CN107929316B - Iridium nano composite medicine and preparation method thereof - Google Patents
Iridium nano composite medicine and preparation method thereof Download PDFInfo
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- CN107929316B CN107929316B CN201711203328.3A CN201711203328A CN107929316B CN 107929316 B CN107929316 B CN 107929316B CN 201711203328 A CN201711203328 A CN 201711203328A CN 107929316 B CN107929316 B CN 107929316B
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/24—Heavy metals; Compounds thereof
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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
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
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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
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
Abstract
The invention relates to an iridium nanometer intelligent composite carrier and a preparation method thereof, belonging to the field of biological medicine. The invention adopts a high-temperature solution method to compound chitosan oligosaccharide, gamma-polyglutamic acid and iridium nano particles, the three substances generate particles below 100nm after cross-linking reaction, the method is simple to operate, the obtained iridium nano targeting compound carrier has a typical core-shell structure, the nanocrystal has targeting and slow-release capabilities by changing the pH value, and has more clinical and practical application prospects compared with a single iridium nano particle.
Description
Technical Field
The invention belongs to the field of biological medicines, and particularly relates to an iridium nanometer intelligent composite medicine and a preparation method thereof.
Background
The mode of drug delivery has a crucial impact on the therapeutic efficacy of cancer, with tumor-targeted drug delivery being a major challenge. As the research of nanotechnology in the biomedical field is deepened, magnetic nanomaterials are receiving much attention. The noble metal platinum has been applied to over 50 percent of cancer chemotherapy, and the potential of other noble metals such as iridium can provide a new targeted drug, attack cancer cells in a completely new way, can be safely used, has little side effect, and can be combined with various targets in the cells, such as DNA, RNA, protein and the like. However, the iridium nanoparticles have unsatisfactory biocompatibility, and the aggregation among the particles causes the particle size to be increased and the stability to be poor, so that the requirements of biomedical application cannot be met. Therefore, biocompatibility must be improved by surface modification.
Chitosan oligosaccharide is the second most renewable natural high molecular compound in the world after cellulose. It has the advantages of biodegradability, nontoxicity, bioactivity, biocompatibility, antibacterial property and the like. The molecule contains hydroxyl and amino simultaneously, has more active property, and can carry out coupling, activation and modification on the molecule. Gamma-polyglutamic acid is a water-soluble biodegradable high molecular substance, and has the characteristics of edibility, no toxicity, cohesiveness, moisture retention and the like. The application field of the method covers a plurality of aspects such as medicine, chemical industry, food, cosmetics, daily chemical products and the like. Particularly in the field of medicine, as a medicine targeting carrier, the gamma-polyglutamic acid can be degraded into endogenous amino acid in a human body, and has no toxic or side effect on the human body. Meanwhile, as more side chain carboxyl exists, the modified compound can be used as a drug carrier.
At present, no report is available for preparing chitosan oligosaccharide/gamma-polyglutamic acid and iridium nanoparticle targeted drugs.
Disclosure of Invention
Aiming at the problems of blank and the like in the prior art, the invention provides an iridium nanometer intelligent compound medicine which has higher stability and targeting property and can be used for treating tumors in the field of biological medicine.
Meanwhile, the invention also provides a preparation method of the iridium nanometer intelligent composite medicament, which adopts a high-temperature solution method to compound chitosan oligosaccharide, gamma-polyglutamic acid and iridium nanometer particles, and has simple operation.
The technical scheme adopted by the invention for realizing the purpose is as follows:
the invention provides an iridium nanometer intelligent composite medicament, wherein an inner core of the composite medicament is a icosahedron structure of iridium nanoparticles, and the surfaces of the iridium nanoparticles are coated with a mixture of uniform and compact chitosan oligosaccharide and gamma-polyglutamic acid; the content of the iridium nanoparticles is 85-92%, wherein the mass ratio of the iridium nanoparticles to the chitosan and the gamma-polyglutamic acid is 1:1-3: 10-20.
The particle size of the iridium nanometer intelligent composite medicine provided by the invention is less than 100 nm.
Furthermore, the molecular weight of the chitosan oligosaccharide is 1KD, and the molecular weight of the gamma-polyglutamic acid is 40 KD.
Furthermore, the particle diameter of the iridium nano particle is 10-30nm, and the polydispersity is below 0.2.
