Synthesis, Structure, Surface and Antimicrobial Properties of New Oligomeric Quaternary Ammonium Salts with Aromatic Spacers

Brycki, Bogumił; Koziróg, Anna; Kowalczyk, Iwona; Pospieszny, Tomasz; Materna, Paulina; Marciniak, Jędrzej

doi:10.3390/molecules22111810

Cited by 27 publications

(17 citation statements)

References 49 publications

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“…The MIC values of alkyl rhamnosides decreased by increasing HLB to 5.0. This trend was previously observed [19]. The highest antibacterial activity was displayed for the alkyl rhamnoside (12C-Rha) with an HLB value of 5.0.…”

Section: Discussionsupporting

confidence: 84%

Alkyl rhamnosides, a series of amphiphilic materials exerting broad-spectrum anti-biofilm activity against pathogenic bacteria via multiple mechanisms

Peng

Hou

Zhang

et al. 2018

Artificial Cells, Nanomedicine, and Biotechnology

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As novel amphiphilic materials, six uncharged alkyl rhamnosides incorporating various alkyl chain and one rhamnose amine quaternary ammonium salt were successfully synthesized in this study. Their amphiphilic properties (HLB and CMC), antimicrobial and anti-biofilm activity against S. aureus and P. aeruginosa were investigated. Differentially regulated proteins and pathways were identified by comparative proteomics research to first give a sight on how alkyl rhamnosides performed the anti-biofilm activity at protein and pathway levels. Among the uncharged alkyl rhamnosides, dodecyl rhamnoside and octyl rhamnoside showed the best antimicrobial and anti-biofilm ability against S. aureus and against P. aeruginosa, respectively. Interestingly, the relationships between amphiphilic properties or MIC with anti-biofilm activity were first established. Uncharged alkyl rhamnoside with an optimized HLB value of 5.0 had both the strongest antibacterial and anti-biofilm activity against S. aureus, and MIC was the maximum biofilm inhibitory concentration for all alkyl rhamnosides. Alkyl rhamnosides have a significant overall regulatory effect on the proteomics and pathways of bacterial biofilms, including energy production, substrates transportation, signal transduction, key molecules balance, and so on. These amphiphilic materials have a great potential to be used as additives in pharmaceutic, cosmetic, food industry, hospital and in other non-medical fields.

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Section: Discussionsupporting

confidence: 84%

Alkyl rhamnosides, a series of amphiphilic materials exerting broad-spectrum anti-biofilm activity against pathogenic bacteria via multiple mechanisms

Peng

Hou

Zhang

et al. 2018

Artificial Cells, Nanomedicine, and Biotechnology

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“…Construction elements affecting CMC values are the length or nature of the spacer [ 68 , 81 , 82 , 83 , 84 , 85 , 86 , 87 ] and the kind of counter ion [ 69 , 88 , 89 ]. However, the length of hydrocarbon substituent affects the greatest impact on surface activity [ 90 , 91 , 92 , 93 , 94 , 95 , 96 , 97 , 98 ]. Generally, CMC decreases as the hydrophobicity of the substituent increases.…”

Section: Resultsmentioning

confidence: 99%

Antimicrobial Activity of Gemini Surfactants with Ether Group in the Spacer Part

et al. 2021

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Due to their large possibility of the structure modification, alkylammonium gemini surfactants are a rapidly growing class of compounds. They exhibit significant surface, aggregation and antimicrobial properties. Due to the fact that, in order to achieve the desired utility effect, the minimal concentration of compounds are used, they are in line with the principle of greenolution (green evolution) in chemistry. In this study, we present innovative synthesis of the homologous series of gemini surfactants modified at the spacer by the ether group, i.e., 3-oxa-1,5-pentane-bis(N-alkyl-N,N-dimethylammonium bromides). The critical micelle concentrations were determined. The minimal inhibitory concentrations of the synthesized compounds were determined against bacteria Escherichia coli ATCC 10536 and Staphylococcus aureus ATCC 6538; yeast Candida albicans ATCC 10231; and molds Aspergillus niger ATCC 16401 and Penicillium chrysogenum ATCC 60739. We also investigated the relationship between antimicrobial activity and alkyl chain length or the nature of the spacer. The obtained results indicate that the synthesized compounds are effective microbicides with a broad spectrum of biocidal activity.

