Synthesis and binding properties of perylene-oligo-2 '-deoxyribonucleotideconjugates

Perylene has been covalently linked, via polymethylene tethers. to the 5'- and the 3'-ends of an oligopyrimidine sequence. The presence of the polycyc lic ligand stabilizes the duplexes and the triplexes formed by the modified oligonucleotides and their single- and double-stranded DNA targets Lis com pared to those formed with the parent unmodified oligonucleotide used as re ference. Stabilization of the triplex is at its highest when perylene is li nked to the 5'-end of the oligonucleotide via a nine-atom size linker. Stab ilization of the duplexes is nearly equivalent whatever the position of the substitution (5' or 3') and the linker size used to tether both entities. (C) 2001 Elsevier Science Ltd. All rights reserved.