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Green cationic arginine surfactants: Influence of the polar head cationic character on the self-aggregation and biological properties.

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Title: Green cationic arginine surfactants: Influence of the polar head cationic character on the self-aggregation and biological properties.
Authors: Pérez, Lourdes1 (AUTHOR), Pons, Ramon1 (AUTHOR), Oliveira de Sousa, Francisco Fábio2,3 (AUTHOR), Morán, Maria del Carmen4 (AUTHOR), Ramos da Silva, Anderson1 (AUTHOR), Pinazo, Aurora1 (AUTHOR) aurora.pinazo@iqac.csic.es
Source: Journal of Molecular Liquids. Oct2021, Vol. 339, pN.PAG-N.PAG. 1p.
Subjects: Cationic surfactants, Liquid crystal states, Erythrocyte membranes, Biological membranes, Raw materials, Amino group, Surface active agents, Methyl formate
Abstract: [Display omitted] • Synthesis of cationic arginine surfactants meets green chemistry requirements. • pKa shift were observed for the guanidinium and for the primary amino group. • Cationic arginine surfactant aggregate in cylinders that pack in hexagonal phases. • Cationic Arginine surfactants interact strongly with DPPC monolayer. • Arginine surfactants have activity against Methicillin-resistant S. aureus (MRSA) Green surfactants are compounds derived from renewable sources of raw material that exhibit biodegradability and low toxicity. In this work the synthesis, solution, aggregation and biological properties of two families of green cationic arginine based surfactants have been investigated, Nα-acyl arginine methyl ester and arginine N-alkyl amide. Specifically we study: (i) the effect of self-aggregation on the cationic character, (ii) Liquid crystalline phases applying SAXS, (iii) surfactant ability to interact with biological membranes using Langmuir DPPC monolayers as a simple membrane model, (iv) biological profiles obtained by evaluation of antibacterial, anti-yeast and antibiofilm properties and, (v) the hemolytic activity on erythrocytes. The experiments conducted showed that the biological properties of arginine based surfactants were outstanding. These along with the fact that they are derived from green raw materials confer to these surfactants an outstanding potential in the field of green antimicrobial and antibiofilm agents. [ABSTRACT FROM AUTHOR]
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Database: Engineering Source
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Abstract:[Display omitted] • Synthesis of cationic arginine surfactants meets green chemistry requirements. • pKa shift were observed for the guanidinium and for the primary amino group. • Cationic arginine surfactant aggregate in cylinders that pack in hexagonal phases. • Cationic Arginine surfactants interact strongly with DPPC monolayer. • Arginine surfactants have activity against Methicillin-resistant S. aureus (MRSA) Green surfactants are compounds derived from renewable sources of raw material that exhibit biodegradability and low toxicity. In this work the synthesis, solution, aggregation and biological properties of two families of green cationic arginine based surfactants have been investigated, Nα-acyl arginine methyl ester and arginine N-alkyl amide. Specifically we study: (i) the effect of self-aggregation on the cationic character, (ii) Liquid crystalline phases applying SAXS, (iii) surfactant ability to interact with biological membranes using Langmuir DPPC monolayers as a simple membrane model, (iv) biological profiles obtained by evaluation of antibacterial, anti-yeast and antibiofilm properties and, (v) the hemolytic activity on erythrocytes. The experiments conducted showed that the biological properties of arginine based surfactants were outstanding. These along with the fact that they are derived from green raw materials confer to these surfactants an outstanding potential in the field of green antimicrobial and antibiofilm agents. [ABSTRACT FROM AUTHOR]
ISSN:01677322
DOI:10.1016/j.molliq.2021.116819