CN103656668B - Bortezomib slow releasing preparation and preparation method thereof - Google Patents
Bortezomib slow releasing preparation and preparation method thereof Download PDFInfo
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Abstract
The invention discloses a kind of bortezomib slow releasing preparation and preparation method thereof, belong to nano material and agent field, pharmaceutical carrier field.Said preparation includes using the chitosan of carbon quantum dot labelling as slow-released carrier, its preparation method: the peptide boric acid root of bortezomib obtains peptide boric acid ester with the hydroxyl generation esterification of chitosan, thus bortezomib is grafted to chitosan nano；Carbon quantum dot carries out Electrostatic Absorption by surface carboxyl groups with the amino on chitosan in above-mentioned chitosan nano, thus carbon quantum dot load is entered in chitosan nano system, prepare absorption carbon quantum dot and the chitosan nano bortezomib slow releasing preparation of coupling bortezomib.Compared with prior art, bortezomib slow releasing preparation of the present invention and preparation method thereof has the features such as function admirable such as feasible process, simple to operate, targeting and controllable release, in bio-sensing, medical function nano material, especially the controlled release aspect of pharmaceutical carrier or preparation, has important using value.
Description
Technical field
The present invention relates to nano material and pharmaceutical carrier field, specifically a kind of bortezomib slow releasing preparation and preparation method thereof.
Background technology
According to World Health Organization's recent statistics, will increase by 50% to the year two thousand twenty whole world cancer morbidity, number of the infected increases to 15,000,000.Anticipated the year two thousand twenty China will have 4,000,000 people to die from cancer every year.Therefore, one of method or medicine focus having become as research at present of inquiring into a kind of effective treatment cancer.
Bortezomib (Bortezomib, BTZ), as a kind of new protease inhibitor, in recent years mainly as the choice drug for the treatment of multiple myeloma, also has certain therapeutic effect to other tumor simultaneously.When bortezomib is individually used for treating tumor, tool has certain effect, but the whole body toxic and side effects caused by conventional route administration limits the effect of its clinical practice.Chemotherapeutics topical application, especially local sustained release have become as the study hotspot of current entity chemotherapy of tumors.Slow-release auxiliary material used by existing bortezomib preparation more or less can cause burst drug release, unbalanced release when release, or discharged and make topically effective drug level not enough slowly, thus can not effectively kill tumor cell, if discharging too fast or prominent releasing, then can cause the toxic reaction of whole body as regular injection.
In the preparation research of existing bortezomib, the methods such as liposome entrapment, antibodies, medication combined, freeze-dried powder, aminoacid doping are have employed.Such as, S·Prick Lipsky etc. the polyol reaction of boronic acid compounds with liposome entrapment is generated borate and by bag be loaded in liposome (patent publication No.:
CN101094648).D·A Faer etc. develop medication combined bortezomib for treating multiple myeloma based on anti-cs 1 antibodies method (patent publication No.:
CN101686971).Hou Hongchun etc. are prepared for the anti-cancer composition (patent publication No.: CN101301469) containing nitrosourea medicament and bortezomib.Chen Qingcais etc. have prepared a kind of freeze-dried composition (patent publication No.: CN103070835A) containing bortezomib by adding mannitol or the tert-butyl alcohol.Li Cuiyan etc. have studied a kind of bortezomib and the preparation (patent publication No.: CN103142509A) of aminoacid doping.
The pharmaceutical preparation of bortezomib can be obtained although with above method, but the technical problem that still there is some key is urgently to be resolved hurrily, such as preparation technology and cost, the biocompatibility of preparation, the stability of slow releasing preparation, targeting and the controllability etc. of drug release.Therefore, develop the bortezomib slow releasing agent of the performances such as a kind of reasonable in design, feasible process, simple to operate, drug targeting and controllable release, in association areas such as biology, medical science, materials, all there is highly important Research Significance and using value.Up to now, there is not yet the bortezomib hydroxyl reaction by peptide boric acid root with chitosan, generate peptide boric acid ester and obtain loading the chitosan nano of bortezomib, also there is not yet and carry out Electrostatic Absorption self assembly by the chitosan nano internal amino of carbon quantum dot surface carboxyl groups with load bortezomib and prepare the relevant report of the bortezomib slow releasing agent of carbon quantum dot-chitosan composite nano-granule.
