CN103694131A - Chiral supermolecule hydrogel and preparation method and application thereof - Google Patents
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Abstract
The invention provides a chiral supermolecule hydrogel and a preparation method and application thereof. The structural formula of the chiral supermolecule hydrogel is shown in the specification, wherein R1 is H or COOEtOEtOH, and R2 is H or COOEtOEtOH. The invention also relates to the preparation method and application of the chiral supermolecule hydrogel. The chiral supermolecule hydrogel can be used as a cytoskeleton material; the process of regulating and controlling the cell selective adhesion by the chiral supermolecule hydrogel is carried out in physiological environment and is convenient to operate; the chiral supermolecule hydrogel has practical application value; the preparation method does not need complicated synthesis steps and is beneficial for large scale industrial production; the prepared product has high purity and good dispersibility, and is applicable to cell culture and controllable adhesives in commerce.
Description
Technical field
The invention belongs to medical science or field of tissue engineering technology, especially a kind of chirality supramolecular hydrogel and preparation method thereof, purposes.
Background technology
Human tissue injury, damaged meeting cause dysfunction, traditional restorative procedure is autograft art, although can obtain satisfactory effect, but it is to sacrifice the way that autologous health tissues is cost, can cause a lot of complication and episome organ origin very limited, because immunological rejection needs life-time service immunosuppressor, the complication of bringing is therefrom fatal sometimes.According to incompletely statistics, there are every year many people to be damaged by burned skin, cornea or bone fractures etc., to victim, bring painful time, also have a strong impact on their daily orthobiosis.Therefore tissue regeneration medical science has become the significant problem that Now Domestic is badly in need of solution outward.Medically conventional artificial tissue and organ etc. due to do not have biological activity, have even with pathogenicity bo, and some material preparation costs is expensive, medical science high cost, makes its application limited.
Summary of the invention
For defect of the prior art, the object of this invention is to provide a kind of chirality supramolecular hydrogel and preparation method thereof, purposes.
The present invention is achieved by the following technical solutions:
First aspect, the invention provides a kind of chirality supramolecular hydrogel, and described chirality supramolecular hydrogel is that Isosorbide-5-Nitrae-phenyl ring is the phenylalanine derivative of core, and the structural formula of described derivative is as follows:
Wherein, R
1for H or COOEtOEtOH,
R
2for H or COOEtOEtOH.
Second aspect, the present invention relates to the preparation method of aforesaid chirality supramolecular hydrogel, and described method comprises the steps:
Step 2, the anhydrous methylene chloride solution of L-Phe methyl ester hydrochloride is cooling, add successively triethylamine, p-phthaloyl chloride, obtain reaction soln, reaction soln is slowly risen to room temperature and stirs;
Step 3, rotary evaporation reaction soln, adds deionized water, filters collecting precipitation;
Step 4, by gained precipitation ethyl alcohol recrystallization, filters, dry, obtains product Isosorbide-5-Nitrae-phenyl phenylalanine methyl ester;
Step 5 adds sodium hydroxide solution in the methanol solution of Isosorbide-5-Nitrae-phenyl phenylalanine methyl ester, and stirring reaction under room temperature is adjusted to pH with hydrochloric acid soln and is less than 3, filters, and collects generate precipitation vacuum-drying, obtains Isosorbide-5-Nitrae-phenyl phenylalanine;
Step 6, by Isosorbide-5-Nitrae-phenyl phenylalanine and glycol ether generation acid catalysis generation esterification, obtains final product chirality supramolecular hydrogel.
Preferably, in step 1, the mol ratio of described p-phthaloyl chloride, L-Phe methyl ester hydrochloride, triethylamine is 2:3:4～1:4:10.
Preferably, in step 2, described cooling temperature is 0 ℃, and the time of described stirring is 12～16 hours.
Preferably, in step 2, the volumetric molar concentration of the anhydrous methylene chloride solution of described L-Phe methyl ester hydrochloride is 0.02～0.5mol/L, and the volumetric molar concentration of the anhydrous methylene chloride solution of described p-phthaloyl chloride is 0.05～0.5mol/L.
Preferably, in step 3, the consumption of described deionized water is 10～20mL.
Preferably, in step 4, the concentration 50～95% of described ethanol, dry temperature is 50～95 ℃, the time is 3～24h.
Preferably, in step 5, described sodium hydroxide solution is 1～3M, and described hydrochloric acid soln is 2～6M, and described churning time is 20～24 hours.
