Journal
CHEMBIOCHEM
Volume 20, Issue 24, Pages 3041-3051Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cbic.201900393
Keywords
F-19 NMR spectroscopy; cellular uptake; RNA triple helices; peptide nucleic acids
Funding
- Biocenter Finland
- Academy of Finland [308931]
- Academy of Finland (AKA) [308931, 308931] Funding Source: Academy of Finland (AKA)
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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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