Novel quinoline dye capable of being used as Golgi apparatus organelle probe

A phenyl and naphthyl technology, applied in the field of novel quinoline dyes, can solve the problems of inconvenience, numerous probe synthesis steps, etc., and achieve the effects of low cost, mild reaction conditions and high yield

Active Publication Date: 2015-04-22
UNIV OF SCI & TECH OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the synthesis steps of these functionalized probes are numerous and not simple enough.

Method used

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  • Novel quinoline dye capable of being used as Golgi apparatus organelle probe
  • Novel quinoline dye capable of being used as Golgi apparatus organelle probe
  • Novel quinoline dye capable of being used as Golgi apparatus organelle probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Synthesis of two quinoline dyes in chloroform:

[0045] Synthetic steps of Quinoline1:

[0046]

[0047] 1.00 g (4.63 mmol) of 4,4,4-trifluoro-1-phenyl-1,3-butanedione was dissolved in 50 ml of chloroform, and 0.50 g (4.63 mmol) of m-phenylenediamine was added thereto. The reaction system was immersed in an oil bath under N 2 Under protection, stir at reflux at 80°C for about 10 hours. Subsequently, the organic solvent was removed by rotary evaporation under reduced pressure, and the obtained crude product was recrystallized in chloroform, washed with n-hexane, and dried in vacuo to obtain Quinoline1 (1.17 g, 88%) as light grass green needle-like crystals. Structural characterization of Quinoline1: 1 H NMR (300MHz, CDCl 3 )δ8.14(m,2H,4-2'-ArH),7.93(m,1H,5-H),7.89(s,1H,3-H),7.52(m,3H,4-3', 4',5'-ArH),7.39(d,J=2.2Hz,1H,8-H),7.09(dd,J=9.0,2.4Hz,1H,6-H),4.22(broad s,7- NH 2 ,2H).MS(HRMS):m / z calcdforC 16 h 12 f 3 N 2 + 289.09526, found 289.09399.

[0048] Th...

Embodiment 2

[0055] Carry out Combs quinoline synthesis method in water:

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Abstract

The invention relates to a novel quinoline dye capable of being used as a Golgi apparatus organelle probe. In comparison of dye with a commercial Golgi apparatus organelle dye in term of imaging results in human osteosarcoma cells U2OS, the result proves that the dye disclosed by the invention can be used for targeted localization of the Golgi apparatus organelle. The dye has a great potential effect in the field of marking of the Golgi apparatus organelle.

Description

technical field [0001] The invention belongs to the field of materials, and in particular relates to a class of novel quinoline dyes that can be used as probes for Golgi apparatus organelles, a preparation method and application thereof. Background technique [0002] Quinoline compounds, as intermediates of many drug molecules in pharmaceutical engineering, are one of the most important fields in organic chemistry. Quinine, a natural quinoline derivative, is the first drug molecule to effectively treat malaria, and many quinoline derivatives (such as chloroquine, mefloquine) have antimalarial activity. In fact, quinine is also one of the fluorescent molecules recorded in history, with a very bright blue light emission, and is still used in the field of fluorescence quantum yield measurement today. In addition, 8-hydroxyquinoline aluminum is also the first compound used in organic light-emitting diodes (OLEDs) (C.W.Tang and S.A. VanSlyke, Appl. Phys. Lett., 1987, 51, 913). ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/38C09B57/00C12Q1/00
CPCC07D215/38C09B57/00C12Q1/00
Inventor 陈晓锋张国庆毕国强
Owner UNIV OF SCI & TECH OF CHINA
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