CN109718383A - A kind of dendrimer load platinum medicine and its preparation method and application that SP peptide is modified - Google Patents
A kind of dendrimer load platinum medicine and its preparation method and application that SP peptide is modified Download PDFInfo
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- CN109718383A CN109718383A CN201711028961.3A CN201711028961A CN109718383A CN 109718383 A CN109718383 A CN 109718383A CN 201711028961 A CN201711028961 A CN 201711028961A CN 109718383 A CN109718383 A CN 109718383A
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Abstract
The invention belongs to field of biotechnology, are related to a kind of dendrimer load platinum medicine and its preparation method and application of SP peptide modification.Platinum medicine is supported on dendritic macromole polylysine using common metal-chelator DTPA and forms nanoparticle by the present invention, upper SP peptide is modified simultaneously as target function group, the nanometer system can be mediated to pass through blood-brain barrier and targeting glioma cells in tissue, effective targeted delivery is carried out to platinum medicine.The dendrimer load platinum medicine of SP peptide modification of the invention can be used for preparing the new formulation for the treatment of glioma, can heighten the effect of a treatment and reduce side effect.
Description
Technical field
The invention belongs to field of biotechnology, the dendrimer for being related to a kind of SP peptide modification loads platinum medicine and its preparation
Method and purposes.
Background technique
It is the most common tumour of central nervous system prior art discloses glioma, accounts for about 40%.Glioma tool
There is the features such as multiple, to be dispersed in, infiltrate, five year survival rate is less than 5%.The conventional therapy measure of glioma is surgical resection plus adjuvant
Chemicotherapy.Due to the characteristic that owned infiltration type is grown, operation is difficult to cut entirely, so that chemotherapy becomes indispensable treatment
Means.But due to the presence of blood-brain barrier, most chemotherapeutics is caused to be difficult to accumulate into brain and in tumor locus.
Currently, platinum medicine is the clinically highest anti-tumor drug of frequency of use.Platinum medicine is with wide spectrum and efficiently
The advantages of.The suggestions such as the comprehensive cancer network of American National are clinically using platinum medicine as one of adjuvant chemotherapy scheme, still, platinum
Class drug cannot cross blood-brain barrier, and be the mode by free diffusing since platinum medicine passes through cell membrane, lead to it
It is difficult to generate accumulation in tumor locus, therefore platinum medicine is directly used for the chemotherapy of glioma, then is easy to generate serious
Neurotoxicity.
In view of the above-mentioned problems, thering is scholar to attempt for platinum medicine to be supported on carrier by physical action, once to reach
The purpose of delivering, but unstable products are easy to reveal preparation in blood circulation；There are also scholars to utilize the side of oxidation
Platinum medicine is made into prodrug by method, but there are still prodrugs to be reduced into the risk being metabolized before raw medicine in vivo.
Status based on the prior art, present inventor is quasi- to provide a kind of dendrimer Supported Pt Nanoparticles of SP peptide modification
Class drug and its preparation method and application.
Summary of the invention
It is an object of the invention to the statuses based on the prior art, provide a kind of dendrimer Supported Pt Nanoparticles of SP peptide modification
Class drug and its preparation method and application.
The present invention utilizes the chelation of metal-ligand, is not changing the valence state of the core element platinum in platinum medicine
Under the premise of, blood-brain barrier can be passed through by the design of nano-carrier and release platinum medicine on demand at targeting, be expected to reach
The purpose of Synergy and attenuation.Platinum medicine is supported on the poly- L- of dendritic macromole using common metal-chelator DTPA by the present invention
Nanoparticle is formed on lysine, while modifying upper SP peptide as target function group, and the nanometer system can be mediated to pass through blood brain
Barrier and targeting glioma cells in tissue, carry out effective targeted delivery to platinum medicine.The dendroid of SP peptide modification of the invention
Molecule load platinum medicine can be used for preparing the new formulation for the treatment of glioma, can heighten the effect of a treatment and reduce side effect.
Specifically, the first object of the present invention is to provide a kind of SP peptide using platinum medicine treatment glioma and repair
The dendrimer nanoparticle of the load platinum medicine of decorations, composition characteristic are: the nanoparticle is by polylysine, SP
Peptide, polyethylene glycol, DTPA, (1,2- diaminocyclohexane) platinous chloride are constituted.