The invention also provides a preparation method of the iridium nanometer intelligent composite medicine, which is characterized by comprising the following steps:
(1) adding the chloroiridic acid solution into a reaction flask, reacting for 10min at 100 ℃, finishing the reaction, adding ethanol for precipitation when the solution is cooled to 90 ℃, and centrifuging to obtain a precipitate. Washing the precipitate with acetone and deionized water, centrifuging for 3 times, and dispersing the separated nanopowder in deionized water to obtain dispersion;
(2) adding 1/3-2/3 amount of chitosan oligosaccharide into the dispersion, mixing, reacting for 1h at 95 ℃, performing ultrasonic treatment and centrifugation, performing ball milling treatment on large particles of chitosan oligosaccharide and gamma-polyglutamic acid by using liquid nitrogen, adding the rest chitosan oligosaccharide and gamma-polyglutamic acid, reacting for 1h at 60 ℃, and performing freeze drying to obtain the composite iridium nanoparticles;
(3) and washing the composite iridium nano particles by absolute ethyl alcohol, performing centrifugal separation, and finally drying in vacuum at 90 ℃ to obtain the iridium nano intelligent composite medicament.
Further, the concentration of Ir element in the chloroiridic acid solution is 0.5 mg/mL.
Further, in the step (1), the rotating speed of the centrifugation is 15000r/min, and the centrifugation is 5 min.
Further, in the step (2), ball milling is carried out for 120-150 min by using liquid nitrogen until the granularity is 10-30 nm.
The chitosan oligosaccharide utilized by the invention has the characteristics of bacteriostasis, no toxicity, good biocompatibility and the like; the gamma-polyglutamic acid has the characteristics of moisture retention, no toxicity, good biocompatibility and the like; the iridium nano-particle attacks cancer cells in a brand new way, can be safely used, has little side effect, can be combined with various targets in the cells, such as DNA, RNA, protein and the like, has targeting property, generates particles below 100nm after the cross-linking reaction of the three substances, and has simple operation. The obtained iridium nano intelligent composite medicament has a typical core-shell structure, the inner core of the iridium nano intelligent composite medicament is a icosahedron structure of iridium nano particles, and the shell of the iridium nano intelligent composite medicament is composed of uniform and compact CS/gamma-PGA, so that the iridium nano intelligent composite medicament has good dispersibility and better colloid stability; after 40 days, the detection is carried out again, the result is consistent with that before, and the stability is proved to be good.
The icosahedron structure of the iridium nanoparticles is very stable when the pH =7.4, the release rate of the iridium nanoparticles is low, and when the pH = 5.0-6.0, the CS/gamma-PGA film structure and the permeability of the surfaces of the iridium nanoparticles are changed, so that the controllable release of the iridium nanoparticles in the iridium nanoparticles is promoted, and the iridium nanoparticles have the targeting and slow-release capabilities by changing the pH value. Compared with single iridium nano particle, the iridium nano intelligent composite medicine of the invention has more prospect of clinical practical application.
Drawings
FIG. 1 is a Transmission Electron Microscope (TEM) representation of the appearance and particle size of the iridium nanometer intelligent composite drug of example 3.
Fig. 2 is a Transmission Electron Microscope (TEM) characterization of the appearance and particle size of comparative example 1 iridium nanoparticles.
FIG. 3 is a representation of the appearance and particle size of a Transmission Electron Microscope (TEM) versus comparative example 2 iridium nano-intelligent composite drug.
Detailed Description
The present invention will be further described with reference to the following examples, but the present invention is not limited to the following examples.
The raw materials used in the invention are all purchased from the market. The molecular weight of the chitosan oligosaccharide is 1KD, and the molecular weight of the gamma-polyglutamic acid is 40 KD.
