title: Synthesis, surface properties, and biocompatibility of 1,2,3-triazole-containing alkyl β-D-xylopyranoside surfactants.
abstract: We are interested in the development of surfactants derived from hemicellulosic biomass, as they are potential components in pharmaceuticals, personal care products, and other detergents. Such surfactants should exhibit low toxicity in mammalian cells. In this study we synthesized a series of alkyl or fluoroalkyl β-xylopyranosides from azides and an alkyne using the copper-catalyzed azide-alkyne (CuAAC) 'click' reaction in 4 steps from xylose. The purified products were evaluated for both their surfactant properties, and for their biocompatibility. Unlike other carbohydrate-based surfactants, liquid-crystalline behavior was not observed by differential scanning calorimetry. The triazole-containing β-xylopyranosides with short (6 carbons) and long (>12 carbons) chains exhibited no toxicity at concentrations ranging from 1 to 1000 μM. Triazole-containing β-xylopyranosides with 8, 10, or 12 carbons caused toxicity via apoptosis, with CC50 values ranging from 26-890 μM. The two longest chain compounds did form stable monolayers at the air-water interface over a range of temperatures, although a brief transition to an the unstable monolayer was observed.
authors.affiliation: Department of Occupational and Environmental Health, The University of Iowa, UI Research Park, IREH, Iowa City, IA 52242-5000, USA.
authors.forename: E Davis
authors.initials: ED
authors.lastname: Oldham
authors.forename: Srivenu
authors.initials: S
authors.lastname: Seelam
authors.forename: Carolina
authors.initials: C
authors.lastname: Lema
authors.forename: Renato J
authors.initials: RJ
authors.lastname: Aguilera
authors.forename: Jennifer
authors.initials: J
authors.lastname: Fiegel
authors.forename: Stephen E
authors.initials: SE
authors.lastname: Rankin
authors.forename: Barbara L
authors.initials: BL
authors.lastname: Knutson
authors.forename: Hans-Joachim
authors.initials: HJ
authors.lastname: Lehmler
mesh_terms: D017209:Apoptosis / Q000187:drug effects; D001672:Biocompatible Materials / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002470:Cell Survival / Q000187:drug effects; D002478:Cells, Cultured; D004305:Dose-Response Relationship, Drug; D006801:Humans; D019169:Jurkat Cells; D013329:Structure-Activity Relationship; D013499:Surface Properties; D013501:Surface-Active Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013696:Temperature; D014230:Triazoles / Q000737:chemistry*; D014994:Xylose / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D001672:Biocompatible Materials; D013501:Surface-Active Agents; D014230:Triazoles; C431715:xylopyranose; D014994:Xylose
keywords: Carbohydrate surfactants; Click chemistry; Cytotoxicity; Huisgen cycloaddition; Langmuir monolayers