CN105147619A - Janus nanometer particle used for monitoring release of two kinds of medicine in real time and preparation method thereof - Google Patents
Janus nanometer particle used for monitoring release of two kinds of medicine in real time and preparation method thereof Download PDFInfo
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Abstract
The invention belongs to the technical field of biological medicine, and particularly relates to a Janus nanometer particle used for monitoring release of two kinds of medicine in real time and a preparation method thereof. A gold nanometer particle is arranged at one end of the Janus nanometer particle, and a silicon dioxide nanometer particle or a mesoporous silicon dioxide nanometer particle is arranged at the other end of the Janus nanometer particle, and the two kinds of medicine can be loaded at the two ends. The preparation method includes the three steps that the gold nanometer particle where one kind of medicine is loaded is prepared; a Janus nanometer particle connected with the gold nanometer particle and the silicon dioxide nanometer particle or the mesoporous silicone dioxide nanometer particle is prepared; a Janus nanometer particle where the other kind of medicine is loaded is prepared. Silicon dioxide and gold serving as constituting materials of the Janus nanometer particle have good biocompatibility, preparation is easy, and modification is convenient. The two kinds of medicine can be loaded at the same time, the proportion of the two kinds of medicine can be accurately controlled, the two kinds of medicine can be released based on different response theories, and the release process of the two kinds of medicine can be monitored in real time.
Description
Technical field
The invention belongs to biomedicine technical field, be specifically related to a kind of Janus nanoparticle for Real-Time Monitoring two kinds of drug releases and preparation method thereof.
Background technology
Multifunctional nano drug-loading system is subject to studying more and more widely and paying close attention to owing to can significantly improve the efficiency for the treatment of.The curative effect that loaded body is transported to the medicine of lesions position not only depends on its cumulative concentration at lesions position, simultaneously also by the impact of drug release process.Therefore, for a multi-functional drug-loading system, except the transport process of tracer drug, the dispose procedure developing suitable method monitoring medicine is also very important.The release environment of the normally in-vitro simulated medicine of traditional method to understand its dispose procedure, but in-vitro simulated environment and cell even internal milieu still there is larger difference.Patent CN104004149A discloses the release of a kind of amphipathic nature polyalcohol nanoparticle by a kind of medicine of FRET (fluorescence resonance energy transfer) (FRET) effect monitoring between coumarin that polymer pendant groups is modified and medicine.Patent CN103528996A discloses a kind of nanometer gold bar and causes the change at golden excellent surface plasmon absorption peak to monitor a kind of drug release process by drug release.But, clinically a lot for the treatment of means (such as chemotherapy of tumors etc.) normally two kinds of medicines use simultaneously.Vitro detection drug release has a lot of method, such as uv-visible absorption spectra, fluorescence spectrum, chromatograph, mass spectrum etc., but these methods can not or seldom be applicable to detect in cell or body, therefore need the method that development can be used in monitoring drug dispose procedure in cell and body badly, there is not been reported for these class methods.Relative to the transportation of carrier material, the dispose procedure of real-time detection of drugs is more difficult, because this has higher requirement to carrier material, namely has responsive intelligent response for drug release, and can produce the variable signal that can monitor; For the two or more drug release of Real-Time Monitoring, extremely difficult especially, namely based on above-mentioned to outside the requirement of carrier, also need can not produce mutual interference between detectable variable signal.In addition, if carrier loaded two kinds of medicines that use two kinds is different, then accurately can not control the drug ratios arriving lesions position; And if load two kinds of medicines on the same vector, then medicine drug loading is separately little on the one hand, cannot realize the different responses releases of two kinds of medicines on the other hand.Janus particle is that a class two sides has asymmetric particle of different nature, it can on particle of the same race integrated two kinds of relatively independent structures and different physicochemical properties, can load different pharmaceutical and being independent of each other respectively, be suitable for very much the release of monitoring two kinds of different pharmaceuticals in conjunction with two kinds of methods.The present invention has prepared a kind of nanoparticle with Janus structure, the two sides load different pharmaceutical respectively of particle, and can distinguish the release of these two kinds of medicines of Real-Time Monitoring.The Janus nanoparticle of this pair of medicine carrying and the real-time monitoring of release thereof are evaluate the process discharged based on the multiple response drug of nano-carrier to provide new means.
