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Preparation method of water-soluble chitosan-based aggregation-induced emission fluorescent probe with reduction responsiveness

A water-soluble chitosan, aggregation-induced luminescence technology, applied in fluorescence/phosphorescence, material excitation analysis, material analysis by optical means, etc., can solve the problems of small molecule fluorescent probe penetration, leakage, detection error, etc. Good reduction responsiveness and water solubility, no shift in fluorescence spectrum, and high sensitivity

Inactive Publication Date: 2018-06-05
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the AIE systems are conjugated molecules with hydrophobic aromatic nuclei, which are insoluble in physiological water environment, and small molecule fluorescent probes are easy to penetrate and leak from cells, which will cause detection errors and other problems. Therefore, water-soluble macromolecular AIE fluorescence The development of probes is of great significance

Method used

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  • Preparation method of water-soluble chitosan-based aggregation-induced emission fluorescent probe with reduction responsiveness
  • Preparation method of water-soluble chitosan-based aggregation-induced emission fluorescent probe with reduction responsiveness
  • Preparation method of water-soluble chitosan-based aggregation-induced emission fluorescent probe with reduction responsiveness

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] 1) Weigh 1g chitosan (viscosity-average molecular weight is 10,000, degree of deacetylation 60%) and join in 100mL beaker, add 0.1mol / L HCl solution of 50mL in beaker, obtain chitosan concentration after stirring evenly Solution A of 0.02g / mL;

[0024] 2) Weigh a certain amount of dithiodipropionic acid (DTDP) and add it to a three-necked flask, so that the molar ratio of DTDP to the amino group on the chitosan chain is 1:1, and then add a certain amount of 1-ethyl- (3-Dimethylaminopropyl) carbodiimide hydrochloride (EDC) and N-hydroxysuccinimide (NHS), make the molar ratio of DTDP and EDC be 1:1.2, and the molar ratio of EDC and NHS The ratio is 1:1, add an appropriate amount of anhydrous methanol to the three-necked flask to make the concentration of DTDP 0.01g / mL, and activate it in an ice bath at 0°C for 0.5h to obtain solution B;

[0025] 3) Use a constant pressure dropping funnel to add solution A dropwise to solution B, adjust the pH of the system to 4.0 with 1m...

Embodiment 2

[0032] 1) Weigh 2g chitosan (viscosity average molecular weight is 100,000, degree of deacetylation 65%) and join in 100mL beaker, add 50mL of 0.1mol / L HCl solution in beaker, obtain chitosan concentration after stirring evenly Solution A of 0.04g / mL;

[0033] 2) Weigh a certain amount of dithiodipropionic acid (DTDP) and add it to a three-necked flask so that the molar ratio of DTDP to the amino group on the chitosan chain is 1.2:1, and then add a certain amount of 1-ethyl- (3-Dimethylaminopropyl) carbodiimide hydrochloride (EDC) and N-hydroxysuccinimide (NHS), make the molar ratio of DTDP and EDC be 1:1.4, and the molar ratio of EDC and NHS The ratio is 1:1.4, add an appropriate amount of anhydrous methanol to the three-necked flask to make the concentration of DTDP 0.02g / mL, and activate it in an ice bath at 2°C for 1 hour to obtain solution B;

[0034] 3) Use a constant pressure dropping funnel to add solution A dropwise to solution B, adjust the pH of the system to 4.5 w...

Embodiment 3

[0041] 1) Weigh 0.5g chitosan (viscosity-average molecular weight is 300,000, degree of deacetylation 70%) and join in a 100mL beaker, add 50mL of 0.1mol / L HCl solution in the beaker, stir to obtain chitosan Solution A with a concentration of 0.01g / mL;

[0042] 2) Weigh a certain amount of dithiodipropionic acid (DTDP) and add it to a three-necked flask so that the molar ratio of DTDP to the amino group on the chitosan chain is 1.4:1, and then add a certain amount of 1-ethyl- (3-Dimethylaminopropyl) carbodiimide hydrochloride (EDC) and N-hydroxysuccinimide (NHS), make the molar ratio of DTDP and EDC be 1:1.6, and the molar ratio of EDC and NHS The ratio is 1:1.1, add an appropriate amount of anhydrous methanol to the three-necked flask to make the concentration of DTDP 0.02g / mL, and activate it in an ice bath at 1°C for 1.5h to obtain solution B;

[0043] 3) Use a constant pressure dropping funnel to add solution A dropwise to solution B, adjust the pH of the system to 4.8 wi...

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Abstract

The invention discloses a preparation method of a water-soluble chitosan-based aggregation-induced emission fluorescent probe with reduction responsiveness, mainly comprising the following steps: modifying chitosan molecules by adopting a hydrochloric acid / methanol mixed solvent system and an EDC / NHS catalytic system, so as to obtain disulfide bond connected carboxylation chitosan CS-ss-COOH; marking tetraphenyl ethylene (TPE) fluorescent molecule to a CS-ss-COOH chain to obtain TPE-CS-ss-COOH with aggregation-induced emission (AIE) characteristic. The fluorescent probe prepared according to the invention not only has good reduction responsiveness and water solubility, but also has aggregation-induced emission characteristic, and compared with conventional fluorescent probes, has the advantages of being high in sensitivity, good in photostability, free from quenching at high concentration, no drifting of fluorescence spectrum, and the like, can also realize further enhancement of the fluorescence intensity in a glutathione solution, is good in imaging effect, and is expected to be applied to the fields of tumor cell specificity tracking, cell metabolism detection, drug metabolism detection, environment monitoring and the like.

Description

technical field [0001] The invention relates to a preparation method of a water-soluble chitosan-based fluorescent probe (TPE-CS-ss-COOH) with reduction responsiveness and 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. 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. In the field of biochemical detection, the use of fluorescent probes with AIE characterist...

Claims

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Application Information

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IPC IPC(8): C08B37/08G01N21/64
CPCC08B37/003G01N21/6428
Inventor 王征科杨玲方雯胡巧玲唐本忠
Owner ZHEJIANG UNIV
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