CN109846857A - A kind of preparation method and applications of the natural supermolecule photosensitizer of activity - Google Patents

A kind of preparation method and applications of the natural supermolecule photosensitizer of activity Download PDF

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CN109846857A
CN109846857A CN201910300795.0A CN201910300795A CN109846857A CN 109846857 A CN109846857 A CN 109846857A CN 201910300795 A CN201910300795 A CN 201910300795A CN 109846857 A CN109846857 A CN 109846857A
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photosensitizer
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CN109846857B (en
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杨鑫
程建军
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Harbin Institute of Technology
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Abstract

It is described using sterols carrier nanoparticle as carrier the invention discloses a kind of preparation method and applications of the natural supermolecule photosensitizer of activity, using dihydro porphin photosensitizer Ce6 as medicine preparation activity supermolecule photosensitizer.Natural products with anticancer activity is delivered photosensitizer as nano-carrier by the present invention, on the one hand nano combined photosensitive dose of preparation has water solubility, the stability of enhancing, increased active oxygen yield significantly improved, and improved cell phagocytic activity, it is ensured that efficient external and anti-cancer activity in vivo;On the other hand, sterols product with anticancer activity itself has apparent Synergistic anti-cancer effect in conjunction with individual photosensitizer, sterol substance has excellent biocompatibility and the degradable ability of biology simultaneously, finally ensures efficient and safe antineoplaston.

Description

A kind of preparation method and applications of the natural supermolecule photosensitizer of activity
Technical field
The invention belongs to biological medicine field of material technology, are related to a kind of preparation method of natural supermolecule photosensitizer of activity And its application.
Background technique
Cancer is that current serious threatens one of human health and the important diseases of life security, is sought novel, effective, safe Anticancer drug be always researcher concern hot spot.Currently, in numerous anticancer means, optical dynamic therapy is as one Kind invasive is small, toxic side effect is low, safe and efficient novel tumor therapeutic modality, is reported and approves extensively.Wherein, light is dynamic The core of power treatment is photosensitizer, and what is be currently studied extensively is the dihydro porphin photosensitizer of hypotoxicity, but this kind of photosensitive Agent generally has the shortcomings that easily aggregation, cancer target are selectively low under low bioavilability, poorly water-soluble, physiological condition, limitation Its clinical practice application.Thus, for the water solubility for improving photosensitizer, its tumor-targeting, enhancing anticancer therapeutic are improved, exploitation is closed Suitable carrier is significant to transport.
Supramolecular chemistry (intermolecular chemical reaction) typically refers between two or more substances by intermolecular non- The substance that covalent effect power is combined into.It is based on this weak force, supermolecule photosensitizer is presented in optical dynamic therapy Huge advantage out, wherein most self assemblies or the novel photosensitive agent assembled altogether all show significant anticancer therapeutic.Based on this There is excellent biocompatibility and the substance of the degradable ability of biology, certain anticancer activity to carry out carrier construction fortune for strategy, many Defeated photosensitizer overcomes the defect of traditional photosensitizer for photodynamic therapy.It is important that these carriers can not be provided simultaneously with this A little advantageous properties, and the additional molecule with self-assembly ability is needed to construct supermolecule photosensitizer, and preparation process is opposite It is cumbersome.Thus, exploitation be provided simultaneously with the carrier of above-mentioned advantageous property very it is necessary to.Natural products derives from organism, has Good biocompatibility and the degradable ability of biology.Wherein, sterol substance has excellent physiological activity (such as anticancer), by it Photosensitizer defect on the one hand can be solved as vector construction supramolecular system transport photosensitizer, on the other hand the nanometer system of building It is expected to mention based on high-permeability and retention effect (enhanced permeability and retention effect, EPR) High drug tumor-targeting, furthermore the substance of these anticancer activities is expected to play collaboration enhancing anticancer therapeutic purpose, really realizes Safe and efficient tumour physical therapy.
Summary of the invention
In order to solve traditional dihydro porphin photosensitizer (such as: chlorin e 6, abbreviation Ce6) poorly water-soluble, stability it is low, Physiological condition, which is easily assembled, leads to that bioavilability is low, tumor-targeting poor the disadvantages of causing anticancer activity relatively low, and the present invention provides A kind of preparation method and applications of the natural supermolecule photosensitizer of activity.The present invention is natural with the sterols with anticancer activity Product does carrier to transport photosensitizer, plays the water-soluble independent photosensitizer of enhancing and cancer target ability of aggregation and Synergistic anti-cancer The purpose of curative effect.
