title: Design, synthesis and characterisation of guanosine-based amphiphiles.
abstract: A small library of sugar-modified guanosine derivatives has been prepared, starting from a common intermediate, fully protected on the nucleobase. Insertion of myristoyl chains and of diverse hydrophilic groups, such as an oligoethylene glycol, an amino acid or a disaccharide chain, connected through in vivo reversible ester linkages, or of a charged functional group provided different examples of amphiphilic guanosine analogues, named G1-G7 herein. All of the sugar-modified derivatives were positive in the potassium picrate test, showing an ability to form G-tetrads. CD spectra demonstrated that, as dilute solutions in CHCl(3), distinctive G-quadruplex systems may be formed, with spatial organisations dependent upon the structural modifications. Two compounds, G1 and G2, proved to be good low-molecular-weight organogelators in polar organic solvents, such as methanol, ethanol and acetonitrile. Ion transportation experiments through phospholipid bilayers were carried out to evaluate their ability to mediate H(+) transportation, with G5 showing the highest activity within the investigated series. Moreover, G3 and G5 exhibited a significant cytotoxic profile against human MCF-7 cancer cells in in vitro bioassays.
authors: Department of Organic Chemistry and Biochemistry, University Federico II of Napoli, Via Cintia, 4, 80126 Napoli, Italy.
authors: Luca
authors: L
authors: Simeone
authors: Domenico
authors: D
authors: Milano
authors: Lorenzo
authors: L
authors: De Napoli
authors: Carlo
authors: C
authors: Irace
authors: Antonio
authors: A
authors: Di Pascale
authors: Mariangela
authors: M
authors: Boccalon
authors: Paolo
authors: P
authors: Tecilla
authors: Daniela
authors: D
authors: Montesarchio
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D054856:G-Quadruplexes; D006151:Guanosine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology; D006801:Humans; D057927:Hydrophobic and Hydrophilic Interactions; D015394:Molecular Structure
chemical_list: D000970:Antineoplastic Agents; D006151:Guanosine