CN109876194A - A kind of POSS-PEG hybridized hydrogel of adjustable degradation rate and preparation method thereof and its application - Google Patents
A kind of POSS-PEG hybridized hydrogel of adjustable degradation rate and preparation method thereof and its application Download PDFInfo
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- 230000015556 catabolic process Effects 0.000 title claims abstract description 30
- 238000002360 preparation method Methods 0.000 title claims abstract description 24
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 17
- 238000006845 Michael addition reaction Methods 0.000 claims abstract description 6
- 239000000872 buffer Substances 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims abstract description 6
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- 239000000463 material Substances 0.000 claims description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- 238000004132 cross linking Methods 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 abstract description 4
- 230000003000 nontoxic effect Effects 0.000 abstract description 4
- 239000004033 plastic Substances 0.000 abstract description 3
- 229920003023 plastic Polymers 0.000 abstract description 3
- 230000008901 benefit Effects 0.000 abstract description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 39
- 210000004027 cell Anatomy 0.000 description 31
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- 239000001963 growth medium Substances 0.000 description 8
- 210000004271 bone marrow stromal cell Anatomy 0.000 description 6
- 230000004072 osteoblast differentiation Effects 0.000 description 6
- 230000001965 increasing effect Effects 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 3
- RGCKGOZRHPZPFP-UHFFFAOYSA-N alizarin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
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- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- -1 Poly(ethylene glycol) Polymers 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
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Abstract
The present invention relates to POSS-PEG hybridized hydrogels of a kind of adjustable degradation rate and preparation method thereof and its application, should be the preparation method comprises the following steps: 4-arm-PEG-MAL and POSS-SH are passed through Michael addition reaction in organic solvent is made POSS-PEG prepolymer；POSS-PEG prepolymer and crosslinking agent are dissolved in buffer and obtain pre- gelling solution, pre- gelling solution is passed through into the POSS-PEG hybridized hydrogel that a kind of adjustable degradation rate is made in Michael addition reaction at the reaction temperatures；Wherein, crosslinking agent is mixed to form by PEG-dithiol and PEG-diester-dithiol in pre- gelling solution.POSS-PEG hybridized hydrogel provided by the invention has the advantages that uniform hole configurations, good biocompatibility, plastic are fast, mechanical property is good, nontoxic.
Description
Technical field
The present invention relates to hydrogel polymeric material field more particularly to a kind of POSS-PEG of adjustable degradation rate are miscellaneous
Change hydrogel and preparation method thereof and its application.
Background technique
3D bracket plays a crucial role in organizational project and 3D cell culture application.It is fast with organizational project
Speed development, 3D bracket has great application potential in various biomedicines, therefore the requirement to it is also higher and higher.In order to lure
Guided cell adherency, is proliferated and activates growth and differentiation to instruct specific cells, and the material for being used to prepare bracket must have life
Object compatibility, suitable degradation rate, porosity, mechanical stability appropriate and chemical induction appropriate are to divide cell
Sub- bio-identification.
Timbering material as 3D cell culture needs the biocompatibility and mechanical strength of a period of time, and finally answers
With required degradation rate degradation in vivo, while avoiding any immune response.Poly(ethylene glycol) (PEG) hydrogel is a group weaver
For one of cell encapsulating and the widest timbering material transplanted in journey, there is excellent biocompatibility, hydrophily is non-to exempt from
Epidemic focus and anti-protein absorption.In addition, their biological degradability is another important feature.The biology drop of PEG hydrogel
Solution property can hydrolyze by enzymatic or environment approach is realized such as incorporation degradable components.In addition, passing through the molecule for changing PEG
Amount and concentration, can improve the mechanical performance of PEG hydrogel.
Polyhedral oligomeric silsesquioxane (POSS) have cube cage type nanostructure, molecular dimension between 1-3nm, by
The organic-inorganic nano hybrid structure of the inorganic skeleton of the Si-O-Si key composition of core and external organic substituent composition, has
Good biocompatibility, special surface property and high-mechanical property.Monofunctional typical case's POSS molecule is introduced into PEG water
On gel, a small amount of POSS can cause the significant changes of hydrogel properties.Its POSS-PEG hybridized hydrogel prepared, no
It is only capable of the mechanical property of enhancing hydrogel, can more delay the degradation rate of certain time, but above-mentioned degradation rate is fixed and can not
It adjusts, a variety of needs using scene can not be adapted to.
