CN107213116A - It is a kind of to improve the method that liposome carries doxorubicin hydrochloride content - Google Patents

It is a kind of to improve the method that liposome carries doxorubicin hydrochloride content Download PDF

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Publication number
CN107213116A
CN107213116A CN201710317310.XA CN201710317310A CN107213116A CN 107213116 A CN107213116 A CN 107213116A CN 201710317310 A CN201710317310 A CN 201710317310A CN 107213116 A CN107213116 A CN 107213116A
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China
Prior art keywords
liposome
doxorubicin hydrochloride
gradient
quantum dot
mentioned
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CN201710317310.XA
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Inventor
邓小勇
郦成
杭明光
徐姣姣
谢志全
段俊红
付朝
常庆
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University of Shanghai for Science and Technology
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University of Shanghai for Science and Technology
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
    • A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
    • A61K31/704—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/02—Inorganic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00—Preparations for testing in vivo
    • A61K49/001—Preparation for luminescence or biological staining
    • A61K49/0063—Preparation for luminescence or biological staining characterised by a special physical or galenical form, e.g. emulsions, microspheres
    • A61K49/0065—Preparation for luminescence or biological staining characterised by a special physical or galenical form, e.g. emulsions, microspheres the luminescent/fluorescent agent having itself a special physical form, e.g. gold nanoparticle
    • A61K49/0067—Preparation for luminescence or biological staining characterised by a special physical or galenical form, e.g. emulsions, microspheres the luminescent/fluorescent agent having itself a special physical form, e.g. gold nanoparticle quantum dots, fluorescent nanocrystals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00—Preparations for testing in vivo
    • A61K49/001—Preparation for luminescence or biological staining
    • A61K49/0063—Preparation for luminescence or biological staining characterised by a special physical or galenical form, e.g. emulsions, microspheres
    • A61K49/0069—Preparation for luminescence or biological staining characterised by a special physical or galenical form, e.g. emulsions, microspheres the agent being in a particular physical galenical form
    • A61K49/0076—Preparation for luminescence or biological staining characterised by a special physical or galenical form, e.g. emulsions, microspheres the agent being in a particular physical galenical form dispersion, suspension, e.g. particles in a liquid, colloid, emulsion
    • A61K49/0084—Preparation for luminescence or biological staining characterised by a special physical or galenical form, e.g. emulsions, microspheres the agent being in a particular physical galenical form dispersion, suspension, e.g. particles in a liquid, colloid, emulsion liposome, i.e. bilayered vesicular structure
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • A61K9/127—Liposomes
    • A61K9/1271—Non-conventional liposomes, e.g. PEGylated liposomes, liposomes coated with polymers

Abstract

The method that liposome carries doxorubicin hydrochloride content can be improved the invention discloses a kind of, this method in liposome inside and outside by building pH gradient, and graphene quantum dot is wrapped up simultaneously in aqueous phase in the film of liposome, more doxorubicin hydrochlorides can be made to enter by pH gradient in liposome, and be stable in the presence of with graphene quantum dot the interior aqueous phase of liposome；Liposome solutions are placed in the bag filter physiological saline that molecular cut off is 3,500 6~the 7h that dialyses, obtain the liposome solutions of pH gradient, then 2~3ml is contained into 3~4mmol/L doxorubicin hydrochloride solution and is added in the above-mentioned liposome solutions for having a pH gradient 2~3h of incubation reaction in 60~65 DEG C of water-bath, obtain carrying the liposome of doxorubicin hydrochloride；Liposome carrier band doxorubicin hydrochloride content prepared by this method is high, due to there is graphene quantum dot in liposome, and liposome imaging and fluorescence analysis of the quantum dot to carry doxorubicin hydrochloride provide reliable, convenient detection means.

