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Does a Conjugation Site Affect Transport of Vitamin B12–Peptide Nucleic Acid Conjugates into Bacterial Cells?

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dc.abstract.enAbstract Gram-negative bacteria develop specific systems for the uptake of scarce nutrients, including vitamin B12. These uptake pathways may be utilized for the delivery of biologically relevant molecules into cells. Indeed, it was recently reported that vitamin B12 transported an antisense peptide nucleic acid (PNA) into Escherichia coli and Salmonella Typhimurium cells. The present studies indicate that the conjugation site of PNA to vitamin B12 has an impact on PNA transport into bacterial cells. Toward this end, a specifically designed PNA oligomer has been tethered at various positions of vitamin B12 (central Co, R5′-OH, c and e amide chains, meso position, and at the hydroxy group of cobinamide) by using known or newly developed methodologies and tested for the uptake of the synthesized conjugates by E. coli. Compounds in which the PNA oligonucleotide was anchored at the R5′-OH position were transported more efficiently than that of other compounds tethered at the peripheral positions around the corrin ring. Of importance is the fact that, contrary to mammalian organisms, E. coli also takes up cobinamide, which is an incomplete corrinoid. This selectivity opens up ways to fight bacterial infections.
dc.affiliationUniwersytet Warszawski
dc.contributor.authorTrylska, Joanna
dc.contributor.authorWierzba, Aleksandra
dc.contributor.authorWojciechowska, Monika
dc.contributor.authorNexø, Ebba
dc.contributor.authorRównicki, Marcin
dc.contributor.authorWincenciuk, Aleksandra
dc.contributor.authorGRYKO, Dorota
dc.contributor.authorMaximova, Ksenia
dc.date.accessioned2024-01-24T22:11:47Z
dc.date.available2024-01-24T22:11:47Z
dc.date.issued2018
dc.description.financeNie dotyczy
dc.description.number70
dc.description.volume24
dc.identifier.doi10.1002/CHEM.201804304
dc.identifier.issn0947-6539
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/105149
dc.identifier.weblinkhttps://doi.org/10.1002/chem.201804304
dc.languageeng
dc.pbn.affiliationchemical sciences
dc.relation.ispartofChemistry - A European Journal
dc.relation.pages18772-18778
dc.rightsClosedAccess
dc.sciencecloudnosend
dc.subject.enbioconjugation drug delivery peptide nucleic acids natural products structure–activity relationships
dc.titleDoes a Conjugation Site Affect Transport of Vitamin B12–Peptide Nucleic Acid Conjugates into Bacterial Cells?
dc.typeJournalArticle
dspace.entity.typePublication