title: Microwave-assisted syntheses of BODIPY-sugar conjugates through click chemistry and conjugate assembly into liposomes.
abstract: BODIPY fluorophores bearing azide or terminal alkyne functions were conjugated with glycans modified with terminal alkyne or azido through the Cu(I)-catalyzed 1,3-dipolar azide-alkyne cycloaddition (CuAAC) chemistry under microwave heating while these reactions did not proceed when heated in an oil-bath. The BODIPY-glycan conjugate product 8a undergoes self-assembly into liposomes when hydrated. Formation of liposomes was confirmed by both bright field and confocal microscopy. Fluorescent emission within the liposome was shifted from green to red due to effective high concentrations.
authors.affiliation: Department of Chemistry, Brock University, 500 Glenridge Ave., St. Catharines, Ontario, Canada L2S 3A1.
authors.forename: Ravi Shekar
authors.initials: RS
authors.lastname: Yalagala
authors.affiliation: Department of Chemistry, Brock University, 500 Glenridge Ave., St. Catharines, Ontario, Canada L2S 3A1.
authors.forename: Sina Atrin
authors.initials: SA
authors.lastname: Mazinani
authors.affiliation: Department of Biological Sciences, Brock University, 500 Glenridge Ave., St. Catharines, Ontario, Canada L2S 3A1.
authors.forename: Lucas A
authors.initials: LA
authors.lastname: Maddalena
authors.affiliation: Department of Biological Sciences, Brock University, 500 Glenridge Ave., St. Catharines, Ontario, Canada L2S 3A1.
authors.forename: Jeffrey A
authors.initials: JA
authors.lastname: Stuart
authors.affiliation: Sussex Research Laboratories Inc., 100 Sussex Drive, Ottawa, Ontario, Canada K1A 0R6.
authors.forename: Fengyang
authors.initials: F
authors.lastname: Yan
authors.affiliation: Department of Chemistry, Brock University, 500 Glenridge Ave., St. Catharines, Ontario, Canada L2S 3A1. Electronic address: tyan@brocku.ca.
authors.forename: Hongbin
authors.initials: H
authors.lastname: Yan
mesh_terms: D001896:Boron Compounds / Q000737:chemistry*; D057930:Click Chemistry; D008081:Liposomes / Q000737:chemistry / Q000648:ultrastructure*; D018613:Microscopy, Confocal; D011134:Polysaccharides / Q000737:chemistry*
chemical_list: C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D001896:Boron Compounds; D008081:Liposomes; D011134:Polysaccharides
keywords: BODIPY; CuAAC click chemistry; Fluorophore; Liposome; Microwave assisted synthesis