CN101342141A - Method for manufacturing organic metal anti-cancer medicine micro-nono-fibre having shell-core structure with coaxial cospinning technique - Google Patents
Method for manufacturing organic metal anti-cancer medicine micro-nono-fibre having shell-core structure with coaxial cospinning technique Download PDFInfo
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- CN101342141A CN101342141A CNA2008100418996A CN200810041899A CN101342141A CN 101342141 A CN101342141 A CN 101342141A CN A2008100418996 A CNA2008100418996 A CN A2008100418996A CN 200810041899 A CN200810041899 A CN 200810041899A CN 101342141 A CN101342141 A CN 101342141A
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Abstract
The invention belongs to the technical field of nano-drugs, particularly relates to a method for preparing shell-core structure organic metal anticancer drug miro/nano-fibers with a co-axial electrospinning technique. The detailed steps are as follows: core solution A and shell solution B are respectively prepared and put in glass dishes to be stirred by a magnetic stirring apparatus till being dissolved completely. The core solution A is added into a first liquid storage tube, and the shell solution B is added into a second liquid storage tube; under the condition that a high voltage elecstrostatic generator applies voltage, the core solution A is jetted from an inner nozzle needle, the shell solution B is jetted from an outer nozzle needle, and the obtained fiber is collected at collection screens after passing through nozzles. The environmental temperature is controlled between 18 DEG C to 20 DEG C; the environmental humidity is controlled between 45 percent to 50 percent; the distance between the collection screens is 14cm to 15cm; the voltage is 15KV to 20KV; the mass velocity of the inner nozzle needle is 0.5ml to 6ml per hour; the mass velocity of the outer nozzle needle is 5ml to 8ml per hour. The obtained fiber is collected at the collection screens. The invention has the advantages of stable reaction, simple and easy controllable operation, low cost, no pollution, uniform distribution of the product, difficult agglomeration, high purity quotient and easy industrialization.
Description
Technical field
The invention belongs to the Nano medication technical field, be specifically related to have the method for shell-cored structure organic metal cancer therapy drug micro/nano-fibre a kind of the preparation with coaxial co spun technology.
Background technology
Cancer is one of principal disease of serious harm human health, and capture cancer is the research topic of attracting attention in the world always.Shortcomings such as numerous organic metal anticarcinogens are low because of water solublity, acting duration is short, cytotoxicity is big are restricted in the use.Nano material is owing to its premium properties that is different from body material and individual molecule causes people's great attention.Through after the miniaturization, can improve its bioavailability to the metal cancer therapy drug well, reduce the toxic and side effects of medicine.
Electrospinning silk technology is directly to prepare one of most important, effective method of nanofiber.The electrostatic spinning process device is simple, mild condition, but also can influence the structure of material by changing preparation condition, reach the purpose of control drug release amount and speed.Adopt the coaxial electrically spun technology, more can prepare the micro/nano-fibre of shell-cored structure, pharmaceutical pack is overlayed on the core of nanofiber, skin is degradable material.The nanofiber that obtains that this mode prepares can be used as a kind of novel medicament carrier, and its great specific surface area can make that medicine is easier to be absorbed by the body.Reports such as Verreck think that particularly for the lower medicine of dissolubility in the water, superfine fibre can improve bioavailability of medicament greatly as its release vehicle.Simultaneously, utilizing this method also can reach controlled delivery of pharmaceutical agents discharges.At present, also not about the organic metal cancer therapy drug being carried out micro-nanoization to reach the research report of controlled delivery of pharmaceutical agents release and raising anti-cancer properties with electrostatic spinning technique.
Summary of the invention
The objective of the invention is to propose a kind of simple and easy, prepare the method for shell-cored structure organic metal cancer therapy drug micro/nano-fibre with coaxial co spun technology easily.
