CN102584926B - Method for preparing supermolecule hydrogel based on amphiphilic micromolecules (cholesterol and phosphorylcholine) - Google Patents
Method for preparing supermolecule hydrogel based on amphiphilic micromolecules (cholesterol and phosphorylcholine) Download PDFInfo
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Abstract
本发明公开了一种利用基于胆固醇和磷酸胆碱的两亲小分子制备超分子水凝胶的方法。本发明选用生物分子胆固醇和磷酸胆碱作为两亲小分子的结构要素，水凝胶的生物相容性良好；分子的结构十分简单，不仅便于合成制备而且便于通过最简单的分子结构变化对水凝胶的性能进行调节；此外还具有水凝胶结构均匀，各种凝胶性能不会受外界pH值和离子强度等因素的变化而被破坏，对各种其他活性及功能性成分负载能力很强，保湿性良好等一系列优点。因此这种超分子水凝胶在组织工程、药物传递、细胞培养、化妆品、食品以及农林园艺等方面有非常广阔的潜在应用前景。The invention discloses a method for preparing a supramolecular hydrogel by using amphiphilic small molecules based on cholesterol and phosphorylcholine. The present invention selects biomolecules cholesterol and phosphorylcholine as structural elements of amphiphilic small molecules, and the biocompatibility of the hydrogel is good; the structure of the molecule is very simple, which is not only convenient for synthesis and preparation but also facilitates the modification of water through the simplest molecular structure change. In addition, it also has a uniform hydrogel structure, and various gel properties will not be damaged by changes in external pH and ionic strength, and it has a high loading capacity for various other active and functional components. Strong, good moisture retention and a series of advantages. Therefore, this supramolecular hydrogel has very broad potential application prospects in tissue engineering, drug delivery, cell culture, cosmetics, food, and agriculture, forestry and horticulture.
Description
技术领域 technical field
本发明涉及两亲小分子超分子水凝胶的制备方法，尤其涉及一种利用基于胆固醇和磷酸胆碱两亲小分子制备超分子水凝胶的方法。The invention relates to a preparation method of an amphiphilic small molecule supramolecular hydrogel, in particular to a method for preparing a supramolecular hydrogel based on amphiphilic small molecules based on cholesterol and phosphorylcholine.
背景技术 Background technique
水凝胶因其优异的性能一直受到广泛的关注，其应用已经遍及生物医用领域、日用化妆品、食品工业乃至农业等领域。进年来，研究的兴趣热点逐渐转移至两亲小分子形成的超分子水凝胶(LWHG)，因为这种水凝胶具有一系列特殊的优势：超分子水凝胶本身具有良好的可降解性，凝胶的性能更易于调控，凝胶过程具有可逆性和对外界的刺激具有更灵敏的响应性使其在制作智能响应材料方面具有更大的潜力。超分子水凝胶剂的合理设计和凝胶性能的灵活控制仍然是难于克服的问题。目前很多超分子水凝胶剂都采用糖或者寡肽作为亲水部分，这种设计所得到的水凝胶往往易于受到环境中pH值或者离子强度的影响被破坏而失去凝胶的形态；超分子水凝胶剂的分子结构往往比较复杂，这造成制备困难，不能够大规模生产；很多超分子水凝胶剂的结构中含有稠环芳烃等强致癌物质，其生物毒性方面存在问题。因此，目前超分子水凝胶的应用受到很大限制。Hydrogels have been widely concerned because of their excellent properties, and their applications have spread across the fields of biomedicine, daily cosmetics, food industry and even agriculture. In recent years, the focus of research has gradually shifted to the supramolecular hydrogel (LWHG) formed by amphiphilic small molecules, because this hydrogel has a series of special advantages: supramolecular hydrogel itself has good degradability , the performance of the gel is easier to control, the reversibility of the gel process and the more sensitive response to external stimuli make it have greater potential in the production of smart responsive materials. Rational design of supramolecular hydrogels and flexible control of gel properties are still formidable problems. At present, many supramolecular hydrogels use sugar or oligopeptide as the hydrophilic part. The hydrogels obtained by this design are often easily damaged by the pH value or ionic strength in the environment and lose their gel form; The molecular structure of molecular hydrogels is often complex, which makes preparation difficult and cannot be produced on a large scale; the structure of many supramolecular hydrogels contains strong carcinogens such as condensed ring aromatic hydrocarbons, and there are problems in their biological toxicity. Therefore, the current applications of supramolecular hydrogels are greatly limited.