Summary of the invention
For the above problem existing for hydrogel, a kind of POSS-PEG hybridized hydrogel of adjustable degradation rate is now provided
And preparation method thereof and its application, it is desirable to provide a kind of good biocompatibility, plastic is fast, mechanical property is good nontoxic and with adjustable
Control the hydrogel material of degradation rate.
Specific technical solution is as follows:
The first aspect of the invention is to provide a kind of preparation of the POSS-PEG hybridized hydrogel of adjustable degradation rate
Method has such speciality, includes the following steps: in organic solvent to pass through 4-arm-PEG-MAL and POSS-SH
POSS-PEG prepolymer is made in Michael addition reaction；POSS-PEG prepolymer is dissolved in buffer with crosslinking agent and is obtained
Pre- gelling solution is passed through Michael addition reaction at the reaction temperatures and a kind of adjustable degradation rate is made by pre- gelling solution
POSS-PEG hybridized hydrogel；Wherein, crosslinking agent is mixed by PEG-dithiol and PEG-diester-dithiol in step 2
It closes and is formed.
Above-mentioned preparation method, also has the feature that, organic solvent be selected from tetrahydrofuran, methylene chloride, methanol or
One of acetone.
Above-mentioned preparation method, also has the feature that, function base-MAL and function base-SH in 4-arm-PEG-MAL
The molar ratio of (total-SH number in crosslinking agent) is 1:1-1.5.
Above-mentioned preparation method, also has the feature that, buffer TEA.
Above-mentioned preparation method, also has the feature that, the pH=7.4 of TEA, and its concentration is 4mM.
Above-mentioned preparation method, also has the feature that, reaction temperature is 25-40 DEG C, crosslinking time 0-30min.
Above-mentioned preparation method, also has the feature that, the mass percent of crosslinking agent is 25- in hybridized hydrogel
100%.
4-arm-PEG-MAL (four dendritic dimaleoyl imino functional polyethylene glycols) is commercial product (north in the present invention
Jing Jiankai Science and Technology Ltd. provides), it is preferred that select average molecular weight for the 4-arm-PEG- of 5-20kDa in the present invention
MAL。
POSS-SH (single angle sulfydryl polyhedral oligomeric silsesquioxane) is that (Sigma company mentions for commercial product in the present invention
For), No. CAS is 480438-85-5.
PEG-dithiol (two mercaptan of polyethylene glycol) is that (Beijing Jian Kai Science and Technology Ltd. mentions for commercial product in the present invention
For), it is preferred that select average molecular weight for the PEG-dithiol of 2-4kDa in the present invention.
PEG-diester-dithiol (two mercaptan of polyethylene glycol di) is the autonomous sintetics in laboratory in the present invention
(bibliography: Zustiak S.P., Leach J.B.Hydrolytically degradable poly (ethylene
glycol)hydrogel caffolds with tunable degradation and mechanical properties
[J] .Biomacromolecules, 2010,11:1348-135), characterized through all kinds of means of testing, PEG- in the present invention
The average molecular weight of diester-dithiol is 2-4kDa.
The second aspect of the invention is to provide a kind of adjustable degradation rate prepared using above-mentioned preparation method
POSS-PEG hybridized hydrogel.
The third aspect of the invention is to provide a kind of POSS-PEG hybridized hydrogel of above-mentioned adjustable degradation rate
Using having the feature that, as organizational project 3D timbering material.
The beneficial effect of above scheme is:
1), POSS-PEG hybridized hydrogel provided by the invention has that hole configurations is uniform, good biocompatibility, plastic
Fastly, good, the nontoxic advantage of mechanical property；
2), POSS-PEG hybridized hydrogel provided by the invention can be prolonged by adjusting the degradation rate of hybridized hydrogel
Long degradation cycle.
Detailed description of the invention
Fig. 1 is the sem test figure of the POSS-PEG hybridized hydrogel provided in the embodiment of the present invention；
Fig. 2 is the degradation rate line chart (2A) and column of the POSS-PEG hybridized hydrogel provided in the embodiment of the present invention
Shape figure (2B)；
Fig. 3 is the sem test figure after the POSS-PEG hybridized hydrogel degradation provided in the embodiment of the present invention；
Fig. 4 is the Cell culture invitro dead cell dye living of the POSS-PEG hybridized hydrogel provided in the embodiment of the present invention
Chromatic graph；
Fig. 5 is the HUVEC cell morphology figure of the POSS-PEG hybridized hydrogel 3D culture provided in the embodiment of the present invention；
Fig. 6 is living using the BMSCs of the POSS-PEG hybridized hydrogel progress 3D culture provided in the embodiment of the present invention
Dead cell stain fluorescence microscope test chart；
Fig. 7 is that the BMSCs Osteoblast Differentiation of the POSS-PEG hybridized hydrogel 3D culture provided in the embodiment of the present invention is alizarin
Plain red colouring test chart.
