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Dual-response dipeptide supramolecular polymer, and preparation method and application thereof

A supramolecular polymer and dual response technology, which is applied to the preparation method of peptides, non-effective ingredients of polymer compounds, chemical instruments and methods, etc., can solve the problems of small synthesis dosage, long polypeptide chain and high synthesis cost, and achieve the goal of preparation Simple, Fluorescent Intensity Enhanced Effect

Active Publication Date: 2021-11-23
JINING MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the polypeptide chain is generally long during assembly, and the solid-phase synthesis method is usually used. This method has a small synthesis dose, a long separation and purification cycle, and high synthesis costs.

Method used

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  • Dual-response dipeptide supramolecular polymer, and preparation method and application thereof
  • Dual-response dipeptide supramolecular polymer, and preparation method and application thereof
  • Dual-response dipeptide supramolecular polymer, and preparation method and application thereof

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preparation example Construction

[0080] The present invention also provides a preparation method of the supramolecular monomer, comprising the following steps:

[0081] (1) Tryptophan, 1-hydroxybenzotriazole, glycine methyl ester hydrochloride, dichloromethane, N,N-diisopropylethylamine and 1-ethyl-(3-dimethylamino Propyl) carbodiimide hydrochloride mixed, carry out condensation reaction, obtain compound A;

[0082] (2) Mix compound A, hydrated lithium hydroxide and methanol aqueous solution, and carry out a substitution reaction to obtain compound B;

[0083] (3) Mix compound B, branched alkoxy ether, dichloromethane, 4-dimethylaminopyridine and 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride, and carry out Esterification reaction to obtain compound C;

[0084] (4) Compound C, dichloromethane and trifluoroacetic acid were mixed for a substitution reaction to obtain compound D;

[0085] (5) Under alkaline conditions, compound D, monomers and reactants are mixed for amidation reaction to obtain t...

Embodiment 1

[0153] In a nitrogen atmosphere, mix 1 mmol of Boc-L-tryptophan, 1.2 mmol of 1-hydroxybenzotriazole, 1.1 mmol of glycine methyl ester hydrochloride and 10 mL of dichloromethane, and then add 2 mmol of N, N-diisopropylethylamine was initially reacted at 0°C and 350rpm for 20 minutes to obtain a reaction system, and the reaction system was mixed with 1.2 mmol of 1-ethyl-(3-dimethylaminopropyl)carbodiimide salt acid salt mixture, nitrogen replacement, secondary reaction at 0°C, 350rpm for 20min; after the secondary reaction, condensation reaction at 25°C for 11h; TLC detection after the reaction, the volume ratio of petroleum ether and ethyl acetate is 2 : 3, then use 10% potassium bisulfate solution to extract, the volume ratio of reaction solution and potassium bisulfate solution is 1:1.5; then use dichloromethane to extract 3 times, the volume ratio of reaction solution and dichloromethane is 1 : 1.3; the combined total volume of the extracted organic phases is 13mL, and dried...

Embodiment 2

[0164] In a nitrogen atmosphere, mix 1.2 mmol of Boc-L-tryptophan, 1 mmol of 1-hydroxybenzotriazole, 1.3 mmol of glycine methyl ester hydrochloride and 4 mL of dichloromethane, and then add 2.6 mmol of N ,N-diisopropylethylamine was initially reacted at 0°C and 400rpm for 25min to obtain a reaction system, and the reaction system was mixed with 1.44mmol of 1-ethyl-(3-dimethylaminopropyl)carbodiimide Mix hydrochloride, replace nitrogen, and perform a secondary reaction at 0°C and 400rpm for 25 minutes; after the secondary reaction, condense at 30°C for 12 hours; after the reaction, perform TLC detection, the volume ratio of petroleum ether and ethyl acetate is 2.5:3.5, then adopt 10% potassium hydrogensulfate solution to extract, the volume ratio of reaction solution and potassium hydrogensulfate solution is 1:1.3; Then use dichloromethane to extract 3 times, the volume ratio of reaction solution and dichloromethane is 1:1.4; Combine the extracted organic phases and dry them wi...

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Abstract

The invention belongs to the technical field of high-molecular compounds. The invention provides a dual-response dipeptide supramolecular polymer, which is a dual-sensitive supramolecular polymer prepared by the following steps of: modifying a hypoxic response element p-nitrochloroformic acid benzyl ester or 2-(2-nitroimidazole-1-yl) acetic acid at an N terminal and modifying a temperature-sensitive element dendritic alkoxy ether at a C terminal through tryptophan glycine dipeptide by adopting a liquid phase synthesis method, and performing self-assembly in an aqueous solution. The supramolecular polymer is simple to prepare; the fluorescence intensity is greatly enhanced under the hypoxic condition through the fluorescence characteristic of tryptophan; meanwhile, the polymer can coat the medicine; the polymer is disassembled under the hypoxic condition to realize the release of the medicine; and a research basis is provided for the research and development of a novel nano-medicine carrier.

Description

technical field [0001] The invention relates to the technical field of polymer compounds, in particular to a dual-response dipeptide supramolecular polymer and its preparation method and application. Background technique [0002] Hypoxia is one of the prominent features of solid tumors. Excessive growth and proliferation of tumor cells lead to inability to meet the oxygen demand or decrease the ability to transmit oxygen to other parts, thus causing a hypoxic environment inside the cells. Hypoxic environment is closely related to tumor growth, metastasis and drug resistance. And because of its special physiological and chemical response to the outside world, combined with the advantages of peptide biocompatibility, biodegradability, and easy regulation through external stimuli, hypoxia-responsive groups (such as nitroimidazole, azo Benzene, 4-nitrobenzyl ester) to prepare hypoxia-responsive self-assembled polypeptides for targeted tumor therapy and diagnosis has attracted m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K5/078C07K1/107C07K1/02C09K11/06A61K47/42A61K31/192A61K49/00A61P35/00B82Y5/00
CPCC07K5/06156C09K11/06A61K47/42A61K31/192A61P35/00A61K49/0045B82Y5/00C09K2211/1466
Inventor 王军杨中兴刘景王守信孔令栋李正澳耿晓晴宋豪杰
Owner JINING MEDICAL UNIV
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