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A glutathione-responsive fluorobodipyrrole anticancer photosensitizer and its preparation and application

A technology of fluoroboridipyrrole and fluoroboridipyrrole, which is applied in the field of fluoroboridipyrrole anticancer photosensitizers, can solve the problems of not being able to meet the specific identification of tumor tissues, and achieve skin phototoxicity, less side effects, and structure single effect

Inactive Publication Date: 2021-08-31
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Compared with the first-generation photosensitizers, the second-generation photosensitizers have improved therapeutic effects, but they still cannot meet the specific recognition of ideal photosensitizers only on tumor tissues, so functional photosensitizers came into being

Method used

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  • A glutathione-responsive fluorobodipyrrole anticancer photosensitizer and its preparation and application
  • A glutathione-responsive fluorobodipyrrole anticancer photosensitizer and its preparation and application
  • A glutathione-responsive fluorobodipyrrole anticancer photosensitizer and its preparation and application

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Experimental program
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Effect test

Embodiment 1

[0040] (1) Dissolve the compound with 100mL ethanol (0.20g, 0.53mmol) was dissolved in a 250mL round bottom flask, and elemental iodine (0.34g, 1.33mmol) and iodic acid (0.18g, 1.06mmol) were added to the reaction flask in turn. The resulting mixture was warmed up to 60°C and reacted for 2 hours under nitrogen protection. After the reaction was completed, the ethanol was removed by rotary evaporation under reduced pressure, the residue was mixed with 50 mL of water, extracted three times with dichloromethane (50 mL×3), the organic layers were combined, and dried with anhydrous magnesium sulfate, and the volume ratio was 1:1 with petroleum ether - dichloromethane as the eluent, purified by silica gel column chromatography to obtain a red solid compound (0.31 g, 94%). 1 H NMR (400MHz, CDCl 3 ):δ=7.17(d,J=8.4Hz,2H,ArH),7.12(d,J=8.4Hz,2H,ArH),4.78(d,J=2.4Hz,2H,OCH 2 ),2.64(s,6H,CH 3 ), 2.57(t, J=2.4Hz, 1H, C≡CH), 1.44(s, 6H, CH 3 ).

[0041] (2) Accurately weigh the compo...

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Abstract

The invention discloses a glutathione-responsive fluoroborodipyrrole anticancer photosensitizer and its preparation. The present invention firstly prepares iodofluoroboron dipyrrole derivatives and p-dimethylaminophenyl substituted fluoroboron dipyrrole derivatives; the former has high singlet oxygen quantum yield due to the introduction of heavy atom iodine, and can be used as photosensitizers; The latter is an ideal quencher because of its redder absorption and weaker fluorescence emission due to the introduction of p-dimethylaminophenyl; linked together to obtain a glutathione-responsive anticancer photosensitizer. The photosensitizer can be used for targeted photodynamic therapy guided by fluorescence imaging. The compound has a simple synthesis method, readily available raw materials, low cost, few side reactions, high yield, easy purification, and is favorable for industrial production.

Description

technical field [0001] The invention belongs to the field of design and synthesis of antineoplastic drugs, and in particular relates to a glutathione-responsive fluorobodipyrrole anticancer photosensitizer and its preparation and application. Background technique [0002] Cancer has become one of the major diseases that seriously affect human health and threaten human life, and the incidence of cancer is on the rise. Therefore, conquering cancer has become the top priority of governments and the World Health Organization all over the world. Photodynamic therapy (Photodynamic Therapy, referred to as PDT) is a new method for the treatment of premalignant and malignant lesions by photoactivating photosensitizers and reacting with tissue oxygen to generate reactive oxygen species. Due to its unique advantages, it has attracted extensive attention from scientific researchers. As the core element in the process of photodynamic therapy, photosensitizers can be enriched in a large...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02A61K41/00A61P35/00
CPCA61K41/0057A61P35/00C07F5/022
Inventor 刘见永李小强操晶晶杨德潮张明山许敢
Owner FUZHOU UNIV
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