What the present invention proposed prepares the method for shell-cored structure organic metal cancer therapy drug micro/nano-fibre with coaxial co spun technology, and concrete steps are as follows:
(1) solution preparation: preparation is that the mass fraction of solvent is the core matter solution A of 0.1-2.0wt% with the dichloromethane, places in the glass dish and stir 1.5-2.5h under the magnetic stirring apparatus effect, to dissolving fully; Preparation is that the mass fraction of solvent is the chitin solution B of 2.0-8.0wt% with the dichloromethane, places in the glass dish and stir 1.5-2.52h under the magnetic stirring apparatus effect, to dissolving fully;
(2) spinning process: as shown in Figure 1, adopt the coaxial electrically spun device to carry out spinning, Teflon pipe (Teflon pipe) 1 one ends link to each other with first liquid storage pipe 7 by stainless pin 2, and the other end is connected with interior nozzle needle 9, and first liquid storage pipe, 7 other ends connect syringe pump 3, interior nozzle needle 9 links to each other with shower nozzle 6, interior nozzle needle 9 one sides are provided with outer nozzle needle 10, and outer nozzle needle 10 connects second liquid storage pipe 8, collects screen 5 ground connection, place under the shower nozzle 6, HV generator 4 is connected on the stainless pin 2; At first core matter solution A is stored in first liquid storage pipe 7, the chitin solution B is stored in second liquid storage pipe 8, apply under the voltage condition at HV generator 4, core matter solution A is by interior nozzle needle 9 ejections, the chitin solution B is by outer nozzle needle 10 ejections, through shielding on 5 from collecting again behind the shower nozzle 6, obtain required product; The temperature that controls environment is 18-20 ℃; Ambient humidity 45%-50%; The spacing of collecting screen is 14-15 centimetre; Voltage is 15-20KV; The mass velocity of interior nozzle needle is 0.5-6mL/h; The mass velocity of outer nozzle needle is 5-8mL/h.
Wherein, described solution A and solution B are respectively following solution:
Solution A is the dichloromethane solution of cyclopentadienyl titanium dichloride, and solution B is the dichloromethane solution of Poly-L-lactic acid (PLLA); Perhaps
Solution A is the dichloromethane solution (cisplatin is used N earlier, and dinethylformamide dissolves fully, solution is joined in the dichloromethane of certain volume then) of cisplatin, and solution B is the dichloromethane solution of Poly-L-lactic acid (PLLA).
Among the present invention, described in the step (1) in the chitin solution B, be that the mass ratio of PLLA in the solvent electrospinning effect when being 5wt% is better, be easy to spin that area is big, the higher nano fibrous membrane of thickness in the short time at dichloromethane.
Among the present invention, collect the screen place described in the step (2) and collect the product fiber.
Among the present invention, products obtained therefrom can select for use means such as XRD, TEM, SEM, TG that its structure and pattern are characterized.Among the present invention, the anti-cancer properties of products obtained therefrom can be measured by mtt assay.
Mechanism of the present invention is: in coaxial electrically spun, the liquid of core matter and chitin is respectively in two different syringes, inside and outside two-layer liquid is applied high pressure, because the quick volatilization of solvent, the liquid of ejection can form superfine spraying and solidify rapidly and be transformed into diameter and reach the following or nano level superfine fibre of micron, shields collection by the collection of ground connection.Because two liquid in the spinning process go out the time weak point of contact and the lower reason of diffusion coefficient of polymer at spout, they can be not admixed together before solidifying, thereby be solidified into ultra-fine co-axial nano fiber.
The present invention has the following advantages:
1, in preparation process, mild condition, production cost is lower.
2, because the present invention only need be by conditions such as control medicament contg, voltage, inside and outside nozzle needle the flow velocity just medicament contg, shell thickness, micro/nano-fibre thickness etc. of may command product, therefore further research be expected to realize medicine the location, regularly discharge.Be expected to simultaneously carry enough a kind of new carrier for the oral drug delivery of some drugs.
3, utilize the inventive method can spin that area is big, the higher micro-/ nano iatric fiber film of thickness in the short time.Have that medicine response rate height, product single output are big, product is easy to advantages such as preservations, very valuable concerning commercial Application, and expect to be generalized to large-scale application.
Description of drawings
Fig. 1 is used coaxial electrically spun device sketch map in the experiment.
Fig. 2 is the SEM photo of four kinds of micrometer/nanometer fibers obtaining among the embodiment 1-4.Wherein, (a) being the SEM photo of embodiment 1, (b) is the SEM photo of embodiment 2, (c) is the SEM photo of embodiment 3, (d) is the SEM photo of embodiment 4.
Fig. 3 is the TEM photo of four kinds of micrometer/nanometer fibers obtaining among the embodiment 1-4.Wherein, (a) being the TEM photo of embodiment 1, (b) is the TEM photo of embodiment 2, (c) is the TEM photo of embodiment 3, (d) is the TEM photo of embodiment 4.
