A1 Refereed original research article in a scientific journal
gamma-(S)-Guanidinylmethyl-Modified Triplex-Forming Peptide Nucleic Acids Increase Hoogsteen-Face Affinity for a MicroRNA and Enhance Cellular Uptake
Authors: Tähtinen V, Verhassel A, Tuomela J, Virta P
Publisher: WILEY-V C H VERLAG GMBH
Publishing place: WEINHEIM
Publication year: 2019
Journal: ChemBioChem
Journal name in source: CHEMBIOCHEM
Journal acronym: CHEMBIOCHEM
Volume: 20
Issue: 24
First page : 3041
Last page: 3051
Number of pages: 12
ISSN: 1439-4227
eISSN: 1439-4227
DOI: https://doi.org/10.1002/cbic.201900393
Self-archived copy’s web address: https://research.utu.fi/converis/portal/detail/Publication/42614349
gamma-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.
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