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

Autori
Kowalski, Konrad ; Skiba, Joanna ; Kowalczyk, Aleksandra ; Fik, Marta Anna ; Gapińska, Magdalena ; Trzybiński, Damian ; Wozniak, Krzysztof ; Vrček, Valerije ; Czerwieniec, Rafał

Izvornik
Photochemical & photobiological sciences (1474-905X) 18 (2019); 2449-2460

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
pyrene, nucleoside, photochemistry, DFT, CD spectra

Sažetak
Glycol nucleic acids (GNA) are synthetic genetic-like polymers with an acyclic three-carbon propylene glycol phosphodiester backbone. Here, the synthesis, luminescence properties, circular dichroism (CD) spectra, and confocal microscopy speciation study in HeLa cells of (R, S) and (S, R) pyrenyl-GNA (pyr-GNA) nucleosides are reported. Enantiomerically pure nucleosides were obtained by a Sharpless asymmetric dihydroxylation reaction followed by HPLC separation using 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 comparison. The pyr-GNA nucleosides were not cytotoxic against human 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, cellular vesicles and in the 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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Farmacija

POVEZANOST RADA