CN105561307B - Poly- N-phenylglycine optothermal material of sulfonation and the preparation method and application thereof - Google Patents
Poly- N-phenylglycine optothermal material of sulfonation and the preparation method and application thereof Download PDFInfo
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- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
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Abstract
The invention discloses poly- N-phenylglycine optothermal materials of a kind of sulfonation and the preparation method and application thereof.N-phenylglycine monomer is obtained poly- N-phenylglycine with ammonium persulfate oxidation polymerization by the present invention；By chlorosulfuric acid, sulfonic group is introduced on the aromatic ring structure of poly- N-phenylglycine to obtain the poly- N-phenylglycine of Water-soluble photothermal material sulfonation.This synthetic method raw material is easy to get, and synthesis technology is simple, and environmental pollution is small；The carboxyl on the poly- N-phenylglycine of sulfonation can be modified modification simultaneously, obtain the efficient high-molecular optical hot material with multiple functions, have application value in terms of the treatment of cancer；Using the photo-thermal therapy enhancing of poly- N-phenylglycine optothermal material to the killing rate of cancer cell, photo-thermal therapy, functional material, in terms of have wide practical use.
Description
Technical field
The present invention relates to photo-thermal therapy reagents, belong to biomedical material technology, and in particular to the poly- N- phenyl of sulfonation
Glycine optothermal material and the preparation method and application thereof.
Background technique
Photo-thermal therapy is, using the material with photo-thermal converting function, near infrared light to be absorbed, by luminous energy under laser irradiation
It is converted into thermal energy, generates high fever, and then realize the treatment to diseased region.With the technologies phase such as traditional operation, radiation and chemotherapy
Than, the advantages such as photo-thermal therapy has easy process, noninvasive or minimally invasive, few intercurrent disease, recovery is fast, the hospital stays is short, thus can have
It is ailing to imitate reduction of patient, improves patient outcomes.The wavelength of near-infrared laser used in photo-thermal therapy is 700 ~ 1100
Nm, with several centimetres of tissue penetration depths.Now, extensive optothermal material mainly includes inorganic material and organic material, nothing
Machine nano material mainly includes such as different noble metals (such as gold, silver, platinum) nanostructure, carbon nanometer and transition metal vulcanization
Object or oxide nano particles.Although all obtaining good therapeutic effect in preclinical animal model, these are inorganic
The not biodegradable and potential long term toxicity of nano material become Nano medication to the obstruction of clinic conversion.Due to depositing
These problems, organic photothermal reagent makes because of its good biocompatibility, optical stability, higher photothermal conversion efficiency
It becomes the nano material for potentially replacing inorganic light thermit powder.
Poly- N-phenylglycine is a kind of macromolecule of class polyaniline structure, and the difference with polyaniline is, on side chain
With carboxyl functional group, it is modified to be able to carry out chemical modification.And polyaniline be 2011 by South Korea professor Huh find its by with
The fatty acid cladding of Pegylation realize it is water-soluble after, can be used for cancer cell photo-thermal ablation (Yang, J. Choi,
D. Bang, E. Kim, E.-K. Lim, H. Park, J.-S. Suh, K. Lee, K.-H. Yoo, E.-K. Kim,
Y.-M. Huh, S. Haam. Angew. Chem. Int. Ed. 2011,50,441- 444.) there is research successively later
Report F127 (J. Zhou, Z. G. Lu, X. J. Zhu, X. J. Wang, Y. Liao, Z. F. Ma, F. Y.
Li. Biomaterials 2013,34,9584-9592.) and hyaluronic acid (B.-P. Jiang, L. Zhang, Y.
