4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyloxy)isophthalaldehyde | 1312698-60-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyloxy)isophthalaldehyde
• 英文别名: 4-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl)benzyl)oxy)benzene-1,3-dicarbaldehyde；4-[[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methoxy]benzene-1,3-dicarbaldehyde；4-[[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methoxy]benzene-1,3-dicarbaldehyde
• CAS: 1312698-60-4
• 化学式: C₂₁H₂₃BO₅
• 分子量: 366.222
• InChiKey: LYVKWOMGMLXRFY-UHFFFAOYSA-N

物化性质

• 沸点：
  537.0±50.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.19
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyloxy)isophthalaldehyde 在 双氧水 、 sodium acetate 作用下， 以 乙酸酐 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  [EN] ACTIVATABLE FLUOROGENIC COMPOUNDS AND USES THEREOF AS NEAR INFRARED PROBES
  [FR] COMPOSÉS FLUOROGÉNIQUES ACTIVABLES ET LEURS UTILISATIONS EN TANT QUE SONDES INFRAROUGE PROCHE

  摘要：

  公开号：

  WO2012123916A3
• 作为产物：
  描述：

  2-羟基-5-氯甲基苯甲醛 在 乌洛托品 、 水 、 caesium carbonate 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 29.08h， 生成 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyloxy)isophthalaldehyde
  参考文献：
  名称：

  NIRF turn-on nanoparticles based on the tumor microenvironment for monitoring intracellular protein delivery

  摘要：

  一个双响应的近红外荧光开启蛋白传递系统已构建，将近红外荧光开启探针和蛋白合并到一个单一纳米颗粒中。

  DOI：

  10.1039/c9cc07768e

文献信息

• Simultaneous fluorescence imaging of selenol and hydrogen peroxide under normoxia and hypoxia in HepG2 cells and in vivo
  作者：Xiaojun Liu、Bo Hu、Ranran Cheng、Fanpeng Kong、Xiaohong Pan、Kehua Xu、Bo Tang

  DOI：10.1039/c6cc02111e

  日期：——

  Simultaneous fluorescence imaging of selenol and hydrogen peroxide with 5-FAM-peptide-AuNPs and QCy7-H₂O₂ was realized during tumor cell apoptosis induced by selenite.

  使用5-FAM-肽-AuNPs和QCy7-H₂O_{2>，在亚硒酸盐诱导的肿瘤细胞凋亡过程中，实现了硒醇和过氧化氢的同时荧光成像。}
• [EN] COMPOUNDS AS STIMULI-RESPONSIVE PROBES, METHODS AND APPLICATIONS THEREOF<br/>[FR] COMPOSÉS EN TANT QUE SONDES SENSIBLES À DES STIMULI, PROCÉDÉS ET APPLICATIONS ASSOCIÉS
  申请人：JAWAHARLAL NEHRU CENTRE FOR ADVANCED SCIENT RES

  公开号：WO2017033163A1

  公开（公告）日：2017-03-02

  The present disclosure relates to the field of synthetic pharmaceutical chemistry and biology. The disclosure provides a compound of Formula I and a process of preparation thereof. The disclosure further relates to methods and use of Formula I compounds as stimuli-responsive probes. Said Formula I compounds are employed for detecting and quantifying reactive oxygen species (ROS), and have related applications including but not limited fluorescence spectroscopy, diagnostics, treatment, imaging and biomedical applications.

  本公开涉及合成药物化学和生物学领域。本公开提供了一种I式化合物及其制备方法。此外，本公开还涉及将I式化合物作为刺激响应探针的方法和用途。所述的I式化合物用于检测和定量反应性氧化物种（ROS），并具有相关应用，包括但不限于荧光光谱学、诊断、治疗、成像和生物医学应用。
• H₂O₂-Activated NIR-II Fluorescent Probe with a Large Stokes Shift for High-Contrast Imaging in Drug-Induced Liver Injury Mice
  作者：Yang Tian、Senyao Liu、Wenwen Cao、Peng Wu、Zhaoming Chen、Hu Xiong

  DOI：10.1021/acs.analchem.2c02052

  日期：2022.8.16

  crucial role in the progression of DILI. However, there remains a challenge to develop H2O2-activatable second near-infrared (NIR-II, 1000–1700 nm) small molecular probes with both a large Stokes shift and a long emission wavelength beyond 950 nm. Herein, we developed an activatable NIR-II fluorescent probe (IR-990) with an acceptor-π-acceptor (A-π-A) skeleton for real-time detection of H2O2 in vivo.

  药物性肝损伤（DILI）是临床最常见的药物不良反应，与过量产生的活性氧引起的氧化应激密切相关。肝脏H 2 O 2作为DILI的重要生物标志物，在DILI的进展中起着至关重要的作用。然而，开发具有大斯托克斯位移和超过 950 nm 的长发射波长的H 2 O 2可激活的第二近红外（NIR-II，1000-1700 nm）小分子探针仍然存在挑战。在此，我们开发了一种具有受体-π-受体 (A-π-A) 骨架的可激活 NIR-II 荧光探针 ( IR-990 )，用于实时检测 H 2 O 2体内。在 H 2 O 2存在下，非荧光探针IR-990通过生成供体-π-受体 (D-π-A) 结构成功解锁并开启强烈的 NIR-II 荧光，在 990 nm 处表现出峰值发射波长和 200 nm 的大斯托克斯位移。此外，它还能够在体外以高灵敏度和选择性（LOD = 0.59 μM）检测H 2 O 2，​​并首次在
• Design, synthesis and application of a dual-functional fluorescent probe for reactive oxygen species and viscosity
  作者：Hongyu Li、Ya Liu、Xiaoyi Li、Xiaohua Li、Huimin Ma

  DOI：10.1016/j.saa.2020.119059

  日期：2021.2
• A Unique Paradigm for a Turn-ON Near-Infrared Cyanine-Based Probe: Noninvasive Intravital Optical Imaging of Hydrogen Peroxide
  作者：Naama Karton-Lifshin、Ehud Segal、Liora Omer、Moshe Portnoy、Ronit Satchi-Fainaro、Doron Shabat

  DOI：10.1021/ja203145v

  日期：2011.7.20

  The development of highly sensitive fluorescent probes in combination with innovative optical techniques is a promising strategy for intravital noninvasive quantitative imaging. Cyanine fluorochromes belong to a superfamily of dyes that have attracted substantial attention in probe design for molecular imaging. We have developed a novel paradigm to introduce a Turn-ON mechanism in cyanine molecules, based on a distinctive change in their pi-electrons system. Our new cyanine fluorochrome is synthesized through a simple two-step procedure and has an unprecedented high fluorescence quantum yield of 16% and large extinction coefficient of 52 000 M(-1) cm(-1). The synthetic strategy allows one to prepare probes for various analytes by introducing a specific triggering group on the probe molecule. The probe was equipped with a corresponding trigger and demonstrated efficient imaging of endogenous hydrogen peroxide, produced in an acute lipopolysaccharide-induced inflammation model in mice. This approach provides, for the first time, an available methodology to prepare modular molecular Turn-ON probes that can release an active cyanine fluorophore upon reaction with specific analyte.