The purpose of the present invention is what is be achieved through the following technical solutions:
A kind of preparation method of the natural supermolecule photosensitizer of activity, using sterols carrier nanoparticle as carrier, with chlorin Class photosensitizer Ce6 is medicine preparation activity supermolecule photosensitizer, the specific steps are as follows:
(1) Ce6 dimethyl sulphoxide solution (≤15 mg/mL) and sterols are dissolved into (carbon tetrachloride, dichloro in organic solvent Methane, chloroform or acetone), it is then added dropwise to the emulsification of 2.5% (mass/volume ratio) polyvinyl alcohol water solution mesoscale eddies dropwise 0.25 ~ 2 min controls mass ratio≤15% of Ce6 and sterols, the quality of sterols and volume ratio≤10 of organic solvent, has Solvent and the volume ratio of 2.5% polyvinyl alcohol water solution are 1:1 ~ 5;
(2) 20 ~ 90s is emulsified using ultrasonic cell disintegration instrument under condition of ice bath;
(3) step (2) obtained lotion is added rapidly to 0.3%(mass/volume ratio) in polyvinyl alcohol water solution, room temperature It is protected from light magnetic agitation volatilization organic reagent, the volume ratio for controlling organic solvent and 0.3% polyvinyl alcohol water solution is 1:20 ~ 50, magnetic Power mixing speed is 350 ~ 600 rpm;
(4) centrifugation obtains active supermolecule photosensitizer, and is lyophilized and saves after being washed repeatedly with secondary distilled water.
The active supermolecule photosensitizer that the above method is prepared can be used for antineoplaston.
Compared with the prior art, the present invention has the advantage that
The key constraints of traditional optical dynamic therapy first is that photosensitizer poorly water-soluble, easily aggregation, both dropped in physiological conditions The yield of low activity oxygen, while photosensitizer drug is largely reduced in the aggregation of tumor sites, limit its clinical use.Cause And in order to overcome this disadvantage, the natural products with anticancer activity is delivered photosensitizer as nano-carrier by the present invention, and one Nano combined photosensitive dose of aspect preparation has water solubility, the stability of enhancing, increased active oxygen yield significantly improved, with And improved cell phagocytic activity, it is ensured that efficient external and anti-cancer activity in vivo;On the other hand, itself has anticancer activity Sterols product has apparent Synergistic anti-cancer effect in conjunction with individual photosensitizer, while sterol substance has excellent life Object compatibility and the degradable ability of biology, finally ensure efficient and safe antineoplaston (external mouse tumor control rate For 86.4%).
Detailed description of the invention
Fig. 1 is scanning electron microscope (SEM) picture of three kinds of nanometer medicine-carried systems, A: cupreol (Stio NPs), B: ergot Sterol (Ergo NPs), C: stigmasterol (Stigma NPs);
Fig. 2 is anticancer toxicity of three kinds of independent carriers to 4T1 cell of various concentration;
Fig. 3 is anticancer toxicity of three kinds of independent carriers to MCF-7 cell of various concentration;
Fig. 4 is tri- kinds of nanometric photosensitizers pair of Ergo-Ce6 NPs, Stigma-Ce6 NPs, Stio-Ce6 NPs of various concentration 4T1 cells in vitro phototoxicity result;
Fig. 5 is tri- kinds of nanometric photosensitizers pair of Ergo-Ce6 NPs, Stigma-Ce6 NPs, Stio-Ce6 NPs of various concentration MCF-7 cells in vitro phototoxicity result;
Fig. 6 is the ultraviolet-visible of independent carrier Ergo NPs, Ce6, Ergo-Ce6 NPs and Ergo NPs/Ce6 mixture Abosrption spectrogram;
Fig. 7 is relative tumour volume of the mouse after Ergo NPs, Ce6, Ergo-Ce6 NPs are treated three times under illumination condition Variation diagram;
Volume change figure during Fig. 8 is mouse treatment of cancer.
Specific embodiment
Further description of the technical solution of the present invention with reference to the accompanying drawing, and however, it is not limited to this, all to this Inventive technique scheme is modified or replaced equivalently, and without departing from the spirit and scope of the technical solution of the present invention, should all be covered Within the protection scope of the present invention.