Zhu, X.-C. Shen, S.-C. Ji, X.-Y. Tan, L. Cheng, H. Liang. J. Mater. Chem. B,
2015,3,3767-3776) etc. the non-covalent compound water-soluble polyaniline nanoparticle that obtains carries out photo-thermal therapy.However, these are poly-
The functionalization of aniline composite nanoparticle is relatively simple, how to further increase therapeutic effect, and the toxicity for reducing photothermal reagent is
It needs to solve.Therefore, design and development function are more, and biocompatibility is high, and the good class polyaniline material of targeting induces one to close
Note.
Summary of the invention
Goal of the invention of the invention is: in view of the above problems, providing a kind of poly- N-phenylglycine light of sulfonation
Hot material and the preparation method and application thereof.Applied chemistry oxidizing process of the present invention synthesizes poly- N-phenylglycine (PGNP) nanoparticle
Son, then so that poly- N-phenylglycine (SPGNP) is had good water-soluble by sulfonation and study it to specific cancer site
Photo-thermal therapy effect.
In order to achieve the above-mentioned object of the invention, The technical solution adopted by the invention is as follows:
The poly- N-phenylglycine optothermal material of sulfonation, the optothermal material are prepared by following step:
(1) N-phenylglycine monomer, ammonium persulfate the preparation of poly- N-phenylglycine: are dissolved separately in acid solution
In, controlled at 0-5 DEG C, ammonium persulfate solution is slowly added dropwise into monomer solution, is added dropwise, reacts 2-10h, Zhi Housheng
To room temperature reaction 12-36h, filters and wash, dries, obtain poly- N-phenylglycine；
(2) preparation of the poly- N-phenylglycine of sulfonation: poly- N-phenylglycine is added into 1,2- dichloroethanes, ultrasound
Disperse and stir, is heated to 60 ~ 100 DEG C later, obtains dispersion；Chlorosulfonic acid 1,2- dichloroethanes is diluted, and slowly
It is added dropwise to above-mentioned dispersion, controlled at 60 ~ 100 DEG C, 5 ~ 15h is reacted, filters later, filter cake is hydrolyzed, re-dry is
Obtain the poly- N-phenylglycine of sulfonation.
Further, in step (1), the additional amount of the N-phenylglycine monomer and ammonium persulfate is equimolar amounts,
The acid solution is the H of 0.1-0.5M2SO4The HCL aqueous solution of aqueous solution or 0.5-2M, the time of the reaction are 0-5
3-8h is reacted at DEG C, reacts at room temperature 20-30h.For more abundant and thorough and easily controllable, the persulfuric acid for carrying out reaction
Aqueous ammonium needs slowly to be added dropwise, the in general described ammonium persulfate aqueous solution rate of addition are as follows: 1 ~ 2 ml/min.
Further, in order to ensure product quality, wherein remaining reactant is reduced to the greatest extent, in step (1), the washing
To be washed three times with distillation；The drying is in 40-60 DEG C of vacuum drying 48-96h.
Further, in step (2), the dispersion, poly- N-phenylglycine and 1, mole of 2- dichloroethanes
Than=1:550 ~ 750；Molar ratio=1:1.5 ~ 2.5 of the poly- N-phenylglycine and chlorosulfonic acid；The chlorosulfonic acid and dilution chlorine
Molar ratio=1:15 ~ 25 of sulfonic acid 1,2- dichloroethanes.
Further, in step (2), the ultrasonic time is 0.5 ~ 2 h, and frequency is 30 ~ 50KHz.The work of ultrasonic treatment
With being the particle that can separate aggregation, minuteness particle is avoided to be abandoned.
Further, in step (2), the rate of addition is 0.1 ~ 0.2mL/min；It is described to be filtered into suction filtration；The water
Solution reacts 3 ~ 5 h for filter cake to be immersed in 80 ~ 100 DEG C of water；The drying is that first vacuum is spin-dried for, and adds mistake after acetone is washed
Filter, is finally dried in vacuo.
The present invention also provides a kind of pharmaceutical composition, comprising at least one pharmaceutically acceptable carrier and described above
The poly- N-phenylglycine optothermal material of sulfonation.
