[4-[methyl-[3-methyl-3-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanoyl]amino]phenyl]methyl N-(2-butyl-1,3-dioxobenzo[de]isoquinolin-6-yl)carbamate | 1609626-97-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: [4-[methyl-[3-methyl-3-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanoyl]amino]phenyl]methyl N-(2-butyl-1,3-dioxobenzo[de]isoquinolin-6-yl)carbamate
• CAS: 1609626-97-2
• 化学式: C₃₉H₄₁N₃O₇
• 分子量: 663.77
• InChiKey: AELAJSXCTALKQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  49
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [4-[methyl-[3-methyl-3-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanoyl]amino]phenyl]methyl N-(2-butyl-1,3-dioxobenzo[de]isoquinolin-6-yl)carbamate 在 sodium dithionite 作用下， 生成 N-butyl-4-amino-1,8-naphthalimide
  参考文献：
  名称：

  Detection and Cellular Imaging of Human Cancer Enzyme Using a Turn-On, Wavelength-Shiftable, Self-Immolative Profluorophore

  摘要：

  A frontier area in the development of activatable (turn-on) fluorescence-based probes is that concerned with rapid and selective stimulus triggering of probe activation so as to allow for biomarker identification and cellular imaging. The work here is concerned with a cloaked fluorophore composed of a reporter whose fluorescence is efficiently quenched by it being bound to an activatable trigger group through a novel self-immolative linker. Highly selective and rapid activation of the trigger group is achieved by chemical and enzymatic means that result in activated trigger group detachment from the self-immolative linker, with the latter subsequently cleaved from the reporter autonomously, thereby unmasking intense, red-shifted fluorescence emission. To achieve this success, we used a trimethyl-locked quinone propionic acid trigger group and an N-methyl-p-aminobenzyl alcohol self-immolative linker attached to the reporter. Delineated here are the synthesis and characterization of this cloaked fluorophore and the evaluation of its triggered turning on in the presence of an up-regulated enzyme in human cancer cells, NAD(P)-H:quinone oxidoreductase-1 (NQO1, DT-diaphorase, EC 1.6.99.2).

  DOI：

  10.1021/ja5030707
• 作为产物：
  描述：

  [4-(甲基氨基)苯基]甲醇 在 N-甲基吗啉 、 咪唑 、 四丁基氟化铵 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 8.0h， 生成 [4-[methyl-[3-methyl-3-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanoyl]amino]phenyl]methyl N-(2-butyl-1,3-dioxobenzo[de]isoquinolin-6-yl)carbamate
  参考文献：
  名称：

  Detection and Cellular Imaging of Human Cancer Enzyme Using a Turn-On, Wavelength-Shiftable, Self-Immolative Profluorophore

  摘要：

  A frontier area in the development of activatable (turn-on) fluorescence-based probes is that concerned with rapid and selective stimulus triggering of probe activation so as to allow for biomarker identification and cellular imaging. The work here is concerned with a cloaked fluorophore composed of a reporter whose fluorescence is efficiently quenched by it being bound to an activatable trigger group through a novel self-immolative linker. Highly selective and rapid activation of the trigger group is achieved by chemical and enzymatic means that result in activated trigger group detachment from the self-immolative linker, with the latter subsequently cleaved from the reporter autonomously, thereby unmasking intense, red-shifted fluorescence emission. To achieve this success, we used a trimethyl-locked quinone propionic acid trigger group and an N-methyl-p-aminobenzyl alcohol self-immolative linker attached to the reporter. Delineated here are the synthesis and characterization of this cloaked fluorophore and the evaluation of its triggered turning on in the presence of an up-regulated enzyme in human cancer cells, NAD(P)-H:quinone oxidoreductase-1 (NQO1, DT-diaphorase, EC 1.6.99.2).

  DOI：

  10.1021/ja5030707

文献信息

• HNQO1-ACTIVATABLE FLUORESCENT PROBE FOR IMAGING CANCER CELLS IN-VITRO AND IN-VIVO
  申请人：Texas Tech University System

  公开号：US20210154330A1

  公开（公告）日：2021-05-27

  The present invention includes a probe, an assay, a method of detecting, a human NAD(P)H quinone oxidoreductase-1 (hNQO1) enzyme activity with a fluorescent probe comprising a quinone propionic acid (QPA) conjugated to dicyanoisophorone (DCP), wherein the hNQO1 reduces the probe to releases a fluorescent DCP, and a method of making the same.

  本发明包括一种探针、一种测定、一种检测方法，用于检测人NAD(P)H喹啉喹酮氧化还原酶-1（hNQO1）酶活性，所述探针包括将喹酮丙酸（QPA）共轭到二氰异光酮（DCP）的荧光探针，其中hNQO1将探针还原以释放荧光DCP，以及一种制备方法。