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

Research output: Contribution to journalArticle

7 Citations (Scopus)

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

Fingerprint

DNA
Irradiation
Nitroso Compounds
Nitric oxide
Photolysis
Benzene
Ultraviolet radiation
Oxides
Paramagnetic resonance
Buffers
Nitric Oxide
Phosphates
Decomposition
2-phenyl-4,4,5,5-tetramethylimidazoline-1-oxyl-3-oxide
9-fluorenone
fluorene

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

Cite this

Hwu, Jih Ru ; Huang, Joseph Jen Tse ; Tsai, Fu Yuan ; Tsay, Shwu Chen ; Hsu, Ming-Hua ; Hwang, Kuo Chu ; Horng, Jia Cherng ; Ho, Ja An Annie ; Lin, Chun Cheng. / Photochemical activities of n-nitroso carboxamides and sulfoximides and their application to DNA cleavage. In: Chemistry - A European Journal. 2009 ; Vol. 15, No. 35. pp. 8742-8750.
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Hwu, JR, Huang, JJT, Tsai, FY, Tsay, SC, Hsu, M-H, Hwang, KC, Horng, JC, Ho, JAA & Lin, CC 2009, 'Photochemical activities of n-nitroso carboxamides and sulfoximides and their application to DNA cleavage', Chemistry - A European Journal, vol. 15, no. 35, pp. 8742-8750. https://doi.org/10.1002/chem.200802571

Photochemical activities of n-nitroso carboxamides and sulfoximides and their application to DNA cleavage. / Hwu, Jih Ru; Huang, Joseph Jen Tse; Tsai, Fu Yuan; Tsay, Shwu Chen; Hsu, Ming-Hua; Hwang, Kuo Chu; Horng, Jia Cherng; Ho, Ja An Annie; Lin, Chun Cheng.

In: Chemistry - A European Journal, Vol. 15, No. 35, 07.09.2009, p. 8742-8750.

Research output: Contribution to journalArticle

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AU - Hwu, Jih Ru

AU - Huang, Joseph Jen Tse

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AU - Tsay, Shwu Chen

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AU - Lin, Chun Cheng

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