Single-stranded and double-stranded oligonucleotides...

C - Chemistry – Metallurgy – 07 – H

Patent

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Details

C07H 21/00 (2006.01) A61K 31/7052 (2006.01) A61K 31/7064 (2006.01) A61K 31/7076 (2006.01) A61K 48/00 (2006.01) A61P 25/28 (2006.01) A61P 29/00 (2006.01) A61P 31/00 (2006.01) A61P 33/00 (2006.01) A61P 35/00 (2006.01)

Patent

CA 2562685

One aspect of the present invention relates to a double-stranded oligonucleotide comprising at least one aralkyl ligand. In certain embodiments, an aralkyl ligand is bound to only one of the two oligonucleotide strands comprising the double-stranded oligonucleotide. In certain embodiments, an aralkyl ligand is bound to both of the oligonucleotide strands comprising the double-stranded oligonucleotide. In certain embodiments, the oligonucleotide strands comprise at least one modified sugar moiety. In certain embodiments, at least one phosphate linkage in the oligonucleotide has been replaced with a phosphorothioate linkage. In a preferred embodiment, the aralkyl ligand is naproxen or ibuprofen. Another aspect of the present invention relates to a single-stranded oligonucleotide comprising at least one aralkyl ligand. In certain embodiments, the oligonucleotide comprises at least one modified sugar moiety. In certain embodiments, at least one phosphate linkage in the oligonucleotide has been replaced with a phosphorothioate linkage. In a preferred embodiment, the aralkyl ligand is naproxen or ibuprofen. The aralkyl ligand improves the pharmacokinetic properties of the oligonucleotide.

Selon un aspect, l'invention concerne un oligonucléotide double brin qui compren au moins un ligand aralkyle. Sous certaines variantes, un ligand aralkyle est lié à seulement l'un des deux brins d'oligonucléotide de l'oligonucléotide double brin. Sous certaines variantes, un ligand aralkyle est lié aux deux brins en question, ou encore les brins d'oligonucléotide comportent au moins une fraction sucre modifiée. Sous d'autres variantes encore, au moins une liaison phosphate dans l'oligonucléotide a été remplacée par une liaison phosphorothioate. En mode de réalisation préféré, le ligand aralkyle est naproxène ou ibuprofène. Un autre aspect concerne un oligonucléotide mon-brin qui comporte au moins un ligand aralkyle. Sous certains variantes, l'oligonucléotide comprend au moins une fraction sucre modifiée, ou encore au moins une liaison phosphate de l'oligonucléotide a été remplacée par une liaison phosphorothioate. En mode de réalisation préféré, le ligand aralkyle est naproxène ou ibuprofène. Le ligand aralkyle permet d'améliorer les propriétés pharmacocinétiques de l'oligonucléotide.

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