CN110025827B - Water-retaining two-component hydrogel containing natural plant polysaccharide and preparation method and application thereof - Google Patents
Water-retaining two-component hydrogel containing natural plant polysaccharide and preparation method and application thereof Download PDFInfo
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- CN110025827B CN110025827B CN201910237169.1A CN201910237169A CN110025827B CN 110025827 B CN110025827 B CN 110025827B CN 201910237169 A CN201910237169 A CN 201910237169A CN 110025827 B CN110025827 B CN 110025827B
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Abstract
The invention discloses a water-retaining two-component hydrogel containing natural plant polysaccharide, a preparation method and application thereof, wherein the two-component hydrogel comprises a low-molecular-weight gel factor and the natural plant polysaccharide; the concentration ratio of the low molecular weight gelator to the natural plant polysaccharide is 2:8-8: 2. The water-retaining double-component hydrogel is a mixed gel with an interpenetrating network structure; the mixed gel is interpenetrated through a physical network structure to form a compact and disordered crosslinking structure, so that the dehydration shrinkage phenomenon of the pure carrageenan gel can be weakened or even inhibited, and the gel can obviously improve the capacity of the gel as a cell culture scaffold. The preparation method of the mixed gel is convenient to operate and has practical application value.
Description
Technical Field
The invention relates to the field of natural plant polysaccharide modification and tissue engineering scaffold materials, in particular to a water-retaining two-component hydrogel containing natural plant polysaccharide and capable of being used for cell culture, and a preparation method and application thereof.
Background
Carrageenan (also called carrageenin and carrageenin) is an algae gum extracted from Red marine algae (Red agar, Rhodophyta) and is a natural polysaccharide, wherein Carrageenan molecules are an alternating copolymer formed by β - (1 → 3) -D-galactose-4-sulfate and α - (1 → 4) -3, 6-inner ether-D-galactose, has excellent thermal reversible gelling property, no toxicity, hydrophilicity, stable dispersion, good film forming property and the like, and is widely applied to the fields of food, medicine, daily chemical industry, packaging and the like+) The kappa-carrageenan can be promoted to form hydrogel with larger elasticity and hardness, but the bleeding property (syneresis phenomenon) of the carrageenan is also caused. This bleeding greatly limits the use of carrageenan in tissue engineering.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide a water-retaining two-component hydrogel containing natural plant polysaccharide for a cell culture scaffold in tissue engineering, and a preparation method and application thereof. The water-retaining double-component hydrogel is a mixed gel with an interpenetrating network structure; the mixed gel is interpenetrated through a physical network structure to form a compact and disordered crosslinking structure, so that the dehydration shrinkage phenomenon of the pure carrageenan gel can be weakened or even inhibited, and the gel can obviously improve the capacity of the gel as a cell culture scaffold. The preparation method of the mixed gel is convenient to operate and has practical application value.
The purpose of the invention is realized by the following technical scheme:
the invention provides a water-retaining double-component hydrogel containing natural plant polysaccharide, which is characterized in that the double components comprise low-molecular-weight gel factors and natural plant polysaccharide; the concentration ratio of the low molecular weight gelator to the natural plant polysaccharide is 2:8-8: 2.
more preferably, the concentration ratio of the low molecular weight gelator to the natural plant polysaccharide is 4: 6-8: 2.
preferably, the low molecular weight gelator is 1, 4-phenyl phenylalanine diethylene glycol, and the structural formula is shown as the following formula:
the natural plant polysaccharide is kappa-carrageenan, and the structure is shown as the following formula:
preferably, the preparation method of the 1, 4-phenyl phenylalanine diethyl acetal comprises the following steps:
s1, adding triethylamine into the L-phenylalanine methyl ester hydrochloride, adding paraphthaloyl chloride, and stirring to react to obtain a product 1, 4-phenylalanine methyl ester;
s2, adding an alkali solution into the 1, 4-phenylalanine methyl ester, stirring for reaction, and adjusting the pH value of the reaction solution to be less than 3 to obtain a product 1, 4-phenylalanine;
s3, adding 1, 4-phenyl phenylalanine into diethylene glycol, dropwise adding concentrated hydrochloric acid, and stirring to react to obtain the product 1, 4-phenyl phenylalanine diethylene glycol.