Summary of the invention
The object of the present invention is to provide a kind of Janus nanoparticle for Real-Time Monitoring two kinds of drug releases and preparation method thereof, to solve the real-time monitoring problem that other material cannot realize two kinds of response releases for two kinds of medicines.
Janus nanoparticle for Real-Time Monitoring two kinds of drug releases provided by the invention, its one end is golden nanometer particle, and the other end is solid silicon dioxide or mesoporous silicon oxide; The different medicine of load two kinds can be distinguished in two ends, and can carry out Real-Time Monitoring to the release of institute's carrying medicament.
In the present invention, described golden nanometer particle can be nano gold spherical, nanometer gold bar, nanometer Venus or nanometer gold shell.
In the present invention, the mode of described monitoring drug release can be fluorescence spectrum, Raman spectrum and nuclear magnetic resonance, NMR.
The preparation method of this Janus nanoparticle for Real-Time Monitoring two kinds of drug releases provided by the invention, comprises three steps:
(1) golden nanometer particle of a kind of medicine of load regulation is prepared
Such as, the solution stirring of solution of gold nanoparticles and the first medicine certain density is reacted 2-24 hour, the medicine (such as Ismipur, 6-thioguanine, topotecan hydrochloride, gemcitabine, acyclovir or fadrozole etc.) that can connect with golden nanometer particle key can use this method;
(2) the Janus nanoparticle of golden nanometer particle and Nano particles of silicon dioxide or the mesoporous silicon dioxide nano particle sub-connection prepared by step (1) is prepared;
This step can be divided into two kinds of methods, uses as the case may be:
First method is Pickering emulsion method, Nano particles of silicon dioxide or mesoporous silicon dioxide nano particle are scattered in the mixed solution of water and paraffin, be heated to more than 70 degrees Celsius (being generally 70 degrees Celsius-80 degrees Celsius), in homogenizer, be generally 15000rpm--20000rpm to be greater than 15000rpm() speed homogenizing, add hydrosulphonyl silane reagent reacting after cooling, then add the golden nanometer particle reaction 2-24 hour of the first medicine of the obtained load of step (1);
Second method is in-situ synthesized, load obtained for step (1) is dispersed in water after the golden nanometer particle centrifuge washing of the first medicine, join the alcoholic solution containing isopropyl alcohol, water, 4-mercaptobenzoic acid and polyacrylic acid aqueous solution successively, after stirring, then add ammonia and the aqueous isopropanol containing TEOS;
(3) the Janus nanoparticle of load the second medicine is prepared
Such as, the Janus nanoparticle in some way load the second medicine obtained by step (2), comprise directly and the second medicine stir load, or to the second medicine with corresponding chemical bond as ester bond, amido link, hydrazone key, imine linkage or disulfide bond etc. connect, with reach response release object.
The present invention has the following advantages: composition material silicon dioxide and the Jin Jun of Janus nanoparticle of the present invention have good biocompatibility, easily prepare, and is convenient to modify.Janus nano medicament carrying system of the present invention can the two kinds of medicines of load simultaneously, and accurately can control the ratio of two kinds of medicines, two kinds of medicines can discharge with different Response Mechanism, and also can the dispose procedure of these two kinds of medicines of Real-Time Monitoring.
Accompanying drawing explanation
Fig. 1 is the transmission electron microscope photo of Janus mesoporous silicon oxide/nano gold spherical.
Fig. 2 is the transmission electron microscope photo of Janus silicon dioxide/nano gold spherical.
Fig. 3 is the laser confocal microscope photo of amycin-coumarin-silicon dioxide/gold-6 purinethol Janus nanoparticle and HeLa co-culture of cells different time, blue-fluorescence ((a) coumarin) increases along with the time and strengthens, blue, green ((b) lysosome), red ((c) amycin) three kinds of fluorescence can overlapping ((d) merge), show that nanoparticle enters lysosome and medicine discharges wherein.
