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Ibuprofen and ketoprofen potentiate UVA-induced cell death by a photosensitization process

Journal article
Authors E. Bignon
M. Marazzi
V. Besancenot
H. Gattuso
G. Drouot
C. Morell
Leif A Eriksson
S. Grandemange
E. Dumont
A. Monari
Published in Scientific Reports
Volume 7
ISSN 2045-2322
Publication year 2017
Published at Department of Chemistry and Molecular Biology
Language English
Links doi.org/10.1038/s41598-017-09406-8
Keywords nonsteroidal antiinflammatory drugs, singlet oxygen generation, electron-transfer, dna-damage, photoexcited benzophenone, force-field, nile blue, dynamics, pain, mechanism, Science & Technology - Other Topics
Subject categories Biological Sciences, Chemical Sciences

Abstract

Nonsteroidal 2-arylproprionic acids are widely used, over-the-counter, anti-inflammatory drugs. Photosensitivity is a commonly overlooked adverse effect of these drugs. Based on the combined use of cell viability assays and molecular modeling, we prove and rationalize the photochemical pathways triggering photosensitization for two drugs, ibuprofen and ketoprofen. As its parent compound benzophenone, ketoprofen produces singlet oxygen, upon triplet manifold population. However, ibuprofen and ketoprofen photodissociate and hence may generate two highly reactive radicals. The formation of metastable aggregates between the two drugs and B-DNA is also directly probed by molecular dynamics. Our approach characterizes the coupled influence of the drug's intrinsic photochemistry and the interaction pattern with DNA. The photosensitization activity of nonsteroidal 2-arylproprionic acids, being added to gels and creams for topical use, should be crucially analyzed and rationalized to enact the proper preventive measures.

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