• Journal of the Korean Chemical Society
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• v.57 no.2
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• pp.246-251
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• 2013

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.

• Archives of Pharmacal Research
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• v.24 no.1
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• pp.39-43
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• 2001

4'-Bromoacetophenone analogs, which are able to generate monophenyl radicals capable of hydrogen atom abstraction, were investigated as possible photoinducible DNA cleaving agents. The potential of 4'-Bromoacetophenone as a possible new DNA cleaver is explored. Pyrrolecarboxatmid conjugated 4'-Bromoacetophenone, in particular, DNA cleaving activity and sequence-selectivity on the contiguous AT base pair sites.

• Proceedings of the PSK Conference
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• 2000.04a
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• pp.48-52
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• 2000

• Proceedings of the Korean Society of Applied Pharmacology
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• 2001.11a
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• pp.79-79
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• 2001

Genotoxic chemotherapeutics are irreversible DNA targeting agents, which can act as anticancer and antiviral drugs. Natural antibacterial and anticancer enediynes function through the formation of free radicals formed by Bergman-type cycloaromatization and being capable of cleavage of DNA strand. They have been focused primarily on the design and syntheses of simple enediyne structures, which can be mimic their mechanistic feature. Recently. I have been reported the possible application of 4'-bromoacetophenone as a simple photoactivatable DNA cleaving agent, which could be readily prepared and exhibit potent and selective DNA cleaving activity. Herein, we further investigated the activity of 4'-bromoacetophenone-pyrrolecarboxamides, which consist of both DNA cleaving element and recognition unit under various conditions in order to get more understanding of the mechanism of the action and find a broad spectrum of application.