CN103751811A - Diagnosis and treatment integrated bovine serum albumin anticancer nanoparticle and preparation method thereof - Google Patents
Diagnosis and treatment integrated bovine serum albumin anticancer nanoparticle and preparation method thereof Download PDFInfo
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Abstract
The invention relates to a diagnosis and treatment integrated bovine serum albumin anticancer nanoparticle and a preparation method thereof. The particle comprises bovine serum albumin, rare earth metal ion and anticancer drug, wherein the rare earth metal ion and bovine serum albumin form nanoparticle with imaging function through coordination, the anticancer drug is immobilized on the nanoparticle and is bound to the rare earth metal ion coordination site that interacts with bovine serum albumin. Compared with the prior art, according to the invention, bovine serum albumin solution with certain concentration and rare earth metal ion solution form a compound particle through coordination. The structure and morphology of the compound particle can be regulated by changing the concentration of the two solutions to improve the particle performance. In addition, an element (rare earth metal ion) with MRI effect is introduced at the coordination site of the system. Compared with the traditional nanoparticle, the preparation method has the advantages of flexible and easily controllable regulation, and good repetitiveness, and the obtained nanoparticle has excellent properties.
Description
Technical field
The invention belongs to high molecular nanometer biological medicine Material Field, especially relate to the integrated bovine serum albumin anticancer nano of a kind of diagnosis and treatment particle and preparation method thereof.
Background technology
Cancer is disease not normal by the mechanism of controlling growth and proliferation of cell and that cause, and the mankind's health in serious harm.Cancerous cell except grow out of control, normal structure arround also can local invading, even transfers to other parts of health via body-internal-circulation system or lymphsystem.According to statistics, the at present annual whole world has 1,200 ten thousand people to be diagnosed as cancer, 7600000 people die from cancer, and the sickness rate of cancer is also in continuous increase, will there be 2,600 ten thousand newly-increased cases in the expectation the year two thousand thirty whole world, death toll reaches 1,700 ten thousand people, and wherein great majority will occur in the developing country of middle and low income.In some western countries, U.S. for example, 25% of current all death tolls are because of cancer mortality, and approximately have every year 0.5% population to diagnose out cancer.At China's tumor incidence, be about 2,00/,100,000 people, more than annual new cases reach 2,200,000 people, more than controlling patient 6,000,000 people.Due to its high fatality rate and higher sickness rate, cancer has not only become the No.1 killer who threatens China's people's life, but also has taken national a large amount of medical resource.
Treatment of cancer means mainly contain chemotherapy, excision, radiotherapy, monoclonal gene therapy etc.Radiotherapy and monoclonal gene therapy are under test at present, exist not predictable risk.Excision and chemotherapy are the main method of current treatment of cancer, and chemotherapy is significant for the treatment of cancer and the transfer of control cancerous cell, yet chemotherapy is also faced with many still an open questions.As large in drug side effect, dissolubility is low, circulation time is short, low etc. without targeting, utilization ratio of drug.For this reason, development of new multifunctional nano drug delivery system is the main path that solves problems, has been subject at present numerous scholars' extensive concern.
Nanoparticle is a common Nano medication transmission system, how to allow the discharging at diseased region of drug selectivity, has again the several functions such as diagnosis, imaging simultaneously, is material scholar, cures the direction that scholars make joint efforts.
Chinese patent CN 102512687A has announced a kind of pH response anti-cancer drug preparation and preparation method thereof.In course of reaction, using BSA as the carrier of cancer therapy drug, using metallic zinc ion as intermediate, adopt desolventizing legal system for anticancer nano medicine carrying granule, utilize the sour environment of tumor locus, reach targeted drug and discharge.But contrast agent is not introduced in this invention, there is no the function of diagnosing tumor, do not realize diagnosis and treatment integrated.
The present invention utilizes BSA as pharmaceutical carrier, introduces innovatively the rare earth metal with radiography function, not only realizes the slow release of medicine within the scope of the small acid pH of tumor environment, and has realized the function of quick diagnosis, has reached the integrated object of diagnosis and treatment.
Summary of the invention
Object of the present invention is exactly to provide a kind of integrated bovine serum albumin anticancer nano of diagnosis and treatment particle based on pH response and preparation method thereof in order to overcome the defect of above-mentioned prior art existence, it is low that this nanoparticle can effectively solve in prior art when nanometer polymer is as pharmaceutical carrier carrying drug ratio, medicine is revealed, cancer diagnosis and treatment cannot be organically combined, the problem such as tracing observation medication effect effectively clearly, and can the prolong drug half-life in vivo, improve drug disposition distribution situation, reducing medicine is removed by kidney or liver, protection medicine is avoided degraded.
