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1-3 generation arylene ether dendritic phthalocyanine complex and polymer nano-particle thereof

A nanoparticle and dendritic technology, which is applied in the field of 1-3 generation aryl ether dendritic zinc phthalocyanine complexes and their polymer nanoparticles and preparation fields, can solve the problems of low uptake rate and enrichment effect of new tissues.

Inactive Publication Date: 2009-11-18
FUJIAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are no reports of 1-3 generation aryl ether dendritic phthalocyanine complexes whose end groups are carboxyl and cyano groups
[0004] Also, described phthalocyanine complexes all have a common weakness as second-generation photosensitizers, and the uptake rate and enrichment in newborn tissues are relatively low

Method used

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  • 1-3 generation arylene ether dendritic phthalocyanine complex and polymer nano-particle thereof
  • 1-3 generation arylene ether dendritic phthalocyanine complex and polymer nano-particle thereof
  • 1-3 generation arylene ether dendritic phthalocyanine complex and polymer nano-particle thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0089] In Example 1, the process 2) carbon tetrabromide was changed to 8g, triphenylphosphine was changed to 4g and tetrahydrofuran was changed to 20mL, and the reaction time was changed to 2h. Other reaction conditions were the same, and 4.0 g of white powdery solid substance (2) was obtained with a yield of 65.0%.

[0090] In process 4), carbon tetrabromide was changed to 15g, triphenylphosphine was changed to 8g and tetrahydrofuran was changed to 35mL, and the reaction time was changed to 2.5h. Other reaction conditions were the same, and 5.04 g of white powdery solid substance (4) was obtained with a yield of 80.0%.

[0091] In process 5), carbon tetrabromide was changed to 30g, triphenylphosphine was changed to 16g and tetrahydrofuran was changed to 60mL, and the reaction time was changed to 3.0h. Other reaction conditions were the same, and 5.25 g of white powdery solid substance (5) was obtained with a yield of 82%.

specific Embodiment 3

[0092] In Example 1, the reaction temperature of process 6) is 80° C., and other reaction conditions are the same, and the yield of the obtained substance (6) is 45.0%.

[0093] Process 7) The reaction temperature is 80°C, other reaction conditions are the same, and the yield of substance (7) is 30.0%.

[0094] Process 8) The reaction temperature is 80°C, other reaction conditions are the same, and the yield of substance (8) is 22.0%.

specific Embodiment 4

[0095] Synthetic method is the same as embodiment one, in process 9)-14), replaces zinc acetate with aluminum trichloride, other process is unchanged, obtains four-[3,5-bis-(4-cyanobenzyloxy)- 1-Methyleneoxyphenyl] aluminum phthalocyanine [G 1 -AlPc(CN) 8 ], productive rate 65%.IR (KBr / cm -1 ): 3449, 2921, 2231, 1601, 1452, 1168, 1059, 826, 640. 1 HNMR (400MHz, DMSO-d 6 , δ / ppm): 7.68(s, 4H), 7.25-7.26(d, J=4Hz, 4H), 7.18~7.19(d, J=4Hz, 4H) 7.66~7.68(d, J=8Hz, 16H) , 7.46~7.48 (d, J=8Hz, 16H), 6.58 (s, 8H), 6.52 (s, 4H), 5.06 (s, 24H). MALDI-TOF-MS: m / z=2068 [M+H 3 o + ]. Four-{3,5-bis-[3,5-bis-(4-cyanobenzyloxy)-1-methoxyphenyl]-1-methoxyphenyl}aluminum phthalocyanine [G 2 -AlPc(CN) 16 ], yield 62%. IR (KBr / cm -1 ): 3450, 2920, 2230, 1600, 1450, 1251, 1153, 1067, 822, 640. 1 H NMR (400MHz, DMSO-d 6 , δ / ppm): 7.81~7.83(d, J=8Hz, 32H), 7.56~7.58(d, J=8Hz, 32H), 7.39(s, 4H), 7.30(s, 4H), 7.20~7.22( d, J=8Hz, 4H), 6.70(s, 16H), 6.61(s, 12H), 6.57(s, 8H), 5.18(s, 40H...

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Abstract

The invention discloses a 1-3 generation arylene ether-substituted dendritic phthalocyanine zinc complex, a preparation method and an application thereof. The method comprises the following steps of adopting a Frechet synthesis method to synthesize the first to third generation alcohol molecules which take the 1-3 generation cyan as an end group; leading the first to third generation alcohols to react with 4-nitrophthalonitrile respectively, thus synthesizing corresponding phthalocyanine precursor of dendrimer taking the 1-3 generation cyan as the end group; subsequently, leading the phthalocyanine precursor ring of dendrimer taking the 1-3 generation cyan as the end group to synthesize corresponding arylene ether dendritic phthalocyanine taking the first to third generation cyan as the end group and the arylene ether dendritic phthalocyanine taking the first to third generation carboxyl as the end group generated by hydrolysis. The 1-3 generation arylene ether dendritic phthalocyanine complex and the amphiphilic block copolymer are automatically dissolved to form the polymer nano-particle loading the 1-3 generation arylene ether dendritic phthalocyanine complex. The 1-3 generation diaryl ether dendritic phthalocyanine zinc complex and the loaded polymer nano-particle thereof are used as photosencitizers for photodynamic therapy.

Description

Technical field: [0001] The invention belongs to the field of complexes, in particular to a 1-3 generation aryl ether dendritic zinc phthalocyanine complex, polymer nanoparticles and a preparation method thereof. The complex is used as a photosensitizer for photodynamic treatment of wet macular degeneration diseases and cancer. Background technique: [0002] Photodynamic therapy (PDT) is a new approach to treat cancer, HIV and wet macular degeneration-like diseases. The key to photodynamic therapy is the photosensitizer. Phthalocyanine complexes have a similar skeleton structure to hematoporphyrin, are more stable and easy to modify, and have a maximum absorption wavelength of around 670nm. They are easy to pass through the red light region of human tissues and can be made into pure products. They are considered to be a class of Potential photosensitizer. Due to the strong π-π interaction between phthalocyanine molecules, it is easy to aggregate, thereby reducing the fluo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22C08L77/04C08L71/02C08K5/3467A61K31/409A61K41/00A61K31/785
Inventor 彭亦如张宏黄宝铨
Owner FUJIAN NORMAL UNIV
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