Synthesis, singlet oxygen photogeneration and DNA photocleavage of porphyrins with nitrogen heterocycle tails

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 1O...

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Published inMolecules (Basel, Switzerland) Vol. 16; no. 5; pp. 3488 - 3498
Main Authors Zheng, Yun-Man, Wang, Kai, Li, Tian, Zhang, Xiu-Lan, Li, Zao-Yin
Format Journal Article
LanguageEnglish
Published Switzerland MDPI AG 26.04.2011
MDPI
Subjects
Angiogenesis
Cancer
DNA cleavage
DNA Cleavage - radiation effects
heterocyclic thiol
Kinases
Magnetic Resonance Spectroscopy
Mass Spectrometry
Molecular Structure
Nitrogen
Photochemistry
porphyrin
Porphyrins - chemistry
Signal transduction
Singlet Oxygen - chemistry
singlet oxygen generation
Tumors
Vascular endothelial growth factor
China
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Summary: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 1O(2) production rates against 5,10,15,20-tetraphenyl porphyrin (H(2)TPP) were described and the relative singlet oxygen production yields were：porphyrin 5 > porphyrins 1, 3, 4, 6-8, H(2)TPP > 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.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules16053488