Preferably, the polylysine, SP peptide, polyethylene glycol, DTPA, (1,2- diaminocyclohexane) platinous chloride rub
You are than being 1:8:15:20:100.Preferably, the total quality of materials score of metal platinum Zhan is 14.4%.
Preferably, the polylysine is third generation DGL, it is characterised in that possesses 123 primary amino groups, diameter is received for 6
Rice, molecular weight 22000.
Preferably, the polyethylene glycol is straight chain polyethylene glycol, it is characterised in that end-capping group is azido and NHS activity
Ester, molecular weight 3500.
Preferably, the DTPA, it is characterised in that: refer to S-2- (4- isothiocyanic acid benzyl)-diethylenetriamine pentaacetic acid, i.e.,
p-SCN-Bn-DTPA。
Preferably, the SP peptide, it is characterised in that: sequence RPKPQQFFGLM, and upper 5- hexin is modified in amino terminal
Acid.
Preferably, stating the connection type between polylysine, polyethylene glycol, SP peptide and DTPA is covalent key connection.
Preferably, chelation of the connection type between the DTPA and platinum medicine between metal-ligand.
The present invention provides a kind of dendrimer nanoparticle preparation sides of the load platinum medicine of SP peptide modification
Method the steps include:
1) the chelate products Pt-DTPA between DTPA and platinum medicine is prepared；
2) it prepares polylysine-polyethylene glycol covalent linkage object and obtains DGL-PEG；
3) by the 1) chelate products be connected to 2) described in covalent linkage object on, obtain Pt-DTPA-DGL-PEG；
4) by SP peptide be connected to 3) described in DTPA-DGL-PEG on obtain final products.
Preferably, the process for sequestration between the DTPA and platinum medicine, it is characterized in that: in deionized water, addition rubs
You than be 1:1 (1,2- diaminocyclohexane) platinous chloride and silver nitrate, and in the dark with stirred 24 hours under the conditions of 25 degree,
By being centrifuged and being filtered to remove silver chlorate, (1,2- diaminocyclohexane) chlorine nitration platinum aqueous solution is obtained, is then added 0.2
S-2- (4- isothiocyanic acid benzyl)-diethylenetriamine pentaacetic acid of mole, stirs 24 hours under the conditions of 25 degree and obtains DTPA and platinum
The chelate products of class drug.
Preferably, the polylysine-polyethylene glycol is covalently attached method, it is characterized in that: the phosphate for being 8.0 in pH
In buffer, the straight chain polyethylene glycol for polylysine, azido and NHS the active ester sealing end that molar ratio is 1:15 is added,
Stirring 2 hours under 25 degree.Ultrafiltration removes unreacting material and buffer is changed to the phosphate buffer that pH is 7.0.
Preferably, chelate products are connected to the method for being covalently attached object, feature according to claim feature 11
Are as follows: in the 4- hydroxyethyl piperazineethanesulfonic acid buffer that pH is 8.2, the poly- second two of polylysine-that molar ratio is 1:20 is added
The chelate of alcohol attachment and DTPA and platinum medicine stirs 24 hours at 25 degrees c, and is 5000 using molecular weight retention
Bag filter is dialysed 24 hours in water, and freeze-drying obtains Pt-DTPA-DGL-PEG.
Preferably, described by SP peptide connection method, it is characterized in that: in n,N-Dimethylformamide, molar ratio, which is added, is
Pt-DTPA-DGL-PEG, SP peptide, cuprous iodide, sodium ascorbate and the n,N-diisopropylethylamine of 1:5:2.5:5:5.30
The lower stirring of degree 12 hours, and the bag filter for being 5000 using molecular weight retention, respectively in 10 mMs of ethylenediamine tetra-acetic acid
It in two sodium solutions and dialyses 24 hours in pure water, freeze-drying obtains final products SDDPt.
From above-mentioned preparation method and subsequent embodiment of the present invention: the dendrimer of load platinum medicine of the invention
Nanoparticle at least has the advantage that
1) it mainly includes polylysine and poly- second two that the basis of dendrimer nanoparticle of the present invention, which constitutes raw material,
Alcohol will not generate toxicity to body after dendrimer nanoparticle degradation in vivo.
