PH-responsive conjugated polymer nanoparticles, preparation method and applications thereof

A technology of polythiophene derivatives and products, applied in the field of fluorescence sensing and detection, can solve the problems of small displacement of stocks, inability to track and observe, poor photostability of probes, etc., and achieve the effects of high accuracy, low toxicity and mild conditions.

Active Publication Date: 2020-05-12
TIANJIN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the currently reported pH probes are based on small-molecule fluorescent dyes. These probes have poor photostability, small stocks shift, low sensitivity, poor water solubility, and high toxicity. They cannot track and observe changes in pH for a long time.

Method used

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  • PH-responsive conjugated polymer nanoparticles, preparation method and applications thereof
  • PH-responsive conjugated polymer nanoparticles, preparation method and applications thereof
  • PH-responsive conjugated polymer nanoparticles, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] The preparation method of poly 3-(3-N, N'-diethyl) propoxy-4-methylthiophene, comprises the following steps:

[0057] Step 1, add 3-bromo-4-methylthiophene (2.5g, 14mmol) into 3.8mL NMP (N-methylpyrrolidone), and after it is completely dissolved, solution A is obtained, and solution A is added to 20mL containing methanol Sodium in methanol solution to obtain solution B, add cuprous bromide (1.5g, 10mmol) to solution B, reflux reaction under nitrogen protection for 24h, obtain solution C; cool solution C to room temperature 20-25°C, filter , spin the filtrate to dryness, then add 30 mL of dichloromethane to dissolve, wash with water 3 times to obtain the first organic phase liquid, add anhydrous magnesium sulfate to the first organic phase liquid to dry the first organic phase liquid, filter, The first organic phase liquid is spin-dried to obtain product D as a crude product, wherein the structural formula of 3-bromo-4-methylthiophene is:

[0058] In step 1, the produ...

Embodiment 2

[0065] The preparation method of poly 3-(4-N, N'-diethyl) butylthio-4-methylthiophene, comprises the following steps:

[0066] Step 1, add 3-bromo-4-methylthiophene (2.5g, 14mmol) into 3.8mL NMP (N-methylpyrrolidone), and after being completely dissolved, solution A is obtained, and solution A is added to 20mL containing formazan In the methanol solution of sodium thiolate, solution B was obtained, and cuprous bromide (1.5g, 10mmol) and butyllithium (60mg, 9.3mmol) were added to solution B, and reflux reaction was carried out under nitrogen protection for 24h to obtain solution C; Cool solution C to room temperature 20-25°C, filter, spin the filtrate to dryness, add 30 mL of dichloromethane to dissolve, wash with water 3 times to obtain the first organic phase liquid, add anhydrous magnesium sulfate to the first organic phase liquid, For drying the first organic phase liquid, filter, and spin dry the first organic phase liquid to obtain product D as a crude product, wherein th...

Embodiment 3

[0074] The preparation method of poly 3-(5-N, N'-dimethyl)pentylthiophene comprises the following steps:

[0075] Step 1, 3-bromothiophene (2.5g, 15.3mmol) was added to 3.8mL NMP (N-methylpyrrolidone), and after being dissolved, solution A was obtained, and solution A was added to 20mL methanol containing sodium methylthiolate In solution, obtain solution B, in solution B, add cuprous bromide (1.5g, 10mmol) and butyllithium (60mg, 9.3mmol), reflux reaction 24h under nitrogen protection, obtain solution C; Solution C is cooled to Room temperature 20-25°C, filter, spin the filtrate to dry, then add 30mL dichloromethane to dissolve, wash 3 times with water to obtain the first organic phase liquid, add anhydrous magnesium sulfate to the first organic phase liquid to dry the second organic phase liquid An organic phase liquid, filtered, and the first organic phase liquid was spin-dried to obtain product D;

[0076] After step 1, the product D as a crude product was purified by col...

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Abstract

The invention discloses pH-responsive conjugated polymer nanoparticles, a preparation method and applications thereof. The preparation method comprises the following steps: uniformly mixing ultrapurewater and anhydrous acetonitrile to obtain a mixed solution; keeping the mixed solution in an ultrasonic state at a temperature of 20-35 DEG C, adding a mother liquor into the mixed solution in a dropwise manner, and continuously carrying out ultrasonic treatment for 1-2 hours after dropwise adding is completed to obtain a solution M, wherein the preparation method of the mother liquor comprises the following steps: dissolving a polythiophene derivative in chloroform to obtain a polythiophene derivative mother liquor with a concentration of 1-2 mg/mL; and introducing nitrogen into the solutionM, and removing chloroform and acetonitrile to obtain the pH-responsive conjugated polymer nanoparticle aqueous solution. The pH-response conjugated polymer nanoparticle has the characteristics of good biocompatibility, high fluorescence intensity, low toxicity and the like, can be used for accurately measuring the weakly acidic pH value in an aqueous solution, and can also be used for sensitivedetection and fluorescence imaging of tumor cell microenvironment response.

Description

technical field [0001] The invention belongs to the technical field of fluorescence sensing and detection, and specifically relates to a pH-responsive conjugated polymer nanoparticle and a preparation method and application thereof. Background technique [0002] Intracellular pH plays a vital role in many physiological processes such as cell proliferation and apoptosis, ion transport, enzyme activity, endocytosis, and muscle contraction. The cytoplasmic pH of normal cells is 6.8-7.4, and the pH of acidic organelles is 4.5-6.0. Abnormal pH can cause cell dysfunction, lead to heart, lung disease or neurological diseases, and even life-threatening. Therefore, accurate monitoring of changes in intracellular pH can provide important parameters for physiological, pharmacological, and pathological studies. At present, the measurement of pH value usually uses a commercial glass electrode, which is not suitable for the monitoring of pH value in living cells. Fluorescence analysis ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12C09K11/06G01N21/64
CPCC08G61/126C09K11/06G01N21/6428C08G2261/143C08G2261/11C08G2261/18C08G2261/145C08G2261/3223C08G2261/522C08G2261/90C09K2211/1092
Inventor 陆燕刘立霞张强王晶刘丽华
Owner TIANJIN UNIVERSITY OF TECHNOLOGY
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