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Alkyl and aryl sulfonyl p-pyridine ethanone oximes are efficient DNA photo-cleavage agents

Paper ID Volume ID Publish Year Pages File Format Full-Text
29877 44445 2016 9 PDF Available
Title
Alkyl and aryl sulfonyl p-pyridine ethanone oximes are efficient DNA photo-cleavage agents
Abstract

•p-Pyridine sulfonyl ethanone oximes represent a novel class of DNA photo-cleavers.•Alkyl- and aryl-sulfonyloxyl radicals cause DNA single- and double-strand damages.•Sulfonyloxyl radicals are more effective than the carbonyloxyl ones.•p-Pyridine sulfonyl ethanone oximes act under aerobic and anaerobic conditions.•p-Pyridine sulfonyl ethanone oximes act at various pHs.

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.

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Keywords
DNA photo-cleavage; DNA binding; Sulfonyl ketoximes; Sulfonyloxyl radicals; Photo-cleavage agents
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology B: Biology - Volume 158, May 2016, Pages 30–38
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us