良好的生物相容性是将LWHG用于生物医用领域的基本要求。选择生物体成分作为结构片段是构建生物相容性材料普遍采用的方法。所以本发明选用了生物分子胆固醇和磷酸胆碱相作为超分子水凝胶剂的主要部分，以获得良好的生物相容性。磷酸胆碱是细胞膜内的卵磷脂的极性基团。磷酸胆碱类的两性离子表面活性剂对环境中pH值和离子强度等因素表现出了良好的抗干扰能力，能够在很广泛的条件下使用。简单的分子结构是简化合成制备过程的先决条件，所以本发明采用简单的直线形单亲水基团分子结构，利用烷基链将胆固醇和磷酸胆碱相结合。这样不仅可以大大简化合成制备过程，而且可以方便的通过改变磷酸胆碱和胆固醇之间的烷基链的长度，或者改变磷酸胆碱之间的电荷中心的间距对所得超分子水凝胶的性能进行有效的调节。Good biocompatibility is the basic requirement for LWHG to be used in the biomedical field. Selecting biological components as structural fragments is a commonly used method for constructing biocompatible materials. Therefore, the present invention selects biomolecular cholesterol and phosphorylcholine as the main part of the supramolecular hydrogel to obtain good biocompatibility. Phosphocholine is the polar group of lecithin in cell membranes. Phosphorylcholine zwitterionic surfactants have good anti-interference ability to factors such as pH value and ionic strength in the environment, and can be used under a wide range of conditions. A simple molecular structure is a prerequisite for simplifying the synthesis and preparation process, so the present invention adopts a simple linear single-hydrophilic group molecular structure, and uses alkyl chains to combine cholesterol and phosphorylcholine. This not only greatly simplifies the synthesis and preparation process, but also can easily affect the performance of the obtained supramolecular hydrogel by changing the length of the alkyl chain between phosphorylcholine and cholesterol, or changing the distance between the charge centers between phosphorylcholine Make effective adjustments.
发明内容 Contents of the invention
本发明的目的是克服一般利用两亲小分子所制备的超分子水凝胶体系中的缺点，提供一种利用基于胆固醇和磷酸胆碱两亲小分子制备超分子水凝胶的方法。The purpose of the present invention is to overcome the disadvantages of the supramolecular hydrogel system generally prepared by using amphiphilic small molecules, and provide a method for preparing supramolecular hydrogels using amphiphilic small molecules based on cholesterol and phosphorylcholine.
利用基于胆固醇和磷酸胆碱的两亲小分子制备超分子水凝胶的方法是：将0.1g～1000g基于胆固醇和磷酸胆碱的两亲小分子同1mL～1000mL水混合，在30℃～100℃的恒定温度下，搅拌1～100h，倒入模具中，静置冷却1h～200h，得到超分子水凝胶。The method for preparing supramolecular hydrogels by using amphiphilic small molecules based on cholesterol and phosphorylcholine is: mix 0.1g～1000g amphiphilic small molecules based on cholesterol and phosphorylcholine with 1mL～1000mL water, Stirring for 1-100 hours at a constant temperature of °C, pouring into a mold, and standing for cooling for 1-200 hours to obtain a supramolecular hydrogel.
所述的基于胆固醇和磷酸胆碱的两亲小分子的分子结构式为：The molecular structural formula of the amphiphilic small molecule based on cholesterol and phosphorylcholine is:
其中m为0，2～20，n为2～8。Wherein, m is 0, 2-20, and n is 2-8.
