Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/150414
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dc.contributor.authorKrishna, Manchugondanahalli S.en_US
dc.contributor.authorWang, Zhenzhangen_US
dc.contributor.authorZheng, Liangzhenen_US
dc.contributor.authorBowry, Jogeshen_US
dc.contributor.authorOng, Alan Ann Lerken_US
dc.contributor.authorMu, Yuguangen_US
dc.contributor.authorPrabakaran, Mookkanen_US
dc.contributor.authorChen, Gangen_US
dc.date.accessioned2021-05-24T05:41:44Z-
dc.date.available2021-05-24T05:41:44Z-
dc.date.issued2019-
dc.identifier.citationKrishna, M. S., Wang, Z., Zheng, L., Bowry, J., Ong, A. A. L., Mu, Y., Prabakaran, M. & Chen, G. (2019). Incorporating G-C pair-recognizing Guanidinium into PNAs for sequence and structure specific recognition of dsRNAs over dsDNAs and ssRNAs. Biochemistry, 58(36), 3777-3788. https://dx.doi.org/10.1021/acs.biochem.9b00608en_US
dc.identifier.issn0006-2960en_US
dc.identifier.other0000-0002-2499-026X-
dc.identifier.other0000-0002-8772-9755-
dc.identifier.urihttps://hdl.handle.net/10356/150414-
dc.description.abstractRecognition of RNAs under physiological conditions is important for the development of chemical probes and therapeutic ligands. Nucleobase-modified dsRNA-binding PNAs (dbPNAs) are promising for the recognition of dsRNAs in a sequence and structure specific manner under near-physiological conditions. Guanidinium is often present in proteins and small molecules for the recognition of G bases in nucleic acids, in cell-penetrating carriers, and in bioactive drug molecules, which might be due to the fact that guanidinium is amphiphilic and has unique hydrogen bonding and stacking properties. We hypothesized that a simple guanidinium moiety can be directly incorporated into PNAs to facilitate enhanced molecular recognition of G-C pairs in dsRNAs and improved bioactivity. We grafted a guanidinium moiety directly into a PNA monomer (designated as R) using a two-carbon linker as guided by computational modeling studies. The synthetic scheme of the PNA R monomer is relatively simple compared to that of the previously reported L monomer. We incorporated the R residue into various dbPNAs for binding studies. dbPNAs incorporated with R residues are excellent in sequence specifically recognizing G-C pairs in dsRNAs over dsDNA and ssRNAs. We demonstrated that the R residue is compatible with unmodified T and C and previously developed modified L and Q residues in dbPNAs for targeting model dsRNAs, the influenza A viral panhandle duplex structure, and the HIV-1 frameshift site RNA hairpin. Furthermore, R residues enhance the cellular uptake of PNAs.en_US
dc.description.sponsorshipAgency for Science, Technology and Research (A*STAR)en_US
dc.description.sponsorshipMinistry of Education (MOE)en_US
dc.description.sponsorshipNanyang Technological Universityen_US
dc.language.isoenen_US
dc.relationRG152/17en_US
dc.relationMOE2015-T2-1-028en_US
dc.relationRG146/17en_US
dc.relation.ispartofBiochemistryen_US
dc.rightsThis document is the Accepted Manuscript version of a Published Work that appeared in final form in Biochemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.biochem.9b00608en_US
dc.subjectScience::Biological sciencesen_US
dc.titleIncorporating G-C pair-recognizing Guanidinium into PNAs for sequence and structure specific recognition of dsRNAs over dsDNAs and ssRNAsen_US
dc.typeJournal Articleen
dc.contributor.schoolSchool of Physical and Mathematical Sciencesen_US
dc.contributor.schoolSchool of Biological Sciencesen_US
dc.identifier.doi10.1021/acs.biochem.9b00608-
dc.description.versionAccepted versionen_US
dc.identifier.pmid31424191-
dc.identifier.scopus2-s2.0-85071998753-
dc.identifier.issue36en_US
dc.identifier.volume58en_US
dc.identifier.spage3777en_US
dc.identifier.epage3788en_US
dc.subject.keywordsGuanidiniumen_US
dc.subject.keywordsDouble-stranded RNAsen_US
dc.description.acknowledgementThis work was supported by a NTU-A*STAR Seed Funding Research Award (2018), a Singapore Ministry of Education (MOE) Tier 1 grant (RG152/17), and a MOE Tier 2 grant (MOE2015-T2-1-028) to G.C. The work was also supported by a MOE Tier 1 grant (RG146/17) to Y.M.en_US
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