CN104673753A - Composite nanoparticle for controlling H2S release by employing near-infrared light as well as preparation method and application of composite nanoparticle - Google Patents

Composite nanoparticle for controlling H2S release by employing near-infrared light as well as preparation method and application of composite nanoparticle Download PDF

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CN104673753A
CN104673753A CN201510051719.2A CN201510051719A CN104673753A CN 104673753 A CN104673753 A CN 104673753A CN 201510051719 A CN201510051719 A CN 201510051719A CN 104673753 A CN104673753 A CN 104673753A
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composite nanoparticle
infrared light
cell
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CN104673753B (en
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邓留
陈民
陈万松
刘又年
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Central South University
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Abstract

The invention discloses a composite nanoparticle for controlling H2S release by employing near-infrared light as well as a preparation method and an application of the composite nanoparticle. The composite nanoparticle is formed by loading organic H2S donor molecules on an up-conversion nanoparticle surface through a polyethylene glycol-oleylamine medium; and the preparation method is that the composite nanoparticle is obtained by chemical reaction of the up-conversion nanoparticle, the polyethylene glycol-oleylamine and the organic H2S donor molecules. The composite nanoparticle is good in stability; H2S can be released under near-infrared light illumination; the release rate can be regulated and controlled; the composite nanoparticle is good in cell compatibility, and small in cytotoxicity; the composite nanoparticle and the cell are cultured together, so that the donor cell, which can release the H2S under the near-infrared light illumination, and of which the release speed can be regulated and controlled can be obtained; and the composite nanoparticle is of great significance in the field of biological research.

Description

One near infrared light control H 2composite nanoparticle of S release and its preparation method and application
Technical field
The present invention relates to one and utilize near infrared light control H 2novel composite nano particle of S release and its preparation method and application, belongs to biochemical field.
Background technology
All the time, H 2s is considered to toxic gas.It not only has strong impulse effect to mammiferous eyes and respiratory system, sucks also may can cause the physiological responses such as clouding of consciousness, in heart failure if a large amount of.But research shows recently, H 2s and CO, NO are equally a kind of biogas molecules, have very important physiological significance.H 2s and oxygen carrier and nitrogenous substances have very high reactive behavior, such as hydrogen peroxide, superoxide, super-oxide, nitroso-group etc., are antioxidant important in organism and scavenging agent.The more important thing is, H 2s can be connected in the iron of protoheme in the heart with halfcystine generation mercaptolation.This process is to vasorelaxation, and neuroregulation, inflammation treatment has important regulating effect.
The H of institute in the past 2s donor, mainly inorganic sulphide, such as Na 2s, NaHS etc.Because these inorganic salt release H 2the speed of S is very fast, and the Co ntrolled release time is very difficult, is also difficult to H in mimic biology body 2the release of S, so the research needs that can not meet people.Organic H of the report such as Nelmi O.Devarie-Baez 2the release H that S supplies physical efficiency controlled continuously 2s gas, its concentration also with organism endogenous H 2s concentration quite (Nelmi O.Devarie-Baez et al., Org.Lett., 2013,15 (11), 2786 – 2789).But existing most of organic H 2s donor needs UV-irradiation to produce H 2s, UV-light is very large and tissue penetration is also strong, so hinder this kind of H to histiocytic injury 2the application in vivo of S donor.
Summary of the invention
For H in prior art 2the ultraviolet lighting that S donor exists needs energy stronger could discharge H 2s, and H 2the release rate of S is difficult to the defects such as control, makes it apply and is limited to, and the object of the invention is to be to provide a kind of good stability, can discharge H under near infrared light shines 2s, and the regulatable composite nanoparticle of rate of release.
Another object of the present invention is a kind of method being to provide simple to operate, described composite nano-granule of the gentle preparation of reaction conditions.
3rd object of the present invention is the application being to provide described composite nanoparticle, described composite nanoparticle and cell compatibility good, little to cytotoxic, be applied to cultivate near infrared light according under can discharge H 2s, and the regulatable donorcells of release rate, and at H 2in S dispose procedure, little to primary cellular defect.
