N-[6-(acenaphthyleno[1,2-b]quinoxalin-3-ylamino)hexyl]-2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetamide | 1392279-99-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: N-[6-(acenaphthyleno[1,2-b]quinoxalin-3-ylamino)hexyl]-2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetamide
• CAS: 1392279-99-0
• 化学式: C₄₃H₃₈ClN₅O₃
• 分子量: 708.259
• InChiKey: BSVAHPRQNWRQKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.38
• 重原子数：
  52.0
• 可旋转键数：
  12.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  98.14
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  3-bromoacenaphtho[1,2-b]quinoxaline 在 4-甲基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 乙二醇甲醚 为溶剂， 反应 31.0h， 生成 N-[6-(acenaphthyleno[1,2-b]quinoxalin-3-ylamino)hexyl]-2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetamide
  参考文献：
  名称：

  TWO-PHOTON FLUORESCENT PROBE USING NAPHTHALENE AS MATRIX AND PREPARATION METHOD AND USE THEREOF

  摘要：

  公开号：

  EP2778161B1

文献信息

• An Off–On COX-2-Specific Fluorescent Probe: Targeting the Golgi Apparatus of Cancer Cells
  作者：Hua Zhang、Jiangli Fan、Jingyun Wang、Shuangzhe Zhang、Bairui Dou、Xiaojun Peng

  DOI：10.1021/ja4056905

  日期：2013.8.7

  Identifying cancer cells and quantifying cancer-related events in particular organelles in a rapid and sensitive fashion are important for early diagnosis and for studies on pathology and therapeutics of cancers. Herein a smart "off-on" cyclooxygenase-2-specific fluorescence probe (ANQ-IMC-6), able to report the presence of cancer cells and to image Golgi-related events, has been designed and evaluated. Cyclooxygenase-2 (COX-2) has been used as imaging target in the probe design, since this enzyme is a biomarker of virtually all cancer cell lines. In the free state in aqueous solution, ANQ-IMC-6 mainly exists in a folded conformation where probe fluorescence is quenched through photoinduced electron transfer between the fluorophore acenaphtho[1,2-b]quinoxaline (ANQ) and the recognition group, indomethacin (IMC). Fluorescence is turned on, by restraining the photoinduced electron transfer, when ANQ-IMC-6 is forced to adopt the unfolded state following binding to COX-2 in the Golgi apparatus of cancer cells. ANQ-IMC-6 provides high signal-to-background staining and has been successfully used to rapidly differentiate cancer cells from normal cells when using flow cytometry and one- and two-photon fluorescence microscopic imaging. Furthermore, ANQ-IMC-6 may be able to visualize dynamic changes of the Golgi apparatus during cancer cell apoptosis, with possible application to early diagnosis.
• NAPHTHALENE-BASED TWO-PHOTON FLUORESCENT PROBES, PREPARATION METHOD AND USE THEREOF
  申请人：Peng Xiaojun

  公开号：US20150079625A1

  公开（公告）日：2015-03-19

  The present invention provides a novel category of naphthalene-based two-photon fluorescent probes having a general formula I, wherein: X is selected from the X 1 , X 2 , X 3 and X 4 ; The mentioned two-photon fluorescent probes have a low fluorescence background in the non-tumor cells and tissues, and have a strong and specific fluorescent signal in the tumor cells and tissues. These probes have a certain level of water-solubility, while having good membrane permeability. In addition, they have a bigger effective two-photon absorption cross section. The compounds of the present invention also have a lower biotoxicity, phototoxicity and photobleaching. There is sufficient difference between the spectral range thereof and that of a biological sample.
• US9182350B2
  申请人：——

  公开号：US9182350B2

  公开（公告）日：2015-11-10
• TWO-PHOTON FLUORESCENT PROBE USING NAPHTHALENE AS MATRIX AND PREPARATION METHOD AND USE THEREOF
  申请人：Dalian University Of Technology

  公开号：EP2778161B1

  公开（公告）日：2015-05-06