Amino acids: Building blocks for the synthesis of greener amphiphiles

Joondan, Nausheen; Laulloo, Sabina Jhaumeer; Caumul, Prakashanand

doi:10.1080/01932691.2017.1421085

Cited by 18 publications

(8 citation statements)

References 119 publications

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“…Bio-ingredients from renewable, plant-based sources with improved performance and decreased toxicity such as biosurfactants and amino acid-based surfactants (AAS) are a promising class of ingredients due to their biocompatibility and biodegradability characteristics [30][31][32][33][34][35][36][37][38][39][40][41][42]. AAS's are synthesized from natural amino acids and comprise of the amino acid group with a chemical formula HO 2 C-CHR-NH 2 or its residue [32,43].…”

Section: Introductionmentioning

confidence: 99%

Impact of Processing Conditions on Rheology, Tribology and Wet Lubrication Performance of a Novel Amino Lipid Hair Conditioner

2021

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The objective of this work was to carry out a comprehensive evaluation of the performance of a novel cationic amino lipid surfactant, Brassicyl Valinate Esylate (BVE), in contrast to conventional alkyl quaternary ammonium surfactants (quats), through a study of the effects of process mixing speed on its overall rheological, tribological and wet lubrication performance in comparison to BTAC and CTAC, two cationic surfactants widely used in cosmetics. The major cosmetic application of cationic surfactants is in the preparation of hair conditioners. Hence, this analysis was done firstly by conducting tensile combing tests to evaluate reduction in wet lubrication which translates to conditioning performance. The combing results serve as a testing metric that adequately corresponds to consumer perception of conditioned hair. To correlate this technically, yield stress measurements were conducted to establish rheologic profiles of the conditioner formulations, and in vitro tribological testing of the emulsion systems between two steel surfaces were done to technically simulate the spreading and rubbing of conditioner on the hair. The effect of processing conditions on the formulations was then evaluated. BVE was found to be an effective conditioning surfactant suitable as an eco-friendly replacement for BTAC and CTAC in hair conditioner formulations. The results showed that higher shear mixing rates during formulation lead to poorer performance effects evident through decreased yield stress values, lower percentage reduction in combing force and a higher coefficient of friction.

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Section: Introductionmentioning

confidence: 99%

Impact of Processing Conditions on Rheology, Tribology and Wet Lubrication Performance of a Novel Amino Lipid Hair Conditioner

2021

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“…However, our previous published work demonstrated that Bz-Arg-NHC n display both hemolytic and protective activity above this parameter (Fait et al 2018). Moreover, Joondan and coworkers proved a similar trend for the hemolytic activity of aromatic amino acid-based surfactants, evidencing the crucial role of the surfactants' aggregates in the disruption of the membrane structure (Joondan et al 2016(Joondan et al , 2017Fait et al 2018).…”

Section: Discussionmentioning

confidence: 85%

Interaction of cationic surfactants with DPPC membranes: effect of a novel Nα-benzoylated arginine-based compound

et al. 2021

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Cationic amino acid-based surfactants are known to interact with the lipid bilayer of microorganism resulting in cell death through a disruption of the membrane topology. To elucidate the interaction of a cationic surfactant synthesized in our lab, investigations involving N α -benzoyl-arginine decyl amide (Bz-Arg-NHC 10 ), and model membranes composed by 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) were done. Bz-Arg-NHC 10 was able to penetrate into DPPC monolayers up to a critical pressure of 59.6 mN m −1 . Differential scanning calorimetry revealed that as the concentration of Bz-Arg-NHC 10 increased, the main transition temperature of DPPC slightly decreased. Atomic force microscopy (AFM) in situ experiments performed on supported DPPC bilayers on mica allowed monitoring the changes induced by Bz-Arg-NHC 10 . DPPC bilayer patches were partially removed, mainly in borders and bilayer defects for 50 µM Bz-Arg-NHC 10 solution. Increasing the concentration to 100 µM resulted in a complete depletion of the supported bilayers. Surface plasmon resonance (SPR) experiments, carried out with fully DPPC bilayers covered chips, showed a net increase of the SPR signal, which can be explained by Bz-Arg-NHC 10 adsorption. When patchy DPPC bilayers were formed on the substrate, a SPR signal net decrease was obtained, which is consistent with the phospholipids' removal observed in the AFM images. The results obtained suggest that the presence of the benzoyl group attached to the polar head of our compound would be the responsible of the increased antimicrobial activity against gram-negative bacteria when compared with other arginine-based surfactants.

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“…Their structural diversity allows for the synthesis of various surfactants, as different moieties can be introduced at different molecular sites via acylation, esterication, reductive amination or alkylation reactions. [7][8][9]23 The resulting derivatives can therefore be anionic, [24][25][26][27] cationic, [28][29][30] zwitterionic 31 or even non-ionic [32][33][34] surfactants of wide structural variety and diverse physicochemical properties. This, in turn, leads to the potential for applications of AAS in different elds, including biomedicine, [35][36][37] pharmaceuticals, [38][39][40][41][42] gelators, [42][43][44][45][46] micellar catalysis, 47,48 cosmetics, 49 consumer products, 50 food additives and supplements.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, physicochemical characterization and aquatic toxicity studies of anionic surfactants derived from amino and α-hydroxy acids

Kalebic,

Binnemans,

de Witte

et al. 2023

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Amino acids: Building blocks for the synthesis of greener amphiphiles

Cited by 18 publications

References 119 publications

Impact of Processing Conditions on Rheology, Tribology and Wet Lubrication Performance of a Novel Amino Lipid Hair Conditioner

Impact of Processing Conditions on Rheology, Tribology and Wet Lubrication Performance of a Novel Amino Lipid Hair Conditioner

Interaction of cationic surfactants with DPPC membranes: effect of a novel Nα-benzoylated arginine-based compound

Synthesis, physicochemical characterization and aquatic toxicity studies of anionic surfactants derived from amino and α-hydroxy acids

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