黑暗猝灭剂BHQ-3,BHQ-3NHS | 871240-94-7

• 物质功能分类: 生物 - 染料/染色剂
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 黑暗猝灭剂BHQ-3,BHQ-3NHS
• 英文名称: BHQ-3-OSu
• 英文别名: (2,5-dioxopyrrolidin-1-yl) 4-[4-[[8-(diethylamino)-10-phenylphenazin-10-ium-2-yl]diazenyl]-N-methylanilino]butanoate
• CAS: 871240-94-7
• 化学式: C₃₇H₃₈N₇O₄
• 分子量: 644.753
• InChiKey: QGXKSFXRZRDECO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  48
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3-氨基丙基三乙氧基硅烷 、 黑暗猝灭剂BHQ-3,BHQ-3NHS 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  使用广谱纳米淬灭剂对细胞内蛋白水解级联进行多重成像

  摘要：

  把灯关掉！已经开发出一种通用纳米淬灭剂，通过将一系列暗淬灭剂掺入可渗透细胞的介孔二氧化硅纳米颗粒中，可以淬灭范围广泛的可见光至近红外染料。与染料标记的底物相结合，这种纳米淬灭剂在特定的蛋白水解作用下增强了多个荧光信号，从而可以对蛋白水解级联进行实时成像（参见方案）。

  DOI：

  10.1002/anie.201107795

文献信息

• IMAGING AGENTS FOR IMAGING PROTEASE ACTIVITY AND USES THEREOF
  申请人：The United States of America, as represented by the Secretary, Department of Health and Human Ser.

  公开号：US20170143851A1

  公开（公告）日：2017-05-25

  Disclosed are imaging agents having the following Formula I: wherein F is a near infrared fluorophore, S is an enzymatically cleavable oligopeptide, Q is a fluorescence quencher molecule, and M is a moiety selected from the group consisting of PEG or derivative thereof and a targeting ligand, and wherein F, Q and M are linked to separate amino acids of the enzymatically cleavable oligopeptide. Compositions comprising such compounds, as well as methods of use, methods of identifying a cell or a population of cells in vivo expressing a protease of interest, and methods of treating a disease through imaging are also disclosed.

  揭示了具有以下公式I的成像剂：其中F是近红外荧光色素，S是酶可切割寡肽，Q是荧光猝灭剂分子，M是选择自PEG或其衍生物和靶向配体组成的一组中的一种的基团，其中F、Q和M与酶可切割寡肽的不同氨基酸连接。还揭示了包含这种化合物的组合物，以及使用方法，用于识别体内表达感兴趣蛋白酶的细胞或细胞群的方法，以及通过成像治疗疾病的方法。
• Design and Synthesis of Cathepsin-K-Activated Osteoadsorptive Fluorogenic Sentinel (OFS) Probes for Detecting Early Osteoclastic Bone Resorption in a Multiple Myeloma Mouse Model
  作者：Eric T. Richard、Kenzo Morinaga、Yiying Zheng、Oskar Sundberg、Akishige Hokugo、Kimberly Hui、Yipin Zhou、Hodaka Sasaki、Boris A. Kashemirov、Ichiro Nishimura、Charles E. McKenna

  DOI：10.1021/acs.bioconjchem.1c00036

  日期：2021.5.19

  We describe the design and synthesis of OFS-1, an Osteoadsorptive Fluorogenic Sentinel imaging probe that is adsorbed by hydroxyapatite (HAp) and bone mineral surfaces, where it generates an external fluorescent signal in response to osteoclast-secreted cathepsin K (Ctsk). The probe consists of a bone-anchoring bisphosphonate moiety connected to a Förster resonance energy transfer (FRET) internally quenched fluorescent (IQF) dye pair, linked by a Ctsk peptide substrate, GHPGGPQG. Key structural features contributing to the effectiveness of OFS-1 were defined by structure–activity relationship (SAR) and modeling studies comparing OFS-1 with two cognates, OFS-2 and OFS-3. In solution or when preadsorbed on HAp, OFS-1 exhibited strong fluorescence when exposed to Ctsk (2.5–20 nM). Time-lapse photomicrographs obtained after seeding human osteoclasts onto HAp-coated well plates containing preadsorbed OFS-1 revealed bright fluorescence at the periphery of resorbing cells. OFS-1 administered systemically detected early osteolysis colocalized with orthotopic engraftment of RPMI-8226-Luc human multiple myeloma cells at a metastatic skeletal site in a humanized mouse model. OFS-1 is thus a promising new imaging tool for detecting abnormal bone resorption.