2) it was found that small particle is to blood-brain barrier is passed through larger help, dendrimer nanoparticle grain of the present invention
Diameter is only 19.65 ± 4.65 nanometers, delivers field in brain diseases, has the advantage on partial size compared to common nano material,
Dendrimer nanoparticle of the present invention potential in pure water is 3.5 ± 0.9 nanometers, this potential facilitates in blood circulation
Keep certain stability.Dendrimer nanoparticle of the present invention surface is wrapped in a strata glycol molecule, biofacies
Capacitive is good and can be in order to avoid immunosurveillance, is further ensured that the stability in blood circulation.
3) compared with traditional intravenously administrable, the formulation method in the present invention can assist platinum medicine across blood-brain barrier and store
Product realizes the accurate target practice of drug at glioma lesion, improves curative effect and reduces system toxicity.
To sum up, the present invention provides a kind of efficient, peaces using platinum medicine treatment glioma for selection of clinical
Full method.
Detailed description of the invention
Fig. 1 is the dendrimer nanoparticle preparation flow and characterization for loading platinum medicine,
Wherein, A is the dendrimer nanoparticle synthesis step for loading platinum medicine；
B is the nucleus magnetic hydrogen spectrum figure of the not yet dendrimer nanoparticle of connection SP peptide load platinum medicine；
C is the nucleus magnetic hydrogen spectrum figure of the still dendrimer nanoparticle of connection SP peptide load platinum medicine；
D is the grain size distribution for loading the dynamic light scattering of the dendrimer nanoparticle of platinum medicine and measuring；
E is the transmission electron microscope phenogram for loading the dendrimer nanoparticle of platinum medicine.
Fig. 2 is platinum medicine vitro release kinetics from the dendrimer nanoparticle of load platinum medicine.
Fig. 3 is that dendrimer nanoparticle passes through blood-brain barrier capability representation in vivo and in vitro,
Wherein, A is across the blood-brain barrier ability of mouse brain capillary endothelial cell monofilm model in-vitro evaluation nanoparticle；
B is to utilize across the blood-brain barrier ability of healthy mouse interior evaluating nanoparticle.
Fig. 4 is the distribution schematic diagram of dendrimer nanoparticle in vivo,
Wherein, A is different time points dendrimer nanoparticle distribution schematic diagram in tumor-bearing mice body；
B is the main organs dendrimer nanoparticle distribution map that tumor-bearing mice is dissected after 24 hours；
C is dendrimer nanoparticle 3D distribution schematic diagram in tumor-bearing mice body after 24 hours.
Fig. 5 is dendrimer nanoparticle vitro cytotoxicity schematic diagram.
Fig. 6 is dendrimer nanoparticle to lotus glioma mouse drug effect schematic diagram.
Wherein, A is that different groups handle lotus glioma mouse survival curve；It is small that B difference group handles lotus glioma
Mouse changes of weight curve.
Specific embodiment
Below by way of the specific embodiment technical solution that the present invention will be described in detail, it should be understood that specific embodiment below
It is merely illustrative, any change or variation are designed without departing from technical solution of the present invention, should all be wanted in right of the present invention
It asks within protection scope.
Embodiment 1
(1, the 2- diaminocyclohexane) two that molar ratio is 1:1 is added in deionized water in synthesis step as shown in Figure 1A
Platinum chloride and silver nitrate, and stirred 24 hours under the conditions of 25 degree in the dark, by being centrifuged and being filtered to remove silver chlorate, obtain
Then the S-2- (4- isothiocyanic acid benzyl)-two of 0.2 mole is added in (1,2- diaminocyclohexane) chlorine nitration platinum aqueous solution
Second pentaacetic acid stirs 24 hours under the conditions of 25 degree and obtains the chelate products of DTPA and platinum medicine.Molar ratio is 1:10
Bifunctional dough NHS-PEG3500-N3The phosphate buffer of pH8.0 is dissolved in polylysine dendrimer
In, it is stirred at 25 degree 24 hours, then ultrafiltration removes unreacting material and buffer is changed to the phosphate-buffered that pH is 7.0
Liquid.In the 4- hydroxyethyl piperazineethanesulfonic acid buffer that pH is 8.2, the poly- second two of polylysine-that molar ratio is 1:20 is added
The chelate of alcohol attachment and DTPA and platinum medicine stirs 24 hours at 25 degrees c, and is 5000 using molecular weight retention
Bag filter is dialysed 24 hours in water, and freeze-drying obtains Pt-DTPA-DGL-PEG.Its structure is characterized using nuclear magnetic resonance spectroscopy
(Figure 1B).In n,N-Dimethylformamide, Pt-DTPA-DGL-PEG, SP peptide, the iodine that molar ratio is 1:5:2.5:5:5 is added
Change cuprous, sodium ascorbate and n,N-diisopropylethylamine.It is stirred 12 hours under 30 degree, and is 5000 using molecular weight retention
Bag filter, in 10 mMs of disodium ethylene diamine tetra-acetic acid solution and dialyse 24 hours in pure water respectively, freeze-drying
Obtain final products SDDPt.Its structure (Fig. 1 C) is characterized using nuclear magnetic resonance spectroscopy.Inductively coupled plasma body atomic emissions light
It is 14.4% that spectrometry, which measures platinum constituent content,.
