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

doi:10.1002/chem.200802571

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

Department of Chemistry

Research output: Contribution to journal › Article

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 language	English
Pages (from-to)	8742-8750
Number of pages	9
Journal	Chemistry - A European Journal
Volume	15
Issue number	35
DOIs	https://doi.org/10.1002/chem.200802571
Publication status	Published - 2009 Sep 7

Fingerprint

All Science Journal Classification (ASJC) codes

Catalysis
Organic Chemistry

Cite this

Hwu, J. R., Huang, J. J. T., Tsai, F. Y., Tsay, S. C., Hsu, M. H., Hwang, K. C., ... Lin, C. C. (2009). Photochemical activities of n-nitroso carboxamides and sulfoximides and their application to DNA cleavage. Chemistry - A European Journal, 15(35), 8742-8750. https://doi.org/10.1002/chem.200802571

@article{c94e6a7f238d486ab7144f4ca70082cc,

title = "Photochemical activities of n-nitroso carboxamides and sulfoximides and their application to DNA cleavage",

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.",

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

year = "2009",

month = "9",

day = "7",

doi = "10.1002/chem.200802571",

language = "English",

volume = "15",

pages = "8742--8750",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "Wiley-VCH Verlag",

number = "35",

}

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 -

Access to Document

10.1002/chem.200802571