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Replacement of the phosphodiester backbone between canonical nucleosides with a dirhenium carbonyl “click” linker—a new class of luminescent organometallic dinucleoside phosphate mimics

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cris.lastimport.scopus2024-02-12T20:52:27Z
dc.abstract.enThe first-in-class luminescent dinucleoside phosphate analogs with a [Re-2(mu-Cl)(2)(CO)(6)(mu-pyridazine)] "click" linker as a replacement for the natural phosphate group are reported together with the synthesis of luminescent adenosine and thymidine derivatives having the [Re-2(mu-Cl)(2)(CO)(6)(mu-pyridazine)] entity attached to positions 5 ' and 3 ', respectively. These compounds were synthesized by applying inverse-electron-demand Diels-Alder and copper(i)-catalyzed azide-alkyne 1,3-dipolar cycloaddition reactions in three or four steps. The obtained compounds exhibited orange emission (lambda(PL) approximate to 600 nm, phi(PL) approximate to 0.10, and tau = 0.33-0.61 mu s) and no toxicity (except for one nucleoside) to human HeLa cervical epithelioid and Ishikawa endometrial adenocarcinoma cancer cells in vitro. Furthermore, the compounds' ability to inhibit the growth of Gram-positive Staphylococcus aureus and Gram-negative Escherichia coli bacterial strains was moderate and only observed at a high concentration of 100 mu M. Confocal microscopy imaging revealed that the "dirhenium carbonyl" dinucleosides and nucleosides localized mainly in the membranous structures of HeLa cells and uniformly inside S. aureus and E. coli bacterial cells. An interesting finding was that some of the tested compounds were also found in the nuclei of HeLa cells.
dc.affiliationUniwersytet Warszawski
dc.contributor.authorWoźniak, Krzysztof
dc.contributor.authorTrzybiński, Damian
dc.contributor.authorKowalski, Konrad
dc.contributor.authorStróżek, Józef
dc.contributor.authorGapińska, Magdalena
dc.contributor.authorDutkiewicz, Natalia
dc.contributor.authorGorski, Aleksander
dc.contributor.authorKowalczyk, Aleksandra
dc.contributor.authorSkiba, Joanna
dc.date.accessioned2024-01-25T19:11:59Z
dc.date.available2024-01-25T19:11:59Z
dc.date.issued2023
dc.description.financeŚrodki finansowe, o których mowa w art. 365 pkt. 2 ustawy
dc.description.number6
dc.description.volume52
dc.identifier.doi10.1039/D2DT03995H
dc.identifier.issn1477-9226
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/118408
dc.identifier.weblinkhttp://pubs.rsc.org/en/content/articlepdf/2023/DT/D2DT03995H
dc.languageeng
dc.pbn.affiliationchemical sciences
dc.relation.ispartofDalton Transactions
dc.relation.pages1551-1567
dc.rightsClosedAccess
dc.sciencecloudnosend
dc.titleReplacement of the phosphodiester backbone between canonical nucleosides with a dirhenium carbonyl “click” linker—a new class of luminescent organometallic dinucleoside phosphate mimics
dc.typeJournalArticle
dspace.entity.typePublication