Example 1
A preparation method of an iridium nanometer intelligent composite medicine comprises the following steps:
1) 6 mL of chloroiridic acid solution (Ir element concentration: about 0.5 mg/mL) was added to the reaction flask, and the reaction was terminated after 10min at 100 ℃. After the solution was cooled to 90 ℃, 20 mL of ethanol was added for precipitation. The precipitate was obtained by centrifugation at 15000r/min for 5 min in a centrifuge. The precipitate was washed with acetone and deionized water and centrifuged 3 times. Finally, re-dispersing the separated nano powder in deionized water to obtain a reaction system of iridium nano particles (the particle size is 10-30nm, and the polydispersity is below 0.2);
2) adding 4mg of chitosan oligosaccharide into the reaction system in the step 1), mixing, reacting for 1h at 95 ℃, performing ultrasonic treatment for 10min, centrifuging, performing ball milling on large particles in the mixture for 120min by using liquid nitrogen until the particle size is 30nm, adding 4mg of chitosan oligosaccharide and 50mg of gamma-polyglutamic acid, reacting for 1h at 60 ℃, and performing freeze drying for 12h to obtain the composite iridium nanoparticles;
3) washing the iridium nanometer intelligent composite medicament by absolute ethyl alcohol, centrifugally separating, and finally drying in vacuum at 90 ℃ to obtain the iridium nanometer intelligent composite medicament.
The particle size of the iridium nanometer intelligent composite medicine prepared in the embodiment 1 is 10-30nm through detection, the iridium nanometer intelligent composite medicine presents a typical polycrystalline type core-shell structure, the inner core is an icosahedron structure of iridium nanometer particles, and the surfaces of the iridium nanometer particles are coated with a uniform and compact mixture (CS/gamma-PGA) of chitosan oligosaccharide and gamma-polyglutamic acid; the iridium nanoparticles have the inclusion rate of 87%, the mass ratio of the iridium nanoparticles to the chitosan and the gamma-polyglutamic acid is 3:8: 50, the dispersibility is good, the polydispersity is below 0.2, and the colloid stability is good.
The iridium nano particle concentration can reach the effective concentration and can be continuously released for 72h, and the iridium nano particle has good slow release performance. The iridium nanoparticle is very stable when the pH =7.4, the release rate of the iridium nanoparticle is low, and when the pH = 5.0-6.0, the CS/gamma-PGA film structure and the permeability of the surface of the iridium nanoparticle are changed, so that the controllable release of the iridium nanoparticle in the iridium nanoparticle is promoted. After 40 days, the detection result is consistent with that, and the stability is proved to be good.
Example 2:
a preparation method of an iridium nanometer intelligent composite medicine comprises the following steps:
1) 6 mL of chloroiridic acid solution (Ir element concentration: about 0.5 mg/mL) was added to the reaction flask, and the reaction was terminated after 10min at 100 ℃. After the solution was cooled to 90 ℃, 20 mL of ethanol was added for precipitation. The precipitate was obtained by centrifugation at 15000r/min for 5 min in a centrifuge. The precipitate was washed with acetone and deionized water and centrifuged 3 times. Finally, re-dispersing the separated nano powder in deionized water to obtain a reaction system of iridium nano particles (the particle size is 10-30nm, and the polydispersity is below 0.2);
2) adding 3mg of chitosan oligosaccharide into the reaction system in the step 1), mixing, reacting for 1h at 95 ℃, performing ultrasonic treatment for 10min, centrifuging, performing ball milling on large particles in the mixture for 150min by using liquid nitrogen until the particle size is 20nm, adding 5mg of chitosan oligosaccharide and 50mg of gamma-polyglutamic acid, reacting for 1h at 60 ℃, and performing freeze drying for 12h to obtain the composite iridium nanoparticles;
3) washing the iridium nanometer intelligent composite medicament by absolute ethyl alcohol, centrifugally separating, and finally drying in vacuum at 90 ℃ to obtain the iridium nanometer intelligent composite medicament.
The iridium nanometer intelligent composite medicine prepared in the embodiment 2 has a particle size of 10-30nm through detection, and has a typical polycrystalline type core-shell structure, wherein an inner core is an icosahedron structure of iridium nanoparticles, and the surfaces of the iridium nanoparticles are coated with a uniform and compact mixture (CS/gamma-PGA) of chitosan oligosaccharide and gamma-polyglutamic acid; the iridium nanoparticles have the inclusion rate of 90%, the mass ratio of the iridium nanoparticles to the chitosan and the gamma-polyglutamic acid is 3:8: 50, the dispersibility is good, the polydispersity is below 0.2, and the colloid stability is good.
