5,10,15,20-tetrakis[3-(β-D-glucopyranosyloxy)phenyl]porphyrin | 141036-61-5

• 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: 5,10,15,20-tetrakis[3-(β-D-glucopyranosyloxy)phenyl]porphyrin
• CAS: 141036-61-5
• 化学式: C₆₈H₇₀N₄O₂₄
• 分子量: 1327.32
• InChiKey: WPDFEEAQDFNVGL-PFQDEMPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.04
• 重原子数：
  96.0
• 可旋转键数：
  16.0
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  454.88
• 氢给体数：
  18.0
• 氢受体数：
  26.0

反应信息

• 作为产物：
  描述：

  5,10,15,20-tetrakis[3-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)phenyl]porphyrin 在 sodium methylate 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 0.5h， 以83.9%的产率得到5,10,15,20-tetrakis[3-(β-D-glucopyranosyloxy)phenyl]porphyrin
  参考文献：
  名称：

  作为金属离子分光光度试剂的新型水溶性糖基化卟啉的合成和表征

  摘要：

  合成了六种新型水溶性糖基化卟啉（5、10、15、20-四[2-、3-或4-（β-D-吡喃葡萄糖基）苯基]卟啉），并通过1H和13C研究了它们的结构核磁共振。Tetrakis（邻取代苯基）卟啉由四种阻转异构体（αβαβ、ααββ、αααβ 和 αααα）组成，根据 13C NMR 峰分裂模式明确指定。特别值得注意的是，获得了水溶性栅栏卟啉（αααα）。此外，研究了它们作为金属离子显色试剂的特性。高度水溶性葡萄糖的引入成功地改善了迄今为止制备的阴离子或阳离子卟啉的聚集和吸附特性，而其他重要的分析特性没有任何显着变化。

  DOI：

  10.1246/bcsj.67.668

文献信息

• Synthesis and Chromogenic Properties of New Water-Soluble Glycosylated Porphines
  作者：Katsunori Kohata、Yuichi Yamaguchi、Hisao Higashio、Tsugikatsu Odashima、Hajime Ishii

  DOI：10.1246/cl.1992.477

  日期：1992.3

  We synthesized two kinds of new water-soluble glycosylated porphines, 5,10,15,20-tetrakis[4′-(β-d-glucopyranosyl)phenyl]porphine and 5,10,15,20-tetrakis[3′-(β-d-glucopyranosyl)phenyl]porphine, and investigated their chromogenic properties and reactivities with copper(II) ion.

  我们合成了两种新型水溶性糖基化卟吩，即 5,10,15,20-四[4′-（β-d-吡喃葡萄糖基）苯基]卟吩和 5,10,15,20-四[3′-（β-d-吡喃葡萄糖基）苯基]卟吩，并研究了它们的致色性以及与铜（II）离子的反应活性。
• Cellular Uptake and Photocytotoxicity of Glycoconjugated Porphyrins in HeLa Cells¶
  作者：Shiho Hirohara、Makoto Obata、Atsuhiro Saito、Shin-ichi Ogata、Chikara Ohtsuki、Suguru Higashida、Shun-ichiro Ogura、Ichiro Okura、Yuko Sugai、Yuji Mikata、Masao Tanihara、Shigenobu Yano

  DOI：10.1562/2004-03-07-ra-103.1

  日期：——

  Thirty-two glycoconjugated porphyrins were synthesized by a modification of Lindsey method in the presence of Zn(OAc)(2).2H(2)O as a template. The Zn2+ ion template strategy improved the yield about three-fold in the case of meta-substituted tetraphenylporphyrins. In addition, free-base porphyrins were obtained almost quantitatively by demetalation with 4 M HCl. Sixteen deacetylated glycoconjugated porphyrins were tested as candidate photodynamic therapy (PDT) drugs using HeLa cells. Most of the deacetylated glycoconjugated porphyrins showed higher cellular uptake than tetraphenylporphyrin tetrasulfonic acid (TPPS), and 5,10,15, 20-tetrakis[4-(beta-D-arabinopyranosyloxy)phenyl]porphyrin (p-5d) in particular showed 18.5-fold higher uptake than TPPS. The photocytotoxicity of 5,10,15,20-tetrakis[4-(beta-D-glucopyranosyloxy)phenyl]porphyrin (p-5a), p-5d and TPPS was examined with HeLa cells, using a light dose of 16 J/cm(2). These photosensitizers had no cytotoxicity in the dark, but their photocytotoxicity increased in the order of TPPS < p-5a < p-5d. These results suggest p-5d is a good candidate for a PDT drug.