Fig. 4 is the details in a play not acted out on stage, but told through dialogues microphotograph of amycin-coumarin-silicon dioxide/gold-6 purinethol Janus drug-loading system and HeLa co-culture of cells different time, wherein, (a), (b), c () is respectively 0 minute, 15 minutes, the microphotograph of 30 minutes, d () is corresponding Raman spectrogram, the Raman signal of 6 purinethols weakens along with the increase of time and shows its dispose procedure.
Detailed description of the invention
Below in conjunction with drawings and the embodiments, the present invention is further detailed explanation.
Embodiment 1
(1) nano gold spherical of load Ismipur (6MP) is prepared
100mL25nm nano gold spherical solution is added 1mL0.1mg/mL6MP solution, reaction 6h;
(2) mesoporous silicon dioxide nano particle of preparation containing dyestuff coumarin derivative
Polysuccinimated umbelliferone-3-acetic acid and γ-aminopropylsilane reagent are reacted 12h with mol ratio 1.2:1 in dichloromethane; Then add equal-volume ethanol, obtain solution A.0.5g cetyl trimethyl ammonium bromide (CTAB) and 0.05gF127 add in 240mL water, be warmed up to 80 DEG C, add 1.75mL2mol/LNaOH, 2.5mL ethyl orthosilicate (TEOS) and 1mL solution A, reaction 2h, centrifugal, the 12h that refluxes in the hydrochloric acid-methanol solution of 4% removes CTAB, and centrifuge washing final vacuum is dry;
(3) Janus nanoparticle is prepared
Mesoporous silicon dioxide nano particle 100mg step (2) prepared is scattered in 10mL containing in 6.7% alcoholic solution of 1 μM of CTAB, is heated to 70 DEG C, adds 0.5g paraffin, with the speed homogenizing 20min of 15000rpm on homogenizer, stir 1h at 70 DEG C, cool to room temperature, add 10mL methanol and 100 μ L3-mercapto propyl group Ethoxysilanes reaction 1h, centrifugal, washing, is distributed in the nano gold spherical solution that 100mL prepared containing 3 μMs of steps (1), reaction 2h, centrifugal, washing, vacuum drying;
(4) the Janus nanoparticle of load doxorubicin hydrochloride (Dox) is prepared
52mg adipic dihydrazide is dissolved in 4mLDMSO, and add 500 μ L containing 74 μ L isocyanatopropyl triethoxysilane reaction 12h, 80 DEG C of distilling under reduced pressure, solid adds 2mL ethanol, obtains solution B.The Janus nanoparticle dispersion that 40mg step (3) obtains, in 16mL95% alcoholic solution, adds 60 μ L solution B, adjusts pH to 5, room temperature reaction 4h, adjusts pH to spend the night to neutral reaction, centrifugal, and washing with alcohol is dry, obtains solid C.35mg solid C is scattered in 10mL0.3mg/mLDox methanol solution, adds trifluoroacetic acid and adjusts pH to 5, room temperature reaction 48h, centrifugal, washing, vacuum drying.
Embodiment 2
(1) nano gold spherical of load 6-thioguanine (6TG) is prepared
1mL0.1mg/mL6TG solution is added, reaction 6h in 100mL40nm nano gold spherical solution;
(2) Nano particles of silicon dioxide of preparation containing dyestuff cy3
Polysuccinimated cy3 dyestuff and γ-aminopropylsilane reagent are reacted 12h with mol ratio 1.2:1 in dichloromethane, adds equal-volume ethanol and obtain solution A;
(3) Janus nanoparticle is prepared
By nano gold spherical obtained for 27mL step (1) with 2100g centrifugal force 20min, washing, be dispersed in 10mL water, dropwise to join containing 38mL isopropyl alcohol, 12mL water, 400 μ L containing the alcoholic solution of 5mM4-mercaptobenzoic acid, 400 μ L containing in the polyacrylic aqueous solution of 0.645mM, after stirring 30min, add 1.8mL ammonia and the 12mL aqueous isopropanol containing 8.96mMTEOS and 2mL solution A, stir 12h;
(4) the Janus nanoparticle of load curcumin (Cur) is prepared
2mg adipic dihydrazide is dissolved in 4mLDMSO, and add 500 μ L containing 74 μ L isocyanatopropyl triethoxysilane reaction 12h, 80 DEG C of distilling under reduced pressure, solid adds 2mL ethanol, obtains solution B.The Janus nanoparticle dispersion that 40mg step (3) obtains, in 16mL95% alcoholic solution, adds 60 μ L solution B, adjusts pH to 5, room temperature reaction 4h, adjusts pH to spend the night to neutral reaction, centrifugal, and washing with alcohol is dry, obtains solid C.35mg solid C is scattered in 20mL0.3mg/mLCur methanol solution, adds trifluoroacetic acid and adjusts pH to 5, room temperature reaction 48h, centrifugal, washing, vacuum drying.