The iridium nano particle concentration can reach the effective concentration and can be continuously released for 72h, and the iridium nano particle has good slow release performance. The iridium nanoparticle is very stable when the pH =7.4, the release rate of the iridium nanoparticle is low, and when the pH = 5.0-6.0, the CS/gamma-PGA film structure and the permeability of the surface of the iridium nanoparticle are changed, so that the controllable release of the iridium nanoparticle in the iridium nanoparticle is promoted. After 40 days, the detection result is consistent with that, and the stability is proved to be good.
Example 3:
a preparation method of an iridium nanometer intelligent composite medicine comprises the following steps:
1) 8 mL of chloroiridic acid solution (Ir element concentration: about 0.5 mg/mL) was added to the reaction flask, and the reaction was terminated after 10min at 100 ℃. After the solution was cooled to 90 ℃, 20 mL of ethanol was added for precipitation. The precipitate was obtained by centrifugation at 15000r/min for 5 min in a centrifuge. The precipitate was washed with acetone and deionized water and centrifuged 3 times. Finally, re-dispersing the separated nano powder in deionized water to obtain a reaction system of iridium nano particles (the particle size is 10-30nm, and the polydispersity is below 0.2);
2) adding 5mg of chitosan oligosaccharide into the reaction system in the step 1), mixing, reacting for 1h at 95 ℃, performing ultrasonic treatment for 10min, centrifuging, performing ball milling on large particles in the mixture for 150min by using liquid nitrogen until the particle size is 20nm, adding 3mg of chitosan oligosaccharide and 50mg of gamma-polyglutamic acid, reacting for 1h at 60 ℃, and performing freeze drying for 12h to obtain the composite iridium nanoparticles;
3) washing the iridium nanometer intelligent composite medicament by absolute ethyl alcohol, centrifugally separating, and finally drying in vacuum at 90 ℃ to obtain the iridium nanometer intelligent composite medicament.
A Transmission Electron Microscope (TEM) picture of the iridium nanometer intelligent composite drug prepared in this embodiment 3 is shown in fig. 1, and the detected particle size is 10-30nm, a typical polycrystalline core-shell structure is presented, the core is an icosahedron structure of iridium nanoparticles, and the surface of the iridium nanoparticles is coated with a uniform and compact mixture (CS/γ -PGA) of chitosan oligosaccharide and γ -polyglutamic acid; the iridium nanoparticles have the inclusion rate of 92%, the mass ratio of the iridium nanoparticles to the chitosan and the gamma-polyglutamic acid is 4:8:50, the dispersibility is good, the polydispersity is below 0.2, and the colloid stability is good.
The iridium nano particle concentration can reach the effective concentration and can be continuously released for 72h, and the iridium nano particle has good slow release performance. The iridium nanoparticle is very stable when the pH =7.4, the release rate of the iridium nanoparticle is low, and when the pH = 5.0-6.0, the CS/gamma-PGA film structure and the permeability of the surface of the iridium nanoparticle are changed, so that the controllable release of the iridium nanoparticle in the iridium nanoparticle is promoted. After 40 days, the detection result is consistent with that, and the stability is proved to be good.
Comparative example 1: iridium nanoparticles used alone
1) 8 mL of chloroiridic acid solution (Ir element concentration: about 0.5 mg/mL) was added to the reaction flask, and the reaction was terminated after 10min at 100 ℃. After the solution was cooled to 90 ℃, 20 mL of ethanol was added for precipitation. The precipitate was obtained by centrifugation at 15000r/min for 5 min in a centrifuge. The precipitate was washed with acetone and deionized water and centrifuged 3 times. Finally, re-dispersing the separated nano powder in deionized water to obtain a reaction system of iridium nano particles (the particle size is 10-30nm, and the polydispersity is below 0.2);
2) washing the iridium nano particles by absolute ethyl alcohol, centrifugally separating, and finally drying in vacuum at 90 ℃ to obtain the iridium nano particles.
The Transmission Electron Microscope (TEM) picture of the iridium nanoparticles obtained in the comparative example 1 is shown in FIG. 2, the detected particle size is 10-20nm, the polydispersity is about 1, and the colloid stability is poorer compared with the composite carrier; the iridium nano particle concentration can be released continuously for 24h when reaching the effective concentration, and the release amount has no obvious difference under different pH conditions. The result shows that the iridium nano intelligent composite medicament is superior to iridium nano particles in the aspects of dispersibility, stability and pH response performance.
