Naphthalimide fluorochrome and its preparation and application

A technology of fluorescent dyes and naphthalimide, applied in the directions of naphthalene dicarboxamide dyes/phthalimide dyes, luminescent materials, fluorescence/phosphorescence, etc., to achieve the effects of mild reaction conditions, strong practical application value, and easy synthesis

Active Publication Date: 2013-11-06
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, there is no literature report that the naphthalimide probe designed by using the PET mechanism is applied to the detection of environmental viscosity and its application to cell environment imaging

Method used

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  • Naphthalimide fluorochrome and its preparation and application
  • Naphthalimide fluorochrome and its preparation and application
  • Naphthalimide fluorochrome and its preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Embodiment 1: the preparation method of compound I

[0041] Heat 5g (0.018mol) of 4-bromo-1,8-naphthalene anhydride and 300ml ethanol to 78°C, dissolve and cool to 50°C, add 2.63mL (0.018mol) of n-butylamine dropwise, reflux for 8 hours, and cool to precipitate The solid was filtered to obtain compound I, 5 g (yield 83.3%).

Embodiment 2

[0042] Embodiment 2: the preparation method of compound II

[0043]

[0044] Mix 3.31g (0.01mol) of compound I and 1.61g (0.02mol) of N-methylethanolamine in 20ml of ethylene glycol methyl ether, add 2.78ml (0.02mol) of triethylamine under magnetic stirring, and react at 124°C for 12 hours. After cooling to room temperature, the reaction solution was added to ice water, a large amount of product was precipitated, and 2.45 g of pure product was obtained by passing through the column, with a yield of 75.15%. NMR and mass spectrometry data for product structure identification: 1 H NMR (400 MHz, CDCl3) δ 8.60 (d, J = 7.3 Hz, 1H), 8.51 (d, J = 8.2 Hz, 2H), 7.71 (d, J = 8.5 Hz, 1H), 7.32 – 7.18 (m , 4H), 4.21 – 4.11 (m, 2H), 3.74 (t, J = 6.9 Hz, 2H), 3.59 (t, J = 7.0 Hz, 2H), 3.10 (s, 3H), 1.77 – 1.65 (m, 2H), 1.45 (m, J = 7.5 Hz, 2H), 0.97 (t, J = 7.4 Hz, 3H).

[0045] HRMS-ESI: m / z calcd for [M + H] + C 19 h 21 N 2 o 2 Br ,389.0786; found,389.085.

Embodiment 3

[0046] Embodiment 3: the preparation method of compound III

[0047]

[0048] 1.63g (0.005mol) of compound II was dissolved in 20ml of dichloromethane, and 0.57ml (0.006mol) of phosphorus tribromide was added dropwise under ice cooling, and reacted at 0°C for 8 hours. The reaction solution was poured into ice water and continued to stir for 0.5 hours, washed with water three times to collect the organic phase, dried over anhydrous magnesium sulfate, filtered and spin-dried to obtain a crude product. After passing through the column (petroleum ether: ethyl acetate = 4:1 as the eluent), 1.38 g of pure product was obtained (71.1% yield). NMR and mass spectrometry data for product structure identification: 1 H NMR (400 MHz, CDCl3) δ 8.60 (d, J = 7.3Hz, 1H), 8.51 (d, J = 8.2 Hz, 2H), 7.71 (d, J = 8.5 Hz, 1H), 7.32 – 7.18 (m , 4H), 4.21 – 4.11 (m, 2H), 3.74 (t, J = 6.9 Hz, 2H), 3.59 (t, J = 7.0 Hz, 2H), 3.10 (s, 3H), 1.77 – 1.65 (m, 2H), 1.45 (m, J = 7.5 Hz, 2H), 0.97 (t, J = ...

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Abstract

The invention belongs to the technical field of fine chemicals and relates to a naphthalimide fluorochrome and its preparation and application. According to the invention, the naphthalimide fluorochrome is a fluorescence molecular probe which is designed and synthesized by PET mechanism and used in detecting environmental viscosity changes and can be used to carrying out two-photon ratio imaging and lifetime imaging on viscosity changes in cells. The naphthalimide fluorochrome provided by the invention has advantages of simple synthesis, mild synthesis condition, good photostability and the like, and is not sensitive to pH, polarity and biomacromolecules. Thus, the naphthalimide fluorochrome can be used to detect viscosity distribution in cells. In addition, it is reflected through two-photon ratio imaging that viscosity in a lysosome is the largest in a cell. Fluorescence ratio detection can overcome errors caused by only being dependent on fluorescence intensity changes. On the other hand, through medical stimulation on cells, viscosity changes in cells can be detected. Through fluorescence lifetime, values of viscosity changes can be reflected more visually. The naphthalimide fluorochrome has wide application value in the field of biology and environment.

Description

technical field [0001] The invention relates to a naphthalimide fluorescent dye and its preparation and application, belonging to the technical field of fine chemicals. Background technique [0002] Viscosity is a measure of the viscosity of a fluid, which is an expression of the fluid's flow force and its internal friction phenomenon. In living organisms, viscosity also plays an important role in the transmission of substances and signals in cells, etc. Because cell membrane and cytoplasm have viscoelasticity in cell biology, changes in viscosity will lead to changes in a series of physiological processes, especially some diseases. However, traditional viscosity instruments are difficult to measure micro-viscosity changes in biological tissues and cells in microbial systems. Fluorescent molecular probes have the advantages of high sensitivity, high time and space resolution imaging, etc., and are widely used by everyone. In recent years, molecular rotation axes have been...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B57/08C09K11/06C12Q1/02G01N21/64
Inventor 崔京南刘田宇徐兆超王静云高盼付雪田文明陈琳
Owner DALIAN UNIV OF TECH
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