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Phosphamidon amphipathic phthalocyanine derivates, preparation method and application thereof in phototherapy medicament preparation

A phthalocyanine derivative and amphiphilic technology, which is applied in the field of photosensitizers, can solve the problems of not being able to significantly reduce the dark toxicity of phthalocyanine derivatives, system stability, and limited applications, and achieve good photosensitivity, low dark toxicity, and Effects of Good Physiological Compatibility

Inactive Publication Date: 2009-06-17
NANJING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The current solution is mainly through structural modification and construction of carriers. The new derivatives obtained by structural modification mainly include phthalocyanine derivatives with different water-soluble groups around them, axial water-soluble phthalocyanine compounds and amphiphilic phthalocyanine compounds. cyanine complexes, etc., but the test results show that most of the above derivatives cannot significantly reduce the dark toxicity of phthalocyanine derivatives
In addition, the reported carriers of phthalocyanine derivatives mainly include surfactants and liposomes. These carriers also limit their application in actual treatment due to their system stability.

Method used

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  • Phosphamidon amphipathic phthalocyanine derivates, preparation method and application thereof in phototherapy medicament preparation
  • Phosphamidon amphipathic phthalocyanine derivates, preparation method and application thereof in phototherapy medicament preparation
  • Phosphamidon amphipathic phthalocyanine derivates, preparation method and application thereof in phototherapy medicament preparation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Phosphamide amphipathic phthalocyanine (A1) whose phosphoamido amphiphilic phthalocyanine group is connected to the phthalocyanine parent benzene ring by p-hydroxybenzaldehyde is carried out according to the following reaction pathway:

[0027]

[0028]

[0029]

[0030] Concrete synthetic steps are as follows:

[0031] (1) Add 24.2g (0.2mol) of p-hydroxybenzaldehyde, 190mL of absolute ethanol, and 12.2g (0.2mol) of ethanolamine to the reaction flask in sequence, stir at room temperature for 4-5 hours, and filter the resulting solid after the reaction, and filter cake Recrystallized from absolute ethanol to obtain a light yellow solid 2 (21.7 g) with a yield of 66.4%.

[0032] Compound Identification:

[0033] m.p.: 166-168°C. IR: (KBr, cm -1 ): 3400-2600, 3080, 1640, 1606, 1516, 1287, 1169, 1060; 1 HNMR (DMSO-d 6 ): δ 9.87(s, 1H), 8.15(s, 1H), 7.56-7.54(d, 2H, J=8.0), 6.80-6.78(d, J=8.0, 2H), 4.56(s, 1H), 3.60-3.53 (m, 4H). (2) Under an ice-water bath, ...

Embodiment 2

[0052] Example 2 is basically the same as Example 1, but the ethanolamine described in step (1) of Example 1 is replaced with propanolamine to obtain dark green solid A2.

[0053] Compound Identification:

[0054] IR: (KBr, cm -1 ): 3247, 1608, 1510, 1473, 1338, 1244, 1021, 987; 1 HNMR: (DMSO-d 6 ): δ 8.99-8.94(m, 4H), 8.57-8.50(m, 4H), 7.85-7.79(m, 4H), 7.53-7.44(m, 16H), 4.53-4.49(m, 8H), 4.32- 4.25(m, 8H), 3.59-3.50(m, 8H); 1.81-1.72(m, 8H); Anal.Calcd for C 72 h 64 N 12 Na 8 o 20 P 4 Zn: C48.30, H3.60, N9.39; Found: C47.26, H3.57, N9.36.

Embodiment 3

[0055] Example 3, the synthesis of the phosphoramido amphiphilic phthalocyanine whose phosphoamido zwitterionic group is directly connected to the phthalocyanine parent benzene ring is basically the same as Example 1, but the steps (1) and (2) of Example 1 No, directly use step 3, using ethanolamine to react with 4-nitrophthalonitrile, and the rest of the steps are the same to obtain dark green solid A3.

[0056] Compound identification: IR: (KBr, cm -1 ): 3246, 1605, 1508, 1475, 1332, 1239, 1072, 981; Anal.Calcd for C 40 h 32 N 12 Na 8 o 16 P 4 Zn: C36.68; H, 2.46; N, 12.83; Found: C36.50, H2.37, N12.67.

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Abstract

The invention relates to phospham amphipathic phthalocyanine derivatives, a preparation method and application to the preparation of phototherapeutic medicines thereof. A structural general formula of the derivatives is shown as below: wherein p,q=0,1; p+q=1; q=0, p=2; n=1-5; m=0,1; R=Ch3, CH3CH2-, M is Zn or Al, M1 is H or Na. The phospham zwitterion group exists in the molecular structural formula of the phospham amphipathic phthalocyanine derivatives: p, q=0, 1; p+q=1; q=0, p=2; n=1-5; R=CH3, CH3CH2-, M1 is H or Na. The phospham amphipathic phthalocyanine derivatives are applied to the preparation of the phototherapeutic medicines.

Description

technical field [0001] The invention belongs to the technical field of photosensitizers with photodynamic activity, and relates to a phosphoramine amphiphilic phthalocyanine derivative, its preparation method and its application in the preparation of phototherapy drugs. Background technique [0002] Photodynamic therapy (PDT) is a new type of clinical tumor treatment technology. Its treatment principle is: administer phototherapeutic drugs to the human body, that is, photosensitizers. Under the excitation of suitable wavelength light, the photosensitizers can continuously produce various activities. Intermediate substances (such as singlet oxygen, superoxide anion, etc.), so as to kill diseased tissues and achieve the purpose of treating diseases. Compared with traditional treatment techniques, photodynamic therapy has two advantages of double selectivity (selective enrichment and selective illumination) and is not limited by the patient's constitution and age, which is espe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6561A61K31/675A61K41/00A61P35/00
Inventor 魏少华林云周家宏季春姚美玲王义成秦峰
Owner NANJING NORMAL UNIVERSITY
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