O6-[4-(三氟乙酰氨基甲基)苄基]鸟嘌呤 | 680622-70-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: O6-[4-(三氟乙酰氨基甲基)苄基]鸟嘌呤
• 中文别名: O6-[4-（三氟乙酰氨基甲基）苄基]鸟嘌呤
• 英文名称: N-[4-(2-amino-9H-purin-6-yloxymethyl)benzyl]-2,2,2-trifluoroacetamide
• 英文别名: O-6-[4-trifluoroacetamidomethylbenzyl]guanine；O6-[4-(Trifluoroacetamidomethyl)benzyl]guanine；N-[[4-[(2-amino-7H-purin-6-yl)oxymethyl]phenyl]methyl]-2,2,2-trifluoroacetamide
• CAS: 680622-70-2
• 化学式: C₁₅H₁₃F₃N₆O₂
• 分子量: 366.302
• InChiKey: AQFWAWXGBQPBIA-UHFFFAOYSA-N

物化性质

• 熔点：
  211-213?C
• 密度：
  1.525±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  119
• 氢给体数：
  3
• 氢受体数：
  9

安全信息

• 储存条件：
  -20°C，密封保存，并保持干燥。

制备方法与用途

生物活性

PIN1抑制剂API-1是一种特异性的Pin1（肽基-脯氨酰顺反异构酶NIMA相互作用蛋白1）抑制剂，其IC50值为72.3 nM。该抑制剂靶向Pin1的肽基-脯氨酰异构酶域，并抑制其顺反异构活性。通过保留活性XPO5构象，PIN1抑制剂API-1上调miRNA生物发生并抑制肝细胞癌的发展。

靶点

Target	Value
Pin1 (Cell-free assay)	72.3 nM

反应信息

• 作为反应物：
  描述：

  O6-[4-(三氟乙酰氨基甲基)苄基]鸟嘌呤 在 potassium carbonate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 6-[8-(4-dimethylamino-phenyl)-1,2-dimethyl-7-oxo-7H-pyrano[3,2-e]indol-3-yl]-hexanoic acid 4-(2-amino-9H-purin-6-yloxymethyl)-benzylamide
  参考文献：
  名称：

  Syntheses and characterizations of novel pyrrolocoumarin probes for SNAP-tag labeling technology

  摘要：

  SNAP-tag technology is a revolutionary protein labeling technology employing in various biological studies. Since low signal/noise ratio and severe overlap between the FRET donors/acceptors often occurred in applying present fluorescent probes and thus limited the further applications, development of new fluorescent probes with excellent fluorescent properties is still of request by today's SNAP-tag technology. In this paper, a number of SNAP-tag protein probes have been developed by incorporating a novel pyrrolocoumarin fluorophore recently developed by our group. Examination of these novel synthetic compounds shows all these materials possess satisfactory fluorescent properties. Among these, probe 7 exhibits the most excellent characters, and its quantum yield, maximum emission wavelength and Stocks shift reach to 0.44, 534 nm and 112 nm, respectively. Further analysis of structure-property relationship indicates that the probes with a longer C3-substituted alkyl (such as pentyl) give stronger fluorescence. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.075
• 作为产物：
  描述：

  对氰基苯甲酸甲酯 在 吡啶 、 lithium aluminium tetrahydride 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 生成 O6-[4-(三氟乙酰氨基甲基)苄基]鸟嘌呤
  参考文献：
  名称：

  Syntheses and characterizations of novel pyrrolocoumarin probes for SNAP-tag labeling technology

  摘要：

  SNAP-tag technology is a revolutionary protein labeling technology employing in various biological studies. Since low signal/noise ratio and severe overlap between the FRET donors/acceptors often occurred in applying present fluorescent probes and thus limited the further applications, development of new fluorescent probes with excellent fluorescent properties is still of request by today's SNAP-tag technology. In this paper, a number of SNAP-tag protein probes have been developed by incorporating a novel pyrrolocoumarin fluorophore recently developed by our group. Examination of these novel synthetic compounds shows all these materials possess satisfactory fluorescent properties. Among these, probe 7 exhibits the most excellent characters, and its quantum yield, maximum emission wavelength and Stocks shift reach to 0.44, 534 nm and 112 nm, respectively. Further analysis of structure-property relationship indicates that the probes with a longer C3-substituted alkyl (such as pentyl) give stronger fluorescence. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.075

文献信息

• Highly Activatable and Environment-Insensitive Optical Highlighters for Selective Spatiotemporal Imaging of Target Proteins
  作者：Tomonori Kobayashi、Toru Komatsu、Mako Kamiya、Cláudia Campos、Marcos González-Gaitán、Takuya Terai、Kenjiro Hanaoka、Tetsuo Nagano、Yasuteru Urano

  DOI：10.1021/ja212125w

  日期：2012.7.11

  Optical highlighters are photoactivatable fluorescent molecules that exhibit pronounced changes in their spectral properties in response to irradiation with light of a specific wavelength and intensity. Here, we present a novel design strategy for a new class of caged BODIPY (4,4-difluoro-4-bora-3a,4a-diaza-s-indacene) fluorophores, based on the use of photoremovable protecting groups (PRPGs) with

