N3,N3,N7,N7-tetra-n-butyl-3,7-diaminophenothiazin-5-ium iodide | 439119-96-7

• 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-tetra-n-butyl-3,7-diaminophenothiazin-5-ium iodide
• 英文别名: 3,7-bis(dibutylamino)-phenothiazin-5-ium iodide；butylene blue；N,N-Dibutyl-7-(dibutylamino)-3H-phenothiazin-3-iminium iodide；dibutyl-[7-(dibutylamino)phenothiazin-3-ylidene]azanium;iodide
• CAS: 439119-96-7
• 化学式: C₂₈H₄₂N₃S*I
• 分子量: 579.632
• InChiKey: MDRSQXOPSFSLIU-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  5.55
• 重原子数：
  33
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 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-tetra-n-butyl-3,7-diaminophenothiazin-5-ium iodide 在 sodium dithionite 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 3-N,3-N,7-N,7-N-tetrabutyl-10H-phenothiazine-3,7-diamine
  参考文献：
  名称：

  用于高对比度可激活成像的自持近红外余辉化学发光体

  摘要：

  mMB作为一种新型自持余辉分子，能够实现光子敏化、化学缺陷形成和余辉产生，具有更高亮度的近红外余辉化学发光和近红外荧光光声信号。通过在吩噻嗪环上引入响应单元，它专为生物标志物的超灵敏成像而设计，具有卓越的激活率，从而实现具有高 SBR 的体内多功能成像。

  DOI：

  10.1002/anie.202318545
• 作为产物：
  描述：

  吩噻嗪 在 碘 作用下， 以88 %的产率得到N3,N3,N7,N7-tetra-n-butyl-3,7-diaminophenothiazin-5-ium iodide
  参考文献：
  名称：

  用于高对比度可激活成像的自持近红外余辉化学发光体

  摘要：

  mMB作为一种新型自持余辉分子，能够实现光子敏化、化学缺陷形成和余辉产生，具有更高亮度的近红外余辉化学发光和近红外荧光光声信号。通过在吩噻嗪环上引入响应单元，它专为生物标志物的超灵敏成像而设计，具有卓越的激活率，从而实现具有高 SBR 的体内多功能成像。

  DOI：

  10.1002/anie.202318545

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。
• 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.
• A Self‐Sustaining Near‐Infrared Afterglow Chemiluminophore for High‐Contrast Activatable Imaging
  作者：Jieli Zhu、Wan Chen、Li Yang、Yuyang Zhang、Baoliang Cheng、Wei Gu、Qing Li、Qingqing Miao

  DOI：10.1002/anie.202318545

  日期：2024.3.11

  enabling photon sensitization, chemical defect formation, and afterglow generation, possessed a NIR afterglow chemiluminescence with a higher brightness and a NIR fluoro-photoacoustic signal. By introducing a responsive unit on the phenothiazine ring, it was tailored for ultrasensitive imaging of biomarkers with a superior activation ratio, enabling in vivo versatile imaging with high SBRs.

  mMB作为一种新型自持余辉分子，能够实现光子敏化、化学缺陷形成和余辉产生，具有更高亮度的近红外余辉化学发光和近红外荧光光声信号。通过在吩噻嗪环上引入响应单元，它专为生物标志物的超灵敏成像而设计，具有卓越的激活率，从而实现具有高 SBR 的体内多功能成像。