CN103877024A - Preparation method of multifunctional liposome vesicle - Google Patents
Preparation method of multifunctional liposome vesicle Download PDFInfo
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- CN103877024A CN103877024A CN201410156810.6A CN201410156810A CN103877024A CN 103877024 A CN103877024 A CN 103877024A CN 201410156810 A CN201410156810 A CN 201410156810A CN 103877024 A CN103877024 A CN 103877024A
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Abstract
The invention belongs to the technical field of nanometer supermolecular materials. A liposome vesicle which is non-covalently bonded, good in biocompatibility and high in stability and can realize the functions of targeted transmission and monitoring tracking is prepared by adding amphiphilic p-sulfonated calix [4] arene in proper proportion on the basis that the liposome vesicle is prepared through the traditional phospholipid molecule and cholesterol. The preparation method disclosed by the invention has the advantages of easiness, convenience, small usage amount of main and object raw materials and wide application prospect in the field of targeted transportation of cancer medicines.
Description
[technical field]
The invention belongs to Nanosized Supramolecular Materials Composed of Host technical field, particularly a kind of Multifunction liposome vesicle and preparation method thereof.
[background technology]
In recent years, multi-functional vesicle receives much concern in fields such as biotechnology, medical diagnosis, drug delivery.Its main cause is; vesicle has the structure similar with cell membrane; and can wrap and carry hydrophilic molecule chamber in the inner; bag carries hydrophobic molecule (J. Nicolas, S. Mura, D. Brambilla among its hydrophobic film layer simultaneously; N. Mackiewicz; P. Couvreur. Chem. Soc. Rev. 2013,42,1147 – 1235; (2) M. Elsabahy, K. L. Wooley. Chem. Soc. Rev. 2012,41,2545 – 2561.).Common functional method is by by functionalization group; such as targeting agent and fluorescent probe etc.; be connected to by covalent bond on the amphipathic molecule of constructing vesicle; the multi-functional vesicle of gained not only can be used for bio-imaging; also can be used for the medicine transmission fields such as targeted therapy (F. Gu; L. Zhang; B. A. Teply; N. Mann, A. Wang, A. F. Radovic-Moreno; R. Langer; O. C. Farokhzad. Proc. Natl. Acad. Sci. USA 2008,105,2586 – 2591; (2) S. Mitragotri, J. Lahann. Adv. Mater. 2012,24,3717 – 3723; (3) L. Chen, X. Zhao, Y. Lin, Y. Huang, Q. Wang. Chem. Commun. 2013,49,9678 – 9680.).But what this process need was loaded down with trivial details synthesizes, organic reagent and toxic compounds can be introduced to vesicle carrier, and then affect the biocompatibility of material.And, if change functional group, often need to re-start the synthetic of carrier, waste time and energy (W. Li, J. Du, K. Zheng, P. Zhang, Q. Hu, Y. Wang. Chem. Commun. 2014,50,1579 – 1581.).
Supermolecule non-covalent modification is method (S. Himmelein, V. Lewe, M. C. Stuart, B. J. Ravoo. Chem. Sci. 2014,5,1054 – 1058 that the another kind except covalent bond means is constructed multi-functional vesicle; (2) E. Kim, D. Kim, H. Jung, J. Lee, S. Paul, N. Selvapalam, Y. Yang, N. Lim, C. G. Park, K. Kim. Angew. Chem. Int. Ed. 2010,49,4405 – 4408.).Embed macro ring main body by constructing at vesicle in process, make its rich surface containing Subjective and Objective binding site.Thereby further make functional group be incorporated into surperficial functionalization (the U. Kauscher that realizes vesicle of vesicle with non-covalent form by host-guest interaction, M. C. Stuart, P. Dr ü cker, H. J. Galla, B. J. Ravoo. Langmuir 2013,29,7377 – 7383.).The method has not only been avoided the numerous and diverse synthetic of vesicle skeleton, and can introduce quickly and easily variety classes functional group and realize the quantitative function of carrier.Conventional supermolecule macro ring main body has cyclodextrin, Cucurbituril and calixarenes etc.Amphipathic cyclodextrin vesicle and the Cucurbituril nanosphere water solublity reported are very poor, cannot realize long-time stablizing in water environment, have limited its application in medicine transmission field.Amphipathic calixarene is due to its good water solublity, (S. Kolusheva in the last few years received much attention in fields such as albumen identification, bio-sensing and gene transfections, R. Zadmard, T. Schrader, R. Jelinek. J. Am. Chem. Soc. 2006,128,13592 – 13598.).Wherein amphipathic Sulfonated calixarenes, due to its good binding ability and biocompatibility, is shown one's talent in numerous Calixarene Derivatives, but in the preparation of liposome vesicle rarely seen report also.
