Journal article
Synthesis, surface properties, and biocompatibility of 1,2,3-triazole-containing alkyl β-d-xylopyranoside surfactants
Carbohydrate research, Vol.379, pp.68-77
09/20/2013
DOI: 10.1016/j.carres.2013.06.020
PMCID: PMC3764597
PMID: 23872788
Abstract
•Alkyl triazole xylopyranosides were synthesized from xylose using ‘click chemistry’.•Alkyl triazole xylopyranosides were moderately toxic to non-toxic in cells in culture.•Alkyl xylopyranosides with intermediate chain length caused apoptosis, not necrosis.•Long chain alkyl xylopyranosides form stable monolayers at the air–water interface.
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.
Details
- Title: Subtitle
- Synthesis, surface properties, and biocompatibility of 1,2,3-triazole-containing alkyl β-d-xylopyranoside surfactants
- Creators
- E. Davis Oldham - Department of Occupational and Environmental Health, The University of Iowa, UI Research Park, IREH, Iowa City, IA 52242-5000, USASrivenu Seelam - Department of Chemical and Materials Engineering, University of Kentucky, Lexington, KY 40506, USACarolina Lema - Department of Biological Sciences, Biosciences Research Building, University of Texas at El Paso, 500 West University Ave., El Paso, TX 79968, USARenato J Aguilera - Department of Biological Sciences, Biosciences Research Building, University of Texas at El Paso, 500 West University Ave., El Paso, TX 79968, USAJennifer Fiegel - Department of Pharmaceutical Sciences and Experimental Therapeutics, College of Pharmacy, University of Iowa, Iowa City, IA 52242,USAStephen E Rankin - Department of Chemical and Materials Engineering, University of Kentucky, Lexington, KY 40506, USABarbara L Knutson - Department of Chemical and Materials Engineering, University of Kentucky, Lexington, KY 40506, USAHans-Joachim Lehmler - Department of Occupational and Environmental Health, The University of Iowa, UI Research Park, IREH, Iowa City, IA 52242-5000, USA
- Resource Type
- Journal article
- Publication Details
- Carbohydrate research, Vol.379, pp.68-77
- DOI
- 10.1016/j.carres.2013.06.020
- PMID
- 23872788
- PMCID
- PMC3764597
- NLM abbreviation
- Carbohydr Res
- ISSN
- 0008-6215
- eISSN
- 1873-426X
- Publisher
- Elsevier Ltd
- Language
- English
- Date published
- 09/20/2013
- Academic Unit
- Occupational and Environmental Health; Iowa Neuroscience Institute; Pharmaceutical Sciences and Experimental Therapeutics; Chemical and Biochemical Engineering
- Record Identifier
- 9984000919302771
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