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 cellnuclei, exactly behaving as the NLS standard peptide.
A Peptide Nucleic Acid Embedding a Pseudopeptide Nuclear Localization Sequence in the Backbone Behaves as a Peptide Mimic / Sforza S.; Tedeschi T.; Calabretta A.; Corradini R.; Camerin C.; Tonelli R.; Pession A.; Marchelli R.. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - STAMPA. - 13:(2010), pp. 2441-2444. [10.1002/ejoc.201000123]
A Peptide Nucleic Acid Embedding a Pseudopeptide Nuclear Localization Sequence in the Backbone Behaves as a Peptide Mimic
CAMERIN, CONSUELO;TONELLI, ROBERTO;PESSION, ANDREA;
2010
Abstract
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 cellnuclei, exactly behaving as the NLS standard peptide.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.