8-(bis(2-hydroxyethyl)amino)-10-phenylfluoranthene-7-carbonitrile

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 8-(bis(2-hydroxyethyl)amino)-10-phenylfluoranthene-7-carbonitrile
• 英文别名: 8-[Bis(2-hydroxyethyl)amino]-10-phenylfluoranthene-7-carbonitrile；8-[bis(2-hydroxyethyl)amino]-10-phenylfluoranthene-7-carbonitrile
• 化学式: C₂₇H₂₂N₂O₂
• 分子量: 406.484
• InChiKey: FQSXSJSVKUBZDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  67.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-(bis(2-hydroxyethyl)amino)-2-oxo-6-phenyl-2H-pyran-3-carbonitrile 、 1-苊酮 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 生成 8-(bis(2-hydroxyethyl)amino)-10-phenylfluoranthene-7-carbonitrile
  参考文献：
  名称：

  Imaging and Quantitative Detection of Lipid Droplets by Yellow Fluorescent Probes in Liver Sections of Plasmodium Infected Mice and Third Stage Human Cervical Cancer Tissues

  摘要：

  与脂质异常相关的疾病的诊断和预后是极其重要的领域。在此方向上，通过结合存在于生物膜中的磷脂磷脂酰乙醇胺的乙醇胺头部基团，设计并合成了基于荧蒽的黄色荧光探针（FLUN-550、FLUN-552、FLUN-547）。由于其独特光物理特性和水溶性，这些探针成功用于前脂肪细胞和利什曼原虫前鞭毛体中脂滴的染色。此外，利用荧光探针FLUN-550和FLUN-552，我们成功成像并定量检测了恶性疟原虫耐多药小鼠肝切片中脂质过量积累（3至4倍）以及第三阶段人宫颈癌组织切片中的脂质积累（1.5至2倍），相较于正常组织。据我们所知，这是首次报道用于成像和定量检测人宫颈癌组织中脂滴的黄色荧光探针。这些新型黄色荧光脂质探针（FLUN-550和FLUN-552）在宫颈癌患者的诊断中展现出巨大潜力。

  DOI：

  10.1021/acs.bioconjchem.8b00552

文献信息

• [EN] SUBSTITUTED FLUORANTHENE-7-CARBONITRILES AS FLUORESCENT DYES FOR CELL IMAGING APPLICATIONS<br/>[FR] FLUORANTHÈNE-7-CARBONITRILES SUBSTITUÉS UTILISÉS EN TANT QUE COLORANTS FLUORESCENTS POUR DES APPLICATIONS D'IMAGERIE CELLULAIRE
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2014147642A1

  公开（公告）日：2014-09-25

  The present invention relates to novel donor-acceptor fluoranthenes of the general formula I which can be used potentially in developing fluorescent probes, and a process of preparing said novel compounds. More particularly, the present invention relates to amine or alkoxy group as donor and nitrile group as an acceptor attached to the fluoranthene skeleton, processes for preparing the said compounds and their uses as fluorescent probes in chemical and biological sciences such as cell imaging applications, diagnostics, fluorescent tags and other useful applications. The compounds are prepared by reacting 2H-pyran-2-ones in isolated or rigid conformations with cyclic ketones containing methylene carbonyl moiety in the presence of a base in an organic solvent.

  本发明涉及一种新型供体-受体氟蒽化合物，其通式为I，可能用于开发荧光探针，并提供了制备这些新型化合物的方法。更具体地说，本发明涉及将胺或烷氧基作为供体，将腈基作为受体连接到氟蒽骨架上，制备这些化合物的方法，以及它们在化学和生物科学中作为荧光探针的用途，如细胞成像应用、诊断、荧光标记和其他有用的应用。这些化合物是通过在有机溶剂中在孤立或刚性构象下，将2H-吡喃-2-酮与含有亚甲基羰基团的环状酮在碱存在下反应而制备的。
• Imaging and Quantitative Detection of Lipid Droplets by Yellow Fluorescent Probes in Liver Sections of <i>Plasmodium</i> Infected Mice and Third Stage Human Cervical Cancer Tissues
  作者：Ashutosh Sharma、Ajay K. Jha、Shachi Mishra、Ankita Jain、Bhavana S. Chauhan、Manoj Kathuria、Kundan S. Rawat、Neeraj M. Gupta、Renu Tripathi、Kalyan Mitra、Monika Sachdev、Madan L. B. Bhatt、Atul Goel

  DOI：10.1021/acs.bioconjchem.8b00552

  日期：2018.11.21

  The diagnosis and prognosis of the disease associated with lipid irregularity are areas of extreme significance. In this direction, fluoranthene based yellow fluorescent probes (FLUN-550, FLUN-552, FLUN-547) were designed and synthesized by conjugating the ethanolamine headgroup of the phospholipid phosphatidyl-ethanolamine present in biological membranes. Owing to unique photophysical properties and aqueous compatibility, these probes were successfully employed for staining lipid droplets (LDs) in preadipocytes and Leishmania donovani promastigotes. Furthermore, using the fluorescent probes FLUN-550 and FLUN-552 we successfully imaged and quantitatively detected the excess accumulation of lipids in a liver section of Plasmodium yoelii MDR infected mice (3- to 4-fold) and the tissue sections of third stage human cervical cancer patients (1.5- to 2-fold) compared to normal tissues. To the best of our knowledge, this is the first report of yellow fluorescent probes for imaging and quantitative detection of LDs in human cervical cancer tissues. These new yellow fluorescent lipid probes (FLUN-550 and FLUN-552) showed great potential for diagnosis of cervical cancer patients.

  与脂质异常相关的疾病的诊断和预后是极其重要的领域。在此方向上，通过结合存在于生物膜中的磷脂磷脂酰乙醇胺的乙醇胺头部基团，设计并合成了基于荧蒽的黄色荧光探针（FLUN-550、FLUN-552、FLUN-547）。由于其独特光物理特性和水溶性，这些探针成功用于前脂肪细胞和利什曼原虫前鞭毛体中脂滴的染色。此外，利用荧光探针FLUN-550和FLUN-552，我们成功成像并定量检测了恶性疟原虫耐多药小鼠肝切片中脂质过量积累（3至4倍）以及第三阶段人宫颈癌组织切片中的脂质积累（1.5至2倍），相较于正常组织。据我们所知，这是首次报道用于成像和定量检测人宫颈癌组织中脂滴的黄色荧光探针。这些新型黄色荧光脂质探针（FLUN-550和FLUN-552）在宫颈癌患者的诊断中展现出巨大潜力。