Preferably, in the step S1, the molar ratio of the terephthaloyl chloride, the L-phenylalanine methyl ester hydrochloride and the triethylamine is 1:2: 6.
Preferably, in step S1, the L-phenylalanine methyl ester hydrochloride is cooled to 0 ℃ and then triethylamine is added, the stirring reaction time is 12-16 hours, and the stirring speed is 60 rpm.
Preferably, in step S2, the stirring reaction is performed at room temperature for 20 to 24 hours at a stirring speed of 60 rpm.
Preferably, in step S3, the stirring reaction time is 3 to 5 hours, the stirring speed is 60 rpm, and the reaction temperature is 20 to 50 ℃.
The invention also provides a preparation method of the water-retaining double-component hydrogel containing the natural plant polysaccharide, which is characterized by comprising the following steps:
and (2) taking potassium chloride as a cross-linking agent, blending the low-molecular-weight gel factor and the natural plant polypeptide, heating for dissolving, and cooling to obtain the double-component hydrogel.
The invention also provides the application of the water-retaining double-component hydrogel containing the natural plant polysaccharide in the tissue engineering cell culture scaffold material.
Compared with the prior art, the invention has the following beneficial effects:
the water-retaining double-component hydrogel containing the natural plant polysaccharide is a mixed gel with an interpenetrating network structure; the mixed gel has a compact and disordered network structure, so that the dehydration shrinkage phenomenon of the pure carrageenan gel can be weakened or even inhibited; the mixed gel is used for cell culture, the capability of the mixed gel as a cell culture bracket can be obviously improved, and the cell survival rate can reach more than 90 percent. The preparation method of the mixed gel is convenient to operate and easy for mass production. The invention also provides a feasible idea for solving the dehydration shrinkage phenomenon of the rest hydrogel, and the dehydration shrinkage phenomenon of the hydrophilic gel can be effectively improved even if the super-molecular weight gel factor B2 with the concentration ratio of 0.2% is mixed, so that the invention has economic and practical values.
Drawings
Other features, objects and advantages of the invention will become more apparent upon reading of the detailed description of non-limiting embodiments with reference to the following drawings:
FIG. 1 is a graph of hydrophilicity curves for different concentrations of neat kappa-carrageenan gel for 1, 3, 5, 7, and 14 days;
FIG. 2 is a graph of pure kappa-carrageenan gel of different concentrations and a two-component hydrogel of the present invention after standing for 30 days at room temperature;
FIG. 3 shows the cell culture conditions of different concentrations of pure kappa-carrageenan gel and the two-component water mixed gel of the present invention, wherein FIG. 3a shows pure carrageenan and FIG. 3b shows two-component hydrogel.
Detailed Description
The present invention will be described in detail with reference to specific examples. The following examples will assist those skilled in the art in further understanding the invention, but are not intended to limit the invention in any way. It should be noted that it would be obvious to those skilled in the art that various changes and modifications can be made without departing from the spirit of the invention. All falling within the scope of the present invention.
