CN108047462B - Preparation method and application of hydrogel based on poly N-phenylglycine-polyethylene glycol - Google Patents

Preparation method and application of hydrogel based on poly N-phenylglycine-polyethylene glycol Download PDF

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CN108047462B
CN108047462B CN201711492377.3A CN201711492377A CN108047462B CN 108047462 B CN108047462 B CN 108047462B CN 201711492377 A CN201711492377 A CN 201711492377A CN 108047462 B CN108047462 B CN 108047462B
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沈星灿
胡海露
刘婵娟
石睿
卢钰
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Guangxi Normal University
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    • C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
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Abstract

The invention discloses a preparation method and application of a poly-N-phenylglycine-polyethylene glycol hydrogel. The ultraviolet absorption peak of the hydrogel prepared by the invention is transferred to the near-infrared second window, and the laser irradiation of the near-infrared second window can increase the laser penetration depth, reduce the absorption of living tissues to the laser and reduce the damage to normal tissues. The hydrogel has temperature and shear sensitive dual-response injectable intelligent hydrogel, can load chemotherapeutic drugs so as to realize the fixed-point release according to the needs of the drugs, and is a photo-thermal hydrogel carrying system for enhancing chemotherapy and photo-thermal combined treatment.

Description

Preparation method and application of hydrogel based on poly N-phenylglycine-polyethylene glycol
Technical Field
The invention relates to a photothermal treatment reagent, belongs to the technical field of biomedical materials, and particularly relates to a preparation method based on poly-N-phenylglycine-polyethylene glycol hydrogel and application of the hydrogel in a near-infrared second window.
Background
Photothermal therapy is a therapy in which a photothermal material absorbs near-infrared light under laser irradiation, and converts light energy into heat energy to generate hyperthermia in tumor tissues, thereby killing diseased cells. It has the characteristics of accuracy, high efficiency, controllability, no wound, low side effect and the like. In recent years, near-infrared laser light has been widely used for thermal treatment because of its high penetration ability into living tissue. The absorption of most nano particles is in a near-infrared first window (750 nm-900 nm), and compared with the absorption and scattering of the near-infrared second window laser to blood and living tissues are smaller, so that the nano particles have stronger penetrating power to the living tissues. Therefore, the study of hyperthermia nanoparticles with a second window of absorption in the near infrared is an area worth exploring and developing. The existing photothermal therapy is usually carried out by preparing photothermal nanoparticles or hydrogel preparations from photothermal materials. The intelligent photothermal hydrogel has the characteristics of in-situ injection and repeated treatment, and has better curative effect on the easily recurrent tumor. Meanwhile, the hydrogel has photo-thermal triggered temperature responsiveness, can be used for fixed-point release according to needs of drug loading, and is more intelligent and controllable.
poly-N-phenylglycine is a polymer with a polyaniline-like structure, polyaniline can be doped by Lewis acid, transition metal, alkali metal ions and the like, and a benzene-benzene structure of a polyaniline skeleton can be converted into a benzene-quinone structure, so that an ultraviolet-visible absorption peak is red-shifted to a near-infrared region. This feature makes polyaniline have the potential to be used as a photothermal reagent. In 2011, after the polyethylene glycol fatty acid is modified on polyaniline to achieve water solubility by Yang and the like, the polyethylene glycol fatty acid is used for photothermal ablation treatment of cancer cells (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), F127(J. Zhou, Z.G. Lu, X.J. Zhu, X.J. Wang, Y. Liao, Z.F. Ma, F.Y. Li. Biomaterials 2013, 34, 9584. Bu. 92.) and hyaluronic acid (B, P. Jiang, Shu. Zhan, Y. Zhan. C., T. C. T. H. Yo. H. Yo, E. Kim, Y. K. Kim, Y. H, h, Liang, J, mater, chem, B, 2015, 3, 3767-3776) and the like to obtain non-covalent composite water-soluble polyaniline nanoparticles for photothermal therapy. The laser of the prepared polyaniline polymer photothermal reagent is the laser of a near-infrared first window, but no report on treatment by the laser of a near-infrared second window prepared into photothermal hydrogel is reported.
