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Hydrophilic chlorin photo-sensitive and sono-sensitive agent with long wavelength and preparation method and application thereof

A chlorin and long-wavelength technology, applied in the field of chemical medicine, can solve the problems of slow clearance rate, low selectivity of tumor cells, and narrow therapeutic window

Active Publication Date: 2015-12-02
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, light and sound sensitizers still have disadvantages such as low selectivity to tumor cells, short maximum irradiation wavelength, narrow therapeutic window, poor solubility under physiological conditions, and slow clearance rate in vivo.

Method used

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  • Hydrophilic chlorin photo-sensitive and sono-sensitive agent with long wavelength and preparation method and application thereof
  • Hydrophilic chlorin photo-sensitive and sono-sensitive agent with long wavelength and preparation method and application thereof
  • Hydrophilic chlorin photo-sensitive and sono-sensitive agent with long wavelength and preparation method and application thereof

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Embodiment 1

[0034]

[0035] Synthesis of compound 8a-TEL

[0036](1) Dissolve 53.2 mg of commercially available compound 1 in 10 mL of methanol, add 200 μL of concentrated sulfuric acid dropwise, stir at a temperature of 0-50 ° C, protect with nitrogen balloon, monitor by TLC, stop the reaction after 4 hours, add 20 mL of deionized water to the reaction solution , and transferred to a 125mL separatory funnel, extracted with dichloromethane (30ml×3), combined the dichloromethane layers, added anhydrous sodium sulfate to dry, suction filtered, and concentrated to obtain a crude product. The crude product was purified by silica gel column chromatography (petroleum ether: ethyl acetate = 1:4) to obtain 44.2 mg of a dark green solid, namely chlorin 15,17-dimethyl ester, with a yield of 77%. ESI-MSm / z:625.4[M+H] + . 1 HNMR (400MHz, CDCl 3 )δ9.64(1H,s),9.50(1H,s),8.72(1H,s),8.01(1H,dd,J=17.8,11.5Hz),6.32(1H,dd,J=17.8,1.2Hz ),6.12(1H,dd,J=11.5,1.2Hz),5.51(1H,d,J=18.7Hz),5.26(1H,d,J=18.7Hz)...

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Abstract

The invention relates to a hydrophilic chlorin photo-sensitive and sono-sensitive agent with long wavelength and a preparation method and an application thereof, and belongs to the field of chemical medicine. The compound is represented as the following formula described in the description. The compound of hydrophilic chlorin photo-sensitive and sono-sensitive agent with long wavelength has inhibition effects in different degrees on human liver cancer cell Hep G2 in anticancer activity evaluation in vitro. The ratio of photoactivity to dark activity and the ratio of sono-activity to dark activity are much higher than that of hemoporphyrinmonomethyl ether as a positive contrast. The hydrophilic chlorin photo-sensitive and sono-sensitive agent with long wavelength has advantages of low toxicity, high efficiency, treatment wavelength moving towards long wave region and the like. The compound in the invention can be used as an excellent photosensitizer and an excellent sonosensitizer for photodynamic and sonodynamic therapy of tumors.

Description

technical field [0001] The invention relates to a kind of hydrophilic long-wavelength chlorin-based light and sound sensitizer and its preparation method and application, belonging to the field of chemical medicine. Background technique [0002] Photodynamic therapy (PDT) and sonodynamic therapy (SDT) use a photosensitizer or a photosensitizer to kill tumor cells through a chemical reaction under light or ultrasound excitation, respectively. purpose of a medical technology. Among them, photodynamic therapy (Photodynamic therapy, PDT) is the use of photosensitizers and visible light in the presence of oxygen, through the reaction of singlet oxygen ( 1 o 2 ) and free radicals have great lethality to tumor cells. Compared with traditional treatment methods such as surgery, chemotherapy, and radiotherapy, PDT has the advantages of high selectivity to target tissues, less side effects, and no damage to internal organs; Sonodynamic therapy (SDT) is used in Photodynamic therapy...

Claims

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Application Information

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IPC IPC(8): C07D487/22A61K31/409A61P35/00
CPCC07D487/22
Inventor 郭修晗赵伟杰曹雷王柳王世盛李悦青
Owner DALIAN UNIV OF TECH
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