Polymer with high-efficient drug loading performance, and preparation method and application thereof

A technology for polymers and active drugs, which is applied in the field of polymers with high-efficiency drug-carrying properties and their preparation, can solve the problems of reducing rapid intermolecular aggregation of drugs, complex synthesis steps, difficult clinical applications, and the like, and achieves excellent drug-carrying properties, Simple to prepare and easy to promote

Active Publication Date: 2018-05-11
SUZHOU UNIV
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  • Abstract
  • Description
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  • Application Information

AI Technical Summary

Benefits of technology

This patented new type of polymers made from certain chemical compounds called benzobis boronate have been developed during this time due to their ability to attach themselves to other substances like medicines or proteins through strong interactions between them. These special types of polymer structures are useful because they help keep these things stable when loaded onto various carriers. They also improve the efficiency of delivering medicine towards target tissues while reducing clumpings caused by tiny particles found inside cells. Overall, this technology allows scientists to create better ways to administer pharmaceuticals effectively without causing damage to healthy ones' organs.

Problems solved by technology

The technical problem addressed in this patents relates to finding ways to increase the amount of medicine loaded into tiny particles when they enter cells without causing harmful side effects during their entry process. This would make delivering effective treatments more accessible while reducing patient's risk of treatment failure due to poorly understood factors like enzyme activity within cell membranes.

Method used

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  • Polymer with high-efficient drug loading performance, and preparation method and application thereof
  • Polymer with high-efficient drug loading performance, and preparation method and application thereof
  • Polymer with high-efficient drug loading performance, and preparation method and application thereof

Examples

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preparation example Construction

[0068] The polymer preparation method of formula (I) of the present invention follows the steps below:

[0069] In anhydrous N,N-dimethylformamide and dichloromethane mixed solvent (v:v is 1:9), using the primary amino group in polyethylene glycol with formula (II) and formula (III) Initiate the polymerization of γ-benzyl-L-aspartic acid ester-N-internal carboxylic acid anhydride. After the reaction is completed, an excessive amount of acetic anhydride can be added to end-block to obtain a polymer with a protective group, and then in N,N- Dimethylformamide neutralizes ethanolamine and reacts to obtain a copolymer with the structure of formula (IV).

[0070] In the process of preparing polymers with protective groups, the compound with the structure of formula (II) or formula (III) and the γ-benzyl-L-aspartic acid ester-N-internal carboxylic acid anhydride mono The molar ratio of the body is preferably 1:5~200, more preferably 1:10~50; the temperature of the reaction is prefer...

Embodiment 1

[0094] Add 5.00 g of polyethylene glycol monomethyl ether with a number average molecular weight of 5000 and a structure of formula (II) into the dry reaction flask, and remove water by azeotroping with 80 mL of anhydrous toluene at 130°C for 3 hours, then vacuum dry The remaining toluene; the obtained solid was dissolved in 20 mL of dry dichloromethane to obtain the first solution; 5.50 g of γ-benzyl-L-aspartate-N-endocarboxylic anhydride was dissolved in 5 mL of dry In a mixed solvent of N,N-dimethylformamide and 50 mL of dichloromethane, the second solution was obtained; in a nitrogen atmosphere, the first solution and the second solution were mixed, and stirred and reacted at room temperature under nitrogen protection conditions for 48 hours; Then 10 mL of acetic anhydride was added to continue the reaction for 24 h. After the reaction is over, remove most of the solvent under reduced pressure, then settle with ether, filter with suction, and dry to obtain a block copolyme...

Embodiment 2

[0100] In a dry round bottom flask, add 7.2g of 4-hydroxymethylphenylboronic acid pinacol ester and 10.3g of carbonyldiimidazole, add 50mL of anhydrous dichloromethane to dissolve, and react at room temperature for 12h. After the reaction was completed, 500 mL of ethyl acetate was added to the system for dilution, and the organic layer was washed with distilled water and saturated brine successively, and then the organic layer was washed with anhydrous MgSO 4 Let dry overnight. The organic solvent was removed under reduced pressure to finally obtain 7.6 g of the small molecule of formula (V). NMR analysis was carried out to the obtained block copolymer, image 3 For the small molecule prepared in Example 2, use deuterated dimethyl sulfoxide as a solvent, and the results show that the small molecule was successfully synthesized, and its specific structure is as follows:

[0101]

[0102] Formula (V).

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Abstract

The invention provides a polymer with a high-efficient drug loading performance, and a preparation method and application thereof. The polymer adopts poly(ethylene glycol)-b-poly [(N-2-hydroxyethyl)-asparaginate] as a basis, and is obtained through modification of phenylboronic acid. The polymer is prepared from main materials: polyethylene glycol and polyamino acid with favorable biocompatibility; a phenylboronic acid group of a polyamino acid side chain and a drug containing an amino group can achieve high-efficient drug loading through coordination interaction, the polymer has an ultrahighdrug loading rate (larger than 50 percent) and approximate 100 percent of encapsulation efficiency on clinically common chemotherapy drugs such as adriamycin, pharmorubicin and irinotecan, and the release of drug loading micelles has responsiveness of hydrogen peroxide; freeze-dried powder of the drug loading micelles has favorable redissolvability in a water solution, and a formed particle is small in particle size and narrow in distribution; meanwhile, the polymer is simple to prepare and convenient to popularize, and has a great development prospect in a biomedical material field, especially a drug delivery field.

Description

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Claims

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Application Information

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Owner SUZHOU UNIV
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