本发明与现有技术相比具有的有益效果：The present invention has the beneficial effect compared with prior art:
1)制备过程中所采用的基于胆固醇和磷酸胆碱的两亲小分子具有制备合成过程简单高效，原料易于获取，价格低廉的特点；1) The amphiphilic small molecule based on cholesterol and phosphorylcholine used in the preparation process has the characteristics of simple and efficient preparation and synthesis process, easy access to raw materials, and low price;
2)水凝胶的制备程序简单直接、条件温和、易于操作，因此便于实际使用；2) The preparation procedure of the hydrogel is simple and direct, the conditions are mild, and it is easy to operate, so it is convenient for practical use;
3)所得到的水凝胶生物相容性优异，而且机械性能良好、结构均匀、保湿性良好；3) The obtained hydrogel has excellent biocompatibility, good mechanical properties, uniform structure, and good moisture retention;
4)所得到的水凝胶的性能可以十分方便的通过改变胆固醇和磷酸胆碱之间的烷基链的长度和磷酸胆碱中电荷中心的间距灵活地调节。4) The properties of the obtained hydrogel can be flexibly adjusted by changing the length of the alkyl chain between cholesterol and phosphocholine and the distance between charge centers in phosphocholine.
5)所得的水凝胶的性能不会受到水环境中的pH值、离子强度、溶质等因素的影响，这使得凝胶不仅具有优异的稳定性，而且可以混入各种功能性或者活性成分，因此这种水凝胶可以作为良好的载体使用。5) The performance of the obtained hydrogel will not be affected by factors such as pH value, ionic strength, and solute in the water environment, which makes the gel not only have excellent stability, but also can be mixed with various functional or active ingredients, Therefore, this hydrogel can be used as a good carrier.
附图说明 Description of drawings
图1是利用基于胆固醇和磷酸胆碱两亲小分子所制备的超分子水凝胶，m＝0，n＝3。Figure 1 is a supramolecular hydrogel prepared by amphiphilic small molecules based on cholesterol and phosphorylcholine, m=0, n=3.
图2是利用基于胆固醇和磷酸胆碱两亲小分子所制备的超分子水凝胶的动态模量测试，m＝0，n＝3，其中储能模量高于损耗模量，证明处于凝胶态。Figure 2 is the dynamic modulus test of supramolecular hydrogels prepared based on cholesterol and phosphorylcholine amphiphilic small molecules, m=0, n=3, where the storage modulus is higher than the loss modulus, which proves that in gelation Colloidal.
具体实施方式 Detailed ways
胆固醇和磷酸胆碱都是十分重要的生物分子，将二者通过直链烷基相结合制备的两亲小分子无毒性，生物相容性良好；胆固醇之间的较强疏水作用力可以有效地改善超分子水凝胶的各种性能；磷酸胆碱基团则可以赋予两亲分子良好的亲水性和抵抗水溶液中其它离子破坏能力；胆固醇和磷酸胆碱之间的烷基链和磷酸胆碱中电荷中心间距的变化可以灵活有效地对所制备的超分子水凝胶的性能进行调节。这种超分子水凝胶在组织工程、药物传递、细胞培养、化妆品、食品以及农林园艺等方面有非常广阔的潜在应用前景。Cholesterol and phosphorylcholine are both very important biomolecules. The amphiphilic small molecules prepared by combining the two through linear alkyl groups are non-toxic and have good biocompatibility; the strong hydrophobic interaction between cholesterol can effectively Improve the various properties of supramolecular hydrogels; the phosphorylcholine group can endow the amphiphile with good hydrophilicity and the ability to resist other ions in aqueous solution; the alkyl chain between cholesterol and phosphorylcholine and phosphorylcholine The variation of the distance between the charge centers in the base can flexibly and effectively tune the properties of the prepared supramolecular hydrogels. This supramolecular hydrogel has very broad potential application prospects in tissue engineering, drug delivery, cell culture, cosmetics, food, and agriculture, forestry and horticulture.
利用基于胆固醇和磷酸胆碱的两亲小分子制备超分子水凝胶的方法是：将0.1g～1000g基于胆固醇和磷酸胆碱的两亲小分子同1mL～1000mL水混合，在30℃～100℃的恒定温度下，搅拌1～100h，倒入模具中，静置冷却1h～200h，得到超分子水凝胶。The method for preparing supramolecular hydrogels by using amphiphilic small molecules based on cholesterol and phosphorylcholine is: mix 0.1g～1000g amphiphilic small molecules based on cholesterol and phosphorylcholine with 1mL～1000mL water, Stirring for 1-100 hours at a constant temperature of °C, pouring into a mold, and standing for cooling for 1-200 hours to obtain a supramolecular hydrogel.
