CN108129475A - A kind of biology photosensitizer and its preparation method and application - Google Patents
A kind of biology photosensitizer and its preparation method and application Download PDFInfo
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- A61K41/0057—Photodynamic therapy with a photosensitizer, i.e. agent able to produce reactive oxygen species upon exposure to light or radiation, e.g. UV or visible light; photocleavage of nucleic acids with an agent
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Abstract
The invention discloses a kind of biological photosensitizers and its preparation method and application, while the photosensitizer has both the targeting of photosensitizer in itself and kills characteristics of tumor cells, the EGF-R ELISA in bio-tissue can be activated again, while killing destroys tumor tissues, promote organization healing, the biology photosensitizer efficiently can quickly kill squamous cell carcinoma, promote skin repair, and the side effect of drug response is minimum.
Description
Technical field
The present invention relates to a kind of biological photosensitizers and its preparation method and application, belong to biomedicine field.
Background technology
Squamous cell carcinoma is one kind of cutaneum carcinoma.It is mainly characterized by：From the beginning of swelling lump for defect shape, substrate is hard, friend
Face is coarse such as cauliflower-shaped, it is seen that telangiectasis, the common sting sample cutin in top.
Photodynamic therapy (Photodynamic Therapy, PDT) was come out the seventies in last century, and core strategy is
Using the light of specific wavelength, irradiation selectivity is accumulated in the photosensitizer of lesion, and it is cytotoxic that photosensitizer activation generates tool
Singlet oxygen and reactive oxygen species, so as to kill cell.
Photodynamic therapy in the evolution of more than 30 years of China be applied successfully to treatment infantile tumour, superficial
The non-tumor diseases such as the nevus flammeus of tumour and other non-tumours, condyloma acuminatum.This therapy is woven with tumor group certain choosing
Selecting property, toxic side effect is small, makes patient from the risky operation of general anesthesia, and in simple local anaesthesia menisectomy, it is simple easily
It is capable and safe.
Ideal photosensitizer should have following characteristic：(1) tumor-selective uptake ratio is high, and is easy to be metabolized；(2) by π-
The maximum absorption wavelength of Q bands caused by π transition, which should be located at, penetrates the strong red light district of organizational capacity (670-850nm)；(3) in feux rouges
The lower triplet quantum yield of excitation is high, long lifespan；(4) it is weak to natural light absorption, it is small to the phototoxicity of skin；(5) chemical property
Stablize, low toxicity.Meet above-mentioned requirements as second generation photosensitizer phthalocyanine-like compound, therefore be ideal photosensitizer.But
Phthalocyanines photosensitizer there are one it is common the shortcomings that, i.e., its dissolubility in water-soluble solvent and fat-soluble solvent is not high,
This affects its transhipment in vivo and the accumulation ability on tumor tissues.
But up to the present, the photosensitizer of exploitation still has shortcoming, although having now been developed thousands of kinds in the world not
The photosensitizer of same type, but be less able to be applied to clinic, find the preferable photosensitizer suitable for human body diseases photodynamic therapy
Extremely difficult, it is that photosensitizer targeting ability is inadequate to entangle its reason one, it is difficult to is enriched at tumor tissues completely, second is that photosensitizer is big
It mostly easily unites in human body in hydrophobic molecule and is not easy to transport, so non-Non-specific positioning belt carrys out non-Non-specific activation, after
And unexpected toxic reaction is caused to human normal tissue.Caused of short duration aphasia or treatment during for treating tongue cancer
Liver cancer is the toxic effects such as caused slight low-heat abdominal pain.These light or heavy toxic reactions are reflected in appearance beauty
More demanding skin perineum etc., which is sentenced, causes patient heavier physical and mental burden.Therefore a kind of novel photosensitizing agents are provided
Skin cancer is the Critical policies of optical dynamic therapy.