Preferably, in step 6, the mass ratio of described Isosorbide-5-Nitrae-phenyl phenylalanine and glycol ether generation esterification is 1:1～1:10.
The third aspect, the present invention relates to the purposes of aforesaid chirality supramolecular hydrogel, and described chirality supramolecular hydrogel can be used for cytoskeleton material.
Compared with prior art, the present invention has following beneficial effect:
(1) chirality supramolecular hydrogel of the present invention can be used for cytoskeleton material, is the biomimetic cell scaffolds material with the selective attachment of the chirality regulating cell by nanofiber;
(2) the selective attachment process of chirality supramolecular hydrogel regulating cell of the present invention is carried out under physiological environment, easy to operate, has actual application value.
(3) preparation method of the super chirality supramolecular hydrogel of the present invention, without complicated synthesis step, is easy to industrial production in enormous quantities, and products therefrom purity is high, and good dispersity is suitable for commercialization and uses for cell cultures and controlled adhesive agent.
Accompanying drawing explanation
By reading the detailed description of non-limiting example being done with reference to the following drawings, it is more obvious that other features, objects and advantages of the present invention will become:
Fig. 1 is that supramolecular hydrogel of the present invention adds complete cell culture fluid fore-and-aft stability photo comparison diagram; Wherein, (a, d is 0 minute; B, after e is 30 minutes; C, after f is 20 days);
Fig. 2 is the fluorescent dye photo comparison diagram of NIH3T3, the cell adhesion of HUVEC cell in the two-dimensional film of supramolecular hydrogel of the present invention;
Fig. 3 is the fluorescent dye photo comparison diagram of NIH3T3, HUVEC cell cell adhesion and growth in the three-dimensional microenvironment of supramolecular hydrogel of the present invention;
Fig. 4 is the spectrogram of supramolecular hydrogel of the present invention, (4A) for embodiment 1, make the spectrogram of supramolecular hydrogel, (4B) for embodiment 2, make the spectrogram of supramolecular hydrogel, (4C) for embodiment 3, make the spectrogram of supramolecular hydrogel, (4D) for embodiment 4, make the spectrogram of supramolecular hydrogel;
Fig. 5 is the fibre shape figure of supramolecular hydrogel of the present invention, and wherein, a is right-handed helix, and b is left hand helix.
Embodiment
Below in conjunction with specific embodiment, the present invention is described in detail.Following examples will contribute to those skilled in the art further to understand the present invention, but not limit in any form the present invention.It should be pointed out that to those skilled in the art, without departing from the inventive concept of the premise, can also make some distortion and improvement.These all belong to protection scope of the present invention.
The present embodiment relates to a kind of chirality supramolecular hydrogel, and described chirality supramolecular hydrogel is that Isosorbide-5-Nitrae-phenyl ring is the phenylalanine derivative of core, and the structural formula of described derivative is as follows:
Wherein, R
1for H
R
2for COOEtOEtOH.
The present embodiment also relates to the preparation method of aforementioned chirality supramolecular hydrogel, and described method comprises:
Step 2, the anhydrous methylene chloride solution 10～40mL by L-Phe methyl ester hydrochloride, is cooled to 0 ℃, adds triethylamine, then adds p-phthaloyl chloride 5～10mL, obtains reaction soln; Reaction soln is slowly risen to room temperature and stir 12～16 hours;
Step 3, rotary evaporation reaction solution, adds deionized water 10～20mL, filters collecting precipitation;
Step 4, ethanol 5-15mL recrystallization for gained precipitation, filters and be dried 10 to 12 hours in baking oven, and 50 ℃ to 60 ℃ of drying temperatures, obtain product Isosorbide-5-Nitrae-phenyl phenylalanine methyl ester;
Step 5, to 1, in the methanol solution of 4-phenyl phenylalanine methyl ester, add 2M sodium hydroxide solution, reaction mixture is stirring reaction 20～24 hours at room temperature, with 3M hydrochloric acid soln, reacting liquid pH value is adjusted to and is less than 3, filter and collect generate precipitation vacuum-drying, obtain dye sorbent Isosorbide-5-Nitrae-phenyl phenylalanine;
Step 6, by Isosorbide-5-Nitrae-phenyl phenylalanine and glycol ether generation acid-catalyzed esterification reaction, obtains final product chirality supramolecular hydrogel, and as shown in Figure 5, wherein, a is right-handed helix to the fibre shape figure of described supramolecular hydrogel, and b is left hand helix.
embodiment 2
The present embodiment relates to a kind of chirality supramolecular hydrogel, and described chirality supramolecular hydrogel is that Isosorbide-5-Nitrae-phenyl ring is the phenylalanine derivative of core, and the structural formula of described derivative is as follows:
Wherein, R
1for COOEtOEtOH,
R
2for H.