所述的基于胆固醇和磷酸胆碱的两亲小分子的分子结构式为：The molecular structural formula of the amphiphilic small molecule based on cholesterol and phosphorylcholine is:
其中m为0，2～20，n为2～8。Wherein, m is 0, 2-20, and n is 2-8.
下面的实施例是对本发明的进一步说明，而不是限制本发明的范围。The following examples are to further illustrate the present invention, but not to limit the scope of the present invention.
实施例1Example 1
将0.1g基于胆固醇和磷酸胆碱的两亲小分子同200mL水混合，在80℃的恒定温度下，搅拌1h，倒入模具中，静置冷却1h，得到超分子水凝胶，Mix 0.1 g of amphiphilic small molecules based on cholesterol and phosphorylcholine with 200 mL of water, stir for 1 h at a constant temperature of 80 ° C, pour into a mold, and leave to cool for 1 h to obtain a supramolecular hydrogel.
基于胆固醇和磷酸胆碱的两亲小分子的分子结构式为：The molecular structural formula of the amphiphilic small molecule based on cholesterol and phosphorylcholine is:
其中m＝0，n＝2。where m=0, n=2.
实施例2：Example 2:
将1g基于胆固醇和磷酸胆碱的两亲小分子同100mL水混合，在80℃的恒定温度下，搅拌2h，倒入模具中，静置冷却2h，得到超分子水凝胶，Mix 1 g of amphiphilic small molecules based on cholesterol and phosphorylcholine with 100 mL of water, stir for 2 hours at a constant temperature of 80 ° C, pour into a mold, and let it stand for cooling for 2 hours to obtain a supramolecular hydrogel.
基于胆固醇和磷酸胆碱的两亲小分子的分子结构式为：The molecular structural formula of the amphiphilic small molecule based on cholesterol and phosphorylcholine is:
其中m＝0，n＝3。where m=0, n=3.
实施例3：Example 3:
将0.1g基于胆固醇和磷酸胆碱的两亲小分子同1mL水混合，在80℃的恒定温度下，搅拌3h，倒入模具中，静置冷却5h，得到超分子水凝胶，基于胆固醇和磷酸胆碱的两亲小分子的分子结构式为：Mix 0.1 g of amphiphilic small molecules based on cholesterol and phosphorylcholine with 1 mL of water, stir for 3 hours at a constant temperature of 80 ° C, pour into a mold, and let it stand for cooling for 5 hours to obtain a supramolecular hydrogel, based on cholesterol and The molecular structural formula of the amphiphilic small molecule of phosphorylcholine is:
其中m＝0，n＝4。where m=0, n=4.
实施例4：Example 4:
将3g基于胆固醇和磷酸胆碱的两亲小分子同100mL水混合，在70℃的恒定温度下，搅拌3h，倒入模具中，静置冷却5h，得到超分子水凝胶，Mix 3 g of amphiphilic small molecules based on cholesterol and phosphorylcholine with 100 mL of water, stir for 3 h at a constant temperature of 70 ° C, pour into a mold, and leave to cool for 5 h to obtain a supramolecular hydrogel.
基于胆固醇和磷酸胆碱的两亲小分子的分子结构式为：The molecular structural formula of the amphiphilic small molecule based on cholesterol and phosphorylcholine is:
其中m＝0，n＝5。where m=0, n=5.
实施例5：Example 5:
将5g基于胆固醇和磷酸胆碱的两亲小分子同100mL水混合，在45℃的恒定温度下，搅拌5h，倒入模具中，静置冷却6h，得到超分子水凝胶，Mix 5 g of amphiphilic small molecules based on cholesterol and phosphorylcholine with 100 mL of water, stir for 5 h at a constant temperature of 45 ° C, pour into a mold, and leave to cool for 6 h to obtain a supramolecular hydrogel.
基于胆固醇和磷酸胆碱的两亲小分子的分子结构式为：The molecular structural formula of the amphiphilic small molecule based on cholesterol and phosphorylcholine is:
其中m＝6，n＝2。where m=6, n=2.
