9-[1-(2,4,5-trimethoxycarbonyl)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-trimethoxycarbonyl)phenyl]-6-hydroxy-3H-xanthen-3-one
• 英文别名: 5,6-dicarboxyfluorescein trimethylester；Trimethyl 5-(3-hydroxy-6-oxoxanthen-9-yl)benzene-1,2,4-tricarboxylate
• 化学式: C₂₅H₁₈O₉
• 分子量: 462.413
• InChiKey: BDRIEERGKBDGHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  125
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  6-[[[5-(2,4-二氧代嘧啶-1-基)-3,4-二羟基四氢呋喃-2-基]甲氧基-羟基磷酰]氧基-羟基磷酰]氧基-3,4,5-三羟基四氢吡喃-2-羧酸 、 9-[1-(2,4,5-trimethoxycarbonyl)phenyl]-6-hydroxy-3H-xanthen-3-one 在 UDP-glucuronosyltransferase 1A₁ 、 magnesium chloride 、 alamethicin 作用下， 以 二甲基亚砜 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  TokyoGreen derivatives as specific and practical fluorescent probes for UDP-glucuronosyltransferase (UGT) 1A1

  摘要：

  东京绿（TokyoGreen, TG）衍生物被发现是重要的药物代谢酶——尿苷二磷酸葡萄糖醛酸转移酶（UDP-葡萄糖醛酸转移酶 UGT）1A1的高效且特异性底物。通过简单地监测荧光强度的变化，实现了对该酶的快速、特异且敏感的检测。我们还设计并开发了首批针对UGT的“开启型”荧光探针。

  DOI：

  10.1039/c3cc38810g
• 作为产物：
  描述：

  均苯四甲酸二酐 在 甲烷磺酸 、 硫酸 作用下， 反应 20.0h， 生成 9-[1-(2,4,5-trimethoxycarbonyl)phenyl]-6-hydroxy-3H-xanthen-3-one
  参考文献：
  名称：

  Rational Principles for Modulating Fluorescence Properties of Fluorescein

  摘要：

  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.

  DOI：

  10.1021/ja048241k

文献信息

• FLUORESCENT PROBE FOR MEASUREMENT OF GLUCURONATE TRANSFERASE
  申请人：Nagano Tetsuo

  公开号：US20100297681A1

  公开（公告）日：2010-11-25

  A fluorescent probe for measurement of UDP-glucuronosyltransferase, which comprises a fluorescein derivative, wherein in the fluorescein derivative, the 2-carboxy group on the benzene ring of fluorescein is replaced with another monovalent substituent, provided that said substituent is a substituent other than sulfo group, and the substituent does not have carboxy group or sulfo group, and wherein the fluorescein derivative may have an arbitrary substituent at a position on the benzene ring other than the 2-position, and the fluorescein derivative may have a substituent selected from the group consisting of an alkoxy group and a halogen atom at the 2-position and/or the 7-position of fluorescein.
• US8309319B2
  申请人：——

  公开号：US8309319B2

  公开（公告）日：2012-11-13
• TokyoGreen derivatives as specific and practical fluorescent probes for UDP-glucuronosyltransferase (UGT) 1A1
  作者：Takuya Terai、Rie Tomiyasu、Tomoe Ota、Tasuku Ueno、Toru Komatsu、Kenjiro Hanaoka、Yasuteru Urano、Tetsuo Nagano

  DOI：10.1039/c3cc38810g

  日期：——

  TokyoGreen (TG) derivatives were found to be efficient and specific substrates of an important drug-metabolizing enzyme, UDP-glucuronosyltransferase (UGT) 1A1. A rapid, specific, and sensitive assay of the enzyme was achieved simply by monitoring the change in fluorescence intensity. We also designed and developed the first “turn-on” fluorescent probes for UGTs.

  东京绿（TokyoGreen, TG）衍生物被发现是重要的药物代谢酶——尿苷二磷酸葡萄糖醛酸转移酶（UDP-葡萄糖醛酸转移酶 UGT）1A1的高效且特异性底物。通过简单地监测荧光强度的变化，实现了对该酶的快速、特异且敏感的检测。我们还设计并开发了首批针对UGT的“开启型”荧光探针。
• 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.