Fig. 4 is raw material cyclopentadienyl titanium dichloride (A), PLLA fiber (B) and be loaded with the TG figure of the PLLA fiber (C) of cyclopentadienyl titanium dichloride.
Fig. 5 is the vitro drug release curve (37 ℃, pH7.4 PBS) of the nano fibrous membrane of electrospinning preparation.Wherein, curve a discharges the performance of cyclopentadienyl titanium dichloride for fibrous membrane under the situation that does not add E.C. 3.4.21.64, curve b discharges the performance of cyclopentadienyl titanium dichloride for the performance of the release of fibrous membrane under the situation that adds 10mg/L E.C. 3.4.21.64 cyclopentadienyl titanium dichloride, curve c for fibrous membrane under the situation that adds the 50mg/L E.C. 3.4.21.64.
Fig. 6 is the experimental result of mtt assay (the cyclopentadienyl titanium dichloride concentration that fibrous membrane discharges is 8.0 and 16.0mg/L, is expressed as PLLA8 and 16 respectively)
Number in the figure: 1 is the Teflon pipe, and 2 is stainless pin, and 3 is syringe pump, and 4 is HV generator, and 5 for collecting screen, and 6 is shower nozzle, and 7 is first liquid storage pipe, and 8 also is second liquid storage pipe, and 9 is interior nozzle needle, and 10 is outer nozzle needle.
The specific embodiment
The invention is further illustrated by the following examples.
Embodiment 1:
1) accurately measure PLLA (mass ratio of PLLA is 5wt% in dichloromethane solvent) solute and dichloromethane solvent with analytical balance after, place in the clean glass dish under the magnetic stirring apparatus effect stir about 2h to dissolving (core matter solution A) fully.After accurately measuring cyclopentadienyl titanium dichloride (the cyclopentadienyl titanium dichloride mass ratio is 0.4wt%) solute and dichloromethane solvent with analytical balance, place in the clean glass dish under the magnetic stirring apparatus effect stir about 2h to dissolving (chitin solution B) fully.
2) core matter solution A is added in first liquid storage pipe 7, the chitin solution B is added in second liquid storage pipe 8, and under HV generator applied voltage condition, core matter solution A was sprayed by interior nozzle needle, and the chitin solution B is sprayed by outer nozzle needle.Through behind the shower nozzle 6, collect the screen place and collect the product fiber.The temperature that controls environment is 18-20 ℃; Ambient humidity 45%-50%; The spacing of collecting screen is 14-15 centimetre.Voltage is 18.0KV; The mass velocity of interior nozzle needle is 3.0mL/h; The mass velocity of outer nozzle needle is 6.0mL/h.The product that obtains is a micron order, and size range is 1100-1400nm.
3) products obtained therefrom characterizes its structure and pattern with means such as XRD, TEM, SEM, TG; Measure medicine release in vitro situation by the uv-visible absorption spectra of cyclopentadienyl titanium dichloride; Study its anti-cancer properties with mtt assay.The result of TEM (Fig. 3) has illustrated that product has co-axial shell-cored structure.Fig. 5 shows that this system has the release action of controlling cyclopentadienyl titanium dichloride preferably.Fig. 6 shows that the cyclopentadienyl titanium dichloride that this system discharges still has the good anticancer performance.
Embodiment 2:
1) accurately measure PLLA (mass ratio of PLLA is 5wt% in dichloromethane solvent) solute and dichloromethane solvent with analytical balance after, place in the clean glass dish under the magnetic stirring apparatus effect stir about 2h to dissolving (core matter solution A) fully.After accurately measuring cyclopentadienyl titanium dichloride (the cyclopentadienyl titanium dichloride mass ratio is 0.4wt%) solute and dichloromethane solvent with analytical balance, place in the clean glass dish under the magnetic stirring apparatus effect stir about 2h to dissolving (chitin solution B) fully.
2) core matter solution A is added in first liquid storage pipe 7, the chitin solution B is added in second liquid storage pipe 8, and under HV generator applied voltage condition, core matter solution A was sprayed by interior nozzle needle, and the chitin solution B is sprayed by outer nozzle needle.Through behind the shower nozzle 6, collect the screen place and collect the product fiber.The temperature that controls environment is 18-20 ℃; Ambient humidity 45%-50%; The spacing of collecting screen is 14-15 centimetre.Voltage is 18.0KV; The mass velocity of interior nozzle needle is 6.0mL/h; The mass velocity of outer nozzle needle is 6.0mL/h.Collect the screen place and collect the product fiber.The product that obtains is a micron order, and size range is 1500-1800nm.
