Photochemical activities of n-nitroso carboxamides and sulfoximides and their application to DNA cleavage

Jih Ru Hwu, Joseph Jen Tse Huang, Fu Yuan Tsai, Shwu Chen Tsay, Ming Hua Hsu, Kuo Chu Hwang, Jia Cherng Horng, Ja An Annie Ho, Chun Cheng Lin

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Abstract

N-Nitroso compounds containing benzene, fluorene or fluorenone rings were synthesized. Photolysis of these compounds with 312-nm UV light provided the NO species, the presence of which was corroborated by use of an EPR method and of 2phenyl-4,4,5,5-tetramethylimidazolin-loxyl 3-oxide (PTIO) as a trapping agent. During irradiation of N-methylN-nitroso-9-fluorenone carboxamide (14c) in the absence of PTIO, it underwent decomposition followed by re-combination to give the heterocyclic nitric oxide radical 15. Incorporation of intercalating moieties endowed the Nnitroso compounds with DNA-cleaving ability through single-strand scission upon UV irradiation in a phosphate buffer (pH 5.0-8.0) under aerobic conditions.

Original languageEnglish
Pages (from-to)8742-8750
Number of pages9
JournalChemistry - A European Journal
Volume15
Issue number35
DOIs
Publication statusPublished - 2009 Sep 7

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All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

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