Summary of the invention
The technical assignment of the present invention is for above-mentioned the deficiencies in the prior art, it is provided that the bortezomib slow releasing preparation of the function admirables such as a kind of feasible process, simple to operate, targeting and controllable release.
The further technical assignment of the present invention is to provide the preparation method of above-mentioned preparation.
The technical assignment of the present invention realizes in the following manner: bortezomib slow releasing preparation, is characterized in using the chitosan of carbon quantum dot labelling as slow-released carrier.
The preparation method of above-mentioned slow releasing preparation includes:
The peptide boric acid root of bortezomib obtains peptide boric acid ester with the hydroxyl generation esterification of chitosan, thus bortezomib is grafted to chitosan nano；
Carbon quantum dot carries out Electrostatic Absorption by surface carboxyl groups with the amino on chitosan in above-mentioned chitosan nano, thus carbon quantum dot load is entered in chitosan nano system, prepare absorption carbon quantum dot and the chitosan nano bortezomib slow releasing preparation of coupling bortezomib.
Further, above-mentioned preparation method comprises the following steps:
(1) add Chitosan powder with appropriate acetic acid to dissolve, add methanol the most again and dissolve, obtain chitosan methanol dispersion liquid；
(2) a certain amount of bortezomib is weighed, under magnetic agitation and supersonic vibration are common, add methanol to dissolve, it is subsequently adding step (1) gained chitosan methanol dispersion liquid, adding pH value regulator, regulation solution, to alkalescence, carries out esterification, obtaining peptide boric acid ester based on bortezomib Yu chitosan, the bortezomib percent grafting of chitosan is 5 ~ 20
%；
(3) fully dissolve glucose with Polyethylene Glycol, then proceed to microwave reactor reaction certain time, prepare the carboxylic carbon quantum dot in surface；
(4) during carbon quantum dot is dispersed in methanol, add step (2) gained peptide boric acid ester, electrostatic adsorption occurs, prepare absorption carbon quantum dot and the chitosan nano bortezomib slow releasing preparation of coupling bortezomib.
Described in step (1), the molecular weight of chitosan is 4 ~ 100,000, and the concentration of chitosan methanol dispersion liquid is 0.1 ~ 1 g/L.
In step (2), adding pH value regulator, regulation pH value of solution is 9 ~ 12.Described pH value regulator is tetramethylammonium hydroxide series apolar agent, such as four hydration Tetramethylammonium hydroxide, five hydration Tetramethylammonium hydroxide and six hydration Tetramethylammonium hydroxide etc..
In step (3), the polyglycol solution concentration of glucose is 40 ~ 1000 mg/mL, and the microwave reaction time is 1 ~ 10 min.
Carbon quantum dot described in step (4) is 1:1 ~ 1:10 with the molar concentration rate of peptide boric acid ester.
Bortezomib slow releasing preparation of the present invention and preparation method thereof compared with prior art has a ground highlighted below beneficial effect:
(1) average-size of bortezomib slow releasing preparation (i.e. carbon quantum dot-bortezomib-chitosan composite nano-granule) is 100 ~ 200 nm, have biocompatibility, have no side effect, the character such as fluorescent tracing and pH are sensitive, at bio-sensing, bio-medical material, function nano material, especially the control release aspect of pharmaceutical carrier or preparation, has important Research Significance and using value；
(2) preparation method has the feature such as feasible process, simple to operate, easy control of reaction, utilizes popularization and application.
