Physico-chemical properties and cytotoxic effects of sugar-based surfactants: Impact of structural variations

Lu, Biao; Vayssade, Muriel; Miao, Yong; Chagnault, Vincent; Grand, Éric; Wadouachi, Anne; Postel, Denis; Drelich, Audrey; Egles, Christophe; Pezron, Isabelle

doi:10.1016/j.colsurfb.2016.04.044

Cited by 34 publications

(18 citation statements)

References 31 publications

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“…The cytotoxicity of the selected sugar fatty acids (glucose C10, mannose C10, lactose C10 and lactose biphenylacetate) was evaluated by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay on Caco-2 cells (Figure 2). As known, the cytotoxic effect results from the interplay of different factors such as the ability of the hydrocarbon chain to insert into the lipid bilayer [44].…”

Section: Mtt Toxicity Assaymentioning

confidence: 99%

Synthesis and Evaluation of Saccharide-Based Aliphatic and Aromatic Esters as Antimicrobial and Antibiofilm Agents

et al. 2019

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A small library of sugar-based (i.e., glucose, mannose and lactose) monoesters containing hydrophobic aliphatic or aromatic tails were synthesized and tested. The antimicrobial activity of the compounds against a target panel of Gram-positive, Gram-negative and fungi was assessed. Based on this preliminary screening, the antibiofilm activity of the most promising molecules was evaluated at different development times of selected food-borne pathogens (E. coli, L. monocytogenes, S. aureus, S. enteritidis). The antibiofilm activity during biofilm formation resulted in the following: mannose C10 > lactose biphenylacetate > glucose C10 > lactose C10. Among them, mannose C10 and lactose biphenylacetate showed an inhibition for E. coli 97% and 92%, respectively. At MICs values, no toxicity was observed on Caco-2 cell line for all the examined compounds. Overall, based on these results, all the sugar-based monoesters showed an interesting profile as safe antimicrobial agents. In particular, mannose C10 and lactose biphenylacetate are the most promising as possible biocompatible and safe preservatives for pharmaceutical and food applications.

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Section: Mtt Toxicity Assaymentioning

confidence: 99%

Synthesis and Evaluation of Saccharide-Based Aliphatic and Aromatic Esters as Antimicrobial and Antibiofilm Agents

et al. 2019

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“…Indeed, to comply with REACH regulation 19 , lipophilicity of substances has to be characterized by the octanol-water partition coefficient, and for surfactants, this partition coefficient has to be measured below CMC 20 . At last, recent works highlighted potential trends between the CMC and the cytotoxicity of sugar-based surfactants 21 .…”

Section: Introductionmentioning

confidence: 99%

New QSPR Models to Predict the Critical Micelle Concentration of Sugar-Based Surfactants

Gaudin

Rotureau

Pezron

et al. 2016

Ind. Eng. Chem. Res.

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Sugar-based surfactants represent a fruitful field of research in the context of sustainable chemistry since they can be obtained from renewable resources. In this work, new Quantitative Structure Property Relationships (QSPR) models for the critical micelle concentration (CMC) dedicated to sugar-based surfactants are proposed in order to reduce testing in a screening perspective. An important literature compilation allowed the constitution of a dataset of 83 sugar-based surfactants for which accurate CMC values were found. Then, a series of QSPR models were developed based on molecular descriptors of the whole molecule, and of the hydrophobic and hydrophilic fragments taken separately. Different models were considered by including quantum-chemical descriptors with hope to access physically based models, and by using only simple constitutional descriptors to favor fast and easy prediction. The best QSPR model was obtained including quantum-chemical descriptors of the whole molecular structure with a root mean square error (RMSE) of 0.32 (log) evaluated on a validation set of 27 molecules. A simpler model with good performances was also found (with a RMSE of 0.36 (log) on the validation set), including only constitutional-based fragment descriptors, that can be easily computed from the 2-dimension structure of the hydrophilic and hydrophobic fragments.

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“…[51] tested a different group of sugar-based surfactants, glucuronamides, and observed for octyl and dodecyl derivatives the CMC at 3.3 mM ( γ CMC = 24.4 mN m −1 ) and 0.7 mM ( γ CMC = 22.1 mN m −1 ) respectively. To illustrate, the CMC values for commercial surfactants are as followed: 0.08 mM for Tween ® 20 [52], 20 mM for Hecameg ® [52], 8.35 mM for sodium dodecyl sulfate [53], 15 mM for dodecyltrimethylammonium bromide [50]. …”

Section: Resultsmentioning

confidence: 99%

Alkyl Xylosides: Physico‐Chemical Properties and Influence on Environmental Bacteria Cells

Smułek

Kaczorek

Hricovíniová

2017

J Surfact & Detergents

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A group of four selected non-ionic surfactants based on carbohydrates, namely octyl d-xyloside (C8X), nonyl d-xyloside (C9X), decyl d-xyloside (C10X) and dodecyl d-xyloside (C12X), have been investigated to accomplish a better understanding of their physico-chemical properties as well as biological activities. The surface-active properties, such as critical micelle concentration (CMC), emulsion and foam stability, the impact of the compounds on cell surface hydrophobicity and cell membrane permeability together with their toxicity on the selected bacterial strains have been determined as well. The studied group of surfactants showed high surface-active properties allowing a decrease in the surface tension to values below 25 mN m−1 for dodecyl d-xyloside at the CMC. The investigated compounds did not have any toxic influence on two Pseudomonas bacterial strains at concentrations below 25 mg L−1. The studied long-chain alkyl xylosides influenced both the cell inner membrane permeability and the cell surface hydrophobicity. Furthermore, the alkyl chain length, as well as the surfactant concentration, had a significant impact on the modifications of the cell surface properties. The tested non-ionic surfactants exhibited strong surface-active properties accompanied by the significant influence on growth and properties of Pseudomonas bacteria cells.

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Physico-chemical properties and cytotoxic effects of sugar-based surfactants: Impact of structural variations

Cited by 34 publications

References 31 publications

Synthesis and Evaluation of Saccharide-Based Aliphatic and Aromatic Esters as Antimicrobial and Antibiofilm Agents

Synthesis and Evaluation of Saccharide-Based Aliphatic and Aromatic Esters as Antimicrobial and Antibiofilm Agents

New QSPR Models to Predict the Critical Micelle Concentration of Sugar-Based Surfactants

Alkyl Xylosides: Physico‐Chemical Properties and Influence on Environmental Bacteria Cells

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