CN103212083B - Method for preparing stable albumin nano-particles - Google Patents
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Abstract
The invention discloses a method for preparing stable albumin nano-particles, belonging to the technical field of biological medicine material preparation. The method comprises the following steps of: carrying out pretreatment on albumin by utilizing non-biotoxic glutathione or cysteine to open intramolecular dithio bonds, precipitating the albumin by using anti-solvents such as alcohol and the like, and carrying out sulfydryl-dithio bond exchange reaction so as to obtain albumin nano-particles with intermolecular dithio bonds. The prepared nano-particles can be used for delivering in-vivo pharmacologically active substances and/or diagnosis aids. The obtained albumin nano-particles have the advantages that the albumin nano-particles not only have good stability under dilution condition, but also have oxidation reduction response in a reduction type environment; and due to such characteristics, the particles can stably exist in in-vivo blood circulation systems of organisms and are degraded under the action of reduced glutathione so as to release the wrapped medicine.
Description
Technical field
The present invention relates to a kind of preparation method of albumin nanometer rice grain, belong to biological medicine technical field of material.
Background technology:
Albumin is a kind of biological endogenous property albumen, and the various features such as biodegradable, nontoxic, no antigen having, is considered to a desirable pharmaceutical carrier, and albumin medicine-carried system is a research direction that has vitality in study of pharmacy now.Albumin medicine-carried system is mainly divided into two large classes, and a class is the albumin medicine-carried system of chemical coupling, and another kind of is the albumin medicine-carried system of physical bond.The albumin of chemical coupling can improve the pharmacokinetic properties of medicine, but has formed new chemical molecular in conjunction with rear.The albumin drug delivery system of physical bond form is a more preferably medicine carrying pattern, drug molecule is wrapped in albumin nanometer rice grain, can obviously improves water-insoluble medicine stability and dissolubility of (being in body inner blood blood circulation) in aqueous solution.Meanwhile, utilize the permeability of tumor tissues to strengthen and retention effect (EPR effect), can be so that albumin nanometer rice medicine-carried system reaches the object of target administration.
Because albumin molecule has fabulous water solublity, how to make albumin nanometer rice grain in water, have good stability, under diluting condition, not dissolving is the difficult point in current technology of preparing.The cross-linking agent such as glutaraldehyde are often used to the stable nano-particle obtaining, but the amino sites on glutaraldehyde meeting nonselective albumin-binding surface can discharge aldehydes residue in vivo, and organism is had to remarkable toxic and side effects.The albumin nano granular synthetic technology (CN102048695A) that has a kind of self assembly of report, utilize mercaptoethanol etc. as reducing agent, to open the disulfide bond of albumin molecule, make it utilize hydrophobic interaction to be combined into nano-particle, but this granule all dissolves in 10% ethanol water, illustrate that this granule only depends on hydrophobic interaction stable, and be not stable (the Gong M.G.et al. of disulfide-bonded, Biomacromolecules, 2012,13,23-28).American Bioscience company has developed a kind of nab technology (Nanoparticle albumin-bound technology) forming based on disulfide bond, using albumin as substrate and stabilizing agent, in the situation that not adding any emulsifying agent and cross-linking agent, make albumin nano granular (US6753006B1).But in recent years to Abraxane product dilution experiment (Chauhan V.P.et al., Nature Nanotech., 2012,7,383-388. show, after Abraxane is diluted in buffer solution or bovine serum albumin solution, can be decomposed at once the big or small granule of 10nm left and right, this shows that this product is also not obtained by disulfide bond crosslinking.
Summary of the invention:
The object of this invention is to provide a kind of method of preparing stable albumin nanometer rice grain, this albumin nano granular is cross-linked by intermolecular disulfide bond and stablizes, and in order to solve some pharmacological active substance, is difficult to carry out the problem of sending in body.