Accompanying drawing explanation
Accompanying drawing 1 be bortezomib (BTZ) with chitosan (Chitosan, CS) nano-complex prepare schematic diagram；
Accompanying drawing 2 is bortezomib (BTZ)-chitosan (CS)-carbon quantum dot (Carbon quantum
Dot, CQD) nano-complex (BTZ-CS-CQD) prepare schematic diagram；
Accompanying drawing 3 is hydrodynamic size distribution distribution and the average-size of BTZ-CS-CQD nanoparticle；
Accompanying drawing 4 is that BTZ-CS-CQD nanoparticle is swallowed the fluorescent images after entering L929 cell；
Accompanying drawing 5 is the concentration curve that BTZ-CS-CQD nanoparticulate carriers discharges BTZ under different pH.
Detailed description of the invention
Bortezomib slow releasing preparation of the present invention and preparation method thereof is described in detail below with specific embodiment with reference to Figure of description.
If no special instructions, the content of following each composition used is weight percentage content.
Embodiment one,
Bortezomib (BTZ)-chitosan (CS)-carbon quantum dot (CQD) composite nano-granule (BTZ-CS-CQD), the i.e. preparation (preparation process is as shown in accompanying drawing 1,2) of bortezomib slow releasing preparation: first, weigh 50mg CS(molecular weight 40,000), dropping 2mL acetic acid, it is subsequently adding 98 mL absolute methanols to continue to dissolve, forms the methanol dispersion liquid (0.5g/L) of CS.Then, adding 10mg BTZ and fully dissolve, mixed liquor is warming up to 60 DEG C, being added dropwise over five hydration Tetramethylammonium hydroxide regulation pH is 10, keeps magnetic agitation 1h, obtains the CS nanoparticle that BTZ percent grafting is 10%.Then, after dissolving 1g glucose with 5mL Polyethylene Glycol, proceed to microwave reactor, under 540W power, react 5min, prepare CQD.Finally, in the methanol dispersion liquid of BTZ-CS nanoparticle (0.5g/L), add carbon quantum dot (0.1g/L), obtain BTZ-CS-CQD composite nano-granule by Electrostatic Absorption.
Performance study:
By above-mentioned product by bag filter dialysis, to remove unreacted monomer and impurity, then prepare certain concentration (0.1g/L) and be dispersed in phosphate buffer (pH7.4) standby.
Using dynamic light scattering to measure hydrodynamic size and the distribution of above-mentioned BTZ-CS-CQD composite nano-granule, average-size is 190.5nm and narrow distribution (as shown in accompanying drawing 3)；Fluorescent images after using this nanoparticle of fluorescence microscope to be swallowed by L929 cancerous cell, it was demonstrated that the fluorescent tracing ability (as shown in Figure 4) in tumor cell of the carbon quantum dot in nanoparticle；Use the BTZ concentration of high effective liquid chromatography for measuring release, study this nanoparticle pH sensitivity releasing properties (as shown in Figure 5) as BTZ preparation or carrier.
Embodiment two:
Bortezomib (BTZ)-chitosan (CS)-carbon quantum dot (CQD) composite nano-granule (BTZ-CS-CQD), the i.e. preparation of bortezomib slow releasing preparation: first, weigh 40mg CS(molecular weight 60,000), dropping 2mL acetic acid, it is subsequently adding 98 mL absolute methanols to continue to dissolve, forms the methanol dispersion liquid (0.4g/L) of CS.Then, adding 10mg BTZ and fully dissolve, mixed liquor is warming up to 60 DEG C, being added dropwise over five hydration Tetramethylammonium hydroxide regulation pH is 11, keeps magnetic agitation 1h, obtains the CS nanoparticle that BTZ percent grafting is 5%.Then, after dissolving 2g glucose with 10mL Polyethylene Glycol, proceed to microwave reactor, under 540W power, react 5min, prepare CQD.Finally, in the methanol dispersion liquid of BTZ-CS nanoparticle (0.5g/L), add carbon quantum dot (0.2g/L), obtain BTZ-CS-CQD composite nano-granule by Electrostatic Absorption.