Object of the present invention can be achieved through the following technical solutions:
The integrated bovine serum albumin anticancer nano of diagnosis and treatment particle, comprise bovine serum albumin, rare earth ion and active anticancer medicine, described rare earth ion and bovine serum albumin form the nanoparticle with radiography function by coordination, described active anticancer medicine is fixed on nanoparticle, and be connected to the interactional rare earth ion coordination site of bovine serum albumin on.
The integrated bovine serum albumin anticancer nano of described diagnosis and treatment particle is the integrated bovine serum albumin anticancer nano of the diagnosis and treatment particle with pH response, and particle diameter is 4～200nm.
Described bovine serum albumin contains 583 amino acid residues, and molecular weight is 66.430kDa, and isoelectric point, IP is 4.7.
Described active anticancer medicine has the structure of similar Herba Alii fistulosi quinones.
A kind of containing in following structure of described active anticancer pharmaceutical pack: rice holder Herba Alii fistulosi ketone, daunorubicin hydrochloride, doxorubicin hydrochloride, idarubicin hydrochloride, Farmorubine Hydrochloride, aclarubicin hydrochloride, zorubicin hydrochloride, pirarubicin, esorubicin, carubicin, Nemorubicin, valrubicin, detorubicin, rodorubicin or medorubicin.
The preparation method of the integrated bovine serum albumin anticancer nano of diagnosis and treatment particle, comprises the following steps:
(1) in bovine serum albumen solution, add the solution that contains rare earth ion, stirring reaction, makes bovine serum albumin generation degeneration;
(2) in step (1) gained system, add alkali liquor regulator solution PH, make it to become clarification;
(3) step (2) gained system is purified, remove rare earth ion and the impurity of not having an effect, obtain nanoparticle;
(4) carrying medicament: under neutrallty condition, by step (3) gained nanoparticle formation solution soluble in water, and add active anticancer medicine, antibacterial activity medicine and nanoparticle react, be fixed on the inside of nanoparticle, and be connected to the interactional rare earth ion coordination site of bovine serum albumin on;
(5) purify, remove active anticancer medicine free in step (4) system and unnecessary impurity, lyophilizing obtains integrated bovine serum albumin anticancer nano particle.
In bovine serum albumen solution described in step (1), the solubility of bovine serum albumin is 0.5mg/ml～50mg/ml.
In step (1) gained system, the molar concentration rate of rare earth ion and bovine serum albumin is 12: 1～1: 5.
In step (2) gained system, the molar concentration rate of alkali liquor and bovine serum albumin is 1: 50～1: 12.
The active anticancer medicine adding in step (4) and the mass ratio of bovine serum albumin are 1: 5～3: 10.
Described alkali liquor is ammonia or sodium hydroxide solution.
Compared with prior art, the present invention has the following advantages and beneficial effect:
(1) the invention provides the method for the integrated nanometer system of a kind of easy structure diagnosis and treatment, select and there is certain density bovine serum albumen solution and rare earth ion solution, by coordination, form compound particle.Wherein, by changing the concentration of two kinds of solution, can regulate and control structure and the form of compound particle, improve the performance of particle.In addition, on the coordination site in system, introduced the element (rare earth ion) with MRI effect.Compare with traditional nanoparticle, this method has control methods easily control flexibly, and repeatability is strong, the advantages such as resulting nanoparticle superior performance.
(2) nanoparticle preparing has the stability of height, good biocompatibility and degradability.
(3) on the coordination site of rare earth ion, access medicine, can rapid delivery of pharmaceuticals under acid tumor environment, effectively improve medicine tumor locus accumulation may with quantity.
(4) nanoparticle medicine carrying is combined effectively with nuclear magnetic resonance, can when improving accuracy rate of diagnosis, disease be treated, realize diagnosis and treatment integrated, the diagnosis of tumor and treatment are had to important meaning.
