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Pyrene-nucleobase conjugates: synthesis, oligonucleotide binding and confocal bioimaging studies

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cris.lastimport.scopus2024-02-12T19:37:07Z
dc.abstract.enFluorescent pyrene–linker–nucleobase (nucleobase = thymine, adenine) conjugates with carbonyl and hydroxy functionalities in the linker were synthesized and characterized. X-ray single-crystal structure analysis performed for the pyrene–C(O)CH2CH2–thymine (2) conjugate reveals dimers of molecules 2 stabilized by hydrogen bonds between the thymine moieties. The photochemical characterization showed structure-dependent fluorescence properties of the investigated compounds. The conjugates bearing a carbonyl function represent weak emitters as compared to compounds with a hydroxy function in the linker. The self-assembly properties of pyrene nucleobases were investigated in respect to their binding to single and double strand oligonucleotides in water and in buffer solution. In respect to the complementary oligothymidine T10 template in water, compounds 3 and 5 both show a self-assembling behavior according to canonical base–base pairing. However, in buffer solution, derivative 5 was much more effective than 3 in binding to the T10 template. Furthermore the adenine derivative 5 binds to the double-stranded (dA)10–T10 template with a self-assembly ratio of 112%. Such a high value of a self-assembly ratio can be rationalized by a triple-helix-like binding, intercalation, or a mixture of both. Remarkably, compound 5 also shows dual staining pattern in living HeLa cells. Confocal microscopy confirmed that 5 predominantly stains mitochondria but it also accumulates in the nucleoli of the cells.
dc.affiliationUniwersytet Warszawski
dc.contributor.authorCzerwieniec, Rafał
dc.contributor.authorTrzybiński, Damian
dc.contributor.authorWagenknecht, Hans-Achim
dc.contributor.authorFritz, Yannic
dc.contributor.authorWoźniak, Krzysztof
dc.contributor.authorBERNAŚ, TYTUS
dc.contributor.authorKowalski, Konrad
dc.contributor.authorJabłoński, Artur
dc.date.accessioned2024-01-25T18:42:51Z
dc.date.available2024-01-25T18:42:51Z
dc.date.copyright2017-11-28
dc.date.issued2017
dc.description.accesstimeAT_PUBLICATION
dc.description.financeNie dotyczy
dc.description.versionFINAL_PUBLISHED
dc.description.volume13
dc.identifier.doi10.3762/BJOC.13.249
dc.identifier.issn1860-5397
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/117630
dc.identifier.weblinkhttps://www.beilstein-journals.org/bjoc/articles/13/249
dc.languageeng
dc.pbn.affiliationchemical sciences
dc.relation.ispartofBeilstein Journal of Organic Chemistry
dc.relation.pages2521-2534
dc.rightsCC-BY
dc.sciencecloudnosend
dc.subject.enconfocal microscopy
dc.subject.enluminescence
dc.subject.ennucleobases
dc.subject.enoligonucleotide binding
dc.subject.enpyrene
dc.subject.enX-ray
dc.titlePyrene-nucleobase conjugates: synthesis, oligonucleotide binding and confocal bioimaging studies
dc.typeJournalArticle
dspace.entity.typePublication