In order to realize object of the present invention, technical scheme of the present invention is:
A method of preparing stable albumin nanometer rice grain, following steps are carried out:
1) prepare the albumin aqueous solution that volume mass concentration is 10～200mg/mL;
2) in albumin aqueous solution, add glutathion or cysteine, make its molar concentration in albumin aqueous solution reach 10～500mM, at 10～60 ℃ of temperature, react 5～240min;
3) in step 2) add ethanol or the tert-butyl alcohol in reacted solution, at 10～60 ℃ of temperature, reaction 5～120min, obtains the suspension of the crosslinked albumin nanometer rice grain of intermolecular disulfide bond; Described albumin aqueous solution is 1:1～5 with the volume ratio of the ethanol adding or the tert-butyl alcohol;
4) by the dialysis at 0～20 ℃ of temperature of the suspension of albumin nanometer rice grain, obtain albumin nanoparticles solution, then through lyophilization, spraying is dry or processed is carried out in distilling under reduced pressure, obtains albumin nanometer rice grain.
For sending a preparation method for the albumin nanometer rice grain of pharmacologically active medicine in body, carry out as follows:
1) prepare the albumin aqueous solution that volume mass concentration is 10～200mg/mL;
2) in albumin aqueous solution, add glutathion or cysteine, make its molar concentration in albumin aqueous solution reach 10～500mM, at 10～60 ℃ of temperature, react 5～240min;
3) in step 2) add the t-butanol solution of alcoholic solution or the pharmacologically active medicine of pharmacologically active medicine in reacted solution, at 10～60 ℃ of temperature, react 5～120min, obtain wrapping up the suspension of the albumin nanometer rice grain of pharmacological active substance; Described albumin aqueous solution is 1:1～5 with the volume ratio of the alcoholic solution of the pharmacologically active medicine adding or the t-butanol solution of pharmacologically active medicine;
4) by the dialysis at 0～20 ℃ of temperature of the suspension of albumin nanometer rice grain, obtain wrapping up the solution of the albumin nanometer rice grain of pharmacological active substance, process lyophilization again, spraying are dried or processed is carried out in distilling under reduced pressure, obtain wrapping up the albumin nanometer rice grain of pharmacological active substance.
The albumin nano granular mean diameter obtaining in technical solution of the present invention is 10～500nm.
Albumin molecule described in technical solution of the present invention comprises human serum albumin (human serum albumin, HSA), bovine serum albumin (bovine serum albumin, BSA), recombination human serum albumin (recombinant HSA, or their combination rHSA).
In the albumin nanometer rice grain of the parcel pharmacological active substance described in technical solution of the present invention, can wrap and carry the pharmacological active substance that accounts for nanoparticle total amount 1%～90%.
Pharmacological active substance described in technical solution of the present invention is cancer therapy drug.
Cancer therapy drug described in technical solution of the present invention comprises paclitaxel, Docetaxel, amycin, curcumin, platinum, methotrexate or their combination.
The advantage of the albumin nanometer rice grain of the prepared albumin nanometer rice grain of the present invention and parcel pharmacological active substance is: the albumin in nano-particle has intermolecular disulfide bond crosslinked, equal stable existence in aqueous solution between pH scope 3-4 and 6-10, stable existence in the ethanol water that is 1～50% in volume fraction, and (37 ℃ of physiological conditions, pH=7.4) stable existence in the dilution experiment under, this granule can progressively dissolve in reproducibility environment simultaneously.Above characteristic make this granule can stable existence in organism inner blood blood circulation, and in cell, under the effect of reduced glutathion, degrade and discharge wrapped up medicine.
Accompanying drawing explanation:
Fig. 1 is the stability study of albumin nano granular in different solvents environment in the present invention.
Fig. 2 is the SDS-PAGE electrophoretogram of albumin nano granular after progressively dissolving under reduced form condition in the present invention.Wherein, 1 band that is albumin nano granular, 2 is the band of albumin oligomer, and 3 is albumin dimer and trimerical band, and 4 is the monomolecular band of albumin.
Fig. 3 is surface sweeping electron microscope image and the transmission electron microscope image of albumin-curcumin nanoparticles in the present invention.Wherein, A and B are surface sweeping electron microscope image, and C and D are transmission electron microscope image.
The specific embodiment:
A kind of method of preparing stable albumin nanometer rice grain provided by the invention, the method is carried out as follows:
1) prepare the albumin aqueous solution that volume mass concentration is 10～200mg/mL; Described albumin generally adopts human serum albumin, bovine serum albumin, recombination human serum albumin or their combination.
