European Journal of Organic Chemistry p. 2441 - 2444 (2010)
Update date:2022-08-02
Topics:
Sforza, Stefano
Tedeschi, Tullia
Calabretta, Alessandro
Corradini, Roberto
Camerin, Consuelo
Tonelli, Roberto
Pession, Andrea
Marchelli, Rosangela
In this paper, the synthesis of a short modified peptide nucleic acid (PNA), obtained by using several different L-amino acids as synthons, is shown. The synthesis was performed by a submonomeric strategy, obtaining a model trimeric PNA containing embedded amino acid derived side chains in its backbone that mimic the peptide sequence PKKKRKV, which is a nuclear localization signal (NLS) widely used for translocating cargo molecules into cell nuclei. Fluorescence experiments demonstrated that this modified PNA, and not a standard unmodified PNA having the same nucleobase sequence, was able to penetrate Rhabdomyosarcoma cell nuclei, exactly behaving as the NLS standard peptide.
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