Embodiment 2
The dendrimer nanoparticle that 5 milligrams load platinum medicine is dissolved in 2 ml deionized waters, is vortexed 5 minutes,
Using particle diameter in dynamic light scattering measurement solution and Z potential, measure partial size and potential be respectively 19.65 ± 4.65 nanometers and
3.5 ± 0.9 millivolts
Embodiment 3
The dendrimer nanoparticle that 5 milligrams load platinum medicine is dissolved in 2 ml deionized waters, is vortexed 5 minutes
It is allowed to drop after being uniformly distributed and utilizes transmission electron microscope observation nanoparticle after drying under infrared lamp on carbon coating copper mesh
(Fig. 1 E).Nanometer appearance is regular, has good dispersion degree, illustrates not formed more large-sized association body between nanoparticle.
Transmission electron microscope is close to the particle diameter measurements and dynamic light scattering result of particle.
Embodiment 4
The dendrimer nanoparticle that 5 milligrams load platinum medicine is dissolved in the phosphate buffer of 2 milliliters of pH7.4
In, it is vortexed 5 minutes and is allowed to be uniformly distributed, be transferred in the bag filter that molecular cut off is 3500 and tighten, be placed in 500 milliliters and contain
In the phosphate buffer of the pH7.4 of 0.15 mole of every liter of sodium chloride.In the shaking table under the revolving speed of 37 degree of 100rpm, take every time
The outer 2 milliliters of phosphate buffers of bag filter out measure platinum constituent content using inductively coupled plasma atomic emission spectrometry,
And it is added to the phosphate buffer of 2 milliliters of fresh pH7.4 for containing 0.15 mole of every liter of sodium chloride.(1,2- diaminocyclohexane)
Platinous chloride is as a control group.As shown in Fig. 2, control group is discharged by way of free diffusing into slot quickly, (12 hours i.e.
Release 98 ± 8.5%), and the dendrimer nanoparticle for loading platinum medicine has one significantly to delay the release of platinum medicine
It releases effect: thering is 40% drug to discharge rapidly within first 16 hours, thereafter to 90 hours, drug release rises to 70%.In view of tumour is thin
Drug early period needs to reach peak rapidly when born of the same parents treat, and needs to maintain a treatment concentration for a long time later, and this release is bent in this regard
Line is advantageous.
Embodiment 5
In 24 orifice plates, in the cell transwell for having 1 micrometer Millipore and 0.33 square centimeter of makrolon material
50,000 mouse brain capillary endothelial cells are inoculated with, after undergoing culture in 72 hours, are existed using across transendothelial electrical resistance method measurement resistance
200 ohm-sqs centimetre or more, and can maintain 2 hours or more to think prepared by cell monolayer membrane modle with 24 orifice plate water-heads
Success.Utilize across the blood-brain barrier ability of mouse brain capillary endothelial cell monofilm model in-vitro evaluation nanoparticle.Small interior
Administration targeted nano granule and non-targeted nanoparticle respectively, and inductively coupled plasma atomic emission spectrum is utilized in different time
Method measures platinum constituent content in 24 orifice plates.It was found that compared to not connected target function group group, targeted nano granule group can be obvious
Enhance the ride-through capability (as shown in Figure 3A) to blood-brain barrier.
Embodiment 6
Utilize the ability that blood-brain barrier is crossed in healthy nude mice evaluation nanoparticle body.Every mouse injects 15 mg/kg bodies
The nanoparticle of the modification BODIPY of weight, utilizes isoflurane anesthetized mice after 2 hours, observe nanometer using small animal living body imager
Grain distribution.It was found that compared to not connected target function group group, targeted nano granule group can be remarkably reinforced and wear to blood-brain barrier
More ability (as shown in Figure 3B), the result are consistent in vitro results.
