6-(1H-benzimidazol-2-yl)-N-methylnaphthalen-2-amine | 1489032-20-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-(1H-benzimidazol-2-yl)-N-methylnaphthalen-2-amine
• CAS: 1489032-20-3
• 化学式: C₁₈H₁₅N₃
• 分子量: 273.337
• InChiKey: NPRNBTWEVJAPAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  40.7
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  6-formyl-N-methyl-2-naphthylamine 、 邻苯二胺 在 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以31%的产率得到6-(1H-benzimidazol-2-yl)-N-methylnaphthalen-2-amine
  参考文献：
  名称：

  이광자 형광 프로브, 이의 제조방법 및 이를 이용한 pH 이미지화 방법

  摘要：

  This invention relates to a photon fluorescent probe that visualizes pH. The photon fluorescent probe of this invention is based on a benzimidazole derivative structure and detects the pH of acidic regions and its changes. The probe has inherent isotropic emission, low toxicity, and high photostability, and can indicate color changes in photon fluorescence between pH 4-7, allowing for pH measurement in increments of 0.001 units. The photon fluorescent probe according to this invention selectively stains living cells and biological tissues internally while reacting with acidic pH to show a strong fluorescence color change (blue-green). Additionally, due to high solubility in water and low molecular weight, it can be easily loaded into cells. Furthermore, it can selectively detect pH in living cells over a period of 60 minutes or more and in biological tissues at depths of 100-200 μm, enabling the investigation of the distribution and activity of pH in living cells or intact biological tissues through ratio imaging. Therefore, it enables quantitative analysis of pH, comparison analysis of different samples, and can significantly contribute to life science research related to pH, early diagnosis of diseases, and the development of diagnostic reagents and treatments.

  公开号：

  KR101584606B1

文献信息

• Benzimidazole-Based Ratiometric Two-Photon Fluorescent Probes for Acidic pH in Live Cells and Tissues
  作者：Hyung Joong Kim、Cheol Ho Heo、Hwan Myung Kim

  DOI：10.1021/ja409971k

  日期：2013.11.27

  Many aspects of cell metabolism are controlled by acidic pH. We report a new family of small molecule and ratiometric two photon (TP) probes derived from benzimidazole (BH1-3 and BH1L) for monitoring acidic pH values. These probes are characterized by a strong two-photon excited fluorescence, a marked blue-to-green emission color change in response to pH, pK(a) values ranging from 4.9 to 6.1, a distinctive isoemissive point, negligible cytotoxicity, and high photostability, thereby allowing quantitative analysis of acidic pH. Moreover, we show that BH1L optimized as a lysosomal-targeted probe allows for direct, real-time estimation of the pH values inside lysosomal compartments in live cells as well as in living mouse brain tissues through the use of two-photon microscopy. These findings demonstrate that these probes will find useful applications in biomedical research.