Synthesis and immobilization of a novel acridine derivative on microparticulate silica. A study of its interactions with single-stranded oligonucleotides by high-performance liquid chromatography

A novel approach for immobilizing acridine on 5-microns silica gel is described. The acridine moiety is functionalized with a carboxylic acid group at its reactive 9-position and activated, leading to 9-acridinylpropionic acid N-hydroxysuccinimide ester. This derivative is efficiently bound to the silica matrix through a primary aliphatic amine group at the end of a fifteen-atom spacer arm. The chromatographic properties of the final stationary phases, as evaluated with d(T)10 and d(A)10 at various pH values and organic solvent concentrations, resemble those of hydrophobic weak anion exchangers. When a secondary amine group is placed close to the acridine moiety in one of the packings, enhanced binding of the oligodeoxyribonucleotides is observed that goes beyond a purely additive effect