hydroxymethylrhodamine green

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: hydroxymethylrhodamine green
• 英文别名: HMRG；spiro[1H-2-benzofuran-3,9'-xanthene]-3',6'-diamine
• 化学式: C₂₀H₁₆N₂O₂
• 分子量: 316.359
• InChiKey: ALPRHLCJLWIKCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  70.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-甲基-3-(2,4,5-三甲基-3,6-二氧代环己-1,4-二烯-1-基)丁酸 、 hydroxymethylrhodamine green 在 吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 25.5h， 以27%的产率得到
  参考文献：
  名称：

  Efficacious fluorescence turn-on probe for high-contrast imaging of human cells overexpressing quinone reductase activity

  摘要：

  接通底物探针由氧化还原酶激活，以前所未有的正信号-负背景比提供癌细胞荧光图像。

  DOI：

  10.1039/c6cc08306d
• 作为产物：
  描述：

  在 谷胱甘肽 作用下， 以 aq. phosphate buffer 为溶剂， 生成 hydroxymethylrhodamine green
  参考文献：
  名称：

  A highly sensitive, cell-membrane-permeable fluorescent probe for glutathione

  摘要：

  Glutathione (GSH) is a primary intracellular antioxidant. Here, we developed a novel, highly sensitive fluorescent probe for GSH, designated DNs-HMRG, whose fluorescence is regulated by two distinct switching mechanisms, intramolecular spirocyclization and photo-induced electron transfer (PeT). DNs-HMRG showed good cell permeability, and a rapid increase in fluorescence intensity was observed when it was applied to living cells. Further, taking advantage of the fact that the intracellular GSH level in tumor tissue is higher than that in normal tissue, we employed this probe for rapid (within a few tens of seconds) in vivo detection of tiny tumor nodules (less than 1 mm in diameter) in tumor-bearing mice. This probe is expected be a powerful tool in various biological applications, especially studies on redox status. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.08.033

文献信息

• FLUORESCENT PROBE FOR DETECTING DIPEPTIDYL PEPTIDASE IV
  申请人：The University of Tokyo

  公开号：EP3168288B1

  公开（公告）日：2020-06-03
• Efficacious fluorescence turn-on probe for high-contrast imaging of human cells overexpressing quinone reductase activity
  作者：Quinn A. Best、Bijeta Prasai、Alexandra Rouillere、Amanda E. Johnson、Robin L. McCarley

  DOI：10.1039/c6cc08306d

  日期：——

  A turn-on substrate probe is activated by an oxidoreductase, offering fluorescence images of cancer cells with unprecedented positive signal-to-negative background ratios.

  接通底物探针由氧化还原酶激活，以前所未有的正信号-负背景比提供癌细胞荧光图像。
• A highly sensitive, cell-membrane-permeable fluorescent probe for glutathione
  作者：Masafumi Yoshida、Mako Kamiya、Tatsuya Yamasoba、Yasuteru Urano

  DOI：10.1016/j.bmcl.2014.08.033

  日期：2014.9

  Glutathione (GSH) is a primary intracellular antioxidant. Here, we developed a novel, highly sensitive fluorescent probe for GSH, designated DNs-HMRG, whose fluorescence is regulated by two distinct switching mechanisms, intramolecular spirocyclization and photo-induced electron transfer (PeT). DNs-HMRG showed good cell permeability, and a rapid increase in fluorescence intensity was observed when it was applied to living cells. Further, taking advantage of the fact that the intracellular GSH level in tumor tissue is higher than that in normal tissue, we employed this probe for rapid (within a few tens of seconds) in vivo detection of tiny tumor nodules (less than 1 mm in diameter) in tumor-bearing mice. This probe is expected be a powerful tool in various biological applications, especially studies on redox status. (C) 2014 Elsevier Ltd. All rights reserved.