EGF is a kind of important growth factor for being worked by receptor and stimulating cellular proliferation and breaking up, abnormal expression with
Automatic growth, aggressivity, the Angiogensis of cancer cell are related with the appearance of remote transfer etc..The surface of normal cell
There are an EGF receptors, but many tumour especially solid tumor cell surfaces then have the height expression of the EGF receptor of unusual high levels reachable
100 times or more of normal quantity, therefore photosensitizer can be quickly and accurately directed to tumor group by EGF as a kind of targeting sequencing
It knits.So as to reduce non-specific aggregation and delay of the photosensitizer in normal structure.
In addition in the mechanism of action in cellular elements level, Wnt signal pathways can cause intracellular β-linkage protein (β-
Catenin it) accumulates.β-catenin (being called tatou albumin A rmadillo in drosophila) are a kind of multi-functional protein,
It interacts cell junctions with cadherins, and participation forms adhesive tape, and free β-catenin can enter nucleus, adjusts
Save gene expression.Wnt signals play an important role in animal development, and unconventionality expression or activation can cause tumour.
Although researcher is found that many members of Wnt signal paths very early, until 10 years, Ren Mencai
Really Wnt signal paths and cancer are connected.With going deep into for future studies, we expect more Wnt signal paths with
The discovery of relation between tumor.The research of the mutual synergistic mechanism of intracellular signaling pathway can design significantly more efficient anticancer for us
Drug provides more theoretical foundations.
Invention content
For above-mentioned technical problem, the purpose of the present invention is to provide Skin Squamous Cell Carcinoma cell biology features of combining closely
A kind of Small side effects, Efficient killing effect tumour cell and the new bio photosensitizer for protecting normal structure.
The technical scheme is that providing a kind of biological photosensitizer (abbreviation EtNBSe-PDT), structural formula is：
The present invention also provides the preparation methods of the biological photosensitizer, include the following steps：
(1) by reactantAnd reactant
It is 70-100 DEG C that temperature is heated in the organic solvent containing inorganic base, reacts 16-24 hours, intermediate product A is obtained, in described
Between the structural formula of product A be：
Using benzene as solvent, by reactant
And reactantIt is reacted at 50-60 DEG C, obtains intermediate product B, the structural formula of the intermediate product B is：
(2) using alcohol as solvent, intermediate product A and intermediate product B are heated to reflux 24-48 hours under protective atmosphere,
Mixture after reaction is purified to obtain the biological photosensitizer.
Preferably, in the step of preparing intermediate product A, reactant
And reactantMolar ratio be 1: 1.
Preferably, in the step of preparing intermediate product B, reactant
And reactantMolar ratio be 1:4.0-4.5.
Preferably, in step (2), the molar ratio between intermediate product A and intermediate product B is 1:3.2-4.5.
Preferably, in step (2), using ethyl alcohol as reaction dissolvent, the volume of ethyl alcohol is the 200-300 of reactant total volume
Times.
The present invention also provides above-mentioned biological photosensitizers to prepare the application in treating skin cancer drug.
Preferably, the cutaneum carcinoma is Skin Squamous Cell Carcinoma.
The photosensitizer has certain dissolubility in water-soluble solvent and fat-soluble solvent.Excite the light of the photosensitizer
It is ultraviolet light or visible light, preferably feux rouges.Light source used is：Ultrasonic irradiation generator, photoemitted electron pipe, electronic laser
The daylight or white heat that pipe, fuel laser, halogen family metalized lamp, flash lamp, the fluorescent light source of machinery filtration, daylight or machinery filter
It is one or more in line source.When light excitation includes the composition of photosensitizer, to optical wavelength, also there is no limit, it is contemplated that penetrates
Effect, preferably 280-1000nm, optimal wavelength range are 650-690nm.Optimal wavelength of the present invention is in the feux rouges of 650-690nm.
Biological photosensitizer can be used for killing squamous cell carcinoma, and Skin Squamous Cell Carcinoma is mainly characterized by：From the beginning of swollen for defect shape protuberance
Block, substrate is hard, rough surface such as cauliflower-shaped, it is seen that telangiectasis, the common sting sample cutin in top.
