Near-infrared nano-photosensitizer, and preparation method and use thereof
The present invention relates to the technical field of photosensitizers, and particularly to a near-infrared nano-photosensitizer and a preparation method and use thereof. The near-infrared nano-photosensitizer in the present invention is modified by conjugation extension of the boron dipyrromethene core, achieving absorption and emission spectra close to the near-infrared region. A polyfluoroalkyl group and a polyethylene glycol group are introduced to the boron dipyrromethene structure to obtain an amphiphilic photosensitizer. By means of the strong fluorine-fluorine interaction between the polyfluoroalkyl group and the hydrophilic interaction of the polyethylene glycol group, a nano-photosensitive micelle with an ultra-low CMC value is ultimately constructed. Boron dipyrromethene is induced by fluorine-fluorine interaction to undergo J-aggregation, causing the maximum absorption peak to red-shift to the near-infrared region, beneficial to the deep phototherapy of tumors.
1. A near-infrared nano-photosensitizer, having a structure of Formula (I):
wherein R is
x+y=11, x and y are both a positive integer;
R 1 is
n=11-221, and n is a positive integer.
2. The near-infrared nano-photosensitizer according to claim 1 , wherein y is 3, 5 or 7.
3. A method for preparing a near-infrared nano-photosensitizer according to claim 1 , comprising steps of:
(1) reacting a compound of Formula (II) with
in the presence of acetic acid and piperidine in a solvent, to obtain a compound of Formula (III); and
(2) reacting the compound of Formula (III) obtained in Step (1) with azido functionalized polyethylene glycol in the presence of copper sulfate pentahydrate and sodium ascorbate in a solvent, to obtain a compound of Formula (I),
wherein the structures of Formulas (I), (II) and (III) are shown below:
wherein R is
x+y=11, x and y are both a positive integer;
R 1 is
n=11-227, and n is a positive integer.
4. The method for preparing a near-infrared nano-photosensitizer according to claim 3 , wherein the solvent is selected from the group consisting of acetonitrile, toluene, benzene, N,N-dimethylformamide, dimethyl sulfoxide and any combination thereof.
5. The method for preparing a near-infrared nano-photosensitizer according to claim 3 , wherein in Step (1), the molar ratio of the compound of Formula (II),
piperidine and acetic acid is 1:3-6:10-20:10-20.
6. The method for preparing a near-infrared nano-photosensitizer according to claim 3 , wherein in Step (1), the reaction temperature is 80-120° C.; and the reaction time is 12-48 h.
7. The method for preparing a near-infrared nano-photosensitizer according to claim 3 , wherein in Step (2), the molar ratio of the compound of Formula (III), azido functionalized polyethylene glycol, copper sulfate pentahydrate, and sodium ascorbate is 1:1-3:0.1-0.2:0.1-0.2.
8. The method for preparing a near-infrared nano-photosensitizer according to claim 3 , wherein in Step (2), the reaction temperature is 40-60° C.; and the reaction time is 12-24 h.
9. A nanomicelle solution comprising a near-infrared nano-photosensitizer according to claim 1 in water.
10. An anti-tumor composition comprising a near-infrared nano-photosensitizer according to claim 1 in the preparation of drugs for the treatment of tumors.