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Conjugates of 5-aminolevulinic acid and 3-hydroxypyridin-4-one, preparing method thereof and uses of the conjugates

A technology of aminolevulinic acid and hydroxypyridine, which is applied in the field of photodynamic therapy drugs, 5-aminolevulinic acid-iron chelator conjugates and its preparation, and can solve the problems of increasing the concentration of PpIX

Active Publication Date: 2015-01-07
浙江欧托电气有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It has been shown that the combination of ALA and iron chelators (such as deferoxamine, hydroxypyridone bidentate ligand) can significantly increase the concentration of PpIX in cells compared with ALA alone, but the ALA-iron chelator conjugates studies have not been reported

Method used

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  • Conjugates of 5-aminolevulinic acid and 3-hydroxypyridin-4-one, preparing method thereof and uses of the conjugates
  • Conjugates of 5-aminolevulinic acid and 3-hydroxypyridin-4-one, preparing method thereof and uses of the conjugates
  • Conjugates of 5-aminolevulinic acid and 3-hydroxypyridin-4-one, preparing method thereof and uses of the conjugates

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Embodiment 1, the preparation method of compound 1, carry out the following steps successively:

[0052] A, the synthesis of compound 6 containing free carboxyl,

[0053] One, the synthesis of compound 6a, carry out the following steps successively:

[0054] ①. Weigh 0.2g (1.1mmol) methyl 5-aminolevulinate hydrochloride (3), 0.305g (1mmol) N-benzyloxycarbonyl-L-phenylalanine (4a) and 6-chlorobenzene Triazole-1,1,3,3-tetramethyluronium hexafluorophosphate (HCTU, 0.414g, 1mmol) was dissolved in N,N-dimethylformamide (DMF, 4mL), and then 0.301 g (3mmol) triethylamine, stirred overnight at room temperature (12h), evaporated the solvent (DMF), dissolved the residue with dichloromethane (30mL), washed with 5% (mass%) sodium bicarbonate aqueous solution, anhydrous sodium sulfate After drying, the solvent (dichloromethane) was distilled off, and the residue was purified by silica gel column chromatography (eluted first with cyclohexane: ethyl acetate = 1:1 volume ratio, after...

Embodiment 2

[0085] Embodiment 2, the preparation of compound 2

[0086] Dissolve 100mg of compound 1 in 2mL of pyridine, cool to ≤5°C in an ice bath, add 0.4mL of acetic anhydride, stir in an ice bath for 15 minutes, add 2mL of ice water to the reaction solution, freeze-dry (i.e., in a vacuum freeze dryer Drying in medium temperature for 24h), compound 2 was obtained quantitatively.

[0087] instruction manual:

[0088] When it is compound 1a, it corresponds to compound 2a;

[0089] When it is compound 1f, the corresponding compound 2f is obtained;

[0090] When it is compound 1i, the corresponding compound 2i is obtained;

[0091] When it is compound 1j, the corresponding compound 2j is obtained;

[0092] And so on for the rest.

[0093] Compound 2a: 1 H NMR (CD 3 OD, 500MHz) δ1.52 (t, J=7.5Hz, 3H, CH 3 ),2.01(s,3H,CH 3 ), 2.63(t, J=6.5Hz, 2H, CH 2 ),2.75(t,J=6.5Hz,2H,CH 2 ),2.91and3.19(m,2H,CH 2 ),4.04(m,2H,CH 2 ), 4.38 (q, J=7.5Hz, 2H, CH 2 ),4.67(m,1H,CH),5.38(s,2H,CH 2...

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Abstract

The invention discloses conjugates of 5-aminolevulinic acid and 3-hydroxypyridin-4-one, namely ALA-HPO conjugates. The ALA-HPO conjugates are ALA-HPO conjugates 1 or ALA-HPO conjugates 2. The general structure formula of the ALA-HPO conjugates is a formula shown in the specification or another formula shown in the specification, wherein R is a natural amino acid, R' is alkyl or substituted alkyl, and R'' is alkyl, substituted alkyl or alkyl amino. A preparing method of the ALA-HPO conjugates is also provided by the invention. The ALA-HPO conjugates are used for preparing photodynamic therapeutic medicines.

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 Applications(China)
IPC IPC(8): C07D213/69A61K41/00A61P35/00A61P31/20
CPCY02P20/55C07D213/69A61K41/0057
Inventor 周涛思南·贝托朱纯风
Owner 浙江欧托电气有限公司
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