[summary of the invention]
The object of the invention is for above-mentioned technical Analysis, a kind of preparation method and functionalized application of multi-functional liposome vesicle is provided.This vesicle is made up of amphipathic sulfonation cup [4] aromatic hydrocarbons (SC4AB), phospholipid molecule (DPPC), cholesterol etc., good biocompatibility.Amphipathic sulfonation cup [4] aromatic hydrocarbons is embedded in vesicle surface, Subjective and Objective binding site is not only provided, make the vesicle can bonding cationic fluorescent probe and targeting agent and then practical function, and due to the embedding of Sulfonated calixarenes, thereby its sulfonate radical has reduced vesicle surface potential and has improved the stability of liposome vesicle in very big degree, its preparation method is easy, main, object raw material consumption is few.
Technical scheme of the present invention:
A kind of multi-functional liposome vesicle, its construction unit, taking phospholipid molecule (DPPC) and cholesterol as main, taking amphipathic sulfonation cup [4] aromatic hydrocarbons (SC4AB) as auxiliary, is constructed multi-functional liposome vesicle by close hydrophobic interaction.Amphipathic sulfonation cup [4] aromatic hydrocarbons provides Subjective and Objective binding site on liposome vesicle surface, can be used in conjunction with functionalization molecules such as cationic fluorescent probe and targeting agent.Its structure as shown in Figure 1.
A preparation method for described multi-functional liposome vesicle, step is as follows:
1) by DPPC and cholesterol according to amount of substance than 3:1, be dissolved in chloroform, making DPPC final concentration is 5 mmol/L, mixes rotary evaporation at rear 55-60 DEG C and obtains after liposome membrane, vacuum drying at least 6 hours at 15-20 DEG C;
2) adding with the isopyknic concentration of above-mentioned chloroform to above-mentioned liposome membrane is the SC4AB aqueous solution of 0.25～0.5 mmol/L, at 55-60 DEG C, stir 30 minutes, then ultrasonic 30 minutes of water-bath, is finally used 220 nm filters to remove bulky grain liposome, can make multi-functional liposome vesicle.
The application of above-mentioned liposome vesicle:
1, fluorescent probe is mixed homogeneously with vesicle solution, can make the liposome vesicle with fluorescence, this vesicle can detect by Laser Scanning Confocal Microscope, realizes monitoring and follows the tracks of.
2, targeting agent is mixed homogeneously with vesicle solution, can make the liposome vesicle that target cancer cell is had to targeting.This vesicle can be taken in by target cancer cell by receptor mediated endocytosis, realizes targeting transfer function.
3, fluorescent probe and targeting agent are mixed homogeneously with vesicle solution simultaneously, can make with fluorescence and target cancer cell be had to the liposome vesicle of targeting.This vesicle can detect by Laser Scanning Confocal Microscope, and is taken in by target cancer cell by receptor mediated endocytosis, realizes the function that targeting transmission and monitoring are followed the tracks of.
Therefore, multi-functional liposome vesicle provided by the invention can be applied to cancer drug targeting transport field.
Advantage of the present invention is: the present invention is that key component can be prepared multi-functional liposome vesicle by using common phospholipid molecule, cholesterol and amphipathic sulfonation cup [4] aromatic hydrocarbons, this liposome vesicle is that non-covalent combination, good biocompatibility, stability are high, and can realize targeting transmission and monitoring following function, this preparation method is easy, main, object raw material consumption is few, have broad application prospects at cancer drug targeting transport field.
[brief description of the drawings]
Fig. 1 is structure and the functional group schematic diagram of multi-functional liposome vesicle.
Fig. 2 is fixing phospholipid molecule concentration, and different amphipathic sulfonation cups [4] arene content light transmittance curve and 450nm place light transmittance change block diagram.
Fig. 3 is fixing phospholipid molecule concentration, different amphipathic sulfonation cups [4] arene content water and kinetic diameter variation diagram.
Fig. 4 is fixing phospholipid molecule concentration, the photo of different amphipathic sulfonation cups [4] arene content solution.
