title: Chemoselective ligation in the functionalization of polysaccharide-based particles.
abstract: Despite the promise of precisely targeted or otherwise functionalized polymeric particulate drug delivery vehicles, typical biocompatible particles are generally not amenable to facile and selective surface modification. Herein, we report the development of a simple, mild, and chemoselective strategy for the conjugation of biologically active molecules to the surface of dextran-based microparticles. Alkoxyamine-bearing reagents were used to form stable oxime conjugates with latent aldehyde functionality present in reducing carbohydrate chain ends. We demonstrate the functionalization of dextran-based microparticles with a fluorophore as well as a cell-penetrating peptide sequence, which facilitated the delivery of cargo to nonphagocytic cells leading to a 60-fold increase in the expression of a reporter gene when plasmid DNA-loaded particles were used.
authors: Department of Chemistry, University of California, Berkeley, California 94720-1460, USA.
authors: Tristan T
authors: TT
authors: Beaudette
authors: Joel A
authors: JA
authors: Cohen
authors: Eric M
authors: EM
authors: Bachelder
authors: Kyle E
authors: KE
authors: Broaders
authors: Jessica L
authors: JL
authors: Cohen
authors: Edgar G
authors: EG
authors: Engleman
authors: Jean M J
authors: JM
authors: Fréchet
mesh_terms: D000080:Acetals / Q000737:chemistry; D000818:Animals; D002417:Cattle; D003911:Dextrans / Q000737:chemistry / Q000378:metabolism; D004337:Drug Carriers / Q000737:chemistry* / Q000378:metabolism; D006367:HeLa Cells; D006801:Humans; D053758:Nanoparticles / Q000737:chemistry; D011134:Polysaccharides / Q000737:chemistry* / Q000378:metabolism; D013379:Substrate Specificity; D013499:Surface Properties
chemical_list: D000080:Acetals; D003911:Dextrans; D004337:Drug Carriers; D011134:Polysaccharides