CN104815332A - pH-responsive binary supramolecular nanoparticles, and preparation method and application thereof - Google Patents
pH-responsive binary supramolecular nanoparticles, and preparation method and application thereof Download PDFInfo
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Abstract
The invention relates to pH-responsive binary supramolecular nanoparticles. The construction unit uses sulfonated cyclodextrin as a host and chitosan as a guest, thereby constructing the supramolecular assembly under the host-guest electrostatic interactions. The preparation method comprises the following steps: dissolving the sulfonated cyclodextrin and chitosan in water, and uniformly mixing to obtain a binary supramolecular nanoparticle solution. As the pH value of the solution is gradually regulated to alkality, the assembly nanoparticles gradually are depolymerized; as the pH value of the solution is gradually regulated to acidity, the nanoparticles reform; the assembly nanoparticles have favorable circulating property for pH response; and the binary supramolecular nanoparticles are used for carrying trisodium 8-hydroxypyreny-1,3,6-trisulfonate. The preparation method of the nano supramolecular nanoparticles is simple and convenient. The prepared supramolecular nanoparticles have the advantages of favorable biocompatibility, favorable stability and favorable selection responsivity for pH, and create favorable conditions for specific carried drugs for treating diseases and the like.
Description
[technical field]
The invention belongs to Nanosized Supramolecular Materials Composed of Host technical field, binary supermolecule nano particle of particularly a kind of pH response and its preparation method and application.
[background technology]
Supermolecule nano particle in vivo and the field such as chemistry, biology, material science have extremely important and very important meaning, see 1) X.Zhang, S.Rehm, M.M.Safont-Sempere andF.W ü rthner, Nat.Chem., 2009,1,623 – 629; 2) A.Mueller and D.F.O'Brien, Chem.Rev., 2002,102,727 – 757; 3) D.M.Vriezema, M.C.Aragones, J.A.A.W.Elemans, J.J.L.M.Cornelissen, A.E.Rowan and R.J.M.Nolte, Chem.Rev., 2005,105,1445 – 1489.The medicine/gene transport system of stimuli responsive nanoparticle becomes one of them study hotspot owing to carrying medicament can be discharged the carrying out of specific site targeting, because this not only can improve the drug effect of carrying medicament, and can reduce its toxic and side effects.
By supramolecular chemistry means can be simple and effective obtain the supermolecule nano particle with stimuli responsive character, see 1) X.Zhang and C.Wang, Chem.Soc.Rev., 2011,40,94 – 101; 2) Xiao-Fang Hou, Yong Chen, and Yu Liu.Soft Matter, 2015,11,2488-2493.Current report stimuli responsive supermolecule nano particle great majority with calixarenes, Cucurbituril, post aromatic hydrocarbons etc. by main body is formed by noncovalent interaction and object effect, but the system utilizing anionic cyclodextrin to create supermolecule nano particle as main body is also little, see: 1) Yi-Xuan Wang, Ying-Ming Zhang, andYu Liu, J.Am.Chem.Soc., 2015,137,4543 – 4549; 2) Y.Liu, K.Liu, Z.Wang and X.Zhang, Chem. – Eur.J., 2011,17,9930 – 9935; 3) Y.Cao, X.Hu, Y.Li, X.Zou, S.Xiong, C.Lin, Y.Shen and L.Wang, J.Am.Chem.Soc., 2014,136,10762 – 10769.Cyclodextrin takes chair conformation to be formed by the connection of 1-4 glycosidic bond by D-(+)-Glucopyranose., therefore it has unique outstanding biocompatibility.Outstanding biocompatibility gives the bright prospects of nanoparticle in medicine carrying field.Therefore, the supermolecule nano particle system designed based on cyclodextrin is significant and broad prospect of application.
[summary of the invention]
The object of the invention is for above-mentioned technical Analysis and existing problems, binary supermolecule nano particle providing a kind of pH to respond and its preparation method and application, this supermolecule nano particle is the pH regulation and control nanoparticle based on sulfated cyclodextrins and chitosan binary Supramolecular Assembling, there is good biocompatibility, stability and to Acidity of Aikalinity response, and can by Cell uptake, at inclusion medicine, to the potential using value in drug controllable release etc.