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“…Not only conventional QASs (monomeric) but also more complex cationic surfactants may have antimicrobial properties. It was suggested that dimeric QASs (gemini) could be used as disinfectant agents because of their strong activity that depends mainly on the type of substituents, alkyl chain length,type and length of the linker (Piecuch et al ; Brycki et al ). Moreover, it was proved that dicephalic surfactants exhibit high, structure‐dependent antimicrobial activity, inhibiting the growth of bacteria and yeast (Piecuch et al ; Paluch et al ).…”

Section: Resultsmentioning

confidence: 99%

Biological activity of glycine and alanine derivatives of quaternary ammonium salts (QASs) against micro‐organisms

Rewak‐Soroczyńska

Paluch

Siebert

et al. 2019

Lett Appl Microbiol

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Quaternary ammonium salts (QASs) are commonly used in medicine, agriculture and industry and their wide usage caused the development of microbial resistance, thus there is still a need for new effective antimicrobial agents. Present work describes the biological activity of alanine‐ (DMALM‐n) and glycine‐derived (DMGM‐n) QASs against planktonic and biofilm forms of micro‐organisms. The antimicrobial activity was dependent mainly on the hydrocarbon chain length and surfactants with 12–16 atoms of carbon in the alkyl chain were the most active ones. The lowest MIC value was determined for DMALM‐14 against Rhodotorula rubra and Saccharomyces cerevisiae (2·5 µmol l−1). Generally, alanine derivatives showed stronger effects against micro‐organisms than glycine‐derived QASs. Alanine‐derived surfactants with 12–16 carbons in the alkyl chain had antiadhesive properties on the polystyrene surface, preventing cell attachment (about 70% of inhibition for C. albicans and 40% for S. epidermidis). Strong adhesion reduction was also observed on the stainless steel surface and the highest reduction was observed for C. albicans cells incubated on surface pretreated with DMGM‐16. Moreover, DMGM‐16 and DMALM‐16 prevented C. albicans filamentation, one of the determinants of cell adhesion. Surfactants with C16 alkyl chain (DMGM‐16 and DMALM‐16) eradicated bacterial and yeast biofilm (from 60 to 90% of reduction observed after incubation of the previously grown biofilm in the presence of the highest tested concentration of the surfactant – 400 µmol l−1) and reduced its viability. Strong antimicrobial activity as well as antiadhesive properties make alanine‐ and glycine‐derived QASs the potential candidates for future application as disinfectants. Significance and Impact of the Study Cationic surfactants are used in many fields, among others in medicine, cosmetic and pharmaceutical industry. Their usage on a large scale caused the development of microbial resistance mechanisms to such compounds. Thus, there is a need to synthesize new surfactants with potential application as effective disinfectants to combat both planktonic and biofilm forms of micro‐organisms. Present work focuses on the antimicrobial activity of chosen quaternary ammonium salts.

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Synthesis, Structure, Surface and Antimicrobial Properties of New Oligomeric Quaternary Ammonium Salts with Aromatic Spacers

Cited by 27 publications

References 49 publications

Alkyl rhamnosides, a series of amphiphilic materials exerting broad-spectrum anti-biofilm activity against pathogenic bacteria via multiple mechanisms

Alkyl rhamnosides, a series of amphiphilic materials exerting broad-spectrum anti-biofilm activity against pathogenic bacteria via multiple mechanisms

Antimicrobial Activity of Gemini Surfactants with Ether Group in the Spacer Part

Biological activity of glycine and alanine derivatives of quaternary ammonium salts (QASs) against micro‐organisms

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