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A chitosan-based fluorescent probe suitable for long blood circulation and preparation method thereof

A fluorescent probe and long-circulation technology, applied in the long-circulation blood chitosan-based fluorescent probe and its preparation field, can solve the problems of cytotoxicity and other problems, achieve high sensitivity, good imaging effect, and no drift of fluorescence spectrum

Inactive Publication Date: 2018-01-30
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, fluorescent probes are mainly used in the fields of biology and medicine. However, traditional fluorescent probes face two problems: aggregation-induced quenching (ACQ) effect and cytotoxicity.

Method used

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  • A chitosan-based fluorescent probe suitable for long blood circulation and preparation method thereof
  • A chitosan-based fluorescent probe suitable for long blood circulation and preparation method thereof
  • A chitosan-based fluorescent probe suitable for long blood circulation and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] 1) in N 2 Under the atmosphere, add 1g viscosity-average molecular weight in the there-necked flask to be 10,000, the degree of deacetylation is 60% chitosan (CS) and 2.30g phthalic anhydride, add 40ml N,N-dimethylformamide ( DMF), reacted at 130°C for 5 hours, poured it into ice water to precipitate, extracted the precipitate with methanol for 24 hours after suction filtration, and dried it in vacuum at 40°C to obtain N,O-phthalylated chitosan sugar.

[0023] 2) Add 1.2g of N,O-phthalylated chitosan to a mixed solvent of 100ml N,N-dimethylformamide and water, the volume ratio of N,N-dimethylformamide to water The ratio is 95:5, heated to 120°C in a nitrogen atmosphere, and after being fully stirred, the product is placed in ice water for precipitation, filtered with suction, extracted with methanol for 24 hours, and dried under vacuum at 40°C to obtain N-phthaloyl Chitosan;

[0024] 3) 0.5g of N-phthalylated chitosan was dissolved in 30ml of N,N-dimethylacetamide so...

Embodiment 2

[0034] 1) Under N2 atmosphere, add 1g CS (viscosity average molecular weight is 10,000, deacetylation degree is 60%) and 2.30g phthalic anhydride to the there-necked flask, add 40ml DMF, react at 130°C for 5 hours, Pour it into ice water to precipitate, and after suction filtration, extract the precipitate with methanol for 24 hours, and dry it in vacuum at 40°C to obtain N,O-phthalylated chitosan;

[0035] 2) Add 1.2g of N,O-phthalylated chitosan to a mixed solvent of 100ml N,N-dimethylformamide and water, the volume ratio of N,N-dimethylformamide to water The ratio is 95:5, heated to 120°C in a nitrogen atmosphere, and after being fully stirred, the product is placed in ice water for precipitation, filtered with suction, extracted with methanol for 24 hours, and dried under vacuum at 40°C to obtain N-phthaloyl Chitosan;

[0036] 3) 0.5g of N-phthalylated chitosan was dissolved in 30ml of N,N-dimethylacetamide solution with a mass concentration of 5% lithium chloride, pre-co...

Embodiment 3

[0045] 1) in N 2 Under atmosphere, add 1g CS (viscosity-average molecular weight: 200,000, degree of deacetylation: 70%) and 2.30g phthalic anhydride to the three-necked flask, add 40ml DMF, react at 130°C for 6 hours, pour it into Precipitate in ice water, extract the precipitate with methanol for 24 hours after suction filtration, and dry under vacuum at 40°C to obtain N,O-phthalylated chitosan;

[0046] 2) Add 1.2g of N,O-phthalylated chitosan to a mixed solvent of 100ml N,N-dimethylformamide and water, the volume ratio of N,N-dimethylformamide to water The ratio is 95:5, heated to 120°C in a nitrogen atmosphere, and after being fully stirred, the product is placed in ice water for precipitation, filtered with suction, extracted with methanol for 24 hours, and dried under vacuum at 40°C to obtain N-phthaloyl Chitosan;

[0047] 3) 0.5g of N-phthalylated chitosan was dissolved in 30ml of N,N-dimethylacetamide solution with a mass concentration of 5% lithium chloride, pre-co...

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Abstract

The invention discloses a chitosan-based fluorescence probe suitable for long circulation of blood. The chitosan-based fluorescence probe has a structure as shown in formula (1). A preparing method for the chitosan-based fluorescence probe comprises the steps of grafting polyethylene glycol onto chitosan to obtain polyethylene glycol-chitosan suitable for long circulation of blood, and then marking tetraphenyl ethylene fluorescent molecules on a chitosan link to obtain the chitosan-based fluorescence probe which has an aggregation-induced emission property and is suitable for long circulation of blood. The prepared fluorescence probe has the advantages that sensitivity and light stability are high, quenching is avoided when concentration is high, and fluorescence spectrum shift is avoided, is suitable for long circulation of blood, and has broad application prospects in the fields including cell tracing, tumor diagnosis and drug metabolism detection.

Description

technical field [0001] The invention relates to a chitosan-based fluorescent probe and a preparation method thereof, in particular to a chitosan-based fluorescent probe suitable for long blood circulation with aggregation-induced luminescent properties and a preparation method thereof. Background technique [0002] As a natural polysaccharide rich in amino groups, chitosan (CS) has good biocompatibility and bioactivity, is non-toxic and easy to biodegrade, and is widely used in the field of biomedicine. However, chitosan molecules are positively charged, which can cause cytotoxicity and immune response in vivo. Modification with polyethylene glycol (PEG) to cover part of the positive charge can reduce the non-specific binding with endogenous anionic substances during blood circulation. And it can improve the water solubility of chitosan to prolong the blood circulation time of chitosan molecules, so PEGylated chitosan can realize long circulation in blood. Fluorescent probe...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/06C08B37/08
CPCC08B37/003C09K11/06C09K2211/1466
Inventor 王征科陈末童胡巧玲唐本忠
Owner ZHEJIANG UNIV
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