3,3'-<(8RS)-8-(1-Hydroxyheptyl)-2,7,12,18-tetramethyl-21H,23H-porphyrin-13,17-diyl>dipropionsaeure-dimethylester | 138629-26-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四吡咯及其衍生物
• 英文名称: 3,3'-<(8RS)-8-(1-Hydroxyheptyl)-2,7,12,18-tetramethyl-21H,23H-porphyrin-13,17-diyl>dipropionsaeure-dimethylester
• 英文别名: 3,3'-[(8RS)-8-(1-Hydroxyheptyl)-2,7,12,18-tetramethyl-21H,23H-porphyrin-13,17-diyl]dipropionsaeure-dimethylester
• CAS: 138629-26-2
• 化学式: C₃₉H₄₈N₄O₅
• 分子量: 652.834
• InChiKey: WWHZNPSJRAOBQV-PHJFJQTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.18
• 重原子数：
  48.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  130.19
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3,3'-<(8RS)-8-(1-Hydroxyheptyl)-2,7,12,18-tetramethyl-21H,23H-porphyrin-13,17-diyl>dipropionsaeure-dimethylester 在 palladium on activated charcoal MS 3 Angstroem 、 氢气 作用下， 以 甲醇 、 邻二甲苯 为溶剂， 25.0~160.0 ℃ 、170.0 kPa 条件下， 反应 2.5h， 生成 3,3'<(cis-7RS,8SR)-(+/-)-7-(dimethylcarbamoylmethyl)-8-heptyl-2,7,12,18-tetramethyl-7,8-dihydro-21H,23H-porphyrin-13,17-diyl>dipropionic acid dimethyl ester
  参考文献：
  名称：

  Haake, Gerold; Meier, Axel; Montforts, Franz-Peter, Liebigs Annalen der Chemie, 1992, # 4, p. 325 - 336

  摘要：

  DOI：
• 作为产物：
  描述：

  3,3'-<8-Formyl-2,7,12,18-tetramethylporphyrin-13,17-diyl>-21H,23H-dipropionsaeure-dimethylester 在 氢溴酸 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 41.67h， 生成 3,3'-<(8RS)-8-(1-Hydroxyheptyl)-2,7,12,18-tetramethyl-21H,23H-porphyrin-13,17-diyl>dipropionsaeure-dimethylester
  参考文献：
  名称：

  一种改进的制备甲型十氢卟啉的方法-生物学上相关的卟啉的合成

  摘要：

  通过在三氟乙酸中将易得的氘卟啉二甲基酯1与原甲酸三甲酯在三氟乙酸中甲酰化并随后进行色谱分离，可以高产率地制备纯的3和8个甲酰基氘卟啉二甲基酯异构体3a，b。甲酰基卟啉可以转化为合成和生物学上有用的衍生物。

  DOI：

  10.1016/0040-4039(91)80810-s

文献信息

• Spectroscopic and biological studies of a novel synthetic chlorin derivative with prospects for use in PDT
  作者：Agnieszka Szurko、Marzena Rams、Aleksander Sochanik、Karolina Sieroń-Stołtny、Agnieszka Maria Kozielec、Franz-Peter Montforts、Roman Wrzalik、Alicja Ratuszna

  DOI：10.1016/j.bmc.2009.10.029

  日期：2009.12.15

  Photosensitizers with desirable combinations of chemical, photophysical and biological properties are essential for improving the efficacy of photodynamic therapy (PDT) against various cancers. Chlorins seem to be promising candidates for photodynamic therapy (PDT) owing to their photophysical properties. This paper reports spectroscopic and biological properties of a novel synthetic chlorin derivative. Cytotoxicity, phototoxicity as well as subcellular localization of the novel derivative was studied using Lewis lung carcinoma cultured cells (LLC). In the examined concentration range no significant cytotoxic effects were found but high phototoxicity was observed. Confocal laser scanning microscopy demonstrated that the compound, upon entering cells, was localized in the perinuclear cytoplasm of LLC cells. Using fluorescent microscopy we investigated the impact of PDT based on the novel compound upon cytoskeleton and DNA structure of LLC cells. Our results indicate that liposomes are effective in transferring the chlorin photosensitizer into the studied cells, leading to their high photosensitization, whereas the non-carrier delivery mode (i.e., DMSO) is rather useless for such purposes. (C) 2009 Elsevier Ltd. All rights reserved.