The present invention also provides the poly- N-phenylglycine optothermal material of sulfonation described above and the pharmaceutical compositions
In the application for preparing anti-tumor drug.
Further, the dosage form of the anti-tumor drug include injection, oral agents, externally-applied liniment and it is other pharmaceutically
Suitable dosage forms.
Further, the tumour includes: melanoma, cervical carcinoma, breast cancer and colon cancer.
In the system of the poly- N-phenylglycine optothermal material of sulfonation of the invention, on the one hand, the poly- sweet ammonia of N- phenyl of sulfonation
Acid participates in the treatment of disease as photo-thermal therapy agent；On the other hand, sulfonic to introduce the water for improving poly- N-phenylglycine
Dissolubility enhances the application in terms of biology, which effectively can targetedly kill under Infrared irradiation
Dead cancer cell.
In conclusion by adopting the above-described technical solution, the beneficial effects of the present invention are:
(1) preparation method of the poly- N-phenylglycine optothermal material of the sulfonation is easy, and improves poly- N- by sulfonic group
The water solubility of phenylglycine；
(2) the resulting poly- N-phenylglycine optothermal material of the present invention can be evenly dispersed in aqueous systems and be stabilized
At least two is more than the moon；
(3) the killing rate of cancer cell is controlled in photo-thermal using the photo-thermal therapy enhancing of poly- N-phenylglycine optothermal material
Treatment, functional material, organizational project etc. have wide practical use.
Detailed description of the invention
Fig. 1 is the temperature of the poly- N-phenylglycine optothermal material aqueous solution of sulfonation of the invention with light application time variation diagram；
Fig. 2 is the poly- N-phenylglycine optothermal material aqueous solution UV absorption figure of sulfonation of the invention；
Fig. 3 is the infrared figure of poly- N-phenylglycine before and after sulfonation of the present invention；
Fig. 4 is cell survival rate figure after SPGNP acts on B16 and 4T1 24 hours under 650 nm (1W) laser irradiation；
Fig. 5 is cell survival rate figure after SPGNP acts on B16 and 4T1 24 hours under no light.
Specific embodiment
All features disclosed in this specification or disclosed all methods or in the process the step of, in addition to mutually exclusive
Feature and/or step other than, can combine in any way.
Any feature disclosed in this specification (including any accessory claim, abstract), unless specifically stated,
It is replaced by other equivalent or with similar purpose alternative features.That is, unless specifically stated, each feature is a series of
An example in equivalent or similar characteristics.
Prepare embodiment 1
(1) preparation of poly- N-phenylglycine: by monomer N-phenylglycine (1.06 g, 7 mmol) and oxidant over cure
Sour ammonium (1.60 g, 7 mmol) is dissolved separately in the H of 0.1M2SO4In, ice bath, keeping temperature is 0-5 DEG C, into monomer solution
Oxidant ammonium persulfate solution, time for adding 2h is added dropwise.It being added dropwise, ice bath the reaction was continued 5h is warmed to room temperature reaction for 24 hours,
Stop reaction.It filters and uses distillation washing three times.50 DEG C of vacuum drying 48h, obtain dark green solid, the as poly- sweet ammonia of N- phenyl
Acid.
(2) poly- N-phenylglycine (0.5 g, 0.3 mmol) preparation of the poly- N-phenylglycine of sulfonation: is added into (15
ML, 0.189mol) in 1,2- dichloroethanes, ultrasonic disperse and mechanical stirring, ultrasonic time are 1 h, frequency 40KHz；Later
80 DEG C are heated to, dispersion is obtained；By (0.078 g, 0.7 mmol) chlorosulfonic acid bis- chloroethene of (1mL, 0.0126mol) 1,2-
Alkane dilution, and (10 min) is slowly added dropwise into above-mentioned dispersion, controlled at 80 DEG C, 10h is reacted, is filtered later, it will
Filter cake, which is immersed in 100 DEG C of water, reacts 4 h, then vacuum is spin-dried for, and is added after acetone is washed and is filtered, and is finally dried in vacuo up to described
The poly- N-phenylglycine of sulfonation.
