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D-galactose-bonded open-ringed cucurbituril and application thereof

A technology of cucurbituril and galactose, which is applied in the field of supramolecular drug carriers, can solve the problems of not being able to achieve targeted transportation, not having molecular targeting, and not being able to identify and assemble, and achieve the effects of improving solubility and water solubility.

Active Publication Date: 2018-05-08
KUNMING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] However, both cucurbituril and cyclodextrin are closed cavities with high rigidity, and they cannot be identified and assembled when the molecular size is not suitable; therefore, Lyle et al., based on the cucurbituril, carried out the closed-loop cucurbituril cavity. Structural modification; based on the tetramer, modify the side arm based on the benzene ring, and then improve the water solubility and the ability to recognize molecules. At present, there are no related reports on D-galactose modified open-ring cucurbituril
[0004] Most of the existing ring-opening cucurbiturils only simply modify and replace the benzene ring. If only ionization is carried out, the ionization does not have molecular targeting, and the application in anti-cancer can not achieve the role of targeted transport.

Method used

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  • D-galactose-bonded open-ringed cucurbituril and application thereof
  • D-galactose-bonded open-ringed cucurbituril and application thereof
  • D-galactose-bonded open-ringed cucurbituril and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Embodiment 1: the synthetic preparation of tetramer

[0028] With reference to the method in the literature Ma D, et al. Nature Chemistry, 2012, 4(6):503:

[0029] (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%);

[0030] ;

[0031] (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

[0033] Embodiment 2: the synthesis of bromobenzene ring side arm

[0034] Referring to the method in the literature Zhang M, Sigwalt D, Isaacs L. [J]. Chemical Communications, 2015,51(78):14620-3, add hydroquinone bis(2-hydroxyethyl) ether in acetonitrile (5 mL) (1.98 g, 0.01 mol), add carbon tetrabromide (13.24 g, 0.04 mol) and triphenylphosphine (5.24 g, 0.02 mol) after hydroquinone bis(2-hydroxyethyl) ether is completely dissolved, and the reaction solution React at room temperature for 4 h. After the reaction, pure water (200 mL) was added to the reaction solution to produce a white precipitate, which was vacuum filtered to obtain a crude product; the crude product was washed 3 times with methanol / water (volume ratio 3:2), each 100 mL each time, the pure product was obtained. Dry in a vacuum drying oven to obtain a white solid, and finally obtain the side arm of the brominated benzene ring;

[0035] .

Embodiment 3

[0036] Embodiment 3: the synthesis of brominated open-ring cucurbituril

[0037] Weigh 1.8 g (2.45 mmol) of the tetramer, add 8 mL of acetic anhydride and 8 mL of trifluoroacetic acid to the tetramer, and mix thoroughly in an oil bath at 70°C until the tetramer is completely dissolved, then Add 1.6 g (4.9 mmol) of the side arm of the bromobenzene ring and continue the reaction for 3 h;

[0038] .

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Abstract

The invention belongs to the field of supermolecular drug carriers and discloses D-galactose-bonded open-ringed cucurbituril with a structural formula shown in the specification, wherein R is a groupshown in the specification or a halogen, and at least one R is the group shown in the specification. The open-ringed cucurbituril containing a D-galactose group is a macrocyclic cryptand with an innercavity, and the open-ringed structure makes the ring rigidity of the macrocycle of the D-galactose-bonded open-ringed cucurbituril reduced and the D-galactose-bonded open-ringed cucurbituril has extremely strong host-guest bonding capacity; and the galactose-containing open-ringed cucurbituril disclosed by the invention has good water solubility, can be used as a drug carrier to be widely appliedto drug transportation, can also be used for greatly improving the bioavailability and stability of a drug and has potential tumor cell targeting property.

Description

technical field [0001] The invention belongs to the field of supramolecular drug carriers, in particular to a D-galactose-linked split-ring cucurbituril and a preparation method thereof. Background technique [0002] In 1905, Behrend et al. reported a new type of macrocyclic compound obtained from the reaction of glycoluril and formaldehyde. By 1976, Freeman et al. determined the structure of the macrocyclic compound. Because of its similar shape to cucurbit, it is generally called cucurbit [n] urea ( CB[n]). Like cyclodextrin, cucurbituril (CB) is a supramolecular drug carrier with a closed cavity. At present, cucurbituril has been used in drug delivery, catalysts, molecular machines, sensors, ion channels, wastewater treatment, etc. field. [0003] However, both cucurbituril and cyclodextrin are closed cavities with high rigidity, and they cannot be identified and assembled when the molecular size is not suitable; therefore, Lyle et al., based on the cucurbituril, carrie...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H3/02A61K47/26A61K47/69A61K31/56
CPCA61K47/26A61K31/56C07H3/02
Inventor 杨波梁婧赵榆林吕品张东京
Owner KUNMING UNIV OF SCI & TECH
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