  我们描述了 OFS-1 的设计和合成，OFS-1 是一种骨吸附荧光前哨成像探针，被羟基磷灰石 (HAp) 和骨矿物质表面吸附，产生外部荧光信号以响应破骨细胞分泌的组织蛋白酶 K (Ctsk)。该探针由骨锚定双膦酸盐部分组成，该部分连接到福斯特共振能量转移 (FRET) 内部猝灭荧光 (IQF) 染料对，并通过 Ctsk 肽底物 GHPGGPQG 连接。通过结构-活性关系 (SAR) 和比较 OFS-1 与两个同源物 OFS-2 和 OFS-3 的模型研究，定义了有助于 OFS-1 有效性的关键结构特征。在溶液中或预吸附在 HAp 上时，OFS-1 在暴露于 Ctsk (2.5–20 nM) 时表现出强烈的荧光。将人破骨细胞接种到含有预吸附 OFS-1 的 HAp 包被孔板上后获得的延时显微照片显示，再吸收细胞周围有明亮的荧光。在人源化小鼠模型中，施用 OFS-1 系统地检测到与 RPMI-8226-Luc 人类多发性骨髓瘤细胞原位移植在骨转移部位共定位的早期骨质溶解。因此，OFS-1 是一种有前途的新型成像工具，用于检测骨吸收异常。
• Functional in vivo imaging of cysteine cathepsin activity in murine model of inflammation
  作者：Dejan Caglič、Anja Globisch、Maik Kindermann、Ngee-Han Lim、Volker Jeske、Hans-Paul Juretschke、Eckart Bartnik、K. Ulrich Weithmann、Hideaki Nagase、Boris Turk、K. Ulrich Wendt

  DOI：10.1016/j.bmc.2010.10.028

  日期：2011.2

  protease inhibitors for investigations in proteomic lysates as well as for in vivo molecular imaging studies. The newly developed activity-based probe AW-091 was demonstrated to be highly selective for cathepsin S in vitro and proved useful in monitoring cysteine cathepsin activity in vivo, that is, in zymosan-induced mouse model of inflammation. AW-091 showed higher signal-to-background ratios at earlier

  在生物分子成像应用中，即在用于肿瘤成像或炎症研究的动物模型中，近红外荧光团（NIRF）标记的成像探针变得越来越重要。在这项研究中，我们证明了先前引入的“逆向设计”化学概念代表了一种有效策略，用于从经过化学优化的蛋白酶抑制剂生成半胱氨酸蛋白酶的选择性探针，以用于蛋白质组裂解物的研究以及体内分子成像研究。新开发的基于活性的探针AW-091在体外对组织蛋白酶S具有高度选择性，并被证明可用于体内监测半胱氨酸组织蛋白酶的活性，即在酵母聚糖诱导的小鼠炎症模型中。与商用聚合物ProSense680（VisEn Medical）相比，AW-091在较早的时间点处显示出更高的信噪比，因此是研究导致早期多种蛋白水解过程（包括炎症，癌症和类风湿关节炎。此外，已显示，通过给予抗炎药地塞米松和组织蛋白酶抑制剂E-64，可减少源自裂解的AW-091的荧光信号，从而为评估小分子抑制剂提供了有价值的系统蛋白酶。
• A Highly Bright Near‐Infrared Afterglow Luminophore for Activatable Ultrasensitive In Vivo Imaging
  作者：Li Yang、Min Zhao、Wan Chen、Jieli Zhu、Weina Xu、Qing Li、Kanyi Pu、Qingqing Miao

  DOI：10.1002/anie.202313117

  日期：2024.1.22

  An “all-in-one” afterglow probe was designed, exhibiting high 1O2 generation and capture ability with a single molecule. Through intramolecular energy transfer strategy, the afterglow probe showed an extremely bright afterglow luminescence with an emission wavelength located in NIR-I region (>650 nm), which allowed deeper tissue penetration, higher signal-to-background ratio, and imaging sensitivity

  设计了一种“一体式”余辉探针，具有单分子高1 O 2生成和捕获能力。通过分子内能量转移策略，余辉探针表现出极其明亮的余辉发光，发射波长位于NIR-I区域（>650 nm），这使得余辉探针能够更深的组织穿透、更高的信号背景比和成像灵敏度。体外和体内。
• IONIC COMPLEX NANOPARTICLES FOR DETECTING HEPARANASE ACTIVITIES AND METHOD FOR PREPARING THE SAME
  申请人：KWON Ick-Chan

  公开号：US20100233085A1

  公开（公告）日：2010-09-16

  Disclosed are Ionic complex nanoparticles for detecting heparanase activities and a method for preparing the same. More specifically, disclosed are Ionic complex nanoparticles for detecting heparanase activities, wherein negative-ion substrate polymers specifically degraded by heparanase and positive-ion biocompatible polymers ionically bind to each other, and fluorophores or quenchers bind to each of the polymers. The ionic complex nanoparticles for detecting heparanase activities may be applied to a method for screening novel drugs such as inhibitors that prevent over-expression of heparanase. Various cells and tissues where over-expression of heparanase occurs may be non-invasively imaged in cancer cells, cancer tissues, and tissues of various inflammatory diseases. Accordingly, the ionic complex nanoparticles for detecting heparanase activities may be effectively used to early diagnose various diseases and incurable diseases including autoimmune diseases such as cancers, osteoarthritis, rheumatoid arthritis, and dementia.