Prepare embodiment 2
(1) preparation of poly- N-phenylglycine: by monomer N-phenylglycine (1.06 g, 7 mmol) and oxidant over cure
Sour ammonium (1.60 g, 7 mmol) is dissolved separately in the HCl of 1 M, ice bath, and keeping temperature is 0-5 DEG C, is added dropwise into monomer solution
Oxidant ammonium persulfate solution, time for adding 2h.It is added dropwise, ice bath the reaction was continued 10h, is warmed to room temperature reaction 12h, stops
Reaction.It filters and uses distillation washing three times.40 DEG C of vacuum drying 96h, obtain dark green solid, as poly- N-phenylglycine.
(2) poly- N-phenylglycine (0.5 g, 0.3 mmol) preparation of the poly- N-phenylglycine of sulfonation: is added into (18
ML, 0.227mol) in 1,2- dichloroethanes, ultrasonic disperse and mechanical stirring, ultrasonic time are 2 h, frequency 30KHz；Later
80 DEG C are heated to, dispersion is obtained；By (0.052 g, 0.45 mmol) chlorosulfonic acid (1mL, 0.0126mol) 1,2- dichloro
Ethane dilution, and (10 min) is slowly added dropwise into above-mentioned dispersion, controlled at 60 DEG C, 15h is reacted, is filtered later,
Filter cake is immersed in 80 DEG C of water and reacts 5 h, then vacuum is spin-dried for, adds after acetone is washed and filters, is finally dried in vacuo up to institute
State the poly- N-phenylglycine of sulfonation.
Prepare embodiment 3
(1) preparation of poly- N-phenylglycine: by monomer N-phenylglycine (1.06 g, 7 mmol) and oxidant over cure
Sour ammonium (1.60 g, 7 mmol) is dissolved separately in the HCl of 1 M, ice bath, and keeping temperature is 0-5 DEG C, is added dropwise into monomer solution
Oxidant ammonium persulfate solution, time for adding 2h.It is added dropwise, ice bath the reaction was continued 3h, is warmed to room temperature reaction 30h, stops
Reaction.It filters and uses distillation washing three times.60 DEG C of vacuum drying 48h, obtain dark green solid, as poly- N-phenylglycine.
(2) preparation of the poly- N-phenylglycine of sulfonation: poly- N-phenylglycine (0.5 g, 0.3 mmol) is added into
In (13mL, 0.164mol) 1,2- dichloroethanes, ultrasonic disperse and mechanical stirring, ultrasonic time 0.5h, frequency 50KHz；
It is heated to 80 DEG C later, obtains dispersion；By (0.087g, 0.75 mmol) chlorosulfonic acid (1mL, 0.0126mol) 1,2- bis-
Chloroethanes dilution, and (10 min) is slowly added dropwise into above-mentioned dispersion, controlled at 100 DEG C, 5h is reacted, is taken out later
Filter, filter cake is immersed in 80 DEG C of water and reacts 5 h, then vacuum is spin-dried for get the poly- N-phenylglycine of the sulfonation.
Testing example 1
The poly- N-phenylglycine of sulfonation obtained in preparation embodiment is configured to the aqueous solution of 0.1 mg/mL, takes 1mL should
Solution is irradiated with 808nm laser (1W, spot diameter 5mm), with the temperature of infrared thermal imager recording solution with light application time
Variation.It is in 808 nm (1W cm referring to attached drawing 1-2) under laser irradiation, the poly- N-phenylglycine photo-thermal material of sulfonation of the invention
Expect the temperature of aqueous solution with light application time change curve.