The present invention provides a kind of preparation methods of the natural supermolecule photosensitizer of activity, and described method includes following steps:
(1) preparation of sterols natural products carrier nanoparticle (NPs)
It mainly include three kinds of sterols carriers: ergosterol (Ergosterol, Ergo NPs), stigmasterol (Stigmasterol, Stigma NPs), cupreol (β-Stiosterol, Stio NPs), structural formula is as follows:
The present invention prepares carrier nanoparticle using emulsion-solvent evaporation method, the specific steps are as follows: by 5 mg sterols (ergots Sterol, stigmasterol, cupreol) (carbon tetrachloride or methylene chloride) is dissolved in the organic solvent of 1 mL, then it is added dropwise dropwise Into 4 ml, 2.5% (mass/volume ratio) polyvinyl alcohol water solution, be then vortexed 1 min of emulsification, and further in ice bath Under the conditions of 60s(frequency emulsified using ultrasonic cell disintegration instrument: 5s ultrasound, 5s rests, ultrasound intensity: 40%).It will be obtained Lotion be added rapidly to 40 ml, 0.3% polyvinyl alcohol water solution in, under 400 rpm magnetic agitations, room temperature is protected from light stirring Volatilize organic reagent 12h.Then, centrifugation obtains nanoparticle (NPs) at 12000 rpm, and is washed repeatedly with secondary distilled water It is lyophilized and saves after washing 3 times.
Fig. 1 is the nano material SEM picture of three kinds of sterol substances preparation.Using emulsion-solvent evaporation method, three kinds of sterols Substance can form the uniform nanoparticle of pattern, and have excellent dispersibility.Wherein, cupreol and ergosterol are formed Be baseball shape nanoparticle, average particle diameter size is respectively 273(l) × 113(w) and 154(l) × 95(w) nm.And beans steroid Alcohol be capable of forming average grain diameter be 585(l) × 114(w) and nm rod-shaped nanoparticle.This three kinds of sterol of explanation could act as A kind of nano material transport photosensitizer or other drugs molecule.
(2) preparation of active supermolecule photosensitizer
It is super using dihydro porphin photosensitizer Ce6 as three kinds of medicine preparation respectively using above-mentioned three kinds of natural sterols substances as carrier Molecular photoactive agent, respectively Ergo-Ce6 NPs, Stigma-Ce6 NPs, Stio-Ce6 NPs.
By the Ce6 dimethyl sulphoxide solution (≤15 mg/mL) of 50 μ L and sterols carrier (ergosterol, beans of 5 mg Sterol, cupreol) (carbon tetrachloride or methylene chloride) is dissolved in the organic solvent of 1 mL, it is then added dropwise to 4 ml dropwise 2.5% (mass/volume ratio) polyvinyl alcohol water solution in.Carrier (Ergo NPs, Stigma are prepared by exactly the same NPs, Stio NPs) condition obtain three kinds of load medicine supermolecule photosensitizers.
Three kinds of supermolecule photosensitizers are dissolved by solvent of dimethyl sulfoxide, medicine is carried using high performance liquid chromatography detection Ce6 Amount.Actual conditions are as follows: mobile phase: 30 DEG C of column temperature, mobile phase: 0.2% phosphate aqueous solution/acetonitrile=40/60(volume ratio) and, stream Speed: 1mL/min, Detection wavelength: 402 nm.It is final to determine that drugloading rate is respectively as follows: Ergo-Ce6 NPs(3.4%), Stigma- Ce6 NPs (2.4%), Stio-Ce6 NPs(4.3%).
Fig. 2 is the cell survival rate curve after 4T1 cell and three kinds of carriers are cultivated respectively.The result shows that three kinds of nanoparticles Concentration dependent anticancer activity is presented in son, and with the increase of drug concentration, cell survival rate is gradually decreased.Wherein, Ergo The cytotoxicity of NPs and Sito NPs is apparently higher than Stigma NPs.Under the concentration of 25 μ g/mL, Ergo NPs and Sito The tumor control rate of NPs is respectively 48% and 39%, this shows that three kinds of nano-carriers all have anticancer activity, is expected to realization and drug The purpose of synergistic treatment.