The biology photosensitizer is activated when light irradiates, and by inhibiting wnt/ β-catenin signal paths, promotes tumour
Cell generates apoptosis, has the effect of fine to squamous cell carcinoma.Also, the biology photosensitizer can be with the table of skin histology
Skin growth factor receptor is combined, and promotes the healing of skin histology by epidermal growth factor-like effect.
The invention has the advantages that the biological photosensitizer of the present invention has both the targeting of photosensitizer in itself and kills tumour
While cellular features, and the EGF-R ELISA in bio-tissue can be activated, tumor tissues are destroyed in killing
Meanwhile promote organization healing, which efficiently can quickly kill squamous cell carcinoma, promote skin repair, drug response
Side effect it is minimum.
Description of the drawings
Fig. 1 shows for treating the chemical structural formula of the biological photosensitizer of Skin Squamous Cell Carcinoma.
Fig. 2 represents to compose for treating the hydrogen of the biological photosensitizer of Skin Squamous Cell Carcinoma.
Fig. 3 represents to compose for treating the carbon of the biological photosensitizer of Skin Squamous Cell Carcinoma.
Fig. 4 represents A431 squamous cell carcinoma fluidic cell figures.
Fig. 5 represents wnt signal path GAP-associated protein GAP Western Blot result figures.
Fig. 6 represents wnt signal path GAP-associated protein GAP Western Blot result figures after intervening.
Fig. 7 represents apoptosis-related protein immunocyte fluorescence results figure
Fig. 8 shows apoptosis-related protein Western Blot result figures.
Specific embodiment
With reference to embodiment, the invention will be further described.
Embodiment 1：The synthesis of EtNBSe-PDT
Intermediate product A is prepared, reaction condition is：It is anti-for 70-100 DEG C that temperature is heated in the organic solvent containing inorganic base
It answers 16-24 hours, wherein the molar ratio of two reactants is 1:1.
Reaction route is as follows：
Intermediate product B is prepared, reaction condition is：In the solvent of benzene, 50-60 degrees Celsius, two reactant molar ratios are 1:
4- 4.5.Reaction route is as follows：
Prepare EtNBSe-PDT：By the obtained intermediate product A of step (1) and the obtained intermediate product B of step (2)
It carries out that final product is obtained by the reaction, wherein the molar ratio of two reactants is 1：3.2-4.5, with 200-300 times of second of reactant volume
Alcohol is heated to reflux 24-48 hours, after reaction, is cooled to room temperature, solvent is removed in vacuo under protection of argon gas as solvent,
Using dichloromethane as solvent, silica gel chromatograph column separating purification, vacuum drying obtains final product.The structural formula of EtNBSe-PDT
As shown in Figure 1, its nucleus magnetic hydrogen spectrum and carbon spectrum difference are as shown in Figures 2 and 3.
Embodiment 2：EtNBSe-PDT makes epithelioma generate apoptosis embodiment
Annexin V are a kind of reagents for detecting Apoptosis, and in normal cell, phosphatidylserine is only distributed in carefully
The inside of after birth double-layer of lipoid, apoptosis early stage, membrane phospholipid acyl serine (PS) in adipose membrane by turning on one's side outward.Therefore
Annexin V are the sensitive indexes for detecting early apoptosis of cells.PI (propidium iodide) is a kind of nuclei dyeing that can be dyed to DNA
Color reagent, can be across damaged cell membrane and to nuclear staining although PI cannot be by living cells film.Therefore Annexin V
Being used in combination with PI can be simultaneously to living cells and dead cell stain.According to fluidic cell map analysis, in the effect of EtNBSe- PDT
Under, apoptosis cell significantly increases compared with blank group, it was demonstrated that EtNBSe-PDT can by inducing apoptosis of tumour cell, to reach
Antitumor purpose.
