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Cinnamyl aldehyde modified polyethylene glycol-polyamino acid block copolymer, preparation method thereof, and hydrogel

A technology of block copolymer and polyethylene glycol, which is applied in the field of polyamino acids, can solve the problems of restricting the application of temperature-sensitive injectable hydrogels, lack of drug properties or biological activity, etc., so as to improve drug delivery efficiency and prolong drug delivery. Drug time, the effect of improving solubility

Active Publication Date: 2020-12-04
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the hydrogels currently reported are only used as carriers of bioactive substances, and they do not have medicinal properties or biological activities. The loading of bioactive substances mainly depends on physical embedding, which limits temperature sensitivity to a certain extent Application of type injectable hydrogel

Method used

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  • Cinnamyl aldehyde modified polyethylene glycol-polyamino acid block copolymer, preparation method thereof, and hydrogel
  • Cinnamyl aldehyde modified polyethylene glycol-polyamino acid block copolymer, preparation method thereof, and hydrogel
  • Cinnamyl aldehyde modified polyethylene glycol-polyamino acid block copolymer, preparation method thereof, and hydrogel

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preparation example Construction

[0049] The present invention further provides a polyethylene glycol modification of the above cinnamaldehyde - preparation of polyamino acid block copolymer characterized by comprising the steps of:

[0050] The polyethylene glycol compound, γ- -N- ethyl -L- glutamate and the carboxylic anhydride ε- benzyloxycarbonyl -L- lysine -N- mixed acid anhydride within acid polymerization reaction to obtain a reaction product;

[0051] The reaction product was sequentially passes terminated acetyl, hydrobromic acid and the deprotection treatment cinnamaldehyde grafting reaction to give cinnamic aldehyde-modified polyethylene glycol - poly-amino acid block copolymer;

[0052] Amino-terminated polyethylene glycol monomethyl ether or polyethylene glycol structure of formula V as shown in the polyethylene glycol compound selected from a structure of the terminal amino group of Formula IV;

[0053]

[0054] Wherein, m is the degree of polymerization, 10≤m≤227

[0055] n is the degree of polyme...

Embodiment 1

[0098] Polyethylene glycol monomethyl ether in Example 1 (terminal amino group of: γ- -N- ethyl -L- glutamate anhydride within acid: ε- benzyloxycarbonyl -L- lysine -N- the carboxylic acid anhydride monomer = 1: 5: 2)

[0099] To a dry reaction bottle was added 2g, number average molecular weight of 550 amino end of polyethylene glycol monomethyl ether. And 100mL of dry toluene under azeotropic removal of water 130 ℃ 2h, drained residual toluene under reduced pressure; the resulting solid was dissolved in 50mL dried after addition of water, N, N- dimethyl formamide, to give a first solution ;

[0100] The said 3.7gγ- -N- ethyl -L- glutamate and the carboxylic anhydride group 2.22gε- benzyloxycarbonyl -L- lysine -N- acid anhydride was dissolved in 50mL the dewatering drying after the N, N- dimethylformamide to give a second solution;

[0101] Protection under a nitrogen atmosphere, mixing the first solution with the second solution and stirred for 24 hours at 45 deg.] C; After comp...

Embodiment 2

[0105] Polyethylene glycol monomethyl ether Example 2 (terminal amino group of: γ- -L- glutamate ethyl ester -N- acid anhydride: ε- benzyloxycarbonyl -L- lysine -N- the carboxylic acid anhydride monomer = 1: 8: 2)

[0106] To a dry reaction bottle was added 2g, number average molecular weight of 550 amino end of polyethylene glycol monomethyl ether. And 100mL of dry toluene under azeotropic removal of water 130 ℃ 2h, drained residual toluene under reduced pressure; the resulting solid was dissolved in 50mL dried after addition of water, N, N- dimethyl formamide, to give a first solution ;

[0107] The said 5.92gγ- -N- ethyl -L- glutamate and the carboxylic anhydride group 2.22gε- benzyloxycarbonyl -L- lysine -N- acid anhydride was dissolved in 50mL the dewatering drying after the N, N- dimethylformamide to give a second solution;

[0108] Protection under a nitrogen atmosphere, mixing the first solution with the second solution and stirred for 24 hours at 45 deg.] C; After complet...

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Abstract

The invention provides a cinnamyl aldehyde modified polyethylene glycol-polyamino acid block copolymer. The cinnamyl aldehyde modified polyethylene glycol-polyamino acid block copolymer comprises a first block with a structure as shown in a formula I or a formula II and a second block with a structure as shown in a formula III. On the basis of the traditional temperature-sensitive polyurethane hydrogel, the temperature-sensitive hydrogel formed by the block copolymer provided by the invention can be used for supporting an aldehyde micromolecular drug cinnamyl aldehyde from a natural source through a chemical bonding effect, regulating the bonding ratio of cinnamyl aldehyde, improving the solubility of cinnamyl aldehyde and prolonging the drug administration time through a sustained and controlled release effect, and the drug administration efficiency is increased. The drug-loaded temperature-sensitive hydrogel provided by the invention has temperature sensitivity and a drug loading effect at the same time, and can be singly used or combined with other drugs by utilizing the pharmacological action of cinnamyl aldehyde which is an aldehyde small molecular drug, so that the further application of the hydrogel is expanded.

Description

Technical field [0001] The present invention belongs to the technical field polyamino acids, in particular to a polyethylene glycol-modified cinnamaldehyde - polyamino acid block copolymer, its preparation and hydrogel. Background technique [0002] In recent years, a new type of hydrogel as slow release mode of administration, in addition to the dose slow release mode of administration common small, less frequency of administration than the toxic side effects, etc., also has a simple mode of preparation, for You can not find fault with drug-carrying properties, and therefore has been widely studied. [0003] Temperature-sensitive hydrogel is a variation may be generated in response to thermal stimulation of the hydrogel, when the temperature is lower than the phase transition temperature, the hydrogel solution state is present, once the temperature reaches or exceeds the phase transition temperature, by solution state phase transition occurs rapidly, forming a hydrogel comprisin...

Claims

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Application Information

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IPC IPC(8): C08G69/50C08G69/48C08G69/40C08L77/04C08J3/075A61K47/59A61K31/11A61K9/06A61P31/04A61P31/10A61P35/00
CPCA61K9/0019A61K9/06A61K31/11A61K47/59A61P31/04A61P31/10A61P35/00C08G69/40C08G69/48C08G69/50C08J3/075C08J2377/04
Inventor 贺超良陈志雄陈学思
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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