2-amino-5-diethylaminophenylthiosulfuric acid sodium salt | 1182337-22-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-amino-5-diethylaminophenylthiosulfuric acid sodium salt
• 英文别名: sodium 2-amino-5-diethylaminophenylthiosulfuric acid
• CAS: 1182337-22-9
• 化学式: C₁₀H₁₅N₂O₃S₂*Na
• 分子量: 298.362
• InChiKey: ZHZKINJANPWFRG-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.33
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  86.46
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-amino-5-diethylaminophenylthiosulfuric acid sodium salt 、 1-萘胺 在 silver carbonate 、 六氟磷酸钾 、 盐酸 作用下， 以 甲醇 、 乙酸乙酯 、 水 为溶剂， 生成
  参考文献：
  名称：

  一种靶向 I 型光敏剂的内质网，用于对缺氧肿瘤细胞进行有效的光动力治疗

  摘要：

  构建了一种内质网靶向的苯并吩噻嗪类光敏剂NBS-ER，可触发内质网应激并诱导细胞凋亡，同时显着降低暗毒性并提高光毒性指数 (PI)。此外，NBS-ER在 4T1 荷瘤小鼠中表现出优异的光动力治疗效果。

  DOI：

  10.1002/chem.202202680
• 作为产物：
  描述：

  N,N-二乙基对苯二胺 在 potassium dichromate 、 aluminum(III) sulfate 、 sodium thiosulfate 、 zinc(II) chloride 作用下， 以 水 为溶剂， 反应 2.0h， 生成 2-amino-5-diethylaminophenylthiosulfuric acid sodium salt
  参考文献：
  名称：

  Antimicrobial Photodynamic Efficacy of Side-chain Functionalized Benzo[a]phenothiazinium Dyes

  摘要：

  Abstract5‐(Ethylamino)‐9‐diethylaminobenzo[a]phenothiazinium chloride (EtNBS) is a photosensitizer (PS) with broad antimicrobial photodynamic activity. The objective of this study was to determine the antimicrobial photodynamic effect of side chain/end group modifications of EtNBS on two representative bacterial Gram‐type‐specific strains. Two EtNBS derivatives were synthesized, each functionalized with a different side‐chain end‐group, alcohol or carboxylic acid. In solution, both exhibited photochemical properties consistent with those of the EtNBS parent molecule. In vitro photodynamic therapy experiments revealed an initial Gram‐type‐specificity with two representative strains; both derivatives were phototoxic to Staphylococcus aureus 29213 but the carboxylic acid derivative was nontoxic to Escherichia coli 25922. This difference in photodynamic efficacy was not due to a difference in the binding of the two molecules to the bacteria as the amount of both derivatives bound by bacteria was identical. Interestingly, the carboxylic acid derivative produced no fluorescence emission when observed in cultures of E. coli via fluorescence microscopy. These early findings suggest that the addition of small functional groups could achieve Gram‐type‐specific phototoxicity through altering the photodynamic activity of PSs and deserve further exploration in a larger number of representative strains of each Gram type.

  DOI：

  10.1111/j.1751-1097.2008.00403.x

文献信息

• Structure–function relationships of Nile blue (EtNBS) derivatives as antimicrobial photosensitizers
  作者：Daniela Vecchio、Brijesh Bhayana、Liyi Huang、Elisa Carrasco、Conor L. Evans、Michael R. Hamblin

  DOI：10.1016/j.ejmech.2014.01.064

  日期：2014.3

  The benzophenothiazinium dye EtNBS has previously been tested as a photosensitizer to mediate photodynamic therapy (PDT). It has been employed to kill cancer cells and microbial cells in vitro and to treat tumors and infections in vivo. We synthesized a panel of derivatives substituted at the 1-position of the benzene ring with electron donating or electron withdrawing groups (amino, acetamido and nitro) and tested their production of reactive oxygen species (ROS) and light-mediated killing of two species of Gram-positive and two species of Gram-negative bacteria. All three compounds showed lower fluorescence, lower yield of ROS and less microbial killing than parent EtNBS, while the order of activity (nitro > amino > acetamido) showed that an electron withdrawing substituent was better than electron donating. To test the hypothesis that 1-substitution distorts the planar structure of the conjugated rings we compared two compounds substituted with N-ethylpropylsulfonamido either at the 1-position or at the 4-position. The 4-isomer was significantly more photoactive than the 1-isomer. We also prepared an EtNBS derivative with a guanidinium group attached to the 5-amino group. This compound had high activity against Gram-negative bacteria due to the extra positive charge. Cellular uptake of the compounds by the four bacterial species was also measured and broadly correlated with activity. These results provided three separate pieces of structure activity relationship data for antimicrobial photosensitizers based on the EtNBS backbone. (C) 2014 Elsevier Masson SAS. All rights reserved.