Specific embodiment
Following will be combined with the drawings in the embodiments of the present invention, and technical solution in the embodiment of the present invention carries out clear, complete
Site preparation description, it is clear that described embodiments are only a part of the embodiments of the present invention, instead of all the embodiments.It is based on
Embodiment in the present invention, those of ordinary skill in the art without creative labor it is obtained it is all its
His embodiment, shall fall within the protection scope of the present invention.
It should be noted that in the absence of conflict, the feature in embodiment and embodiment in the present invention can phase
Mutually combination.
The present invention will be further explained below with reference to the attached drawings and specific examples, but not as the limitation of the invention.
A kind of POSS-PEG hybridized hydrogel of adjustable degradation rate, preparation method includes the following steps: will be commercially available
4-arm-PEG-MAL and POSS-SH be dissolved in tetrahydrofuran, be stirred at room temperature reaction a period of time back spin tetrahydro furan is evaporated off
It mutters, obtains POSS-PEG prepolymer；Then by POSS-PEG prepolymer and crosslinking agent (by PEG-dithiol and PEG-
Diester-dithiol is mixed to form, and wherein the molar ratio of function base-MAL and function base-SH is 1:1-1.5) it is dissolved in pH=
It in 7.4 4mM Triethanolamine buffer, is uniformly mixed them adequately, obtains pre- gelling solution；Finally by pre- gelling solution
It is transferred in 500 μ L molds, is reacted in 15min in 37 DEG C of biochemical cultivation cases, obtain a kind of POSS-PEG of adjustable degradation rate
Hybridized hydrogel (mass percent of crosslinking agent is 25-100% in hybridized hydrogel).
Each parameter is as shown in the table in the embodiment of the present invention 1-3 and comparative example:
Scanning electron microscope as shown in Figure 1, POSS-PEG hybridized hydrogel provided by the invention is in porous spongy structure, and
Its uniform pore diameter is unified, and average pore size has biggish porosity between 20~40nm.
Degradation rate test
POSS-PEG hybridized hydrogel is freeze-dried, its weight of precise, then dry hydrogel is added
The phosphate buffer (PBS, PH=7.4,10mL) of 0.01M, is placed in 37 DEG C of constant temperature biochemical cultivation cases, and distilled water floats after 4 weeks
It washes, is freeze-dried, weighing calculates accumulation degradation percentage (%)=(the preceding hydrogel weight of degrading of every group of hydrogel in the solution
Hydrogel quality after amount-degradation)/preceding hydrogel weight × 100% of degrading, in order to ensure testing accuracy, every group of hydrogel takes 3
A test specimens, three test specimens are averaged.
As shown in Figure 2, POSS-PEG hybridized hydrogel provided by the invention is with PEG-diester- in crosslinking agent
Dithiol content gradually increases, and the mass loss of hydrogel also becomes larger, and when being degraded to the 4th week, provides in embodiment 3
Hydrogel be not able to maintain gel form, mass loss weighing and calculating can not be carried out.
As shown in Figure 3, with gradually increasing for PEG-diester-dithiol content in crosslinking agent and prolonging for degradation time
Long, originally clear uniform hole configurations gradually collapses in POSS-PEG hybridized hydrogel provided by the invention, to after 4th week,
The hydrogel three-dimensional structure provided in embodiment 3 is substantially completely destroyed.Cell culture experiments in vitro
It is uniformly mixed with Human umbilical vein endothelial's cell (HUVEC) by POSS-PEG hybridized hydrogel in advance at each 1.2mL of glue
It closes, cell density is 1 × 106/ mL takes 100 μ L to be placed in 96 porocyte culture plates, 5%CO respectively2Constant incubator 37
DEG C be incubated for 30min, be added 200 μ L contain 10% fetal calf serum low sugar DMEM culture medium, continue to be incubated for, respectively at the 1st, 4,7 day
Interior taking-up sample carries out dead cell stain test cell activity living, using fluorescence microscopy image, observe cell activity and
Form.
As shown in Figure 4, cell can be in hybridized hydrogel enclosed inside provided by the invention, and with the increasing of incubation time
Add, cell viability gradually increases, and shows that cell can survive in the hydrogel material, and it is good to illustrate that such hydrogel has
Biocompatibility and nontoxic；And with the increase of PEG-diester-dithiol content in crosslinking agent, cell number has higher
Cell proliferation speed.
