Carbohydrate derivatives and kits for cell surface labeling
AssigneeInstitute of Organic Chemistry and Biochemistry AS Cr, V. V. I.
InventorsMilan Vrabel, Rastislav Dzijak, Anna Kovalova
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Abstract
Carbohydrate derivatives of general formula I bearing a trans-cyclooctene moiety in covalently binding active moieties to cell surfaces in vitro and/or in vivo for therapeutic or nontherapeutic purposes are described. Compounds of general formula II are used together with the derivatives of general formula I in a method of binding active moieties to the cell surface. The compounds may be combined to form a kit for forming a covalent attachment of active moieties to the cell surface.
Claims10
A method for binding active moieties to a cell surface comprising the following steps:
- a) the cells are co-cultured with at least one carbohydrate derivative of general formula I
- wherein R1 is selected from H and C1-6 linear or branched alkyl,
- to form trans-cyclooctene presenting cells;
- b) at least one 1,2,4,5-tetrazine conjugate of general formula II
- wherein
- R2 is selected from:
- H, C1-10 alkyl, C6-10 aryl, 5-10-membered heteroaryl, C1-10 alkoxy, C6-10aryl-C1-10alkyl, 5-10-membered heteroaryl-C1-10 alkyl;
- linker is selected from C1-10 alkylene, C6-10 arylene, 5-10-membered heteroarylene, C6-10aryl-C1-10alkylene, 5-10-membered heteroaryl-C1-10alkylene, and polyethylene glycol;
- R3 is an active moiety selected from fluorophore, inhibitor, ligand, oligonucleotide, peptide, protein, enzyme, antibody, single-domain antibody, polymer, and nanoparticle;
- is brought into contact with the trans-cyclooctene presenting cells in order to covalently attach the active moiety to the cell surface.
A carbohydrate derivative of general formula I:
- wherein
- R1 is selected from H and C1-6 linear or branched alkyl.
Dependencies are inferred from the claim text.