Cyclodextrin is a cyclic oligosaccharide extracted from starch, and can be subjected to subject-object self-assembly with macromolecules to form pseudo-polyrotaxane gel due to the structure of hydrophobic inner cavity and hydrophilic outer cavity. In 1994, a Japanese scientist study found that cyclodextrin (α -CD) forms supramolecular hydrogels with high molecular weight. alpha-CD can act on PEG chain ends through recognition of a host and an object to form a pipe-shaped pseudopolyrotaxane structure (PPR), physical cross-linking points are formed by utilizing strong hydrogen bonding between PPRs, and the physical cross-linking points and the PEG chains which are not included act together to form hydrogel with a three-dimensional space network structure. And the hydrogel is found to have the phase transition property of temperature-sensitive sol-gel reversible transition. Thereafter, a great deal of literature reports that cyclodextrin and linear, comb, star and tree macromolecules undergo host-guest self-assembly to form cyclodextrin-based polyrotaxane supramolecular (CD-PPR) hydrogel. CD-PPR hydrogel generally has double intelligent responsivity of shear sensitivity and temperature sensitivity, and is widely used for controlled drug release research.
Disclosure of Invention
The invention aims to provide a preparation method and application of a poly-N-phenylglycine-polyethylene glycol hydrogel, wherein the hydrogel has high photo-thermal conversion efficiency under the laser irradiation of a near-infrared light second window, can load chemotherapeutic drugs and realizes chemotherapy and photo-thermal synergistic treatment.
The preparation method of the hydrogel based on poly N-phenylglycine-polyethylene glycol comprises the following steps:
(1) preparation of Poly-N-phenylglycine-polyethylene glycol nanocomposite (PPG-PEG)
Dissolving an N-Phenylglycine (PG) monomer in an acidic aqueous solution, and controlling the temperature to be 0-5 ℃;
adding polyethylene glycol (PEG) into the acidic aqueous solution of the PG monomer, and uniformly stirring and mixing to prepare a PG-PEG acidic aqueous solution;
dissolving Ammonium Persulfate (APS) with the molar weight equal to that of the N-Phenylglycine (PG) monomer in an acidic solution, slowly dropwise adding the APS acidic solution into the PG-PEG acidic aqueous solution, keeping an ice bath, and then heating to room temperature for reaction to obtain a dark green solution; dialyzing, and freeze-drying to obtain poly-N-phenylglycine-polyethylene glycol (PPG-PEG) nano-composite powder;
(2) preparation of Poly-N-phenylglycine-polyethylene glycol hydrogel
Respectively preparing the obtained poly-N-phenylglycine-polyethylene glycol (PPG-PEG) nano composite powder and cyclodextrin (alpha-CD) into aqueous solutions with certain concentration according to the inclusion molar ratio of a polyoxyethylene chain segment (EG unit) and the alpha-CD, namely N (CH)2CH2And O, N (alpha-CD) = 1-4: 1, uniformly mixing the two, and standing at room temperature for a period of time to obtain the poly N-phenylglycine-polyethylene glycol hydrogel.
Further, mixing the N-Phenylglycine (PG) monomer and the polyethylene glycol (PEG) in the step (1) at a mass ratio of 1:16 in an acid solution, and stirring for 30-40 minutes to fully and physically mix uniformly;
the APS acidic solution is slowly dripped into the PG-PEG acidic aqueous solution for about 3 hours, kept in an ice bath for 5 hours, and then heated to room temperature to react for 24 hours to obtain a dark green solution.
Further, the acidic aqueous solution in the step (1) is a 0.1M sulfuric acid aqueous solution.
Further, dialyzing for 3 days by adopting a dialysis bag with the molecular weight cutoff of 8000-14000 Da in the dialysis of the step (1), and changing water for three times every day; the resulting solution was freeze-dried using a freeze dryer.
Further, in the step (2), inclusion crosslinking is performed, the polyoxyethylene segment refers to EG unit in the poly-N-phenylglycine-polyethylene glycol nanocomposite, and the mixing ratio, the inclusion molar ratio of EG unit to alpha-CD, i.e. N (CH)2CH2O) n (alpha-CD); the standing room temperature is 5-35 ℃, and the standing time is 1 min-90 h.
The invention relates to a poly-N-phenylglycine-polyethylene glycol hydrogel, which is a binary system hydrogel comprising cyclodextrin (alpha-CD) and a high-molecular photo-thermal material poly-N-phenylglycine-polyethylene glycol nano composite. The poly-N-phenylglycine-polyethylene glycol nano composite comprises non-covalent combination of poly-N-phenylglycine and polyethylene glycol. The ultraviolet absorption peak of the hydrogel is transferred to a near-infrared second window, and irradiation of 1064 nm laser can be carried out, so that the penetration depth of the laser can be increased, and the hydrogel is an injectable multi-response intelligent hydrogel.
Another object of the present invention is to provide poly-N-phenylglycine-polyethylene glycol hydrogels for chemotherapy and photothermal co-therapy.