Description

It is a kind of to improve the method that liposome carries doxorubicin hydrochloride content
Technical field
The method that liposome carries doxorubicin hydrochloride content can be improved the present invention relates to a kind of.
Background technology
Graphene quantum dot（GQDs it is) a kind of zero dimension graphite alkenes carbon material, with significant quantum confined effect and side Edge effect, due to its unique optical property, good biocompatibility, water-soluble and relatively low toxicity, it is possible to be applied to Bio-imaging, fluorescence analysis and medicine carrier band technical field.
Doxorubicin hydrochloride is a kind of anthracycline antibiotic medicine, it is adaptable to lung cancer, breast cancer, the kinds cancer such as thyroid cancer Treatment.But larger side effect may be produced to human body using doxorubicin hydrochloride, the threat to heart is especially big.Liposome It is a kind of artificial membrane, hydrophobic tail is connected in water by phospholipid molecule, in hydrophilic head insertion water, curls into double points The miniature vesica of sublayer.Medicine can be sent into cell interior with cell membrane fusion using liposome, use liposome salt Sour adriamycin, increase doxorubicin hydrochloride not only improves drug effect, while can reduce medicine to human body in the enrichment of tumor locus Harm.
Improving the method for doxorubicin hydrochloride encapsulation efficiency in liposome at present mainly has following several：One is to change lipid The preparation prescription of body, the composition of liposome is typically made up of phosphatide and cholesterol, changes different phosphatide and cholesterol in prescription Mol ratio, so as to change the property of the liposome of preparation, influences the encapsulating content of doxorubicin hydrochloride；Two be to utilize different load medicines Technology, for example, active loading method, with building ion gradient or pH gradient outside film in the film of liposome bilayers film, makes More directions of the doxorubicin hydrochloride along gradient from low to high, enter in film outside liposome membrane on one's own initiative, are formed in film Stable precipitation or compound；Three be to change the technological parameter in liposome doxorubicin hydrochloride preparation process, such as sharp When being prepared with film aquation method change hydrated films time, ultrasonic method reduce liposomal particle size when change ultrasound power or Change pattern of ultrasound etc., still, the above method has many deficiencies, the physics and chemistry of liposome can be influenceed by for example changing prescription Matter, the change of technological parameter can cause liposomal particle size heterogeneity, and encapsulation efficiency improves DeGrain, and influence liposome Distribution in vivo.In addition, how to carry other drugs using the liposome for being loaded with doxorubicin hydrochloride, multi-medicament is realized Therapeutic alliance is also the problem of needing to solve.
The content of the invention
The method that liposome carries doxorubicin hydrochloride content, this method energy can be improved it is an object of the invention to provide a kind of So that more medicines enter in liposome, and are stable in the presence of the interior aqueous phase of liposome with graphene quantum dot, so as to improve Encapsulating content of the doxorubicin hydrochloride in liposome.
To reach above-mentioned purpose, the technical solution adopted by the present invention is as follows：
A kind of to improve the method that liposome carries doxorubicin hydrochloride content, its step is as follows：
(1) is by a certain amount of carbon fiber（CF) it is immersed in a certain amount of nitration mixture, room temperature ultrasound 1-2 hours, reheats backflow 18-36 hours, described nitration mixture was 98% concentrated sulfuric acid and the mixture of 63% concentrated nitric acid, H2SO4: HNO3=(3~4): 1；Instead Should after be cooled to room temperature, above-mentioned reaction solution is poured into deionized water, described reaction solution and the volume ratio of deionized water are 5-10；Dialysed 5~7 days for 3500 bag filter with molecular cut off again, obtain graphene quantum dot (GQDs) solution；
(2) 188~376 mg hydrogenated soya phosphatides HSPC of weighings, 46~92 mg high net cholesterol CHO and 34~68 mg bis- are hard Fatty acyl group phosphatidyl-ethanolamine-polyethylene glycol (DSPE-PEG2000) mixing, said mixture is added into said mixture 3~5 Dissolved in mL chloroform and 1mL methanol；Then 600~700 above-mentioned solution of μ L are measured, are added to 100~200mL's It is that 200~400 rpm temperature are to be rotated on 60~65 DEG C of Rotary Evaporators in rotating speed in pear shape bottle, revolving 30~ 45min, removes organic solvent, and one layer of liposome membrane is formed in the bottom of pear shape bottle；
(3) is by 4~5 300~350mmol/L of mL ammonium sulfate and 0.2~0.3 mg/mL graphene quantum dot (IGQDs) solution is added in the above-mentioned pear shape bottle for having a liposome membrane, and pear shape bottle is placed in shaking table carries out hydration reaction, Rotating speed is 220~300 rpm, vibrates 0.5~1 h, and the hydrated films taken out in pear shape bottle are placed in water bath sonicator instrument, ultrasound point 10~20 min are dissipated, make its fully dispersed, then, the liposome solutions after disperseing extrude 10 by the extruding of liposome squeezer Back and forth, liposome is obtained；