Fig. 3 is the cell survival rate curve after MCF-7 cell and three kinds of carriers are cultivated respectively.As a result it is also demonstrated that, three kinds Carrier equally has certain cytotoxicity to the MCF-7 breast cancer cell of source of people, under the concentration of 25 μ g/mL, Ergo NPs Tumor control rate with Sito NPs is respectively 45% and 48 %, is equally higher than Stigma NPs (37%).
Fig. 2 and Fig. 3's the result shows that natural products sterol substance have certain anticancer activity, be expected to realize carry medicine after Synergistic anti-cancer, the purpose to heighten the effect of a treatment.
(3) three kinds of active supermolecule photosensitizers (Ergo-Ce6 NPs, Stigma-Ce6 NPs, Stio-Ce6 NPs) are external Anticancer activity assessment
Respectively using source of mouse 4T1 and source of people MCF-7 breast cancer cell as cell strain, using the mtt assay detection drug of standard in illumination Under the conditions of anticancer activity.Detailed process is as follows: use 96 orifice plate inoculated tumour cells, to it is adherent for 24 hours, various concentration is added The Ce6 drug of equivalent continues after cultivating 4 h, then 10 min of lighting process under the infrared light of 675 ± 10 nm, then Mtt assay detects cell survival rate.
Fig. 4 is 4T1 cell and three kinds of complex photosensitizer drugs are cultivated and the cell survival rate after lighting process.Result in figure Clearly showing under the drug Ce6 concentration of equivalent, the cell inhibitory rate dramatically increased is presented after carrying medicine in three kinds of carriers, Anticancer effect is obvious.Wherein, when Ce6 concentration is 1 μ g/mL, the tumour cell of Ergo-Ce6 NPs and Sito-Ce6 NPs press down Rate processed is respectively 70% and 68%, and the inhibition rate of tumor cell of Stigma-Ce6 NPs is 82%, hence it is evident that it is thin to be higher than individual Ce6( 42%) born of the same parents' inhibiting rate is.This illustrates the light poison for all significantly increasing drug alone to tumour cell after three kinds of carrier delivery photosensitizers Property, there is significant anticancer therapeutic.
Fig. 5 is respectively that MCF-7 is cell survival rate after three kinds of complex photosensitizers are incubated under 10 min of illumination, San Zhejun Concentration dependent cell inhibitory rate is showed, with the increase of complex photosensitizer drug concentration, cell survival rate is gradually decreased.Especially It is, when the Ce6 concentration of equivalent is 0.5 μ g/mL, to show compared to free Ce6 drug (12% inhibiting rate) three The cell inhibitory rate of the anticancer activity dramatically increased out, Ergo-Ce6 NPs, Stigma-Ce6 NPs and Stio-Ce6 NPs point It Wei 94%, 94%, 72%.
The result of Fig. 4 and Fig. 5 absolutely proves, shows the cell significantly increased after three kinds of carrier cladding photosensitizer Ce6 Activity, and this anticancer activity is from two aspects: 1) carrier itself active, and collaboration increases drug anticancer therapeutic; 2) after loading photosensitizer, the water solubility of photosensitizer is increased using nanoparticle prepared by emulsion process, is reduced caused by autohemagglutination Low phototoxicity.As a result sufficiently show: three kinds of natural activity carriers are applicable to construct supermolecule photosensitizer as pharmaceutical carrier.
(4) using Ergo-Ce6 NPs as example, internal anticancer effect is investigated.
Using the Balb-c female small white mouse for being inoculated with 4T1 tumour cell as lotus knurl research object, it is administered using tail vein injection Mode, study drug anticancer therapeutic.Specific experiment is divided into two groups, every group of 5 mouse: 1- blank control group: only 5% Portugal of injection Grape sugar aqueous solution;The independent vehicle group Ergo NPs of 2-;3- administration group Ergo-Ce6 NPs: pass through tail vein injection Ergo-Ce6 The Ce6 4mg/kg of NPs(equivalent) after 6h, anesthesia is implemented to mouse and by lighting process 15min under tumour infrared light.Respectively Corresponding treatment 14 days is implemented to mouse the 0th day, 3 days, 6 days, during which records a mouse gross tumor volume and body every three days The parameters such as again.Mouse gross tumor volume calculation formula: V=(L × W2)/2。
Fig. 6 is the UV absorption of Ergo NPs, Ce6, Ergo-Ce6 NPs and mixture E rgo NPs/Ce6.Individually Carrier Ergo NPs only in ultraviolet region, there are four characteristic absorption peak (264,274,285,297 nm), and drug Ce6 has The apparent peak Soret and the peak Qy, respectively 406 nm and 668nm.It is purple after constructing supermolecule photosensitizer Ergo-Ce6 NPs The corresponding characteristic peak of carrier Ergo NPs and Ce6 is presented in outer absorption spectrum, and maximum absorption wavelength (peak Qy) occurs obviously Red shift illustrates that π-π interaction has occurred in carrier ergosterol molecule and photosensitizer Ce6, promotes Red Shift Phenomena to 672 nm Occur.In addition, the ultraviolet absorpting spectrum of Ergo-Ce6 NPs is distinct from both independent mixture (Ergo NPs/Ce6), and The variation what can be distinguished does not occur at the peak maximum absorption wavelength Qy of Ce6 in the mixture.The above result shows that Ce6 is successfully cladded in the nanoparticle that carrier ergosterol is formed.
