds and their use

  摘要：

  公开号：

  EP2853293B1

文献信息

• Methylene blue phosphoramidite for DNA labelling
  作者：Gabriel De Crozals、Carole Farre、Monique Sigaud、Philippe Fortgang、Corinne Sanglar、Carole Chaix

  DOI：10.1039/c4cc10164b

  日期：——

  We report the first synthesis of a methylene blue (MB) phosphoramidite derivative suitable for DNA solid-phase synthesis.

  我们报告了第一次合成适用于DNA固相合成的亚甲基蓝（MB）磷酰胺衍生物。
• WO2007/110629
  申请人：——

  公开号：——

  公开（公告）日：——
• A convenient one-pot synthesis of ethylene blue
  作者：Jeremy A. Cody、Christian S. Larrabee、Michael D. Clark、Sofiya Hlynchuk、Jacob A. Tatum

  DOI：10.1016/j.tetlet.2012.07.012

  日期：2012.9

  We have developed an efficient one-pot, two-step preparation of ethylene blue by eliminating aqueous work-ups and cumbersome purification techniques. Our procedure generates ethylene blue in good overall yields of 45-56% with approximately 95% purity, which is uncommon for the synthesis of a phenothiazinium salt. Due to its unique properties, ethylene blue has great potential for a broad range of biological applications and, as a result, an efficient procedure for the synthesis of ethylene blue is critical. (C) 2012 Elsevier Ltd. All rights reserved.
• In Vitro Photodynamic Activity of a Series of Methylene Blue Analogues¶
  作者：Kirste J. Mellish、Russell D. Cox、David I. Vernon、John Griffiths、Stanley B. Brown

  DOI：10.1562/0031-8655(2002)075<0392:ivpaoa>2.0.co;2

  日期：——

  We have synthesized a series of symmetrical phenothiazines in which the methyl groups of methylene blue have been substituted by longer alkyl chains. Intrinsic photosensitizing ability was not altered by increasing the chain length. However, in vitro phototoxicity after 2 h incubation of RIF-1 murine fibrosarcoma cells followed the order n-propyl > n-pentyl > n-butyl > n-hexyl > ethyl > methyl, with ethyl and n-propyl analogues being 14- and 130-fold more phototoxic than methylene blue, respectively. All analogues also had an improved ratio of phototoxicity:dark toxicity (4:1 to 27:1) compared with methylene blue (3:1). Phototoxicity did not correlate with cellular phenothiazine levels, suggesting that the site of subcellular localization may be more important. After 2 h incubation of RIF-1 cells with the phototoxicity LD50 concentration, methylene blue and all analogues were observed to be localized in the lysosomes by fluorescence microscopy. On exposure to light, methylene blue relocalized to the nucleus, the ethyl analogue did not relocalize, whereas the more phototoxic n-propyl - n-hexyl analogues relocalized to the mitochondria. Relocalization to the mitochondria was associated with an octanol: buffer partition coefficient greater than or equal to 1. Therefore, the longer-chain analogues of methylene blue show significantly improved phototoxicity in vitro and, in addition, are expected to avoid the problems of mutagenicity associated with the nuclear localization of methylene blue.
• Thioninium compounds and their use
  申请人：WisTa Laboratories Ltd.

  公开号：EP2853293B1

  公开（公告）日：2017-11-22