(4) liposome solutions after 2mL above-mentioned extrusion are placed on the bag filter physiological saline that molecular cut off is 3500 by 6~7h of middle dialysis, obtains the liposome solutions of pH gradient, then that the mmol/L doxorubicin hydrochlorides of 2~3 ml 3~4 is molten Liquid is added in the above-mentioned liposome solutions for having a pH gradient 2~3h of incubation reaction in 60~65 DEG C of water-bath, obtains carrying salt The liposome of sour adriamycin.
The present invention compared with prior art, has the following advantages that：
(1) this method is by building pH gradient in liposome inside and outside, and wraps up graphene quantum dot simultaneously in liposome Aqueous phase in film, makes more doxorubicin hydrochlorides enter by pH gradient in liposome, and be stable in the presence of with graphene quantum dot The interior aqueous phase of liposome, improves encapsulation efficiency of the carrier band doxorubicin hydrochloride in liposome, the presence of graphene quantum dot is not only It is that bio-imaging and fluorescence analysis provide detection means, other drugs can also be carried by graphene quantum dot, realize fat Common carrier band of the plastid to multi-medicament, it is contemplated that realize treated with combined medication.
(2) this method is easy to operate, without accessory substance, and unsupported medicine is easily isolated；
(3) the liposome carrier band doxorubicin hydrochloride content that prepared by this method is improved, by purple of the doxorubicin hydrochloride at 488 nm The content that outer absorption standard concentration curve calculates doxorubicin hydrochloride in the liposome for carrying doxorubicin hydrochloride is 2.92 mg, i.e., 2.92 mg are brought up to from 2.56 mg.
Brief description of the drawings
Fig. 1 is obtained in the embodiment of the present invention a kind of to improve the liposome that liposome carries doxorubicin hydrochloride content (TEM) picture of transmission electron microscope.
Embodiment
The present invention is described in further detail below in conjunction with accompanying drawing embodiment.
The a kind of of the present embodiment can improve the method that liposome carries doxorubicin hydrochloride content, comprise the following steps that：
(1) a certain amount of carbon fiber (CF) is immersed in a certain amount of nitration mixture by, room temperature ultrasound 1 hour, reheats backflow 18 Hour, described nitration mixture is 98% concentrated sulfuric acid and the mixture of 63% concentrated nitric acid, H2SO4: HNO3= 3 : 1；It is cooled to after reaction Room temperature, above-mentioned reaction solution is poured into deionized water, and described reaction solution and the volume ratio of deionized water are 5；Again with retention Molecular weight is dialysed 5 days for 3500 bag filter, obtains graphene quantum dot (GQDs) solution；
(2) weighs 188 mg hydrogenated soya phosphatides HSPC, the high net cholesterol CHO of 46 mg and 34 mg distearyl acyl group phosphatidyls Monoethanolamine-polyethylene glycol (DSPE-PEG2000) mixing, said mixture is added to row in 3 mL chloroform and 1mL methanol molten Solution；Then the 600 above-mentioned solution of μ L are measured, are added in 100mL pear shape bottle, are the rotation that 200 rpm temperature are 60 DEG C in rotating speed Turn to be rotated on evaporimeter, rotate 30 min, remove organic solvent, one layer of liposome membrane is formed in the bottom of pear shape bottle；
(3) the graphene quantum dot solution of 4mL 300mmol/L ammonium sulfate and 0.2 mg/mL is added to by above-mentioned has lipid In the pear shape bottle of body thin film, and pear shape bottle is placed in shaking table carries out hydration reaction, rotating speed is 220 rpm, vibrates 1 h, is taken out Hydrated films in pear shape bottle are placed in water bath sonicator instrument, the min of ultrasonic disperse 10, make its fully dispersed, then, after disperseing Liposome solutions obtain liposome for 10 back and forth by liposome squeezer extruding extrusion；
(4) liposome solutions after 2mL above-mentioned extrusion are placed on the bag filter physiological saline that molecular cut off is 3500 by 6 h of middle dialysis, obtain the liposome solutions of pH gradient, then add 2ml concentration for 3mmol/L doxorubicin hydrochlorides solution Into the above-mentioned liposome solutions for having a pH gradient in 60 DEG C of water-bath the h of incubation reaction 2, obtain carrying the fat of doxorubicin hydrochloride Plastid；
(5) liposome of thick carrier band medicine doxorubicin hydrochloride obtained above is put into glucan G-50 gel columns by, and elution is removed Free adriamycin, the liposome for the carrier band medicine doxorubicin hydrochloride being further purified, as shown in Figure 1；Then, using ultraviolet Spectrophotometric measures the absorption value at 488 nm, is calculated by UV absorption standard concentration curve of the doxorubicin hydrochloride at 488 nm The content for going out to carry doxorubicin hydrochloride in the liposome of doxorubicin hydrochloride is 2.92 mg, or encapsulation efficiency is that parcel enters lipid The percentage of doxorubicin hydrochloride total amount of the doxorubicin hydrochloride total amount of body with being incubated liposome solutions, is 89.7%.It is of the invention used Ultraviolet specrophotometer production firm is HIT, model U-3010.

