Hybridization properties of oligonucleotides bearing a tricyclic 2′-deoxycytidine analog based on a carbazole ring system

Abstract

A tricyclic carbazole-like 2′-deoxycytidine analog has been synthesized via a Stille biaryl coupling on 5-iodo-2′-deoxyuridine followed by cyclization. The carbazole nucleoside was incorporated in oligonucleotides (ONs) and shown to pair specifically with guanine. Duplexes resulting from the carbazole analog ONs and complementary RNA have elevated T ms especially when the carbazole nucleosides are clustered.