Skiba, Joanna and Kowalczyk, Aleksandra and Fik, Marta A. and Gapinska, Magdalena and Trzybinski, Damian and Wozniak, Krzysztof and Vrcek, Valerije and Czerwieniec, Rafal and Kowalski, Konrad (2019) Luminescent pyrenyl-GNA nucleosides: synthesis, photophysics and confocal microscopy studies in cancer HeLa cells. PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES, 18 (10). pp. 2449-2460. ISSN 1474-905X, 1474-9092
Full text not available from this repository. (Request a copy)Abstract
Glycol 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.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | SIMPLIFIED NUCLEIC-ACID; ANTICANCER ACTIVITY; CRYSTAL-STRUCTURE; GENETIC SYSTEM; DNA; DUPLEX; RNA; OLIGONUCLEOTIDES; BASE; HYBRIDIZATION; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Physikalische und Theoretische Chemie > Chair of Chemistry III - Physical Chemistry (Molecular Spectroscopy and Photochemistry) > Prof. Dr. Hartmut Yersin |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 30 Mar 2020 06:35 |
| Last Modified: | 30 Mar 2020 06:35 |
| URI: | https://pred.uni-regensburg.de/id/eprint/26069 |
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