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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,*
1 College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, China 2 Key Laboratory for Green Chemical Process of Ministry of Education, Wuhan Institute of Technology, Wuhan 430074, China
* Authors to whom correspondence should be addressed.
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 (CC BY 3.0).
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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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