CUCURBITURIL-CONTAINING GEL AND METHOD OF PREPARING THE SAME

Abstract

Provided are a gel including a compound represented by Formula 1 below and a method of preparing the same:

Description

BRIEF DESCRIPTION OF THE DRAWINGS

The above and other features and advantages of the present invention will become more apparent by describing in detail exemplary embodiments thereof with reference to the attached drawings in which:

FIG. 1 is an Atomic Force Microscopic (AFM) image of the gel phase of a composition prepared by dissolving cucurbit[7]uril in an aqueous sulfuric acid solution and a schematic diagram illustrating a gel-forming process;

FIG. 2 is images of the sol and gel phases of a composition prepared by dissolving cucurbit[7]uril in distilled water;

FIG. 3 is an AFM image of the gel phase of a composition prepared by dissolving cucurbit[7]uril in distilled water;

FIG. 4 is an AFM image of the gel phase of a composition prepared by dissolving cucurbit[7]uril in distilled water followed by addition of a concentrated sulfuric acid;

FIG. 5 is a graph illustrating an absorbance with respect to a temperature for a composition prepared by dissolving cucurbit[7]uril in a sulfuric acid solution;

FIG. 6 is an image of the gel phase of a composition prepared by dissolving cucurbit[7]uril in a sulfuric acid solution followed by addition of oxaliplatin;

FIG. 7 is images of the sol and gel phases of a composition prepared by dissolving cucurbit[7]uril in a sulfuric acid solution followed by addition of trans-diaminostilbene;

FIG. 8 is a cyclic voltammogram showing a sol-gel phase transition in response to a electrochemical stimulus for a composition prepared by dissolving cucurbit[7]uril in a sulfuric acid solution followed by addition of benzoquinone; and

FIG. 9 is images of the sol and gel phases of a composition prepared by dissolving cucurbit[7]uril in a sulfuric acid solution followed by addition of benzoquinone.

Claims

1. A gel comprising a compound represented by Formula 1 below:

2. The gel of claim 1, wherein A1 or A2 is an allyloxy group.

3. The gel of claim 1, wherein n is 7, X is O, and A1 and A2 are each H.

4. The gel of claim 1, wherein the content of the compound of Formula 1 is 1 to 10 wt %.

5. The gel of claim 1, further comprising an acid.

6. The gel of claim 5, wherein the acid is selected from the group consisting of sulfuric acid, hydrochloric acid, nitric acid, phosphoric acid, chloric acid, HBF4, HPF6, acetic acid, trifluoroacetic acid, oxalic acid, benzoic acid, ascorbic acid, and HAuCl4.

7. The gel of claim 1, further comprising a base.

8. The gel of claim 7, wherein the base is selected from the group consisting of sodium hydroxide, potassium hydroxide, calcium hydroxide, methylamine, ethylamine, pyridine, and aniline.

9. The gel of claim 1, further comprising a pharmacologically active substance.

10. The gel of claim 9, wherein the pharmacologically active substance is an organic compound selected from the group consisting of hydrocortisone, prednisolone, spironolatone, testosterone, megestrol acetate, danasol, progesterone, indometasine, amphotericin B, and a combination thereof.

11. The gel of claim 9, wherein the pharmacologically active substance is a protein selected from the group consisting of human growth hormone, G-CSF (granulocyte colony-stimulating factor), GM-CSF (granulocyte-macrophage colony-stimulating factor), erythropoietin, vaccine, antibody, insulin, glucagon, calcitonin, ACTH (adrenocorticotropic hormone), somatostatin, somatotropin, somatomedin, parathormone, thyroxine, a substance secreted from hypothalamus, prolactin, endorphin, VEGF (vascular endothelial growth factor), enkephalin, vasopressin, nerve growth factor, non-naturally occurring opioid, interferon, asparaginase, alginase, superoxide dismutase, trypsin, chymotrypsin, pepsin, and a combination thereof.

12. The gel of claim 1, further comprising a stimulus-responsive compound.

13. The gel of claim 12, wherein the stimulus-responsive compound is a light-responsive compound.

14. The gel of claim 13, wherein the stimulus-responsive compound comprises an azobenzene group or a stilbene group.

15. The gel of claim 12, wherein the stimulus-responsive compound is a compound undergoing a change in structure or oxidation state in response to an electrochemical stimulus.

16. The gel of claim 15, wherein the stimulus-responsive compound is quinone, benzoquinone, naphthoquinone, anthraquinone, hydroquinone, catechol, viologen, or a compound comprising one of these.

17. The gel of claim 12, wherein the stimulus-responsive compound is a pH-responsive compound.

18. A method of preparing a gel, the method comprising: (i) dissolving a compound represented by Formula 1 below in a solvent to prepare a sol;(ii) adding a pharmacologically active substance to the sol of (i); and(iii) converting the resultant pharmacologically active substance-containing sol of (ii) to a gel:

19. A method of preparing a gel, the method comprising: (i) mixing a compound represented by Formula 1 below with a pharmacologically active substance;(ii) adding a solvent to the resultant mixture of (i) to prepare a sol; and(iii) converting the sol of (ii) to a gel:

20. A method of preparing a gel, the method comprising: (i) dissolving a compound represented by Formula 1 below in a solvent to prepare a sol;(ii) adding a stimulus-responsive compound to the sol of (i); and(iii) converting the resultant stimulus-responsive compound-containing sol of (ii) to a gel:

21. The method of claim 20, wherein in (i) or (ii), a pharmacologically active substance is further added.

22. A method of preparing a gel, the method comprising: (i) mixing a compound represented by Formula 1 below with a stimulus-responsive compound;(ii) adding a solvent to the resultant mixture of (i) to prepare a sol; and(iii) converting the sol of (ii) to a gel:

23. The method of claim 22, wherein in (i) or (ii), a pharmacologically active substance is further added.