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Oxidoreduction sensitive sericin derivative with anti-tumor activity and preparation and application thereof

A technology of anti-tumor activity and sericin protein, which is applied in the field of redox-sensitive sericin derivatives and its preparation, to achieve enhanced killing effect, good biocompatibility, and improved anti-tumor effect

Active Publication Date: 2018-11-16
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are many deficiencies and room for improvement in the current research at home and abroad, for example, more sophisticated design for tumor microenvironment such as partial acidity, high glutathione concentration, abnormal metalloproteinase activity, etc., design of multiple response carriers to deal with complex in vivo environment, How to improve the efficacy of cancer drugs, and more

Method used

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  • Oxidoreduction sensitive sericin derivative with anti-tumor activity and preparation and application thereof
  • Oxidoreduction sensitive sericin derivative with anti-tumor activity and preparation and application thereof
  • Oxidoreduction sensitive sericin derivative with anti-tumor activity and preparation and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0054] Example 1 Preparation of Sericin-Cystamine Derivatives with Redox Responsive Properties

[0055] Disperse 5g of dry sericin powder in 50mL of ultra-dry DMSO solvent, stir until fully dissolved, the solution is clear and translucent, dissolve 12g of CDI in 20mL of dry DMSO, add dropwise to the above sericin solution in an ice bath, add dropwise After completion, the ice bath was removed, and under the protection of nitrogen, the reaction was stirred at room temperature for 12 h, and 10 mL of deionized water was added to quench unreacted CDI. Add the above-mentioned sericin solution into 50 mL of cystamine (15 g) aqueous solution in an ice bath, remove the ice bath and continue the reaction for 12 hours. After the reaction, dialyze in pure water to remove organic solvents and water-soluble impurities (the molecular weight cut-off of the dialysis bag is 5000 Da), freeze Dry to obtain sericin-cystamine derivative (Ser-SS).

[0056] pass 1 The structure of the correspondin...

Embodiment 2

[0057] Example 2 Preparation of Redox Sensitive Sericin-Vitamin E Succinate Derivatives

[0058] Dissolve 100mg (0.19mmol) of vitamin E succinate in 20mL of anhydrous dichloromethane, add 30mg of triphosgene (0.10mmol), 100μL of DMF, and react in the dark at 25°C for 6h. After the reaction, the organic solvent is distilled off under reduced pressure. Obtain oily matter, i.e. vitamin E succinate acid chloride derivative; dissolve vitamin E succinate acid chloride derivative with 10mL anhydrous DMSO, obtain the DMSO solution of vitamin E succinate acid chloride derivative; 500mg silk prepared in Example 1 Colloid-cystamine derivatives, dissolved in 15 mL of ultra-dry DMSO, added 0.2 mL (0.001 mmol) of ultra-dry triethylamine and 2 mg (0.016 mmol) of dimethylaminopyridine, added 1, 2.5, 5 mL of the above vitamin E The DMSO solution of succinate acid chloride derivative (that is: the quality of vitamin E succinate acid chloride derivative is respectively 2%, 5%, 10% of the sericin...

Embodiment 3

[0060] Example 3 Redox-sensitive sericin-vitamin E succinate micelles loaded with doxorubicin

[0061] Weigh 20 mg of Ser-SS-VES-3 prepared in Example 2 and dissolve in 2 mL of DMSO, fully dissolve, put into a dialysis bag with a molecular weight cut-off of 3500 Da, dialyze in 500 mL of pure water for 24 hours, change the water at 3 hours, 6 hours and 12 hours , filtered through a 450nm needle filter, dilute to 20mL, and store in a refrigerator at 4°C until detection. The preparation method of micelles encapsulating doxorubicin is slightly different. Weigh 20mg Ser-SS-VES-3 and dissolve it in 2mL DMSO. The amine was neutralized, put into a dialysis bag with a molecular weight cut-off of 3500Da and dialyzed, and the sericin derivative micelles wrapped with doxorubicin were obtained and recorded as Ser-SS-VES-3 / DOX.

[0062] Measure the concentration of doxorubicin in the release liquid by an ultraviolet spectrophotometer, and calculate the cumulative release rate of doxorubici...

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Abstract

The invention discloses an oxidoreduction sensitive sericin derivative with the anti-tumor activity and preparation and application thereof, and belongs to the technical field of biological medicine materials. The derivative is composed of hydrophilic sericin and hydrophobic vitamin E succinate which are connected through a disulfide bond; the mass ratio of the sericin to the vitamin E succinate is 20:1-100:1, and the content of the disulfide bond in every 100 amino acid units accounts for 10-25% on average. According to the oxidoreduction sensitive sericin derivative with the anti-tumor activity, under the environment of a water solution, self-assembling can be performed to form a nano-micelle with an internal hydrophobic cavity, a hydrophobic anti-cancer drug can be loaded, bonds can bebroken under the high reduction type glutathione content, and the drug can be rapidly released under the tumor microenvironment. The micelle system can effectively enhance the cancer cell killing effect of drugs, and the good research value and application prospect are achieved in the cancer treatment field.

Description

technical field [0001] The invention belongs to the technical field of biomedical materials, and in particular relates to a redox-sensitive sericin derivative with antitumor activity, a preparation method and application thereof. Background technique [0002] Sericin, a natural highly hydrophilic globulin derived from silk insects, was considered a waste product in the cocoon industry in the past. In recent years, sericin has been found to have many biological activities, such as cell adhesion, low immunogenicity and biodegradability in vivo, etc., and has received great attention in the field of biomedicine. Currently, sericin has been fabricated into various forms of biomaterials, including membranes, microspheres, hydrogels, electrospun fibers, and nanoparticles (Lallepak Lamboni. Biotechnology Advances, 2015, 33: 1855-1867). [0003] The sericin molecule itself has amphiphilic properties and self-assembles in aqueous solution. However, the size of the pure sericin assem...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K47/64A61K31/355A61K31/704A61K9/107A61P35/00
CPCA61K9/1075A61K31/355A61K31/704A61K47/64A61P35/00A61K2300/00
Inventor 张黎明邓立志
Owner SUN YAT SEN UNIV
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