Technical scheme of the present invention:
A kind of binary supermolecule nano particle of pH response; its construction unit is based on sulfated cyclodextrins (SCD); with chitosan (CS) for object; construct super-molecule assembling body by host-guest charge interaction, wherein chitosan is the chitosan of degree of deacetylation 95%.
A preparation method for the binary supermolecule nano particle of described pH response, step is as follows:
1) sulfated cyclodextrins is soluble in water, concentration is 1mM/mL, then regulates pH to 5.3 by the NaOH solution of 1mol/L, obtains sulfated cyclodextrins mother solution;
2) chitosan being dissolved in concentration is in the dilute acetic acid solution of 1v%, the amount ratio of chitosan and dilute acetic acid solution is 5mg:1mL, adding the amount ratio that water is settled to chitosan and dilute acetic acid solution is again 1mg:1mL, then regulate pH to 5.3 by the NaOH solution of 1mol/L, obtain chitosan mother solution;
3) pH NaOH solution of 1mol/L be added to the water to water is 5.3;
4) sulfated cyclodextrins mother solution is mixed with chitosan mother solution, add pH value be 5.3 the water concentration that is settled to sulfated cyclodextrins be 35mmol/mL, chitosan concentration is 0.01mg/mL, obtains the binary supermolecule nano particle solution that pH value is the pH response of 5.3.
The binary supermolecule nano particle solution of the pH response of preparation has response to pH, and when pH value of solution is alkalescence, nanoparticle realizes depolymerization; When pH value of solution is acid, nanoparticle is formed again, and this process has good past renaturation.
A kind of application of binary supermolecule nano particle of described pH response, for load module molecule 8-hydroxyl pyrene-1, 3, 6-trisulfonic acid trisodium salt (HPTS) also realizes controllable release, carrying method is: by 8-hydroxyl pyrene-1, 3, 6-trisulfonic acid trisodium salt (HPTS) is added drop-wise in the binary supermolecule nano particle solution containing sulfated cyclodextrins (SCD) and chitosan (CS), 8-hydroxyl pyrene-1 in solution, 3, 6-trisulfonic acid trisodium salt, the concentration of sulfated cyclodextrins and protamine is respectively 0.01mM, 35mmol/mL and 0.01mg/mL, then be 3500 bag filter dialysis purification by solution molecular cut off.
Advantage of the present invention is: this binary supermolecule nano particle is constructed based on sulfated cyclodextrins and chitosan binary Supramolecular Assembling, and preparation method is easy, main, object raw material dosage is few; The supermolecule nano particle bio-compatible of preparation and have good stability, has good response to pH, can load module molecule HPTS, is used for the treatment of disease creates favourable condition for this nanoparticle being applied in load certain drug.
[accompanying drawing explanation]
Fig. 1 is chitosan (CS) concentration when being 0.01mg/mL, the critical aggregation concentration figure of main body sulfated cyclodextrins (SCD).
Fig. 2 is sulfated cyclodextrins (SCD) concentration when being 0.035mmol/mL, the critical aggregation concentration figure of object chitosan (CS).
Fig. 3 is the dynamic light scattering figure of this binary supermolecule nano particle.
Fig. 4 is the high resolution transmission electron microscopy figure of this binary supermolecule nano particle.
Fig. 5 is the scanning electron microscope diagram of this binary supermolecule nano particle.
Fig. 6 is the ZETA potential diagram of this binary supermolecule nano particle.
Fig. 7 is this binary supermolecule nano particle 400nm wavelength place absorbance time history plot.
Fig. 8 is the temperature variant curve chart of this binary supermolecule nano particle 400nm wavelength place's absorbance.
Fig. 9 is the curve chart that this binary supermolecule nano particle 400nm wavelength place light transmittance changes with system pH.
Figure 10 is that this binary supermolecule nano particle 400nm wavelength place light transmittance is with the curve chart back and forth regulating solution acid-basicity and pH value change.
Figure 11 be this binary supermolecule nano particle condition system pH be 10.4 namely alkalescence time its nanoparticle depolymerization high resolution transmission electron microscopy figure.