The performance characterization of this nanoparticulate carriers is all identical with embodiment one with research method.
Embodiment three:
Bortezomib (BTZ)-chitosan (CS)-carbon quantum dot (CQD) composite nano-granule (BTZ-CS-CQD), the i.e. preparation of bortezomib slow releasing preparation: first, weigh 80mg CS(molecular weight 80,000), dropping 2mL acetic acid, it is subsequently adding 98 mL absolute methanols to continue to dissolve, forms the methanol dispersion liquid (0.8g/L) of CS.Then, adding 10mg BTZ and fully dissolve, mixed liquor is warming up to 60 DEG C, being added dropwise over five hydration Tetramethylammonium hydroxide regulation pH is 11, keeps magnetic agitation 1h, obtains the CS nanoparticle that BTZ percent grafting is 15%.Then, after dissolving 3g glucose with 15mL Polyethylene Glycol, proceed to microwave reactor, under 540W power, react 5min, prepare CQD.Finally, in the methanol dispersion liquid of BTZ-CS nanoparticle (1.0g/L), add carbon quantum dot (0.2g/L), obtain BTZ-CS-CQD composite nano-granule by Electrostatic Absorption.
The performance characterization of this nanoparticulate carriers is all identical with embodiment one with research method.
Embodiment four:
Bortezomib (BTZ)-chitosan (CS)-carbon quantum dot (CQD) composite nano-granule (BTZ-CS-CQD), the i.e. preparation of bortezomib slow releasing preparation: first, weigh 100mg CS(molecular weight 80,000), dropping 2mL acetic acid, it is subsequently adding 98 mL absolute methanols to continue to dissolve, forms the methanol dispersion liquid (1.0g/L) of CS.Then, adding 10mg BTZ and fully dissolve, mixed liquor is warming up to 60 DEG C, being added dropwise over five hydration Tetramethylammonium hydroxide regulation pH is 12, keeps magnetic agitation 1h, obtains the CS nanoparticle that BTZ percent grafting is 20%.Then, after dissolving 4g glucose with 20mL Polyethylene Glycol, proceed to microwave reactor, under 540W power, react 5min, prepare CQD.Finally, in the methanol dispersion liquid of BTZ-CS nanoparticle (1.0g/L), add carbon quantum dot (0.5g/L), obtain BTZ-CS-CQD composite nano-granule by Electrostatic Absorption.
The performance characterization of this nanoparticulate carriers is all identical with embodiment one with research method.
Embodiment five:
Bortezomib (BTZ)-chitosan (CS)-carbon quantum dot (CQD) composite nano-granule (BTZ-CS-CQD), the i.e. preparation of bortezomib slow releasing preparation: first, weigh 80mg CS(molecular weight 100,000), dropping 2mL acetic acid, it is subsequently adding 98 mL absolute methanols to continue to dissolve, forms the methanol dispersion liquid (0.8g/L) of CS.Then, adding 10mg BTZ and fully dissolve, mixed liquor is warming up to 60 DEG C, being added dropwise over five hydration Tetramethylammonium hydroxide regulation pH is 11, keeps magnetic agitation 1h, obtains the CS nanoparticle that BTZ percent grafting is 15%.Then, after dissolving 5g glucose with 25mL Polyethylene Glycol, proceed to microwave reactor, under 540W power, react 5min, prepare CQD.Finally, in the methanol dispersion liquid of BTZ-CS nanoparticle (1.0g/L), add carbon quantum dot (1.0g/L), obtain BTZ-CS-CQD composite nano-granule by Electrostatic Absorption.
The performance characterization of this nanoparticulate carriers is all identical with embodiment one with research method.
