Ruthenium porphyrin complex and its prepn process and application as photosensitizer for photodynamic therapy

A complex, ruthenium porphyrin technology, applied in the field of photodynamic therapy photosensitizer ruthenium porphyrin complex and its preparation, can solve the problems of large phototoxic side effect, poor absorption and metabolism of photosensitizer, uncertain composition and the like

Inactive Publication Date: 2007-08-22
GUANGDONG PHARMA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

PDT photosensitizers currently used clinically, such as hematoporphyrin derivatives and cancer photophyrin, are basically mixtures with uncertain components. Photosensitizers have poor absorption and metabolism in vivo, and have relatively large phototoxic side effects.

Method used

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  • Ruthenium porphyrin complex and its prepn process and application as photosensitizer for photodynamic therapy
  • Ruthenium porphyrin complex and its prepn process and application as photosensitizer for photodynamic therapy
  • Ruthenium porphyrin complex and its prepn process and application as photosensitizer for photodynamic therapy

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Embodiment 1 [Ru(bpy) 2 Synthesis of (Cl)(m(3'-Py)TPP)]Cl cis-[Ru(bpy) 2 Cl 2 ]·2H 2 Synthesis of O: RuCl 3 ·nH 2 O (6mmol), bipyridine (12mmol) and lithium chloride (28mmol) were placed in a three-necked flask, 10mL of DMF was added, and heated to reflux for 8 hours under the protection of argon. After cooling to room temperature, 50 mL of acetone was added and frozen overnight. After suction filtration, the precipitate was washed several times with ice water and cold acetone, and dried in vacuo to obtain purple-black microcrystals with a yield of 81% (calculated as bipyridine).

[0043] m(3′-Py)TPP(123mg) and cis-[Ru(bpy) 2 Cl 2 ]·2H 2 O (123 mg) in acetic acid solution (10 mL) was refluxed for 24 hours. After the reaction, a purple-red solution was obtained, which was spin-dried under reduced pressure to obtain a purple-red homobody. The crude product was dissolved in acetonitrile and separated by neutral alumina column chromatography, rinsed with acetonitr...

Embodiment 2

[0044] Embodiment 2 [Ru(phen) 2 Synthesis of (Cl)(m(3'-Py)TPP)]Cl

[0045] Cis-[Ru(phen) 2 Cl 2 ]·2H 2 See Example 1 for the synthesis of O.

[0046] [Ru(phen) 2 Synthesis of (Cl)(m(3′-Py)TPP)]Cl: m(4′-Py)TPP (123mg) and Cis-[Ru(phen) 2 Cl 2 ]·2H 2 O (123 mg) in acetic acid solution (10 mL) was refluxed for 24 hours. After the reaction, a purple solution was obtained, which was spin-dried under reduced pressure. A purple solid was obtained. The crude product was dissolved in acetonitrile and separated by neutral alumina column chromatography, rinsed with acetonitrile:methanol (2:1, v / v), and the purple-red color band was collected, spin-dried under reduced pressure, and then recrystallized in acetonitrile / toluene solution. Yield 82%.

Embodiment 3

[0047] Embodiment 3 [Ru(dmbpy) 2 Synthesis of (Cl)(m(4'-Py)TPP)]Cl

[0048] Cis-[Ru(dmbpy) 2 Cl2 ]·2H 2 See Example 1 for the synthesis of O.

[0049] m(4′-Py)TPP(123mg) and Cis-[Ru(dmbpy) 2 Cl 2 ]·2H 2 O (123 mg) in acetic acid solution (10 mL) was refluxed for 24 hours. After the reaction, a purple solution was obtained, which was spin-dried under reduced pressure. Get the same body of purple. The crude product was dissolved in acetonitrile and separated by neutral alumina column chromatography, rinsed with acetonitrile:methanol (2:1, v / v), and the purple-red color band was collected, spin-dried under reduced pressure, and then recrystallized in acetonitrile / toluene solution. Yield 81%.

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Abstract

The present invention discloses ruthenium porphyrin complex and its preparation process and application as photosensitizer for photodynamic therapy. The ruthenium porphyrin complex with the structure as shown has ruthenium as the central metal ion, pyridyl radical containing asymmetrical porphyrin and its metal derivative as the ligand, and coordinate bond jointing the ruthenium pyridyl radical and the porphyrin ring. The ruthenium porphyrin complex of the present invention has determined composition, less toxic side effect and good absorption and metabolism in organism, and is suitable for use as photosensitizer for photodynamic therapy.

Description

technical field [0001] The invention relates to the field of pharmaceutical compounds, in particular to a photodynamic therapy photosensitizer ruthenium porphyrin complex and a preparation method thereof. Background technique [0002] Photodynamic therapy (PDT) is a minimally invasive tumor treatment method developed in the 1970s, and photosensitizers are key factors in photodynamic therapy. PDT photosensitizers currently used clinically, such as hematoporphyrin derivatives and cancer photophyrin, are basically mixtures with uncertain components. Photosensitizers have poor absorption and metabolism in vivo, and have relatively large phototoxic side effects. Contents of the invention [0003] The purpose of the present invention is to design and synthesize a ruthenium porphyrin complex with a definite composition as a photosensitizer for photodynamic therapy aiming at the shortcomings of the existing photosensitizers. [0004] Another object of the present invention is to ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00A61K31/409A61P35/00
Inventor 梅文杰韦欣煜刘云军
Owner GUANGDONG PHARMA UNIV
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