Solution properties of amino acid-type new surfactant

Tabohashi, Tatsuru; Tobita, Kazuhiko; Sakamoto, Kazutami; Kouchi, Junichi; Yokoyama, Shoko; Sakai, Hideki; Abe, Masahiko

doi:10.1016/s0927-7765(00)00170-3

Cited by 25 publications

(22 citation statements)

References 19 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…This behavior is common in amino acid based surfactants 24 as well as in other cationic surfactants in which the cationic charge is situated on a protonated amine group. 25,26 Surfactants with lower pKa values are those in which the positive charge is located on the alpha amino group.…”

Section: Physicochemical Studiesmentioning

confidence: 99%

pH-Sensitive Surfactants from Lysine: Assessment of Their Cytotoxicity and Environmental Behavior

et al. 2012

View full text Add to dashboard Cite

The toxicity and environmental behavior of new pH-sensitive surfactants from lysine are presented. Three different chemical structures are studied: surfactants with one amino acid and one alkyl chain, surfactants with two amino acids on the polar head and one alkyl chain, and gemini surfactants. The pH sensitivity of these compounds can be tuned by modifying their chemical structures. Cytotoxicity has been evaluated using erythrocytes and fibroblast cells. The toxic effects against these cells depend on the hydrophobicity of the molecules as well as their cationic charge density. The effect of hydrophobicity and cationic charge density on toxicity is different for each type of cells. For erythrocytes, the toxicity increases as hydrophobicity and charge density increases. Nevertheless, for fibroblasts cationic charge density affects cytotoxicity in the opposite way: the higher charge density, the lower the toxicity. The effect of the pH on hemolysis has been evaluated in detail. The aquatic toxicity was established using Daphnia magna. All surfactants yielded EC50 values considerably higher than that reported for cationic surfactants based on quaternary ammonium groups. Finally, their biodegradability was evaluated using the CO2 headspace test (ISO 14593). These lysine derivatives showed high levels of biodegradation under aerobic conditions and can be classified as “readily biodegradable compounds”.

show abstract

Section: Physicochemical Studiesmentioning

confidence: 99%

pH-Sensitive Surfactants from Lysine: Assessment of Their Cytotoxicity and Environmental Behavior

et al. 2012

View full text Add to dashboard Cite

show abstract

“…However, to estimate the protonation state of the surfactant molecule in the pH range studied, we determined the apparent pKa values of the polar groups when they were included in the surfactant molecule. The pKa value of each compound was estimated by potentiometric titration, as described by Tabohashi et al (2001). The titration was carried out at 25 ºC by adding increments of the NaOH solution to the surfactant solution with constant magnetic stirring, and the pKa value was obtained from the inflection point in the titration curve.…”

Section: Ph-dependent Hemolysismentioning

confidence: 99%

Membrane-destabilizing activity of pH-responsive cationic lysine-based surfactants: role of charge position and alkyl chain length

et al. 2011

View full text Add to dashboard Cite

“…Amino acidtype surfactants, with their antimicrobial activity, biocompatibility and excellent skin feel, are thought to be potential surfactants in food, cosmetic and personal care products, which are biodegradable and safe to the living body (Holmberg, 2001;Tabohashi et al, 2001). Recently, much attention has been paid to the enzymatic synthesis of various compounds through condensation or transesterification in organic solvent.…”

Section: Introductionmentioning

confidence: 99%

Lipase-catalyzed synthesis of O-lauroyl l-serinamide and O-lauroyl l-threoninamide

Zhang

Adachi

Watanabe

et al. 2005

Food Research International

View full text Add to dashboard Cite

Solution properties of amino acid-type new surfactant

Cited by 25 publications

References 19 publications

pH-Sensitive Surfactants from Lysine: Assessment of Their Cytotoxicity and Environmental Behavior

pH-Sensitive Surfactants from Lysine: Assessment of Their Cytotoxicity and Environmental Behavior

Membrane-destabilizing activity of pH-responsive cationic lysine-based surfactants: role of charge position and alkyl chain length

Lipase-catalyzed synthesis of O-lauroyl l-serinamide and O-lauroyl l-threoninamide

Contact Info

Product

Resources

About