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Pheophorbide curcumin ester with photosensitive activity and preparation method and application thereof

A technology of pheophorbide and curcumin ester, which is applied in the field of pheophorbide and curcumin ester and its preparation, can solve the problems of weak tissue penetration and weak tumor killing effect, and achieve deep tissue penetration , It is convenient for industrial production and the reaction conditions are easy to control

Inactive Publication Date: 2015-06-03
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Both have their own advantages and disadvantages. For example, pheophorbide has a longer photosensitive wavelength of 670nm and has certain tumor targeting, but its tumor killing effect is weak; curcumin has good anti-tumor effect, but its photosensitive wavelength is shorter than 425nm. , poor tissue penetration
[0005] Although there are many studies on porphyrin photosensitizer complexes, there is no report on forming an ester between pheophorbide and curcumin to overcome its shortcomings and form a new photosensitizer

Method used

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  • Pheophorbide curcumin ester with photosensitive activity and preparation method and application thereof
  • Pheophorbide curcumin ester with photosensitive activity and preparation method and application thereof
  • Pheophorbide curcumin ester with photosensitive activity and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Pheophorbide (0.6g, about 1mmol) and curcumin (0.4g, about 1mmol), add 50ml of chloroform, stir to dissolve; add N,N-dicyclohexylcarbodiimide DCC (0.1g , about 0.5mmol) to react, then slowly add DMAP (0.05g about 0.5mmol) to catalyze the reaction, and react at 30°C for 4 hours. After the reaction was completed, the mixed solution was washed three times with 100 ml of water, and the organic phase was dried over anhydrous magnesium sulfate, filtered, and distilled under reduced pressure to obtain 0.8 g of the product.

[0022] The product was analyzed by element composition, containing C70.3%, H5.8%, O17.7%, N6.2%, molecular weight 905, molecular formula: C 53 h 52 N 4 o 10 , NMR confirmed that there are 3 methoxyl hydrogens, 1 hydroxyl hydrogen, 5 carbonyl carbons, 2 benzene ring structures and 1 porphyrin structure in its structure, so it is deduced that its structure is 1 molecule of pheophorbide and turmeric The ester of element formation, as the structure of form...

Embodiment 2

[0026] Pheophorbide (0.6g, about 1mmol) and curcumin (0.4g, about 1mmol), add 50ml ethyl acetate, stir and dissolve; add N,N-dicyclohexylcarbodiimide DCC ( 0.2g, about 1mmol) to react, then slowly add DMAP (0.1g about 1mmol) to catalyze the reaction, and react at 40°C for 6 hours. After the reaction was completed, the mixture was washed three times with 100 ml of saturated brine, and the organic phase was dried over anhydrous sodium sulfate, filtered, and distilled under reduced pressure to obtain 0.9 g of the product.

[0027] The product was analyzed by element composition, containing C69.8%, H5.8%, O18.6%, N5.9%, molecular weight 947, molecular formula: C 55 h 54 N 4 o 11 , NMR confirmed that there are 3 methoxy hydrogens, 6 carbonyl carbons, 2 benzene ring structures and 1 porphyrin structure in its structure. Compared with formula III, there is one hydroxyl hydrogen less and one more acetyl group, so it is deduced that its The structure is that of formula IV.

[0028...

Embodiment 3

[0031] Pheophorbide (2.8g, about 5mmol) and curcumin (0.4g, about 1mmol), add 50ml of benzene, stir to dissolve; add concentrated sulfuric acid (0.5g, about 5mmol) dropwise under nitrogen protection, and react at 60°C for 8 Hours. After the reaction was completed, the mixture was washed three times with 100 ml of saturated brine, and the organic phase was dried over anhydrous sodium sulfate, filtered, and distilled under reduced pressure to obtain 1.5 g of the product.

[0032] The product was analyzed by element composition, containing C70.8%, H5.9%, O15.5%, N7.8%, molecular weight 1442, molecular formula: C 85 h 84 N 8 o 14 , NMR confirmed that there are 4 methoxy hydrogens, 8 carbonyl carbons, 2 benzene ring structures and 2 porphyrin structures in its structure, so it is speculated that its structure is formed by 2 molecules of pheophorbide and 1 molecule of curcumin Esters, such as the structure of formula II.

[0033] The product is insoluble in water, but soluble i...

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Abstract

The present invention discloses pheophorbide curcumin ester with photosensitive activity and preparation method and application thereof. The structure of pheophorbide curcumin ester with photosensitive activity is shown in formular I; the preparation method comprises mixing the pheophorbide acid and the curcumin at molar ratio of (1-5) :1 to be dissolved in the organic solvent, adding the catalyst under the protection of nitrogen for esterification reaction at the temperature of between 30 and 60 DEG C for 4 to 8 hours; rinsing the resultant reaction mixture with the saturated brine to obtain the organic phase to be dried, filtered and distilled at reduced pressure to obtain the pheophorbide curcumin ester with photosensitive activity; the dosage of catalyst accounts for 5 to 25% of that of raw materials, pheophorbide acid and curcumin; the organic solvent is one or more than one of chloroform, benzene and ethyl acetate. The pheophorbide curcumin ester provided by the present invention has characteristics of good targeting, long photosensitive wavelength, deeply tissue penetrating power and anti-tumor activity, and can be used as a novel photosensitizer applied to the photodynamic therapy.

Description

technical field [0001] The photosensitive composite material of the invention particularly relates to pheophorbide curcumin ester with photosensitive activity and its preparation method and application, belonging to the field of medicine. Background technique [0002] Photodynamic therapy is a treatment method that uses photosensitizers to generate singlet oxygen and destroy tumors under the excitation of light of specific wavelengths. This therapy has high treatment specificity, little damage to normal cells, and will not produce toxic and side effects of chemotherapy and radiotherapy, so it has a bright future. [0003] Photosensitizers are the key to photodynamic therapy. Early photosensitizers were hematoporphyrin derivatives, but they had allergic reactions and severe phototoxic reactions. Although a variety of photosensitizers have been studied recently, most of them are chemical synthesis products, which have certain safety hazards. [0004] Traditional Chinese medi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/22A61K31/409A61K41/00A61P35/00
Inventor 郑阳叶勇
Owner SOUTH CHINA UNIV OF TECH