Claims (1)

1. a kind of can improve the method that liposome carries doxorubicin hydrochloride content, it is characterised in that this method step is as follows：
（1）By a certain amount of carbon fiber（CF）It is immersed in a certain amount of nitration mixture, room temperature ultrasound 1-2 hours, reheats backflow 18- 36 hours, described nitration mixture was 98% concentrated sulfuric acid and the mixture of 63% concentrated nitric acid, H2SO4: HNO3=(3~4): 1；After reaction Room temperature is cooled to, above-mentioned reaction solution is poured into deionized water, described reaction solution and the volume ratio of deionized water are 5-10； Dialysed 5~7 days for 3500 bag filter with molecular cut off again, obtain graphene quantum dot (GQDs) solution；
（2）Weigh 188~376 mg hydrogenated soya phosphatides HSPC, 46~92 mg high net cholesterol CHO and 34~48 mg bis- hard Fatty acyl group phosphatidyl-ethanolamine-polyethylene glycol (DSPE-PEG2000) mixing, said mixture is added into said mixture 3~5 Dissolved in mL chloroform and 1mL methanol；Then 600~700 above-mentioned solution of μ L are measured, are added to 100~200mL's It is that 200~400 rpm temperature are to be rotated on 60~65 DEG C of Rotary Evaporators in rotating speed in pear shape bottle, revolving 30~45 Min, removes organic solvent, and one layer of liposome membrane is formed in the bottom of pear shape bottle；
（3）4~5mL, 300~350mmol/L ammonium sulfate and 0.2~0.3 mg/mL graphene quantum dot (IGQDs) is molten Liquid is added in the above-mentioned pear shape bottle for having a liposome membrane, and pear shape bottle is placed in shaking table carries out hydration reaction, and rotating speed is 220 ~300 rpm, vibrate 0.5~1h, and the hydrated films taken out in pear shape bottle are placed in water bath sonicator instrument, ultrasonic disperse 10~20 Min, makes its fully dispersed, then, and the liposome solutions after disperseing extrude 10 back and forth by the extruding of liposome squeezer, obtain Liposome；
（4）Liposome solutions after 2mL above-mentioned extrusion are placed in the bag filter physiological saline that molecular cut off is 3500 Dialyse 6~7h, obtains the liposome solutions of pH gradient, then adds 2~3ml, 3~4mmol/L doxorubicin hydrochloride solution Enter into the above-mentioned liposome solutions for having a pH gradient 2~3h of incubation reaction in 60~65 DEG C of water-bath, obtain carrier band hydrochloric acid Ah The liposome of mycin.
CN201710317310.XA 2017-05-08 2017-05-08 It is a kind of to improve the method that liposome carries doxorubicin hydrochloride content Pending CN107213116A (en)

