CN101591818A - Shikonin PCL/PTMC composite nano fiber and preparation and application - Google Patents
Shikonin PCL/PTMC composite nano fiber and preparation and application Download PDFInfo
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- CN101591818A CN101591818A CNA2009100473502A CN200910047350A CN101591818A CN 101591818 A CN101591818 A CN 101591818A CN A2009100473502 A CNA2009100473502 A CN A2009100473502A CN 200910047350 A CN200910047350 A CN 200910047350A CN 101591818 A CN101591818 A CN 101591818A
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- NEZONWMXZKDMKF-JTQLQIEISA-N Alkannin Chemical compound C1=CC(O)=C2C(=O)C([C@@H](O)CC=C(C)C)=CC(=O)C2=C1O NEZONWMXZKDMKF-JTQLQIEISA-N 0.000 title claims abstract description 91
- UNNKKUDWEASWDN-UHFFFAOYSA-N alkannin Natural products CC(=CCC(O)c1cc(O)c2C(=O)C=CC(=O)c2c1O)C UNNKKUDWEASWDN-UHFFFAOYSA-N 0.000 title claims abstract description 91
- 239000002131 composite material Substances 0.000 title claims abstract description 41
- 239000002121 nanofiber Substances 0.000 title claims abstract description 41
- 241001071917 Lithospermum Species 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims abstract description 20
- 229920001610 polycaprolactone Polymers 0.000 claims abstract description 71
- 239000004229 Alkannin Substances 0.000 claims abstract description 70
- 235000019232 alkannin Nutrition 0.000 claims abstract description 70
- 239000003814 drug Substances 0.000 claims abstract description 17
- 239000000463 material Substances 0.000 claims abstract description 10
- 239000012046 mixed solvent Substances 0.000 claims abstract description 10
- 239000011259 mixed solution Substances 0.000 claims abstract description 6
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 3
- 238000013270 controlled release Methods 0.000 claims abstract description 3
- 238000010041 electrostatic spinning Methods 0.000 claims abstract description 3
- 229920002521 macromolecule Polymers 0.000 claims abstract description 3
- 230000002459 sustained effect Effects 0.000 claims abstract description 3
- 238000013268 sustained release Methods 0.000 claims abstract description 3
- 230000001225 therapeutic effect Effects 0.000 claims abstract description 3
- 230000000699 topical effect Effects 0.000 claims abstract description 3
- 239000000243 solution Substances 0.000 claims description 11
- 239000000284 extract Substances 0.000 claims description 9
- 235000004256 Buglossoides arvense Nutrition 0.000 claims description 7
- 241000118841 Lithospermum incisum Species 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 2
- 238000004440 column chromatography Methods 0.000 claims description 2
- 235000012054 meals Nutrition 0.000 claims description 2
- 238000012856 packing Methods 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 238000000638 solvent extraction Methods 0.000 claims description 2
- 239000000835 fiber Substances 0.000 abstract description 12
- 229940079593 drug Drugs 0.000 abstract description 10
- 230000000694 effects Effects 0.000 abstract description 9
- 230000008901 benefit Effects 0.000 abstract description 3
- 231100000331 toxic Toxicity 0.000 abstract description 3
- 230000002588 toxic effect Effects 0.000 abstract description 3
- 239000002657 fibrous material Substances 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000005303 weighing Methods 0.000 description 7
- 238000001523 electrospinning Methods 0.000 description 6
- 238000009987 spinning Methods 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 230000000844 anti-bacterial effect Effects 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 241000588724 Escherichia coli Species 0.000 description 4
- 238000002835 absorbance Methods 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- -1 DPPH free radical Chemical class 0.000 description 3
- 241000191967 Staphylococcus aureus Species 0.000 description 3
- 239000012456 homogeneous solution Substances 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 230000010355 oscillation Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 241001050829 Arnebia guttata Species 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000007760 free radical scavenging Effects 0.000 description 2
- 238000013507 mapping Methods 0.000 description 2
- 241000130784 Arnebia euchroma Species 0.000 description 1
- 241001072256 Boraginaceae Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 229930192627 Naphthoquinone Natural products 0.000 description 1
- 206010052428 Wound Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012738 dissolution medium Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- HHEAADYXPMHMCT-UHFFFAOYSA-N dpph Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1[N]N(C=1C=CC=CC=1)C1=CC=CC=C1 HHEAADYXPMHMCT-UHFFFAOYSA-N 0.000 description 1
- 239000002158 endotoxin Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 229920006008 lipopolysaccharide Polymers 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 239000007962 solid dispersion Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
- 208000013464 vaginal disease Diseases 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
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- Medicinal Preparation (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The present invention relates to a kind of shikonin PCL/PTMC composite nano fiber, its component comprises: alkannin, poly-epsilon-caprolactone PCL and PTMC PTMC, and wherein, alkannin is 0.001～50: 100 with PCL/PTMC high molecule mass ratio; Its preparation comprises: with alkannin, PCL and PTMC dissolving and carrene/N jointly in proportion, in the mixed solvent of dinethylformamide, preparation contains the carrier macromolecule mixed solution of alkannin; Mixed solution is carried out electrostatic spinning, promptly; This fiber applications is coated in medicine sustained and controlled release system, wound, the preparation of tumor post-operation topical therapeutic and biomedicine field.But its drug loading flexible modulation of fibrous material of the present invention adopts PCL and PTMC Biodegradable material, can not produce toxic and side effect; And the preparation method is simple and easy to do, and equipment is not had specific (special) requirements, has good economic benefit.
