(2R,3R,4S,5S,6R)-2-[3-[4-[2-[4-[2-[2,5-dimethoxy-4-[3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyprop-1-ynyl]phenyl]ethynyl]-3-(dimethylamino)phenyl]ethynyl]-2,5-dimethoxyphenyl]prop-2-ynoxy]-6-(hydroxymethyl)oxane-3,4,5-triol | 1609475-91-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R,3R,4S,5S,6R)-2-[3-[4-[2-[4-[2-[2,5-dimethoxy-4-[3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyprop-1-ynyl]phenyl]ethynyl]-3-(dimethylamino)phenyl]ethynyl]-2,5-dimethoxyphenyl]prop-2-ynoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1609475-91-3
• 化学式: C₄₆H₅₁NO₁₆
• 分子量: 873.908
• InChiKey: QWDUPULTVCIXLI-BEDJMWONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  63
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  239
• 氢给体数：
  8
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[3-[4-[2-[4-[2-[2,5-dimethoxy-4-[3-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyprop-1-ynyl]phenyl]ethynyl]-3-(dimethylamino)phenyl]ethynyl]-2,5-dimethoxyphenyl]prop-2-ynoxy]oxan-2-yl]methyl acetate 在 ammonium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 16.0h， 以97%的产率得到(2R,3R,4S,5S,6R)-2-[3-[4-[2-[4-[2-[2,5-dimethoxy-4-[3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyprop-1-ynyl]phenyl]ethynyl]-3-(dimethylamino)phenyl]ethynyl]-2,5-dimethoxyphenyl]prop-2-ynoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
  参考文献：
  名称：

  Glucose-functionalized amino-OPEs as biocompatible photosensitizers in PDT

  摘要：

  Photodynamic therapy (PDT) is a minimally invasive procedure that can provide a selective eradication of neoplastic diseases by the combined effect of a photosensitizer, light and oxygen. New amino oligo(phenylene-ethynylene)s (OPEs), bearing hydrophilic glucoside terminations, have been prepared, characterized and tested as photosensitizers in PDT. The effectiveness of these compounds in combination with UVA light has been checked on two tumor cell lines (HEp-2 and HeLa cells, derived from a larynx carcinoma and a cervical carcinoma, respectively). The compounds triggered a mitotic blockage that led to the cell death, being the effect active up to 3 mu m concentration. The photophysical properties of OPEs, such as high quantum yield, stability, singlet oxygen production, biocompatibility, easy cell internalization and very good response even at low concentration, make them promising photosensitizers in the application of PDT. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.01.041

文献信息

• Oligo(phenylene ethynylene) Glucosides: Modulation of Cellular Uptake Capacity Preserving Light ON
  作者：Anna Barattucci、Elisa Deni、Paola Bonaccorsi、Maria Grazia Ceraolo、Teresa Papalia、Antonio Santoro、Maria Teresa Sciortino、Fausto Puntoriero

  DOI：10.1021/jo500661u

  日期：2014.6.6

  A new family of oligo(phenylene ethynylene) (OPE) glucosides has been prepared and characterized. Our results demonstrate that fine-tuning of their photophysical properties can be obtained by acting on the electronics of the core and molecular skeleton. Modulation of the hydrophobic chain length and substituents on the central moieties influences the bioaffinity too. In particular, introducing a NMe2 group on the aromatic central core affords a highly efficient biocompatible fluorescent probe that can be taken up in cytoplasmic vesicles of HEp-2 cells (cells from epidermoid carcinoma larynx tissue). The photophysical behavior, high quantum yield, and stability open the way to the use of the OPE family as stains for cellular imaging analysis by fluorescence microscopy.