实施例6：Embodiment 6:
将10g基于胆固醇和磷酸胆碱的两亲小分子同100mL水混合，在80℃的恒定温度下，搅拌5h，倒入模具中，静置冷却8h，得到超分子水凝胶，Mix 10g of amphiphilic small molecules based on cholesterol and phosphorylcholine with 100mL of water, stir at a constant temperature of 80°C for 5h, pour into a mold, and let it stand for cooling for 8h to obtain a supramolecular hydrogel.
基于胆固醇和磷酸胆碱的两亲小分子的分子结构式为：The molecular structural formula of the amphiphilic small molecule based on cholesterol and phosphorylcholine is:
其中m＝6，n＝3。where m=6, n=3.
实施例7：Embodiment 7:
将20g基于胆固醇和磷酸胆碱的两亲小分子同100mL水混合，在80℃的恒定温度下，搅拌5h，倒入模具中，静置冷却8h，得到超分子水凝胶，Mix 20g of amphiphilic small molecules based on cholesterol and phosphorylcholine with 100mL of water, stir for 5h at a constant temperature of 80°C, pour into a mold, and let it stand for cooling for 8h to obtain a supramolecular hydrogel.
基于胆固醇和磷酸胆碱的两亲小分子的分子结构式为：The molecular structural formula of the amphiphilic small molecule based on cholesterol and phosphorylcholine is:
其中m＝6，n＝5。where m=6, n=5.
实施例8：Embodiment 8:
将30g基于胆固醇和磷酸胆碱的两亲小分子同100mL水混合，在30℃的恒定温度下，搅拌5h，倒入模具中，静置冷却8h，得到超分子水凝胶，Mix 30g of amphiphilic small molecules based on cholesterol and phosphorylcholine with 100mL of water, stir for 5h at a constant temperature of 30°C, pour into a mold, and let it stand for cooling for 8h to obtain a supramolecular hydrogel.
基于胆固醇和磷酸胆碱的两亲小分子的分子结构式为：The molecular structural formula of the amphiphilic small molecule based on cholesterol and phosphorylcholine is:
其中m＝10，n＝2。where m=10, n=2.
实施例9：Embodiment 9:
将30g基于胆固醇和磷酸胆碱的两亲小分子同100mL水混合，在85℃的恒定温度下，搅拌5h，倒入模具中，静置冷却10h，得到超分子水凝胶，Mix 30g of amphiphilic small molecules based on cholesterol and phosphorylcholine with 100mL of water, stir for 5h at a constant temperature of 85°C, pour into a mold, and let it stand for cooling for 10h to obtain a supramolecular hydrogel.
基于胆固醇和磷酸胆碱的两亲小分子的分子结构式为：The molecular structural formula of the amphiphilic small molecule based on cholesterol and phosphorylcholine is:
其中m＝15，n＝2。where m=15, n=2.
实施例10：Example 10:
将20g基于胆固醇和磷酸胆碱的两亲小分子同80mL水混合，在85℃的恒定温度下，搅拌5h，倒入模具中，静置冷却12h，得到超分子水凝胶，Mix 20g of amphiphilic small molecules based on cholesterol and phosphorylcholine with 80mL of water, stir for 5h at a constant temperature of 85°C, pour into a mold, and let it stand for cooling for 12h to obtain a supramolecular hydrogel.
基于胆固醇和磷酸胆碱的两亲小分子的分子结构式为：The molecular structural formula of the amphiphilic small molecule based on cholesterol and phosphorylcholine is:
其中m＝16，n＝2。where m=16, n=2.
实施例11：Example 11:
将30g基于胆固醇和磷酸胆碱的两亲小分子同100mL水混合，在100℃的恒定温度下，搅拌6h，倒入模具中，静置冷却10h，得到超分子水凝胶，Mix 30g of amphiphilic small molecules based on cholesterol and phosphorylcholine with 100mL of water, stir for 6h at a constant temperature of 100°C, pour into a mold, and let it stand for cooling for 10h to obtain a supramolecular hydrogel.
基于胆固醇和磷酸胆碱的两亲小分子的分子结构式为：The molecular structural formula of the amphiphilic small molecule based on cholesterol and phosphorylcholine is:
其中m＝18，n＝2。where m=18, n=2.