Description
Technical field
The invention belongs to PCL/PTMC composite nano fiber and preparation thereof and Application Areas, particularly relate to a kind of shikonin PCL/PTMC composite nano fiber and preparation and application.
Background technology
Alkannin (shikonin) is Boraginaceae (boraginacese) plant: as a kind of naphthoquinones active component in lithospermum euchromum Royle (Arnebia euchroma (Royle) Johnst), arnebia guttata Bunge (Arnebia guttata Bunge), the Asian puccoon dry roots such as (Lithospermum erythrorhizon Sieb.et Zucc.), and its chemical constitution See Figure:
That in recent years pharmacological testing proof alkannin has is antibiotic, anti-inflammatory, anti-oxidant, anticancer, promote multiple biologically active such as wound healing, it also has stable dyeability in addition, thereby obtains extensive concern in medicine, foods and cosmetics field.Along with the extensive use of new technology, new auxiliary material, some medical scholars do a lot of work at aspects such as alkannin dosage form research and improvement as problem.The beautiful grade of Pang show [Chinese patent drug .2001,23 (1): 5] has prepared the solid dispersion of Asian puccoon medicinal extract, has effectively improved the dissolution in vitro of Asian puccoon active ingredient, and then improves bioavilability in its body.Then, they have also prepared the Asian puccoon vagina effervescence, so that the treatment of vaginal disease more convenient effectively [Chinese patent drug .2004,26 (3): 181].Assimopoulou etc. [J Microcapsulation.2004,2:161] have prepared the microcapsule formulation that contains alkannin, thereby have improved its hydrophobicity and made it have slow release effect.
Electrospinning fibre is original owing to it at present, as has very big specific area, superior mechanical performance etc., and become a kind of ideal carrier of adorning the envelope medicine, obtaining many progress and achievement aspect the loading of effectively realizing medicine and the release.And utilize electrospinning, and the Asian puccoon white, quiet clothes are encapsulated in poly-epsilon-caprolactone (PCL) and PTMC (PTMC), about nanofiber and the preparation and the application of this composite, yet there are no relevant report.
Summary of the invention
Technical problem to be solved by this invention provides a kind of shikonin PCL/PTMC composite nano fiber and preparation and application, but its drug loading flexible modulation of this fibrous material adopts PCL and PTMC Biodegradable material, can not produce toxic and side effect; And the preparation method is simple and easy to do, and equipment is not had specific (special) requirements, has good economic benefit.
A kind of shikonin PCL of the present invention/PTMC composite nano fiber, its component comprises: alkannin, poly-epsilon-caprolactone (PCL) and PTMC (PTMC), wherein alkannin is 0.001～50: 100 with PCL/PTMC high molecule mass ratio, and the mass ratio of PCL and PTMC is 1: 100～100: 1;
The mass ratio of described PCL and PTMC is 9: 1,7: 3 or 5: 5;
Described alkannin is 1% or 5% with PCL/PTMC high molecule mass ratio;
Described shikonin PCL/its diameter of PTMC composite nano fiber is 150～400nm;
Described alkannin extracts by the following method, and Asian puccoon medicinal material 1kg is ground into meal, the apparatus,Soxhlet's of in batches packing into adopts benzinum for extracting solvent extraction 3d, merges extract, extract is evaporated to medicinal extract, and it is carried out column chromatography for separation (as shown in Figure 7);
The preparation method of a kind of shikonin PCL of the present invention/PTMC composite nano fiber comprises:
(1) with alkannin, PCL and PTMC dissolving and carrene/N jointly according to the above ratio, in the mixed solvent of dinethylformamide, preparation contains the carrier macromolecule mixed solution of alkannin; Wherein, carrene and N, the volume ratio of dinethylformamide is 100: 0～40: 60, PCL/PTMC high molecule mass and carrene/N, the ratio of dinethylformamide mixed solvent is 8g: 100ml;
(2) above-mentioned mixed solution is carried out electrostatic spinning, the temperature that controls environment is 10-35 ℃, and the feeding rate of solution is 0.8mL/h, and voltage is 14kV, and screen needle gage 18cm promptly gets the PCL/PTMC composite nano fiber that is loaded with alkannin.