(1) experimental method
Squamous cell carcinoma A-431 cell lines are incubated in the DMEM culture solutions of 10% calf serum, add the mould of 100IU/L
The streptomysin of element and 100mg/L, is placed in 37 DEG C, and routine culture in the constant incubator of 5%CO2 after cell covers with bottom of bottle, is abandoned
Fall culture solution, PBS liquid rinses twice, then is digested 5 minutes, then sub-bottle culture with 0.25% pancreatin and 0.02% EDTA, 2 to
Passage in 3 days is primary, and growth period cell of taking the logarithm is used to test.
The A-431 cells in growth period of taking the logarithm are inoculated in after pancreatin digests in six well culture plates, are placed in 5%CO2 cultures
Case, 37 DEG C of cultures, it is to be grown to 80%~90% Fusion Strain when, be separately added into 400nM distilled water, 600nM EtNBSe,
(pp2a inhibits by 600nM EtNBSe+GSK3 β inhibitor (GSK3 beta inhibitors) and 600nM EtNBSe+Okadaic acid
Agent) be incubated 1h after, use 20J/cm2Red light irradiation 15min, 16h after with Annexin V-PI dye, pass through FACSCalibur
Flow cytometer observe the situation of apoptosis.
(2) experimental result
Flow cytometer detection is the results show that the A-431 cells Apoptosis that 16h is generated after EtNBSe-PDT increases than blank group
48.8% (Fig. 4) is added, GSK3 beta inhibitors, which can be obviously promoted Apoptosis, in EtNBSe-PDT joints increases by 59.8%, simultaneously
EtNBSe-PDT joint pp2a inhibitor can slightly improve the Apoptosis 13.8% of EtNBSe-PDT inductions.From interpretation of result,
600nM EtNBSe-PDT can significantly induce squamous cell carcinoma to generate apoptosis, and by inhibiting Wnt signals that can be obviously promoted
The ability of EtNBSe-PDT inducing cell apoptosis.
Embodiment 3：EtNBSe-PDT inhibits Wnt signal embodiments
Wnt signal paths generally refer to the classical Wnt signal path mediated by β-Catenin.There is no Wnt signals
When, phosphate group can be added on the serine/threonine residue of β-Catenin N-terminals by GSK3 β, the β-Catenin of phosphorylation
After β-TRCP ubiquitination covalent modifications, degraded by proteasome (proteasome).And PP2A is sloughed in Wnt accesses
The phosphorylation of GSK3 β can be obviously promoted Wnt signals.Therefore by measuring GSK3 β, β-Catenin and the phosphorylation state of PP2A
It can be directly acquainted with whether Wnt signals activate.Wnt signal paths are as a kind of highly conserved signal path in evolution, in life
It plays a significant role during the various biologicals such as long, development, metabolism and stem cell maintenance, root closely related with tumour growth
According to Western Blot result map analysis, under the action of EtNBSe-PDT, a series of variations occur for Wint signal related proteins,
Inhibit Wint signals.
(1) experimental method
Squamous cell carcinoma A-431 cell lines are incubated in the DMEM culture solutions of 10% calf serum, add the mould of 100IU/L
The streptomysin of element and 100mg/L, is placed in 37 DEG C, and routine culture in the constant incubator of 5%CO2 after cell covers with bottom of bottle, is abandoned
Fall culture solution, PBS liquid rinses twice, then is digested 5 minutes, then sub-bottle culture with 0.25% pancreatin and 0.02% EDTA, 2 to
Passage in 3 days is primary, and growth period cell of taking the logarithm is used to test.
