CN109394695A - A kind of liposome and the preparation method and application thereof that can be supplied oxygen certainly - Google Patents
A kind of liposome and the preparation method and application thereof that can be supplied oxygen certainly Download PDFInfo
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- CN109394695A CN109394695A CN201811399935.6A CN201811399935A CN109394695A CN 109394695 A CN109394695 A CN 109394695A CN 201811399935 A CN201811399935 A CN 201811399935A CN 109394695 A CN109394695 A CN 109394695A
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/127—Liposomes
- A61K9/1277—Processes for preparing; Proliposomes
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K41/00—Medicinal preparations obtained by treating materials with wave energy or particle radiation ; Therapies using these preparations
- A61K41/0057—Photodynamic therapy with a photosensitizer, i.e. agent able to produce reactive oxygen species upon exposure to light or radiation, e.g. UV or visible light; photocleavage of nucleic acids with an agent
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/02—Inorganic compounds
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Abstract
Ammonium hydrogen carbonate (NH can be included from the liposome and its preparation method and application of oxygen supply, the liposome the invention discloses a kind of4HCO3), calper calcium peroxide nanoparticle (CaO2NP) and bodipy class dyestuff (Azo-BODIPY) is complexed in azepine boron fluoride.Wherein, Azo-BODIPY under the light excitation of 622-885nm wavelength, can induce the ammonium bicarbonate breaks down being encapsulated in liposome hydrophilic layer to discharge carbon dioxide as photosensitizer and photothermal reagent, further with CaO2NP reaction generates oxygen and overcomes influence of the weary oxygen microenvironment to therapeutic effect in tumour to ensure that oxygen faster more permanently discharges.Liposome of the present invention can be used as a kind of novel nanometer diagnosis and treatment platform from oxygen supply, can be applied in the efficient optical dynamic therapy of live tumor tissue.
Description
Technical field
The invention belongs to lithotroph technical field of function materials, and in particular to one kind can be from the liposome and its system of oxygen supply
Preparation Method and application.
Background technique
Cancer is the general designation of a major class malignant tumour, and cancer cell increases without limitation, without end in vivo, battalion in consumer
A variety of toxin are released while supporting substance, are one of an important factor for causing human death to cause a variety of diseases.How
Diagnosis and treating cancer as soon as possible reduce the death rate caused by cancer, are always medical domain problem in the urgent need to address.
Currently, traditional anti-cancer therapies mainly have operation excision, chemotherapy and radiation therapy.These treatment sides
Although directly, efficiently, there are clearly disadvantageous for method: operation excision cannot completely remove the cancer cell for spreading to adjacent tissue,
It will cause inevitable deterioration；There is centainly invasive in chemotherapy and radiation therapy, and specific aim is weaker, side effect
Greatly, normal cell can be caused to damage.In this context, optical dynamic therapy causes the concern of scientists, optical dynamic therapy
It is after absorbing specific photon energy using photosensitizer molecule, to generate active oxygen species, destination organization is generated direct or indirect
Damage, to kill a kind for the treatment of means of cancer cell.It, can since it must be triggered under illumination condition by photosensitizer
Realize time and pinpoint accuracy control spatially, at the same optical dynamic therapy have it is invasive it is small, be suitble to participation synergistic treatment etc.
Advantage is gradually accepted by scientists in recent years, has pushed the further development for the treatment of of cancer.
But although optical dynamic therapy has a good application prospect, but still be faced with some difficult and challenge.Light is dynamic
Power therapeutic effect and oxygen concentration in tissue are closely related, and the weary oxygen microenvironment in tumour is inevitable, this will be serious
Singlet oxygen quantum yield is influenced, to limit application of the optical dynamic therapy in actual clinical.In addition, photosensitizer was using
Oxygen, inside tumor decrease in oxygen partial pressure, so as to cause treatment burden are consumed in journey.Therefore, how inside vivo tumor
Weary oxygen microenvironment under, increase oxygen concentration, improving optical dynamic therapy effect to preferably capture cancer becomes light power
The critical issue of therapy field urgent need to resolve.
In conclusion develop it is a kind of it is novel can from oxygen supply, hypotoxicity, good biocompatibility, to can be used for light dynamic
The material of power therapy for treatment of cancer is of great significance.
