9-[1-(2,4,5-tricarboxy)phenyl]-6-hydroxy-3H-xanthen-3-one

• 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: 9-[1-(2,4,5-tricarboxy)phenyl]-6-hydroxy-3H-xanthen-3-one
• 英文别名: 5-(6-hydroxy-3-oxo-3H-xanthen-9-yl)benzene,2,4-tricarboxylic acid；5-(3-hydroxy-6-oxoxanthen-9-yl)benzene-1,2,4-tricarboxylic acid
• 化学式: C₂₂H₁₂O₉
• 分子量: 420.332
• InChiKey: WJAXLAKBYHSVBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  158
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  9-[1-(2,4,5-tricarboxy)phenyl]-6-hydroxy-3H-xanthen-3-one 在 一水合肼 作用下， 以 三乙二醇 为溶剂， 反应 2.0h， 以72.7%的产率得到7-(3-Hydroxy-6-oxoxanthen-9-yl)-1,4-dioxo-2,3-dihydrophthalazine-6-carboxylic acid
  参考文献：
  名称：

  [EN] MOLECULAR PROBES FOR CHEMILUMINESCENCE IMAGING AND IN VIVO DETECTION OF TARGET MOLECULES
  [FR] SONDES MOLÉCULAIRES POUR L'IMAGERIE EN CHIMIOLUMINESCENCE ET LA DÉTECTION IN VIVO DE MOLÉCULES CIBLES

  摘要：

  化学发光成像探针用于体内检测生物分子、事件或过程。CLI探针可能包含荧光素分子的一部分和发光素分子的一部分。荧光素分子和发光素分子可能通过非黄色素芳香环连接。CLI探针通常无毒且可溶于PBS等水溶液。CLI探针可用于体内检测特定分子。

  公开号：

  WO2016196359A1
• 作为产物：
  描述：

  均苯四甲酸 在 乙酸酐 、 zinc(II) chloride 作用下， 反应 6.0h， 生成 9-[1-(2,4,5-tricarboxy)phenyl]-6-hydroxy-3H-xanthen-3-one
  参考文献：
  名称：

  [EN] MOLECULAR PROBES FOR CHEMILUMINESCENCE IMAGING AND IN VIVO DETECTION OF TARGET MOLECULES
  [FR] SONDES MOLÉCULAIRES POUR L'IMAGERIE EN CHIMIOLUMINESCENCE ET LA DÉTECTION IN VIVO DE MOLÉCULES CIBLES

  摘要：

  化学发光成像探针用于体内检测生物分子、事件或过程。CLI探针可能包含荧光素分子的一部分和发光素分子的一部分。荧光素分子和发光素分子可能通过非黄色素芳香环连接。CLI探针通常无毒且可溶于PBS等水溶液。CLI探针可用于体内检测特定分子。

  公开号：

  WO2016196359A1

文献信息

• Molecular probes for chemiluminescence imaging and in vivo detection of target molecules
  申请人：ARIZONA BOARD OF REGENTS ON BEHALF OF THE UNIVERSITY OF ARIZONA

  公开号：US10912846B2

  公开（公告）日：2021-02-09

  Chemiluminescence imaging probes for in vivo detection of biological molecules, events, or processes. The CLI probes may feature a portion of a fluorescein molecule and a portion of a luminol molecule. The fluorescein molecule and luminol molecule may be linked by a non-xanthenic aromatic ring. The CLI probes are generally non-toxic and soluble in aqueous solutions such as PBS. The CLI probes may be used to detect specific molecules in vivo.

  用于体内检测生物分子、事件或过程的化学发光成像探针。化学发光成像探针可具有部分荧光素分子和部分发光酚分子。荧光素分子和发光酚分子可以通过一个非呫吨芳香环连接。CLI 探针一般无毒，可溶于 PBS 等水溶液。CLI 探针可用于检测体内的特定分子。
• Rational Principles for Modulating Fluorescence Properties of Fluorescein
  作者：Tasuku Ueno、Yasuteru Urano、Ken-ichi Setsukinai、Hideo Takakusa、Hirotatsu Kojima、Kazuya Kikuchi、Kei Ohkubo、Shunichi Fukuzumi、Tetsuo Nagano

  DOI：10.1021/ja048241k

  日期：2004.11.1

  Rational design strategies based on practical fluorescence modulation mechanisms would enable us to rapidly develop novel fluorescence probes for target molecules. Here, we present a practical and general principle for modulating the fluorescence properties of fluorescein. We hypothesized that (a) the fluorescein molecule can be divided into two moieties, i.e., the xanthene moiety as a fluorophore and the benzene moiety as a fluorescence-controlling moiety, even though there is no obvious linker structure between them, and (b) the fluorescence properties can be modulated via a photoinduced electron transfer (PeT) process from the excited fluorophore to a reducible benzene moiety (donor-excited PeT; d-PeT). To evaluate the relationship between the reduction potential of the benzene moiety and the fluorescence properties, we designed and synthesized various derivatives in which the reduction potential of the benzene moiety was fine tuned by introducing electron-withdrawing groups onto the benzene moiety. Our results clearly show that the fluorescence properties of fluorescein derivatives were indeed finely modulated depending upon the reduction potential of the benzene moiety. This information provides a basis for a practical strategy for rational design of novel functional fluorescence probes.
• MOLECULAR PROBES FOR CHEMILUMINESCENCE IMAGING AND IN VIVO DETECTION OF TARGET MOLECULES
  申请人：THE ARIZONA BOARD OF REGENTS ON BEHALF OF THE UNIVERSITY OF ARIZONA

  公开号：US20180161460A1

  公开（公告）日：2018-06-14

  Chemiluminescence imaging probes for in vivo detection of biological molecules, events, or processes. The CLI probes may feature a portion of a fluorescein molecule and a portion of a luminol molecule. The fluorescein molecule and luminol molecule may be linked by a non-xanthenic aromatic ring. The CLI probes are generally non-toxic and soluble in aqueous solutions such as PBS. The CLI probes may be used to detect specific molecules in vivo.