The present embodiment also relates to the preparation method of aforementioned chirality supramolecular hydrogel, and described method comprises:
Step 2, the anhydrous methylene chloride solution 10mL by L-Phe methyl ester hydrochloride, is cooled to 0 ℃, adds triethylamine, then adds p-phthaloyl chloride 5mL, obtains reaction soln; Reaction soln is slowly risen to room temperature and stir 12 hours;
Step 3, rotary evaporation reaction solution, adds deionized water 10mL, filters collecting precipitation;
Step 4, ethanol 5mL recrystallization for gained precipitation, filters and be dried 10 hours in baking oven, and 50 ℃ to 60 ℃ of drying temperatures, obtain product Isosorbide-5-Nitrae-phenyl phenylalanine methyl ester;
Step 5, to 1, in the methanol solution of 4-phenyl phenylalanine methyl ester, add 2M sodium hydroxide solution, reaction mixture is stirring reaction 20～24 hours at room temperature, with 3M hydrochloric acid soln, reacting liquid pH value is adjusted to and is less than 3, filter and collect generate precipitation vacuum-drying, obtain dye sorbent Isosorbide-5-Nitrae-phenyl phenylalanine;
Step 6, by Isosorbide-5-Nitrae-phenyl phenylalanine and glycol ether generation acid-catalyzed esterification reaction, obtains final product chirality supramolecular hydrogel, and as shown in Figure 5, wherein, a is right-handed helix to the fibre shape figure of described supramolecular hydrogel, and b is left hand helix.
embodiment 3
The present embodiment relates to a kind of chirality supramolecular hydrogel, and described chirality supramolecular hydrogel is that Isosorbide-5-Nitrae-phenyl ring is the phenylalanine derivative of core, and the structural formula of described derivative is as follows:
Wherein, R
1for COOEtOEtOH,
R
2for H.
The present embodiment also relates to the preparation method of aforementioned chirality supramolecular hydrogel, and described method comprises:
Step 2, the anhydrous methylene chloride solution 10mL by L-Phe methyl ester hydrochloride, is cooled to 0 ℃, adds triethylamine, then adds p-phthaloyl chloride 5mL, obtains reaction soln; Reaction soln is slowly risen to room temperature and stir 12 hours;
Step 3, rotary evaporation reaction solution, adds deionized water 10mL, filters collecting precipitation;
Step 4, ethanol 5mL recrystallization for gained precipitation, filters and be dried 10 hours in baking oven, and 50 ℃ to 60 ℃ of drying temperatures, obtain product Isosorbide-5-Nitrae-phenyl phenylalanine methyl ester;
Step 5, to 1, in the methanol solution of 4-phenyl phenylalanine methyl ester, add 2M sodium hydroxide solution, reaction mixture is stirring reaction 20～24 hours at room temperature, with 3M hydrochloric acid soln, reacting liquid pH value is adjusted to and is less than 3, filter and collect generate precipitation vacuum-drying, obtain dye sorbent Isosorbide-5-Nitrae-phenyl phenylalanine;
Step 6, by Isosorbide-5-Nitrae-phenyl phenylalanine and glycol ether generation acid-catalyzed esterification reaction, obtains final product chirality supramolecular hydrogel, and as shown in Figure 5, wherein, a is right-handed helix to the fibre shape figure of described supramolecular hydrogel, and b is left hand helix.
embodiment 4
The present embodiment relates to a kind of chirality supramolecular hydrogel, and described chirality supramolecular hydrogel is that Isosorbide-5-Nitrae-phenyl ring is the phenylalanine derivative of core, and the structural formula of described derivative is as follows:
Wherein, R
1for COOEtOEtOH,
R
2for H.
