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 language | English |
|---|---|
| Pages (from-to) | 8742-8750 |
| Number of pages | 9 |
| Journal | Chemistry - A European Journal |
| Volume | 15 |
| Issue number | 35 |
| DOIs | |
| Publication status | Published - 2009 Sep 7 |
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All Science Journal Classification (ASJC) codes
- Catalysis
- Organic Chemistry
Cite this
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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 journal › Article
TY - JOUR
T1 - Photochemical activities of n-nitroso carboxamides and sulfoximides and their application to DNA cleavage
AU - Hwu, Jih Ru
AU - Huang, Joseph Jen Tse
AU - Tsai, Fu Yuan
AU - Tsay, Shwu Chen
AU - Hsu, Ming-Hua
AU - Hwang, Kuo Chu
AU - Horng, Jia Cherng
AU - Ho, Ja An Annie
AU - Lin, Chun Cheng
PY - 2009/9/7
Y1 - 2009/9/7
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=69749098712&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=69749098712&partnerID=8YFLogxK
U2 - 10.1002/chem.200802571
DO - 10.1002/chem.200802571
M3 - Article
C2 - 19658127
AN - SCOPUS:69749098712
VL - 15
SP - 8742
EP - 8750
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
SN - 0947-6539
IS - 35
ER -