Accompanying drawing explanation
Fig. 1 be in embodiment 1 load the medicine carrying protein nano particle transmission electron microscope picture of active anticancer medicine;
Fig. 2 is bovine serum albumin and rare earth ion gadolinium compound aqueous solution particle size distribution figure in embodiment 1;
Fig. 3 be in embodiment 1 load bovine serum albumin and the compound water-soluble particle size distribution figure of rare earth ion gadolinium of active anticancer medicine;
In Fig. 4 embodiment 1, be pure medicine, not carrying medicament nanoparticle, load the cytotoxicity figure of nanoparticle of medicine;
Fig. 5 protein nano granule drug release studies curve under different pH of medicine that has been load in embodiment 1.
The specific embodiment
Below in conjunction with the drawings and specific embodiments, the present invention is described in detail.
In the process of preparation, add respectively 15ml intermediate water solution that 750mg, 150mg, 75mg, 15mg bovine serum albumin be made in the beaker of 4 100ml, then the Gadolinium trichloride solution that adds respectively 0.2mmol at the uniform velocity stirs 3min on magnetic stirring apparatus, and reaction temperature is 25 ℃ of room temperature.Then add respectively 50ul, 1molL
-1sodium hydrate aqueous solution, continue to stir 2 hours, solution forms stable system, separated through the dialysis of 12 hours and high speed centrifugation, can obtain the nanoparticle of uniform particle diameter, as shown in Figure 2, particle diameter is in 10nm left and right.Then lyophilizing is got 10mg and is placed in centrifuge tube and forms aqueous solution separately, adds cancer therapy drug 2mg, dialyses and removes the medicine not carrying in 6 hours, the nanoparticle of medicine that obtained load, and as shown in Figure 1, Figure 3, size is more even.Respectively get 5mg nanoparticle drugs release behavior under different pH, as shown in Figure 5, anticancer nano particle under subacidity tumor environment medicine release behavior with under neutrallty condition, there is larger difference, prove and there is pH sensitivity tumor-targeting.Take 5mg cancer therapy drug protein nano particle and show that by Fig. 4 Concentraton gradient (drug level, BSA-Gd concentration, BSA-Gd-dox concentration) carries out MTT cytotoxicity experiment, result as shown in Figure 4, is studied the toxicity of synthetic cancer therapy drug protein nano granule.
Embodiment 2
In the process of preparation, add 15ml intermediate water solution that 150mg bovine serum albumin is made in the beaker of 4 100ml, then add respectively 0.2mmol, 0.15mmol, 0.1mmol, the Gadolinium trichloride solution of 0.05mmol, on magnetic stirring apparatus, at the uniform velocity stir 3min, reaction temperature is 25 ℃ of room temperature.Then add respectively 50ul, 1molL
-1sodium hydrate aqueous solution, continue to stir 2 hours, solution forms stable system, separated through the dialysis of 12 hours and high speed centrifugation, can obtain the nanoparticle of uniform particle diameter.Then lyophilizing is got 10mg and is placed in centrifuge tube and forms aqueous solution separately, adds cancer therapy drug 2mg, dialyses and removes the medicine not carrying in 6 hours, the nanoparticle of medicine that obtained load.
Embodiment 3
In the process of preparation, add separately 15ml intermediate water solution that 150mg bovine serum albumin is made in the beaker of 3 100ml, then add respectively the Gadolinium trichloride solution of 0.15mmol, on magnetic stirring apparatus, at the uniform velocity stir 3min, reaction temperature is 25 ℃ of room temperature.Then add respectively 50ul, 40ul, 30ul 1mol L
-1sodium hydrate aqueous solution, continue to stir 2 hours, solution forms stable system, separated through the dialysis of 12 hours and high speed centrifugation, can obtain nanoparticle three Gadolinia .s of uniform particle diameter.Then lyophilizing is got 10mg and is placed in centrifuge tube and forms aqueous solution separately, adds cancer therapy drug 2mg, dialyses and removes the medicine not carrying in 6 hours, the nanoparticle of cancer therapy drug that obtained load.
Embodiment 4
In the process of preparation, add 15ml intermediate water solution that 150mg bovine serum albumin is made in the beaker of 1 100ml, then add respectively the Gadolinium trichloride solution of 0.15mmol, on magnetic stirring apparatus, at the uniform velocity stir 3min, reaction temperature is 25 ℃ of room temperature.Then add 40ul 1mol L
-1sodium hydrate aqueous solution, continue to stir 2 hours, solution forms stable system, separated through the dialysis of 12 hours and high speed centrifugation, can obtain nanoparticle three Gadolinia .s of uniform particle diameter.Then lyophilizing is got 10mg and is placed in centrifuge tube and forms aqueous solution separately, adds respectively cancer therapy drug 1.5mg, 2mg, 2.5mg, 3mg, dialyses and removes the cancer therapy drug not carrying in 6 hours, the nanoparticle of cancer therapy drug that obtained load.