The invention provides one near infrared light control H 2the composite nanoparticle of S release, this composite nanoparticle is by organic H 2s donor molecule (SP) is consisted of on up-conversion nanoparticles (UCNPs) surface the load of polyoxyethylene glycol-oleyl amine (mPEG-OM) medium; Described organic H 2s donor molecule has formula 1 structure:
Wherein,
R 1and R 2be selected from hydroxyl, amido, C independently of one another 1-4alkoxyl group, benzyloxy, phenyl ring has in the benzyloxy of abundant electron substituents group any one, R 3be selected from C 1-4alkyl.
Described abundant electron substituents group is C 1-4alkoxyl group, amino or amido.
Preferred organic H 2s donor molecule has the one in following structure:
wherein, R 4for C 1-4alkoxyl group, a kind of in amino or amido.
The present invention has organic H of formula 1 structure 2r in S donor molecule 1, R 2, R 3, R 4the different organic H obtained when selecting in above-mentioned scope respectively 2s donor molecule is stimulated and discharges H 2the wavelength of S is 320 ~ 370nm, at ultraviolet region.
Preferred composite nanoparticle can discharge H under near infrared light 2s.
Organic H of the present invention 2the preparation method of S donor molecule is as follows: compound a and alkyl or aluminum alkoxide are reacted under condition of ice bath, obtain intermediate b; Intermediate b and phosphorus tribromide carry out bromo-reaction, obtain intermediate c; At room temperature there is substitution reaction in intermediate c and thiocarbamide, obtains intermediate product d, and intermediate product and Sodium Pyrosulfite carry out deamination reaction, obtain intermediate e; Intermediate e and acetone are at TiCl 4react under catalysis, obtain target product f.
Organic H of the present invention 2the synthetic route of S donor molecule is as follows:
Present invention also offers the method for the composite nanoparticle described in preparation, the method is by UCNPs, mPEG-OM and organic H 2s donor molecule is dissolved in organic solvent, after supersound process, first at room temperature stirring reaction, thin up again, simultaneously raised temperature to 40 ~ 55 DEG C, continue stirring reaction, until after organic solvent volatilization completely, leave standstill, removing precipitation, obtains the emulsion containing composite nanoparticle (SP-PEG-UCNPs).
In preferred method, sonication treatment time is 20 ~ 40min.
In preferred method, at room temperature the time of stirring reaction is 0.5 ~ 1h.
MPEG-OM of the present invention prepares by the following method: be dissolved in by mPEG in deionized water, add the Sodium Bromide of 0.1 times amount and (tetramethyl piperidine) TEMPO of 0.1 times amount, stir under ice bath, then add the aqueous solution of a times amount containing 10% clorox; Dripping dilute hydrochloric acid makes the pH value of system remain on about 10; Stirring reaction is after 5 hours, and with dichloromethane extraction, underpressure distillation obtains white solid, i.e. Compound II per; Compound II per is dissolved in methylene dichloride, add the triethylamine of a times amount, I-hydroxybenzotriazole (HOBT) and HBTU (O-benzotriazole-tetramethyl-urea phosphofluoric acid ester), stirring reaction 1 hour under ice bath, then in the octadecylamine adding a times amount, i.e. compound III; Stirred at ambient temperature reacts 20 hours, sends out separation obtain white solid and compound IV with column chromatography.Concrete synthetic route:
Present invention also offers composite nanoparticle application, this application is applied to by described composite nanoparticle to cultivate can discharge H under near infrared light shines 2the donorcells of S.
At 37 ± 0.5 DEG C of temperature, cultivate cell 30 ~ 60min with the substratum containing described composite nanoparticle in preferred application method to obtain can discharging H under near infrared light shines 2the donorcells of S.
In preferred application method, cell is L929 cell, MCF-7 cell or Hela cell.
Preferred near infrared light is the near infrared light of wavelength within the scope of 800 ~ 1000nm.Most preferred infrared light is the near infrared light of wavelength within the scope of 800 ~ 850nm and 950 ~ 1000nm.
In preferred application method, intensity of illumination is for being not more than 20Wcm -2.
