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Preparation method of water-soluble chitosan-base aggregation-induced light-emitting fluorescent probe

A technology of aggregation-induced luminescence and water-soluble chitosan, which is applied in the direction of luminescent materials, fluorescence/phosphorescence, chemical instruments and methods, etc., can solve the problems of cytotoxicity, achieve good water solubility, high sensitivity, and no drift of fluorescence spectrum Effect

Inactive Publication Date: 2015-09-30
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, traditional fluorescent probes face two problems: aggregation-induced quenching (ACQ) effect and cytotoxicity.

Method used

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  • Preparation method of water-soluble chitosan-base aggregation-induced light-emitting fluorescent probe
  • Preparation method of water-soluble chitosan-base aggregation-induced light-emitting fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] 1) Weigh 1g of chitosan (viscosity average molecular weight 10,000, deacetylation degree 60%) into eggplant-shaped bottle, add 10mL DMSO, swell at 50°C for 24h, then add TPEITC, TPEITC and The mol ratio of amino group in the chitosan is 1%, reacts 24h, obtains solution A and it is poured in the 250mL beaker;

[0016] 2) Add 200mL of absolute ethanol to solution A, stir evenly, let it stand until the solution is separated, remove the supernatant, and after centrifugation, dissolve the precipitate with 40mL of acetic acid solution with a volume fraction of 2%, and filter to obtain the filtrate;

[0017] 3) Mix tetrahydrofuran and deionized water at a volume ratio of 1:1 to prepare a dialysate, put the filtrate into a dialysis bag with a molecular weight cut-off of 3500 and place it in the dialysate for dialysis for 5 days. NaOH neutralized the filtrate, centrifuged, washed with water and freeze-dried to obtain fluorescently labeled chitosan TPE-CS;

[0018] 4) Weigh 0.5g...

Embodiment 2

[0021] 1) Weigh 1g chitosan (viscosity-average molecular weight 10,000, deacetylation degree 60%) into eggplant-shaped bottle, add 10mL DMSO, swell at 55°C for 24h, then add TPEITC, TPEITC and The mol ratio of amino group in chitosan is 5%, reacts 24h, obtains solution A and it is poured in the 250mL beaker;

[0022] 2) Add 200mL of absolute ethanol to solution A, stir evenly, let it stand until the solution is separated, remove the supernatant, and after centrifugation, dissolve the precipitate with 40mL of acetic acid solution with a volume fraction of 2%, and filter to obtain the filtrate;

[0023] 3) Mix tetrahydrofuran and deionized water at a volume ratio of 1:1 to prepare a dialysate, put the filtrate into a dialysis bag with a molecular weight cut-off of 3500 and place it in the dialysate for dialysis for 5 days. NaOH neutralized the filtrate, centrifuged, washed with water and freeze-dried to obtain fluorescently labeled chitosan TPE-CS;

[0024] 4) Weigh 0.5g TPE-CS...

Embodiment 3

[0027] 1) Weigh 1g of chitosan (viscosity-average molecular weight: 100,000, deacetylation degree: 80%) into an eggplant-shaped bottle, add 10mL DMSO, swell at 55°C for 36h, then add TPEITC, TPEITC and The mol ratio of amino group in chitosan is 10%, reacts 24h, obtains solution A and it is poured in the 250mL beaker;

[0028] 2) Add 200mL of absolute ethanol to solution A, stir evenly, let it stand until the solution is separated, remove the supernatant, and after centrifugation, dissolve the precipitate with 40mL of acetic acid solution with a volume fraction of 2%, and filter to obtain the filtrate;

[0029] 3) Mix tetrahydrofuran and deionized water at a volume ratio of 1:1 to prepare dialysate, put the filtrate into a dialysis bag with a molecular weight cut-off of 3500 and place it in the dialysate for dialysis for 6 days. NaOH neutralized the filtrate, centrifuged, washed with water and freeze-dried to obtain fluorescently labeled chitosan TPE-CS;

[0030] 4) Weigh 0.5...

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Abstract

The invention discloses a preparation method of a water-soluble chitosan-base aggregation-induced light-emitting fluorescent probe, which mainly comprises the following steps: marking a tetraphenyl ethylene (TPE) fluorescent molecule to a chitosan chain to obtain TPE-CS; and carrying out succinylation modification on the TPE-CS by using an acetic acid / methanol mixed solvent system to obtain the TPE-N-CS. The fluorescent probe has favorable water solubility and aggregation-induced light-emitting characteristic, and has the advantages of high sensitivity, favorable light stability, no quenching under high-concentration conditions, no fluorescence spectrum drift, favorable imaging effect and the like as compared with the traditional fluorescent probe. The fluorescent probe is hopeful to be applied to the fields of cell tracing, drug metabolism detection, environmental monitoring and the like.

Description

technical field [0001] The invention relates to a preparation method of a water-soluble chitosan-based fluorescent probe with aggregation-induced luminescent properties. Background technique [0002] Fluorescent probes use fluorescent substances as indicators, and under the excitation of a certain wavelength of light, the indicator will produce fluorescence, and the qualitative or quantitative analysis of the detected substance can be realized by detecting the generated fluorescence. At present, fluorescent probes are mainly used in the fields of biology, medicine and environmental monitoring, so water-soluble fluorescent probes have a wide range of application values. However, traditional fluorescent probes face two problems: aggregation-induced quenching (ACQ) effect and cytotoxicity. The discovery of aggregation-induced emission (AIE) fluorescent molecules undoubtedly provides a way to solve the above problems. The AIE effect makes fluorescent probes easy to use, and th...

Claims

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Application Information

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IPC IPC(8): C08B37/08C09K11/06G01N21/64
Inventor 王征科刘亚蓝胡巧玲唐本忠
Owner ZHEJIANG UNIV
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