Biophysical and RNA interference inhibitory properties of oligonucleotides carrying tetrathiafulvalene groups at terminal positions

Oligonucleotide conjugates carrying a single functionalized tetrathiafulvalene (ttf) unit linked through a threoninol molecule to the 3′ or 5′ ends were synthesized together with their complementary oligonucleotides carrying a ttf,pyrene,or pentafluorophenyl group. ttf-oligonucleotide conjugates formed duplexes with higher thermal stability than the corresponding unmodified oligonucleotides and pyrene- and pentafluorophenyl-modified oligonucleotides. ttf-modified oligonucleotides are able to bind to citrate-stabilized gold nanoparticles (aunps) and produce stable gold aunps functionalized with oligonucleotides. finally,ttf- oligoribonucleotides have been synthesized to produce sirna duplexes carrying ttf units. the presence of the ttf molecule is compatible with the rna interference mechanism for gene inhibition. © 2013 sónia pérez-rentero et al.