The solution synthesis of antisense oligonucleotide-peptide conjugates directly linked via phosphoramide bond by using a fragment coupling approach
| Autor: | Claude Malvy, Vassili A. Mandrugin, Marina Gottikh, Zsuzsa Majer, Jean Rémi Bertrand, Miklós Hollósi, Galina A. Korshunova, Alain Deroussent, Nataliya V. Sumbatyan |
|---|---|
| Rok vydání: | 2005 |
| Předmět: |
chemistry.chemical_classification
Reporter gene Molecular Structure Oligonucleotide Protein subunit Peptide General Medicine Oligonucleotides Antisense Antennapedia Biochemistry Combinatorial chemistry Amides Melittin Peptide Fragments Green fluorescent protein Solutions chemistry.chemical_compound chemistry Covalent bond Genetics Molecular Medicine Phosphoramides Phosphoric Acids Phosphorylation |
| Zdroj: | Nucleosides, nucleotidesnucleic acids. 23(12) |
| ISSN: | 1525-7770 |
| Popis: | To improve antisense oligonucleotide penetration inside cells, conjugates of oligonucleotides and cell-penetrating peptides, covalently linked through a phosphoramide bond, were prepared by a fragment coupling approach in the liquid phase. Two methods were used for this synthesis, i.e., phosphorylation of a peptide amino group by an oligonucleotide terminal phosphate 1-hydroxybenzotriazole ester in aqueous media or condensation of phosphate and amino groups in presence of triphenylphosphine, 2,2'-dithiopyridine and 4-dimethylaminopyridine in organic media. Several oligonucleotides, including a 18-mer antisense oligodeoxyribonucleotide complementary to an internal coding region of the reporter gene of the green fluorescent protein (GFP) were prepared. Peptides derived from the third helix of the homeodomain of Antennapedia, the influenza envelope hemagglutinin subunit as well as melittin and polymyxin B were used for the conjugates' synthesis. The peptides with various amino acid composition were chosen to confirm that these coupling methods are of a general use. |
| Databáze: | OpenAIRE |
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