title: Modifying the glycosidic linkage in digitoxin analogs provides selective cytotoxins.
abstract: A chemoselective reaction between oxyamines and unprotected, unactivated reducing sugars was used to construct for the first time a panel of linkage-diversified neoglycosides. This panel of digitoxin analogs included potent and selective tumor cytotoxins; cytotoxicity was dependent on the structure of the glycosidic linkage. These results validate linkage diversification through neoglycosylation as a unique and simple strategy to powerfully complement existing methods for the optimization of glycoconjugates.
authors.affiliation: Department of Chemistry, Seattle University, 901 12th Avenue, Seattle, WA 98122, USA. langenha@seattleu.edu
authors.forename: Joseph M
authors.initials: JM
authors.lastname: Langenhan
authors.forename: Jeffery M
authors.initials: JM
authors.lastname: Engle
authors.forename: Lauren K
authors.initials: LK
authors.lastname: Slevin
authors.forename: Lindsay R
authors.initials: LR
authors.lastname: Fay
authors.forename: Ryan W
authors.initials: RW
authors.lastname: Lucker
authors.forename: Kyle R
authors.initials: KR
authors.lastname: Smith
authors.forename: Matthew M
authors.initials: MM
authors.lastname: Endo
mesh_terms: D000588:Amines / Q000737:chemistry; D002241:Carbohydrates / Q000737:chemistry; D003603:Cytotoxins / Q000737:chemistry / Q000494:pharmacology*; D004074:Digitoxin / Q000031:analogs & derivatives* / Q000737:chemistry; D006001:Glycoconjugates / Q000737:chemistry; D006031:Glycosylation
chemical_list: D000588:Amines; D002241:Carbohydrates; D003603:Cytotoxins; D006001:Glycoconjugates; D004074:Digitoxin