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Linker of amino-modified cyclodextrin bonded to open-ring cucurbituril and its preparation method and application

A technology of cucurbituril and cyclodextrin, which is applied in the field of linkages of amine-modified cyclodextrins bonded to open-ring cucurbituril and its preparation, which can solve the problem of high drug size and cavity matching, drug water Poor solubility, lower bioavailability and other problems, to achieve the effect of improving water solubility and bioavailability, increasing solubility, and increasing water solubility

Active Publication Date: 2020-08-25
KUNMING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, the existing supramolecular drug carriers such as cyclodextrin and its derivatives have high requirements on the matching degree of the size of the drug and the cavity. The drug is poorly soluble in water, so when it is administered alone, the drug will be affected by its own poor water solubility, which will reduce its bioavailability

Method used

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  • Linker of amino-modified cyclodextrin bonded to open-ring cucurbituril and its preparation method and application
  • Linker of amino-modified cyclodextrin bonded to open-ring cucurbituril and its preparation method and application
  • Linker of amino-modified cyclodextrin bonded to open-ring cucurbituril and its preparation method and application

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Experimental program
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Effect test

Embodiment 1

[0040] Embodiment 1: Synthetic preparation of tetramer and sulfonic acid sodium salt benzene ring side arm and

[0041] Carry out with reference to the method in literature Ma D, et al.Nature Chemistry, 2012,4(6):503:

[0042] (1) Synthesis of dimer: mix glycoluril (500g, 3.51mol) and paraformaldehyde (105g, 3.51mol) evenly, add to HCl solution (8M, 700mL), and heat the reaction solution at 50°C for 48h; After the reaction, the reaction solution was cooled and vacuum filtered to obtain the 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 (334 g, 62%) ;

[0043]

[0044] (2) Synthesis of tetramer: dimer (304g, 1.20mol) was added to anhydrous MeSO 3 In H (600mL), after the dimer is completely dissolved, the solution becomes transparent, then etherified methyl glycoluril (84g, 0.27mol) is added; the reaction solution is reacted at 50°C for 3h; The solution was poured into water (6.0L...

Embodiment 2

[0048] Embodiment 2: the synthesis of carboxyl-containing benzene ring side arm

[0049] 3g (0.024mol) of p-methoxyphenol and 3mL of methyl bromopropionate, add some N,N-dimethylformamide to help dissolve, stir well and add 4g (0.029mol) of K 2 CO 3 , reacted for 20-24 hours to generate p-methoxyphenylpropionyl methyl ester; after that, add 3g (0.125mol) LiOH, 10mL H 2 O and 10 mL of tetrahydrofuran were used to hydrolyze the ester; the reaction finally produced 4.5 g of carboxyl-containing side arms, with a yield of 89.3%.

[0050]

Embodiment 3

[0051] Embodiment 3: the synthesis of ring-opening cucurbituril containing carboxylic acid group

[0052] Fully dissolve 1.8g (2.45mmol) of tetramer in 8mL of acetic anhydride and 8mL of trifluoroacetic acid, and mix thoroughly in an oil bath at 60°C to 80°C to completely dissolve the tetramer. After 5 to 10 minutes, Then add the benzene ring side arm of sodium sulfonate and the carboxyl-containing benzene ring side arm to continue the reaction for 3 to 4 hours; after the reaction, drop the reaction solution into a rapidly stirring organic solvent, such as acetone, methanol, etc. Extract it. Since there may be three different open-ring cucurbiturils in the generated product, extract and separate them according to their degree of hydrolysis; first, drop the reaction solution into rapidly stirring acetone, and after adding it completely, continue stirring for 0.5~ 1h, after suction filtration, put it into a vacuum drying oven for drying; dissolve the product with a certain amou...

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Abstract

The invention discloses a bonding agent of amino-modified cyclodextrin and open loop cucurbituril with structural formula shown in the following formula: (the formula is shown in the description) wherein m is 0 to 7, n is 1 to 8 and m+n=6, 7 or 8, k is an integer of 0-4; the method uses carboxyl group-containing open loop cucurbituril as raw material to be condensed with amino-modified cyclodextrin to obtain a dual drug-carrying medicinal supramolecular material with a closed cavity and an open cavity; the dual drug-carrying medicinal supramolecular carrier is of higher drug-carrying efficiency, the preparation method has higher productivity, simple reaction and mild reaction conditions, and can be used as candidate carriers for drugs.

Description

technical field [0001] The invention relates to the technical field of pharmacy, in particular to a bonded amino-modified cyclodextrin bonded ring-opened cucurbituril and its preparation method and application. Background technique [0002] At present, the research field of supramolecular drug carriers has expanded from closed cavities (such as cyclodextrin, cucurbit[n]uril) to open semi-annular cavities. The structure of open-loop cucurbituril breaks the closed-cavity drug-loading mode of closed-loop cucurbituril and cyclodextrin series. Open-loop cucurbituril has its own natural structural advantages, that is, the side arms of the open-loop can be modified according to structural requirements to achieve The purpose of better drug loading is to expand the binding constant; and the open-loop cucurbituril is a semi-circular structure molecule, and the rigidity of the ring molecular structure is less than that of the closed-loop cucurbituril. The open-ring cucurbituril is tha...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08B37/16A61K47/69
CPCA61K47/6951C08B37/0012
Inventor 杨波梁婧秦琪赵榆林
Owner KUNMING UNIV OF SCI & TECH
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