The integrated bovine serum albumin anticancer nano of the diagnosis and treatment particle with pH response, comprise bovine serum albumin, rare earth ion and active anticancer medicine, bovine serum albumin contains 583 amino acid residues, molecular weight is 66.430kDa, isoelectric point, IP is 4.7, rare earth ion and bovine serum albumin form the nanoparticle with radiography function by coordination, active anticancer medicine is fixed on nanoparticle, and be connected to the interactional rare earth ion coordination site of bovine serum albumin on.Particle diameter is 4～200nm.
Active anticancer medicine has the structure of similar Herba Alii fistulosi quinones.Active anticancer pharmaceutical pack is containing rice holder Herba Alii fistulosi ketone.
The preparation method of the integrated bovine serum albumin anticancer nano of diagnosis and treatment particle, comprises the following steps:
(1) in bovine serum albumen solution, add the solution that contains rare earth ion, stirring reaction, make bovine serum albumin generation degeneration, in bovine serum albumen solution, the solubility of bovine serum albumin is 0.5mg/ml, and the molar concentration rate of rare earth ion and bovine serum albumin is 12: 1;
(2) in step (1) gained system, add alkali liquor regulator solution pH, alkali liquor (ammonia) is to make it to become clarification at 1: 50 with the molar concentration rate of bovine serum albumin;
(3) step (2) gained system is purified, remove rare earth ion and the impurity of not having an effect, obtain nanoparticle;
(4) carrying medicament: under neutrallty condition, by step (3) gained nanoparticle formation solution soluble in water, and add active anticancer medicine, the active anticancer medicine adding and the mass ratio of bovine serum albumin are 1: 5, antibacterial activity medicine and nanoparticle react, be fixed on the inside of nanoparticle, and be connected to the interactional rare earth ion coordination site of bovine serum albumin on;
(5) purify, remove active anticancer medicine free in step (4) system and unnecessary impurity, lyophilizing obtains integrated bovine serum albumin anticancer nano particle.
Embodiment 6
The integrated bovine serum albumin anticancer nano of the diagnosis and treatment particle with pH response, comprise bovine serum albumin, rare earth ion and active anticancer medicine, bovine serum albumin contains 583 amino acid residues, molecular weight is 66.430kDa, isoelectric point, IP is 4.7, rare earth ion and bovine serum albumin form the nanoparticle with radiography function by coordination, active anticancer medicine is fixed on nanoparticle, and be connected to the interactional rare earth ion coordination site of bovine serum albumin on, particle diameter is 4～200nm.
Active anticancer medicine has the structure of similar Herba Alii fistulosi quinones.A kind of containing in following structure of active anticancer pharmaceutical pack: daunorubicin hydrochloride, doxorubicin hydrochloride, idarubicin hydrochloride or Farmorubine Hydrochloride.
The preparation method of the integrated bovine serum albumin anticancer nano of diagnosis and treatment particle, comprises the following steps:
(1) in bovine serum albumen solution, add the solution that contains rare earth ion, stirring reaction, make bovine serum albumin generation degeneration, in bovine serum albumen solution, the solubility of bovine serum albumin is 5mg/ml, and the molar concentration rate of rare earth ion and bovine serum albumin is 1: 1;
(2) in step (1) gained system, add alkali liquor regulator solution pH, alkali liquor (ammonia) is to make it to become clarification at 1: 20 with the molar concentration rate of bovine serum albumin;
(3) step (2) gained system is purified, remove rare earth ion and the impurity of not having an effect, obtain nanoparticle;
(4) carrying medicament: under neutrallty condition, by step (3) gained nanoparticle formation solution soluble in water, and add active anticancer medicine, the active anticancer medicine adding and the mass ratio of bovine serum albumin are 1: 4, antibacterial activity medicine and nanoparticle react, be fixed on the inside of nanoparticle, and be connected to the interactional rare earth ion coordination site of bovine serum albumin on;
(5) purify, remove active anticancer medicine free in step (4) system and unnecessary impurity, lyophilizing obtains integrated bovine serum albumin anticancer nano particle.