Hinge structure, beneficial effect of the present invention: the present invention designs novel can being stimulated under wavelength is the ultraviolet lighting of 320nm ~ 370nm of a class first and discharges H 2organic H of S 2s donor molecule; Be medium further by mPEG-OM on this basis, by this type of organic H 2s donor molecule loads to the obtained composite nanoparticle in up-conversion nanoparticles (UCNPs) surface, and this composite nanoparticle is by up-conversion nanoparticles and organic H 2produce FRET effect between S donor molecule, thus control H can be carried out by near infrared light (wavelength is 800 ~ 1000nm) 2the release of S, this nanoparticle not only can regulate and control the release H slowly continued 2s, and adopt near infrared light to get final product Co ntrolled release H 2s, near infrared light is little to cell tissue injury relative to UV-light, and penetration power is strong, can be applied to biological field well, obtains by near infrared light release H 2the biological donorcells of S gas.
Accompanying drawing explanation
[Fig. 1] discharges H near infrared light controls composite nanoparticle 2the schematic diagram of S.
[Fig. 2] is the organic H in composite nanoparticle 2s donor molecule 1h-NMR spectrogram.
[Fig. 3] is the organic H in composite nanoparticle 2s donor molecule 13c-NMR spectrogram.
[Fig. 4] is for mPEG-OM's 1h-NMR spectrogram.
[Fig. 5] is the UCNPs nanoparticle transmission electron microscope picture in composite nanoparticle.
The fluorescence spectrum stacking diagram that [Fig. 6] is PEG-UCNPs, SP-PEG-UCNPs and organic H 2the uv absorption spectra of S donor molecule.
[Fig. 7] a represents organic H 2the uv-absorbing typical curve of S molecule, b represents H 2the fluorescent emission typical curve of S probe.
[Fig. 8] a represents that different illumination intensity (is respectively 0Wcm -2, 6.5Wcm -2, 11Wcm -2, 16Wcm -2, 20Wcm -2) irradiate composite nanoparticle 1h after, add the H of same concentrations 2the fluorescence spectrum figure of S probe (200 μMs); B represents identical intensity of illumination (20Wcm -2) the different light time (being respectively 0h, 0.5h, 1h, 1.5h, 2h) irradiates composite nanoparticle, adds the H of same concentrations 2the fluorescence spectrum figure of S probe (200 μMs).
The graph of a relation that [Fig. 9] is SP-PEG-UCNPs concentration and cell survival rate.
[Figure 10] is with 16W cm -2intensity of illumination irradiates the L929 cell 1h cultivated containing composite nanoparticle nutrient solution, then cell is being added with H 2confocal fluorescent image after the nutrient solution cultivation 40min of S fluorescent probe; Wherein a is not for use 16W cm -2intensity of illumination irradiates the confocal fluorescent image of 1h, and c figure uses 16W cm -2intensity of illumination irradiates the confocal fluorescent image of 1h, and b, d figure is respectively a, the confocal fluorescent image of c figure in light field.
Embodiment
The following examples can make those skilled in the art more fully understand the present invention, but do not limit the present invention in any way.
Embodiment 1
Organic H 2the chemosynthesis of S donor molecule:
Synthetic route is as follows:
Its concrete steps are as follows:
(1) Weigh Compound I 3g (0.0142mol) is dissolved in 15mL anhydrous methylene chloride, and slowly dripping 7mL concentration under ice bath is 2molL -1trimethyl aluminium, solution colour becomes orange by xanthochromia, to be poured into by reaction solution with in the water-reducible hydrochloric acid of ice after reaction 2h.Filtration obtains thick product, utilizes column chromatography to carry out separation to thick product and obtains Compound II per.Productive rate is 50.7%.
(2) Weigh Compound II 1.63g is dissolved in 15mL methylene dichloride, and ice bath stirs.Measure 1.367mL phosphorus tribromide and slowly add above-mentioned solution.Transfer to room temperature after reacting 1.5h under ice bath and continue reaction 1.5h.After reaction terminates, dropped to by reaction solution in frozen water, separatory obtains organic solution, revolves steaming, and column chromatography is crossed post and obtained compound III.Productive rate is 80.2%.