The A-431 cells in growth period of taking the logarithm are inoculated in after pancreatin digests in six well culture plates, are placed in 5%CO2 cultures
Case, 37 DEG C culture, it is to be grown to 80%~90% Fusion Strain when, 600nM EtNBSe medicaments are separately added into every hole, are incubated
After educating 1h, 20J/cm is used2Red light irradiation 15min, respectively at 0h, 0.5h, 1h, 2h, 8h and 16h collect cell extraction total protein
P-GSK3 β and p-PP2A in cell are detected with Western Blot methods.In addition, the A-431 cells in growth period of taking the logarithm are through pancreatin
It is inoculated in after digestion in six well culture plates, is placed in 5%CO2 incubators, 37 DEG C of cultures are to be grown to 80%~90% Fusion Strain
When, distilled water, hydrogen peroxide, epidermal growth factor (EGF) and 600nM EtNBSe medicaments are separately added into every hole, is incubated 1h
Afterwards, 20J/cm is used2Red light irradiation 15min, collected after 0.5h cell extraction total protein detected with Western Blot methods it is thin
P-GSK3 β, p- β-catenin and p-PP2A in born of the same parents.
(2) experimental result
Fig. 5 and Fig. 6 show that time gradient observes p-GSK3 β and p- in cell after EtNBSe-PDT processing A-431 cells
PP2A dynamic change interpretations of result, EtNBSe-PDT can significantly inhibit p-GSK3 β and p-PP2A from 0.5h to 16h.Because GSK3 β
With phosphorylation time of PP2A quickly, we determine that 0.5h collects EtNBSe-PDT pairs of cell observation after EtNBSe-PDT processing
Wnt/ β-catenin effect of signals.The results show that EtNBSe-PDT can be obviously promoted p- β-Catenin compared with blank control
Increase, effect be better than H2O2.EtNBSe-PDT can significantly inhibit p-PP2A, although H2O2To the inhibition ratio of p-PP2A
EtNBSe-PDT effects are good.EGF can be obviously promoted p-GSK3 β, and GSK3 β inactivations is made to shield cell, and EtNBSe-
PDT significantly inhibits the phosphorylation of GSK3 β.To sum up, EtNBSe- PDT can significantly inhibit Wnt/ β-catenin signals.
Embodiment 4EtNBSe-PDT can be significantly by inhibiting Wnt/ β-catenin signals to promote A-431 Apoptosis
Caspase-3 and Bcl-2 is the important indicator of Apoptosis, and Caspase-3 expression increases and Bcl-2 expression quantity
Inhibition is the important symbol that cell generates apoptosis.According to immunocyte fluorescent result figure, under EtNBSe-PDT effects,
Respective change occurs for Caspase-3 and Bcl-2 expression quantity, and Apoptosis is prompted to increase；According to Western Blot result figures,
Under EtNBSe- PDT effects, Wint signal related proteins accordingly change, and Wint signals are suppressed.Illustrate EtNBSe-PDT energy
Significantly by the way that Wnt/ β-catenin signals is inhibited to promote A-431 Apoptosis.
(1) experimental method
Squamous cell carcinoma A-431 cell lines are incubated in the DMEM culture solutions of 10% calf serum, add the mould of 100IU/L
The streptomysin of element and 100mg/L, is placed in 37 DEG C, and routine culture in the constant incubator of 5%CO2 after cell covers with bottom of bottle, is abandoned
Fall culture solution, PBS liquid rinses twice, then is digested 5 minutes, then sub-bottle culture with 0.25% pancreatin and 0.02% EDTA, 2
Primary to passage in 3 days, growth period cell of taking the logarithm is used to test.
The A-431 cells in growth period of taking the logarithm are inoculated in after pancreatin digests in six well culture plates, are placed in 5%CO2 cultures
Case, 37 DEG C culture, it is to be grown to 80%~90% Fusion Strain when, be separately added into every hole distilled water, hydrogen peroxide and
EtNBSe medicaments after being incubated 1h, use 20J/cm2Red light irradiation 15min, pass through Cyto- after 16h
The expression quantity of Caspase-3 and Bcl-2 in immunofluorescence observation cells.In addition, the A-431 in growth period of taking the logarithm
Cell is inoculated in after pancreatin digests in six well culture plates, is placed in 5%CO2 incubators, 37 DEG C of cultures, it is to be grown to 80%~
During 90% Fusion Strain, be separately added into every hole distilled water, EtNBSe, EtNBSe+GSK3 β (GSK3 beta inhibitors) and
After EtNBSe+Okadaic acid (pp2a inhibitor) are incubated 1h, 20J/cm is used2Red light irradiation 15min, 16h after with collect
Cell extraction total protein detects Caspase-3 and Bcl-2 in cell with Western Blot methods.