Embodiment 7
After inoculation glioma 16 days, every mouse of tumor-bearing mice injects the modification BODIPY's of 15 mg/kg weight
Nanoparticle utilizes isoflurane anesthetized mice after 2,12 and 24 hours, be distributed using small animal living body imager observation nanoparticle.Hair
Now compared to not connected target function group group, targeting and stored energy to glioma can be remarkably reinforced in targeted nano granule group
Power (as shown in Figure 4).
Embodiment 8
Dendrimer nanoparticle vitro cytotoxicity is investigated using mtt assay.5,000 are inoculated in the every hole of 96 orifice plates
Brain glioblastoma cell-U87 the cell of a source of people is cultivated 24 hours under 37 degree.It is sharp respectively after reaching 60~70% degrees of fusion
With oxaliplatin, non-targeted dendrimer nanoparticle and targeting dendrimer nanoparticle processing.After being persistently incubated for 48 hours
Apoptosis rate is measured using mtt assay.Oxaliplatin, non-targeted dendrimer nanoparticle and targeting dendrimer nanoparticle
IC50 value be respectively ± 1.03 every liter of micromole of 50.56 ± 1.06/43.44 ± 1.09/25.59.It was found that compared to commercially available Austria
The killing to brain glioblastoma cell can be remarkably reinforced in husky benefit platinum raw medicine and not connected target function group group, targeted nano granule group
Ability.
Embodiment 9
Lotus glioma mouse is randomly divided into four groups, every group 8, respectively at inoculation glioma 21,28 and 35 days into
Row administration.Tail vein gives the non-targeted dendrimer nanoparticle of physiological saline, oxaliplatin and targeting dendrimer respectively
Nanoparticle processing, dosage are 5 mg/kg weight.Record mouse survival situation daily, every two days record mouse weights.By
Fig. 6 is it is found that compared to commercially available oxaliplatin raw medicine and not connected target function group group, targeted nano granule group can be remarkably reinforced
To the treatment ability of medicine of glioma.45 days before the treatment simultaneously, its excess-three group is compared, mouse does not occur obvious weight loss, this
Also there is apparent effect to band tumor life quality is improved predictive of targeted nano granule.
Claims (15)
1. a kind of dendrimer nanoparticle of the load platinum medicine of SP peptide modification, it is characterised in that: the nanoparticle is by gathering
L-lysine, SP peptide, polyethylene glycol, DTPA, (1,2- diaminocyclohexane) platinous chloride are made.
2. the dendrimer nanoparticle of the load platinum medicine of SP peptide modification according to claim 1, it is characterised in that: institute
Stating polylysine, SP peptide, polyethylene glycol, DTPA, (1,2- diaminocyclohexane) platinous chloride molar ratio is 1:8:15:20:
The total quality of materials score of 100, metal platinum Zhan is 14.4%.
3. the dendrimer nanoparticle of the load platinum medicine of SP peptide modification according to claim 1, it is characterised in that: institute
Stating polylysine is third generation DGL, possesses 123 primary amino groups, and diameter is 6 nanometers, molecular weight 22000.
4. the dendrimer nanoparticle of the load platinum medicine of SP peptide modification according to claim 1, it is characterised in that: institute
Stating polyethylene glycol is straight chain polyethylene glycol, and end-capping group is azido and NHS active ester, molecular weight 3500.
5. the dendrimer nanoparticle of the load platinum medicine of SP peptide modification according to claim 1, it is characterised in that: institute
Stating DTPA is S-2- (4- isothiocyanic acid benzyl)-diethylenetriamine pentaacetic acid p-SCN-Bn-DTPA.
6. the dendrimer nanoparticle of the load platinum medicine of SP peptide modification according to claim 1, it is characterised in that: institute
SP peptide, sequence RPKPQQFFGLM are stated, and modifies upper 5- hexynic acid in amino terminal.
7. the dendrimer nanoparticle of the load platinum medicine of SP peptide modification according to claim 1, it is characterised in that: institute
Stating the connection type between polylysine, polyethylene glycol, SP peptide and DTPA is covalent key connection.
8. the dendrimer nanoparticle of the load platinum medicine of SP peptide modification according to claim 1, it is characterised in that: institute
State chelation of the connection type between DTPA and platinum medicine between metal-ligand.
