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L-cysteine fluorescent probe based on conjugated polymer/metal ion compound and preparation method and application thereof

A conjugated polymer, metal ion technology, applied in the field of fluorescence sensing and detection, can solve problems such as poor solubility and limited in-situ detection performance, and achieve high selectivity, low toxicity, biocompatibility, and good water solubility.

Inactive Publication Date: 2018-10-16
TIANJIN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, such fluorescent probes currently reported are usually derivatives of organic dyes, such as coumarin, fluorescein, naphthol, anthracene, bipyridine, etc., which usually have poor solubility in water, so the detection of Cys must be performed in It is carried out in an organic solvent or a mixed system of organic solvent / water, which greatly limits its in situ detection performance in biological systems

Method used

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  • L-cysteine fluorescent probe based on conjugated polymer/metal ion compound and preparation method and application thereof
  • L-cysteine fluorescent probe based on conjugated polymer/metal ion compound and preparation method and application thereof
  • L-cysteine fluorescent probe based on conjugated polymer/metal ion compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] 1.1: Synthesis of 3-methoxy-4-methylthiophene

[0032] Take 3-bromo-4-methylthiophene (2.5g, 14mmol) and dissolve it in 3.8mL NMP. After it is completely dissolved, add it to a three-necked flask filled with 20mL of 35% methanol solution of sodium methoxide, and then take nitrous bromide Copper (1.5g, 10mmol) was added to the reaction, and the reaction was refluxed for 24h under the protection of nitrogen. Cool to room temperature, filter off the solid, spin the filtrate to dryness, add dichloromethane to dissolve, and extract with water. The obtained organic phase was dried by adding anhydrous magnesium sulfate. After filtration and spin-drying, the crude product was purified by column chromatography (silica gel, n-hexane) to obtain 1.3 g of 3-methoxy-4-methylthiophene with a yield of 72.2%. 1 HNMR (400MHz, CDCl 3 ): 6.74(s,1H), 6.08(d,1H), 3.74(s,3H), 2.01(s,3H).

[0033] 1.2: Synthesis of 3-(3-bromo)propoxy-4-methylthiophene

[0034] 3-Methoxy-4-methylthiophene ...

Embodiment 2

[0044] 2.1: Synthesis of 3-methylthio-4-methylthiophene:

[0045] Take 3-bromo-4-methylthiophene (2.5g, 14mmol) and dissolve it in 3.8mL NMP. After it is completely dissolved, add it to a three-necked flask filled with 20mL of 35% sodium methylthiolate in methanethiol, and then Cuprous bromide (1.5g, 10mmol) and butyllithium (60mg, 9.3mmol) were added to the reaction, and the reaction was refluxed for 24h under the protection of nitrogen. Cool to room temperature, filter off the solid, spin the filtrate to dryness, add dichloromethane to dissolve, and extract with water. The obtained organic phase was dried by adding anhydrous magnesium sulfate. After filtration and spin-drying, the crude product was purified by column chromatography (silica gel, n-hexane) to obtain 1.05 g of 3-methylthio-4-methylthiophene with a yield of 51.7%. 1 HNMR (400MHz, CDCl 3 ): 6.73(s,1H), 6.71(d,1H), 2.74(s,3H), 2.21(s,3H).

[0046] 2.2: Synthesis of 3-(3-bromo)propylthio-4-methylthiophene

[0...

Embodiment 3

[0057] 3.1: Synthesis of 3-(3-bromo)propylthiophene

[0058] Add 3-(3-thienyl)-1-propanol (1.5g, 10mmol) and phosphorus tribromide (2.7g, 10mmol) into a three-necked flask containing 30mL of chloroform solution, and fully stir the reaction under nitrogen protection for 24h . After suction filtration, the filtrate was spin-dried, and the crude product was purified by column chromatography (silica gel, n-hexane) to obtain 1.5 g of 3-(3-bromo)propylthiophene with a yield of 75.3%. 1 HNMR (400MHz, CDCl 3 ):7.06(d,1H),6.75(d,1H),6.73(s,1H),3.63(m,2H),3.05(m,2H).

[0059] 3.2: Synthesis of 3-(3-N,N'-diethyl diacetate)propylthiophene

[0060] 3-(3-bromo)propylthiophene (1.5g, 7.85mmol), diethyl iminodiacetate (1.85g, 9.75mmol), K 2 CO 3 (0.80g, 5.80mmol) and KI (0.16g, 0.98mmol) were added to 30mL of a mixed solution of tetrahydrofuran and acetonitrile (1:1, v / v), and reacted at 85°C for 48h under the protection of nitrogen. After cooling to room temperature, the solvent was sp...

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Abstract

The invention provides an L-cysteine fluorescent probe based on a conjugated polymer / metal ion compound and a preparation method and application thereof. The fluorescent probe is a compound formed through the conjugated polymer and metal ions, wherein the conjugated polymer is a polythiophene derivative (PT) with the side chain containing dicarboxylate, and the structural formula is as shown in the specification. PT emits intense fluorescence in a water solution, and combines with the metal ions (M<n+>) to form the compound, and due to the paramagnetism of the metal ions, the fluorescence of the PT solution is quenched. After L-cysteine (Cys) is added, Cys and M<n+> can generate a more stable complex Cys-Mn+, acordingly PT is released from the PT / Mn+ compound, and the fluorescence is restored. The PT / M<n+> compound fluorescent probe is simple in synthesis method, good in water solubility, high in response speed, high in selectivity, can be used for quantitative detection of Cys in thewater solution, and can be used for labeling and fluorescence imaging of Cys in living cells.

Description

technical field [0001] The invention belongs to the technical field of fluorescent sensing and detection, and in particular relates to an L-cysteine ​​fluorescent probe based on a conjugated polymer / metal ion complex and its preparation method and application. Background technique [0002] L-cysteine ​​(Cys) is a very important thiol-containing amino acid in the human body. It can participate in the reversible oxidation-reduction reaction process in the human body, and has many important physiological functions such as regulating cell homeostasis and cell metabolism in biochemical pathways. Function. Abnormal concentration of Cys in organisms can cause many diseases. Low levels of Cys can cause symptoms such as growth retardation, hair pigment loss, lethargy, liver and skin tissue damage, and fat loss in children; while atherosclerosis, ischemic cerebrovascular disease, hypertension syndrome, and gestational diabetes And other diseases are accompanied by a significant incr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): G01N21/64C08G61/12C09K11/06
CPCC08G61/126C08G2261/11C08G2261/3223C09K11/06C09K2211/1458G01N21/6428G01N2021/6439
Inventor 陆燕刘丽华王晶张强赵琳琳
Owner TIANJIN UNIVERSITY OF TECHNOLOGY