2-((2'-hydroxyethyl)disulfanyl)ethyl (2''-butyl-1'',3''-dioxo-2'',3''-dihydro-1H-benzo[de]isoquinolin-6''-yl)carbamate | 1353569-60-4

• 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: 2-((2'-hydroxyethyl)disulfanyl)ethyl (2''-butyl-1'',3''-dioxo-2'',3''-dihydro-1H-benzo[de]isoquinolin-6''-yl)carbamate
• 英文别名: 2-(2-hydroxyethyldisulfanyl)ethyl N-(2-butyl-1,3-dioxobenzo[de]isoquinolin-6-yl)carbamate
• CAS: 1353569-60-4
• 化学式: C₂₁H₂₄N₂O₅S₂
• 分子量: 448.564
• InChiKey: STYJYIAGGCFZBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  147
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-((2'-hydroxyethyl)disulfanyl)ethyl (2''-butyl-1'',3''-dioxo-2'',3''-dihydro-1H-benzo[de]isoquinolin-6''-yl)carbamate 在 三乙胺 作用下， 以 四氢呋喃 、 aq. phosphate buffer 、 乙腈 为溶剂， 反应 17.0h， 生成 2-[2-[(2-butyl-1,3-dioxobenzo[de]isoquinolin-6-yl)carbamoyloxy]ethyldisulfanyl]ethyl N-[5-[[4-[5-[[4-[5-[acetyl(hydroxy)amino]pentylamino]-4-oxobutanoyl]-hydroxyamino]pentylamino]-4-oxobutanoyl]-hydroxyamino]pentyl]carbamate
  参考文献：
  名称：

  Development of a novel fluorescence probe capable of assessing the cytoplasmic entry of siderophore-based conjugates

  摘要：

  一种新型荧光探针被合成，能够评估基于铁载体的共轭物进入细胞质的能力，并通过光化学特性和基于细胞的实验进行评估。

  DOI：

  10.1039/c4ob01810a
• 作为产物：
  描述：

  N-butyl-4-nitro-1,8-naphthalimide 在 palladium 10% on activated carbon 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 49.0h， 生成 2-((2'-hydroxyethyl)disulfanyl)ethyl (2''-butyl-1'',3''-dioxo-2'',3''-dihydro-1H-benzo[de]isoquinolin-6''-yl)carbamate
  参考文献：
  名称：

  Thiol-inducible direct fluorescence monitoring of drug release

  摘要：

  一种新型双功能化合物NCC，在细胞内通过硫醇介导的二硫键断裂后，在细胞质中产生红移的荧光发射，并释放出活性DNA烷化剂CLB至细胞核内，最终导致DNA损伤和细胞死亡。

  DOI：

  10.1039/c2ob26680f

文献信息

• Diagnostic devices with modifiable hydrophobic surfaces
  申请人：Siemens Healthcare Diagnostics Inc.

  公开号：US10449536B2

  公开（公告）日：2019-10-22

  A diagnostic device 10 for screening for a target analyte in a sample is provided. The diagnostic device 10 comprises a substrate 12 and a hydrophobic material 20 disposed on the substrate. The hydrophobic material 20 is selected to be converted from the hydrophobic material 20 to a hydrophilic material 22 upon contact with a conversion component within or derived from a sample introduced to the device 10.

  提供了一种用于筛查样品中目标分析物的诊断装置 10。诊断设备 10 包括基底 12 和基底上的疏水材料 20。疏水材料 20 被选择为在与引入装置 10 的样品内或样品中的转换成分接触时，从疏水材料 20 转换为亲水材料 22。
• Hepatocyte-Targeting Single Galactose-Appended Naphthalimide: A Tool for Intracellular Thiol Imaging in Vivo
  作者：Min Hee Lee、Ji Hye Han、Pil-Seung Kwon、Sankarprasad Bhuniya、Jin Young Kim、Jonathan L. Sessler、Chulhun Kang、Jong Seung Kim

  DOI：10.1021/ja210065g

  日期：2012.1.18

  We present the design, synthesis, spectroscopic properties, and biological evaluation of a single galactose-appended naphthalimide (1). Probe 1 is a multifunctional molecule that incorporates a thiol-specific cleavable disulfide bond, a masked phthalamide fluorophore, and a single galactose moiety as a hepatocyte-targeting unit. It constitutes a new type of targetable ligand for hepatic thiol imaging in living cells and animals. Confocal microscopic imaging experiments reveal that 1, but not the galactose-free control system 2, is preferentially taken up by HepG2 cells through galactose-targeted, ASGP-R-mediated endocytosis. Probe 1 displays a fluorescence emission feature at 540 nm that is induced by exposure to free endogenous thiols, most notably GSH. The liver-specificity of 1 was confirmed in vivo via use of a rat model. The potential utility of this probe in indicating pathogenic states and as a possible screening tool for agents that can manipulate oxidative stress was demonstrated in experiments wherein palmitate was used to induce lipotoxicity in HepG2 cells.
• DIAGNOSTIC DEVICES WITH MODIFIABLE HYDROPHOBIC SURFACES
  申请人：Siemens Healthcare Diagnostics Inc.

  公开号：US20170246627A1

  公开（公告）日：2017-08-31

  A diagnostic device 10 for screening for a target analyte in a sample is provided. The diagnostic device 10 comprises a substrate 12 and a hydrophobic material 20 disposed on the substrate. The hydrophobic material 20 is selected to be converted from the hydrophobic material 20 to a hydrophilic material 22 upon contact with a conversion component within or derived from a sample introduced to the device 10.