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Photo-thermal dual-responsiveness chitosan derivative as well as preparation method and application thereof

A technology of chitosan derivatives and photoresponsiveness, which is applied in the fields of pharmaceutical formulation, drug delivery, and photodisintegration of drugs in vivo, and can solve the problem of microencapsulated emulsions and light sources that are not suitable for embedding bioactive drugs and plant essential oils. The sensitivity needs to be improved, the preparation method is complicated, etc., and the preparation process is easy to scale up, the preparation process is gentle, and the particle size is uniform.

Active Publication Date: 2020-08-14
SOUTH SUBTROPICAL CROPS RES INST CHINESE ACAD OF TROPICAL AGRI SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The above-mentioned prior art all is to modify chitosan or carboxymethyl chitosan, and the modified sites all introduce different functional monomer molecules on the nitrogen position, so that the modified polymer has a certain Environmental responsiveness, but the above-mentioned carrier material has a low drug loading, and the sensitivity to external environmental light sources needs to be improved; and the preparation method of the above-mentioned carrier is complicated and the steps are cumbersome
[0006] In addition, most of the existing nano-microcapsule preparation technologies are obtained through high-speed shear emulsification, and high shear force easily leads to demulsification, making the prepared emulsion uneven, and the microspheres made of emulsion are also uneven, which is not suitable for the preparation of Microencapsulated Emulsions Encapsulating Biologically Active Drugs and Plant Essential Oils

Method used

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  • Photo-thermal dual-responsiveness chitosan derivative as well as preparation method and application thereof
  • Photo-thermal dual-responsiveness chitosan derivative as well as preparation method and application thereof
  • Photo-thermal dual-responsiveness chitosan derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068] The preparation of the photothermal sensitive type carboxymethyl chitosan nano-microcapsule loaded with Abamectin in this embodiment comprises:

[0069] (1) Preparation of photothermally sensitive carboxymethyl chitosan derivatives

[0070] ① Take 0.0025mol o-nitrobenzyl alcohol (0.3825g) and 0.0025mol tungalic anhydride (0.94g) respectively and dissolve them in 100mL chloroform solution, add appropriate amount of 4-dimethylaminopyridine (DMAP), under nitrogen protection environment, Reflux reaction at 60°C for 12 hours, part of the chloroform was distilled off under reduced pressure, and then the mixture obtained in the reflux reaction was cooled to room temperature, washed, extracted, and dried to obtain o-nitrobenzyl tungalic anhydride.

[0071] ②At room temperature, mix 0.270g 1-hydroxyl-benzotriazole (HOBt), 1.2g 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (EDC), 2mmol tungalic anhydride ortho Nitrobenzyl ester was dissolved in 50mL of ethanol solution; then the...

Embodiment 2

[0085] The preparation method of the photothermal-sensitive type carboxymethyl chitosan nano-capsule of the load tea tree essential oil of the present embodiment comprises:

[0086] (1) Preparation of photothermally sensitive carboxymethyl chitosan derivatives

[0087] ① Weigh 0.0025mol o-nitrobenzyl alcohol (0.3825g) and 0.0025mol tungalic anhydride (0.94g) and dissolve them in 500mL ethyl acetate solution, add appropriate amount of 4-dimethylaminopyridine (DMAP), nitrogen protection environment Under reflux at 50°C for 24 hours, part of the ethyl acetate was distilled off under reduced pressure, and then the resulting mixture was cooled to room temperature, washed, extracted, and dried to obtain o-nitrobenzyl tungalic anhydride.

[0088]②At room temperature, dissolve 0.270g of 1-hydroxy-benzotriazole (HOBt), 1.2g of dicyclohexylcarbodiimide (DCC), and 2mmol of o-nitrobenzyl tungalic anhydride in 50mL of ethanol solution; then The above solution was added dropwise to 500 mL ...

Embodiment 3

[0098] The preparation method of the photothermal-sensitive type carboxymethyl chitosan nano-microcapsule of load patchouli essential oil of the present embodiment comprises:

[0099] (1) Preparation of photothermally sensitive carboxymethyl chitosan derivatives

[0100] ① Weigh 0.0025mol o-nitrobenzyl alcohol (0.3825g) and 0.0025mol tungalic anhydride (0.94g) and dissolve them in 500mL ethyl acetate solution, add appropriate amount of 4-dimethylaminopyridine (DMAP), nitrogen protection environment Under reflux at 50°C for 24 hours, part of the ethyl acetate was distilled off under reduced pressure, and then the resulting mixture was cooled to room temperature, washed, extracted, and dried to obtain o-nitrobenzyl tungalic anhydride.

[0101] ②At room temperature, add 0.270g of benzotriazole-N,N,N',N'-tetramethyluronium hexafluorophosphate (HBTU), 1.2g of 1-(3-dimethylaminopropyl)- 3-Ethylcarbodiimide (EDC), 2mmol tungalic anhydride o-nitrobenzyl ester were dissolved in 50mL o...

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Abstract

The invention relates to the technical field of polymer materials, in particular to a photo-thermal dual-responsiveness chitosan derivative of which the structural formula is shown as a formula (I) shown in the specification. In the formula, x, y, z and n are natural numbers greater than or equal to 1, and m is a natural number greater than or equal to 0. The invention also provides nano-microcapsules, which take the photo-thermal dual-responsiveness chitosan derivative shown in the formula (I) as a wall material, take a bioactive drug or plant essential oil as a core material, and adopt a method of a rapid membrane emulsification instrument to embed the core material in the wall material through intermolecular force and electrostatic attraction of the wall material, so as to form a core-shell structure. According to the photo-thermal dual-responsiveness chitosan derivative disclosed by the invention, a tung oil-based derivative that is eleocharic anhydride is used as a connecting arm,which has characteristics of being renewable and green; meanwhile, tung maleic anhydride contains unsaturated double bonds, the double bonds are sensitive to an external environment light source andcan be subjected to a photochemical reaction, and tung maleic anhydride itself can be used as a photoresponse group so as to increase the sensitivity of a carrier material to the external environmentlight source.

Description

technical field [0001] The invention relates to the technical field of polymer materials, in particular to a chitosan derivative with dual photothermal responsiveness, its preparation method and application. Background technique [0002] Sensitive carrier is a kind of carrier material that can respond to external physical and chemical stimuli (light, ultrasound, magnetic field, pH, temperature, etc.), and then change its structure and performance. Using the characteristics of its responsive group, it can realize Smart release of drugs. [0003] In the prior art, Guo Jingjing (Preparation and Research of Photoresponsive Carboxymethyl Chitosan Nanocapsules [D]. Wuhan University of Technology. 2014.) uses carboxymethyl chitosan as raw material and succinic anhydride as connecting arm, A light-responsive carboxymethyl chitosan derivative was prepared by using the o-nitrobenzyl group as the photoresponsive group, in which the linker succinic anhydride was grafted to the C2-NH in...

Claims

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Application Information

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IPC IPC(8): C08F251/00C08F220/54C08B37/08A61K9/00A61K41/00A61K47/36A61K47/61
CPCC08F251/00C08B37/003A61K47/36A61K47/61A61K9/0009A61K41/0042C08F220/54
Inventor 周闯李普旺杨子明谢江辉何祖宇王超焦静吕明哲宋书会刘运浩
Owner SOUTH SUBTROPICAL CROPS RES INST CHINESE ACAD OF TROPICAL AGRI SCI
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