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Dual-channel berberine-based fluorescent probe for detecting Hg<2+>/ClO<-> as well as preparation method and application thereof

A fluorescent probe, berberine technology, applied in fluorescence/phosphorescence, chemical instruments and methods, material analysis through optical means, etc., can solve problems such as weak fluorescence performance

Active Publication Date: 2020-06-16
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Although berberine can be used as a precursor for the synthesis of organic fluorescent probes, due to its weak fluorescence in aqueous solution, it is necessary to add clathrates or fluorescein to achieve the indication of fluorescence changes

Method used

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  • Dual-channel berberine-based fluorescent probe for detecting Hg&lt;2+&gt;/ClO&lt;-&gt; as well as preparation method and application thereof
  • Dual-channel berberine-based fluorescent probe for detecting Hg&lt;2+&gt;/ClO&lt;-&gt; as well as preparation method and application thereof
  • Dual-channel berberine-based fluorescent probe for detecting Hg&lt;2+&gt;/ClO&lt;-&gt; as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Embodiment 1 Preparation of novel dual-channel berberine-based fluorescent probe

[0027] The reaction formula is:

[0028]

[0029] Specific steps are as follows:

[0030] 10-Methoxy-5,6-dihydro-9H-[1,3]dioxole[4,5-g]isoquinolino[3,2-α]isoquinoline- The preparation of 9-ketone (compound 2): add 20.0g berberine hydrochloride in the round bottom flask of 250mL, and the round bottom flask is placed in the oil bath, connect one end of the ground suction joint to the round bottom flask, and the other end Connect the circulating vacuum water pump, slowly raise the temperature to 185°C, wait until the yellow berberine is completely converted into red berberine, the experiment is over, and the reaction time is 30-60 minutes; the reaction system is recrystallized 3 times with anhydrous methanol to obtain a red color Solid berberine, the yield is 75.7%; 1 H NMR (400MHz, Methanol-d 4 )δ:9.24(s,1H),7.96(s,1H),7.50(d,J=8.0Hz,1H),7.40(s,1H),6.85(d,J=9.0Hz,2H),6.05( s, 2H), 4...

Embodiment 2

[0035] A certain amount of compound 5 was dissolved in CH 3 In the mixed solvent of OH / PBS (V / V=7:3), the configuration is 1×10 -5 M, the solution is yellow and transparent, with Hg 2+ (1×10 -4 M) and ClO - (1×10 -4 M) adding, the solution system becomes pale yellow and colorless rapidly respectively, observes under daylight as figure 1 shown.

Embodiment 3

[0037] A certain amount of compound 5 was dissolved in CH 3 In the mixed solvent of OH / PBS (V / V=7:3), the configuration is 1×10 -5 M, respectively add 10eq of Hg 2+ 、K + 、Na + , Ca 2+ , Fe 2+ 、Cr 3+ , Zn 2+ , Mg 2+ 、Ni 2+ 、Co 2+ 、Cu 2+ , ClO - , Cl - 、Br - , I - , NO 3 - 、H 2 PO 4 - 、HS - 、HSO 3 - , S 2 o 3 2- , SO 4 2- , S 2- , SO 3 2- , CO 3 2- 、H 2 o 2 , Cys and other measured substances. The results show that( figure 2 ), adding Hg 2+ After that, the fluorescent probe showed orange-red fluorescence under 365nm ultraviolet light; adding ClO - After that, the fluorescent probe shows green fluorescence under 365nm ultraviolet light; adding other interfering substances will not cause the fluorescence of the fluorescent probe to change. This shows that compound 5 is a kind of detection Hg 2+ / ClO - A novel dual-channel fluorescent probe.

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Abstract

The invention discloses a dual-channel berberine-based fluorescent probe for detecting Hg<2+> / ClO<-> as well as a preparation method and application of the dual-channel berberine-based fluorescent probe. According to the invention, berberine is used as a raw material to prepare the dual-channel berberine fluorescent probe for detection of Hg<2+> / ClO<->. Berberine hydrochloride 1 is subjected to methoxy and chloride ion removal to obtain a ketone compound 2; the compound 2 is acidified and isomerized to obtain a phenolic compound 3; Duff formylation reaction is carried out on the compound 3 toobtain a p-hydroxy aldehyde compound 4; and the compound 4 and thiosemicarbazide are condensed to obtain a thiosemicarbazide Schiff base compound 5. The compound 5 can specifically recognize Hg<2+> and ClO<->, and the probe emits orange red fluorescence in the presence of Hg<2+> under the irradiation of 365nm ultraviolet light. In the presence of ClO<->, the probe emits green fluorescence, and inthe presence of other anions and metal ions, fluorescence does not occur. Therefore, the compound 5 can be used as a dual-channel fluorescent probe and has good application value.

Description

technical field [0001] The invention belongs to the technical field of fine organic synthesis and the technical field of synthesis of novel photoluminescent materials, and relates to a device capable of simultaneously detecting Hg 2+ / ClO - A novel dual-channel berberine-based fluorescent probe and its preparation method and application. Background technique [0002] Among various metal ions, Hg 2+ It is considered to be one of the most dangerous heavy metal ions, which can damage the function of human cells, cause heart disease, liver failure, DNA damage, kidney failure, nervous system damage and other diseases, and even endanger life; HOCl and ClO - As a disinfectant, it is widely used in the field of medicine and health. However, excessive hypochlorite can damage human DNA and protein, leading to many diseases, such as rheumatism, cardiovascular disease, atherosclerosis, Parkinson's disease and cancer. Therefore, for Hg 2+ and ClO - Real-time detection with high sele...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D455/03C09K11/06G01N21/64
CPCC07D455/03C09K11/06G01N21/643C09K2211/1033G01N2021/6439
Inventor 王石发阮树堂王忠龙张燕杨海燕杨益琴徐徐李明新
Owner NANJING FORESTRY UNIV