Figure 12 is this binary supermolecule nano particle load Model Molecule HPTS stability fluorogram.
Figure 13 be this binary supermolecule nano particle preparation and to pH response schematic diagram.
[detailed description of the invention]
Embodiment:
A kind of binary supermolecule nano particle of pH response, its construction unit is based on sulfated cyclodextrins (SCD), with chitosan (CS) for object, construct super-molecule assembling body by host-guest charge interaction, wherein chitosan is the chitosan of degree of deacetylation 95%; Its preparation method, step is as follows:
1) sulfated cyclodextrins is soluble in water, concentration is 1mM/mL, then regulates pH to 5.3 by the NaOH solution of 1mol/L, obtains sulfated cyclodextrins mother solution;
2) chitosan being dissolved in concentration is in the dilute acetic acid solution of 1v%, the amount ratio of chitosan and dilute acetic acid solution is 5mg:1mL, adding the amount ratio that water is settled to chitosan and dilute acetic acid solution is again 1mg:1mL, then regulate pH to 5.3 by the NaOH solution of 1mol/L, obtain chitosan mother solution;
3) pH NaOH solution of 1mol/L be added to the water to water is 5.3;
4) 175 μ L sulfated cyclodextrins mother solutions are mixed with 50 μ L chitosan mother solutions, add pH value be 5.3 water be settled to 5mL, obtain pH value be 5.3 pH response binary supermolecule nano particle solution.
Fig. 1 is chitosan (CS) concentration when being 0.01mg/mL, and the critical aggregation concentration figure of main body sulfated cyclodextrins (SCD), shows in figure: the critical aggregation concentration of main body sulfated cyclodextrins (SCD) is 0.024mmol/mL.
Fig. 2 is sulfated cyclodextrins (SCD) concentration when being 0.035mmol/mL, the critical aggregation concentration figure of object chitosan (CS), show in figure: the critical aggregation concentration of chitosan (CS) is 0.01mg/mL, thus obtain the optimal accumulated concentration ratio of sulfated cyclodextrins and protamine.
The particle diameter of this binary supermolecule nano particle and pattern:
Characterize respectively by dynamic light scattering, high resolution transmission electron microscopy, scanning electron microscope and ZETA current potential.
Fig. 3 is the dynamic light scattering figure of the pH response nano particle of sulfated cyclodextrins and chitosan Supramolecular Assembling, shows in figure: nanoparticle mean diameter is 173.12nm.
Fig. 4 is the high resolution transmission electron microscopy figure of the enzyme response nano particle of sulfated cyclodextrins and chitosan Supramolecular Assembling; Fig. 5 is the scanning electron microscope diagram of the pH response nano particle of sulfated cyclodextrins and chitosan Supramolecular Assembling; Fig. 6 is the ZETA potential diagram of the nanoparticle of sulfated cyclodextrins and chitosan Supramolecular Assembling.Show in figure: nanoparticle surface current potential is-28.46mV.
Fig. 7 is the supermolecule nano particle system 400nm wavelength place absorbance time history plot of sulfated cyclodextrins and the chitosan assembling of constructing, show in figure: this binary supermolecule nano particle assembling body does not change in time substantially at the light transmittance at 400nm wavelength place, shows that this supermolecule nano particle has good stability.
Fig. 8 is the temperature variant curve chart of supermolecule nano particle system 400nm wavelength place's light transmittance of sulfated cyclodextrins and the chitosan assembling of constructing, show in figure: this binary supermolecule nano particle assembling body does not change with temperature increase substantially at the light transmittance at 400nm wavelength place, this supermolecule nano particle of surface has the stability well to temperature, the driving force that this supermolecule nano rice corpuscles visible is formed and positive and negative charge electrostatic attraction effect, and its change for temperature does not show response.
This binary supermolecule nano particle is to the response of pH:
The binary supermolecule nano particle solution of the pH response of preparation has response to pH, and when pH value of solution is alkalescence, nanoparticle realizes depolymerization; When pH value of solution is acid, nanoparticle is formed again, and this process has good past renaturation.