The poly-N-phenylglycine (PPG) prepared by the invention is of a polyaniline-like structure, can absorb light of a near-infrared second window and shows good temperature rising performance, thereby realizing photothermal therapy. PEG is compounded on poly-N-phenylglycine to improve the water solubility of PPG, and can also perform subject-object self-assembly with alpha-CD to form pseudopolyrotaxane hydrogel. The hydrogel has dual sensitivity of temperature and shear, can generate gel-sol reversible transformation under the change of temperature and shear force, is injectable multi-response intelligent hydrogel, and can load chemotherapeutic drugs to realize the synergistic treatment of chemotherapy and photo-thermal.
The invention has the advantages that: 1) the prepared poly-N-phenylglycine-polyethylene glycol nano composite (PPG-PEG) is cheap in raw material and simple to operate, and only needs a one-step method; 2) the prepared poly N-phenylglycine-polyethylene glycol nano composite has good photo-thermal absorption in a near-infrared second window, and particularly has good photo-thermal conversion efficiency and photo-thermal stability; 3) the double sensitivity of temperature and shearing is realized, and the repeated treatment can be realized; 4) the medicine carrier has photo-thermal induced temperature responsiveness, can be triggered by near infrared light to realize fixed-point on-demand release of medicine load, and has stronger intelligence and controllability.
Detailed Description
The present invention will be further described with reference to the following examples, but the present invention is not limited thereto.
Examples
The preparation method of the hydrogel based on poly N-phenylglycine-polyethylene glycol comprises the following steps:
(1) preparation of Poly-N-phenylglycine-polyethylene glycol nanocomposite (PPG-PEG)
Weighing 1.06 g (7 mmol) of N-Phenylglycine (PG) and dissolving in a round bottom flask containing 50 mL of sulfuric acid aqueous solution (0.1M), adding magnetic stirring, and stirring in an ice-water bath for 10 min;
then weighing 16 g of polyethylene glycol (PEG) and adding into the round-bottom flask of the acidic aqueous solution of the PG monomer, and continuously stirring for 30 min to prepare the PG-PEG acidic aqueous solution;
then weighing 1.60 g (7 mmol) of Ammonium Persulfate (APS) and dissolving in 50 ml of sulfuric acid solution (0.1M), slowly dropwise adding the APS acidic solution into the prepared PG-PEG acidic aqueous solution, dropwise adding for about 3 h, keeping an ice bath for 5 h, then heating to room temperature, stirring and reacting for 24 h to obtain a dark green solution, dialyzing for 3 days by using a dialysis bag with the molecular weight cutoff of 8000-14000 Da, and changing water for three times every day; freeze-drying the obtained solution with a freeze dryer to obtain poly-N-phenylglycine-polyethylene glycol nano composite (PPG-PEG) powder;
(2) preparation of Poly-N-phenylglycine-polyethylene glycol hydrogel
Preparing the poly-N-phenylglycine-polyethylene glycol nano composite (PPG-PEG) powder into a 30 mg/mL aqueous solution, adding a 140 mg/mL aqueous solution of alpha-CD, carrying out equal-volume mixing, carrying out ultrasonic treatment for 5 min, and standing at room temperature of 25 ℃ for 0.5 h to obtain the poly-N-phenylglycine-polyethylene glycol hydrogel formed by the cyclodextrin and the poly-N-phenylglycine-polyethylene glycol nano composite.
Examples of the experiments
The PPG-PEG complex described in example 1 in step (1) was formulated to 30 mg/mL using a 1064 nm laser (0.5W/cm)2) After 5 min of irradiation, the laser source was turned off and naturally cooled to room temperature. In the whole process, the MAG30 thermal infrared imager is adopted to record the temperature change of the lens, and the photo-thermal conversion efficiency of the lens is calculated.
The intelligent hydrogel of poly-N-phenylglycine obtained in the step (2) in example 1 is treated with a 1064 nm laser (0.5W/cm)2) Irradiation, the temperature of the gel was recorded with an infrared thermal imager as a function of time of the light.
Application example 1, the poly-N-phenylglycine-polyethylene glycol hydrogel prepared in example 1 is used for anticancer drug loading application. The implementation method comprises the following steps:
preparing a 30 mg/mL aqueous solution from a poly N-phenylglycine-polyethylene glycol nanocomposite (PPG-PEG), adding a 140 mg/mL alpha-CD aqueous solution containing 100 mu M cisplatin, mixing and stirring uniformly at an equal volume, and standing at room temperature for 0.5 h to obtain the cisplatin drug-loaded poly N-phenylglycine intelligent hydrogel. Experiments prove that the ultraviolet absorption peak of the hydrogel is transferred to a near-infrared second window, and 1064 nm laser can be used for irradiation, so that the penetration depth of the laser can be increased. The hydrogel can realize fixed-point release on demand, and has chemotherapy and photothermal treatment functions.