The present embodiment also relates to the preparation method of aforementioned chirality supramolecular hydrogel, and described method comprises:
Step 2, the anhydrous methylene chloride solution 10mL by L-Phe methyl ester hydrochloride, is cooled to 0 ℃, adds triethylamine, then adds p-phthaloyl chloride 5mL, obtains reaction soln; Reaction soln is slowly risen to room temperature and stir 12 hours;
Step 3, rotary evaporation reaction solution, adds deionized water 20mL, filters collecting precipitation;
Step 4, gained precipitation is 50% by ethanol 5mL(concentration) recrystallization, filter and be dried 10 hours in baking oven, 50 ℃ to 60 ℃ of drying temperatures, obtain product Isosorbide-5-Nitrae-phenyl phenylalanine methyl ester;
Step 5, to 1, in the methanol solution of 4-phenyl phenylalanine methyl ester, add 1M sodium hydroxide solution, reaction mixture is stirring reaction 20～24 hours at room temperature, with 2M hydrochloric acid soln, reacting liquid pH value is adjusted to and is less than 3, filter and collect generate precipitation vacuum-drying, obtain dye sorbent Isosorbide-5-Nitrae-phenyl phenylalanine;
Step 6, by Isosorbide-5-Nitrae-phenyl phenylalanine and glycol ether generation acid-catalyzed esterification reaction, obtains final product chirality supramolecular hydrogel, and as shown in Figure 5, wherein, a is right-handed helix to the fibre shape figure of described supramolecular hydrogel, and b is left hand helix.
The supramolecular hydrogel that the present embodiment 1～4 makes adds complete cell culture fluid fore-and-aft stability photo comparison diagram, as shown in Figure 1: (a, d is 0 minute; B, after e is 30 minutes; C, after f is 20 days); The spectrogram of the supramolecular hydrogel that embodiment 1～4 makes is shown in successively in Fig. 4 and schemes shown in (4A), (4B), (4C), (4D).
L-type Isosorbide-5-Nitrae-phenyl phenylalanine
1h NMR (400MHz, DMSO-d
6, δ, ppm): δ=3.2 (d, 4H, CH
2), 4.6 (s, 2H, CH), 7.3 (q, 10H, Ar-H), 7.8 (s, 4H, Ar-H), 8.8 (d, 2H, NH), 12.8 (s, 2H, OH) .(D type Isosorbide-5-Nitrae-phenyl phenylalanine is same)
LPH:
1h NMR (400MHz, DMSO-d
6, δ, ppm): δ=3.06-3.19 (m, 4H, CH
2), 3.39-3.46 (m, 8H, CH
2), 3.52-3.59 (m, 4H, CH
2), 4.15-4.18 (m, 4H, CH
2), 4.53-4.58 (m, 2H, CH), 4.62-4.68 (m, 2H, OH), 7.16-7.19 (t, J=4.0,8.0Hz, 2H, Ar-H), 7.24-7.30 (m, 8H, Ar-H), 7.82 (s, 4H, Ar-H), 8.95-8.97 (d, J=8.0Hz, 2H, CO-NH) .(DPH with)
the purposes of embodiment 5, chirality supramolecular hydrogel
The 2.1 pairs of NIH3T3 cells are in the purposes of the controlled adhesion of the two-dimensional fiber film surface of chirality supramolecular hydrogel
It is gel chirality supramolecular hydrogel prepared by previous embodiment 1-4 that the present embodiment adopts chirality supramolecular hydrogel
First 6.0mg Gelatin powder is dissolved in and in 3.0mL deionized water, makes 3.0mL hydrogel (2.0mg/mL), in 96 porocyte culture plates, every hole adds 100uL hydrogel, vacuum-drying 12h at 35 ℃, UV-irradiation 30min, by NIH3T3 cell trysinization 2-3min, centrifugal, remove Digestive system, 1 * PBS rinses, then adds complete culture solution piping and druming cell, form even cell suspension, NIH3T3 cell density is adjusted to 5.0 * 10
4/ mL, every hole adds 100 μ L NIH3T3 cell suspensions, is placed in 37 ℃, 5%CO
2in cell culture incubator, hatch the adhesion situation of observation of cell after 4h.NIH3T3 cell adhesion process is shown in Fig. 2 a, b, and cell adhesion amount has improved 2 times at L-type material surface than D type.
The 2.2 pairs of HUVEC cells are in the purposes of the controlled adhesion of the two-dimensional fiber film surface of chirality supramolecular hydrogel
The 3.0mL hydrogel (2.0mg/mL) of preparing as aforementioned 2.1 steps, in 96 porocyte culture plates, every hole adds 100uL hydrogel, vacuum-drying 12h at 35 ℃, UV-irradiation 30min, by HUVEC cell trysinization 2-3min, centrifugal, remove Digestive system, 1 * PBS rinses, then adds complete culture solution piping and druming cell, form even cell suspension, HUVEC cell density is adjusted to 1.0 * 10
5/ mL, every hole adds 100uL cell suspension, is placed in 37 ℃, 5%CO
2in cell culture incubator, hatch the adhesion situation of observation of cell after 4h.HUVEC cell adhesion process is shown in Fig. 2 c, d, and HUVEC cell adhesion amount has improved 2 times at L-type material surface than D type.