Carrene and N in the described step (1), the preferred volume ratio of dinethylformamide is 3: 1.
Shikonin PCL of the present invention/PTMC composite nano fiber can be applicable to the preparation of biomedicine fields such as medicine sustained and controlled release system, wound are coated, tumor post-operation topical therapeutic.
The PCL/PTMC composite nano-fiber material that is loaded with alkannin of the present invention, the carrying drug ratio that proves alkannin by experiment can reach more than 95%, its chemical constitution did not change after the 1H-NMR collection of illustrative plates showed alkannin process high pressure electrospinning, its release meets Higuchi and discharges model, can to a certain degree regulate drug release process by ratio between adjusting PCL and the PTMC, and having better anti-oxidant and antibacterial activity, fiber carrier PCL and PTMC are Biodegradable material, have no side effect.
Beneficial effect
(1) but its drug loading flexible modulation of shikonin PCL of the present invention/PTMC composite nano-fiber material adopts PCL and PTMC Biodegradable material, can not produce toxic and side effect;
(2) this preparation method is simple and easy to do, and equipment is not had specific (special) requirements, has good economic benefit.
Description of drawings
Fig. 1 is the PCL/PTMC composite nano fiber stereoscan photograph that is loaded with 5% alkannin;
Wherein, a.PCL/PTMC 9: 1 (w/w); B.PCL/PTMC 7: 3 (w/w); C.PCL/PTMC 5: 5 (w/w);
Fig. 2 is the 1H-NMR collection of illustrative plates of PCL/PTMC composite nano fiber;
Fig. 3 is the 1H-NMR collection of illustrative plates of alkannin nanofiber;
Fig. 4 is the 1H-NMR collection of illustrative plates that is loaded with the PCL/PTMC composite nano fiber of alkannin;
Fig. 5 is the alkannin release profiles;
Wherein, a. is loaded with 1% alkannin; B. be loaded with 5% alkannin; C.Mt/M ∞ is to t
0.5Mapping;
Fig. 6 is loaded with the PCL/PTMC composite nano fiber of alkannin and the removing free radical activity comparison diagram of alkannin monomer;
Fig. 7 is an alkannin extraction process flow chart.
The specific embodiment
Below in conjunction with specific embodiment, further set forth the present invention.Should be understood that these embodiment only to be used to the present invention is described and be not used in and limit the scope of the invention.Should be understood that in addition those skilled in the art can make various changes or modifications the present invention after the content of having read the present invention's instruction, these equivalent form of values fall within the application's appended claims institute restricted portion equally.
Take by weighing the 0.0407g alkannin, 0.5612g PCL and 0.2409g PTMC, make them be dissolved in 10mL carrene/N, dinethylformamide (3: 1, v/v) in the mixed solvent, sonic oscillation makes abundant dissolving, obtains concentration 8.0% (w/v), PCL/PTMC mass ratio 7: 3, alkannin and with respect to high molecular mass fraction be 5% homogeneous solution.
The solution that configures is poured in the 5mL syringe, adopted No. 8 syringe needles to make flat mouthful spinning head.The flow velocity of solution at the spinning nozzle place is 0.8mL/h, and the voltage that is applied is 14kV, and two die openings obtain being loaded with the PCL/PTMC7 of 5% alkannin from being 18cm: 3 composite nano fiber.It is carried out following test:
1. be loaded with the surface observation of the PCL/PTMC composite nano fiber of alkannin
Shikonin PCL/PTMC the composite nano fiber for preparing is carried out scanning electron microscopic observation, and as shown in Figure 2, composite nano fiber is smooth continuously, along with the PTMC ratio increases, fibre diameter descend to some extent and form more even.Alkannin all is wrapped in the composite high-molecular material, does not influence the shaping of fiber.
