N3,N3,N7,N7-tetra-n-propyl-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-tetra-n-propyl-3,7-diaminophenothiazin-5-ium iodide
• 英文别名: 3,7-bis(di-n-propylamino)phenothiazin-5-ium iodide；propylene blue；3,7-(tetra-n-propylamino)-phenothiazin-5-ium iodide；[7-(Dipropylamino)phenothiazin-3-ylidene]-dipropylazanium;iodide
• 化学式: C₂₄H₃₄N₃S*I
• 分子量: 523.525
• InChiKey: HQYJIMNXKIPJKN-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  43.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  phenothiazin-5-ylium tetraiodide 、 二正丙胺 以 甲醇 为溶剂， 生成 N3,N3,N7,N7-tetra-n-propyl-3,7-diaminophenothiazin-5-ium iodide
  参考文献：
  名称：

  3，7-二（二正丙胺基）-吩噻嗪-5-鎓碘化物与超声协同抑制肿瘤细胞增殖的应用

  摘要：

  本发明属于医药领域，公开一种3，7‑二(二正丙胺基)‑吩噻嗪‑5‑鎓碘化物(PRB)与超声协同抑制肿瘤细胞增殖的应用。以K562细胞为研究对象，结合低频超声，实验证明PRB与超声协同作用后，能够明显的抑制K562细胞的增殖，为声敏剂的构效关系研究提供有力理论支持，并推动SDT用于抗肿瘤临床。

  公开号：

  CN109350741A

文献信息

• 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.
• 3，7-二（二正丙胺基）-吩噻嗪-5-鎓碘化物与超声协同抑制肿瘤细胞增殖的应用
  申请人：辽宁大学

  公开号：CN109350741A

  公开（公告）日：2019-02-19

  本发明属于医药领域，公开一种3，7‑二(二正丙胺基)‑吩噻嗪‑5‑鎓碘化物(PRB)与超声协同抑制肿瘤细胞增殖的应用。以K562细胞为研究对象，结合低频超声，实验证明PRB与超声协同作用后，能够明显的抑制K562细胞的增殖，为声敏剂的构效关系研究提供有力理论支持，并推动SDT用于抗肿瘤临床。