The 2.3 pairs of NIH3T3 cells are in the purposes of the controlled adhesion of the three-dimensional microenvironment of chirality supramolecular hydrogel
First 80mg gelator powder is dissolved in to 1.0mL biological with making 1.0mL solution (80mg/mL) in methyl-sulphoxide (DMSO), by NIH3T3 cell trysinization 2-3min, centrifugal, remove Digestive system, 1 * PBS rinses, add again complete culture solution piping and druming cell, form even cell suspension, NIH3T3 cell density is adjusted to 1.0 * 10
7/ mL, get NIH3T3 cell and gel mixture (gel strength is 2.0mg/mL) that the NIH3T3 cell suspension of 4.0mL and the DMSO solution (80mg/mL) of 0.1mL gelator are before mixed to get about 4.0mL, in 24 orifice plates, every hole adds 500uL cell and gel mixture, is placed in 37 ℃, 5%CO
2in cell culture incubator, hatch after 30min, every hole adds 1.0mL cell complete culture solution, is placed in 37 ℃, 5%CO
2in cell culture incubator, hatch the adhesion situation of observation of cell after 24h.NIH3T3 cell adhesion process is shown in Fig. 3 a, b, and NIH3T3 cell adhesion amount has improved more than 2 times than D type in L-type material, and has occurred cell proliferation earlier having occurred cell cluster.
The 2.4 pairs of HUVEC cells are in the purposes of the controlled adhesion of the three-dimensional microenvironment of chirality supramolecular hydrogel
As aforementioned 2.3 steps are prepared the DMSO solution (80mg/mL) of 1.0mL hydrogel, by HUVEC cell trysinization 2-3min, centrifugal, remove Digestive system, 1 * PBS rinses, then adds complete culture solution piping and druming cell, form even cell suspension, cell density is adjusted to 1.0 * 10
7/ mL, get HUVEC cell and gel mixture (gel strength is 2.0mg/mL) that the HUVEC cell suspension of 4mL and the DMSO solution (80mg/mL) of 0.1mL gelator are before mixed to get 4.0mL, in 24 orifice plates, every hole adds 500uL cell and gel mixture, is placed in 37 ℃, 5%CO
2in cell culture incubator, hatch after 30min, every hole adds 1.0mL cell complete culture solution, is placed in 37 ℃, 5%CO
2in cell culture incubator, hatch the adhesion situation of observation of cell after 24h.Cell adhesion process is shown in Fig. 3 c, d, and HUVEC cell adhesion amount has improved more than 2 times than D type in L-type material, and has occurred cell proliferation earlier having occurred cell cluster.
In sum, the chirality supramolecular hydrogel that this enforcement makes can be used for cytoskeleton material, is the biomimetic cell scaffolds material with the selective attachment of the chirality regulating cell by nanofiber; The selective attachment process of chirality supramolecular hydrogel regulating cell is carried out under physiological environment, easy to operate, there is actual application value, the preparation method of super chirality supramolecular hydrogel is without complicated synthesis step, be easy to industrial production in enormous quantities, products therefrom purity is high, and good dispersity is suitable for commercialization and uses for cell cultures and controlled adhesive agent.
Above specific embodiments of the invention are described.It will be appreciated that, the present invention is not limited to above-mentioned specific implementations, and those skilled in the art can make various distortion or modification within the scope of the claims, and this does not affect flesh and blood of the present invention.
Claims (10)
1. a chirality supramolecular hydrogel, is characterized in that, described chirality supramolecular hydrogel is that Isosorbide-5-Nitrae-phenyl ring is the phenylalanine derivative of core, and the structural formula of described derivative is as follows:
Wherein, R
1for H or COOEtOEtOH,
R
2for H or COOEtOEtOH.
