Diiodostyrene type boron fluoride dipyrrole-hyaluronic acid and its preparation method and application

A technology for substituting boron dipyrrole fluoride and boron dipyrrole fluoride, applied in the field of biomaterials, can solve problems such as large side effects, inability to distinguish normal cells from tumor cells, and poor active targeting

Inactive Publication Date: 2017-04-12
NANJING TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the main problems of photosensitizers currently commercialized and clinically tested are: 1) the inherent hydrophobicity of photosensitizers leads to their aggregation in buffer solutions or blood circulation, which quenches reactive oxygen species; 2) poor active targeting, Unable to distinguish between normal cells and tumor cells, poor selectivity and large side effects during photodynamic therapy; 3) In clinical and practical applications, it is necessary to avoid light after administration to reduce the side effects of photosensitizers on normal organs of the human body

Method used

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  • Diiodostyrene type boron fluoride dipyrrole-hyaluronic acid and its preparation method and application
  • Diiodostyrene type boron fluoride dipyrrole-hyaluronic acid and its preparation method and application
  • Diiodostyrene type boron fluoride dipyrrole-hyaluronic acid and its preparation method and application

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Experimental program
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Effect test

Embodiment 1

[0054] (1) Synthesis of 4-(3-hydroxyl-1-propoxy)-1-benzaldehyde

[0055] p-Hydroxybenzaldehyde (0.1mol, 12.2g), 3-bromo-1-propanol (0.11mol, 15.2g) and potassium carbonate (0.3mol, 40g) were added to acetone (200ml). Stir continuously at 60°C until the p-hydroxybenzaldehyde is completely reacted and the reaction is stopped, and the reaction time is 12 hours. The reaction mixture was suction filtered to obtain the filtrate, which was spin-dried and washed with petroleum ether: ethyl acetate = 1:2 as the eluent through silica gel chromatography to obtain the yellow liquid compound 14-(3-hydroxy-1-propoxy) - 1-Benzaldehyde (10.32g), the yield is about 68%. 1 HNMR (400Hz, CD 3 OD)δ9.75(s,1H),7.73-7.70(m,2H),6.93-6.89(m,2H),4.13-4.09(m,2H),3.80-3.76(m,2H),2.01-1.97 (m,2H); ESI-MS: 166.45[M + ].

[0056] (2) Synthesis of boron fluoride dipyrrole

[0057] Benzoyl chloride (1 g, 7.86 mmol) and 2,4-dimethylpyrrole (2.0 mL, 19.65 mmol) were dissolved in dichloromethane (100 mL) un...

Embodiment 2

[0067] Diiodostyrene-type boron fluoride dipyrrole-hyaluronic acid nanoparticles and hyaluronic acid were dissolved in D 2 O, and then carry out the proton nuclear magnetic spectrum test to determine the change of the hydrogen chemical shift after the diiodostyrene boron fluoride dipyrrole is attached to the hyaluronic acid. Such as figure 1 As shown, by comparing the NMR spectra of diiodostyrene-type boron fluoride dipyrrole-hyaluronic acid nanoparticles and hyaluronic acid, it can be seen that the chemical shift is between 7 and 8, and the diiodostyrene-type fluoride The boron dipyrrole-hyaluronic acid nanoparticles have a peak, but the pure hyaluronic acid does not. This is due to the chemical shift of the benzene ring after the introduction of the diiodostyrene-type boron dipyrrole on the hyaluronic acid. It can be determined that the two Iodostyrene-type boron fluoride dipyrrole was successfully attached to hyaluronic acid.

Embodiment 3

[0069] The ultraviolet-visible absorption spectrum and fluorescence emission spectrum of diiodostyrene boron fluoride dipyrrole-hyaluronic acid nanoparticles were tested by Shimadzu UV-3150 ultraviolet-visible spectrometer and RF-530XPC fluorescence spectrometer. figure 2 For its ultraviolet-visible absorption spectrum, diiodostyrene-type boron fluoride dipyrrole-hyaluronic acid nanoparticles have absorption at 600nm, but pure hyaluronic acid does not, which is diiodostyrene-type boron fluoride UV-Vis absorption of diiodostyrene boron fluoride dipyrrole attached to hyaluronic acid;

[0070] image 3 It is the fluorescence emission spectrum of diiodostyrene-type boron fluoride dipyrrole-hyaluronic acid nanoparticles in PBS solution, PBS and DMSO mixed solution (volume ratio, 1:1), comparing the two, it can be found that D2 The fluorescence emission of iodostyrene-type boron fluoride dipyrrole-hyaluronic acid nanoparticles in PBS solution is very weak, which is due to the fluo...

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Abstract

The invention discloses diiodostyrene type boron fluoride dipyrrole-hyaluronic acid as well as a preparation method and an application thereof. A hydrophobic photosensitizer diiodostyrene type boron fluoride dipyrrole with poor biocompatibility and poor targeting performance is connected onto hyaluronic acid to obtain an amphipathic molecule which is self-assembled to obtain a nano particle of the diiodostyrene type boron fluoride dipyrrole-hyaluronic acid; in addition to good water solubility, biocompatibility and CD44 special targeting performance, the nano particle further has the following advantages that firstly, passive targeting performance is realized, the accuracy of introducing the photosensitizer to a tumor part is improved, and tumor photodynamic therapy is realized; secondly, the intelligent monitoring for judging whether the photosensitizer nano particle accurately reaches the tumor part is realized; thirdly, after the nano particle enters the cells, the nano particle is self-assembled and dissociated, reactive oxygen species are recovered under illumination, the generation of the reactive oxygen species is intelligently controlled, and the defect that dosage for clinical tumor photodynamic therapy needs to keep in a dark place is solved.

Description

technical field [0001] The invention belongs to the field of biological materials, and specifically relates to a novel CD44-specific targeting photosensitizer diiodostyrene type boron fluoride dipyrrole-hyaluronic acid, its synthesis and its application in intelligent photodynamic anti-tumor therapy. Background technique [0002] Cancer, also known as malignant tumor, is one of the major diseases that threaten human health and life. Among various diseases, the mortality rate of malignant tumors ranks second, second only to cardiovascular and cerebrovascular diseases. With the continuous development of medical technology, the treatment methods based on surgery, radiotherapy and chemotherapy have made great progress. However, due to the complicated pathogenesis of malignant tumors and the difficulty of treatment, it has always been a challenge to find drugs and methods for treating malignant tumors with high efficiency and low toxicity. Difficulties and hotspots in today's th...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K47/61A61K9/14A61K41/00A61P35/00
Inventor 董晓臣张琪史华夏顾桂英刘长兵黄维
Owner NANJING TECH UNIV
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