bis[3-(4-pyridyl)propan-1-olato]tetraphenylporphyrinatophosphorus(V) chloride | 1507382-76-4

• 英文名称: bis[3-(4-pyridyl)propan-1-olato]tetraphenylporphyrinatophosphorus(V) chloride
• CAS: 1507382-76-4
• 化学式: C₆₀H₄₈N₆O₂P*Cl
• 分子量: 951.507
• InChiKey: OUEWQWOUFMREPC-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  溴己烷 、 bis[3-(4-pyridyl)propan-1-olato]tetraphenylporphyrinatophosphorus(V) chloride 以 乙腈 为溶剂， 反应 24.0h， 以91%的产率得到bis[3-(1-hexyl-4-pyridinio)propan-1-olato]tetraphenylporphyrinatophosphorus(V) dibromide chloride
  参考文献：
  名称：

  Spectroscopic Analysis of the Interaction of Human Serum Albumin with Tricationic Phosphorus Porphyrins Bearing Axial Pyridinio Groups

  摘要：

  人们对水溶性卟啉和金属卟啉作为光动力疗法（PDT）潜在的光敏剂给予了高度关注。因此，通过在磷卟啉的轴向配体上引入N-烷基吡啶锵基团，制备了水溶性三阳离子磷卟啉配合物。所得到的三阳离子磷卟啉容易溶解在水中，不会形成聚集，即使在较高浓度下也是如此。此外，卟啉对人类血清白蛋白（HSA）的亲和力是其在PDT应用中的一个关键因素，因为HSA在药物分子向目标细胞的转运中起着重要作用。通过考察在存在HSA的情况下，磷卟啉溶液的吸收和荧光光谱中Soret带的改变以及三阳离子磷卟啉对HSA的荧光淬灭作用，研究了三阳离子磷卟啉与HSA的相互作用。含适度长烷基链的吡啶锵基团上的三阳离子磷卟啉在HSA的色氨酸残基附近位置强吸附。这一结果表明，含有烷基基团的三阳离子磷卟啉由于其高水溶性和对HSA的高亲和力，是作为PDT试剂的良好候选。

  DOI：

  10.1246/bcsj.20130191
• 作为产物：
  描述：

  4-吡啶丙醇 、 (5,10,15,20-tetraphenylporphinato)dichlorophosphorus(V) chloride 以 乙腈 为溶剂， 反应 24.0h， 以47%的产率得到bis[3-(4-pyridyl)propan-1-olato]tetraphenylporphyrinatophosphorus(V) chloride
  参考文献：
  名称：

  Spectroscopic Analysis of the Interaction of Human Serum Albumin with Tricationic Phosphorus Porphyrins Bearing Axial Pyridinio Groups

  摘要：

  人们对水溶性卟啉和金属卟啉作为光动力疗法（PDT）潜在的光敏剂给予了高度关注。因此，通过在磷卟啉的轴向配体上引入N-烷基吡啶锵基团，制备了水溶性三阳离子磷卟啉配合物。所得到的三阳离子磷卟啉容易溶解在水中，不会形成聚集，即使在较高浓度下也是如此。此外，卟啉对人类血清白蛋白（HSA）的亲和力是其在PDT应用中的一个关键因素，因为HSA在药物分子向目标细胞的转运中起着重要作用。通过考察在存在HSA的情况下，磷卟啉溶液的吸收和荧光光谱中Soret带的改变以及三阳离子磷卟啉对HSA的荧光淬灭作用，研究了三阳离子磷卟啉与HSA的相互作用。含适度长烷基链的吡啶锵基团上的三阳离子磷卟啉在HSA的色氨酸残基附近位置强吸附。这一结果表明，含有烷基基团的三阳离子磷卟啉由于其高水溶性和对HSA的高亲和力，是作为PDT试剂的良好候选。

  DOI：

  10.1246/bcsj.20130191

文献信息

• Additive effect of heparin on the photoinactivation of Escherichia coli using tricationic P-porphyrins
  作者：Jin Matsumoto、Kou Suzuki、Hidekazu Uezono、Kaho Watanabe、Masahide Yasuda

  DOI：10.1016/j.bmcl.2017.10.032

  日期：2017.12

  Polycationic porphyrins have received substantial attention in developing singlet oxygen-sensitizers for biological use such as in the photoinactivation of bacteria and photodynamic therapy (PDT) of tumor cells because they have strong binding affinities for DNA and proteins. However, these strong cellular interactions can retard elimination of the drug after PDT. Therefore, the studies on the interactions of porphyrins with other molecules present much interest, in order to modulate the sensitizers' activity or even remove them from the human body after PDT. Here, we studied the additive effect of heparin on the photoinactivation by polycationic porphyrins using Escherichia coli as a model cell. Tricationic P-porphyrin sensitizers substituted with an N-alkylpyridinium group (alkyl = pentyl (1a), hexyl (1b), and heptyl (1c)) or N-hexylammonium (1d) as the axial ligand were used. Additionally, dicationic Sb-porphyrin substituted with an N-hexylpyridinium group (1e) was prepared. We studied the additive effect of heparin on the photoinactivation of E. coli by 1a-1e. The bactericidal activities were evaluated using the half-life (T1/2 in min) of E. coli and the minimum effective concentrations ([P]) of the porphyrin sensitizers. In the absence of heparin, the [P] values were determined to be 0.4-0.5 lM for 1a-1c and 2.0 mu M for 1d-1e. The bactericidal activity of 1a-1c was completely retarded by the addition of heparin (1.0 mu M). However, the addition of heparin (1.0 mu M) could not completely retard the bactericidal activity of 1d-1e whose [P] values were relatively large. It is suggested that tricationic 1a-1c adsorbed onto the anionic heparin through electrostatic interactions. The adsorption of 1 on heparin disturbs the uptake of 1 into E. coli cells. Thus, the addition of heparin was found to be a useful method for retarding photoinactivation. (C) 2017 Elsevier Ltd. All rights reserved.