Fig. 9 is the supermolecule nano particle of the sulfated cyclodextrins constructed and chitosan assembling ties up to 400nm place light transmittance variation diagram at condition of different pH lower body, show in figure: time the initial pH of this binary supermolecule nano particle is 5.3, transmitance is minimum, along with adjustment pH value of solution is gradually to 6.32,8.02,10.40, can find out that its transmitance constantly rises, mean the depolymerization gradually of assembly; Again system pH being adjusted back to 5.30 gradually from 10.40, is 7.33,6.29 respectively through pH, can find out that solution shows downward trend again in the transmitance at 400nm place, means that solution is recalled to assembly acid process from alkalescence and again formed.
Figure 10 is the past renaturation experiment that the supermolecule nano particle of sulfated cyclodextrins and the chitosan assembling of constructing responds for pH, show in figure: this binary supermolecule nano particle show when initial pH is 5.3 obviously through, regulation system pH is to alkali condition 10.40, solution at 400nm place through obvious rising, mean the depolymerization of assembly, continue to regulate pH to 5.3, transmitance declines again, so move in circles, this supermolecule nano particle shows well moving in circles property for pH regulation and control as seen.
Figure 11 is supermolecule nano particle high-resolution-ration transmission electric-lens figure when pH regulator to 10.40 of sulfated cyclodextrins and the chitosan assembling of constructing, and shows in figure: when system pH regulator is to alkalescence, intuitively finds out nanoparticle depolymerization substantially completely.The nanoparticle that visible the present invention constructs has obvious response for pH.
The application of the binary supermolecule nano particle of prepared pH response, for load module molecule 8-hydroxyl pyrene-1, 3, 6-trisulfonic acid trisodium salt (HPTS) also realizes controllable release, carrying method is: by 8-hydroxyl pyrene-1, 3, 6-trisulfonic acid trisodium salt (HPTS) is added drop-wise in the binary supermolecule nano particle solution containing sulfated cyclodextrins (SCD) and chitosan (CS), 8-hydroxyl pyrene-1 in solution, 3, 6-trisulfonic acid trisodium salt, the concentration of sulfated cyclodextrins and protamine is respectively 0.01mM, 35mmol/mL and 0.01mg/mL, then be 3500 bag filter dialysis purification by solution molecular cut off.
Model Molecule HPTS load test:
HPTS full name is 8-hydroxyl pyrene-1,3,6-trisulfonic acid trisodium salt, and being that a kind of hydrophilic fluorescent material is purple, is Model Molecule with HPTS in this work, the sulfated cyclodextrins that load is constructed in the present invention and chitosan binary supermolecule nano inside particles.
Figure 12 is the stability experiment that HPTS is loaded in the binary supermolecule nano particle that sulfated cyclodextrins and chitosan construct, and shows in figure: HPTS be loaded in the binary supermolecule nano particle that sulfated cyclodextrins and chitosan construct after in 6h its fluorescence intensity not there is significant change.Can find out that the binary supermolecule nano particle constructed by the present invention is significant and potential using value in medicine carrying application afterwards.
Figure 13 be this binary supermolecule nano particle preparation and to pH response schematic diagram.
Claims (3)
1. the binary supermolecule nano particle of a pH response; it is characterized in that: construction unit is based on sulfated cyclodextrins (SCD); with chitosan (CS) for object; construct super-molecule assembling body by host-guest charge interaction, wherein chitosan is the chitosan of degree of deacetylation 95%.
2. a preparation method for the binary supermolecule nano particle of pH response as claimed in claim 1, is characterized in that step is as follows:
1) sulfated cyclodextrins is soluble in water, concentration is 1mM/mL, then regulates pH to 5.3 by the NaOH solution of 1mol/L, obtains sulfated cyclodextrins mother solution;
2) chitosan being dissolved in concentration is in the dilute acetic acid solution of 1v%, the amount ratio of chitosan and dilute acetic acid solution is 5mg:1mL, adding the amount ratio that water is settled to chitosan and dilute acetic acid solution is again 1mg:1mL, then regulate pH to 5.3 by the NaOH solution of 1mol/L, obtain chitosan mother solution;
3) pH NaOH solution of 1mol/L be added to the water to water is 5.3;
4) sulfated cyclodextrins mother solution is mixed with chitosan mother solution, add pH value be 5.3 the water concentration that is settled to sulfated cyclodextrins be 35mmol/mL, chitosan concentration is 0.01mg/mL, obtains the binary supermolecule nano particle solution that pH value is the pH response of 5.3.