Example 1 preparation of Water-retentive two-component hydrogel containing Natural plant polysaccharide
The preparation of the water-retaining two-component hydrogel containing the natural plant polysaccharide comprises the following steps:
(a) taking phthaloyl chloride, L-phenylalanine methyl ester hydrochloride and triethylamine; the molar ratio of the phthaloyl chloride to the L-phenylalanine methyl ester hydrochloride to the triethylamine is 1:2: 6; the starting materials are all available from published commercial sources;
(b) cooling the anhydrous dichloromethane solution of L-phenylalanine methyl ester hydrochloride to 0 ℃, adding triethylamine, and adding the anhydrous dichloromethane solution of terephthaloyl chloride to obtain a reaction solution; slowly heating the reaction solution to room temperature and stirring for 12-16 hours;
(c) performing rotary evaporation on the reaction solution, adding deionized water, filtering, collecting precipitate, recrystallizing the obtained precipitate with ethanol, filtering, and drying in an oven for 10-12 hours at the drying temperature of 50-60 ℃ to obtain a product 1, 4-phenylalanine methyl ester;
(d) adding 2M sodium hydroxide solution into methanol solution of 1, 4-phenyl phenylalanine methyl ester, stirring the reaction mixture at room temperature for 20-24 hours, adjusting the pH value of the reaction solution to be less than 3 by using 3M hydrochloric acid solution, filtering, collecting generated precipitate, and drying in vacuum to obtain 1, 4-phenyl phenylalanine;
(e) adding 1, 4-phenyl phenylalanine into diethylene glycol, dropwise adding concentrated hydrochloric acid, and stirring for reacting for 3-5 hours until the solution is clear. Adding the obtained solution into an ice-water mixture to obtain gelatinous precipitate, performing suction filtration to collect a filter cake, washing the filter cake with a large amount of ultrapure water, drying the filter cake in an oven for 10 to 12 hours at the drying temperature of between 50 and 60 ℃ to obtain 1, 4-phenyl phenylalanine diethylene glycol (B2), wherein the structural formula of the 1, 4-phenyl phenylalanine diethylene glycol is shown as the following formula:
(f) dissolving kappa-carrageenan (kappa-CG) in distilled water by using water bath, adding a proper amount of potassium chloride (KCl) as a cross-linking agent, sucking the kappa-carrageenan (kappa-CG) solution, blending, heating and dissolving after 1, 4-phenyl phenylalanine diethylene glycol diester (B2) is heated and dissolved, and cooling to room temperature to form the two-component gel.
Example 2 Water-Retention test of Water-Retention two-component hydrogel containing Natural plant polysaccharide
First, pure kappa-carrageenan gels with potassium ion crosslinking (potassium ion concentration of 3mg/ml) concentration of 2, 4, 6, 8, 10mg/ml were prepared, 1ml of each gel was put into a 24-well plate and a 5ml glass bottle, and the bottles were sealed and left at room temperature. The water exuded from each 24-well plate at time intervals of 1, 3, 5, 7 and 14 days was pipetted and placed under an electronic balance to be weighed, recorded and repeated 3 times. The water retention curve is shown in fig. 1, when the content of kappa-carrageenan is 2mg/ml, the hydrogel begins to lose water after three days, but the water retention effect of the hydrogel becomes better and better with the increase of the content of kappa-carrageenan, and when the content reaches 10mg/ml, the hydrogel can completely retain water.
Secondly, preparing 10mg/ml pure kappa-carrageenan gel crosslinked by potassium ions (the concentration of the potassium ions is 3mg/ml), blending the pure kappa-carrageenan gel with 10mg/ml 1, 4-phenyl phenylalanine diethylene glycol (B2) solution to prepare two-component hydrogel with the concentration ratios of 8:2, 6:4, 4:6, 2:8 and 0:10, respectively adding 1ml of the two-component hydrogel into a glass bottle with the volume of 5ml, and sealing and placing the two-component hydrogel at room temperature.
After 30 days, comparing the water retention conditions of pure kappa-carrageenan gel with different concentrations and two-component hydrogel with different concentration ratios. The results are shown in fig. 2, and it can be seen from fig. 2 that pure kappa-carrageenan with different concentrations loses water with time, while the two-component hydrogel containing kappa-carrageenan has a good water retention effect, and particularly, the water retention effect is better as the concentration of kappa-carrageenan increases.