2. actual drug loading calculates
Take by weighing a certain amount of drug-loading fibre, make it be dissolved in 5mL carrene/N, dinethylformamide (3: 1, v/v) in the mixed solvent, drawing this solution of 0.5mL joins in the methyl alcohol of 4.5mL, the centrifuging and taking supernatant is surveyed absorbance in the 516nm place afterwards, and calculates the actual drug loading of alkannin in the fiber according to the calibration curve of alkannin.According to the actual drug loading that calculates drug-loading fibre all more than 95%.
3. alkannin study on the stability
Alkannin is through the high pressure of tens kilovolts of electrospinning processes, and its character, whether structure changes is necessary to understand.Respectively with PCL/PTMC, alkannin carries out 1H-NMR with the composite nano fiber that is loaded with alkannin to be analyzed, and the result is shown in Fig. 3,4,5, and the affiliated peak of alkannin, PCL and PTMC all appears among Fig. 5, though illustrate that alkannin has kept its chemical constitution through the electrospinning high-pressure process.
4. the release of alkannin
Take by weighing a certain amount of drug-loading fibre, place 20mL dissolution medium (PBS/ methyl alcohol/Tween 80 79: 20: 1, v/v/v), shaking bath is set and is measured 37 ℃ of temperature, and rotating speed 100rpm is in 0,0.5,1,3,5,8,11,24 and 48h sampling, survey absorbance at the 516nm place, calculate alkannin accumulative total burst size, as Fig. 6 a﹠amp; Shown in the b.Alkannin discharges comparatively rapid at preceding 3h, discharge gradually thereupon and reach plateau.And along with the increase of medicament contg, burst size also increases relatively.For further investigating the releasing mechanism of alkannin, will totally discharge mark Mt/M ∞ to t
0.5The mapping back finds that the release of alkannin divides three parts to meet Higuchi release model (seeing Fig. 6 c)
5. removing the DPPH free radical activity measures
Take by weighing a certain amount of drug-loading fibre, make it be dissolved in 5mL carrene/N, and dinethylformamide (3: 1, in mixed solvent v/v), draw this solution of 0.2mL and be added on 2.8mL DPPH (1 * 10
-4M) in the methanol solution, after fully mixing, the room temperature lucifuge leaves standstill 60min, and in the absorbance of 517nm mensuration mixed liquor, absorbance is low more, and then explanation removing DPPH free radical activity is strong more.Take by weighing with fiber in same amount the alkannin monomer in contrast, with the free radical scavenging activity of alkannin in the drug-loading fibre relatively.As shown in Figure 7, alkannin in the alkannin composite nano fiber and alkannin monomer are quite active to the removing of DPPH free radical, this proves from another point of view that also alkannin is in the stability after the high pressure electrospinning, be that alkannin still keeps its free radical scavenging activity, not inactivation in preparation process in composite nano fiber.
6. antibacterial activity is measured
Choose Gram-negative bacteria Escherichia coli (Escherichia coli) and gram-positive bacteria staphylococcus aureus (Staphylococcus aureus) and be the test bacterial classification, investigate the antibacterial activity of alkannin medicament-carrying composite nano-fiber with inhibition zone method.As shown in table 1, the PCL/PTMC composite nano fiber that is loaded with alkannin differs to two kinds of bacterium bacteriostatic activities: the antibacterial activity to staphylococcus aureus is stronger, Escherichia coli are then suppressed effect a little less than.This result with some bibliographical informations is consistent, and main cause may be the selection inhibition of one side alkannin to some bacterial classification; Because Gram-negative bacteria (as Escherichia coli) also has one deck lipopolysaccharides coated because cell membrane is outer, to a certain degree reduced its sensitiveness to external world on the other hand, thereby it is low to its inhibition effect to show as alkannin.
Table 1 is loaded with the antibacterial activity of the PCL/PTMC composite nano fiber of alkannin
Take by weighing the 0.0082g alkannin, 0.4022g PCL and 0.4018g PTMC, make them be dissolved in 10mL carrene/N, dinethylformamide (3: 1, v/v) in the mixed solvent, sonic oscillation makes abundant dissolving, obtains concentration 8.0% (w/v), PCL/PTMC mass ratio 5: 5, alkannin and with respect to high molecular mass fraction be 1% homogeneous solution.
