Quaternized chitosan fluorescent probe with aggregation-induced emission property and preparation method thereof

A technology of quaternized chitosan and aggregation-induced luminescence, which is applied in chemical instruments and methods, luminescent materials, fluorescence/phosphorescence, etc., can solve the problems of dye leakage, cytotoxicity, etc., and achieve excellent water solubility, fluorescence spectrum does not drift, Good biocompatibility effect

Inactive Publication Date: 2017-04-26
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, for AIE probes used in biomedical research, dye leakage and cytotoxicity are two major problems that cannot be ignored

Method used

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  • Quaternized chitosan fluorescent probe with aggregation-induced emission property and preparation method thereof
  • Quaternized chitosan fluorescent probe with aggregation-induced emission property and preparation method thereof
  • Quaternized chitosan fluorescent probe with aggregation-induced emission property and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] 1) Take by weighing 1g chitosan (viscosity-average molecular weight is 10,000, degree of deacetylation 60%) joins in the flask of 50ml, add 20ml volume fraction and be 1% acetic acid solution, stir and dissolve, obtain chitosan concentration and be 50mg / mL of solution A;

[0021] 2) Take 0.453ml of 2,3-epoxypropyltrimethylammonium chloride, add the same volume of triple distilled water, and prepare solution B;

[0022] 3) Warm up solution A to 45°C, drop solution B into solution A, make the molar ratio of GTA to amino groups in chitosan 1:1, react for 6 hours, and obtain solution C;

[0023] 4) Solution C is packed into a dialysis bag with a molecular weight cut-off of 3500 and placed in three-distilled water for dialysis for 2 days, and freeze-dried to obtain water-soluble quaternized chitosan TMC;

[0024] 5) Weigh 0.1g of TMC obtained in step 4) and disperse it in 10ml of DMSO, swell at 50°C for 10h, then add 1mg of TPEITC to the solution to make the mole of amino ...

Embodiment 2

[0029] 1) Take by weighing 1g chitosan (viscosity-average molecular weight is 190,000, deacetylation degree 68%) joins in the flask of 50ml, add 25ml volume fraction and be 1% acetic acid solution, stir and dissolve, obtain chitosan concentration and be 40mg / mL of solution A;

[0030] 2) Take 0.785ml of 2,3-epoxypropyltrimethylammonium chloride, add the same volume of triple distilled water, and prepare solution B;

[0031] 3) The temperature of solution A was raised to 55° C., and solution B was slowly added dropwise into solution A, so that the molar ratio of GTA to chitosan amino groups was 1.5:1, and reacted for 6 hours to obtain solution C;

[0032] 4) Solution C is packed into a dialysis bag with a molecular weight cut-off of 8000 and placed in three-distilled water for dialysis for 3 days, and freeze-dried to obtain water-soluble quaternized chitosan TMC;

[0033] 5) Weigh 0.1g of TMC obtained in step 4) and disperse it in 10ml of DMSO, swell at 55°C for 8h, then add ...

Embodiment 3

[0038] 1) Take by weighing 1g chitosan (viscosity-average molecular weight is 530,000, degree of deacetylation 74.5%) joins in the flask of 100ml, add 50ml volume fraction and be 1.5% acetic acid solution, stir and dissolve, obtain chitosan concentration and be 20mg / mL of solution A;

[0039] 2) Take 1.164ml of 2,3-epoxypropyltrimethylammonium chloride, add the same volume of triple distilled water, and prepare solution B;

[0040] 3) Warm up solution A to 65°C, drop solution B into solution A so that the molar ratio of GTA to amino groups in chitosan is 2:1, and react for 15 hours to obtain solution C;

[0041] 4) The solution C is packed into a dialysis bag with a molecular weight cut-off of 14000 and placed in three-distilled water for dialysis for 3 days, and freeze-dried to obtain water-soluble quaternized chitosan TMC;

[0042] 5) Weigh 0.1g of TMC obtained in step 4) and disperse it in 10ml of DMSO, swell at 60°C for 8h, then add 6.6mg of TPEITC to the solution to mak...

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Abstract

The invention discloses a quaternized chitosan fluorescent probe with the aggregation-induced emission property. A preparation method of the probe mainly comprises the steps that 2,3-glycidyl trimethyl ammonium chloride (GTA) is inoculated onto a chitosan chain to obtain quaternized chitosan (TMC) with excellent water solubility; tetraphenylethylene (TPE) fluorescent molecules are marked on TMC to obtain TPE-TMC with the aggregation-induced emission (AIE) property. The prepared fluorescent probe has the excellent water solubility and the aggregation-induced emission property, and has the advantages of being high in sensitivity and good in light stability and not drifting in fluorescence spectrum compared with a traditional fluorescent probe. In addition, due to the intrinsic property of quaternized chitosan, and the probe has a positive charge, has the good water solubility and biocompatibility, and is expected to be used for the fields of periodic cell tracing, pathological monitoring, drug metabolism detection and the like.

Description

technical field [0001] The invention relates to a quaternized chitosan fluorescent probe with aggregation-induced luminescent properties and a preparation method thereof. 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, medical diagnosis, and environmental monitoring. With the development of science and technology, probes for different needs have emerged as the times require. Generally speaking, it can be divided into three categories: traditional fluorescent probes, inorganic quantum dot probes, and new fluorescent probes. Among them, traditional fluorescent probes were first developed and applied, but they have defects such as photoins...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/08C09K11/06G01N21/64
CPCC08B37/003C09K11/06C09K2211/1425C09K2211/145G01N21/6428G01N2021/6439
Inventor 王征科刘亚蓝乔丰慧胡巧玲唐本忠
Owner ZHEJIANG UNIV
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