Embodiment 3
(1) the nanometer gold shell of load topotecan hydrochloride (TPT) is prepared
10mL nanometer gold shell solution is added 1mL10mg/mLTPT aqueous solution, stirs 6h, centrifugal;
(2) mesoporous silicon dioxide nano particle of gadolinium-doped is prepared
0.5g cetyl trimethyl ammonium bromide (CTAB) and 0.05gF127 are added in 240mL water, be warmed up to 80 DEG C, add 1.75mL2mol/LNaOH, 2.5mLTEOS and 0.5mL aminopropyl triethoxysilane (APTES) solution, reaction 2h, centrifugal, the 12h that refluxes in the hydrochloric acid-methanol solution of 4% removes CTAB, and centrifuge washing final vacuum is dry.The amidized mesoporous silicon oxide particle dispersion of 50mg, in 15mLDMF, adds the triethylamine solution of 150 μ L containing 10 μm of olDOTA-NHSester, stirs 24h, washing with alcohol.Again be dispersed in ethanol, add 20 μm of olGdCl
3reaction 24h, washing with alcohol, dry;
(3) Janus nanoparticle is prepared
Mesoporous silicon dioxide nano particle obtained for 200mg step (2) is scattered in 10mL containing in 6.7% alcoholic solution of 1 μM of CTAB, is heated to 80 DEG C, adds 1g paraffin, with the speed homogenizing 10min of 25000rpm on homogenizer, stir 1h at 80 DEG C, cool to room temperature, add 10mL methanol and 200 μ L3-mercapto propyl group Ethoxysilanes reaction 4h, centrifugal, washing, is distributed in the nanometer gold shell solution that 400mL obtains containing the step (1) of 3 μMs, reaction 24h, centrifugal, washing, vacuum drying;
(4) the Janus nanoparticle of load Dox is prepared
52mg adipic dihydrazide is dissolved in 4mLDMSO, and add 500 μ L containing 74 μ L isocyanatopropyl triethoxysilane reaction 12h, 80 DEG C of distilling under reduced pressure, solid adds 2mL ethanol, obtains solution B.The Janus nanoparticle dispersion that 40mg step (3) obtains, in 16mL95% alcoholic solution, adds 60 μ L solution B, adjusts pH to 5, room temperature reaction 4h, adjusts pH to spend the night to neutral reaction, centrifugal, and washing with alcohol is dry, obtains solid C.35mg solid C is scattered in 15mL0.3mg/mLDox methanol solution, adds trifluoroacetic acid and adjusts pH to 5, room temperature reaction 48h, centrifugal, washing, vacuum drying.
