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

Serguei Vinogradov, Victoria Roig, Zinaida Sergueeva, Chi Hung Nguyen, Paola Arimondo, Nguyen T. Thuong, Emile Bisagni, Jian Sheng Sun, Claude Hélène, Ulysse Asseline

Research output: Contribution to journalArticle

18 Citations (Scopus)

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 β-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.

Original languageEnglish (US)
Pages (from-to)120-135
Number of pages16
JournalBioconjugate Chemistry
Volume14
Issue number1
DOIs
StatePublished - Jan 1 2003

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Deoxyribonucleotides
Intercalating Agents
Oligonucleotides
Derivatives
Deoxyuridine
DNA
Absorption spectroscopy
Isomers
Deoxyribose
Stabilization
Oxidation
Molecules
3-methoxy-7H-8-methyl-11-((3'-amino)propylamino)benzo(e)pyrido(4,3-b)indole
Spectrum Analysis

ASJC Scopus subject areas

  • Biotechnology
  • Bioengineering
  • Biomedical Engineering
  • Pharmacology
  • Pharmaceutical Science
  • Organic Chemistry

Cite this

Synthesis and binding properties of oligo-2′-deoxyribonucleotides conjugated with triple-helix-specific intercalators : Benzo[e] and benzo[g] pyridoindoles. / Vinogradov, Serguei; Roig, Victoria; Sergueeva, Zinaida; Nguyen, Chi Hung; Arimondo, Paola; Thuong, Nguyen T.; Bisagni, Emile; Sun, Jian Sheng; Hélène, Claude; Asseline, Ulysse.

In: Bioconjugate Chemistry, Vol. 14, No. 1, 01.01.2003, p. 120-135.

Research output: Contribution to journalArticle

Vinogradov, S, Roig, V, Sergueeva, Z, Nguyen, CH, Arimondo, P, Thuong, NT, Bisagni, E, Sun, JS, Hélène, C & Asseline, U 2003, 'Synthesis and binding properties of oligo-2′-deoxyribonucleotides conjugated with triple-helix-specific intercalators: Benzo[e] and benzo[g] pyridoindoles', Bioconjugate Chemistry, vol. 14, no. 1, pp. 120-135. https://doi.org/10.1021/bc020038w
Vinogradov, Serguei ; Roig, Victoria ; Sergueeva, Zinaida ; Nguyen, Chi Hung ; Arimondo, Paola ; Thuong, Nguyen T. ; Bisagni, Emile ; Sun, Jian Sheng ; Hélène, Claude ; Asseline, Ulysse. / Synthesis and binding properties of oligo-2′-deoxyribonucleotides conjugated with triple-helix-specific intercalators : Benzo[e] and benzo[g] pyridoindoles. In: Bioconjugate Chemistry. 2003 ; Vol. 14, No. 1. pp. 120-135.
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