As seen from the figure, with the increase of light application time, the temperature of the poly- N-phenylglycine aqueous solution of sulfonation is also significantly increased,
After irradiating 10 min, temperature increases 23 DEG C, and pure water only increases 0.2 DEG C under the conditions of same light is shone.Prove light of the invention
Hot material has good photo-thermal temperature rise effect.
Testing example 2
The poly- N-phenylglycine of the resulting sulfonation of embodiment will be prepared, the aqueous solution of 100 mg/mL is configured to, does purple respectively
Outer visible absorption spectra and infrared spectroscopy, respectively referring to attached drawing 2 and attached drawing 3；Wherein Fig. 2 is the purple of the poly- N-phenylglycine of sulfonation
Outer absorption figure, has extensive absorption in 500 ~ 700 nm ranges, it was demonstrated that can be used as photothermal reagent；Fig. 3 is before and after sulfonation
The poly- infrared figure of N-phenylglycine, 1078 cm-1It is S=O antisymmetry and symmetrical stretching vibration, 819 cm respectively-1It is poly- N-
There is phenylglycine aromatic ring 1,2,4- tri- to replace characteristic absorption peak, 800 ~ 600 cm-1Between absorption peak be C-S, C-O
Group stretching vibration, these all show to introduce-SO3。
Application Example 1
Inoculated L929 tissue culture plate is put into incubator and is cultivated, (96 holes are flat until cell monolayer is paved with bottom hole
Plate), the poly- N-phenylglycine of sulfonation (0,10,50,100,150,200,250,300,350, the 400 μ g/ of various concentration is added
ML), it is incubated for 24 h.10 uL MTT solution are added in every hole, continue to cultivate 4 h.After 4 h of culture are added in MTT, culture medium is discarded, so
100 uL dimethyl sulfoxides (DMSO) are added in every hole afterwards, set 10 min of low-speed oscillation on shaking table, dissolve crystal sufficiently.In enzyme
The light absorption value for joining each hole of measurement at immune detector OD490 nm is shown in Table 1 as the poly- N-phenylglycine effect of various concentration sulfonation
In the absorbance value of L929 cell.These are statistics indicate that the dark toxicity effect of the cell in vitro of the poly- N-phenylglycine of sulfonation can be with
It ignores.
Application Example 2
A series of poly- N-phenylglycine solution of sulfonation of concentration (0-100 μ g/mL) is respectively configured.By murine melanoma
Cell (B16 cell) and mouse mastopathy cell (4T1 cell) are in 96 orifice plates (every hole 104A cell) in culture.After diel,
The poly- N-phenylglycine solution of sulfonation of prepared series of concentrations is added, is further cultured for 24 hours.Respectively with 650 nm laser
(1W) irradiates 5 min.It is further cultured for 24 hours, surveys cell inhibitory rate (inhibiting rate (%)=(1- test hole OD with MTT method
Value/control wells OD value) × 100%).It is the ug of SPGNP(0 ~ 100 mL under 650 nm (1W) laser irradiation referring to attached drawing 4-1)
Cell survival rate figure after acting on 24 hours B16 and 4T1；Attached drawing 5 is the ug of SPGNP(0 ~ 100 mL under no light-1) to B16
And cell survival rate figure after 4T1 effect 24 hours.Attached drawing shows under 650 nm laser (1W) irradiation conditions, display pair in plate
The killing rate of cell are up to 72%；And the display cell survival rate of no light is more than 74%.Experiment confirms poly- N-phenylglycine
Photo-thermal therapy has good killing rate to mouse melanin tumor cell (B16 cell) and mouse mastopathy cell (4T1 cell).
Application Example 3
According to the same methods experiment of Application Example 2, it was demonstrated that poly- N-phenylglycine photo-thermal therapy is thin to human colon carcinoma
Born of the same parents' (HCT-116 cell), human cervical carcinoma cell (HeLa cell) also have good killing rate.
The invention is not limited to specific embodiments above-mentioned.The present invention, which expands to, any in the present specification to be disclosed
New feature or any new combination, and disclose any new method or process the step of or any new combination.