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108328610A (en) * 2018-04-28 2018-07-27 卢伟 A kind of preparation method and applications of liposome modification nano-graphene
CN108892131A (en) * 2018-09-28 2018-11-27 华南师范大学 A kind of graphene quantum dot and preparation method thereof
CN109276542A (en) * 2018-11-05 2019-01-29 上海市第六人民医院 A kind of carbon dots photo-thermal therapy reagent and preparation method thereof of near-infrared response
CN110025576A (en) * 2019-04-23 2019-07-19 上海市第六人民医院 A kind of preparation method and applications of the photothermal reagent of the photo-thermal oncotherapy mediated for fluorescence imaging
CN112168981A (en) * 2019-07-02 2021-01-05 西安电子科技大学 Switch type liposome nano fluorescent probe and preparation method and application thereof
CN113559063A (en) * 2021-05-11 2021-10-29 上海大学 Method for efficiently loading graphene quantum dots on liposome and composite material prepared by method

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US20150216975A1 (en) * 2007-10-03 2015-08-06 William Marsh Rice University Nanovector based drug delivery system for overcoming drug resistance
CN105535996A (en) * 2016-01-08 2016-05-04 贵州医科大学 Novel fluorescence lipidosome nano probe and preparing method thereof
CN105948021A (en) * 2016-04-23 2016-09-21 上海大学 Method for preparing nitrogen-doped graphene quantum dots by using high-power electron beam irradiation process

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20150216975A1 (en) * 2007-10-03 2015-08-06 William Marsh Rice University Nanovector based drug delivery system for overcoming drug resistance
CN102485211A (en) * 2010-12-01 2012-06-06 沈阳药科大学 Doxorubicin liposome and its preparation method
CN105535996A (en) * 2016-01-08 2016-05-04 贵州医科大学 Novel fluorescence lipidosome nano probe and preparing method thereof
CN105948021A (en) * 2016-04-23 2016-09-21 上海大学 Method for preparing nitrogen-doped graphene quantum dots by using high-power electron beam irradiation process

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108328610A (en) * 2018-04-28 2018-07-27 卢伟 A kind of preparation method and applications of liposome modification nano-graphene
CN108328610B (en) * 2018-04-28 2021-10-08 丁道其 Preparation method and application of liposome modified nano graphene
CN108892131A (en) * 2018-09-28 2018-11-27 华南师范大学 A kind of graphene quantum dot and preparation method thereof
CN109276542A (en) * 2018-11-05 2019-01-29 上海市第六人民医院 A kind of carbon dots photo-thermal therapy reagent and preparation method thereof of near-infrared response
CN110025576A (en) * 2019-04-23 2019-07-19 上海市第六人民医院 A kind of preparation method and applications of the photothermal reagent of the photo-thermal oncotherapy mediated for fluorescence imaging
CN112168981A (en) * 2019-07-02 2021-01-05 西安电子科技大学 Switch type liposome nano fluorescent probe and preparation method and application thereof
CN113559063A (en) * 2021-05-11 2021-10-29 上海大学 Method for efficiently loading graphene quantum dots on liposome and composite material prepared by method

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Application publication date: 20170929