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Molecules 2011, 16(5), 3488-3498; doi:10.3390/molecules16053488
Article

Synthesis, Singlet Oxygen Photogeneration and DNA Photocleavage of Porphyrins with Nitrogen Heterocycle Tails

1
,
2,* , 2
,
2
 and
1,*
Received: 11 March 2011 / Revised: 13 April 2011 / Accepted: 18 April 2011 / Published: 26 April 2011
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Abstract

Eight novel compounds were prepared by reaction of 5-(bromo- propoxyphenyl)-10,15,20-triphenylporphyrin with oxazole thiols, 1,3,4-oxadiazole thiols and 1,3,4-thiadiazole thiols, and their structures confirmed by UV-vis, IR, 1H-NMR, MS and elemental analysis. The assessment of indirectly measured 1O2 production rates against 5,10,15,20-tetraphenyl porphyrin (H2TPP) were described and the relative singlet oxygen production yields were:porphyrin 5 > porphyrins 1, 3, 4, 6-8, H2TPP > porphyrin 2. Porphyrin 4 and porphyrin 7 showed substantial photocleavage activities toward DNA, with over 75% cleavage observed at 40 µM. It suggested that these those porphyrins with nitrogen heterocycle tails are potential photosensitive agents.
Keywords: porphyrin; singlet oxygen generation; DNA cleavage; heterocyclic thiol porphyrin; singlet oxygen generation; DNA cleavage; heterocyclic thiol
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Zheng, Y.-M.; Wang, K.; Li, T.; Zhang, X.-L.; Li, Z.-Y. Synthesis, Singlet Oxygen Photogeneration and DNA Photocleavage of Porphyrins with Nitrogen Heterocycle Tails. Molecules 2011, 16, 3488-3498.

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