Synthesis of water-soluble nucleotide-calixarene conjugates and preliminary investigation of their in vitro DNA replication inhibitory activity

Calix[4]arenes bearing four thymine or adenine 2′-deoxynucleotide moieties have been synthesized and characterized by NMR and ESI-MS analysis. Due to their amphiphilic nature, the conjugates (2a and 2b) obtained tend to self-assemble in aqueous medium by stacking interactions. Their good water solubility makes 2a and 2b promising candidates for bioorganic applications. A preliminary study has provided evidence of their inhibitory activity toward the replication of a Penicillium digitatum DNA fragment via PCR (polymerase chain reaction).