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

Molecules

Yun-Man Zheng¹  Kai Wang¹  Tian Li¹  Xiu-Lan Zhang¹ 

[1] ¹College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, China ²Key Laboratory for Green Chemical Process of Ministry of Education, Wuhan Institute of Technology, Wuhan 430074, China

关键词: porphyrin;    singlet oxygen generation;    DNA cleavage;    heterocyclic thiol;   

DOI  :  10.3390/molecules16053488

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.