Summary of the invention
The present invention is intended to provide a kind of liposome that can be supplied oxygen certainly, and open preparation method and application.The liposome can
It is spontaneous under specific photo-excitation conditions, rapidly generate oxygen, overcome the weary oxygen microenvironment in tumour to optical dynamic therapy band
The influence come, has a good application prospect in terms of optical dynamic therapy.
To achieve the goals above, the technical solution adopted in the present invention is as follows: the present invention relates to one kind can be from oxygen supply
Liposome, spontaneous under the photo-excitation conditions of 622-885nm wavelength, rapidly generate oxygen, which includes NH4HCO3、
CaO2Tri- parts NP and Azo-BODIPY, CaO2The whole content of NP is 0.629mg/mL, and the whole content of Azo-BODIPY is
0.156mg/mL；
Wherein, the structure of Azo-BODIPY is as follows:
Wherein, R1, R2=CnH2n+1, n=1,2,3 ... 17；
Wherein, X is halogen.
A kind of preparation method for the liposome that can be supplied oxygen certainly, specific preparation step are as follows:
Step 1: CaO2The preparation of NP:
By CaCl2It is dissolved in ultrapure water, prepared ammonia spirit, PEG 200 and H is added2O2Solution is stirred to react knot
Shu Hou, centrifugation, obtains CaO2NP；
Step 2: the preparation of Azo-BODIPY:
The synthetic route of Azo-BODIPY is as follows:
Wherein, R1,R2=CnH2n+1, n=1,2,3 ... 17；
Wherein, X is halogen；
Wherein, Et=-CH2CH3；
Wherein, NIS=N- N-iodosuccinimide；
The specific synthesis step of Azo-BODIPY are as follows:
A) it is dissolved in stirring and dissolving in ethyl alcohol by 2, addition 1 and prepared NaOH solution are stirred to react, and suction filtration obtains 3；
B) it is dissolved in stirring and dissolving in methanol by 3, nitromethane is added and diethylamine is stirred to react, after reaction stops, being neutralized
Reaction solution to neutrality, extraction, washing organic layer and drying is concentrated under reduced pressure, is recrystallized to give 4；
C) 4 are added in butanol and are dissolved, added ammonium acetate and be stirred to react, after reaction stops, being cooled to room temperature, depressurized dense
Contracting, filtering, is recrystallized to give 5；
D) it is dissolved in stirring and dissolving in methylene chloride by 5, ice-water bath is cooled to 0~5 DEG C, by the methylene chloride containing triethylamine
Solution is added drop-wise in above-mentioned solution, adds the solution of the methylene chloride containing Eorontrifluoride etherate, is moved to and is stirred at room temperature instead
It answers, entire reaction system is in nitrogen protection always, after reaction, is washed, and it is dry, it is concentrated under reduced pressure, column chromatography for separation, weight
Crystallization obtains 6；
E) 6 and NIS are dissolved in CHCl3And CH3In the mixed solution of COOH, it is stirred to react, after reaction, extraction reaction
Liquid takes organic phase column chromatography for separation, obtains Azo-BODIPY；
Step 3: contain CaO2NP, Azo-BODIPY and NH4HCO3Liposome preparation:
DPPC, cholesterol, DSPE-PEG 5000, Azo-BODIPY are weighed, is dissolved in chloroform, CaO is added2The ethyl alcohol of NP
Solution, vacuum distillation remove solvent, obtain rouge layer film, prepared NH is added later4HCO3Solution, after ultrasound, centrifugation
To Target liposomes.
Further, one kind of the present invention can be used for the generation of oxygen in aqueous solution from the liposome of oxygen supply.
Further, one kind of the present invention can be used for the generation of oxygen in cell from the liposome of oxygen supply.
Further, one kind of the present invention can be used for the imaging of tumour cell from the liposome of oxygen supply.
Further, one kind of the present invention can be used in photodynamic therapy from the liposome of oxygen supply.
