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Perylene-based small molecular fluorescent probe and preparation method and application thereof

A fluorescent probe and small molecule technology, applied in the field of perylene-based small molecule fluorescent probe and its preparation, can solve the problems of poor photobleaching resistance, high detection cost, high biological toxicity, etc., and achieve selective biological low toxicity, selective Good performance and high sensitivity

Active Publication Date: 2017-11-24
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these methods have defects such as high detection cost, poor selectivity, low sensitivity, poor resistance to photobleaching, and high biological toxicity.

Method used

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  • Perylene-based small molecular fluorescent probe and preparation method and application thereof
  • Perylene-based small molecular fluorescent probe and preparation method and application thereof
  • Perylene-based small molecular fluorescent probe and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] The preparation process of the small molecule fluorescent probe of this embodiment mainly includes the following steps:

[0058] 1. Place 0.5g (2mmol) of perylene and 40mL of 1,4-dioxane in a double-necked flask in sequence, and stir at 80°C until the perylene is completely dissolved into a clear yellow solution; then slowly inject 1mL of concentrated Nitric acid, concentrated nitric acid concentration is 65%~68% concentrated nitric acid (14.4~15.2mol / L), after stirring at 60 ℃ for 30min, obtain the reaction solution comprising compound 1 and compound 2; Pour into a large amount of ice water, filter under reduced pressure and vacuum dry for 12 hours to obtain a bright red crude product; finally, use petroleum ether (PE)-dichloromethane (DCM) with a volume ratio of 1.5:1 as the eluent by chromatography The dark red needle-like solid compound 1 (yield 20%) and brick red solid compound 2 (yield 63%) were obtained.

[0059] Its chemical reaction formula is as follows:

[...

Embodiment 2

[0085] Compound 5 and compound 6 were named as fluorescent probes 1-NH-MA and 3-NH-MA respectively, and then both were prepared with DMSO at a concentration of 10 -5 mol / L probe solution; then, add cysteine ​​solution (Cys) with the same concentration as the probe to the two probe solutions respectively; finally, use a UV-visible spectrophotometer to detect its absorbance. The result is as figure 1 and figure 2 As shown, the absorptions of probes 1-NH-MA and 3-NH-MA are both located between 350nm and 480nm, and the absorption wavelength and absorption intensity of the probes have almost no change before and after adding cysteine.

Embodiment 3

[0087] Compound 5 and compound 6 were named as fluorescent probes 1-NH-MA and 3-NH-MA respectively, and then both were prepared with DMSO at a concentration of 10 -5 mol / L probe solution; then, add cysteine ​​solution (Cys) with different concentrations respectively to two kinds of probe solutions, test the impact of Cys on the fluorescence intensity of the probe, it is found through testing that when the Cys concentration is 1×10 -5 mol / L, the probe has the strongest luminescence intensity. Such as image 3 and Figure 4 As shown, the probes 1-NH-MA and 3-NH-MA themselves do not emit light or emit light relatively weakly, adding Cys(10 -5 mol / L) immediately after the obvious fluorescence enhancement, the fluorescence intensity of 1-NH-MA and 3-NH-MA was enhanced by 71 times and 196 times after Cys was added, indicating that the two fluorescent probes provided in this example have relatively high High sensitivity.

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Abstract

The invention belongs to the technical field of sulfhydryl biological small molecule detection, in particular to a perylene-based small molecular fluorescent probe and a preparation method and application thereof. The preparation method comprises the following steps: first performing a nitration reaction on 1-position carbon or 3-position carbon of perylene so as to connect a nitro group, then reducing the nitro group into an amino group, then replacing the amino group with maleic anhydride so as to obtain two small molecular fluorescent probes adopting novel structures, provided by the invention, wherein the two small molecular fluorescent probes adopts the chemical structural formulae shown as a formula (I) or a formula (II). When the small molecular fluorescent probe is combined with a sulfhydryl biological small molecule in a biological cell, green light is emitted, which is significantly different from background blue light of the biological cell; the small molecular fluorescent probe has the advantages of high sensitivity, good selectivity and low biological toxicity; in addition, the preparation process is simple and optimized, and the detection cost of the sulfhydryl biological small molecule is greatly reduced.

Description

technical field [0001] The invention belongs to the technical field of sulfhydryl biological small molecule detection, and in particular relates to a perylene-based small molecule fluorescent probe and a preparation method and application thereof. Background technique [0002] The thiol biomolecules include cysteine, homocysteine ​​and reduced glutathione, etc., mainly through the thiol-SH to play a physiological role, and the sulfhydryl group (-SH) is the most chemically active group in the cell . Due to the strong coordination ability and reducibility of sulfhydryl groups, they can combine with heavy metal ions, or remove active oxygen in the human body, and play an important role in the antioxidant system of cells, which can be used to maintain the normal physiological activity of biological cells and protect Small molecular compounds that protect cells from foreign substances. As a kind of essential amino acid for cells, sulfhydryl biomolecules play an important role i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/448C09K11/06G01N21/64
CPCC07D207/448C09K11/06C09K2211/1011C09K2211/1029G01N21/6428
Inventor 籍少敏董方帝赖辉燕陈国静梁辉霍延平王华倩
Owner GUANGDONG UNIV OF TECH
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