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Ruthenium-anthraquinone conjugates, preparation method thereof and application for optical power therapeutic photosensitizer

A technology of photodynamic therapy and conjugates, which is applied in the field of photodynamic therapy photosensitizers, ruthenium-anthraquinone conjugates and their preparation, can solve the problems of large phototoxicity and side effects, shallow treatment depth, and poor photosensitizing activity, and achieve Simple synthetic route, high inhibition rate and high yield

Inactive Publication Date: 2008-02-06
GUANGDONG PHARMA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Clinically used photosensitizers such as hematoporphyrin derivatives are basically mixtures with relatively poor photosensitive activity and relatively large phototoxic side effects. After photodynamic therapy, patients often have to avoid light for a long time, and the treatment The depth is shallow, and the treatment effect on intracavity tumors is limited

Method used

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  • Ruthenium-anthraquinone conjugates, preparation method thereof and application for optical power therapeutic photosensitizer
  • Ruthenium-anthraquinone conjugates, preparation method thereof and application for optical power therapeutic photosensitizer
  • Ruthenium-anthraquinone conjugates, preparation method thereof and application for optical power therapeutic photosensitizer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Example 1 Preparation of 1,8-dihydroxy-9,10-anthraquinone)imidazo[4,5-f][1,10]phenanthroline (HAIP):

[0015]

[0016] Add o-phenanthroline and KBr mixture into a 125ml three-necked flask, stir, and add concentrated H2 dropwise under ice-cooling 2 SO 4 and concentrated HNO 3 Composition of mixed acid (v / v, 40:20) 60mL. After the dropwise addition, continue to reflux for 3 hours, add ice water to cool, and adjust the pH value to 6-7 with NaOH. Compound with CHCl 3 Extracted 3 times, the organic phase was removed with water, Na 2 SO 4 After drying, the solvent was filtered off to obtain an orange-yellow crude product. The crude product was recrystallized from ethanol to obtain o-phenanthroline 5,6-dione.

[0017] Take 1,10-phenanthrenequinone (525mg, 2.5mmol), ammonium acetate (3.88g, 50mmol) and 1,8-dihydroxy-9,10-anthraquinone-3-aldehyde (938mg, 3.5mmol), in 10ml of ice Reflux in acetic acid for 2 hours. Add 25ml of distilled water to the deep red solution o...

Embodiment 2

[0018] Embodiment 2 [Ru(bpy) 2 HAIP]·(PF 6 ) 2 preparation of

[0019]

[0020] cis-Ru(bpy) 2 Cl 2 2H 2 Preparation of O:

[0021] RuCl 3 ·nH 2 O (1.56g, 6mmol), bipyridine (1.87g, 12mmol), LiCl (1.68g, 28mmol), DMF (10ml) was added, and refluxed under the protection of argon for 8 hours. The reaction was cooled to room temperature and acetone (50ml) was added. The compound was left at 0°C for 24 hours to obtain purple-red crystals. The crystals were rinsed with cold water and acetone, and dried in vacuum with a yield of 81%. [Ru(bpy) 2 HAIP](PF 6 ) 2 Synthesis:

[0022] [Ru(bpy) 2 Cl 2 ]·2H 2 O (0.106g, 0.20mmol) and HAIP (0.095g, 0.20mmol), add 10cm 3 ethylene glycol. Reflux for 2 hours under argon protection. After cooling, add water (20cm 3 ), filtered to remove solid impurities. Join NH 4 PF 6 Removes dissolved impurities from the solution. The precipitated crystals were dried, dissolved in a small amount of methanol, and purified by alumina co...

Embodiment 3

[0023] Embodiment 3 [Ru(phen) 2 HAIP]·(PF 6 ) 2 preparation of

[0024]

[0025] cis-Ru(phen) 2 Cl 2 2H 2 Synthesis of O:

[0026] RuCl 3 ·nH 2 O (1.56g, 6mmol), phenanthroline (2.16g, 12mmol), LiCl (1.68g, 28mmol), DMF (10ml) were added, and refluxed for 8 hours under the protection of argon. After the reactant was cooled to room temperature, acetone (50 ml) was added to the reactant. The reactant was left at 0°C for 24 hours to obtain purple crystals. The crystals were rinsed with cold water and acetone, and dried in vacuum with a yield of 72%. [Ru(phen) 2 HAIP](PF 6 ) 2 Synthesis:

[0027] [Ru(phen) 2 Cl 2 ]·2H 2 O (0.114g, 0.20mmol) and HAIP (0.095g, 0.20mmol) were added to 10cm 3 Ethylene glycol was refluxed for 2 hours under the protection of argon. Add water (20cm 3 ) to remove solid impurities by filtration. Join NH 4 PF 6 Removes dissolved impurities from the solution. The precipitated crystals were dried, dissolved in a small amount of meth...

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Abstract

The invention discloses a ruthenium-anthraquinone conjugate, the preparation process thereof and the application as a photo-dynamic therapy photosensitizer. The general formula of the ruthenium-anthraquinone conjugate of the invention is [Ru(L)2HAIP].(PF6)2, the general formula of the HAIP is 1,8- dihydroxy -9,10- anthraquinoneimidazole [4,5-f][1,10] phenanthroline, the general of the L is bpy or phen. The preparation process for the ruthenium-anthraquinone conjugate comprises the following procedures: 1. the synthesis of the HAIP: 1,8- dihydroxy -9,10- anthraquinone-3-aldehyde is reacted with the phenanthroline5,6-diketone to produce the HAIP; 2. Ru(L)2Cl2 is reacted with HAIP and NH4PF6 to produce the [Ru(L)2HAIP].(PF6)2. The invention takes the aloe-emodin as the raw material and the ruthenium polypyridyl complex has single chemical composition; the synthesis route is simple and the yields are higher; during the experiment, the compound shows the light suppression to the growth of cancer cells.

Description

technical field [0001] The invention relates to the technical field of photodynamic therapy, in particular to a ruthenium-anthraquinone conjugate, a preparation method thereof and an application as a photosensitizer for photodynamic therapy. Background technique [0002] Photodynamic therapy is a minimally invasive treatment method produced in the 1970s. Its basic principle is to irradiate the lesion with light of a certain wavelength after intravenously injecting a photosensitizer to the patient for a certain period of time. Under this condition, the photosensitizer is excited to generate reactive oxygen species, causing damage to the lesion area. Due to the remarkable advantages of photodynamic therapy, such as strong selectivity, stable curative effect, small trauma, synergistic treatment, and palliative treatment, it is widely used clinically in tumor diseases and non-tumor diseases such as skin chloasma, ophthalmic diseases and viral diseases. Treatment of diseases etc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00A61K31/555A61P41/00A61P35/00
Inventor 梅文杰韦欣煜刘杰陆伟刚王娜
Owner GUANGDONG PHARMA UNIV
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