5,10,15,20-tetrakis(4-β-D-glucosylphenyl)porphyrin | 141036-60-4

• 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(4-β-D-glucosylphenyl)porphyrin
• 英文别名: 5,10,15,20-tetrakis[4-(β-D-glucopyranosyloxy)phenyl]porphyrin；5,10,15,20-tetra-(para-O-β-D-glucopyranosyloxyphenyl)porphyrin；5,10,15,20-tetrakis(4-β-D-glucosyl)porphyrin；5,10,15,20-tetrakis[3-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)phenyl]porphyrin
• CAS: 141036-60-4
• 化学式: C₆₈H₇₀N₄O₂₄
• 分子量: 1327.32
• InChiKey: PNGPVTMRCRBVJB-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-tetra<4-(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， 生成 5,10,15,20-tetrakis(4-β-D-glucosylphenyl)porphyrin
  参考文献：
  名称：

  Synthesis and Chromogenic Properties of New Water-Soluble Glycosylated Porphines

  摘要：

  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。

  DOI：

  10.1246/cl.1992.477

文献信息

• Synthesis and Characterization of New Style of Water-Soluble Glycosylated Porphyrins as a Spectrophotometric Reagent for Metal Ions
  作者：Katsunori Kohata、Hisao Higashio、Yuichi Yamaguchi、Mamoru Koketsu、Tsugikatsu Odashima

  DOI：10.1246/bcsj.67.668

  日期：1994.3

  Six new styles of water-soluble glycosylated porphyrins (5, 10, 15, 20-tetrakis[2-, 3- or 4-(β-D-glucopyranosyl)phenyl]porphine) were synthesized and studied concerning their structures by 1H and 13C NMR. Tetrakis (o-substituted phenyl)porphine, consisting of four atropisomers (αβαβ, ααββ, αααβ, and αααα), was clearly assigned based on the 13C NMR peak-splitting pattern. It was especially noteworthy

  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。
• [EN] SPECIFICALLY GLYCO-SUBSTITUTED PORPHYRINS AND CHLORINS FOR PHOTODYNAMIC THERAPY<br/>[FR] PORPHYRINES ET CHLORINES GLYCO-SUBSTITUÉES DE FAÇON SPÉCIFIQUE POUR UNE THÉRAPIE PHOTODYNAMIQUE
  申请人：UNIV HAMBURG

  公开号：WO2020120474A1

  公开（公告）日：2020-06-18

  The present invention provides certain tetrapyrrolic compounds having a structure of Formula (1), (2), or (3) wherein B is (I), (II) (III) or (IV), O-R1 is a substituent in the meta or para position of the phenyl ring, R1 is a glyco-substituent derived from a mono-, di-, or trisaccharide group, and each R2 is independently selected from the group consisting of a linear or branched (fluoro-)alkyl group with 3 to 8 carbon atoms, phenyl, pentafluorophenyl, 3,5-bis(trifluoromethyl)phenyl, 4-(1'-thio-β-D-glucosyl)-2,3,5,6-tetrafluorophenyl, 4-(1'-thio-β- D-galactosyl)-2,3,5,6-tetrafluorophenyl, meta- or para-hydroxyphenyl, meta- or para- carboxyphenyl, and meta- or para-YO-phenyl with Y being a polyethyleneglycol-residue with (CH2CH2O)nCH3 with n = 1-30.

  本发明提供了某些四吡咯化合物，其结构为公式（1），（2）或（3），其中B为（I），（II）（III）或（IV），O-R1是苯环的间位或对位取代基，R1是源自单糖，双糖或三糖基团的糖基取代基，每个R2独立地选择自由基组成的群，所述自由基组成的群包括具有3至8个碳原子的线性或支链（氟）烷基，苯基，五氟苯基，3,5-双（三氟甲基）苯基，4-（1'-硫-β-D-葡萄糖基）-2,3,5,6-四氟苯基，4-（1'-硫-β-D-半乳糖基）-2,3,5,6-四氟苯基，间位或对位羟基苯基，间位或对位羧基苯基，以及Y为聚乙二醇残基的间位或对位YO苯基，其中（CH2CH2O）nCH3，n = 1-30。
• Glycoconjugated Porphyrins. 3. Synthesis of Flat Amphiphilic Mixed meso-(Glycosylated aryl)arylporphyrins and Mixed meso-(Glycosylated aryl)alkylporphyrins Bearing Some Mono- and Disaccharide Groups
  作者：Dalila Oulmi、Philippe Maillard、Jean-Luc Guerquin-Kern、Christiane Huel、Michel Momenteau

  DOI：10.1021/jo00111a013

  日期：1995.3

  p-Acetylglycosylated benzaldehydes react with pyrrole by Lindsey's method to produce a variety of flat glycosylated porphyrins. By the same method a large series of amphiphilic mixed glycosylated arylaryl- and mixed glycosylated arylalkylporphyrins have been synthesized, using pyrrole, p-acetylglycosylated benzaldehyde and aryl aldehyde or alkyl aldehyde as starting materials. Under optimized conditions, the di- or triglycosylated derivatives were principally obtained whereas the formation of meso tetrasubstituted porphyrins is minimized. Deprotection of acetyl glycoside moieties allows us to obtain products with good solubility in neutral aqueous solution and a wide range of amphiphilic character. The structure of these new protected and unprotected compounds in solution was confirmed by H-1 NMR studies.
• 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.