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Luminescent pyrenyl-GNA nucleosides: synthesis, photophysics and confocal microscopy studies in cancer HeLa cells

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dc.abstract.enGlycol nucleic acids (GNA) are synthetic genetic-like polymers with an acyclic three-carbon propylene glycol phosphodiester backbone. Here, synthesis, luminescence properties, circular dichroism (CD) spectra, and confocal microscopy speciation studies of (R,S) and (S,R) pyrenyl-GNA (pyr-GNA) nucleosides are reported in HeLa cells. Enantiomerically pure nucleosides were obtained by a Sharpless asymmetric dihydroxylation reaction followed by semi-preparative high-performance liquid chromatography (HPLC) separation using Amylose-2 as the chiral stationary phase. The enantiomeric relationship between stereoisomers was confirmed by CD spectra, and the absolute configurations were assigned based on experimental and theoretical CD spectra comparisons. The pyr-GNA nucleosides were not cytotoxic against human cervical (HeLa) cancer cells and thus were utilized as luminescent probes in the imaging of these cells with confocal microscopy. Cellular staining patterns were identical for both enantiomers in HeLa cells. Compounds showed no photocytotoxic effect and were localized in the lipid membranes of the mitochondria, in cellular vesicles and in other lipid cellular compartments. The overall distribution of the pyrene and pyrenyl-GNA nucleosides inside the living HeLa cells differed, since the former compound gives a more granular staining pattern and the latter a more diffuse one
dc.affiliationUniwersytet Warszawski
dc.contributor.authorCzerwieniec, Rafał
dc.contributor.authorVrček, Valerije
dc.contributor.authorFik-Jaskółka, Marta
dc.contributor.authorKowalski, Konrad
dc.contributor.authorTrzybiński, Damian
dc.contributor.authorWoźniak, Krzysztof
dc.contributor.authorKowalczyk, Aleksandra
dc.contributor.authorGapińska, Magdalena
dc.contributor.authorSkiba, Joanna
dc.date.accessioned2024-01-25T05:29:52Z
dc.date.available2024-01-25T05:29:52Z
dc.date.issued2019
dc.description.financeNie dotyczy
dc.description.number10
dc.description.volume18
dc.identifier.doi10.1039/C9PP00271E
dc.identifier.issn1474-905X
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/111599
dc.identifier.weblinkhttps://doi.org/10.1039/C9PP00271E
dc.languageeng
dc.pbn.affiliationchemical sciences
dc.relation.ispartofPhotochemical and Photobiological Sciences
dc.relation.pages2449-2460
dc.rightsClosedAccess
dc.sciencecloudnosend
dc.titleLuminescent pyrenyl-GNA nucleosides: synthesis, photophysics and confocal microscopy studies in cancer HeLa cells
dc.typeJournalArticle
dspace.entity.typePublication