Embodiment 4
(1) nanometer gold bar of load gemcitabine is prepared
10mL nanometer gold bar solution is added 1mL0.1mg/mL Jixitabin solution, reaction 12h, centrifugal;
(2) mesoporous silicon dioxide nano particle of preparation containing dyestuff coumarin derivative;
Polysuccinimated umbelliferone-3-acetic acid and γ-aminopropylsilane reagent are reacted 12h with mol ratio 1.2:1 in dichloromethane, adds equal-volume ethanol and obtain solution A.0.5g cetyl trimethyl ammonium bromide (CTAB) and 0.05gF127 add in 240mL water, be warmed up to 80 DEG C, add 1.75mL2mol/LNaOH, 2.5mL ethyl orthosilicate (TEOS) and 1mL solution A, reaction 2h, centrifugal, the 12h that refluxes in the hydrochloric acid-methanol solution of 4% removes CTAB, and centrifuge washing final vacuum is dry;
(3) Janus nanoparticle is prepared
Mesoporous silicon dioxide nano particle 100mg step (2) obtained is scattered in 10mL containing in 6.7% alcoholic solution of 1 μM of CTAB, is heated to 75 DEG C, adds 0.5g paraffin, with the speed homogenizing 15min of 20000rpm on homogenizer, stir 1h at 75 DEG C, cool to room temperature, add 10mL methanol and 100 μ L3-mercapto propyl group Ethoxysilanes reaction 1h, centrifugal, washing, is distributed in the nanometer gold bar solution that 100mL obtains containing 3 μMs of steps (1), reaction 10h, centrifugal, washing, vacuum drying;
(4) the Janus nanoparticle of load melphalan is prepared
The Janus nanoparticle dispersion that 100mg step (3) obtains, in 10mL alcoholic solution, adds 1mL10mg/mL melphalan alcoholic solution, stirs 24h, centrifugal, washing.
Embodiment 5
(1) polysuccinimated cy5 dyestuff and γ-aminopropylsilane reagent are reacted 12h with mol ratio 1.2:1 in dichloromethane, add equal-volume ethanol and obtain solution A;
(2) Janus nanoparticle is prepared
By 27mL40nm nano gold spherical with 2100g centrifugal force 20min, washing, be dispersed in 10mL water, dropwise to be added drop-wise to containing 38mL isopropyl alcohol, 12mL water, 400 μ L containing the alcoholic solution of 5mM4-mercaptobenzoic acid, 400 μ L containing in the polyacrylic aqueous solution of 0.645mM, after stirring 30min, add 1.8mL ammonia and the 12mL aqueous isopropanol containing 8.96mMTEOS and 2mL solution A, stir 12h.With 2100g centrifugal force 30min, washing twice, is distributed in 10mL water, add chlorauric acid solution, the 10 μ L1M hydrochloric acid of 19.8 μ L containing 0.1265M successively, 100 μ L3mM silver nitrate, 50 μ L0.1M ascorbic acid, with 1100g centrifugal force 5min after rapid stirring 60s, washing.Add 1mL0.1mg/mL fadrozole solution, reaction 6h, centrifugal;
(3) the Janus nanoparticle of load Dox is prepared
52mg adipic dihydrazide is dissolved in 4mLDMSO, and add 500 μ L containing 74 μ L isocyanatopropyl triethoxysilane reaction 12h, 80 DEG C of distilling under reduced pressure, solid adds 2mL ethanol, obtains solution B.By Janus nanoparticle dispersion obtained for 40mg step (2) in 16mL95% alcoholic solution, add 60 μ L solution B, adjust pH to 5, room temperature reaction 4h, adjust pH to spend the night to neutral reaction, centrifugal, washing with alcohol, dry, obtain solid C.35mg solid C is scattered in 20mL0.3mg/mLDox methanol solution, adds trifluoroacetic acid and adjusts pH to 5, room temperature reaction 48h, centrifugal, washing, vacuum drying.
Embodiment 6
In the Janus nano medicament carrying system prepared by laser confocal microscope monitoring embodiment 1, Dox is in the intracellular release of HeLa.HeLa cell cultivates 24h in DMEM culture medium, sucking-off culture medium, add Janus nanoparticle co-cultivation prepared in the 250 μ g/mL embodiments 3 with culture medium preparation, at different time by the culture medium sucking-off containing material, three times are cleaned with PBS, dye to Cytolysosome with LysoTrackergreenDND-26, observe under being placed in laser confocal microscope.Blue-fluorescence (coumarin) in time gradually strengthen show that Dox releases gradually from carrier.6MP is monitored in embodiment 1 in the Janus nano medicament carrying system of preparation in the intracellular release of HeLa with laser Raman spectroscopy (joining dark field microscope).HeLa cell cultivates 24h in DMEM culture medium, sucking-off culture medium, add Janus nanoparticle co-cultivation 12h prepared in the 250 μ g/mL embodiments 1 with culture medium preparation, by culture medium sucking-off, clean three times with PBS, after adding 5mM glutathione monoethyl ester, different time is tested under being placed in laser Raman spectrometer (joining dark field microscope).Raman signal weakens gradually in time and shows that 6MP releases gradually from carrier.