(3) Weigh Compound III 1.67g is dissolved in tetrahydrofuran (THF), adds the thiocarbamide of 0.437g, and under room temperature, reaction is spent the night, and obtains thick product compound IV 0.6g.
(4) Weigh Compound IV 0.6g is dissolved in the mixed solvent of methylene dichloride and water, adds 1.38g Sodium Pyrosulfite, nitrogen protection stirred at ambient temperature reaction 4h.After reaction terminates, separatory obtains organic phase, revolves steaming and obtains thick yellow liquid, is compound V 0.11g.
(5) Weigh Compound V 0.11g is dissolved in chloroform, adds the acetone of 13.5 μ L, and ice bath slowly adds the titanium tetrachloride of 6 μ L under stirring.Reaction solution slowly rises to room temperature by-10 DEG C, and stirring is spent the night.Use column chromatography and obtain target compound SP.Yield 42%.Characterization result is shown in Fig. 2, Fig. 3. 1H NMR(500MHz,CDCl3)δ7.28(s,2H),7.03(s,2H),4.94(q,J＝7.2Hz,2H),3.99(s,6H),3.90(s,6H),1.62(d,J＝7.2Hz,6H),1.32(s,6H). 13C NMR(126MHz,CDCl3)δ153.31,147.47,140.52,136.48,111.45,106.99,58.11,56.47,56.37,39.03,31.25,31.11,24.30.
Embodiment 2
Up-conversion nanoparticles UCNPs (β-LiYF4:0.5%Er3 +, 25%Yb3 +) preparation:
Rare earth oxide (Y according to a certain ratio 2o 3: Yb 2o 3: Tm 2o 3=74.5%:25%:0.5%) be dissolved in appropriate trifluoroacetic acid, stirring reaction 5h at 80 DEG C, evaporates trifluoroacetic acid and obtains white powder solid.This mixed powder is dissolved in the mixing solutions of oleic acid and octadecylene, then adds the lithium fluoride of 8 times amount.110 DEG C are heated to, reaction 1h in vacuum environment.Under nitrogen protection, increase the temperature to 320 ~ 330 DEG C with 25 DEG C/min, strong stirring, after reaction 1h, be cooled to room temperature.Add appropriate acetone, to obtain white precipitate after the centrifugal 10min of 6000rpm.Be dissolved in chloroform after with acetone and washes of absolute alcohol twice.Removing unnecessary lithium fluoride with the centrifugal 1min of 2000rpm, finally obtaining product, being stored in chloroform for subsequent use.The transmission electron microscope of UCNPs characterizes sees Fig. 5.
MPEG-OM prepares by the following method:
Concrete synthetic route:
MPEG is dissolved in deionized water, adds the Sodium Bromide of 0.1 times amount and (tetramethyl piperidine) TEMPO of 0.1 times amount, stir under ice bath, then add the aqueous solution of a times amount containing 10% clorox; Dripping dilute hydrochloric acid makes the pH value of system remain on about 10; Stirring reaction is after 5 hours, and with dichloromethane extraction, underpressure distillation obtains white solid, i.e. Compound II per; Compound II per is dissolved in methylene dichloride, add the triethylamine of a times amount, I-hydroxybenzotriazole (HOBT) and HBTU (O-benzotriazole-tetramethyl-urea phosphofluoric acid ester), stirring reaction 1 hour under ice bath, then in the octadecylamine adding a times amount, i.e. compound III; Stirred at ambient temperature reacts 20 hours, sends out separation obtain white solid and compound IV (sign is shown in Fig. 4) with column chromatography.
SP molecule loads to UCNPs surface:
Take 50mg mPEG-OM, 30mg SP molecule, be dissolved in chloroform, then add 1mL UCNPs chloroformic solution (0.01M), after supersound process 30min, stirring at room temperature 0.5h, add 6mL deionized water subsequently, raised temperature to 45 DEG C, stirring reaction is until chloroform volatilizees completely, leave standstill removing precipitation, obtain transparent emulsion.
FRET effect between UCNPs and SP molecule is determined in fluorescent spectroscopy:
(1) the SP-PEG-UCNPs solution getting 3mL50 μM measures uv-absorbing intensity.Ultraviolet spectrogram is shown in Fig. 6.
