title: Synthesis of bivalent lactosides and their activity as sensors for differences between lectins in inter- and intrafamily comparisons.
abstract: The synthesis of nine bivalent lactosides (based on ditriazoles, diamides, a glycocyclophane and an acyclic analogue of the glycocyclophane) and one monovalent lactosyl triazole facilitated the assessment of the sensitivity of plant/animal lectins to this type of ligand display. The inhibitory potency of the compounds was determined in two assays of increasing biorelevance. These were solid-phase and cell binding set-ups. Hereby, the ability of the compounds to inhibit the binding of two plant agglutinins and the entire set of adhesion/growth-regulatory galectins from one organism (chicken) to a glycoprotein or to cell surfaces was systematically evaluated. Differential sensitivities were detected between plant and animal lectins and also between distinct galectin forms within the chicken series. Two of the bivalent probes can be considered as sensors for interlectin differences. Most pronounced were the selectivities of N-glycosyl 1,2,3-triazole derivatives for the chimera-type galectin and its proteolytically truncated version.
authors.affiliation: Institute of Physiological Chemistry, Faculty of Veterinary Medicine, Ludwig-Maximilians-University Munich, Veterinärstr. 13, 80539 Munich, Germany.
authors.forename: Sabine
authors.initials: S
authors.lastname: André
authors.forename: Dilip V
authors.initials: DV
authors.lastname: Jarikote
authors.forename: Dandan
authors.initials: D
authors.lastname: Yan
authors.forename: Lisa
authors.initials: L
authors.lastname: Vincenz
authors.forename: Guan-Nan
authors.initials: GN
authors.lastname: Wang
authors.forename: Herbert
authors.initials: H
authors.lastname: Kaltner
authors.forename: Paul V
authors.initials: PV
authors.lastname: Murphy
authors.forename: Hans-Joachim
authors.initials: HJ
authors.lastname: Gabius
mesh_terms: D000373:Agglutinins / Q000737:chemistry; D000818:Animals; D001665:Binding Sites; D002462:Cell Membrane / Q000737:chemistry; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D002645:Chickens; D004305:Dose-Response Relationship, Drug; D015195:Drug Design; D037161:Galectins / Q000737:chemistry; D006023:Glycoproteins / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry*; D007700:Kinetics; D037102:Lectins / Q000737:chemistry*; D008024:Ligands; D008956:Models, Chemical; D037121:Plant Lectins / Q000737:chemistry; D012680:Sensitivity and Specificity; D014230:Triazoles / Q000737:chemistry
chemical_list: D000373:Agglutinins; D037161:Galectins; D006023:Glycoproteins; D006027:Glycosides; D037102:Lectins; D008024:Ligands; D037121:Plant Lectins; D014230:Triazoles; C008245:lactosides