Embodiment 7
The integrated bovine serum albumin anticancer nano of the diagnosis and treatment particle with pH response, comprise bovine serum albumin, rare earth ion and active anticancer medicine, bovine serum albumin contains 583 amino acid residues, molecular weight is 66.430kDa, isoelectric point, IP is 4.7, rare earth ion and bovine serum albumin form the nanoparticle with radiography function by coordination, active anticancer medicine is fixed on nanoparticle, and be connected to the interactional rare earth ion coordination site of bovine serum albumin on, particle diameter is 4～200nm.
Active anticancer medicine has the structure of similar Herba Alii fistulosi quinones.A kind of containing in following structure of active anticancer pharmaceutical pack: aclarubicin hydrochloride, zorubicin hydrochloride, pirarubicin, esorubicin, carubicin, Nemorubicin, valrubicin, detorubicin, rodorubicin or medorubicin.
The preparation method of the integrated bovine serum albumin anticancer nano of diagnosis and treatment particle, comprises the following steps:
(1) in bovine serum albumen solution, add the solution that contains rare earth ion, stirring reaction, make bovine serum albumin generation degeneration, in bovine serum albumen solution, the solubility of bovine serum albumin is 50mg/ml, and the molar concentration rate of rare earth ion and bovine serum albumin is 1: 5;
(2) in step (1) gained system, add alkali liquor regulator solution pH, alkali liquor (sodium hydroxide solution) is to make it to become clarification at 1: 12 with the molar concentration rate of bovine serum albumin;
(3) step (2) gained system is purified, remove rare earth ion and the impurity of not having an effect, obtain nanoparticle;
(4) carrying medicament: under neutrallty condition, by step (3) gained nanoparticle formation solution soluble in water, and add active anticancer medicine, the active anticancer medicine adding and the mass ratio of bovine serum albumin are 3: 10, antibacterial activity medicine and nanoparticle react, be fixed on the inside of nanoparticle, and be connected to the interactional rare earth ion coordination site of bovine serum albumin on;
(5) purify, remove active anticancer medicine free in step (4) system and unnecessary impurity, lyophilizing obtains integrated bovine serum albumin anticancer nano particle.
Claims (10)
1. the integrated bovine serum albumin anticancer nano of diagnosis and treatment particle, it is characterized in that, comprise bovine serum albumin, rare earth ion and active anticancer medicine, described rare earth ion and bovine serum albumin form the nanoparticle with radiography function by coordination, described active anticancer medicine is fixed on nanoparticle, and be connected to the interactional rare earth ion coordination site of bovine serum albumin on.
2. the integrated bovine serum albumin anticancer nano of diagnosis and treatment according to claim 1 particle, it is characterized in that, the integrated bovine serum albumin anticancer nano of described diagnosis and treatment particle is the integrated bovine serum albumin anticancer nano of the diagnosis and treatment particle with pH response, and particle diameter is 4～200nm.
3. the integrated bovine serum albumin anticancer nano of diagnosis and treatment according to claim 1 particle, is characterized in that, described bovine serum albumin contains 583 amino acid residues, and molecular weight is 66.430kDa, and isoelectric point, IP is 4.7.
4. the integrated bovine serum albumin anticancer nano of diagnosis and treatment according to claim 1 particle, is characterized in that, described active anticancer medicine has the structure of similar Herba Alii fistulosi quinones.
5. the integrated bovine serum albumin anticancer nano of diagnosis and treatment according to claim 4 particle, it is characterized in that a kind of containing in following structure of described active anticancer pharmaceutical pack: rice holder Herba Alii fistulosi ketone, daunorubicin hydrochloride, doxorubicin hydrochloride, idarubicin hydrochloride, Farmorubine Hydrochloride, aclarubicin hydrochloride, zorubicin hydrochloride, pirarubicin, esorubicin, carubicin, Nemorubicin, valrubicin, detorubicin, rodorubicin or medorubicin.
6. the preparation method of the integrated bovine serum albumin anticancer nano of the diagnosis and treatment as described in any one in claim 1～5 particle, is characterized in that, comprises the following steps:
(1) in bovine serum albumen solution, add the solution that contains rare earth ion, stirring reaction, makes bovine serum albumin generation degeneration;
(2) in step (1) gained system, add alkali liquor regulator solution pH, make it to become clarification;
(3) step (2) gained system is purified, remove rare earth ion and the impurity of not having an effect, obtain nanoparticle;
(4) carrying medicament: under neutrallty condition, by step (3) gained nanoparticle formation solution soluble in water, and add active anticancer medicine, antibacterial activity medicine and nanoparticle react, be fixed on the inside of nanoparticle, and be connected to the interactional rare earth ion coordination site of bovine serum albumin on;
(5) purify, remove active anticancer medicine free in step (4) system and unnecessary impurity, lyophilizing obtains integrated bovine serum albumin anticancer nano particle.