The beneficial effects of the present invention are:
The invention discloses a kind of liposomes and its preparation method and application that can be supplied oxygen certainly, which includes
NH4HCO3、CaO2Tri- parts NP and Azo-BODIPY, wherein Azo-BODIPY is as photosensitizer and photothermal reagent, specific
Under the excitation of wavelength light, the ammonium bicarbonate breaks down being encapsulated in liposome hydrophilic layer can be induced to discharge carbon dioxide, further
With CaO2NP reaction generates oxygen and overcomes the weary oxygen microenvironment pair in tumour to ensure that oxygen faster more permanently discharges
The influence of therapeutic effect.Liposome described in the invention can be used as a kind of novel nanometer diagnosis and treatment platform from oxygen supply, can be applied to
The efficient optical dynamic therapy of live tumor tissue, has a good application prospect in terms of optical dynamic therapy.
Detailed description of the invention
Fig. 1 is the transmission electron microscope picture for the liposome that the embodiment of the present invention 2 obtains；
Fig. 2 is the variation spirogram of dissolved oxygen in the illumination front and back Liposomal dispersion of the acquisition of the embodiment of the present invention 3；
Fig. 3 is the figure of the absorption peak variable quantity under the normal oxygen that the embodiment of the present invention 4 obtains and hypoxic condition at 400nm；
Fig. 4 is the co-focusing imaging figure under the normal oxygen that the embodiment of the present invention 5 obtains and hypoxic condition in living cells.
Specific embodiment
In order to make those skilled in the art be better understood on technical solution of the present invention, with reference to the accompanying drawing and
Embodiment is further described technical solution of the present invention.
Embodiment 1
The preparation of liposome
Step 1: CaO2The preparation of NP:
(I) 3g CaCl is weighed2In reaction flask, 30mL ultrapure water is added to dissolve；
(II) PEG of 94mL is added dropwise under the mixing speed of 500r/min in the ammonia spirit that 15mL 1M is added
200 solution；
(III) H of 15mL 30% is added2O2Solution (every 20s drips)；
(IV) after being added dropwise, it is stirred to react 1h；
(V) after reaction, suspension is taken to be centrifuged, centrifugal condition are as follows: revolving speed 10000rpm, time 5min, it is isolated
CaO2NP。
Step 2: the preparation of Azo-BODIPY:
The synthetic route of Azo-BODIPY is as follows:
Synthesis step are as follows:
1) 1.10g 2 is weighed in flask, adds 10mL ethyl alcohol stirring and dissolving, 1.03g 1 is added later, in quick stirring bar
The NaOH aqueous solution of 4mL 10% is added drop-wise in flask under part, 30 DEG C are stirred to react 9h, after reaction, filter, filter cake is first
It is washed with water, then is washed with the mixed solution of second alcohol and water, it is dry, solid product 3 is obtained, yield is about 82%；
1H NMR(400MHz,CDCl3) δ (ppm): 8.02 (d, J=7.2Hz, 2H), 7.77 (d, J=15.6Hz, 1H),
7.58 (d, J=8.4Hz, 2H), 7.43 (d, J=15.6Hz, 1H), 6.96 (d, J=8.8Hz 2H), 6.91 (d, J=7.6Hz
2H), 4.08-3.97 (m, 4H), 1.88-1.74 (m, 4H), 1.49-1.25 (m, 12H), 0.91 (t, J=13.6Hz, 6H)
2) weigh 1.67g 3 in flask, be added 10mL methanol stirring and dissolving, be added 1.25g nitromethane and
749.69mg diethylamine is stirred to react 7h；After reaction, with dilute hydrochloric acid neutralization reaction liquid to neutrality, methylene chloride extraction has
Machine layer is successively washed with water and saturated sodium chloride solution, and anhydrous magnesium sulfate is dry, is concentrated under reduced pressure, using dehydrated alcohol/petroleum
Ether mixed solvent is recrystallized to give solid product 4, yield 67%；