Fig. 5 is before and after multi-functional liposome vesicle functionalization and the dynamic light scattering particle size distribution figure of vesicle room temperature storage after 6 months.
Fig. 6 is the zeta potential numerical value of conventional liposome vesicle and multi-functional liposome vesicle and adds the zeta potential after methyl viologen object to change.
After Fig. 7 is conventional liposome and function liposome vesicle absorption fluorescent probe object, change in fluorescence figure in dialysis medium.
Fig. 8 is that amphipathic sulfonation cup [4] aromatic hydrocarbons of variable concentrations and MCF-7 cell are hatched cell survival rate figure two days later.
After Fig. 9 is multi-functional liposome vesicle absorption fluorescence molecule and targeting agent, hatch confocal microscope figure after 6 hours and the contrast with matched group thereof with MCF-7 cell.
[detailed description of the invention]
Embodiment 1:
A preparation method for described multi-functional liposome vesicle, step is as follows:
1) by DPPC and cholesterol according to amount of substance than 3:1, be dissolved in chloroform, making DPPC final concentration is 5 mmol/L, mixes rotary evaporation at rear 55-60 DEG C and obtains after liposome membrane, vacuum drying at least 6 hours at 15-20 DEG C;
2) adding with the isopyknic concentration of above-mentioned chloroform to above-mentioned liposome membrane is the SC4AB aqueous solution of 0.25 mmol/L, at 55-60 DEG C, stir 30 minutes, then ultrasonic 30 minutes of water-bath, is finally used 220 nm filters to remove bulky grain liposome, can make multi-functional liposome vesicle.
Embodiment 2
A preparation method for described multi-functional liposome vesicle, step is as follows:
1) by DPPC and cholesterol according to amount of substance than 3:1, be dissolved in chloroform, making DPPC final concentration is 5 mmol/L, mixes rotary evaporation at rear 55-60 DEG C and obtains after liposome membrane, vacuum drying at least 6 hours at 15-20 DEG C;
2) adding with the isopyknic concentration of above-mentioned chloroform to above-mentioned liposome membrane is the SC4AB aqueous solution of 0.5 mmol/L, at 55-60 DEG C, stir 30 minutes, then ultrasonic 30 minutes of water-bath, is finally used 220 nm filters to remove bulky grain liposome, can make multi-functional liposome vesicle.
Comparative example 1
A preparation method for conventional liposome vesicle, step is as follows:
1) by DPPC and cholesterol according to amount of substance than 3:1, be dissolved in chloroform, making DPPC final concentration is 5 mmol/L, mixes rotary evaporation at rear 55-60 DEG C and obtains after liposome membrane, vacuum drying at least 6 hours at 15-20 DEG C;
2) add and the isopyknic redistilled water of above-mentioned chloroform to above-mentioned liposome membrane, stir 30 minutes at 55-60 DEG C, ultrasonic 30 minutes of water-bath then, is finally used 220 nm filters to remove bulky grain liposome, can make conventional liposome vesicle.
Comparative example 2
A preparation method for Coliposomes micelle, step is as follows:
1) by DPPC and cholesterol according to amount of substance than 3:1, be dissolved in chloroform, making DPPC final concentration is 5 mmol/L, mixes rotary evaporation at rear 55-60 DEG C and obtains after liposome membrane, vacuum drying at least 6 hours at 15-20 DEG C;
2) adding with the isopyknic concentration of above-mentioned chloroform to above-mentioned liposome membrane is the SC4AB aqueous solution of 1 mmol/L, at 55-60 DEG C, stir 30 minutes, then ultrasonic 30 minutes of water-bath, is finally used 220 nm filters to remove bulky grain liposome, can make Coliposomes micelle.
The detection analysis of the liposome vesicle that above-described embodiment is obtained:
1, light transmittance detects, by measuring the light transmittance of above-mentioned gained liposome solutions at 450nm place, obtain result as shown in Figure 2: as shown in the figure, when SC4AB content exceedes 10%(amount of substance ratio) time, liposome solutions light transmittance obviously rises, show that liposome vesicle changes micelle into because SC4AB is excessive, this can prove by dynamic light scattering and naked-eye observation.
2, water and kinetic diameter detect, as shown in Figure 3, and when SC4AB content exceedes 10%(amount of substance ratio) time, liposome particle diameter obviously reduces, and has proved that liposome changes solid micelle into by hollow vesicle.