实施例12：Example 12:
将1000g基于胆固醇和磷酸胆碱的两亲小分子同1000mL水混合，在85℃的恒定温度下，搅拌100h，倒入模具中，静置冷却200h，得到超分子水凝胶，Mix 1000g of amphiphilic small molecules based on cholesterol and phosphorylcholine with 1000mL of water, stir for 100h at a constant temperature of 85°C, pour into a mold, and let it stand for cooling for 200h to obtain a supramolecular hydrogel.
基于胆固醇和磷酸胆碱的两亲小分子的分子结构式为：The molecular structural formula of the amphiphilic small molecule based on cholesterol and phosphorylcholine is:
其中m＝20，n＝2。where m=20, n=2.
实施例13：Example 13:
将10g基于胆固醇和磷酸胆碱的两亲小分子同500mL水混合，在85℃的恒定温度下，搅拌4h，倒入模具中，静置冷却8h，得到超分子水凝胶，Mix 10 g of amphiphilic small molecules based on cholesterol and phosphorylcholine with 500 mL of water, stir for 4 hours at a constant temperature of 85 ° C, pour into a mold, and let it stand for cooling for 8 hours to obtain a supramolecular hydrogel.
基于胆固醇和磷酸胆碱的两亲小分子的分子结构式为：The molecular structural formula of the amphiphilic small molecule based on cholesterol and phosphorylcholine is:
其中m＝0，n＝8。where m=0, n=8.
实施例14：Example 14:
将10g基于胆固醇和磷酸胆碱的两亲小分子同500mL水混合，在85℃的恒定温度下，搅拌4h，倒入模具中，静置冷却8h，得到超分子水凝胶，Mix 10 g of amphiphilic small molecules based on cholesterol and phosphorylcholine with 500 mL of water, stir for 4 hours at a constant temperature of 85 ° C, pour into a mold, and let it stand for cooling for 8 hours to obtain a supramolecular hydrogel.
基于胆固醇和磷酸胆碱的两亲小分子的分子结构式为：The molecular structural formula of the amphiphilic small molecule based on cholesterol and phosphorylcholine is:
其中m＝2，n＝2。where m=2, n=2.
实施例15：Example 15:
将10g基于胆固醇和磷酸胆碱的两亲小分子同500mL水混合，在85℃的恒定温度下，搅拌4h，倒入模具中，静置冷却8h，得到超分子水凝胶，Mix 10 g of amphiphilic small molecules based on cholesterol and phosphorylcholine with 500 mL of water, stir for 4 hours at a constant temperature of 85 ° C, pour into a mold, and let it stand for cooling for 8 hours to obtain a supramolecular hydrogel.
基于胆固醇和磷酸胆碱的两亲小分子的分子结构式为：The molecular structural formula of the amphiphilic small molecule based on cholesterol and phosphorylcholine is:
其中m＝2，n＝8。where m=2, n=8.
实施例16：Example 16:
将50g基于胆固醇和磷酸胆碱的两亲小分子同1000mL水混合，在85℃的恒定温度下，搅拌10h，倒入模具中，静置冷却15h，得到超分子水凝胶，Mix 50g of amphiphilic small molecules based on cholesterol and phosphorylcholine with 1000mL of water, stir at a constant temperature of 85°C for 10h, pour into a mold, and let it stand for cooling for 15h to obtain a supramolecular hydrogel.
基于胆固醇和磷酸胆碱的两亲小分子的分子结构式为：The molecular structural formula of the amphiphilic small molecule based on cholesterol and phosphorylcholine is:
其中m＝20，n＝6。where m=20, n=6.
实施例17：Example 17:
将50g基于胆固醇和磷酸胆碱的两亲小分子同1000mL水混合，在85℃的恒定温度下，搅拌100h，倒入模具中，静置冷却200h，得到超分子水凝胶，Mix 50g of amphiphilic small molecules based on cholesterol and phosphorylcholine with 1000mL of water, stir for 100h at a constant temperature of 85°C, pour into a mold, and let it stand for cooling for 200h to obtain a supramolecular hydrogel.
基于胆固醇和磷酸胆碱的两亲小分子的分子结构式为：The molecular structural formula of the amphiphilic small molecule based on cholesterol and phosphorylcholine is:
其中m＝20，n＝8。where m=20, n=8.
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