The solution that configures is poured in the 5mL syringe, adopted No. 8 syringe needles to make flat mouthful spinning head.The flow velocity of solution at the spinning nozzle place is 0.8mL/h, and the voltage that is applied is 14kV, and two die openings obtain being loaded with the PCL/PTMC5 of 1% alkannin from being 18cm: 5 composite nano fiber.It is carried out above each test, the results are shown in Figure of description.
Take by weighing the 0.0399g alkannin, 0.7234g PCL and 0.0811g PTMC, make them be dissolved in 10mL carrene/N, dinethylformamide (3: 1, v/v) in the mixed solvent, sonic oscillation makes abundant dissolving, obtains concentration 8.0% (w/v), PCL/PTMC mass ratio 9: 1, alkannin and with respect to high molecular mass fraction be 5% homogeneous solution.
The solution that configures is poured in the 5mL syringe, adopted No. 8 syringe needles to make flat mouthful spinning head.The flow velocity of solution at the spinning nozzle place is 0.8mL/h, and the voltage that is applied is 14kV, and two die openings obtain being loaded with the PCL/PTMC9 of 5% alkannin from being 18cm: 1 composite nano fiber.It is carried out above each test, the results are shown in Figure of description.
Claims (8)
1. shikonin PCL/PTMC composite nano fiber, its component comprises: alkannin, poly-epsilon-caprolactone PCL and PTMC PTMC, wherein alkannin is 0.001～50: 100 with PCL/PTMC high molecule mass ratio, and the mass ratio of PCL and PTMC is 1: 100～100: 1.
2. a kind of shikonin PCL according to claim 1/PTMC composite nano fiber is characterized in that: the mass ratio of described PCL and PTMC is 9: 1,7: 3 or 5: 5.
3. a kind of shikonin PCL according to claim 1/PTMC composite nano fiber is characterized in that: described alkannin is 1% or 5% with PCL/PTMC high molecule mass ratio.
4. a kind of shikonin PCL according to claim 1/PTMC composite nano fiber is characterized in that: described shikonin PCL/its diameter of PTMC composite nano fiber is 150～400nm.
5. a kind of shikonin PCL according to claim 1/PTMC composite nano fiber, it is characterized in that: described alkannin extracts by the following method, Asian puccoon medicinal material 1kg, be ground into meal, the apparatus,Soxhlet's of in batches packing into adopts benzinum for extracting solvent extraction 3d, merges extract, extract is evaporated to medicinal extract, and it is carried out column chromatography for separation.
6. the preparation method of shikonin PCL/PTMC composite nano fiber comprises:
(1) with alkannin, PCL and PTMC dissolving and carrene/N jointly according to the above ratio, in the mixed solvent of dinethylformamide, preparation contains the carrier macromolecule mixed solution of alkannin; Wherein, carrene and N, the volume ratio of dinethylformamide is 100: 0～40: 60, PCL/PTMC high molecule mass and carrene/N, the ratio of dinethylformamide mixed solvent is 8g: 100ml;
(2) above-mentioned mixed solution is carried out electrostatic spinning, the temperature that controls environment is 10-35 ℃, and the feeding rate of solution is 0.8mL/h, and voltage is 14kV, and screen needle gage 18cm promptly gets the PCL/PTMC composite nano fiber that is loaded with alkannin.
7. the preparation method of a kind of shikonin PCL according to claim 5/PTMC composite nano fiber is characterized in that: carrene and N in the described step (1), the volume ratio of dinethylformamide is 3: 1.
Shikonin PCL/PTMC composite nano fiber be applied to that medicine sustained and controlled release system, wound are coated, the preparation of tumor post-operation topical therapeutic and biomedicine field.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102641520A (en) * | 2012-05-07 | 2012-08-22 | 吉林大学 | Preparation method of biological repair nano dressing containing wood frog skin polypeptide and being used for wounds and burn |
| CN116172992A (en) * | 2022-12-12 | 2023-05-30 | 吉林大学 | Water-phase dispersed transition metal ion/shikonin composite nano particle and two-phase preparation method thereof |
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| KR100932688B1 (en) * | 2007-07-06 | 2009-12-21 | 한국과학기술연구원 | Tubular porous scaffold with double membrane structure for artificial blood vessel and its manufacturing method |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102641520A (en) * | 2012-05-07 | 2012-08-22 | 吉林大学 | Preparation method of biological repair nano dressing containing wood frog skin polypeptide and being used for wounds and burn |
| CN116172992A (en) * | 2022-12-12 | 2023-05-30 | 吉林大学 | Water-phase dispersed transition metal ion/shikonin composite nano particle and two-phase preparation method thereof |
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