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Cystine cholesterol gelator and preparation method thereof

A cystine cholesterol and gel factor technology, applied in chemical instruments and methods, instruments, analytical materials, etc., can solve the problems of the rational design of the gel factor structure, the difficulty of precise control of the morphology and performance, and achieve enhanced non-complexity. Valence bond force, good gel properties, good biocompatibility

Active Publication Date: 2021-09-17
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, many building blocks have been used for the construction of low molecular weight gels, but the rational design of the structure of the gelling factor and the precise regulation of the morphology and properties are still relatively big problems.

Method used

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  • Cystine cholesterol gelator and preparation method thereof
  • Cystine cholesterol gelator and preparation method thereof
  • Cystine cholesterol gelator and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040]Example 1: Synthesis of a cystine-cholesterol gelling factor with a "butterfly" molecular structure, the synthesis route of the cystine-cholesterol gelling factor is as follows:

[0041]

[0042] (1) Synthesis of N-1-naphthylethylenediamine (Formula 1): Dissolve N-1-naphthylethylenediamine hydrochloride (600mg, 2.31mmol) in water, add NaOH solid (185mg, 4.62mmol ), stirred at room temperature for 2h. The aqueous phase was extracted three times with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, filtered, and rotary evaporated to obtain N-1-naphthylethylenediamine yellow oily liquid.

[0043] (2) Synthesis of tert-butoxycarbonyl (Boc)-protected cystine (Formula 2): Dissolve cystine (500mg, 2.08mmol) in water, add Et under ice-cooling 3 N and Boc 2 O stirring, the temperature naturally rises to room temperature and reacts for 4h, and TLC monitors that the reaction is complete. The reaction solution was spin-dried, and the residu...

Embodiment 2

[0049] Example 2: Gel performance of cystine cholesterol gelling factor in different solvents

[0050] In order to study the gelation ability of cystine-cholesterol gelling factor, a certain amount of cystine-cholesterol gelling factor was weighed, respectively added to different solvents (benzene solvents, n-propanol, cyclohexane, etc.), ultrasonically heated , after cooling to room temperature and standing for a period of time, observe its gel performance. The results are shown in Table 1:

[0051] Table 1 The gelation ability of cystine cholesterol gelling factor in different solvents

[0052]

[0053] Among them, TG is a transparent gel; OG is an opaque gel; I is insoluble during the heating process; P is dissolved first and then gradually precipitated; S is still in a solution state after cooling to room temperature. Measured 19 kinds of solvents respectively, and found that the gel factor can form gels in almost all benzene solvents such as benzene, toluene, chlorob...

Embodiment 3

[0054] Example 3: Microscopic morphology of gel formed by cystine-cholesterol gelling factor in different solvents

[0055] Scanning electron microscopy (SEM) was used to observe the morphology of the gel formed in each system, and it was found that the microscopic morphology of the gel formed by cystine-cholesterol gelling factor was very different in different solvents. The gel formed by cystine-cholesterol gelling factor in o-xylene and m-xylene can be seen that thick fibers with a diameter of 2-3 μm are intertwined and stacked ( figure 2 , image 3 ); in the gel formed in n-propanol, molecules aggregate to form a fibrous network structure, and fibers with a diameter of about 30nm are interlaced to form cavities of 50-100nm size ( Figure 4 ). These fibers are intertwined with each other, trapping the solvent in them to restrict the flow, forming a gel.

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Abstract

The invention relates to a cystine cholesterol gelator and a preparation method thereof. The gelator is obtained by taking natural products cholesterol and cystine as raw materials through chemical reaction. The invention also discloses supramolecular gel which is obtained by self-assembling the gel factor in a benzene solvent, normal propyl alcohol or cyclohexane and other solvents, and the microstructure of the supramolecular gel is of a regular nanobelt or nanofiber network structure. The raw materials adopted in the preparation process of the gelator and the supramolecular gel belong to natural small molecular compounds, have the advantages of wide source, good biocompatibility, unique structure and the like, and show better ion selective recognition and reduction response characteristics. The gel system disclosed by the invention has good biocompatibility and environmental friendliness. According to the technical scheme, a new thought is provided for construction of an intelligent response gel material, and a new reference is provided for expanding application of cystine and cholesterol natural small molecule compounds in the supramolecular field.

Description

technical field [0001] The invention relates to the technical field of supramolecular gels, in particular to a method for synthesizing cystine-cholesterol gelling factor with a "butterfly" molecular structure and a supramolecular gel preparation method. Background technique [0002] Due to its unique rheological properties, gel has unique advantages in many fields, and has been widely used in food, cosmetics, agriculture, medicine, sewage treatment and other fields. Among them, low-molecular-weight gels have attracted extensive attention from researchers due to their advantages such as easy design of molecular structure, easy regulation of properties, simple preparation methods, and sensitivity to external stimuli. At present, many building blocks have been used for the construction of low-molecular-weight gels, but the rational design of gel factor structures and the precise regulation of morphology and properties are still relatively difficult problems. At the same time, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J41/00C08J3/075C08L87/00C08G83/00C09K11/06G01N21/64
CPCC07J41/0055C08J3/075C08G83/008C09K11/06G01N21/6428C08J2387/00C09K2211/1416C09K2211/1433
Inventor 高玉霞杜凤沛赵克非张晨辉李子璐吴天岳
Owner CHINA AGRI UNIV
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