Article (Scientific journals)
Alkyl and aryl sulfonyl p-pyridine ethanone oximes are efficient DNA photo-cleavage agents
Andreou, Nicolaos-Panagiotis; Dafnopoulos, Konstantinos; Tortopidis, Christos et al.
2016In Journal of Photochemistry and Photobiology B: Biology, 158, p. 30-38
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Keywords :
DNA binding; DNA photo-cleavage; Photo-cleavage agents; Sulfonyl ketoximes; Sulfonyloxyl radicals
Abstract :
[en] Sulfonyloxyl radicals, readily generated upon UV irradiation of p-pyridine sulfonyl ethanone oxime derivatives, effectively cleave DNA, in a pH independent manner, and under either aerobic or anaerobic conditions. p-Pyridine sulfonyl ethanone oxime derivatives were synthesized from the reaction of p-pyridine ethanone oxime with the corresponding sulfonyl chlorides in good to excellent yields. All compounds, at a concentration of 100 μM, were irradiated at 312 nm for 15 min, after incubation with supercoiled circular pBluescript KS II DNA and resulted in extended single- and double- strand cleavages. The cleavage ability was found to be concentration dependent, with some derivatives exhibiting activity even at nanomolar levels. Besides that, p-pyridine sulfonyl ethanone oxime derivatives showed good affinity to DNA, as it was observed with UV interaction and viscosity experiments with CT DNA and competitive studies with ethidium bromide. The compounds interact to CT DNA probably by non-classical intercalation (i.e. groove-binding) and at a second step they may intercalate within the DNA base pairs. The fluorescence emission spectra of pre-treated EB-DNA exhibited a significant or moderate quenching. Comparing with the known aryl carbonyloxyl radicals the sulfonyloxyl ones are more powerful, with both aryl and alkyl sulfonyl substituted derivatives to exhibit DNA photo-cleaving ability, in significantly lower concentrations. These properties may serve in the discovery of new leads for "on demand" biotechnological and medical applications. © 2016 Elsevier B.V. All rights reserved.
Disciplines :
Biochemistry, biophysics & molecular biology
Identifiers :
eid=2-s2.0-84959305225
Author, co-author :
Andreou, Nicolaos-Panagiotis;  Laboratory of Organic, Bioorganic and Natural Product Chemistry, Molecular Biology and Genetics Department, Democritus University of Thrace, University Campus, Dragana, Alexandroupolis, Greece
Dafnopoulos, Konstantinos;  Laboratory of Organic, Bioorganic and Natural Product Chemistry, Molecular Biology and Genetics Department, Democritus University of Thrace, University Campus, Dragana, Alexandroupolis, Greece
Tortopidis, Christos;  Laboratory of Organic, Bioorganic and Natural Product Chemistry, Molecular Biology and Genetics Department, Democritus University of Thrace, University Campus, Dragana, Alexandroupolis, Greece
Koumbis, Alexandros E.;  Laboratory of Organic Chemistry, Chemistry Department, Aristotle University of Thessaloniki, Thessaloniki, Greece
KOFFA, Maria ;  University of Luxembourg > Faculty of Science, Technology and Communication (FSTC) > Life Science Research Unit
Psomas, George;  Laboratory of Inorganic Chemistry, Chemistry Department, Aristotle University of Thessaloniki, Thessaloniki, Greece
Fylaktakidou, Konstantina C.;  Laboratory of Organic, Bioorganic and Natural Product Chemistry, Molecular Biology and Genetics Department, Democritus University of Thrace, University Campus, Dragana, Alexandroupolis, Greece
External co-authors :
yes
Language :
English
Title :
Alkyl and aryl sulfonyl p-pyridine ethanone oximes are efficient DNA photo-cleavage agents
Publication date :
2016
Journal title :
Journal of Photochemistry and Photobiology B: Biology
ISSN :
1011-1344
Publisher :
Elsevier
Volume :
158
Pages :
30-38
Peer reviewed :
Peer Reviewed verified by ORBi
Available on ORBilu :
since 28 May 2016

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