7. the preparation method of the integrated bovine serum albumin anticancer nano of diagnosis and treatment according to claim 6 particle, is characterized in that, in the described bovine serum albumen solution of step (1), the solubility of bovine serum albumin is 0.5mg/ml～50mg/ml.
8. the preparation method of the integrated bovine serum albumin anticancer nano of diagnosis and treatment according to claim 6 particle, is characterized in that, in step (1) gained system, the molar concentration rate of rare earth ion and bovine serum albumin is 12: 1～1: 5.
9. the preparation method of the integrated bovine serum albumin anticancer nano of diagnosis and treatment according to claim 6 particle, is characterized in that, in step (2) gained system, the molar concentration rate of alkali liquor and bovine serum albumin is 1: 50～1: 12.
10. the preparation method of the integrated bovine serum albumin anticancer nano of diagnosis and treatment according to claim 6 particle, is characterized in that, the active anticancer medicine adding in step (4) and the mass ratio of bovine serum albumin are 1: 5～3: 10.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105435248A (en) * | 2015-12-09 | 2016-03-30 | 哈尔滨工业大学 | Multi-functional bismuth selenide nanocomposite and preparation method and application thereof |
| CN107812200A (en) * | 2017-10-21 | 2018-03-20 | 天津大学 | BSA-gadolinium ionic complex-coated hollow gold nanosheet and preparation method thereof |
| WO2023012221A1 (en) * | 2021-08-03 | 2023-02-09 | Helmholtz Zentrum München - Deutsches Forschungszentrum für Gesundheit und Umwelt (GmbH) | Proteins identified from barn dust extract for the prevention and treatment of diseases |
| CN117417397A (en) * | 2023-10-17 | 2024-01-19 | 浙江亚瑟医药有限公司 | Idarubicin hydrochloride crystal form and preparation method thereof |
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| CN102512687A (en) * | 2011-12-14 | 2012-06-27 | 上海交通大学 | PH-response anti-cancer medicinal preparation and preparation method thereof |
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2014
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| CN102512687A (en) * | 2011-12-14 | 2012-06-27 | 上海交通大学 | PH-response anti-cancer medicinal preparation and preparation method thereof |
Non-Patent Citations (2)
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| MAURO COMES FRANCHINI ET AL.: "Bovine Serum Albumin-Based Magnetic Nanocarrier for MRI Diagnosis and Hyperthermic Therapy: A Potential Theranostic Approach Against Cancer", 《SMALL》 * |
| TAVAREKERE N. NAGARAJA ET AL.: "Application of arsenazo III in the preparation and characterization of an albumin-linked, gadolinium-based macromolecular magnetic resonance contrast agent", 《JOURNAL OF NEUROSCIENCE METHODS》 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105435248A (en) * | 2015-12-09 | 2016-03-30 | 哈尔滨工业大学 | Multi-functional bismuth selenide nanocomposite and preparation method and application thereof |
| CN105435248B (en) * | 2015-12-09 | 2018-04-27 | 哈尔滨工业大学 | A kind of multi-functional bismuth selenide nano-complex, its preparation method and application |
| CN107812200A (en) * | 2017-10-21 | 2018-03-20 | 天津大学 | BSA-gadolinium ionic complex-coated hollow gold nanosheet and preparation method thereof |
| CN107812200B (en) * | 2017-10-21 | 2020-11-06 | 天津大学 | BSA-gadolinium ionic complex-coated hollow gold nanosheet and preparation method thereof |
| WO2023012221A1 (en) * | 2021-08-03 | 2023-02-09 | Helmholtz Zentrum München - Deutsches Forschungszentrum für Gesundheit und Umwelt (GmbH) | Proteins identified from barn dust extract for the prevention and treatment of diseases |
| CN117417397A (en) * | 2023-10-17 | 2024-01-19 | 浙江亚瑟医药有限公司 | Idarubicin hydrochloride crystal form and preparation method thereof |
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Application publication date: 20140430 |