Two Small Molecule Drugs with Topical Applications, Diflunisal and Naphazoline, and Their Potentially Toxic Photodegradants: Analysis by Chemical and Biological Methods

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dc.contributor.authorLejwoda, Karolina
dc.contributor.authorGumieniczek, Anna
dc.contributor.authorFilip, Agata
dc.contributor.authorNaumczuk, Beata
dc.contributor.editorWanhong Ma
dc.contributor.organizationDepartment of Medicinal Chemistry, Medical University of Lublin
dc.contributor.organizationDepartment of Cancer Genetics, Medical University of Lublin
dc.contributor.organizationInstitute of Organic Chemistry, Polish Academy of Sciences
dc.date.accessioned2024-09-02T11:11:41Z
dc.date.available2024-09-02T11:11:41Z
dc.date.issued2024
dc.description.abstractBecause of their topical application in patients and meaningful UV/VIS absorptive properties, the degradation and potential toxicity under irradiation of diflunisal (DIF) and naphazoline (NAF) were studied. In addition, the impact of pH on their photostability was examined, showing the highest degradation of acidic DIF at pH 1 and 13 and the highest degradation of basic NAF at pH below 7. An LC–UV analysis and chemical tests showed the first-order kinetics for their degradation and generation of reactive oxygen species (ROS). A UPLC-HRMS/MS analysis allowed us to identify four degradants of DIF (from DD-1 to DD-4) and six degradants of NAF (from ND-1 to ND-6). When Toxtree software was used, a high class III of toxicity was observed for DD-2, DD-3, and DD-4, and for all the NAF degradants. Furthermore, the ND-2 product, i.e., 2-[(1-methylnaphthalen-2-yl)methyl]-4,5-dihydro-1H-imidazole, was shown to present medium mutagenic and high tumorigenic effects according to OSIRIS Property Explorer. In addition, two in vitro tests on BALB/c 3T3 mouse fibroblasts showed a phototoxic effect of DIF and NAF at the lowest concentrations tested, i.e., 5 μg/mL. Thus, our present results could be useful to design further phototoxicity studies for DIF and NAF to minimize the risk of phototoxicity due to their photodegradation.en
dc.identifier.citationMolecules 2024, 29, 4122 ; https://doi.org/10.3390/molecules29174122
dc.identifier.doi10.3390/molecules29174122
dc.identifier.issn1420-3049
dc.identifier.urihttps://open.icm.edu.pl/handle/123456789/24793
dc.language.isoen
dc.publisherMDPI
dc.rightsUznanie autorstwa 4.0 Międzynarodoween
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/
dc.sourceMolecules
dc.subjectdiflunisal and naphazolineen
dc.subjectphotodegradationen
dc.subjectpH impacten
dc.subjectphototoxicityen
dc.subjectchromatographyen
dc.subjectin silico analysisen
dc.subjectin vitro testsen
dc.titleTwo Small Molecule Drugs with Topical Applications, Diflunisal and Naphazoline, and Their Potentially Toxic Photodegradants: Analysis by Chemical and Biological Methodsen
dc.typearticle
dc.type.versionpublishedVersion
person.identifier.orcidNaumczuk, Beata [0000-0003-3740-8387]
person.identifier.orcidLejwoda, Karolina [0000-0002-4843-2473]
person.identifier.orcidGumieniczek, Anna [0000-0002-2503-5272]
person.identifier.orcidNaumczuk, Beata [0000-0003-3740-8387]
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