(2) experimental result
Cyto-immunofluorescence results show that EtNBSe-PDT can be obviously promoted the expression quantity of Caspase-3,
Although the effect of hydrogen peroxide is better than EtNBSe-PDT.EtNBSe-PDT can significantly inhibit the expression of Bcl-2 simultaneously, and effect is better than
Hydrogen peroxide.Western Blot are the results show that EtNBSe-PDT combination GSK3 beta inhibitors or pp2a inhibitor can be obviously promoted
EtNBSe-PDT increases the expression quantity of Caspase-3.EtNBSe-PDT can be apparent with EtNBSe-PDT combination pp2a inhibitor
Inhibit the expression of Bcl-2, although EtNBSe-PDT combination GSK3 beta inhibitors can promote the expression of Bcl-2.As a result illustrate
EtNBSe-PDT can be by inhibiting Wnt/ β-catenin signals to promote squamous cell carcinoma apoptosis (Fig. 7, Fig. 8).
Claims (8)
1. a kind of biology photosensitizer, which is characterized in that the structural formula of the biology photosensitizer is：
2. a kind of preparation method of biological photosensitizer described in claim 1, which is characterized in that include the following steps：
(1) by reactantAnd reactant
It is 70-100 DEG C that temperature is heated in organic solvent containing inorganic base, reacts 16-24 hours, obtains intermediate product A, the centre
The structural formula of product A is：
Using benzene as solvent, by reactantWith it is anti-
Answer objectIt is reacted at 50-60 DEG C, obtains intermediate product B, the structural formula of the intermediate product B is：
(2) using alcohol as solvent, intermediate product A and intermediate product B under protective atmosphere are heated to reflux 24-48 hours, reacted
Rear mixture is purified to obtain the biological photosensitizer.
3. preparation method as claimed in claim 2, which is characterized in that in the step of preparing intermediate product A, reactantAnd reactantMolar ratio
It is 1:1.
4. preparation method as claimed in claim 2, which is characterized in that in the step of preparing intermediate product B, reactantAnd reactantRub
You are than being 1:4.0-4.5.
5. preparation method as claimed in claim 2, which is characterized in that in step (2), between intermediate product A and intermediate product B
Molar ratio be 1:3.2-4.5.
6. preparation method as claimed in claim 2, which is characterized in that in step (2), using ethyl alcohol as reaction dissolvent, ethyl alcohol
Volume be 200-300 times of reactant total volume.
7. biology photosensitizer described in claim 1 is preparing the application in treating skin cancer drug.
8. the use as claimed in claim 7, which is characterized in that the cutaneum carcinoma is Skin Squamous Cell Carcinoma.
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| CN109350742A (en) * | 2018-11-26 | 2019-02-19 | 中南大学湘雅三医院 | A kind of bipolarity photosensitizer and preparation method thereof |
| CN109513004A (en) * | 2018-11-26 | 2019-03-26 | 中南大学湘雅三医院 | A kind of photosensitizer and preparation method thereof for photodynamic therapy |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109350742A (en) * | 2018-11-26 | 2019-02-19 | 中南大学湘雅三医院 | A kind of bipolarity photosensitizer and preparation method thereof |
| CN109513004A (en) * | 2018-11-26 | 2019-03-26 | 中南大学湘雅三医院 | A kind of photosensitizer and preparation method thereof for photodynamic therapy |
| CN109350742B (en) * | 2018-11-26 | 2021-04-23 | 中南大学湘雅三医院 | Bipolar photosensitizer and preparation method thereof |
| CN109513004B (en) * | 2018-11-26 | 2021-07-23 | 中南大学湘雅三医院 | Photosensitizer for photodynamic therapy and preparation method thereof |
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