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Alkali-sensitive ring opening cucurbituril and application thereof

A cucurbituril, sensitive technology, applied in the field of supramolecular drug carriers, to achieve the effect of increasing water solubility, strengthening host-guest bonding ability, and avoiding irritation

Active Publication Date: 2018-05-29
KUNMING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, it is challenging to design molecular containers that can achieve controlled release of guest molecules under external alkaline stimuli while maintaining high affinity under neutral conditions.

Method used

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  • Alkali-sensitive ring opening cucurbituril and application thereof
  • Alkali-sensitive ring opening cucurbituril and application thereof
  • Alkali-sensitive ring opening cucurbituril and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment 1: the synthetic preparation of tetramer

[0024] With reference to the method in the literature Ma D, et al. Nature Chemistry, 2012, 4(6):503:

[0025] (1) Synthesis of dimer: Mix glycoluril (500 g, 3.51 mol) and paraformaldehyde (105 g, 3.51 mol) evenly and add it to HCl solution (8 M, 700 mL). Heated for 48 hours; after the reaction was completed, the reaction solution was cooled and vacuum filtered to obtain a crude product; the crude product was washed with water (500 mL), and then recrystallized with TFA (1.5 L) to obtain a dimer as a white solid ( 334g, 62%);

[0026] ;

[0027] (2) Synthesis of tetramer: Dimer (304 g, 1.20 mol) was added to anhydrous MeSO 3 H (600 mL), after the dimer was completely dissolved and the solution became transparent, then etherified methyl glycoluril (84 g, 0.27 mol) was added; the reaction solution was reacted at 50°C for 3 hours; the reaction was completed Finally, the reaction solution was poured into water (6.0 L...

Embodiment 2

[0031] Embodiment 2: the synthesis of the side arm of benzene ring containing carboxylic acid group

[0032] Add N,N-dimethylformamide (approximately 10 mL) to 3 g (0.024 mol) of p-methoxyphenol, and add 3 mL of methyl bromopropionate after the p-methoxyphenol is completely dissolved. After fully stirring, add 4 g (0.029 mol) K 2 CO 3 , and reacted at room temperature for 20 h to generate p-methoxyphenylpropionyl methyl ester; the reaction solution was poured into methanol for recrystallization; the crude product was obtained after vacuum filtration; the crude product was washed three times with methanol (100 mL), and after suction filtration Dry with a vacuum oven to obtain p-methoxyphenylpropionyl methyl ester.

[0033] Take 3.2 g p-methoxyphenylpropionyl methyl ester, with 10 mL H 2 O and 10 mL tetrahydrofuran were used to dissolve the ester, and 3 g (0.125 mol) LiOH was slowly added to hydrolyze p-methoxyphenylpropionyl methyl ester; after the reaction, the reaction sol...

Embodiment 3

[0035] Example 3: Synthesis of Alkali Sensitive Open-ring Cucurbituril

[0036] Fully dissolve 1.8 g (2.45 mmol) of tetramer in 8 mL of acetic anhydride and 8 mL of trifluoroacetic acid, and mix thoroughly in an oil bath at 60°C. After the tetramer is completely dissolved, add two different The side arm of the benzene ring continued to react for 3 h; the molar ratio of the tetramer, the side arm of the benzene ring containing sulfonic acid groups, and the side arm of the benzene ring containing carboxylic acid groups was 1:1:1;

[0037] .

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Abstract

The invention discloses alkali-sensitive ring opening cucurbituril. A structural formula of the alkali-sensitive ring opening cucurbituril is shown. The alkali-sensitive ring opening cucurbituril hasthe advantages that the alkali-sensitive ring opening cucurbituril can be used as a supermolecular medicine carrier and is provided with large ring cryptand with inner cavities, the ring rigidity of large rings can be reduced by means of ring opening, and accordingly the alkali-sensitive ring opening cucurbituril is extremely high in host-guest bonding capacity; the alkali-sensitive ring opening cucurbituril is excellent in alkali sensitivity, contains carboxylic acid groups and can be used as the medicine carrier to be widely applied to medicine delivery paths, and the water solubility and the stability of insoluble medicines can be greatly improved; the alkali-sensitive ring opening cucurbituril can be used as an alkali-sensitive carrier, medicines can be released in alkaline environments such as small intestines in human bodies, accordingly, effects of releasing the medicines in a sustained and controlled manner can be realized, and irritation of the medicines on gastric mucosas canbe prevented.

Description

technical field [0001] The invention belongs to the field of supramolecular drug carriers, in particular to an alkali-sensitive split-ring cucurbituril and its application. Background technique [0002] Supramolecular chemistry has developed into an important field in the frontiers of chemistry. Crown ethers, cyclodextrins, and calixarenes are recognized as the first three generations of main compounds in the development of supramolecular chemistry. Cyclodextrins are good scaffolds for building aggregates and complex superstructures. Cucurbituril, which was developed later, has been widely used in everything because it can be firmly combined with a variety of drugs of appropriate size. [0003] Cucurbituril, similar to cyclodextrin, has a closed cavernous cavity, which can self-assemble with drugs. But the fly in the ointment is that due to the high rigidity of the ring closing the cavity, when it is matched with the drug, the deformation is small. As long as the size of t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22A61K31/357A61P33/06A61K47/22A61K47/34
CPCA61K47/22A61K47/34A61K31/357C07D487/22
Inventor 杨波梁婧赵榆林秦琪张东京
Owner KUNMING UNIV OF SCI & TECH
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