Water-soluble porphyrin gold (III) anticancer compounds and preparation method thereof

A porphyrin gold, water-soluble technology, applied in the field of water-soluble porphyrin gold anti-cancer compounds and its preparation, can solve the problems of being insoluble in water, etc., and achieve the effect of enhancing water solubility, good anti-cancer activity, and strong inhibitory effect

Inactive Publication Date: 2014-05-14
YANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, tetraphenylporphyrin gold (III) is soluble in organic solvents, but almost insoluble in water, which will directly affect its clinical application.

Method used

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  • Water-soluble porphyrin gold (III) anticancer compounds and preparation method thereof
  • Water-soluble porphyrin gold (III) anticancer compounds and preparation method thereof
  • Water-soluble porphyrin gold (III) anticancer compounds and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1 Chloride 5-(N-methyl-4-pyridyl iodide)-10,15,20-triphenylporphyrin gold (G2) compound and its preparation method.

[0031] Add 200 mL of propionic acid, benzaldehyde (60 mmol) and 4-pyridine aldehyde (20 mmol) into a 250 mL round bottom flask, and heat to reflux. After mixing 5.53mL (80mmol) freshly distilled pyrrole and 10mL propionic acid, slowly add it dropwise to the propionic acid solution within 30min. Then continue to react for 1 h, cool to room temperature, precipitate solid, filter, and wash the solid with methanol and hot water at 50-80°C, and dry. 5-(4-pyridyl)-10,15,20-triphenylporphyrin (L2) was obtained with a yield of 6.5%: mp>250°C; 1 H NMR (CDCl 3 , 600MHz), δ (ppm): -2.82 (s, 2H, inner-NH), 7.75-7.80 (m, 9H, Ph-CH), 8.17 (d, J=5.4Hz, 2H, Py-CH), 8.21(d, J=6.6Hz, 6H, Ph-CH), 8.79(d, J=4.2Hz, 2H, Py-CH), 8.86-8.90(m, 6H, Por-CH), 9.03(s, 2H , Por-CH); IR(KBr): υ3446(s), 1634(w), 1590(w), 1473(w), 1396(w), 1351(w), 1070(w), 970(w) , 798(m),...

Embodiment 2

[0034] Example 2 Chlorination of 5,10,15,20-tetrakis(4-sodium carboxylate) phenylporphyrin gold (G3) compound and its preparation method.

[0035] Add 200mL propionic acid and 4-methoxylbenzaldehyde (80mmol) into a 250mL round bottom flask, and heat to reflux. After mixing 5.53mL (80mmol) freshly distilled pyrrole and 10mL propionic acid, slowly add it dropwise to the propionic acid solution within 30min. Then continue to react for 1 h, cool to room temperature, precipitate solid, filter, and wash the solid with methanol and hot water at 50-80°C, and dry. 5,10,15,20-tetrakis(4-methoxyacyl)phenylporphyrin (L3) was obtained with a yield of 22.0%: mp>250°C; 1 H NMR (600MHz, CDCl 3 ), δ (ppm): -2.79 (s, 2H, inner-NH), 4.11 (s, 12H, -COOCH 3 ), 8.29 (d, J=7.8Hz, 8H, Ph-CH), 8.44 (d, J=7.8Hz, 8H, Ph-CH), 8.81 (s, 8H, Por-CH); IR(KBr): υ3425(m), 2919(w), 1724(s), 1607(w), 1435(w), 1383(w), 1277(m), 1108(m), 965(w), 803(w), 762(w)em -1 ; UV-Vis (CH 2 Cl 2 ) / nm 417, 515, 549, 5...

Embodiment 3

[0038] Example 3 Chloride 5-(4-sodium carboxylate)phenyl-10,15,20-triphenylporphyrin gold (G4) compound and its preparation method.

[0039] Add 200 mL of propionic acid, benzaldehyde (60 mmol) and 4-methoxybenzaldehyde (20 mmol) into a 250 mL round bottom flask, and heat to reflux. After mixing 5.53mL (80mmol) freshly distilled pyrrole and 10mL propionic acid, slowly add it dropwise to the propionic acid solution within 30min. Then continue to react for 1 h, cool to room temperature, precipitate solid, filter, and wash the solid with methanol and hot water at 50-80°C, and dry. 5-(4-methoxyacyl)phenyl-10,15,20-triphenylporphyrin (L4) was obtained in a yield of 9.0%: mp>250°C; 1 H NMR (CDCl 3 , 600MHz), δ (ppm): -2.79 (s, 2H, inner-NH), 4.11 (s, 3H, -COOCH 3 ), 7.74-7.79 (m, 9H, Ph-CH), 8.21 (d, J=6.6Hz, 6H, Ph-CH), 8.31 (d, J=7.8Hz, 2H, Ph-CH), 8.44 (d , J=7.8Hz, 2H, Ph-CH), 8.79(d, J=4.2Hz, 2H, Por-CH), 8.85(s, 6H, Por-CH); IR(KBr): υ3442(s), 3319(w), 2924(w), 2853(w), 1...

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Abstract

The invention discloses water-soluble porphyrin gold (III) anticancer compounds and a preparation method thereof, and belongs to the technical field of medicine preparation. The preparation method comprises the following steps of: reacting pyridyl, acyl, nitro and sulfo tetraphenyl porphyrin compounds are reacted with potassium chloroaurate to synthesize porphyrin gold chloride, and generating various salts to obtain a class of novel water-soluble porphyrin gold (III) compounds. In vitro S108 cell detection data proves that the compounds synthesized by the method have higher inhibition effect and have the inhibition rate of 71.133 percent. The method is scientific and reasonable; the prepared product has good water solubility and better anticancer activity; and the preparation process is simple and practicable and suitable for industrial production.

Description

technical field [0001] The invention discloses a water-soluble porphyrin gold (III) anticancer compound and a preparation method thereof, belonging to the technical field of medicine preparation. Background technique [0002] At present, the treatment of malignant tumors is an international problem. For cancer patients who are not suitable for surgery and are not suitable for radiotherapy, the most commonly used method is to apply anti-tumor chemical drugs, referred to as chemotherapy. Chemotherapy can shrink tumors to a certain extent and prevent cancer recurrence and metastasis. However, anti-tumor chemical drugs, including the metal compound cisplatin, have serious toxic and side effects, and the problem of drug resistance is also becoming more and more prominent. Therefore, the continuous development and discovery of new anti-tumor drugs is of great significance for human beings to overcome cancer and prolong life. Studies have shown that tetraphenylporphyrin gold (II...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/22A61P35/00
Inventor 许爱华王存德陈华圣李俊张宗磊沈婷婷许月
Owner YANGZHOU UNIV
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