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Synthesis, DNA Photocleavage and Singlet Oxygen Measurement of Cationic Bisporphyrins

Year: 2013
Type: article
Abstract: With - $OCH_2CO$ - as a linker, a non ${\beta}$ -substituted cationic bisporphyrin (4a) and a ${\beta}$ -substituted cationic bisporphyrin (4b) were prepared through methylation of the intermediate which was obtained from ${\beta}$ -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 ${\beta}$ -substituted cationic bisporphyrin was significantly weaker than that of $H_2TMPyP$ , but similar to that of non ${\beta}$ -substituted cationic bisporphyrin. While 4a and 4b showed substantial photocleavage activities toward DNA, with 68% and 66% observed at 10 ${\mu}M$ . The assessment of indirectly measured $^1O_2$ production rates against $H_2TMPyP$ were described and the relative singlet oxygen production yields were: free cationic bisporphyrins > $H_2TMPyP$ . The results showed the cationic bisporphyrins with ${\beta}$ -substitution and non ${\beta}$ -substitution could be developed as potential photodynamic agents.
Authors: Kai Wang, Qi Jin, Xiulan Zhang, Shuai-Hua Song
Language: English
Open Access status: bronze
OpenAlex ID: W2020894307
FWCI: 0.301
Cites: 12
Cited by: 4
Related to: 10