10-(dimethylamino)-3-phenylmethoxy-spiro[7hbenzo[c]xanthene-7,1'(3'H)-isobenzofuran]-3'-one | 1194732-80-3

• 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: 10-(dimethylamino)-3-phenylmethoxy-spiro[7hbenzo[c]xanthene-7,1'(3'H)-isobenzofuran]-3'-one
• 英文别名: 10'-(Dimethylamino)-3'-phenylmethoxyspiro[2-benzofuran-3,7'-benzo[c]xanthene]-1-one；10'-(dimethylamino)-3'-phenylmethoxyspiro[2-benzofuran-3,7'-benzo[c]xanthene]-1-one
• CAS: 1194732-80-3
• 化学式: C₃₃H₂₅NO₄
• 分子量: 499.566
• InChiKey: SJFADCSTOBRZML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  38
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  10-(dimethylamino)-3-hydroxy-spiro[7H-benzo[c]xanthene-7,1'(3'H)-isobenzofuran]-3'-one 、 溴甲苯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 以76%的产率得到10-(dimethylamino)-3-phenylmethoxy-spiro[7hbenzo[c]xanthene-7,1'(3'H)-isobenzofuran]-3'-one
  参考文献：
  名称：

  Design of a bioreductively-activated fluorescent pH probe for tumor hypoxia imaging

  摘要：

  We have designed and evaluated UTX-12 as a novel fluorescent pH probe for tumor hypoxia imaging. UTX-12 consists of a p-nitro benzyl moiety, which is a latent hypoxia-selective leaving group activated by nitro reduction, directly linked to SNARF. Although UTX-12 itself is colorless and non-fluorescent in aqueous solution, nitro reduction triggers the release of SNARF which has well-characterized long wavelength absorption and fluorescence that is sensitive to pH. The resultant SNARF, released intracellularly by enzymatic reduction of UTX-12, allows measurement of pH by pH-dependent dual emission shifts. UTX-12 showed clear differences in fluorescence behavior between hypoxic and aerobic conditions in liver microsomes and inside V79 cells. These data are confirmation that UTX-12 is biologically reduced inside tumor cells and the released SNARF should monitor intracellular pH of tumor cells selectively with reduced background signal. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.08.037

文献信息

• Design of a bioreductively-activated fluorescent pH probe for tumor hypoxia imaging
  作者：Eiji Nakata、Yoshihiro Yukimachi、Hirokazu Kariyazono、Seongwang Im、Chiaki Abe、Yoshihiro Uto、Hiroshi Maezawa、Toshihiro Hashimoto、Yasuko Okamoto、Hitoshi Hori

  DOI：10.1016/j.bmc.2009.08.037

  日期：2009.10

  We have designed and evaluated UTX-12 as a novel fluorescent pH probe for tumor hypoxia imaging. UTX-12 consists of a p-nitro benzyl moiety, which is a latent hypoxia-selective leaving group activated by nitro reduction, directly linked to SNARF. Although UTX-12 itself is colorless and non-fluorescent in aqueous solution, nitro reduction triggers the release of SNARF which has well-characterized long wavelength absorption and fluorescence that is sensitive to pH. The resultant SNARF, released intracellularly by enzymatic reduction of UTX-12, allows measurement of pH by pH-dependent dual emission shifts. UTX-12 showed clear differences in fluorescence behavior between hypoxic and aerobic conditions in liver microsomes and inside V79 cells. These data are confirmation that UTX-12 is biologically reduced inside tumor cells and the released SNARF should monitor intracellular pH of tumor cells selectively with reduced background signal. (C) 2009 Elsevier Ltd. All rights reserved.