1H NMR(400MHz,CDCl3) δ (ppm): 7.88 (d, J=8.0Hz, 2H), 7.17 (d, J=8.0Hz, 2H),
6.90 (d, J=8.3Hz, 2H), 6.83 (d, J=7.6Hz, 2H), 4.85-4.58 (m, 2H), 4.18-4.11 (m, 1H), 4.00
(t, J=12.8Hz, 2H), 3.90 (t, J=12.8Hz, 2H), 3.41-3.28 (m, 2H), 1.82-1.72 (m, 4H), 1.50-
1.28 (m, 12H), 0.88 (t, J=10.8Hz, 6H)
3) 1.29g 4 is weighed in flask, 7mL butanol stirring and dissolving is added, adds 7.41g ammonium acetate solid, is heated up
It is condensed back to 80 DEG C, is stirred to react 12h；After reaction, it is cooled to room temperature to reaction solution, original volume is arrived in reduced pressure
A quarter, filtering, then 5 are recrystallized to give with dehydrated alcohol, yield 32%；
1H NMR(400MHz,CDCl3) δ (ppm): 8.02 (d, J=8.8Hz, 4H), 7.84 (d, J=8.8Hz, 4H),
7.01 (d, J=8.3Hz, 4H), 6.99 (s, 2H), 6.94 (d, J=12.8Hz, 4H), 4.07-3.99 (m, 8H), 1.88-1.77
(m, 8H), 1.55-1.45 (m, 8H), 1.42-1.33 (m, 16H), 0.97-0.89 (t, J=6.8Hz, 12H)
4) 372.00mg 5 is weighed in three mouthfuls of reaction flasks, and the dry methylene chloride stirring and dissolving of 15mL, ice-water bath is added
It is cooling, at 0~5 DEG C, the dry dichloromethane solution of the 4mL that triethylamine is newly steamed containing 489.20mg is added drop-wise to above-mentioned solution
In, then it is slowly added to the solution containing 973.17mg Eorontrifluoride etherate Yu 5mL dry methylene chloride dropwise, after being added dropwise,
It moves to and reaction is stirred at room temperature for 24 hours, entire reaction system is in nitrogen protection always；After reaction, reaction solution successively uses water
Wash, saturated sodium chloride solution is washed, anhydrous magnesium sulfate is dried, after reduced pressure, column chromatography for separation, ethyl alcohol recrystallization, will 6, produce
Rate 70%；
1H NMR(400MHz,CDCl3) δ (ppm): 8.08 (d, J=2.0Hz, 4H), 8.06 (d, J=2.0Hz, 4H),
7.02 (d, J=2.2Hz, 4H), 6.99 (d, J=2.2Hz, 4H), 6.95 (s, 2H), 4.08-4.03 (m, 8H), 1.88-1.79
(m,8H),1.45-1.32(m,24H),0.98-0.96(m,12H).
5) 275.00mg 6 and 76.14mg NIS are weighed in flask, is dissolved in 15mL CHCl3With 5mL CH3COOH
Mixed solution in, be stirred to react 12h at room temperature, after reaction, use CH2Cl2And H2O extracts reaction solution, takes organic phase column layer
Analysis separation, obtains Azo-BODIPY, yield 87%.
1H NMR(400MHz,CDCl3) δ (ppm): 7.83 (d, J=8.8Hz, 4H), 7.67 (d, J=8.9Hz, 4H),
7.01-6.95(m,8H),4.07-3.98(m,8H),1.88-1.78(m,8H),1.55-1.35(m,24H),0.98-0.91(m,
12H).
Step 3: the preparation of liposome:
(I) 5mg DPPC, 1.8mg cholesterol, 3.2mg DSPE-PEG 5000 are weighed in reaction flask；
(II) 1mg Azo-BODIPY is weighed, is dissolved in 2mL chloroform, which is added in above-mentioned reaction flask；
(III) 200 μ L CaO are added2The ethanol solution (10mg/mL) of NP, vacuum distillation remove solvent, it is thin to obtain rouge layer
Film；
(IV) NH of 2.7M is added into rouge layer film4HCO3Solution 10mL, ultrasonic 30s；
(V) suspension is taken to be centrifuged, centrifugal condition are as follows: revolving speed 12000rpm, time 10min, take after centrifugation by 15 DEG C of temperature
The ultrapure water dispersion of 5mL, obtains Target liposomes.
Embodiment 2
The images of transmissive electron microscope of liposome
The shooting of transmission electron microscope is carried out to the liposome for preparing, specific testing procedure is: taking the 20 μ L concentration to be
The sample solution of 0.2mg/mL drips on copper mesh, and pattern test is carried out after sample drying.Its image is as shown in Figure 1, from figure
As can be seen that the dispersibility of liposome in aqueous solution is preferably, particle size is about 80nm, is conducive to enter in cell, into
One step provides possibility for the oxygen supply of organism.
