Synthesis, DNA Photocleavage and Singlet Oxygen Measurement of Cationic Bisporphyrins

Journal of the Korean Chemical Society

Qi Jin¹  Xiulan Zhang¹  Kai Wang¹  Shuai Hua Song¹ 

关键词: Cationic bisporphyrin;    DNA photocleavage;    Singlet oxygen;    Photosensitizer;   

DOI  :  

学科分类：化学（综合）

来源: Korean Chemical Society

【 摘 要 】

With -OCH2CO- as a linker, a non ¥â-substituted cationic bisporphyrin (4a) and a ¥â-substituted cationic bisporphyrin (4b) were prepared through methylation of the intermediate which was obtained from ¥â-amino-5,10,15,20-tetra (4-cyanophenyl) porphyrin or 5-hydroxylphenyl-10,15,20-tris(4-cyanophenyl) reacting with 5-hydroxy-10,15,20-trispyridinylporphyrin. Their structures were confirmed by 1H NMR, IR, UV-vis, MS and elemental analysis. DNA photocleavage ability and the singlet oxygen ability of those cationic bisporphyrins were investigated. DNA photocleavage activity of ¥â-substituted cationic bisporphyrin was significantly weaker than that of H2TMPyP, but similar to that of non ¥â-substituted cationic bisporphyrin. While 4a and 4b showed substantial photocleavage activities toward DNA, with 68% and 66% observed at 10 ¥ìM. The assessment of indirectly measured 1O2 production rates against H2TMPyP were described and the relative singlet oxygen production yields were: free cationic bisporphyrins > H2TMPyP. The results showed the cationic bisporphyrins with ¥â-substitution and non ¥â- substitution could be developed as potential photodynamic agents.

【 授权许可】

Unknown