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Conjugate of 5-aminolevulinic acid and 3-hydroxypyridin-4-one and its preparation method and use

A technology of aminolevulinic acid and hydroxypyridine, applied in 5-aminolevulinic acid-iron chelator conjugate and preparation thereof, in the field of photodynamic therapy drugs, can solve the problem of poor stability, affecting storage period, poor activity, etc. question

Active Publication Date: 2019-05-21
ZHEJIANG GONGSHANG UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The activity of ALA-HPO conjugate 1 is generally poor. Although 2f, 2i and 2j in the ALA-HPO conjugate have good activity, ALA is connected to 3-hydroxypyridin-4-one through an ester bond, and the amide Relatively less stable than bonds, which may affect their shelf life

Method used

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  • Conjugate of 5-aminolevulinic acid and 3-hydroxypyridin-4-one and its preparation method and use
  • Conjugate of 5-aminolevulinic acid and 3-hydroxypyridin-4-one and its preparation method and use
  • Conjugate of 5-aminolevulinic acid and 3-hydroxypyridin-4-one and its preparation method and use

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Experimental program
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Embodiment 1

[0042] Embodiment 1, the preparation method of compound 1, carry out the following steps successively:

[0043] A, the synthesis of carboxyl-containing compound 4

[0044] The synthesis of compound 4a, carries out the following steps successively:

[0045] ①, 3-benzyloxy-1-methyl-4-oxo-1,4-dihydropyridine-2-carboxylic acid (2a) (1.3g, 5mmol), L-phenylalanine ethyl ester hydrochloride Salt (1.08g, 5mmol) and 6-chlorobenzotriazole-1,1,3,3-tetramethyluronium hexafluorophosphate (2.28g, 5.5mmol) were dissolved in DMF (30ml) as solvent , then added triethylamine (1.52g, 15mmol), and stirred at room temperature for 12h (overnight); the residue obtained after evaporating the solvent was dissolved in 50ml of dichloromethane, and the mass concentration was 5% sodium bicarbonate aqueous solution and saturated salt successively. Wash with water, dry over anhydrous sodium sulfate, distill off dichloromethane and purify the residue obtained by silica gel column chromatography (methanol: ...

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Abstract

The invention discloses a conjugate of 5-aminolevulinic acid and 3-pyridone-4-ketone. The conjugate is a conjugate of the 5-aminolevulinic acid and the 3-pyridone-4-ketone as an iron chelating agent, and is an ALA-HPO conjugate; the structural formula of the ALA-HPO conjugate is shown in the description, wherein R is alkyl or substituent alkyl; R(minute) is from natural amino acids. The invention also discloses a preparation method of the ALA-HPO conjugate. The invention also discloses the use of the ALA-HPO conjugate, i.e., the ALA-HPO conjugate is used for preparing drugs for photodynamics therapy.

Description

technical field [0001] The invention belongs to the field of chemical pharmacy, and relates to a class of 5-aminolevulinic acid (ALA)-iron chelator conjugates, a preparation method and application thereof—as a photodynamic therapy drug. Background technique [0002] Photodynamic therapy (PDT) is a new technology for selective treatment of (vascular) proliferative lesions that came out in the late 1970s, and has become one of the most active research fields in the world's tumor prevention and treatment science. PDT is a new disease treatment method based on the interaction of light, photosensitizer and oxygen; the photosensitizer (photodynamic therapy drug) is injected into the human body, and after a certain period of time, the tumor site is irradiated with light of a specific wavelength. A series of photochemical and photobiological reactions, with the participation of molecular oxygen, produces singlet oxygen and / or free radicals, oxidatively destroys various biological ma...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K5/065C07K1/10A61K38/05A61P35/00A61P17/12A61P31/20
CPCY02P20/55
Inventor 周涛思南·贝托朱纯风
Owner ZHEJIANG GONGSHANG UNIVERSITY
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