Lipophilic oligonucleotide analogs

Details Lipophilic oligonucleotide analogs Lipophilic oligonucleotide analogs

C - Chemistry, Metallurgy

07

H

C07H 21/00 (2006.01) A61K 31/70 (2006.01) A61K 48/00 (2006.01) A61K 49/00 (2006.01) C07F 9/6512 (2006.01) C07F 9/6561 (2006.01) C09B 57/00 (2006.01) C12N 15/87 (2006.01) C12Q 1/68 (2006.01)

Patent

CA 2261704

The invention discloses lipophilic oligonucleotide analogs that are capable of efficient passive diffusion across cell membranes. These oligonucleotides contain at least two nucleotide residues and have an octanol:water partition coefficient of about -0.3 to + 2.5 and a solubility in water of at least 0.001 µg/mL. Invention embodiments which include lipophilic oligonucleotide analogs having either at least 60 % of the internucleotide linkages are lipophilic, or at least 60 % of the bases contain lipophilic substitutions, or at least 60 % of the sugars contain lipophilic substitutions, or a combination of these sums to 60 %. These oligonucleotides may be conjugated to a label and used to visualize cells or subcellular compartments.

Analogues lipophiles d'oligonucléotides capables de se diffuser passivement et efficacement à travers les membranes cellulaires. Ces oligonucléotides contiennent au moins deux résidus de nucléotides et ont un coefficient de partage octanol:eau allant de -0,3 à +2,5 environ et une solubilité dans l'eau d'au moins 0,001 µg/mL. L'invention porte notamment sur des analogues lipophiles d'oligonucléotides dont au moins 60 % des liaisons inter-nucléotides sont lipophiles, ou dont au moins 60 % des bases contiennent des substitutions lipophiles, ou dont au moins 60 % des glucides contiennent des substitutions lipophiles, ou qui présentent une combinaison de ceux-ci à raison de 60 %. Ces oligonucléotides peuvent être conjugués pour former un marqueur et utilisés pour visualiser des cellules ou des compartiments infracellulaires.

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