(2) get PEG-UCNPs and the SP-PEG-UCNPs solution (50 μMs) of equivalent concentration, with 980nm near infrared light for excitation light source, measure its fluorescent emission intensity.
Fluorescence spectrum figure is shown in Fig. 6.
As seen from Figure 6, organic sulfide hydrogen donor mainly contains two absorption peaks at ultraviolet region, one at about 250nm, one at about 350nm, so the UV-light that it can absorb these two wave bands discharges hydrogen sulfide.And prepared up-conversion nanoparticles is under 980nm near infrared light, just also there is the emission peak that stronger at 350nm place, be just in time that absorption peak matches with organic sulfide hydrogen donor, thus hydrogen sulfide can be made to discharge.By the fluoroscopic image of SP-PEG-UCNPs compared with PEG-UCNPs image, can find out that the fluorescence of SP-PEG-UCNPs is except having obvious reduction in about 350nm intensity, and the fluorescence intensity of its all band does not have considerable change, this illustrates that up-conversion nanoparticles has part to be absorbed by organic sulfide hydrogen donor at the emission peak at 350nm place; Thus it can be made to discharge hydrogen sulfide.
Embodiment 3
The mensuration of UCNPs area load SP molecular amounts:
(1) drafting of ultraviolet typical curve: the SP molecular solution configuring different concns respectively: 10 μ gmL -1, 12.5 μ gmL -1, 16.5 μ gmL -1, 22.5 μ gmL -1, 28.5 μ gmL -1, 38.5 μ gmL -1, 50 μ gmL -1, measure ultraviolet light absorption intensity, draw ultraviolet typical curve and see Fig. 7 a.
(2) measuring 0.25mL SP-PEG-UCNPs solution, mix with 0.75mL acetonitrile solution, measure the ultraviolet light absorption intensity at 350nm place, is A 350nm=0.093.Bringing the concentration that ultraviolet standard curve fit function obtains this solution S P molecule into is 7.71 μ gmL -1.Namely 7.25 × 10 are had in 1mLSP-PEG-UCNPs solution 16individual SP molecule.
(3) getting the pure UCNPs of 1mL and dry weighing, is 20mg.The volume of a known UCNPs is 1.72 × 10 -16cm 3, UCNPs density is 4gcm -1, calculate in 1mL solution and have 2.91 × 10 13individual UCNPs.
(4) finally calculate load in a UCNPs and have 2500 SP molecules.
Embodiment 4
Intensity of illumination and H 2the linear relationship of S burst size:
Get in 1mLSP-PEG-UCNPs solution instillation cuvette, good seal is 0W cm by intensity respectively in dark surrounds -2, 6.5W cm -2, 11W cm -2, 16W cm -2, 20W cm -2near infrared light, irradiation time is 2h.Isocyatic H is added after irradiation terminates 2s fluorescent probe (100 μMs), respectively measures its fluorescence intensity after reacting 5min in dark surrounds.Its fluorescence intensity being brought in fluorescence standard curve fitting function (see Fig. 7 b), calculate its burst size (see Fig. 8 a).
The preparation of fluorescent probe: a kind of highly sensitive according to document (Hanjing Peng et at, Angew.Chem.Int.Ed., 2011,50,9672 – 9675) synthesis, the H that the reaction times is short 2s fluorescent probe, detects this Novel composite nano particle H by the method for fluorescent spectroscopy 2the burst size of S and release rate thereof.
Embodiment 5
Light application time and H 2the linear relationship of S burst size
Get in 1mLSP-PEG-UCNPs solution instillation cuvette, good seal is 20Wcm by intensity in dark surrounds -2near infrared light, the time is respectively 0h, 0.5h, 1h, 1.5h, 2h.Isocyatic H is added after illumination terminates 2s fluorescent probe (100 μMs), respectively measures its fluorescence intensity after reacting 5min in dark surrounds.Its fluorescence intensity is being brought in fluorescence standard curve fitting function (see Fig. 7 b), calculating its burst size (see Fig. 8 b).
In above-mentioned fluorescent spectroscopy, fluorescence parameter is arranged: excite and launch slit width and be 10nm, Photomultiplier tube voltage 250V, and excitation wavelength is 340nm.