Claims (9)
1. the poly- N-phenylglycine optothermal material of sulfonation, which is characterized in that the optothermal material is prepared by following step:
(1) preparation of poly- N-phenylglycine: N-phenylglycine monomer, ammonium persulfate are dissolved separately in acid solution,
Controlled at 0-5 DEG C, ammonium persulfate solution is slowly added dropwise into monomer solution, is added dropwise, reacts 2-10h, rises to later
12-36h is reacted at room temperature, filters and washes, dry, obtain poly- N-phenylglycine；
(2) preparation of the poly- N-phenylglycine of sulfonation: poly- N-phenylglycine is added into 1,2- dichloroethanes, poly- N- phenyl
Glycine and 1, molar ratio=1:550 ~ 750 of 2- dichloroethanes, ultrasonic disperse simultaneously stir, are heated to 60 ~ 100 DEG C later, obtain
Dispersion；Chlorosulfonic acid 1,2- dichloroethanes is diluted, the chlorosulfonic acid and dilution chlorosulfonic acid rubbing with 1,2- dichloroethanes
That ratio=1:15 ~ 25, and be slowly added dropwise to above-mentioned dispersion, molar ratio=1 of the poly- N-phenylglycine and chlorosulfonic acid:
1.5~2.5；Controlled at 60 ~ 100 DEG C, 5 ~ 15h is reacted, filters later, filter cake is hydrolyzed, re-dry is poly- up to the sulfonation
N-phenylglycine.
2. the poly- N-phenylglycine optothermal material of sulfonation according to claim 1, it is characterised in that: described in step (1)
The additional amount of N-phenylglycine monomer and ammonium persulfate is equimolar amounts, and the acid solution is the H of 0.1-0.5M2SO4Water
The HCL aqueous solution of solution or 0.5-2M, the time of the reaction are that 3-8h is reacted at 0-5 DEG C, react at room temperature 20-30h.
3. the poly- N-phenylglycine optothermal material of sulfonation according to claim 1, it is characterised in that: described in step (1)
Washing distills washing three times to use；The drying is in 40-60 DEG C of vacuum drying 48-96h.
4. the poly- N-phenylglycine optothermal material of sulfonation according to claim 1, it is characterised in that: described in step (2)
Ultrasonic time is 0.5 ~ 2 h, and frequency is 30 ~ 50KHz.
5. the poly- N-phenylglycine optothermal material of sulfonation according to claim 1, it is characterised in that: described in step (2)
Rate of addition is 0.1 ~ 0.2mL/min；It is described to be filtered into suction filtration；It is described be hydrolyzed to for filter cake to be immersed in 80 ~ 100 DEG C of water react
3~5 h；The drying is that first vacuum is spin-dried for, and adds after acetone is washed and filters, is finally dried in vacuo.
6. a kind of pharmaceutical composition includes at least one pharmaceutically acceptable carrier and the poly- N- of sulfonation described in claim 1
Phenylglycine optothermal material.
7. the poly- N-phenylglycine optothermal material of sulfonation described in claim 1 or pharmaceutical composition as claimed in claim 6 exist
Prepare the application of anti-tumor drug.
8. application according to claim 7, it is characterised in that: the dosage form of anti-tumor drug is injection, oral agents or outer
Use liniment.
9. application according to claim 7, it is characterised in that: the tumour is melanoma, cervical carcinoma, breast cancer or knot
Intestinal cancer.
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| Title |
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| Chemical Synthesis and Characterization of Water-soluble, Conducting Poly (N-phenylglycine);Mohammad Reza Nabid et al.;《Iranian Polymer Journal》;20081231;第17卷(第5期);第365-371页 |
| 水溶性磺化聚苯胺的合成研究;李斌等;《广州化工》;20111231;第39卷(第5期);第4-5、22页 |
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