2) in albumin aqueous solution, add glutathion or cysteine, make its molar concentration in albumin aqueous solution reach 10～500mM, at 10～60 ℃ of temperature, react 5～240min;
3) in step 2) add ethanol or the tert-butyl alcohol in reacted solution, at 10～60 ℃ of temperature, react 5～120min, obtain the suspension of the crosslinked albumin nanometer rice grain of intermolecular disulfide bond; Described albumin aqueous solution is 1:1～5 with the volume ratio of the ethanol adding or the tert-butyl alcohol;
4) by the dialysis at 0～20 ℃ of temperature of the suspension of albumin nanometer rice grain, obtain albumin nanoparticles solution, then through lyophilization, spraying is dry or processed is carried out in distilling under reduced pressure, obtains albumin nanometer rice grain.The albumin nano granular mean diameter obtaining is 10～500nm.
Provided by the invention a kind of for sending the preparation method of the albumin nanometer rice grain of pharmacologically active medicine in body, the method is carried out as follows:
1) prepare the albumin aqueous solution that volume mass concentration is 10～200mg/mL;
2) in albumin aqueous solution, add glutathion or cysteine, make its molar concentration in albumin aqueous solution reach 10～500mM, at 10～60 ℃ of temperature, react 5～240min;
3) in step 2) add the t-butanol solution of alcoholic solution or the active medicine of pharmacologically active medicine in reacted solution, at 10～60 ℃ of temperature, react 5～120min, obtain wrapping up the suspension of the albumin nanometer rice grain of pharmacological active substance; Described albumin aqueous solution is 1:1～5 with the volume ratio of the alcoholic solution of the pharmacologically active medicine adding or the t-butanol solution of pharmacologically active medicine; Pharmacological active substance is cancer therapy drug, for example the analog of paclitaxel, Docetaxel, amycin, curcumin, platinum and platinum, methotrexate or their combination.
4) by the dialysis at 0～20 ℃ of temperature of the suspension of albumin nanometer rice grain, obtain wrapping up the solution of the albumin nanometer rice grain of pharmacological active substance, process lyophilization again, spraying are dried or processed is carried out in distilling under reduced pressure, obtain wrapping up the albumin nanometer rice grain of pharmacological active substance.The pharmacological active substance that in albumin nano granular, bag carries accounts for 1%～90% of nanoparticle total amount.
For a better understanding of the present invention, below in conjunction with five examples, the present invention is described in further details.But protection domain of the present invention is not limited to the expressed scope of embodiment.
Experimental technique described in following embodiment, if no special instructions, is conventional method; Described reagent and material, if no special instructions, all can obtain from commercial channels.
Embodiment 1, prepares the stable human serum albumin's nano-particle of disulfide bond.
Take human serum albumin and reduced glutathion as raw material, prepare the stable human serum albumin's nano-particle of disulfide bond.
Concrete preparation method is as follows:
Human serum albumin 20mg is dissolved in the aqueous solution of 1mL, and add 20mM reduced glutathion, under room temperature, react 1 hour, then add 4mL dehydrated alcohol reaction 30 minutes, subsequently by prepared suspension as in bag filter, in the deionized water under the environment of 4 ℃, dialyse 24 hours, obtain the stable human serum albumin's nano-particle of disulfide bond, and the mean diameter of albumin nano granular is 100～300nm (ZetaPALS, Zeta Potential Analyzer).
The stability of prepared nano-particle in different solvents environment can be as seen from Figure 1.The progressively course of dissolution of prepared nano-particle under reducing environment can be confirmed from the SDS-PAGE gel electrophoresis figure of Fig. 2.
Embodiment 2, prepare the stable human serum albumin's nano-particle of disulfide bond.
Take human serum albumin and reduced glutathion as raw material, prepare the stable human serum albumin's nano-particle of disulfide bond.
Concrete preparation method is as follows:
Human serum albumin 200mg is dissolved in the aqueous solution of 1mL, and add 500mM reduced glutathion, 50 ℃ are reacted 10 minutes, then add 1mL dehydrated alcohol reaction 5 minutes, then by prepared suspension as in bag filter, in deionized water under the environment of 10 ℃, dialyse 24 hours, obtain the stable human serum albumin's nano-particle of disulfide bond, and the mean diameter of albumin nano granular is 100～400nm.
Embodiment 3, prepare the stable curcumin-human serum albumin nano-particle medicine-carried system of disulfide bond.