3) products obtained therefrom characterizes its structure and pattern with means such as XRD, TEM, SEM, TG; The medicine extracorporeal releasing quantity is read in uv-visible absorption spectra measurement by cyclopentadienyl titanium dichloride from standard curve; Study its anti-cancer properties with mtt assay.
Embodiment 3:
1) accurately measure PLLA (mass ratio of PLLA is 5wt% in dichloromethane solvent) solute and dichloromethane solvent with analytical balance after, place in the clean glass dish under the magnetic stirring apparatus effect stir about 2h to dissolving (core matter solution A) fully.After accurately measuring cyclopentadienyl titanium dichloride (the cyclopentadienyl titanium dichloride mass ratio is 0.6wt%) solute and dichloromethane solvent with analytical balance, place in the clean glass dish under the magnetic stirring apparatus effect stir about 2h to dissolving (chitin solution B) fully.
2) core matter solution A is added in first liquid storage pipe 7, the chitin solution B is added in second liquid storage pipe 8, and under HV generator applied voltage condition, core matter solution A was sprayed by interior nozzle needle, and the chitin solution B is sprayed by outer nozzle needle.Through behind the shower nozzle 6, collect the screen place and collect the product fiber.The temperature that controls environment is 18-20 ℃; Ambient humidity 45%-50%; The spacing of collecting screen is 14-15 centimetre.Voltage is 19.0KV; The mass velocity of interior nozzle needle is 6.0mL/h; The mass velocity of outer nozzle needle is 3.0mL/h.Collect the screen place and collect the product fiber.The product that obtains is a nanoscale, and size range is 220-300nm.
3) products obtained therefrom characterizes its structure and pattern with means such as XRD, TEM, SEM, TG; The medicine extracorporeal releasing quantity is read in uv-visible absorption spectra measurement by cyclopentadienyl titanium dichloride from standard curve; Study its anti-cancer properties with mtt assay.(seeing accompanying drawing)
Embodiment 4:
1) accurately measure PLLA (mass ratio of PLLA is 6wt% in dichloromethane solvent) solute and dichloromethane solvent with analytical balance after, place in the clean glass dish under the magnetic stirring apparatus effect stir about 2h to dissolving (core matter solution A) fully.After accurately measuring cyclopentadienyl titanium dichloride (the cyclopentadienyl titanium dichloride mass ratio is 0.6wt%) solute and dichloromethane solvent with analytical balance, place in the clean glass dish under the magnetic stirring apparatus effect stir about 2h to dissolving (chitin solution B) fully.
2) core matter solution A is added in first liquid storage pipe 7, the chitin solution B is added in second liquid storage pipe 8, and under HV generator applied voltage condition, core matter solution A was sprayed by interior nozzle needle, and the chitin solution B is sprayed by outer nozzle needle.Through behind the shower nozzle 6, collect the screen place and collect the product fiber.The temperature that controls environment is 18-20 ℃; Ambient humidity 45%-50%; The spacing of collecting screen is 14-15 centimetre.Voltage is 19.0KV; The mass velocity of interior nozzle needle is 6.0mL/h; The mass velocity of outer nozzle needle is 6.0mL/h.Collect the screen place and collect the product fiber.The product that obtains is a nanoscale, and size range is 1900-460nm.
3) products obtained therefrom characterizes its structure and pattern with means such as XRD, TEM, SEM, TG; The medicine extracorporeal releasing quantity is read in uv-visible absorption spectra measurement by cyclopentadienyl titanium dichloride from standard curve; Study its anti-cancer properties with mtt assay.
Embodiment 5:
1) accurately measure PLLA (mass ratio of PLLA is 5wt% in dichloromethane solvent) solute and dichloromethane solvent with analytical balance after, place in the clean glass dish under the magnetic stirring apparatus effect stir about 2h to dissolving (core matter solution A) fully.Accurately measure cisplatin (the cisplatin mass ratio is 0.2wt%) solute with analytical balance, use earlier N, dinethylformamide dissolves fully, solution is joined in the dichloromethane of certain volume then, place stir about 2h dissolving (chitin solution B) extremely fully under the magnetic stirring apparatus effect in the clean glass dish.
