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Vinogradov, S ; Roig, V ; Sergueeva, Z ; Nguyen, CH ; Arimondo, P ; Thuong, NT ; Bisagni, E ; Sun, JS ; Helene, C ; Asseline, U

Synthesis and binding properties of oligo-2 ’-deoxyribonucleotides conjugated with triple-helix-specific intercalators : Benzo[e] and benzo(g] pyridoindoles

Bioconjugate Chemistry 14 (1) 120-135

par Administrateur - publié le

Abstract :

DNA binding compounds, such as benzo[e] (BePI) and benzo[g] pyridoindole (BgPI) derivatives, exhibit preferential stabilization of triple helices. We report here the synthesis of a series of pyrimidine triple-helix-forming oligo-2’-deoxyribonucleotides conjugated with these molecules. BePI was coupled to the 5-position of 2’-deoxyuridine via two linkers of different sizes attached to its 11-position and placed at either the 5’-end, inside the sequence, or at both the 5’-end and the internal positions using periodate oxidation of a diol-containing oligonucleotide followed by reductive coupling with amino-linked BePI. The same BePI derivatives were also linked to the oligonucleotide chain via internucleotidic phosphorothiolate or phosphoramidate linkages. A mixture of diastereoisomers was prepared as well as separate pure Rp and Sp isomers.