With human serum albumin, reduced glutathion and curcumin are raw material, prepare the nano-particle medicine-carried system of the coated curcumin of the stable human serum albumin of disulfide bond.
Concrete preparation method is as follows:
Human serum albumin 40mg is dissolved in the aqueous solution of 1mL, and add 50mM reduced glutathion, under room temperature, react 1 hour, then add the 3mg/mL curcumin alcoholic solution of 4mL to react 30 minutes, subsequently by prepared suspension as in bag filter, in deionized water under the environment of 4 ℃, dialyse 24 hours, obtain the stable curcumin-human serum albumin of disulfide bond and wrap nano-particle.And the mean diameter of nanoparticle is 50～400nm (ZetaPALS, Zeta Potential Analyzer), with anti-phase C18, firmly measure the drug loading of curcumin, mobile phase is methanol: water: acetic acid (80:19:1), detection wavelength is 428nm.HPLC analyzes and shows that the curcumin drug loading of this experiment reaches 21%.Prepared nano-particle pattern is confirmed from the sem image of Fig. 3.
Embodiment 4, prepare the stable curcumin-human serum albumin nano-particle medicine-carried system of disulfide bond.
With human serum albumin, reduced glutathion and curcumin are raw material, prepare the nano-particle medicine-carried system of the coated curcumin of the stable human serum albumin of disulfide bond.
Concrete preparation method is as follows:
Human serum albumin 10mg is dissolved in the aqueous solution of 1mL, and add 50mM reduced glutathion, under room temperature, react 1 hour, then add the 3mg/mL curcumin alcoholic solution of 4mL to react 30 minutes, subsequently by prepared suspension as in bag filter, in deionized water under the environment of 4 ℃, dialyse 24 hours, obtain the stable curcumin-human serum albumin of disulfide bond and wrap nano-particle.The mean diameter of prepared nanoparticle is 50～400nm, and HPLC analyzes and shows that the curcumin drug loading of this experiment reaches 40%.
Embodiment 5, prepare the stable paclitaxel-human serum albumin nano-particle of disulfide bond.
With human serum albumin, reduced glutathion and paclitaxel are raw material, prepare the stable paclitaxel-human serum albumin nano-particle medicine-carried system of disulfide bond.
Concrete preparation method is as follows:
Human serum albumin 40mg is dissolved in the aqueous solution of 1mL, and add 50mM reduced glutathion, at 25 ℃, react 4 hours, then add the t-butanol solution of the 2.5mg/mL paclitaxel of 3.5mL to react 30 minutes, subsequently by prepared suspension as in bag filter, in deionized water under the environment of 4 ℃, dialyse 24 hours, obtain the stable paclitaxel-human serum albumin of disulfide bond and wrap nano-particle.The mean diameter of prepared nanoparticle is 50～400nm, and HPLC analyzes and shows that the paclitaxel carried medicine amount of this experiment reaches 10%.
Claims (7)
1. a method of preparing stable albumin nanometer rice grain, is characterized in that the method carries out as follows:
1) prepare the albumin aqueous solution that volume mass concentration is 10～200mg/mL;
2) in albumin aqueous solution, add glutathion or cysteine, make its molar concentration in albumin aqueous solution reach 10～500mM, at 10～60 ℃ of temperature, react 5～240min;
3) in step 2) add ethanol or the tert-butyl alcohol in reacted solution, at 10～60 ℃ of temperature, react 5～120min, obtain the suspension of the crosslinked albumin nanometer rice grain of intermolecular disulfide bond; Described albumin aqueous solution is 1:1～5 with the volume ratio of the ethanol adding or the tert-butyl alcohol;
4) by the dialysis at 0～20 ℃ of temperature of the suspension of albumin nanometer rice grain, obtain albumin nanoparticles solution, then through lyophilization, spraying is dry or processed is carried out in distilling under reduced pressure, obtains albumin nanometer rice grain.
2. a kind of method of preparing stable albumin nanometer rice grain according to claim 1, is characterized in that: described albumin nano granular mean diameter is 10～500nm.
3. a kind of method of preparing stable albumin nanometer rice grain according to claim 1, is characterized in that: described albumin comprises human serum albumin, bovine serum albumin, recombination human serum albumin or their combination.
