[(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3-[(3',6'-dihydroxy-3-oxospiro[2-benzofuran-1,9'-xanthene]-5-yl)carbamothioyloxy]-4,5-dihydroxybenzoate | 1093758-49-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: [(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3-[(3',6'-dihydroxy-3-oxospiro[2-benzofuran-1,9'-xanthene]-5-yl)carbamothioyloxy]-4,5-dihydroxybenzoate
• CAS: 1093758-49-6
• 化学式: C₄₃H₂₉NO₁₆S
• 分子量: 847.766
• InChiKey: LYXWSVGUZJAPQO-AEGYFVCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  61
• 可旋转键数：
  7
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  307
• 氢给体数：
  10
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  异硫氰酸荧光素酯 、 (-)-表没食子儿茶素没食子酸酯 反应 72.0h， 生成 [(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3-[(3',6'-dihydroxy-3-oxospiro[2-benzofuran-1,9'-xanthene]-5-yl)carbamothioyloxy]-4,5-dihydroxybenzoate
  参考文献：
  名称：

  Time-dependent intracellular trafficking of FITC-conjugated epigallocatechin-3-O-gallate in L-929 cells

  摘要：

  Many in vitro studies about green tea polyphenol, (-)-epigallocatechin-3-O-gallate (EGCG) focused on its pro-apoptotic and anti-proliferative effects on various types of cancer cells, while less attention has been paid to its incorporation into the cytoplasm and nuclear translocation. This study concentrated on the time-dependent intracellular trafficking of EGCG in L-929 cells. EGCG was conjugated with fluorescein-4-isothiocyanate (FITC) via the 3 ''-OH or 5 ''-OH group, as confirmed by NMR analysis, and then treated to either suspended or cultured cells. Confocal microscopic observations revealed that FITC-EGCG was clearly seen onto the membrane of suspended cells as well as into the cytoplasm and nucleus within 1 h. As an increase in treatment time, it concentrated on the nucleus and then was located at any places of the cells. The cellular uptake of FITC-EGCG in cultured cells was not observed until 1 h of culture, but started to be observed after at least 2 h. These results imply that although the cellular sensitivity and response to EGCG would be different from those of FITC-EGCG, it would be incorporated into the cytoplasm of cells and further be translocated into the nucleus in a time-dependent manner. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.10.009

文献信息

• Time-dependent intracellular trafficking of FITC-conjugated epigallocatechin-3-O-gallate in L-929 cells
  作者：Dong-Wook Han、Kazuaki Matsumura、Bongju Kim、Suong-Hyu Hyon

  DOI：10.1016/j.bmc.2008.10.009

  日期：2008.11

  Many in vitro studies about green tea polyphenol, (-)-epigallocatechin-3-O-gallate (EGCG) focused on its pro-apoptotic and anti-proliferative effects on various types of cancer cells, while less attention has been paid to its incorporation into the cytoplasm and nuclear translocation. This study concentrated on the time-dependent intracellular trafficking of EGCG in L-929 cells. EGCG was conjugated with fluorescein-4-isothiocyanate (FITC) via the 3 ''-OH or 5 ''-OH group, as confirmed by NMR analysis, and then treated to either suspended or cultured cells. Confocal microscopic observations revealed that FITC-EGCG was clearly seen onto the membrane of suspended cells as well as into the cytoplasm and nucleus within 1 h. As an increase in treatment time, it concentrated on the nucleus and then was located at any places of the cells. The cellular uptake of FITC-EGCG in cultured cells was not observed until 1 h of culture, but started to be observed after at least 2 h. These results imply that although the cellular sensitivity and response to EGCG would be different from those of FITC-EGCG, it would be incorporated into the cytoplasm of cells and further be translocated into the nucleus in a time-dependent manner. (C) 2008 Elsevier Ltd. All rights reserved.