title: Vitamin B12 Suitably Tailored for Disulfide-Based Conjugation.
abstract: Vitamin B12 has been proposed to be a natural vector for the in vivo delivery of biologically active compounds. Most synthetic methodologies leading to vitamin B12 conjugates involve functionalization at the 5' position via either carbamate-based linkages or using copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC), resulting in stable conjugates that are not cleaved within the cell. We have developed a novel vitamin B12 derivative suitably tailored for disulfide-based conjugation that can undergo cleavage in the presence of glutathione, the most abundant thiol in mammalian cells. This active compound is simple to prepare and allows for the direct disulfide-based attachment of therapeutic cargos.
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences , M. Kasprzaka 44/52, 01-224 Warsaw, Poland.
authors.forename: Aleksandra
authors.initials: A
authors.lastname: Wierzba
authors.affiliation: Centre of New Technologies, University of Warsaw , S. Banacha 2c, 02-097 Warsaw, Poland.
authors.forename: Monika
authors.initials: M
authors.lastname: Wojciechowska
authors.affiliation: Centre of New Technologies, University of Warsaw , S. Banacha 2c, 02-097 Warsaw, Poland.
authors.forename: Joanna
authors.initials: J
authors.lastname: Trylska
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences , M. Kasprzaka 44/52, 01-224 Warsaw, Poland.
authors.forename: Dorota
authors.initials: D
authors.lastname: Gryko
mesh_terms: D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D003300:Copper; D061565:Cycloaddition Reaction; D004220:Disulfides / Q000737:chemistry*; D004337:Drug Carriers / Q000737:chemistry; D010455:Peptides / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000737:chemistry; D014805:Vitamin B 12 / Q000737:chemistry*
chemical_list: D004220:Disulfides; D004337:Drug Carriers; D010455:Peptides; D013438:Sulfhydryl Compounds; D003300:Copper; D014805:Vitamin B 12