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Preparation and application of a photosensitizer activated by alkaline phosphatase

A technology of phosphatase and photosensitizer, applied in the field of photosensitizer preparation, can solve the problems of low selectivity, prolonged skin photosensitization, side effects, etc., and achieve the effect of improving photodynamic ability, reducing pKa, and avoiding self-absorption

Active Publication Date: 2022-04-01
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the low selectivity of existing photosensitizers, treatment-related toxicity and side effects on adjacent normal tissues and prolonged skin photosensitization

Method used

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  • Preparation and application of a photosensitizer activated by alkaline phosphatase
  • Preparation and application of a photosensitizer activated by alkaline phosphatase
  • Preparation and application of a photosensitizer activated by alkaline phosphatase

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Embodiment one: synthesis ALP PS-Et

[0025] P.S. Se-I (0.5g, 0.80mmol) was dissolved in acetonitrile (20mL), diethyl chlorophosphate (0.21g, 1.22mmol) and triethylamine (0.12g, 1.2mmol) were added dropwise, and the reaction was stirred at room temperature for 5min Afterwards, DMAP (9.8 mg, 0.08 mmol) was added and stirring was continued overnight at room temperature. After the reaction, the solvent was removed by rotary evaporation, and purified by column chromatography using dichloromethane and methanol as eluents to obtain a bright red solid compound ALP PS-Et (0.2 g, 32.8%). 1 H NMR (400MHz, CDCl 3 )δ (ppm) 8.76-8.67 (m, 1H), 7.99 (s, 2H), 7.78-7.68 (m, 2H), 7.61-7.51 (m, 2H), 7.11 (d, J = 15.6Hz, 1H) , 6.88(d, J=16.0Hz, 1H), 4.43-4.27(m, 4H), 1.42(t, J=7.2Hz, 6H). 13 C NMR (100MHz, CDCl 3 )δ(ppm)158.51,152.63,147.51,139.23,135.27,133.40,133.29,131.90,129.65,129.45,129.29,128.38,126.82,124.77,116.23,115.03,89.52,65.45,65.39,16.18,16.11.

Embodiment 2

[0026] Embodiment two: synthesis ALP P.S.

[0027] ALP PS-Et (0.2g, 0.26mmol) was dissolved in dichloromethane (10mL), trimethylbromosilane (1mL) was slowly added dropwise under nitrogen protection, and reacted at room temperature for 8h. Filtration, dichloromethane (50mL) rinse filter residue, dry in a vacuum oven to obtain a red solid compound ALP PS (77.8 mg, 42.3%). 1 H NMR (400MHz, DMSO-d 6 ) δ (ppm) 8.60 (d, J = 8.0Hz, 1H), 8.29 (s, 2H), 8.11 (d, J = 7.2Hz, 1H), 7.86 (d, J = 16.4Hz, 1H), 7.83 ( s, 1H), 7.69 (m, 2H), 7.21 (d, J=16.0Hz, 1H). 13 C NMR (100MHz, DMSO-d 6 )δ (ppm) 158.98, 150.55, 139.28, 134.74, 134.19, 132.64, 130.60, 129.63, 128.63, 126.31, 124.22, 117.44, 115.91, 92.31, 71.98. HRMS (ESI): m / z [M+NH + ]calcd for C 20 h 11 I 2 N 3 OSe + 725.8049; found 725.8030.

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Abstract

The invention relates to a preparation method and application of a photosensitizer activated by alkaline phosphatase. By blocking the ICT effect, the photosensitizer has no absorption in the visible light region to completely inhibit the photosensitivity. After the specific recognition of alkaline phosphatase, the ICT effect is restored, and the photosensitivity is completely released along with the recovery of the visible light region absorption. This strategy is beneficial to the enrichment of photosensitizers in alkaline phosphatase-overexpressed tumor cells and improves the effect of photodynamic therapy.

Description

technical field [0001] The invention relates to the field of photodynamic therapy, in particular to the preparation and application of an alkaline phosphatase-activated photosensitizer. Background technique [0002] Photodynamic therapy (PDT) is an emerging treatment modality for a variety of cancers. Under light conditions, the photosensitizer is excited to convert triplet oxygen ( 3 o 2 ) into cytotoxic singlet oxygen ( 1 o 2 ), leading to irreversible damage to diseased cells and tissues. However, the low selectivity of existing photosensitizers leads to treatment-related toxicity and side effects on adjacent normal tissues as well as prolonged skin photosensitization. In order to overcome the defects, functional photosensitizers have emerged, which are insensitive in non-cancerous tissues, are activated by interacting with specific biosignaling molecules overexpressed by tumor cells, and efficiently produce 1 o 2 , thereby killing tumor cells. Contents of the in...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K41/00C07F9/547A61P35/00
CPCA61K41/0057C07F9/547A61P35/00
Inventor 李昌华翟文豪刘明
Owner NANKAI UNIV
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