Fig. 7 is mouse in the tumor Volume Changes figure after relative medicine is treated.Individual drug Ce6 and Ergo NPs Treated under illumination condition, and volume inhibiting rate is respectively 61% and 52%, and carries the tumor control rate of medicine group Ergo-Ce6 NPs Reach 86.4%, hence it is evident that anticancer effect when higher than both independent using, this shows that Ce6 and Ergo NPs has apparent collaboration Anticarcinogenic effect, at the same this significant anticancer therapeutic of supermolecule photosensitizer Ergo-Ce6 NPs also further confirm it is active natural , it can be achieved that Synergistic anti-cancer purpose, is expected to realize clinical application after product delivery photosensitizer drug.
Fig. 8 is the changes of weight figure during mouse is treated through different pharmaceutical, it can be seen from the figure that mouse weight does not have substantially There is particularly apparent variation, in addition to other than administration weight loss occurs in second day, also having restored normal in subsequent treatment, this Illustrate that supermolecule photosensitizer drug Ergo-Ce6 NPs has good safety and biocompatibility, there is no apparent physiology Toxicity.This further illustrates, this bioactive natural product it be safely and effectively carrier.

Claims (7)

1. a kind of preparation method of the natural supermolecule photosensitizer of activity, it is characterised in that the method is with sterols carrier nanoparticle Son is carrier, using dihydro porphin photosensitizer Ce6 as medicine preparation activity supermolecule photosensitizer, the specific steps are as follows:
(1) in organic solvent by Ce6 dimethyl sulphoxide solution and sterols dissolution, be then added dropwise to 2.5% dropwise (quality/ Volume ratio) 0.25 ~ 2 min of polyvinyl alcohol water solution mesoscale eddies emulsification;
(2) 20 ~ 90s is emulsified using ultrasonic cell disintegration instrument under condition of ice bath;
(3) step (2) obtained lotion is added rapidly to 0.3%(mass/volume ratio) in polyvinyl alcohol water solution, room temperature It is protected from light magnetic agitation volatilization organic reagent;;
(4) centrifugation obtains active supermolecule photosensitizer, and is lyophilized and saves after being washed repeatedly with secondary distilled water.
2. the preparation method of the natural supermolecule photosensitizer of activity according to claim 1, it is characterised in that the sterols For ergosterol, stigmasterol or cupreol.
3. the preparation method of the natural supermolecule photosensitizer of activity according to claim 1, it is characterised in that described organic molten Agent is carbon tetrachloride, methylene chloride, chloroform or acetone.
4. the preparation method of the natural supermolecule photosensitizer of activity according to claim 1, it is characterised in that the Ce6 and steroid Mass ratio≤15% of alcohols, the quality of sterols and volume ratio≤10 of organic solvent, organic solvent and 2.5% polyvinyl alcohol water The volume ratio of solution is 1:1 ~ 5.
5. the preparation method of the natural supermolecule photosensitizer of activity according to claim 1, it is characterised in that described organic molten The volume ratio of agent and 0.3% polyvinyl alcohol water solution is 1:25 ~ 40, and magnetic stirring speed is 350 ~ 600 rpm.
6. the preparation method of the natural supermolecule photosensitizer of activity according to claim 1, it is characterised in that the Ce6 bis- The concentration of methyl sulfoxide solution≤15 mg/mL.
7. the active supermolecule photosensitizer that claim 1-6 any claim the method is prepared is in antineoplaston Application.
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