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Synthesis and In vitro inhibition properties of oligonucleotide conjugates carrying amphipathic proline-rich peptide derivatives of the sweet arrow peptide (SAP)

AutorGrijalvo, Santiago; Eritja Casadellà, Ramón
Palabras claveAntisense oligonucleotides
DNA
Cellular uptake
Luciferase
Oligonucleotide- peptide conjugates
Phosphorothioate
Sweet arrow peptide
Fecha de publicaciónmay-2012
EditorSpringer
CitaciónMolecular Diversity
ResumenIn this study, a series of derivatives of the amphipathic proline-rich sweet arrow peptide (SAP) were covalently linked to antisense oligonucleotides designed to inhibit Renilla luciferase gene. Oligonucleotide-peptide conjugates carrying lysine (Lys) and ornithine (Orn) residues were prepared using the stepwise approach by assembling first the peptide sequence followed by the assembly of the DNA molecule. The resulting Lys, Orn-conjugates were transformed to the corresponding arginine and homoarginine oligonucleotide-peptide conjugates by reaction with O-methylisourea. The introduction of the SAP at 3'-termini of a phosphorothioate oligonucleotide did not affect the ability to inhibit gene expression when transfected with lipofectamine. However, these conjugates were not able to enter cells without transfecting agent. Further studies using SAP as a transfection agent showed promising results for the conjugates carrying the Orn-SAP. All conjugates showed high duplex stabilities.
Versión del editorDOI: 10.1007/s11030-012-9365-2
URIhttp://hdl.handle.net/10261/125223
DOI10.1007/s11030-012-9365-2
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