Claims (2)
1. bortezomib slow releasing preparation, it is characterised in that: said preparation comprises the following steps using the chitosan of carbon quantum dot labelling as slow-released carrier, its preparation method:
(1) add Chitosan powder with appropriate acetic acid to dissolve, add methanol the most again and dissolve, obtain chitosan methanol dispersion liquid,
The molecular weight of described chitosan is 4 ~ 100,000, and the concentration of chitosan methanol dispersion liquid is 0.1 ~ 1 g/L；
(2) a certain amount of bortezomib is weighed, under magnetic agitation and supersonic vibration act on jointly, add methanol to dissolve, it is subsequently adding step (1) gained chitosan methanol dispersion liquid, adding pH value regulator, regulation solution is 9 ~ 12 to pH, carries out esterification, obtain peptide boric acid ester based on bortezomib Yu chitosan
Described pH value regulator is tetramethylammonium hydroxide set of polar reagent；
(3) fully dissolve glucose with Polyethylene Glycol, then proceed to microwave reactor reaction certain time, prepare the carboxylic carbon quantum dot in surface,
The polyglycol solution concentration of glucose is 40 ~ 1000
Mg/mL, the microwave reaction time is 1 ~ 10 min；
(4) during carbon quantum dot is dispersed in methanol, add step (2) gained peptide boric acid ester, electrostatic adsorption occur, prepare absorption carbon quantum dot and the chitosan nano bortezomib slow releasing preparation of coupling bortezomib,
Carbon quantum dot is 1:1 ~ 1:10 with the molar concentration rate of peptide boric acid ester.
2. the preparation method of bortezomib slow releasing preparation, it is characterised in that: comprise the following steps:
(1) add Chitosan powder with appropriate acetic acid to dissolve, add methanol the most again and dissolve, obtain chitosan methanol dispersion liquid,
The molecular weight of described chitosan is 4 ~ 100,000, and the concentration of chitosan methanol dispersion liquid is 0.1 ~ 1 g/L；
(2) a certain amount of bortezomib is weighed, under magnetic agitation and supersonic vibration act on jointly, add methanol to dissolve, it is subsequently adding step (1) gained chitosan methanol dispersion liquid, adding pH value regulator, regulation solution is 9 ~ 12 to pH, carries out esterification, obtain peptide boric acid ester based on bortezomib Yu chitosan
Described pH value regulator is tetramethylammonium hydroxide set of polar reagent；
(3) fully dissolve glucose with Polyethylene Glycol, then proceed to microwave reactor reaction certain time, prepare the carboxylic carbon quantum dot in surface,
The polyglycol solution concentration of glucose is 40 ~ 1000
Mg/mL, the microwave reaction time is 1 ~ 10 min；
(4) during carbon quantum dot is dispersed in methanol, add step (2) gained peptide boric acid ester, electrostatic adsorption occur, prepare absorption carbon quantum dot and the chitosan nano bortezomib slow releasing preparation of coupling bortezomib,
Carbon quantum dot is 1:1 ~ 1:10 with the molar concentration rate of peptide boric acid ester.
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| CN104958768A (en) * | 2015-07-17 | 2015-10-07 | 中国科学院长春应用化学研究所 | Glucosan-bortezomib bonding medicine and preparation method thereof |
| CN104958769A (en) * | 2015-07-17 | 2015-10-07 | 中国科学院长春应用化学研究所 | Oxidized dextran-bortezomib-adriamycin bonded chemical and preparation method thereof |
| CN105462583A (en) * | 2015-11-03 | 2016-04-06 | 南京工业大学 | Preparation method and application of ethanol solution with fluorescent nano carbon quantum dots |
| CN108404285A (en) * | 2018-05-22 | 2018-08-17 | 蔡毓旻 | A kind of equipment of adjuvant therapy rheumatoid arthritis |
| CN109045272A (en) * | 2018-08-01 | 2018-12-21 | 厦门市壳聚糖生物科技有限公司 | A kind of bortezomib phosphatide complexes and the preparation method and application thereof |
| CN110492175B (en) * | 2019-08-13 | 2020-12-15 | 中北大学 | Organic nanocomposite electrolyte membrane for all-solid-state alkali metal battery and preparation method thereof |
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