2) core matter solution A is added in first liquid storage pipe 7, the chitin solution B is added in second liquid storage pipe 8, and under HV generator applied voltage condition, core matter solution A was sprayed by interior nozzle needle, and the chitin solution B is sprayed by outer nozzle needle.Through behind the shower nozzle 6, collect the screen place and collect the product fiber.The temperature that controls environment is 18-20 ℃; Ambient humidity 45%-50%; The spacing of collecting screen is 14-15 centimetre.Voltage is 16.4KV; The mass velocity of interior nozzle needle is 3.0mL/h; The mass velocity of outer nozzle needle is 6.0mL/h.Collect the screen place and collect the product fiber.
3) products obtained therefrom characterizes its structure and pattern with means such as XRD, TEM, SEM, TG; The medicine extracorporeal releasing quantity is read in uv-visible absorption spectra measurement by cyclopentadienyl titanium dichloride from standard curve; Study its anti-cancer properties with mtt assay.
Embodiment 6:
1) accurately measure PLLA (mass ratio of PLLA is 5wt% in dichloromethane solvent) solute and dichloromethane solvent with analytical balance after, place in the clean glass dish under the magnetic stirring apparatus effect stir about 2h to dissolving (core matter solution A) fully.Accurately measure cisplatin (the cisplatin mass ratio is 0.2wt%) solute with analytical balance, use earlier N, dinethylformamide dissolves fully, solution is joined in the dichloromethane of certain volume then, place stir about 2h dissolving (chitin solution B) extremely fully under the magnetic stirring apparatus effect in the clean glass dish.
2) core matter solution A is added in first liquid storage pipe 7, the chitin solution B is added in second liquid storage pipe 8, and under HV generator applied voltage condition, core matter solution A was sprayed by interior nozzle needle, and the chitin solution B is sprayed by outer nozzle needle.Through behind the shower nozzle 6, collect the screen place and collect the product fiber.The temperature that controls environment is 18-20 ℃; Ambient humidity 45%-50%; The spacing of collecting screen is 14-15 centimetre.Voltage is 14.0KV; The mass velocity of interior nozzle needle is 3.0mL/h; The mass velocity of outer nozzle needle is 6.0mL/h.Collect the screen place and collect the product fiber.
3) products obtained therefrom characterizes its structure and pattern with means such as XRD, TEM, SEM, TG; The medicine extracorporeal releasing quantity is read in uv-visible absorption spectra measurement by cyclopentadienyl titanium dichloride from standard curve; Study its anti-cancer properties with mtt assay.
Embodiment 7:
1) accurately measure PLLA (mass ratio of PLLA is 5wt% in dichloromethane solvent) solute and dichloromethane solvent with analytical balance after, place in the clean glass dish under the magnetic stirring apparatus effect stir about 2h to dissolving (core matter solution A) fully.Accurately measure cisplatin (the cisplatin mass ratio is 0.2wt%) solute with analytical balance, use earlier N, dinethylformamide dissolves fully, solution is joined in the dichloromethane of certain volume then, place stir about 2h dissolving (chitin solution B) extremely fully under the magnetic stirring apparatus effect in the clean glass dish.
2) core matter solution A is added in first liquid storage pipe 7, the chitin solution B is added in second liquid storage pipe 8, and under HV generator applied voltage condition, core matter solution A was sprayed by interior nozzle needle, and the chitin solution B is sprayed by outer nozzle needle.Through behind the shower nozzle 6, collect the screen place and collect the product fiber.The temperature that controls environment is 18-20 ℃; Ambient humidity 45%-50%; The spacing of collecting screen is 14-15 centimetre.Voltage is 16.4KV; The mass velocity of interior nozzle needle is 3.0mL/h; The mass velocity of outer nozzle needle is 5.0mL/h.Collect the screen place and collect the product fiber.
3) products obtained therefrom characterizes its structure and pattern with means such as XRD, TEM, SEM, TG; The medicine extracorporeal releasing quantity is read in uv-visible absorption spectra measurement by cyclopentadienyl titanium dichloride from standard curve; Study its anti-cancer properties with mtt assay.
