Synthesis, physicochemical, and biological activities of novel N-acyl tyrosine monomeric and Gemini surfactants in single and SDS/CTAB-mixed micellar system

Abstract

A series of single-chained N-acyl tyrosine surfactants with varying chain lengths (C 10 -C 18 ) and degree of unsaturation, as well as an N-acyl Gemini tyrosine surfactant with chain length C 12 , were synthesized, and the structures were confirmed using spectral analysis. The effect of chain length and level of unsaturation on the physicochemical and antibacterial properties of the N-acyl tyrosine surfactants was evaluated. The C 12 derivative displayed the optimum antibacterial activity among the single chain surfactants, and the presence of double bond in the oleoyl derivative enhanced the antibacterial activity over its saturated analogue. The N-acyl Gemini surfactant displayed the highest antibacterial activity among the series and also showed greater micelle forming ability than its single chain analogue. Mixed micellar behavior of the N-acyl Gemini surfactant with conventional cationic (CTAB) and anionic (SDS) surfactants in aqueous solution was studied. The negative value of the interaction parameter β 12 observed for the N-acyl Gemini in binary mixture with CTAB surfactant indicated a synergistic interaction within the mixed micellar system. However, the binary mixture with SDS displayed antagonistic behavior. The binary mixture of N-acyl Gemini surfactant with CTAB displayed better antibacterial activity and foaming properties than with SDS mixtures. Optimum antibacterial activity was observed for N-acyl Gemini surfactant with mole ratio 0.4 to 0.6 in the CTAB binary mixture, at which the lowest ocular irritation index was observed. Overall, the study showed that the Gemini surfactant in combination with the conventional surfactant CTAB can be used as potential ingredients in detergent and pharmaceutical formulations. FIGURE 7 Variation of CMC with mole fraction of surfactant 8 in (A) SDS and (B) CTAB mixed systems. CMC indicates critical micelle concentration; CTAB, cetyl trimethyl ammonium bromide; SDS, sodium dodecyl sulfate JOONDAN ET AL.

The planctomycete Stieleria maiorica Mal15T employs stieleriacines to alter the species composition in marine biofilms

“…Evidence for the presence of N-acylated derivatives of aromatic or basic amino acids was mainly based on a multitude of environmental DNA libraries. Characterisation of biosynthetic pathways for N-acyl amino acids is an important task in the future given that such compounds find potential biotechnological applications as antimicrobial surfactants and precursors for biodegradable polyesters in pharmaceutical and biomedical applications 30,31 . In case of the surfactants, the C 12 chain as acyl residue (as present in stieleriacine A 1 ) proved to Fig.…”

Mixed micellization study of dodecyltrimethylammonium chloride and cetyltrimethylammonium bromide mixture in aqueous/urea medium at different temperatures: Theoretical and experimental view

“…β = 0 stands to express the ideal mixing of the components (no net interaction). The more the value of β , the higher is the degree of interaction between the amphiphiles . The negative value of interaction parameter owes the hydrophobic interaction amid tails of the amphiphiles.…”

“…The more the value of β, the higher is the degree of interaction between the amphiphiles. [28,48] The negative value of interaction parameter owes the hydrophobic interaction amid tails of the amphiphiles. It was observed that the value of β rises with the enhancement of the mole fraction of CTAB in absence/occurrence of NH 2 -CO-NH 2 in almost all cases denotes the interaction between constituents enhances with an increase in mole fraction of CTAB (Tables 1-3).…”

Kinetic and mechanistic investigations of [Zn (II)‐Trp]+ and ninhydrin in aqueous and cationic CTAB surfactant

“…Thus, investigations of [Zn (II)-Trp] + and ninhydrin could be utilized as a simple and reliable kinetic probe in aggregated structural systems. The investigation may also be performed in the presence of gemini surfactant micelles [52][53][54][55][56] as well as mixed surfactant systems [57][58][59][60] for the enhanced utility of technique/method.…”