Cationic oligonucleotides, automated methods for preparing...

Details Cationic oligonucleotides, automated methods for preparing... Cationic oligonucleotides, automated methods for preparing...

C - Chemistry, Metallurgy

07

H

C07H 21/00 (2006.01)

Patent

CA 2633065

The invention relates to oligonucleotide-oligocation molecules A i B j H that can be synthetized via automated phos-phoramidite chemistry having oligonucleotides moieties Ai and oligocations moieties Bj, wherein . A i is an i-mer oligonucleotide residue, with i = 5 to 50, where nucleotide A is an oligomer with naturally or non naturally occurring nucleobases and/or pentafu-ranosyl groups and/or native phosphodiester bonds, for example selected from the group comprising deoxyribo, ribo, locked (LNA) nucleotides as well as their chemical modifications or substitutions such as phosphorothioate, 2'-fluoro, 2'-O-alkyl, or a marker group such as a fluorescent agent, . Bj is a j-mer organic oligocation moiety, with j = 1 to 50, where B is selected from the group comprising .cndot. - HPO3-R1 -(X-R2n)n1-X-R3-O-, where R1, R2n and R3, identical or different, are lower alkylene, X is NH or NC(NH2)2, n varies from 1 to 5 and n1 = 2 to 20, .cndot. - HPO3-R4-CH(R5X1)-R6-O-, where R4 is lower alkylene, R5 and R6, identical or different, are lower alkylene and X1 is putrescine, spermidine or spermine residue, .cndot. - HPO3- R7-(aa)n2-R8-O-, where R7 is lower alkylene and R8 is lower alkylene, serine, a natural aminoalcohol, (aa)n2 is a peptide containing natural aminoacids with cationic side chains, such as Arginine, Lysine, Ornithine, - Histidine, Diaminopropionic acid and n2= 2 to 20.

L'invention concerne des molécules de type oligonucléotide-oligocation A<SUB>i</SUB>B<SUB>j</SUB>H qui peuvent être synthétisées via une chimie au phosphoramidite automatisée ayant des entités oligonucléotides A<SUB>i</SUB> et des entités oligocations B<SUB>j</SUB> : A<SUB>i</SUB> étant un résidu d'oligonucléotide i-mère, i étant = 5 à 50, où le nucléotide A est un oligomère ayant des nucléobases présentes dans la nature ou non et/ou des groupes pentafuranosyles et/ou des liaisons phosphodiesters natives, par exemple sélectionné dans le groupe comprenant des désoxyribonucléotides, des ribonucléotides, des nucléotides verrouillés (LNA) ainsi que leurs modifications chimiques ou substitutions telles que par un phosphorothioate, un 2'-fluoro, un 2'-O-alkyle ou un groupe marqueur tel qu'un agent fluorescent ; B<SUB>j</SUB> étant une entité oligocation organique j-mère, j étant = 1 à 50, où B est sélectionné dans le groupe comprenant . - HPO<SUB>3</SUB>-R<SUP>1</SUP> -(X-R<SUP>2</SUP> <SUB>n</SUB>)

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