Embodiment 7
With NMR (Nuclear Magnetic Resonance)-imaging (MRI) monitor embodiment 3 prepare Janus nano medicament carrying system in Dox in the intracellular release of HeLa.HeLa cell cultivates 24h in DMEM culture medium, sucking-off culture medium, adds Janus nanoparticle co-cultivation prepared in the 250 μ g/mL embodiments 3 with culture medium preparation, at different time by the culture medium sucking-off containing material, clean three times with PBS, observe under being placed in MRI.Along with the time increases gradually, longitudinal relaxation shows that Dox releases gradually from carrier.TPT is monitored in embodiment 3 in the Janus nano medicament carrying system of preparation in the intracellular release of HeLa with laser Raman spectroscopy (joining dark field microscope).HeLa cell cultivates 24h in DMEM culture medium, sucking-off culture medium, add Janus nanoparticle co-cultivation 12h prepared in the 250 μ g/mL embodiments 3 with culture medium preparation, by culture medium sucking-off, clean three times with PBS, after adding 5mM glutathione monoethyl ester, different time is tested under being placed in laser Raman spectrometer (joining dark field microscope).Raman signal weakens gradually in time and shows that TPT releases gradually from carrier.
Claims (7)
1. for a Janus nanoparticle for Real-Time Monitoring two kinds of drug releases, it is characterized in that: its one end is golden nanometer particle, the other end is Nano particles of silicon dioxide or mesoporous silicon dioxide nano particle; Two ends can the different medicine of load two kinds, and carries out Real-Time Monitoring to the release of institute's carrying medicament.
2. according to described in claim 1 for the Janus nanoparticle of Real-Time Monitoring two kinds of drug releases, it is characterized in that: described golden nanometer particle is nano gold spherical, nanometer gold bar, nanometer Venus or nanometer gold shell.
3. according to described in claim 1 for the Janus nanoparticle of Real-Time Monitoring two kinds of drug releases, it is characterized in that: the mode of described monitoring drug release is fluorescence spectrum, Raman spectrum or nuclear magnetic resonance, NMR.
4., as claimed in claim 1 for a preparation method for the Janus nanoparticle of Real-Time Monitoring two kinds of drug releases, it is characterized in that concrete steps are:
(1) golden nanometer particle of a kind of medicine of load regulation is prepared;
(2) the Janus nanoparticle of golden nanometer particle and Nano particles of silicon dioxide or the mesoporous silicon dioxide nano particle sub-connection prepared by step (1) is prepared;
(3) the Janus nanoparticle of load the second medicine is prepared.
5. preparation method according to claim 4, is characterized in that, the operating process of step (1) is: the solution stirring of solution of gold nanoparticles and the first medicine is reacted 2-24 hour.
6. preparation method according to claim 4, is characterized in that, the operation of step (2) is divided into two kinds:
First method is Pickering emulsion method, Nano particles of silicon dioxide or mesoporous silicon dioxide nano particle are scattered in the mixed solution of water and paraffin, be heated to more than 70 degrees Celsius, to be greater than the speed homogenizing of 15000rpm in homogenizer, add hydrosulphonyl silane reagent reacting after cooling, then add the golden nanometer particle reaction 2-24 hour of the first medicine of the obtained load of step (1);
Second method is in-situ synthesized, load obtained for step (1) is dispersed in water after the golden nanometer particle centrifuge washing of the first medicine, join the alcoholic solution containing isopropyl alcohol, water, 4-mercaptobenzoic acid and polyacrylic acid aqueous solution successively, after stirring, then add ammonia and the aqueous isopropanol containing TEOS.
7. preparation method according to claim 4, it is characterized in that, the operating process of step (3) is: direct for Janus nanoparticle obtained for step (2) and the second medicine are stirred load, or comprise ester bond, amido link, hydrazone key, imine linkage or disulfide bond to the second medicine with corresponding chemical bond to connect, to reach the object of response release.
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