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Synthesis, surface properties, and biocompatibility of 1,2,3-triazole-containing alkyl β-d-xylopyranoside surfactants

Oldham, E. Davis, Seelam, Srivenu, Lema, Carolina, Aguilera, Renato J., Fiegel, Jennifer, Rankin, Stephen E., Knutson, Barbara L., Lehmler, Hans-Joachim
Carbohydrate research 2013 v.379 pp. 68-77
alkynes, apoptosis, azides, biocompatibility, biomass, detergents, differential scanning calorimetry, drugs, mammals, personal care products, surfactants, temperature, toxicity, xylose
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 1000μM. Triazole-containing β-xylopyranosides with 8, 10, or 12 carbons caused toxicity via apoptosis, with CC₅₀ values ranging from 26–890μM. 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.