3, the photo of solution, as shown in Figure 4, when SC4AB content exceedes 10%(amount of substance ratio) time, liposome solutions becomes clarification from muddiness, proves that equally its imitated vesicle structure is destroyed.
Finally, the multi-functional liposome vesicle that is 10% to SC4AB content carries out the detection of dynamic light scattering particle size distribution, and obtaining its mean diameter is 87.4 nm, as shown in Figure 5.
Embodiment 3
A function derivatization method for described multi-functional liposome vesicle, step is as follows:
By 10 times of the multi-functional liposome vesicle solution dilutions preparing in embodiment 2, and add methyl viologen, its final concentration is 0.05 mmol/L, mixes.
Comparative example 3
By 10 times of the conventional liposome vesicle solution dilutions preparing in comparative example 1, and add methyl viologen, its final concentration is 0.05 mmol/L, mixes.
Embodiment 3 and comparative example 3 zeta potentials are detected, by measuring the zeta potential of above-mentioned gained liposome solutions, obtain result as shown in Figure 6: as shown in the figure, in multi-functional vesicle solution, add purpurine, due to the Subjective and Objective effect between purpurine and Sulfonated calixarenes, can make purpurine be adsorbed in vesicle surface, thereby improve the surface potential of vesicle.But, in conventional liposome, adding purpurine, surface potential does not have significant change, and this explanation purpurine is by Subjective and Objective effect bonding and vesicle surface.Meanwhile, multi-functional vesicle is compared with conventional liposome vesicle, potential value very low (26.82 mV), thus this improves the stability of vesicle for vesicle provides negative charge protective layer.Simultaneously by multi-functional vesicle in room temperature storage after 6 months, it is little that size and distributing all changes, as shown in Figure 5, and conventional liposome precipitates within a week, proves the stability that has greatly promoted liposome vesicle that adds of Sulfonated calixarenes.
Embodiment 4
A fluorescence derivation method for described multi-functional liposome vesicle, step is as follows:
In the multi-functional liposome vesicle solution preparing in embodiment 2, add fluorescent probe molecule (FITCPy), its final concentration is 0.05 mmol/L, mixes.
Comparative example 4
In the conventional liposome vesicle solution preparing in comparative example 1, add fluorescent probe molecule (FITCPy), its final concentration is 0.05 mmol/L, mixes.
Embodiment 4 and comparative example 4 are carried out to fluoroscopic examination.By above-mentioned gained liposome solutions is dialysed, and measure the fluorescence intensity of FITCPy in dialysis medium, obtain result as shown in Figure 7: as shown in the figure, after conventional liposome mixes with fluorescent probe, by dialysis, can soon probe molecule be removed to fluorescence fast rise in the medium of dialysing; But, after the multi-functional liposome that contains Sulfonated calixarenes mixes with fluorescent probe, by dialysis, probe molecule is removed slower, the fluorescence in medium of dialysing rises slowly, illustrates that fluorescence molecule is combined with vesicle by Subjective and Objective effect, has realized the fluorescent functional of vesicle.
Amphipathic sulfonation cup [4] aromatic hydrocarbons is carried out to cytotoxicity detection, obtain result as shown in Figure 8: as shown in the figure, amphipathic sulfonation cup [4] aromatic hydrocarbons of variable concentrations and MCF-7 cell (human breast cancer cell) are hatched cell survival rate two days later and all maintained 100% left and right.Experimental result shows, this amphiphilic Sulfonated calixarenes is biocompatible, can be used to medicine transmission field.
The fluorescence derivation of described multi-functional liposome vesicle and a target function derivatization method, step is as follows:
In the multi-functional liposome vesicle solution preparing in embodiment 2, add fluorescent probe molecule (FITCPy), its final concentration is 0.25 mmol/L, and targeting agent molecule (BtPy), and its final concentration is 0.25 mmol/L, mixes.
After Fig. 9 is multi-functional liposome vesicle absorption fluorescence molecule and targeting agent, hatch confocal microscope figure after 6 hours and the contrast with matched group thereof with MCF-7 cell.As shown in the figure, the vesicle of functionalization and MCF-7 cell are hatched (PCB+BtPy group) after 6 hours, present stronger fluorescence in cell; Test as a comparison, in the time lacking targeting agent, fluorescence very weak (PCB group) in cell; And if first use the saturated cell surface target site of biotin, then add the vesicle (biotin+PCB+BtPy group) of functionalization, in cell, fluorescence is equally very weak; If only add fluorescent probe molecule when cell is hatched, in cell, fluorescence is still very weak.Above result shows, through the vesicle of functionalization, can make it have fluorescence property by surface bond fluorescence molecule; After the agent of bonding targeting, the endocytosis that can make vesicle pass through receptor-inducible is fully taken in by tumor cell.In sum, thus this vesicle can be realized through simple mixing and absorption functionalization object by Subjective and Objective effect the function derivatization of vesicle in vesicle surface.
