title: Synthesis, biological evaluation and supramolecular assembly of novel analogues of peptidyl nucleosides.
abstract: This work concerns the synthesis, the supramolecular assembly and the evaluation of some biological properties, such as DNA and RNA-binding ability and human serum stability, of novel nucleopeptides. These compounds are of potential interest for the well-known properties that similar compounds, such as natural peptidyl nucleosides, possess in biology and medicine and also for the possibility to realize nucleopeptide-based supramolecular systems useful for drug and gene delivery applications. More particularly, all four nucleobase-containing peptides were synthesized by solid phase synthesis, purified by HPLC and characterized by NMR and ESI-MS. Subsequently, nucleopeptide self-assembly as well as DNA and RNA-binding ability were investigated by CD spectroscopy and further information on the formation of molecular networks, based on the peptidyl nucleoside analogues and nucleic acids, was obtained by Laser Light Scattering. Finally, nucleopeptide enzymatic stability was studied and a half life of about 2 hours was found in the presence of 50% fresh human serum.
authors: Istituto di Biostrutture e Bioimmagini, CNR, Via Mezzocannone 16, 80134 Napoli, Italy. giroviel@unina.it
authors: Giovanni N
authors: GN
authors: Roviello
authors: Andrea
authors: A
authors: Ricci
authors: Enrico M
authors: EM
authors: Bucci
authors: Carlo
authors: C
authors: Pedone
mesh_terms: D000225:Adenine / Q000737:chemistry; D001667:Binding, Competitive; D002851:Chromatography, High Pressure Liquid; D002942:Circular Dichroism; D003596:Cytosine / Q000737:chemistry; D004247:DNA / Q000378:metabolism; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D015394:Molecular Structure; D009705:Nucleosides / Q000737:chemistry*; D020135:Peptide Nucleic Acids / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D010455:Peptides / Q000737:chemistry*; D012313:RNA / Q000378:metabolism; D044967:Serum / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization; D013056:Spectrophotometry, Ultraviolet; D013941:Thymine / Q000737:chemistry
chemical_list: D009705:Nucleosides; D020135:Peptide Nucleic Acids; D010455:Peptides; D012313:RNA; D003596:Cytosine; D004247:DNA; D000225:Adenine; D013941:Thymine