4. for sending a preparation method for the albumin nanometer rice grain of pharmacologically active medicine in body, it is characterized in that the method carries out as follows:
1) prepare the albumin aqueous solution that volume mass concentration is 10～200mg/mL;
2) in albumin aqueous solution, add glutathion or cysteine, make its molar concentration in albumin aqueous solution reach 10～500mM, at 10～60 ℃ of temperature, react 5～240min;
3) in step 2) add the t-butanol solution of alcoholic solution or the active medicine of pharmacologically active medicine in reacted solution, at 10～60 ℃ of temperature, react 5～120min, obtain wrapping up the suspension of the albumin nanometer rice grain of pharmacological active substance; Described albumin aqueous solution is 1:1～5 with the volume ratio of the alcoholic solution of the pharmacologically active medicine adding or the t-butanol solution of pharmacologically active medicine;
4) by the dialysis at 0～20 ℃ of temperature of the suspension of albumin nanometer rice grain, obtain wrapping up the solution of the albumin nanometer rice grain of pharmacological active substance, process lyophilization again, spraying are dried or processed is carried out in distilling under reduced pressure, obtain wrapping up the albumin nanometer rice grain of pharmacological active substance.
5. according to claim 4 a kind of for sending the preparation method of the albumin nanometer rice grain of pharmacologically active medicine in body, it is characterized in that: the pharmacological active substance that in described albumin nano granular, bag carries accounts for 1%～90% of nanoparticle total amount.
6. according to claim 4 a kind of for sending the preparation method of the albumin nanometer rice grain of pharmacologically active medicine in body, it is characterized in that: described pharmacological active substance is cancer therapy drug.
7. according to claim 6 a kind of for sending the preparation method of the albumin nanometer rice grain of pharmacologically active medicine in body, it is characterized in that: described cancer therapy drug comprises paclitaxel, Docetaxel, amycin, curcumin, platinum, methotrexate or their combination.
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| CN103520734B (en) * | 2013-09-29 | 2016-01-20 | 中国科学院过程工程研究所 | A kind of based on albuminous nanoparticle, Preparation Method And The Use |
| CN104043135B (en) * | 2014-06-13 | 2017-05-24 | 苏州大学 | Albumin indocyanine green paclitaxel compound as well as preparation method and application thereof |
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| CN109771656A (en) * | 2019-03-12 | 2019-05-21 | 四川载荧生物科技有限公司 | The preparation method of Novel albumin Nano medication under a kind of 37 DEG C of temperate conditions |
| CN110496229B (en) * | 2019-09-16 | 2022-09-23 | 上海市肺科医院 | Nanoparticle-coated antibacterial peptide with slow release property and preparation method thereof |
| CN111407741A (en) * | 2020-03-23 | 2020-07-14 | 太原理工大学 | Anti-cancer drug carrier with redox and pH dual responses and preparation method and application thereof |
| CN111529506B (en) * | 2020-05-18 | 2021-09-03 | 同济大学 | Amphotericin B albumin nano preparation and preparation method and application thereof |
| KR20230154864A (en) * | 2021-03-05 | 2023-11-09 | 씨에스피씨 종콰이 팔마씨우티컬 테크놀로지 (스자좡) 컴퍼니 리미티드 | Stable docetaxel albumin nanoparticle composition |
| CN113456612A (en) * | 2021-06-21 | 2021-10-01 | 上海市胸科医院 | Albumin drug delivery system for treating sepsis myocardial injury |
| CN115887677B (en) * | 2022-11-03 | 2024-04-12 | 嘉兴学院 | Preparation method and application of protein bionic capsules |
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| US6753006B1 (en) * | 1993-02-22 | 2004-06-22 | American Bioscience, Inc. | Paclitaxel-containing formulations |
| CN102048695A (en) * | 2009-08-11 | 2011-05-11 | 南京大学 | Preparation method of protein nanoparticle for in vivo delivery of pharmacologically active agent |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6753006B1 (en) * | 1993-02-22 | 2004-06-22 | American Bioscience, Inc. | Paclitaxel-containing formulations |
| CN102048695A (en) * | 2009-08-11 | 2011-05-11 | 南京大学 | Preparation method of protein nanoparticle for in vivo delivery of pharmacologically active agent |
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