3. the application of binary supermolecule nano particle of a pH response as claimed in claim 1, it is characterized in that: for load module molecule 8-hydroxyl pyrene-1, 3, 6-trisulfonic acid trisodium salt (HPTS) also realizes controllable release, carrying method is: by 8-hydroxyl pyrene-1, 3, 6-trisulfonic acid trisodium salt (HPTS) is added drop-wise in the binary supermolecule nano particle solution containing sulfated cyclodextrins (SCD) and chitosan (CS), 8-hydroxyl pyrene-1 in solution, 3, 6-trisulfonic acid trisodium salt, the concentration of sulfated cyclodextrins and protamine is respectively 0.01mM, 35mmol/mL and 0.01mg/mL, then be 3500 bag filter dialysis purification by solution molecular cut off.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105641709A (en) * | 2016-01-11 | 2016-06-08 | 重庆医科大学 | Honokiol sulfobutyl ether-beta-cyclodextrin chitosan nano-particles for eyes and preparation method thereof |
| CN106967419A (en) * | 2017-04-14 | 2017-07-21 | 南开大学 | A kind of ternary nano oversubscription sub-light good harvest system of sulfated cyclodextrins phenylenevinylene derivative Nile red and preparation method thereof |
| CN109908367A (en) * | 2019-04-30 | 2019-06-21 | 南开大学 | Application of the supramolecular nanoparticles that sulfanilic acid-beta-cyclodextrin mediates in terms of the control release of insulin |
| CN113384713A (en) * | 2021-06-12 | 2021-09-14 | 南开大学 | Enzyme-responsive supramolecular nanoparticle controllable-release anticancer drug adriamycin system and preparation method thereof |
| CN115093494A (en) * | 2022-06-17 | 2022-09-23 | 天津大学 | Light-controlled supermolecule micromotor and preparation method thereof |
| CN115368645A (en) * | 2022-08-23 | 2022-11-22 | 天津商业大学 | Nanoparticle assembly with pH responsiveness and preparation method thereof |
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| CN104288125A (en) * | 2014-09-21 | 2015-01-21 | 南开大学 | Binary supramolecular nano particles with enzyme response and preparation method and application thereof |
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| CN104288125A (en) * | 2014-09-21 | 2015-01-21 | 南开大学 | Binary supramolecular nano particles with enzyme response and preparation method and application thereof |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105641709A (en) * | 2016-01-11 | 2016-06-08 | 重庆医科大学 | Honokiol sulfobutyl ether-beta-cyclodextrin chitosan nano-particles for eyes and preparation method thereof |
| CN106967419A (en) * | 2017-04-14 | 2017-07-21 | 南开大学 | A kind of ternary nano oversubscription sub-light good harvest system of sulfated cyclodextrins phenylenevinylene derivative Nile red and preparation method thereof |
| CN109908367A (en) * | 2019-04-30 | 2019-06-21 | 南开大学 | Application of the supramolecular nanoparticles that sulfanilic acid-beta-cyclodextrin mediates in terms of the control release of insulin |
| CN113384713A (en) * | 2021-06-12 | 2021-09-14 | 南开大学 | Enzyme-responsive supramolecular nanoparticle controllable-release anticancer drug adriamycin system and preparation method thereof |
| CN115093494A (en) * | 2022-06-17 | 2022-09-23 | 天津大学 | Light-controlled supermolecule micromotor and preparation method thereof |
| CN115093494B (en) * | 2022-06-17 | 2023-01-31 | 天津大学 | Light-controlled supermolecule micromotor and preparation method thereof |
| CN115368645A (en) * | 2022-08-23 | 2022-11-22 | 天津商业大学 | Nanoparticle assembly with pH responsiveness and preparation method thereof |
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