Embodiment 3
The test of dissolved oxygen variable quantity before and after illumination
The Liposomal dispersion of 80 μ g/mL is prepared, solvent is ultrapure water.After 20min, on the basis of original device, use
730nm laser irradiation tests the variable quantity of dissolved oxygen in dispersion liquid.The image of dissolved oxygen variable quantity is as schemed before and after the illumination obtained
Shown in 2, it can be seen from the figure that oxygen variable quantity is unobvious in solution before illumination, after 730nm laser irradiation, a timing
In, oxygen content increases obvious accelerate in solution.The experimental results showed that synthesized liposome is excited in the light of specific wavelength
Under the conditions of, the generation of oxygen can be accelerated, therefore, optical dynamic therapy can be performed well in.
Embodiment 4
In the experiment that singlet oxygen generates, using 3- diphenyl isobenzofuran (DPBF) as indicator.By DPBF
Dimethyl sulfoxide (DMSO) solution of (200 μM) and liposome to be measured (80 μ g/mL) mixing, in 730nm, 50mW/cm2Illumination
It penetrates down, by variable quantity of the observation DPBF in the absorption peak unit time at 400nm, to judge the generation of singlet oxygen,
And then judge liposome from the case where oxygen supply.Experiment is divided into normal oxygen group and weary oxygen group, and experimental result is as shown in figure 3, can from figure
To find out, under specific light irradiation, the variable quantity in the absorption peak unit time at normal oxygen group and weary oxygen group 400nm almost phase
Together, illustrate that liposome is good from the ability of oxygen supply under hypoxic condition.Therefore, which can perform well in light power and control
It treats.
Embodiment 5
Liposome is applied to living cells imaging experiment
With contain liposome (80 μ g/mL) DMEM culture solution culture human body cervical carcinoma cell (HeLa), in 37 DEG C of conditions
Under contain 5%CO2Air in be incubated for 2 hours after, add 2,7- dichloro-dihydro for two acetic acid of fluorescein (DCFH-DA) (1 μ
M), continue to cultivate 15min, imaging experiment is used for after the washing of PBS buffer solution, experiment to be divided into normal oxygen group and weary oxygen group.It can from Fig. 4
To find out, illumination (730nm, 50mW/cm2) after 6min, active oxygen species (ROS) content of weary oxygen group obviously increases, and continues
Time is longer, and increasing speed for the ROS content of normal oxygen group is then more slow.The experimental results showed that the liposome is in weary oxygen item
Under part, under specific wavelength illumination excitation, ROS can be generated well, can be applied to optical dynamic therapy.
Basic principles and main features and advantage of the invention have been shown and described above.But the foregoing is merely this hairs
Bright specific embodiment, technical characteristic of the invention are not limited thereto, and any those skilled in the art is not departing from this hair
The other embodiments obtained under bright technical solution should all cover within the scope of the patent of the present invention.
Claims (6)
1. one kind can from oxygen supply liposome, which is characterized in that the liposome under the photo-excitation conditions of 622-885nm wavelength from
Hair rapidly generates oxygen, includes NH in the liposome4HCO3、CaO2Tri- parts NP and Azo-BODIPY；
Wherein, the structure of Azo-BODIPY is as follows:
Wherein, R1, R2=CnH2n+1, n=1,2,3 ... 17；
Wherein, X is halogen.