Embodiment 8:
1) accurately measure PLLA (mass ratio of PLLA is 5wt% in dichloromethane solvent) solute and dichloromethane solvent with analytical balance after, place in the clean glass dish under the magnetic stirring apparatus effect stir about 2h to dissolving (core matter solution A) fully.Accurately measure cisplatin (the cisplatin mass ratio is 0.2wt%) solute with analytical balance, use earlier N, dinethylformamide dissolves fully, solution is joined in the dichloromethane of certain volume then, place stir about 2h dissolving (chitin solution B) extremely fully under the magnetic stirring apparatus effect in the clean glass dish.
2) core matter solution A is added in first liquid storage pipe 7, the chitin solution B is added in second liquid storage pipe 8, and under HV generator applied voltage condition, core matter solution A was sprayed by interior nozzle needle, and the chitin solution B is sprayed by outer nozzle needle.Through behind the shower nozzle 6, collect the screen place and collect the product fiber.The temperature that controls environment is 18-20 ℃; Ambient humidity 45%-50%; The spacing of collecting screen is 14-15 centimetre.Voltage is 16.4KV; The mass velocity of interior nozzle needle is 6.0mL/h; The mass velocity of outer nozzle needle is 6.0mL/h.Collect the screen place and collect the product fiber.
3) products obtained therefrom characterizes its structure and pattern with means such as XRD, TEM, SEM, TG; The medicine extracorporeal releasing quantity is read in uv-visible absorption spectra measurement by cyclopentadienyl titanium dichloride from standard curve; Study its anti-cancer properties with mtt assay.
Claims (1)
1, a kind ofly prepare the method for shell-cored structure organic metal cancer therapy drug micro/nano-fibre, it is characterized in that concrete steps are as follows with coaxial co spun technology:
1. solution preparation: preparation is that the mass fraction of solvent is the core matter solution A of 0.1-2.0wt% with the dichloromethane, places in the glass dish and stir 1.5-2.5h under the magnetic stirring apparatus effect, to dissolving fully; Preparation is that the mass fraction of solvent is the chitin solution B of 2.0-8.0wt% with the dichloromethane, places in the glass dish and stir 1.5-2.52h under the magnetic stirring apparatus effect, to dissolving fully;
2. spinning process: adopt the coaxial electrically spun device to carry out spinning, Teflon pipe (1) one end links to each other with first liquid storage pipe (7) by stainless pin (2), the other end is connected with interior nozzle needle (9), first liquid storage pipe (7) other end connects syringe pump (3), interior nozzle needle (9) links to each other with shower nozzle (6), interior nozzle needle (9) one sides are provided with outer nozzle needle (10), outer nozzle needle (10) connects second liquid storage pipe (8), collect screen (5) ground connection, place under the shower nozzle (6), HV generator (4) is connected on the stainless pin (2); At first core matter solution A is stored in first liquid storage pipe (7), the chitin solution B is stored in second liquid storage pipe (8), apply under the voltage condition at HV generator (4), core matter solution A is sprayed by interior nozzle needle (9), the chitin solution B is sprayed by outer nozzle needle (10), through shielding on (5) from collecting again behind the shower nozzle (6), obtain required product; The temperature that controls environment is 18-20 ℃; Ambient humidity 45%-50%; The spacing of collecting screen is 14-15 centimetre; Voltage is 15-20KV; The mass velocity of interior nozzle needle is 0.5-6mL/h; The mass velocity of outer nozzle needle is 5-8mL/h;
Wherein, described solution A and solution B are respectively following solution:
Solution A is the dichloromethane solution of cyclopentadienyl titanium dichloride, and solution B is the dichloromethane solution of Poly-L-lactic acid; Perhaps
Solution A is the dichloromethane solution of cisplatin, and solution B is the dichloromethane solution of Poly-L-lactic acid.
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| CN107115268A (en) * | 2017-05-22 | 2017-09-01 | 四川大学 | Coaxial electrostatic spinning injectable fiber and preparation method thereof |
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| CN105997945A (en) * | 2016-07-08 | 2016-10-12 | 四川大学 | Preparation method of macromolecule nanoparticles capable of transmitting two or more types of medicine |
| CN106038486A (en) * | 2016-07-08 | 2016-10-26 | 四川大学 | Macromolecule micelle capable of transmitting two or more antitumor drugs and preparing method thereof |
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Open date: 20090114 |