  光学荧光笔是可光活化的荧光分子，在特定波长和强度的光照射下，其光谱特性会发生显着变化。在这里，我们提出了一种新型笼状 BODIPY（4,4-difluoro-4-bora-3a,4a-diaza-s-indacene）荧光团的新设计策略，基于使用光可去除保护基（PRPGs）与高还原电位，通过光诱导电子转移 (PeT) 作为光敏单元和荧光猝灭剂。2,6-二硝基苄基 (DNB) 笼式 BODIPY 被有效地光活化，在水溶液中的活化率超过 600 倍。然后，我们使用成熟的 SNAP 标签技术将此光活化荧光团与 SNAP（O(6)-烷基鸟嘌呤 DNA 烷基转移酶的突变体）配体相结合，以获得用于蛋白质动力学可视化的基于小分子的光学荧光笔。作为概念证明，我们展示了活细胞中具有 SNAP 标签的表皮生长因子受体 (EGFR) 融合蛋白的时空成像。我们还展示了使用组蛋白 2A 的融合蛋白与 SNAP 标签突出显示活斑马鱼胚胎中感兴趣的细胞。
• [EN] DYE COMPOSITIONS, METHODS OF PREPARATION, CONJUGATES THEREOF, AND METHODS OF USE<br/>[FR] COMPOSITIONS DE COLORANT, PROCÉDÉS DE PRÉPARATION, CONJUGUÉS ASSOCIÉS, ET PROCÉDÉS D'UTILISATION
  申请人：UNIV CORNELL

  公开号：WO2013109859A1

  公开（公告）日：2013-07-25

  Dye compounds of the formula (1) wherein A is a protective agent group that has a characteristic of modifying the singlet-triplet occupancy of the shown cyanine moiety, and M is a reactive crosslinking group or a group that can be converted to a reactive crosslinking group. Methods for synthesizing the dye compounds and applications for their use are also described.

  化合物的染料的公式（1），其中A是一种保护剂基团，具有修改所示青菁基团的单三态占据特性，而M是一种反应性交联基团或可转化为反应性交联基团的基团。还描述了合成染料化合物的方法以及它们的用途。
• Photoproximity Profiling of Protein–Protein Interactions in Cells
  作者：David C. McCutcheon、Gihoon Lee、Anthony Carlos、Jeffrey E. Montgomery、Raymond E. Moellering

  DOI：10.1021/jacs.9b06528

  日期：2020.1.8

  We report a novel photoproximity protein interaction (PhotoPPI) profiling method to map protein-protein interactions in vitro and in live cells. This approach utilizes a bioorthogonal, multifunctional chemical probe that can be targeted to a genetically encoded protein of interest (POI) through a modular SNAP-Tag/benzylguanine covalent interaction. A first generation photoproximity probe, PP1, responds

  我们报告了一种新的光邻近蛋白质相互作用（PhotoPPI）分析方法，用于绘制体外和活细胞中蛋白质-蛋白质相互作用的图谱。该方法利用生物正交多功能化学探针，可通过模块化 SNAP-Tag/苄基鸟嘌呤共价相互作用靶向基因编码的目标蛋白 (POI)。第一代光邻近探针 PP1 响应 365 nm 光，同时裂解中心硝基藜芦基连接体和外围二氮丙啶基团，导致高反应性卡宾亲核试剂从 POI 扩散开。我们在体外演示了简单的探针加载，以及随后的模型蛋白质-蛋白质相互作用（PPI）的相互作用和光依赖性近端标记。PhotoPPI 工作流程与定量 LC-MS/MS 的集成首次在活细胞中实现了氧化还原调节传感器蛋白 KEAP1 的无偏相互作用图谱。我们在基础细胞条件下验证了 KEAP1 与蛋白质 PGAM5 和 HK2 等之间已知和新颖的相互作用。相比之下，对经历代谢或氧化还原应激的细胞中的 PhotoPPI 谱进行比较证实，KEAP1
• [EN] PHOTOPROXIMITY PROFILING OF PROTEIN-PROTEIN INTERACTIONS IN CELLS<br/>[FR] PROFILAGE DE PHOTOPROXIMITÉ D'INTERACTIONS PROTÉINE-PROTÉINE DANS DES CELLULES
  申请人：UNIV CHICAGO

  公开号：WO2021055960A1

  公开（公告）日：2021-03-25

  Photoactive probes and probe systems for detecting biological interactions are described. The photoactive probes include probes that combine both photocleavable and photoreactive moieties. The photoactive probe systems can include a first probe comprising a photocatalytic group and a second probe comprising a group that can act as a substrate for the reaction catalyzed by the photocatalytic group. The probes and probe systems can also include groups that can specifically bind to a binding partner on a biological entity of interest and a detectable group or a precursor thereof. The probes and probe systems can detect spatiotemporal interactions of proteins or cells. In some embodiments, the interactions can be detected in live cells. Also described are methods of detecting the biological interactions.

  描述了用于检测生物相互作用的光活性探针和探针系统。光活性探针包括同时结合光解和光反应基团的探针。光活性探针系统可以包括第一探针，其中包括光催化基团，以及第二探针，其中包括可作为光催化基团催化反应底物的基团。探针和探针系统还可以包括能够特异性结合到感兴趣生物实体上的结合伙伴的基团，以及可检测的基团或其前体。这些探针和探针系统可以检测蛋白质或细胞的时空相互作用。在某些实施方式中，这些相互作用可以在活细胞中检测到。还描述了检测生物相互作用的方法。
• 一种β-氯乙基亚硝基脲类化合物及其合成方法 和用途
  申请人：北京工业大学

  公开号：CN104031048B

  公开（公告）日：2016-03-09

  本发明涉及一种新型的β-氯乙基亚硝基脲类化合物及其合成方法和用途，所述β-氯乙基亚硝基脲类化合物的结构如通式(Ⅱ)所示。本发明对通式Ⅱ中的化合物进行了体外抗肿瘤筛选试验。结果表明，通式Ι中的化合物对人脑神经胶质瘤细胞SF763、SF767、SF126、SF188，人结肠癌细胞HT29和小鼠白血病细胞L1210等多种肿瘤细胞系均有明显的抑制作用，且比现有的CENU及其与O6-苄基鸟嘌呤的联合用药具有更高的肿瘤抑制活性。