US 12,492,426 B2
Oligonucleotide-functionalized hydrophobic polymer nanoparticles
Andrey Klymchenko, Illkirch (FR); Nina Melnychuk, Illkirch (FR); and Andreas Reisch, Colmar (FR)
Filed by UNIVERSITE DE STRASBOURG, Strasbourg (FR); and CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE, Paris (FR)
Filed on May 30, 2023, as Appl. No. 18/325,409.
Application 18/325,409 is a division of application No. 16/979,309, granted, now 11,697,838, previously published as PCT/EP2019/055847, filed on Mar. 8, 2019.
Claims priority of application No. 18305253 (EP), filed on Mar. 9, 2018.
Prior Publication US 2023/0399681 A1, Dec. 14, 2023
Int. Cl. C12Q 1/68 (2018.01); C12Q 1/6818 (2018.01); B82Y 5/00 (2011.01)
CPC C12Q 1/6818 (2013.01) [B82Y 5/00 (2013.01); C12Q 2525/197 (2013.01); C12Q 2537/161 (2013.01); C12Q 2563/107 (2013.01); C12Q 2563/155 (2013.01)] 12 Claims
OG exemplary drawing
 
1. An oligonucleotide-functionalized hydrophobic polymer nanoparticle, said nanoparticle being a hydrophobic polymeric nanoparticle, comprising:
a hydrophobic polymer chain, said chain bearing at least one moiety of formula (I′),

OG Complex Work Unit Chemistry
wherein:
A represents a spacer chosen from: —(CH2)m—, —(CH2)pNH—CO(CH2)q—, —(CH2)pCO—NH(CH2)q—, —(CH2)PO(CH2)q—, —(CH2)pNH(CH2)qO—, —(CH2)mCO—, or —CO(CH2)m—, each of m, p and q represent, independently from each other, an integer chosen from 0 to 8,
D represents a group chosen from:

OG Complex Work Unit Chemistry
wherein R′ represents a hydrogen, a halogen, or a (C1-C8) alkyl,
a cyclo(C3-C7) alkyl, a cyclo (C3-C7) alkyl monosubstituted, a monocyclic non-aromatic heterocyclic group, a monocyclic non-aromatic heterocyclic group monosubstituted, a monocyclic aromatic group, or a monocyclic aromatic group monosubstituted,
E represents YNRa, where Ra is H or an (C1-C8) alkyl,
X, Y, Z are identical or different and each represent independently of the other a spacer chosen from —(CH2)r—, —(CH2—CH2—O)r—, —(CH2—CH2—NH)r—, —(CH2)sNH—CO(CH2)t—, or —(CH2)sCO—NH(CH2)t—, r, s and t represent independently from each other an integer chosen from 0 to 8,
R1 is selected from the group consisting of:
—COOH,
—PO(OH)2, —PO(ORb)OH, —O—PO(OH)2, —O—PO(ORb)OH, where Rb is methyl or ethyl,
—S(═O)2—OH, and —OS(═O)2OH,
n represents an integer chosen from 1 to 10,
when D represents

OG Complex Work Unit Chemistry
E can be absent;
said moiety of formula (I′) being bound to a carboxyl group of the hydrophobic polymer chain and being positioned on the surface of the nanoparticle, and
wherein at least some of any azide groups present, are transformable into triazole groups or derivatives thereof and functionalizable by:
(a) target-specific oligonucleotides,
(b) non-specific oligonucleotides, or
(c) any combination thereof.