As shown in Figure 5, cell can in hybridized hydrogel provided by the invention well-grown, and encapsulate cell growing
Cellular morphology has differences in the process；Meanwhile with the increase of PEG-diester-dithiol content in crosslinking agent, cell shape
State gradually becomes round from slender spindle, when PEG-diester-dithiol content reaches 100%, the shape of the cell of encapsulating
State is that full and circular (this is related with the size of cell growing space in hydrogel degradation process, PEG-diester-
Dithiol content is higher, and cell growing space is bigger, and cell is rounded；On the contrary, cell is the elongated spindle bodily form).It is living dead thin
Born of the same parents dye test
POSS-PEG hybridized hydrogel is made in advance at each 1.2mL of glue, it is uniform with mesenchymal stem cell (BMSCs)
Mixing, cell density are 1 × 106/ mL takes 100 μ L to be placed in 96 porocyte culture plates, 5%CO respectively2Constant incubator
37 DEG C of incubation 30min are added the low sugar DMEM culture medium that 200 μ L contain 10% fetal calf serum, continue to be incubated for, when cell is grown to about
When 80%, Osteoblast Differentiation culture medium is used to cultivate, in the 14th day taking-up sample, it is living to carry out dead cell stain test cell living
Property, meanwhile, further to confirm cell Osteoblast Differentiation in Osteoblast Differentiation culture medium, PEG-diester- will be encapsulated in
The BMSCs in hybridized hydrogel that dithiol content is 100% is cultivated in growth medium simultaneously to be used to compare, and
After being grown 14 days in Osteoblast Differentiation culture medium, culture medium is sucked out and is washed twice with PBS, then by 4% poly of frozen section
Formaldehyde fixes 20 minutes, is washed three times with PBS, then by measuring doped calcium with alizarin red dyeing.
As shown in Figure 6, with the increase of PEG-diester-dithiol content in crosslinking agent, cell number is gradually increased, when
When PEG-diester-dithiol content reaches 100% in crosslinking agent, cell reaches maximum value, this further demonstrates that BMSCs
It can also be grown well in these mixing hydrogels.
As shown in Figure 7, with the increase of PEG-diester-dithiol content in crosslinking agent, Osteoblast Differentiation is gradually increased,
Calcium tubercle increases, and the cell calcium tubercle in growth medium is less, this illustrates that BMSCs can be in water-setting glue material provided by the invention
Breeding differentiation is carried out in material, this also further confirms to illustrate that such hydrogel material can be used as organizational project 3D bracket.
The foregoing is merely preferred embodiments of the present invention, are not intended to limit embodiments of the present invention and protection model
It encloses, to those skilled in the art, should can appreciate that all with made by description of the invention and diagramatic content
Equivalent replacement and obviously change obtained scheme, should all be included within the scope of the present invention.
Claims (9)
1. a kind of preparation method of the POSS-PEG hybridized hydrogel of adjustable degradation rate, which is characterized in that including walking as follows
It is rapid: 4-arm-PEG-MAL and POSS-SH to be passed through into Michael addition reaction in organic solvent, POSS-PEG prepolymer is made；
POSS-PEG prepolymer and crosslinking agent are dissolved in buffer and obtain pre- gelling solution, at the reaction temperatures by pre- gelling solution
A kind of POSS-PEG hybridized hydrogel of adjustable degradation rate is made by Michael addition reaction；Wherein, it is handed in step 2
Connection agent is mixed to form by PEG-dithiol and PEG-diester-dithiol.
2. preparation method according to claim 1, which is characterized in that organic solvent is selected from tetrahydrofuran, methylene chloride, first
One of alcohol or acetone.
3. preparation method according to claim 1, which is characterized in that function base-MAL and crosslinking in 4-arm-PEG-MAL
The molar ratio of function base-SH is 1:1-1.5 in agent.
4. preparation method according to claim 1, which is characterized in that buffer TEA.
5. preparation method according to claim 1, which is characterized in that the pH=7.4 of TEA, and its concentration is 4mM.
6. preparation method according to claim 1, which is characterized in that reaction temperature is 25-40 DEG C, crosslinking time 0-
30min。
7. preparation method according to claim 3, which is characterized in that the mass percent of crosslinking agent is in hybridized hydrogel
25-100%.
8. a kind of POSS-PEG hybridized hydrogel of adjustable degradation rate, which is characterized in that -7 any one according to claim 1
The preparation method obtains.
9. a kind of application of the POSS-PEG hybridized hydrogel of adjustable degradation rate, which is characterized in that as organizational project 3D
Timbering material.
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