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Preparation and application of glutathione activated photosensitizer

A glutathione and photosensitizer technology, applied in the field of photosensitizer preparation, can solve the problems of strong dependence on oxygen and limit the development of PDT, etc., achieve photosensitivity recovery, excellent endoplasmic reticulum targeting function, and reduce background interference

Pending Publication Date: 2021-06-01
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the vast majority of existing photosensitizers (PSs) are strongly dependent on oxygen, which severely limits the development of PDT

Method used

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  • Preparation and application of glutathione activated photosensitizer
  • Preparation and application of glutathione activated photosensitizer
  • Preparation and application of glutathione activated photosensitizer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment one: synthesis ER A O D. I -DNB

[0024] ER A O D. I (0.325g, 0.50mmol) was dissolved in dichloromethane (10mL), then anhydrous potassium carbonate (0.103g, 0.75mmol) was added, stirred at room temperature for 20min, transferred to an ice-water bath for cooling and stirring for 5min, and then 2,4-Dinitrobenzenesulfonyl chloride (0.20 g, 0.75 mmol) in dichloromethane solution 2 mL was added dropwise under atmosphere protection, the reaction was stirred for 20-30 min in an ice-water bath, and TLC was used to check whether the reaction was complete. After the reaction was completed, the solvent was removed by a vacuum rotary evaporator, and purified by column chromatography to obtain a yellow solid compound ER A O D. I - DNB (0.28 g, 63.6%). 1 H NMR (400MHz, DMSO-d6,) δ (ppm) 9.15 (d, J = 2.3Hz, 1H), 8.72 (dd, J = 8.7, 2.3Hz, 1H), 8.64 (s, 1H), 8.51 (d ,J=8.7Hz,1H),8.29(s,2H),7.68–7.52(m,2H),7.25(s,1H),6.93(s,1H),4.02(s,3H),1.39(s, 9H). 13 C NMR (100...

Embodiment 2

[0025] Embodiment two: synthetic A S D. I -DNB

[0026] A S D. I (250mg, 0.39mmol) was dissolved in dichloromethane (5mL), then Et 3 N 0.78ml, stirred for 10min under ice-water bath conditions, then added dropwise 3mL of a dichloromethane solution of 2,4-dinitrobenzenesulfonyl chloride (125mg, 0.48mmol), the reaction was stirred for 30min under ice-water bath conditions, and then Stir for another 3h. The reaction was checked for completion by TLC. After the reaction was completed, the solvent was removed by a vacuum rotary evaporator, and purified by column chromatography to obtain a red solid compound A S D. I - DNB (231 mg, 68.3%). 1 H NMR (400MHz, CDCl 3 )δ(ppm)8.93(s,1H),8.78(s,1H),8.62(d,J=8.8Hz,1H),8.46(d,J=9.1Hz,1H),8.02(s,2H), 7.72(d, J=8.5Hz, 1H), 7.68–7.53(m, 2H), 7.07(q, J=16.0Hz, 2H), 1.41(s, 9H). 13 C NMR (100MHz, CDCl 3 )δ(ppm)156.00,152.67,152.25,145.06, 141.94,139.32,137.36,133.78,133.65,131.30,131.17,131.03,130.45,129.01,127.19,126.88, 125.26,125.04,...

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Abstract

The invention designs a glutathione activated photosensitizer. An oxo-photosensitizer and a thio-photosensitizer (ERAODI-DNB and ASDI-DNB) are respectively synthesized, and the photosensitizer not only has a good PDT effect under a normal oxygen condition, but also still has an excellent PDT capability under a hypoxic condition. The oxo-photosensitizer has an excellent PDT effect and fluorescence emission, and an excellent endoplasmic reticulum targeting function. Compared with an oxo-photosensitizer, by adding S atoms, the photosensitivity of the thio-photosensitizer is greatly improved. After esterification with 2, 4-dinitrobenzenesulfonyl chloride, the absorption in a visible light region disappears, and the photosensitivity is inhibited. After the photosensitizer is activated by glutathione, the absorption in a visible region is recovered, and the photosensitivity is also recovered. The GSH activated photosensitizer provided by the invention solves the technical problems of hypoxia dependence, low tumor specificity and the like of the existing photosensitizer to a certain extent.

Description

technical field [0001] The invention belongs to the field of photodynamic therapy, and in particular relates to the preparation and application of a novel GSH-activated photosensitizer. Background technique [0002] Photodynamic therapy (PDT) is an effective method for the treatment of cancer by generating cytotoxic reactive oxygen species (ROS), rapidly interacting with biological substances, and causing cell death, vascular damage and other anti-tumor effects. A non-invasive therapy. However, the vast majority of existing photosensitizers (PSs) are strongly dependent on oxygen, which severely limits the development of PDT. In addition to the anti-tumor hypoxic properties, the low tumor selectivity of photosensitizers is also an urgent problem to be solved. To improve reaction selectivity, the development of stimuli-responsive, activatable photosensitizers is one of the most attractive strategies. An activatable photosensitizer that can not only maintain the killing effe...

Claims

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Application Information

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IPC IPC(8): C07D311/58A61K41/00A61P35/00
CPCC07D311/58A61K41/0057A61P35/00
Inventor 李昌华张俊青张永康
Owner NANKAI UNIV
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