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 unstable monolayer was observed.

The cytotoxic effect of 2-acylated-1,4-naphthohydroquinones on leukemia/lymphoma cells

“…The colored formazan product was measured by absorbance at 490 nm with a reference wavelength of 650 nm using a microplate reader (SPECTRA MAX 190, Molecular Devices, Sunnyvale, CA). 33 Control wells containing the same volumes of culture medium and-MTS reagent without cells were utilized to subtract background absorbance. Additionally, cells treated with 1 mM of hydrogen peroxide (H 2 O 2 ; Sigma–Aldrich, St. Louis, MO) were used as positive controls for cytotoxicity.…”

Synthesis of environment friendly nonionic surfactants from sugar base and characterization of interfacial properties for detergent application

“…In this study, foam stability for 1 wt% surfactant solution was studied by measuring a half-life, which corresponds to the time required for initial foam volume to decrease by 50 percent. The stability of aqueous surfactant solutions was determined by conductometric measurement (DualCon TM III, ITEC) at 25 8C [11,12]. By measuring the voltage potential at the upper fill height and at the bottom of the sample 100 h after preparation of the sample, the changes in structure of aqueous dispersions as well as coalescence, aggregation or creaming phenomena were determined.…”

“…Nonionic surfactants generally exhibit a very low toxicity level and are also used as cleaners, wetting agents and emulsifiers in pharmaceuticals, cosmetics and food products. One of the major issues in surfactant and detergent industry is growing environmental concern such as biodegradability and mildness of surfactant, pollution control in manufacturing processes, and consumer desire for effective and eco-friendly green products [2][3][4][5][6][7][8][9][10][11][12][13][14][15][16].…”

Synthesis and Properties of Alkoxyethyl β‐d‐Xylopyranoside

“…The hydrophobic hydrocarbon tail group is usually composed of different chain lengths of saturated, fluorinated, or unsaturated alcohol (Chen, Li, et al, ; Xu et al, ). The most readily available monosaccharide raw materials are glucose and xylose (Oldham et al, ). For some time, sugar‐based surfactants have been prepared by glycochemical methods with glucose (anhydrous or monohydrate), dextrose, and starch as the starting materials (El‐Sukkary, Syed, Aiad, & El‐Azab, ; Rather & Mishra, ; Turner, Svensson, Adlercreutz, & Karlsson, ; von Rybinski & Hill, ; Weuthen, Kawa, Hill, & Ansmann, ).…”