2. a preparation method for chirality supramolecular hydrogel as claimed in claim 1, is characterized in that, described method comprises the steps:
Step 1, gets p-phthaloyl chloride, L-Phe methyl ester hydrochloride, triethylamine;
Step 2, the anhydrous methylene chloride solution of L-Phe methyl ester hydrochloride is cooling, add successively triethylamine, p-phthaloyl chloride, obtain reaction soln, reaction soln is slowly risen to room temperature and stirs;
Step 3, rotary evaporation reaction soln, adds deionized water, filters collecting precipitation;
Step 4, by gained precipitation ethyl alcohol recrystallization, filters, dry, obtains product Isosorbide-5-Nitrae-phenyl phenylalanine methyl ester;
Step 5 adds sodium hydroxide solution in the methanol solution of Isosorbide-5-Nitrae-phenyl phenylalanine methyl ester, and stirring reaction under room temperature is adjusted to pH with hydrochloric acid soln and is less than 3, filters, and collects generate precipitation vacuum-drying, obtains Isosorbide-5-Nitrae-phenyl phenylalanine;
Step 6, by Isosorbide-5-Nitrae-phenyl phenylalanine and glycol ether generation acid catalysis generation esterification, obtains final product chirality supramolecular hydrogel.
3. the preparation method of chirality supramolecular hydrogel as claimed in claim 2, is characterized in that, in step 1, the mol ratio of described p-phthaloyl chloride, L-Phe methyl ester hydrochloride, triethylamine is 2:3:4～1:4:10.
4. the preparation method of chirality supramolecular hydrogel as claimed in claim 2, is characterized in that, in step 2, described cooling temperature is 0 ℃, and the time of described stirring is 12～16 hours.
5. the preparation method of chirality supramolecular hydrogel as claimed in claim 2, it is characterized in that, in step 2, the volumetric molar concentration of the anhydrous methylene chloride solution of described L-Phe methyl ester hydrochloride is 0.02～0.5mol/L, and the volumetric molar concentration of the anhydrous methylene chloride solution of described p-phthaloyl chloride is 0.05～0.5mol/L.
6. the preparation method of chirality supramolecular hydrogel as claimed in claim 2, is characterized in that, in step 3, the consumption of described deionized water is 10～20mL.
7. the preparation method of chirality supramolecular hydrogel as claimed in claim 2, is characterized in that, in step 4, and the concentration 50～95% of described ethanol, dry temperature is 50～95 ℃, the time is 3～24h.
8. the preparation method of chirality supramolecular hydrogel as claimed in claim 2, is characterized in that, in step 5, described sodium hydroxide solution is 1～3M, and described hydrochloric acid soln is 2～6M, and described churning time is 20～24 hours.
9. the preparation method of chirality supramolecular hydrogel as claimed in claim 2, is characterized in that, in step 6, the mass ratio of described Isosorbide-5-Nitrae-phenyl phenylalanine and glycol ether generation esterification is 1:1～1:10.
10. a purposes for chirality supramolecular hydrogel as claimed in claim 1, is characterized in that, described chirality supramolecular hydrogel can be used for cytoskeleton material.
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|---|---|---|---|---|
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61197520A (en) * | 1985-02-27 | 1986-09-01 | Japan Synthetic Rubber Co Ltd | Infusion liquid for ophthalmic use |
| CN102585267A (en) * | 2012-02-23 | 2012-07-18 | 上海交通大学 | Intelligent gel three-dimensional scaffold material for cell culture |
| CN102698667A (en) * | 2012-06-19 | 2012-10-03 | 重庆大学 | Spherical pore foaming agent with nuclear shell structure and three-dimensional cytoskeleton prepared by same |
-
2013
- 2013-12-06 CN CN201310658697.7A patent/CN103694131A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61197520A (en) * | 1985-02-27 | 1986-09-01 | Japan Synthetic Rubber Co Ltd | Infusion liquid for ophthalmic use |
| CN102585267A (en) * | 2012-02-23 | 2012-07-18 | 上海交通大学 | Intelligent gel three-dimensional scaffold material for cell culture |
| CN102698667A (en) * | 2012-06-19 | 2012-10-03 | 重庆大学 | Spherical pore foaming agent with nuclear shell structure and three-dimensional cytoskeleton prepared by same |
Non-Patent Citations (2)
| Title |
|---|
| CHUAN-LIANG FENG等: "C2-symmetric benzene-based hydrogels with unique layered structures for controllable organic dye adsorption", 《SOFT MATTER》 * |
| CHUAN-LIANG FENG等: "Mechanical reinforcement of C2-phenyl-derived hydrogels for controlled cell adhesion", 《SOFT MATTER》 * |
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Application publication date: 20140402 |