gamma-(S)-Guanidinylmethyl-Modified Triplex-Forming Peptide Nucleic Acids Increase Hoogsteen-Face Affinity for a MicroRNA and Enhance Cellular Uptake

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dc.contributor.authorTähtinen V
dc.contributor.authorVerhassel A
dc.contributor.authorTuomela J
dc.contributor.authorVirta P
dc.contributor.organizationfi=biolääketieteen laitos|en=Institute of Biomedicine|
dc.contributor.organizationfi=lääkekehityksen kemia|en=Pharmaseutical Chemistry|
dc.contributor.organizationfi=tyks, vsshp|en=tyks, varha|
dc.contributor.organization-code1.2.246.10.2458963.20.77952289591
dc.contributor.organization-code1.2.246.10.2458963.20.93793350823
dc.contributor.organization-code2606303
dc.contributor.organization-code2607100
dc.converis.publication-id42614349
dc.converis.urlhttps://research.utu.fi/converis/portal/Publication/42614349
dc.date.accessioned2022-10-28T13:31:47Z
dc.date.available2022-10-28T13:31:47Z
dc.description.abstractgamma-Modified (i.e., (S)-aminomethyl, (S)-acetamidomethyl, (R)-4-(hydroxymethyl)triazol-1-ylmethyl, and (S)-guanidinylmethyl) triplex-forming peptide nucleic acids (TFPNAs) were synthesized and the effect of the backbone modifications on the binding to a miR-215 model was studied. Among the modifications, an appropriate pattern of three gamma-(S)-guanidinylmethyl modifications increased the affinity and Hoogsteen-face selectivity for the miR-215 model without ternary (PNA)(2)/RNA complex formation. Moreover, the gamma-(S)-guanidinylmethyl groups were observed to facilitate internalization of the TFPNAs into living PC-3 prostate cancer cells.
dc.format.pagerange3041
dc.format.pagerange3051
dc.identifier.eissn1439-4227
dc.identifier.jour-issn1439-4227
dc.identifier.olddbid182709
dc.identifier.oldhandle10024/165803
dc.identifier.urihttps://www.utupub.fi/handle/11111/40046
dc.identifier.urnURN:NBN:fi-fe2021042827509
dc.language.isoen
dc.okm.affiliatedauthorTähtinen, Ville
dc.okm.affiliatedauthorVerhassel, Alejandra
dc.okm.affiliatedauthorTuomela, Johanna
dc.okm.affiliatedauthorVirta, Pasi
dc.okm.affiliatedauthorDataimport, tyks, vsshp
dc.okm.discipline116 Chemical sciencesen_GB
dc.okm.discipline3111 Biomedicineen_GB
dc.okm.discipline116 Kemiafi_FI
dc.okm.discipline3111 Biolääketieteetfi_FI
dc.okm.internationalcopublicationnot an international co-publication
dc.okm.internationalityInternational publication
dc.okm.typeA1 ScientificArticle
dc.publisherWILEY-V C H VERLAG GMBH
dc.publisher.countryGermanyen_GB
dc.publisher.countrySaksafi_FI
dc.publisher.country-codeDE
dc.publisher.placeWEINHEIM
dc.relation.doi10.1002/cbic.201900393
dc.relation.ispartofjournalChemBioChem
dc.relation.issue24
dc.relation.volume20
dc.source.identifierhttps://www.utupub.fi/handle/10024/165803
dc.titlegamma-(S)-Guanidinylmethyl-Modified Triplex-Forming Peptide Nucleic Acids Increase Hoogsteen-Face Affinity for a MicroRNA and Enhance Cellular Uptake
dc.year.issued2019

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