9. the dendrimer nanoparticle of the load platinum medicine of SP peptide modification according to claim 1, it is characterised in that: institute
Stating dendrimer nanoparticle partial size is 19.65 ± 4.65 nanometers.
10. the dendrimer nanoparticle of the load platinum medicine of SP peptide modification according to claim 1, it is characterised in that:
Dendrimer nanoparticle potential in pure water is 3.5 ± 0.9 millivolts.
11. a kind of method of the dendrimer nanoparticle for the load platinum medicine for preparing the modification of SP peptide, which is characterized in that it is made
Standby step are as follows:
1) the chelate products Pt-DTPA between DTPA and platinum medicine is prepared；
2) it prepares polylysine-polyethylene glycol covalent linkage object and obtains DGL-PEG；
3) by the 1) chelate products be connected to 2) described in covalent linkage object on, obtain Pt-DTPA-DGL-PEG；
4) by SP peptide be connected to 3) described in DTPA-DGL-PEG on final products.
12. according to method described in claim feature 11, which is characterized in that the chelating between the DTPA and platinum medicine
Method are as follows: in deionized water, molar ratio is added as (1, the 2- diaminocyclohexane) platinous chloride and silver nitrate of 1:1, and
It is stirred 24 hours under the conditions of dark place and 25 degree, by being centrifuged and being filtered to remove silver chlorate, obtains (1,2- diaminocyclohexane) one
Then S-2- (4- isothiocyanic acid benzyl)-diethylenetriamine pentaacetic acid of 0.2 mole is added, at 25 degree in chlorine nitration platinum aqueous solution
Under the conditions of stir 24 hours and obtain the chelate products of DTPA and platinum medicine.
13. according to method described in claim feature 11, which is characterized in that the polylysine-polyethylene glycol is covalent
Connection method are as follows: in the phosphate buffer that pH is 8.0, polylysine, azido and the NHS that molar ratio is 1:15 is added
The straight chain polyethylene glycol of active ester sealing end, is stirred 2 hours at 25 degrees c, and ultrafiltration removes unreacting material and is changed to buffer
The phosphate buffer that pH is 7.0.
14. according to method described in claim feature 11, which is characterized in that described that chelate products are connected to covalent linkage object
Method are as follows: pH be 8.2 4- hydroxyethyl piperazineethanesulfonic acid buffer in, be added molar ratio be 1:20 polylysine-
The chelate of polyethylene glycol attachment and DTPA and platinum medicine stirs 24 hours at 25 degrees c, and is using molecular weight retention
5000 bag filter is dialysed 24 hours in water, and freeze-drying obtains Pt-DTPA-DGL-PEG.
15. according to method described in claim feature 11, which is characterized in that described by SP peptide connection method are as follows: in N, N- bis-
In methylformamide, Pt-DTPA-DGL-PEG, SP peptide, cuprous iodide, the ascorbic acid that molar ratio is 1:5:2.5:5:5 is added
Sodium and n,N-diisopropylethylamine；It stirs 12 hours under 30 degree, and the bag filter for being 5000 using molecular weight retention, exists respectively
It in 10 mMs of disodium ethylene diamine tetra-acetic acid solution and dialyses 24 hours in pure water, freeze-drying obtains final products
SDDPt。
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5871710A (en) * | 1992-09-04 | 1999-02-16 | The General Hospital Corporation | Graft co-polymer adducts of platinum (II) compounds |
| CN103655517A (en) * | 2013-11-19 | 2014-03-26 | 南京医科大学 | Pep-1 peptide modified gliomas targeted nano drug delivery system and preparation method thereof |
-
2017
- 2017-10-29 CN CN201711028961.3A patent/CN109718383A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5871710A (en) * | 1992-09-04 | 1999-02-16 | The General Hospital Corporation | Graft co-polymer adducts of platinum (II) compounds |
| CN103655517A (en) * | 2013-11-19 | 2014-03-26 | 南京医科大学 | Pep-1 peptide modified gliomas targeted nano drug delivery system and preparation method thereof |
Non-Patent Citations (1)
| Title |
|---|
| TAOSUN ET AL.: "Substance P Mediated DGLs Complexing with DACHPt for Targeting Therapy of Glioma", 《APPLIEDMATERIALS&INTERFACES》 * |
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Application publication date: 20190507 |