(2S,3R,4S,5R,6R)-2-[6'-(diethylamino)spiro[1H-2-benzofuran-3,9'-xanthene]-3'-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol | 1326231-95-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4S,5R,6R)-2-[6'-(diethylamino)spiro[1H-2-benzofuran-3,9'-xanthene]-3'-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1326231-95-1
• 化学式: C₃₀H₃₃NO₈
• 分子量: 535.594
• InChiKey: VRHRQQHIKZHMND-QPVVSUSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  39
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  121
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,5R,6R)-2-[6'-(diethylamino)spiro[1H-2-benzofuran-3,9'-xanthene]-3'-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol 在 吡啶 、 β-galactosidase 作用下， 反应 3.0h， 生成 C₂₆H₂₅NO₄
  参考文献：
  名称：

  β-Galactosidase Fluorescence Probe with Improved Cellular Accumulation Based on a Spirocyclized Rhodol Scaffold

  摘要：

  We identified a rhodol bearing a hydroxymethyl group (HMDER) as a suitable scaffold for designing fluorescence probes for various hydrolases. HMDER shows strong fluorescence at physiological pH, but phenolic O-alkylation of HMDER results in a strong preference for the spirocyclic form, which has weak fluorescence. As a proof of concept, we utilized this finding to develop a new fluorescence probe for beta-galactosidase. This probe has favorable characteristics for imaging in biological samples: it has good cellular permeability, and its hydrolysis product is well-retained intracellularly. It could rapidly and clearly visualize beta-galactosidase activity in cultured cells and in Drosophila melanogaster tissue, which has rarely been achieved with previously reported fluorescence probes.

  DOI：

  10.1021/ja204781t
• 作为产物：
  描述：

  2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl bromide 在 sodium methylate 、 caesium carbonate 、 sodium sulfate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 (2S,3R,4S,5R,6R)-2-[6'-(diethylamino)spiro[1H-2-benzofuran-3,9'-xanthene]-3'-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
  参考文献：
  名称：

  β-Galactosidase Fluorescence Probe with Improved Cellular Accumulation Based on a Spirocyclized Rhodol Scaffold

  摘要：

  We identified a rhodol bearing a hydroxymethyl group (HMDER) as a suitable scaffold for designing fluorescence probes for various hydrolases. HMDER shows strong fluorescence at physiological pH, but phenolic O-alkylation of HMDER results in a strong preference for the spirocyclic form, which has weak fluorescence. As a proof of concept, we utilized this finding to develop a new fluorescence probe for beta-galactosidase. This probe has favorable characteristics for imaging in biological samples: it has good cellular permeability, and its hydrolysis product is well-retained intracellularly. It could rapidly and clearly visualize beta-galactosidase activity in cultured cells and in Drosophila melanogaster tissue, which has rarely been achieved with previously reported fluorescence probes.

  DOI：

  10.1021/ja204781t

文献信息

• Detection of<i>LacZ</i>-Positive Cells in Living Tissue with Single-Cell Resolution
  作者：Tomohiro Doura、Mako Kamiya、Fumiaki Obata、Yoshifumi Yamaguchi、Takeshi Y. Hiyama、Takashi Matsuda、Akiyoshi Fukamizu、Masaharu Noda、Masayuki Miura、Yasuteru Urano

  DOI：10.1002/anie.201603328

  日期：2016.8.8

  used as a marker for cells with targeted gene expression or disruption. However, it has been difficult to detect lacZ‐positive cells in living organisms or tissues at single‐cell resolution, limiting the utility of existing lacZ reporters. Herein we present a newly developed fluorogenic β‐galactosidase substrate suitable for labeling live cells in culture, as well as in living tissues. This precisely functionalized

  编码大肠杆菌β-半乳糖苷酶的LacZ基因被广泛用作靶向基因表达或破坏的细胞的标志物。但是，很难以单细胞分辨率检测活生物体或组织中的lacZ阳性细胞，从而限制了现有lacZ的实用性记者。本文中，我们介绍了一种新开发的荧光β-半乳糖苷酶底物，适用于标记培养物中以及活组织中的活细胞。这种经过精确功能化的荧光探针与酶反应后，荧光显着活化，通过将自身锚定在细胞内蛋白质上而保留在细胞内，并提供单细胞分辨率。用该探针标记的神经元保留了自发放电，通过应用在细胞中表达的受体的配体可以增强自发放电，这表明该探针可用于研究目标组织在生物组织和生物体中的功能。
• β-Galactosidase Fluorescence Probe with Improved Cellular Accumulation Based on a Spirocyclized Rhodol Scaffold
  作者：Mako Kamiya、Daisuke Asanuma、Erina Kuranaga、Asuka Takeishi、Masayo Sakabe、Masayuki Miura、Tetsuo Nagano、Yasuteru Urano

  DOI：10.1021/ja204781t

  日期：2011.8.24

  We identified a rhodol bearing a hydroxymethyl group (HMDER) as a suitable scaffold for designing fluorescence probes for various hydrolases. HMDER shows strong fluorescence at physiological pH, but phenolic O-alkylation of HMDER results in a strong preference for the spirocyclic form, which has weak fluorescence. As a proof of concept, we utilized this finding to develop a new fluorescence probe for beta-galactosidase. This probe has favorable characteristics for imaging in biological samples: it has good cellular permeability, and its hydrolysis product is well-retained intracellularly. It could rapidly and clearly visualize beta-galactosidase activity in cultured cells and in Drosophila melanogaster tissue, which has rarely been achieved with previously reported fluorescence probes.