Example 3 Water-retentive two-component hydrogel cell culture experiment containing Natural plant polysaccharide
Adding 100 μ l of pure kappa-carrageenan gel with concentration of 2, 4, 6, 8, 10mg/ml, pure B2 gel with concentration of 10mg/ml, and two-component hydrogel with concentration ratio of 10mg/ml kappa-carrageenan gel to B2 of 8:2, 6:4, 4:6, 2:8, 0:10 into 96-well plate, and after gelling, sucking 100 μ l of 1 × 10 density4The HCT 116 cell suspension of (A) was added to the above well plate, covered with hydrogel and placed at 37 ℃ with 5% CO2After culturing in the incubator for 12, 24, 36, 48 and 72 hours respectively, 10 mul of cell counting reagent (CCK-8) is added, after incubation for 4 hours at 37 ℃, absorbance is detected by using absorption wavelength of 450nm, and the experiment is repeated for 5 times. As a result, as shown in fig. 3a, kappa-carrageenan has some biocompatibility, but is inferior to Polystyrene (PS). As shown in FIG. 3b, it is apparent that the biocompatibility of the cells is improved if the hydrogel is prepared by mixing kappa-carrageenan with gelator. These are all strongly related to the water retention effect of hydrogels.
The foregoing description of specific embodiments of the present invention has been presented. It is to be understood that the present invention is not limited to the specific embodiments described above, and that various changes or modifications may be made by one skilled in the art within the scope of the appended claims without departing from the spirit of the invention. The embodiments and features of the embodiments of the present application may be combined with each other arbitrarily without conflict.
Claims (8)
1. A water-retaining two-component hydrogel containing natural plant polysaccharide is characterized in that the two components comprise low-molecular-weight gel factors and natural plant polysaccharide; the concentration ratio of the low molecular weight gelator to the natural plant polysaccharide is 6: 4; the total concentration of the low molecular weight gelator and the natural plant polysaccharide is 10 mg/mL;
the natural plant polysaccharide is kappa-carrageenan, and the structure is shown as the following formula:
the preparation method of the water-retaining two-component hydrogel containing the natural plant polysaccharide comprises the following steps:
and (2) taking potassium chloride as a cross-linking agent, blending the low-molecular-weight gel factor and the natural plant polysaccharide, heating and dissolving, and cooling to obtain the double-component hydrogel.
2. The water-retaining two-component hydrogel containing natural plant polysaccharides of claim 1, wherein the molecular weight gelator is 1, 4-phenyl phenylalanine diethylene glycol, and the structural formula is shown as the following formula:
3. the water-retaining two-component hydrogel containing natural plant polysaccharides as claimed in claim 2, wherein the preparation method of the 1, 4-phenyl phenylalanine diethylene glycol comprises the following steps:
s1, adding triethylamine into the L-phenylalanine methyl ester hydrochloride, adding paraphthaloyl chloride, and stirring to react to obtain a product 1, 4-phenylalanine methyl ester;
s2, adding an alkali solution into the 1, 4-phenylalanine methyl ester, stirring for reaction, and adjusting the pH value of the reaction solution to be less than 3 to obtain a product 1, 4-phenylalanine;
s3, adding 1, 4-phenyl phenylalanine into diethylene glycol, dropwise adding concentrated hydrochloric acid, and stirring to react to obtain the product 1, 4-phenyl phenylalanine diethylene glycol.
4. The water-retentive two-component hydrogel of claim 3, wherein in step S1, the molar ratio of terephthaloyl chloride, L-phenylalanine methyl ester hydrochloride and triethylamine is (1. + -. 0.5): (2. + -. 0.5): (6. + -. 1).
5. The water-retentive two-component hydrogel of claim 3, wherein in step S1, the L-phenylalanine methyl ester hydrochloride is cooled to 0 ℃ and triethylamine is added thereto, the stirring reaction is carried out for 12 to 16 hours at a stirring speed of 60 rpm.
6. The water-retentive two-component hydrogel according to claim 3, wherein in step S2, the stirring reaction is carried out at room temperature for 20 to 24 hours at a stirring speed of 60 rpm.
7. The water-retentive two-component hydrogel of claim 3, wherein in step S3, the stirring reaction time is 3 to 5 hours, the stirring speed is 60 rpm, and the reaction temperature is 20 to 50 ℃.
8. Use of the water-retaining two-component hydrogel containing natural plant polysaccharides according to any one of claims 1 to 7 in a scaffold material for tissue engineering cell culture.
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