Claims (4)

1. The preparation method of the hydrogel based on poly N-phenylglycine-polyethylene glycol is characterized by comprising the following steps:
(1) preparation of poly-N-phenylglycine-polyethylene glycol nanocomposite PPG-PEG
Dissolving an N-phenylglycine PG monomer in an acidic aqueous solution, and controlling the temperature to be 0-5 ℃;
adding polyethylene glycol (PEG) into the acidic aqueous solution of the PG monomer, wherein the mass ratio of PG to PEG is 1:16, stirring for 30-40 minutes, and fully and physically mixing uniformly to prepare a PG-PEG acidic aqueous solution;
dissolving ammonium persulfate APS with the molar weight equal to that of the N-phenylglycine monomer in an acidic solution, slowly dropwise adding the APS acidic solution into the PG-PEG acidic aqueous solution for 3 hours, keeping an ice bath for 5 hours, and then heating to room temperature for reaction for 24 hours to obtain a dark green solution; dialyzing, and freeze-drying to obtain poly-N-phenylglycine-polyethylene glycol nano composite PPG-PEG powder;
(2) preparation of Poly-N-phenylglycine-polyethylene glycol hydrogel
Respectively preparing the obtained poly-N-phenylglycine-polyethylene glycol nano composite PPG-PEG powder and cyclodextrin alpha-CD into aqueous solutions with certain concentration according to the inclusion molar ratio of the polyoxyethylene chain section EG unit and the alpha-CD, namely N (CH)2CH2And O and N (alpha-CD) = 1-4: 1, uniformly mixing the two, and standing for 1 min-90 h at the room temperature of 5-35 ℃ to obtain the poly N-phenylglycine-polyethylene glycol hydrogel.
2. The method of claim 1, wherein the poly-N-phenylglycine-polyethylene glycol-based hydrogel is prepared by: the acidic aqueous solution in the step (1) is a 0.1M sulfuric acid aqueous solution.
3. The method of claim 1, wherein the poly-N-phenylglycine-polyethylene glycol-based hydrogel is prepared by: dialyzing for 3 days by adopting a dialysis bag with the molecular weight cutoff of 8000-14000 Da, and changing water for three times every day; the resulting solution was freeze-dried using a freeze dryer.
4. The poly-N-phenylglycine-polyethylene glycol hydrogel prepared by the preparation method according to one of claims 1 to 3, wherein: the ultraviolet absorption peak of the hydrogel is transferred to a near-infrared second window, and the penetration depth of laser is increased by irradiation of 1064 nm laser.
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CN105106954A (en) * 2015-06-30 2015-12-02 广西师范大学 Targeting photothermal therapy water-soluble complex, preparation method and applications thereof
CN105148271A (en) * 2015-07-21 2015-12-16 东华大学 Near-infrared light stimulation controllably responsive photo-thermal microcapsule having thermal therapy/chemotherapy double actions and preparation method of microcapsule
CN105457026A (en) * 2015-12-16 2016-04-06 广西师范大学 Polyaniline-base injectable photo-thermal hydrogel
CN105561307A (en) * 2016-03-23 2016-05-11 广西师范大学 Sulfonated poly N-phenylglycine photo-thermal material as well as preparation method and application thereof

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105106954A (en) * 2015-06-30 2015-12-02 广西师范大学 Targeting photothermal therapy water-soluble complex, preparation method and applications thereof
CN105148271A (en) * 2015-07-21 2015-12-16 东华大学 Near-infrared light stimulation controllably responsive photo-thermal microcapsule having thermal therapy/chemotherapy double actions and preparation method of microcapsule
CN105457026A (en) * 2015-12-16 2016-04-06 广西师范大学 Polyaniline-base injectable photo-thermal hydrogel
CN105561307A (en) * 2016-03-23 2016-05-11 广西师范大学 Sulfonated poly N-phenylglycine photo-thermal material as well as preparation method and application thereof

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