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ALA-HPO hybrid derivative with iron chelating property and PDT activity, preparation method and application thereof

An ALA-HPO, derivative technology, applied in the direction of organic active ingredients, medical preparations with non-active ingredients, medical preparations containing active ingredients, etc., can solve the problems of loss of toxicity, adverse effects of PpIX, and long distribution duration.

Active Publication Date: 2020-12-11
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Therefore, iron chelation strategies in modern anticancer chemotherapy have attracted great interest, but iron in cells is always chelated by various molecules, but this does not make it less toxic because chelated iron is still able to Generate active oxygen
After deferoxamine is used as a heme synthesis inhibitor, it is found that it has certain selectivity and can increase the accumulation of PpIX, but its pharmacokinetic performance is poor, which makes its distribution last longer. Secondly, due to deferoxamine With strong antioxidant activity under this condition, higher DFO concentrations may adversely affect the formation of PpIX

Method used

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  • ALA-HPO hybrid derivative with iron chelating property and PDT activity, preparation method and application thereof
  • ALA-HPO hybrid derivative with iron chelating property and PDT activity, preparation method and application thereof
  • ALA-HPO hybrid derivative with iron chelating property and PDT activity, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0075]

[0076] ALA hydrochloride (5.00 g, 29.8 mmol), NaHCO 3 (15.04g, 179mmol) and Boc 2 O (6.51g, 29.8mmol), and 40mL of anhydrous methanol was added as a solvent, stirred at room temperature, and the reaction progress was detected by TLC during the reaction. After 12 hours, the reaction was stopped. At this time, the reaction solution was pale yellow. The solid was removed by filtration, and the solvent was distilled off under reduced pressure. The residual solid was dissolved in water, acidified with 10% potassium bisulfate solution to pH = 2, and extracted with ethyl acetate. , the organic layer was washed several times with saturated brine (15 mL×3), dried over anhydrous sodium sulfate, filtered, and the organic solvent was distilled off under reduced pressure to obtain N-Boc-ALA (6.24 g, 90%) as a white solid.

[0077] Add kojic acid (4.10g, 50mmol), potassium carbonate (8.28g, 60mmol) and 100mL of ethanol and water (1:1) into a 250mL round bottom flask respectivel...

Embodiment 2

[0085]

[0086] ALA hydrochloride (5.00 g, 29.8 mmol), NaHCO 3 (15.04g, 179mmol) and Boc 2 O (6.51g, 29.8mmol), and 40mL of anhydrous methanol was added as a solvent, stirred at room temperature, and the reaction progress was detected by TLC during the reaction. After 12 hours, the reaction was stopped. At this time, the reaction solution was pale yellow. The solid was removed by filtration, and the solvent was distilled off under reduced pressure. The residual solid was dissolved in water, acidified with 10% potassium bisulfate solution to pH = 2, and extracted with ethyl acetate. , the organic layer was washed several times with saturated brine (15 mL×3), dried over anhydrous sodium sulfate, filtered, and the organic solvent was distilled off under reduced pressure to obtain N-Boc-ALA (6.24 g, 90%) as a white solid.

[0087] Add kojic acid (4.10g, 50mmol), potassium carbonate (8.28g, 60mmol) and 100mL of ethanol and water (1:1) into a 250mL round bottom flask respectivel...

Embodiment 3

[0095]

[0096] ALA hydrochloride (5.00 g, 29.8 mmol), NaHCO 3 (15.04g, 179mmol) and Boc 2 O (6.51g, 29.8mmol), and 40mL of anhydrous methanol was added as a solvent, stirred at room temperature, and the reaction progress was detected by TLC during the reaction. After 12 hours, the reaction was stopped. At this time, the reaction solution was pale yellow. The solid was removed by filtration, and the solvent was distilled off under reduced pressure. The residual solid was dissolved in water, acidified with 10% potassium bisulfate solution to pH = 2, and extracted with ethyl acetate. , the organic layer was washed several times with saturated brine (15 mL×3), dried over anhydrous sodium sulfate, filtered, and the organic solvent was distilled off under reduced pressure to obtain N-Boc-ALA (6.24 g, 90%) as a white solid.

[0097] Add kojic acid (4.10g, 50mmol), potassium carbonate (8.28g, 60mmol) and 100mL of ethanol and water (1:1) into a 250mL round bottom flask respectivel...

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Abstract

The invention provides an ALA-HPO hybrid derivative shown as a formula (I) or a formula (II), and a preparation method thereof, and application of the ALA-HPO hybrid derivative in preparation of photodynamic therapy drugs. The formula (I) and the formula (II) are defined in the specification.

Description

technical field [0001] The invention relates to a derivative coupled with hydroxypyridone (HPO) and 5-aminolevulinic acid (ALA) with iron ion chelating ability, a preparation method and photodynamic application thereof. Background technique [0002] Traditional tumor treatment methods mainly include surgery, chemotherapy and radiotherapy, etc., but there are some serious defects in these treatment methods. In recent years, with the development of medical technology, photodynamic therapy (PDT) has gradually entered people's field of vision. PDT is the use of visible light to activate exogenously administered or endogenously formed photosensitive substances in the presence of molecular oxygen. , a photosensitizer after light activation, whose photosensitization leads to the formation of singlet oxygen, a strong oxidant that can lead to damage to a variety of subcellular substrates and cell death. Through the study of its mechanism of action, it is found that photosensitizer i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/69A61K31/4412A61K41/00A61K47/54A61K47/55A61P35/00
CPCC07D213/69A61K41/0061A61K47/545A61K47/55A61K31/4412A61P35/00A61K2300/00Y02P20/55
Inventor 谢媛媛林玉燕袁圣利张雨佳
Owner ZHEJIANG UNIV OF TECH
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