title: Synthesis and binding properties of oligo-2'-deoxyribonucleotides conjugated with triple-helix-specific intercalators: benzo[e] and benzo[g] pyridoindoles.
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. A BePI derivative, with two different linkers attached to its 3-position, and BgPI derivatives were also linked to the 5-position of a 2'-deoxyuridine located at either the 5'-end or inside the sequence, as well as to the beta- anomeric position of an additional 2'- deoxyribose placed inside the sequence. The binding properties of these oligonucleotide-benzopyridoindoles conjugates with their double-stranded DNA target was studied by absorption spectroscopy.
authors.affiliation: Centre de Biophysique Moléculaire, CNRS UPR 4301, Rue Charles Sadron, 45071 Orléans Cedex 02, France.
authors.forename: Serguei
authors.initials: S
authors.lastname: Vinogradov
authors.forename: Victoria
authors.initials: V
authors.lastname: Roig
authors.forename: Zinaida
authors.initials: Z
authors.lastname: Sergueeva
authors.forename: Chi Hung
authors.initials: CH
authors.lastname: Nguyen
authors.forename: Paola
authors.initials: P
authors.lastname: Arimondo
authors.forename: Nguyen T
authors.initials: NT
authors.lastname: Thuong
authors.forename: Emile
authors.initials: E
authors.lastname: Bisagni
authors.forename: Jian-Sheng
authors.initials: JS
authors.lastname: Sun
authors.forename: Claude
authors.initials: C
authors.lastname: Hélène
authors.forename: Ulysse
authors.initials: U
authors.lastname: Asseline
mesh_terms: D001483:Base Sequence; D003432:Cross-Linking Reagents; D004247:DNA; D007211:Indoles / Q000737:chemistry*; D007364:Intercalating Agents / Q000138:chemical synthesis* / Q000737:chemistry; D009690:Nucleic Acid Conformation; D009693:Nucleic Acid Hybridization; D020319:Oligodeoxyribonucleotides, Antisense / Q000138:chemical synthesis* / Q000737:chemistry; D013053:Spectrophotometry; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D003432:Cross-Linking Reagents; D007211:Indoles; D007364:Intercalating Agents; D020319:Oligodeoxyribonucleotides, Antisense; C051802:triplex DNA; D004247:DNA