Premium
A Peptide Nucleic Acid Embedding a Pseudopeptide Nuclear Localization Sequence in the Backbone Behaves as a Peptide Mimic
Author(s) -
Sforza Stefano,
Tedeschi Tullia,
Calabretta Alessandro,
Corradini Roberto,
Camerin Consuelo,
Tonelli Roberto,
Pession Andrea,
Marchelli Rosangela
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000123
Subject(s) - chemistry , peptide nucleic acid , peptide , nucleic acid , sequence (biology) , peptide sequence , nucleobase , amino acid , nuclear localization sequence , combinatorial chemistry , stereochemistry , biochemistry , dna , cytoplasm , gene
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.