2. one kind as described in claim 1 can be from the preparation method of the liposome of oxygen supply, which is characterized in that specific preparation step
Are as follows:
Step 1: CaO2The preparation of NP:
By CaCl2It is dissolved in ultrapure water, prepared ammonia spirit, PEG 200 and H is added2O2Solution, after being stirred to react,
Centrifugation, obtains CaO2NP；
Step 2: the preparation of Azo-BODIPY:
The synthetic route of Azo-BODIPY is as follows:
Wherein, Et=-CH2CH3；
Wherein, NIS=N- N-iodosuccinimide；
The specific synthesis step of Azo-BODIPY are as follows:
A) it is dissolved in stirring and dissolving in ethyl alcohol by 2, addition 1 and prepared NaOH solution are stirred to react, and suction filtration obtains 3；
B) it is dissolved in stirring and dissolving in methanol by 3, nitromethane is added and diethylamine is stirred to react, after reaction stops, neutralization reaction
Liquid to neutrality, extraction, washing organic layer and drying is concentrated under reduced pressure, is recrystallized to give 4；
C) 4 are added in butanol and are dissolved, added ammonium acetate and be stirred to react, after reaction stops, being cooled to room temperature, is concentrated under reduced pressure,
Filtering, is recrystallized to give 5；
D) it is dissolved in stirring and dissolving in methylene chloride by 5, ice-water bath is cooled to 0~5 DEG C, by the dichloromethane solution containing triethylamine
It is added drop-wise in above-mentioned solution, adds the dichloromethane solution containing Eorontrifluoride etherate, move to and reaction is stirred at room temperature, entirely
Reaction system is in nitrogen protection always, after reaction, is washed, dry, is concentrated under reduced pressure, column chromatography for separation recrystallizes
To 6；
E) 6 and NIS are dissolved in CHCl3And CH3It in the mixed solution of COOH, is stirred to react, after reaction, extracts reaction solution, take
Organic phase column chromatography for separation, obtains Azo-BODIPY；
Step 3: contain CaO2NP, Azo-BODIPY and NH4HCO3Liposome preparation:
It weighs DPPC, cholesterol, DSPE-PEG 5000 and Azo-BODIPY to be dissolved in chloroform, CaO is added2The ethanol solution of NP,
Vacuum distillation removes solvent, obtains rouge layer film, prepared NH is added later4HCO3Solution obtains target after ultrasound, centrifugation
Liposome.
3. as one kind of any of claims 1-2 can produce in aqueous solution the application of oxygen from the liposome of oxygen supply.
4. as one kind of any of claims 1-2 can produce the application of oxygen from the liposome of oxygen supply in cell.
5. as one kind of any of claims 1-2 can be from application of the liposome supplied oxygen in tumour cell imaging.
6. as one kind of any of claims 1-2 can be from liposome the answering in the optical dynamic therapy of tumour of oxygen supply
With.
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| CN110227065A (en) * | 2019-03-22 | 2019-09-13 | 中山大学孙逸仙纪念医院 | Folate-targeted carries NaHCO3Liposome and its application in terms of enhancing immunotherapy of tumors effect |
| CN110950899A (en) * | 2019-12-17 | 2020-04-03 | 大连理工大学 | Photo-thermal reagent with ultra-efficient energy barrier-free rotor for photo-thermal therapy and preparation method and application thereof |
| CN111643482A (en) * | 2020-07-28 | 2020-09-11 | 南京邮电大学 | Nano particles capable of releasing hydrogen sulfide under hypoxic condition, and preparation method and application thereof |
| CN111777711A (en) * | 2020-07-29 | 2020-10-16 | 南京邮电大学 | Polymer for photo-thermal controlled release of hydrogen sulfide and preparation method and application thereof |
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| CN110227065B (en) * | 2019-03-22 | 2021-07-27 | 中山大学孙逸仙纪念医院 | Folic acid targeting NaHCO3Liposome and application thereof in enhancing tumor immunotherapy effect |
| CN110950899A (en) * | 2019-12-17 | 2020-04-03 | 大连理工大学 | Photo-thermal reagent with ultra-efficient energy barrier-free rotor for photo-thermal therapy and preparation method and application thereof |
| CN110950899B (en) * | 2019-12-17 | 2021-03-26 | 大连理工大学 | Photo-thermal reagent with ultra-efficient energy barrier-free rotor for photo-thermal therapy and preparation method and application thereof |
| CN111643482A (en) * | 2020-07-28 | 2020-09-11 | 南京邮电大学 | Nano particles capable of releasing hydrogen sulfide under hypoxic condition, and preparation method and application thereof |
| CN111777711A (en) * | 2020-07-29 | 2020-10-16 | 南京邮电大学 | Polymer for photo-thermal controlled release of hydrogen sulfide and preparation method and application thereof |
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