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A class of singlet oxygen-type photosensitizer materials with aggregation-induced luminescence properties and their preparation methods and applications

A technology of aggregation-induced luminescence and singlet oxygen, which is applied in the field of biomedical materials, can solve problems such as unfavorable fluorescence-mediated photodynamic therapy, and achieve the effects of high-efficiency cure, high-specific targeting, and good lethality

Active Publication Date: 2022-05-24
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the photosensitizer materials used in the previous reports are photosensitizer molecules that aggregate to cause quenching. Once the aggregation of fluorescence is immediately quenched, it is not conducive to fluorescence-mediated photodynamic therapy (Qiao, B.; Luo, Y.; Cheng, H.-B.; Ren, J.; Cao, J.; Yang, C.; Liang, B.; Yang, A.; Yuan, X.; Li, J.; Deng, L.; Li, P. ; Ran, H.-T.; Hao, L.; Zhou, Z.; Li, M.; Zhang, Y.; Timashev, P.S.; Performance for Multimodal Imaging-Guided Tumor-Specific Therapy. ACS Nano2020, 14(10), 12652–12667. https: / / doi.org / 10.1021 / acsnano.0c00771.)

Method used

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  • A class of singlet oxygen-type photosensitizer materials with aggregation-induced luminescence properties and their preparation methods and applications
  • A class of singlet oxygen-type photosensitizer materials with aggregation-induced luminescence properties and their preparation methods and applications
  • A class of singlet oxygen-type photosensitizer materials with aggregation-induced luminescence properties and their preparation methods and applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Example 1 Preparation of a singlet oxygen-type photosensitizer material with aggregation-induced luminescence properties (singlet oxygen photosensitizer, marked as PTI in Example 1)

[0057]

[0058] The synthetic route is as follows:

[0059]

[0060] a) Synthesis of compound 10-phenyl-10H-phenothiazine (1): add phenothiazine (6g, 30mmol), copper powder (1.9g, 30mmol), potassium carbonate (8.3g, 60mmol) to a 100ml two-necked flask ) and 18-crown ether-6 (3g, 60mmol), nitrogen-pumping-nitrogen cycle 3 times (10 minutes each time), then add iodobenzene 3.93ml and ultra-dry N,N-dimethylformamide 60mL , heated to 180°C for 12 hours, the reaction was over, extracted with dichloromethane / water, dried over anhydrous magnesium sulfate for 2 hours, separated and purified by column layer analysis to obtain colorless crystals (4.2g) with a yield of 60%. 1 H NMR (500MHz, CDCl 3 ), 7.60(t, 2H), 7.46(t, 1H), 7.38(d, 2H), 7.01(d, 2H), 6.82(m, 4H), 6.20(d, 2H).

[0061] b) Sy...

Embodiment 2

[0064] Example 2 Preparation of a singlet oxygen-type photosensitizer material with aggregation-induced luminescence properties (singlet oxygen photosensitizer, marked as PI in Example 2)

[0065]

[0066] The synthetic route is as follows:

[0067]

[0068] a) The synthesis procedure of the intermediate 10-phenyl-10H-phenothiazine (1) is the same as that of Example 1.

[0069] b) Synthesis of compound 10-phenyl-10H-phenothiazine-3-aldehyde (2): add ultra-dry N,N-dimethylformamide solvent ( 2.8 mL) and 1,2-dichloroethane (5 mL), and after stirring for ten minutes, phosphorus oxychloride (2.1 mL) was added dropwise to the mixture. Then, 10-phenyl-10H-phenothiazine (1 g, 3.6 mmol) dissolved in 5 mL of 1,2-dichloroethane solution was added dropwise within 30 min, heated to 90° C., and the reaction was continued for 12 h. After stopping the reaction and cooling to room temperature, the mixture was poured into 100 mL of ice-water and washed with saturated NaHCO 3 The solut...

Embodiment 3

[0071] Example 3 Based on the specific targeting of phenothiazine photosensitizers (PI and PTI) to lipid droplets After culturing MCF-7 cells for 24 hours, the cells were first incubated with oleic acid for 1 hour, followed by the addition of 10 μM PI and PTI, respectively The cells were incubated for 6 h, then the original medium was removed and washed twice with PBS, and fresh medium containing the lipid droplet dye Bodipy (final concentration 2 μM) was added to continue incubation for 20-30 min, washed and replaced with fresh medium for confocal microscopy imaging characterization. Figure 1a and Figure 1b After incubation with cells for 6 hours for the PTI prepared in Example 1 and the PI prepared in Example 2, respectively, the lipid droplet dyeing effect of the cells was performed with the lipid droplet dye BODIPY. Figure 1c and Figure 1d Co-staining index intensity map of lipid droplet co-staining with lipid droplet dye BODIPY after incubation with cells for PTI prep...

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Abstract

The invention discloses a singlet oxygen type photosensitizer material with aggregation-induced luminescence performance, a preparation method and application thereof. The method comprises: using phenothiazine and iodobenzene derivatives as raw materials, obtaining 10-phenylphenothiazine through Ullman coupling reaction, and brominating the 10-phenylphenothiazine with N-bromosuccinimide , carry out Suzuki coupling reaction with 5-formyl-2-thiophene boronic acid to obtain an aldehyde-containing compound, and perform Knoevenagel condensation on the aldehyde-containing compound and 1,3-indanedione to obtain a singlet oxygen type photosensitizer material. This material is a new material of photosensitizer with AIE performance. The drug prepared by this material can overcome the problem of poor tumor treatment effect caused by the fluorescence aggregation quenching effect and the decrease of ROS production caused by aggregation. Secondly, the cancer cell membrane is used to coat the photosensitizer The method endows photosensitizers with the ability to homologously target tumors, and has application prospects for non-invasive and precise clinical PDT treatment.

Description

technical field [0001] The invention belongs to the field of biomedical materials, in particular to a class of singlet oxygen-type photosensitizer materials with aggregation-induced luminescence properties and a preparation method and application thereof. Background technique [0002] Photodynamic therapy (PDT) has multiple advantages such as non-invasiveness, high spatiotemporal accuracy and controllability, minimal drug resistance, low biological toxicity, etc., and has become an effective and rapidly developing cancer treatment modality. Under light irradiation, photosensitizers transfer electrons or energy to surrounding molecular oxygen through photochemical interactions to generate highly phototoxic reactive oxygen species (ROS), which can kill tumor cells and activate anti-cancer genes. However, photosensitizers that are essential in photodynamic therapy have limited their widespread application due to short blood circulation lifetime, poor tumor targeting ability, lo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/04C07D279/22C09K11/06B82Y40/00B82Y5/00A61P35/00A61K47/46A61K41/00
CPCC07D417/04C07D279/22C09K11/06A61K41/0057A61K47/46A61P35/00B82Y5/00B82Y40/00C09K2211/1037C09K2211/1092C09K2211/1011
Inventor 唐本忠王志明李银张荣远万清
Owner SOUTH CHINA UNIV OF TECH
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