Embodiment 6
Measure the cytotoxicity of SP-PEG-UCNPs:
(1) L929 cell and MCF-7 cell cultures are on cover glass, and the substratum of employing is RPMI substratum (containing 15% calf serum) and 1% Streptomycin sulphate and penicillin, and culture environment is in the incubator of 5% carbonic acid gas of 37 DEG C;
(2), before using, attached cell adopts does not rinse three times containing the RPMI substratum of serum, and in L929 cell and MCF-7 cell, add concentration is respectively 3 μMs, 6 μMs, 12 μMs, 25 μMs, 50 μMs, the SP-PEG-UCNPs solution of 100 μMs, incubates 40 minutes in 37 DEG C of temperature;
(3), after, normal saline flushing cell three times are adopted.Observation of cell under laser confocal microscope, calculates the survival rate (see Fig. 9) of cell.
Embodiment 7
Measure SP-PEG-UCNPs nanoparticle H in cell 2the releasing effect of S:
(1) L929 cell cultures is on cover glass, and the substratum of employing is RPMI substratum (containing 15% calf serum) and 1% Streptomycin sulphate and penicillin, and culture environment is in the incubator of 5% carbonic acid gas of 37 DEG C;
(2), before using, attached cell adopts normal saline flushing three times.Add the SP-PEG-UCNPs nano-particle solution that final concentration is 100M, incubate 40min in 37 DEG C of temperature;
(3), after, 20Wcm is used -2near infrared irradiating cell 1h, adding the H that concentration is 100 μMs 2s fluorescent probe, incubates 40min in 37 DEG C of temperature;
(4) last, attached cell adopts normal saline flushing three times.Observation of cell under laser confocal microscope, determines H by fluorescence distribution position and intensity 2the releasing effect (see Figure 10) of S.

Claims (9)

1. one kind with near infrared light control H 2the composite nanoparticle of S release, is characterized in that, by organic H 2s donor molecule is consisted of on up-conversion nanoparticles surface polyoxyethylene glycol-oleyl amine medium load; Described organic H 2s donor molecule has formula 1 structure:
Wherein,
R 1and R 2be selected from hydroxyl, amido, C independently of one another 1-4alkoxyl group, benzyloxy, phenyl ring has in the benzyloxy of abundant electron substituents group any one, R 3be selected from C 1-4alkyl.
2. composite nanoparticle according to claim 1, is characterized in that, described organic H 2s donor molecule has the one in following structure: wherein, R 4for C 1-4alkoxyl group, a kind of in amino or amido.
3. composite nanoparticle according to claim 1, is characterized in that, can discharge H under near infrared light 2s.
4. prepare the method for the composite nanoparticle described in any one of claims 1 to 3, it is characterized in that, by up-conversion nanoparticles, polyoxyethylene glycol-oleyl amine and organic H 2s donor molecule is dissolved in organic solvent, after supersound process, and first at room temperature stirring reaction, then thin up, raised temperature to 40 ~ 55 DEG C simultaneously, continue stirring reaction, until after organic solvent volatilization completely, leave standstill, removing precipitation, obtains the emulsion containing composite nanoparticle.
5. method according to claim 4, is characterized in that, sonication treatment time is 20 ~ 40min.
6. method according to claim 4, is characterized in that, at room temperature the time of stirring reaction is 0.5 ~ 1h.
7. the composite nanoparticle application described in any one of claims 1 to 3, is characterized in that, is applied to cultivate can discharge H under near infrared light shines 2the donorcells of S.
8. application according to claim 7, is characterized in that, cultivates cell 30 ~ 60min obtain can discharging H under near infrared light shines with the substratum containing described composite nanoparticle at 37 ± 0.5 DEG C of temperature 2the donorcells of S.
9. application according to claim 8, is characterized in that, described cell is L929 cell, MCF-7 cell or Hela cell.
CN201510051719.2A 2015-02-02 2015-02-02 It is a kind of to control H near infrared light2Composite nanoparticle of S releases and its preparation method and application Expired - Fee Related CN104673753B (en)

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