Amphiphilic tree-like calixarene used as solubilizer or dispersing agent

A dendritic, amphiphilic technology, applied in the field of chemistry, can solve problems such as limitations and achieve the effect of increasing firmness

Inactive Publication Date: 2010-12-22
HUAZHONG UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These two amphiphilic dendritic calixarenes have better solubilizing and dispersing effects than general amphiphilic calixarenes, but the former is alkaline, and the latter is acidic, and generally needs to be adjusted to It can only be used after neutralization, especially when it is used as a carrier of acid or alkali sensitive substances such as drugs.

Method used

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  • Amphiphilic tree-like calixarene used as solubilizer or dispersing agent
  • Amphiphilic tree-like calixarene used as solubilizer or dispersing agent
  • Amphiphilic tree-like calixarene used as solubilizer or dispersing agent

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Calixarene compound Ia (in general formula I, x=y=z=3, R 1 = R 2 = R 3 =OCH 3 , m=4, n=8) synthesis:

[0044] Compound II a (in general formula II, x=y=z=3, R 1 = R 2 = R 3 =OCH 3 ) (1.0g, 1.6mmol) was dissolved in dichloromethane (15mL), and IIIa (in general formula III, m=4, n=8) (300mg, 0.28mmol) and triethylamine (0.3ml , 2.2mmol), reflux 3h, silica gel column chromatography (eluent CHCl 3 :CH 3 OH 60:1), finally a colorless viscous solid (450 mg) was obtained with a yield of 48.7%. Calixarene compound Ia can be dissolved in common solvents, both can be dissolved in very polar water, in polar alcohols, esters, ketones, nitriles, ethers, halogenated hydrocarbons, aromatic hydrocarbons, DMF, It can be dissolved in polar solvents such as DMSO, and can also be dissolved in non-polar solvents such as n-hexane, petroleum ether and other alkanes.

[0045] Calixarene Ia 1 H-NMR spectrum and 13 C-NMR spectra are shown in figure 1 and figure 2 . Its matrix-as...

Embodiment 2

[0047] The aqueous solution of calixarene compound Ia is using λ ex = When excited by light with a wavelength of 280nm, it will emit fluorescence, and the maximum emission wavelength is λ em = 450 nm (both excitation and emission slit width 5 nm). The fluorescence intensity of the maximum emission peak varies with the concentration as Figure 4 shown, at concentrations less than 1.0 x 10 -5 In the range of M, the fluorescence intensity increases with the increase of concentration; when the concentration is greater than 1.0×10 -5 In the range of M, the fluorescence intensity decreases with the increase of the concentration. Therefore, calixarene compound Ia will form micelles in aqueous solution, and its critical micelle concentration CMC=1.0×10 -5 M, that is, less than this concentration, Ia will not form micelles in aqueous solution, and greater than this concentration, Ia will form micelles in aqueous solution.

[0048] Calixarene compound Ia at 5.0×10 -4 The transmiss...

Embodiment 3

[0050] Solubilization test of naproxen, an anti-inflammatory, analgesic and fever-reducing drug. Dissolve 18 mg Ia in 0.5 mL deionized water to give 1.0 × 10 -2 M aqueous solution. Then 1.1 mg of naproxen was added and stirred at room temperature for 1 h to obtain a clear and transparent aqueous solution. If there is no Ia, the solubility of naproxen in pure 0.5mL deionized water is only 0.02mg, and the addition of Ia increases the solubility of naproxen in water by more than 50 times. The transmission electron micrograph of the Ia aqueous solution after adding naproxen is as Image 6 As shown, the diameter of the smallest nanomicelle is about 10nm, which is nearly double that of the micelle with a diameter of about 6nm without adding naproxen, and the center of the micelle has an obvious cavity with a size of about 4nm. The bundle shells are around 3nm thick, suggesting that these smallest particles are indeed micelles. The shape and size of the above-mentioned micelles a...

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Abstract

The invention provides amphiphilic tree-like calixarene used as solubilizer or dispersing agent; a tree-like polyoxyethylene ether chain is connected with the upper end of the calixarene; an alkyl chain is connected with the lower end of the calixarene; and the calixarene can be dissolved in a nonpolar organic solvent and water. The amphiphilic tree-like calixarene can lead naproxen and ibuprofenwhich are difficult to dissolve in water, diminish inflammation, relieve pain and reduce the fever to be easy to dissolve in water, can lead anti-cancer drug camptothecin to effectively disperse in water to become a stable suspension.

Description

technical field [0001] The invention belongs to the field of chemistry and relates to calixarene. Background technique [0002] Calixarene is a macrocyclic compound composed of multiple phenols linked by methylene groups. The lipophilic cavity in the ring can contain organic compounds. It is used in the loading, storage, transportation, slow release, separation and extraction of chemical substances. It has important uses and is known as the third-generation main compound after cyclodextrin and crown ether. It has attracted great attention from chemists, material scientists and pharmacists at home and abroad. Some substances, such as drugs, pigments, dyes, paints, etc., are poorly soluble or insoluble in water, and need to be dissolved or dispersed in water with the help of dispersants or solubilizers. Dendritic amphiphilic calixarene is water-soluble, and can coat other substances in calixarene to make it dissolve or stably disperse in water. It is a widely used in the fiel...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C235/56C07C231/02B01F17/42A61K47/16C09K23/42
Inventor 郑炎松黄宏
Owner HUAZHONG UNIV OF SCI & TECH
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