Comparative example 2
Iridium nano intelligent composite medicine
The difference from the embodiment 1 is that: and step 2) adding 8mg of chitosan oligosaccharide and 50mg of gamma-polyglutamic acid into the reaction system in the step 1), reacting for 2h at 95 ℃, and removing large particles by ultrasonic and centrifugal treatment to obtain the iridium nano intelligent composite medicament.
The Transmission Electron Microscope (TEM) picture of the iridium nanometer intelligent composite medicament obtained in the comparative example 2 is shown in figure 3, the detected particle size is 40nm, the polydispersity is about 0.3, and compared with the composite carrier, the colloid stability is poorer; the concentration of the iridium nano particles reaches the effective concentration and can be continuously released for 60 hours. After detection for 40 days, an obvious aggregation phenomenon appears, and the stability of the iridium nanometer intelligent composite medicament is poorer than that of the iridium nanometer intelligent composite medicament in the embodiment 1.
Comparative example 3
Iridium nano intelligent composite medicine
The difference from the embodiment 1 is that: and step 2) adding 8mg of chitosan oligosaccharide and 50mg of gamma-polyglutamic acid into the reaction system in the step 1), reacting for 2h at 60 ℃, and removing large particles by ultrasonic and centrifugal treatment to obtain the iridium nano intelligent composite medicament.
The iridium nanometer intelligent composite medicament obtained in the comparative example 3 has the grain diameter of 80nm and the polydispersity coefficient of about 0.3 through detection, and has poorer colloid stability compared with a composite carrier; the concentration of the iridium nano particles reaches the effective concentration and can be continuously released for 60 hours. After detection for 40 days, an obvious aggregation phenomenon appears, and the stability of the iridium nanometer intelligent composite medicament is poorer than that of the iridium nanometer intelligent composite medicament in the embodiment 1.
Claims (7)
1. The preparation method of the iridium nano composite medicine is characterized in that the inner core of the composite medicine is in a icosahedron structure of iridium nano particles, and the surfaces of the iridium nano particles are coated with a mixture of uniform and compact chitosan oligosaccharide and gamma-polyglutamic acid; the content of the iridium nanoparticles is 85-92%, wherein the mass ratio of the iridium nanoparticles to the chitosan oligosaccharide to the gamma-polyglutamic acid is 1:1-3: 10-20;
the method comprises the following specific steps:
(1) adding the chloroiridic acid solution into a reaction flask, reacting for 10min at 100 ℃, finishing the reaction, adding ethanol for precipitation when the solution is cooled to 90 ℃, and centrifuging to obtain a precipitate. Washing the precipitate with acetone and deionized water, centrifuging for 3 times, and dispersing the separated nanopowder in deionized water to obtain dispersion;
(2) adding 1/3-2/3 amount of chitosan oligosaccharide into the dispersion, mixing, reacting for 1h at 95 ℃, performing ultrasonic treatment and centrifugation, performing ball milling treatment on large particles of chitosan oligosaccharide and gamma-polyglutamic acid by using liquid nitrogen, adding the rest chitosan oligosaccharide and gamma-polyglutamic acid, reacting for 1h at 60 ℃, and performing freeze drying to obtain the composite iridium nanoparticles;
(3) and washing the composite iridium nano particles by absolute ethyl alcohol, performing centrifugal separation, and finally drying at 90 ℃ in vacuum to obtain the iridium nano composite medicament.
2. The method of claim 1, wherein: the particle size of the composite medicine is less than 100 nm.
3. The method of claim 1, wherein: the molecular weight of the chitosan oligosaccharide is 1KD, and the molecular weight of the gamma-polyglutamic acid is 40 KD.
4. The method of claim 1, wherein: the particle diameter of the iridium nanoparticles is 10-30nm, and the polydispersity is below 0.2.
5. The production method according to claim 1, wherein the Ir element concentration in the chloroiridic acid solution is 0.5 mg/mL.
6. The method according to claim 1, wherein in the step (1), the rotation speed of the centrifugation is 15000r/min and the centrifugation is 5 min.
7. The method of claim 1, wherein: in the step (2), ball milling is carried out for 120-150 min by using liquid nitrogen until the granularity is 10-30 nm.
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