Claims (2)
1. a preparation method for multi-functional liposome vesicle, is characterized in that: the method comprises the following steps:
1) by DPPC and cholesterol according to amount of substance than 3:1, be dissolved in chloroform, making DPPC final concentration is 5 mmol/L, mixes rotary evaporation at rear 55-60 DEG C and obtains after liposome membrane, vacuum drying at least 6 hours at 15-20 DEG C;
2) adding with the isopyknic concentration of above-mentioned chloroform to above-mentioned liposome membrane is the SC4AB aqueous solution of 0.25～0.5 mmol/L, at 55-60 DEG C, stir 30 minutes, then ultrasonic 30 minutes of water-bath, is finally used 220 nm filters to remove bulky grain liposome, can make multi-functional liposome vesicle.
2. the one of multi-functional liposome vesicle according to claim 1 application, is characterized in that, multi-functional liposome vesicle provided by the invention is applied to cancer drug targeting transport field.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104888225A (en) * | 2015-06-12 | 2015-09-09 | 南开大学 | Covalent cross-linked nano-vesicle and preparation method thereof |
| CN108324958A (en) * | 2018-05-17 | 2018-07-27 | 陕西师范大学 | A kind of preparation method of purpurine 18- liposome nano vesicles and the application in preparing for tumor |
| CN110563829A (en) * | 2019-09-17 | 2019-12-13 | 中国人民解放军国防科技大学 | Light-reflecting protein system for regulating and controlling liposome vesicle behavior and function and application thereof |
| WO2022237466A1 (en) * | 2021-05-08 | 2022-11-17 | 深圳市第二人民医院(深圳市转化医学研究院) | Drug-carrying system, preparation method therefor, and pharmaceutical composition |
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| CA2361914A1 (en) * | 2001-11-13 | 2003-05-13 | Lawrence Mayer | Improved cholesterol-free liposomes |
| US20050008687A1 (en) * | 2003-07-07 | 2005-01-13 | Makoto Yuasa | Metal-porphyrin-complex-embedded liposomes, production process thereof, and medicines making use of the same |
| CN1698611A (en) * | 2005-06-07 | 2005-11-23 | 华东理工大学 | Nanometer vauqueline liposome and preparation method thereof |
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2014
- 2014-04-18 CN CN201410156810.6A patent/CN103877024B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2361914A1 (en) * | 2001-11-13 | 2003-05-13 | Lawrence Mayer | Improved cholesterol-free liposomes |
| US20050008687A1 (en) * | 2003-07-07 | 2005-01-13 | Makoto Yuasa | Metal-porphyrin-complex-embedded liposomes, production process thereof, and medicines making use of the same |
| CN1698611A (en) * | 2005-06-07 | 2005-11-23 | 华东理工大学 | Nanometer vauqueline liposome and preparation method thereof |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104888225A (en) * | 2015-06-12 | 2015-09-09 | 南开大学 | Covalent cross-linked nano-vesicle and preparation method thereof |
| CN104888225B (en) * | 2015-06-12 | 2017-07-11 | 南开大学 | A kind of nano vesicle of covalent cross-linking and preparation method thereof |
| CN108324958A (en) * | 2018-05-17 | 2018-07-27 | 陕西师范大学 | A kind of preparation method of purpurine 18- liposome nano vesicles and the application in preparing for tumor |
| CN108324958B (en) * | 2018-05-17 | 2021-09-24 | 陕西师范大学 | Preparation method of purpurin 18-liposome nano-vesicles and application of purpurin 18-liposome nano-vesicles in preparation of drugs for treating tumors |
| CN110563829A (en) * | 2019-09-17 | 2019-12-13 | 中国人民解放军国防科技大学 | Light-reflecting protein system for regulating and controlling liposome vesicle behavior and function and application thereof |
| WO2022237466A1 (en) * | 2021-05-08 | 2022-11-17 | 深圳市第二人民医院(深圳市转化医学研究院) | Drug-carrying system, preparation method therefor, and pharmaceutical composition |
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