Synthesis, Surface Property and Antimicrobial Activity of Cationic Gemini Surfactants Containing Adamantane and Amide Groups

Zhong, Xing; Guo, Juan; Fu, Shuqin; Zhu, Dunming; Peng, Jing

doi:10.1007/s11743-014-1580-7

Cited by 17 publications

(5 citation statements)

References 26 publications

(48 reference statements)

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“…The minimum inhibitory concentration (MIC) of the synthesized Gemini surfactants was determined using the 96‐well titre method with BKC taken as control as shown in Table 4. The synthesized surfactants showed sufficient anti‐bacterial activity since the minimum inhibitory concentrations of the synthesized surfactants against Gram‐positive and Gram‐negative bacteria were found to be comparable to that of other reported cationic Gemini surfactants and benzalkonium chloride, which is a well‐known anti‐bacterial agent (Shaban et al, 2016; Tatsumi et al, 2014; Zhong et al, 2014; Zhu et al, 2016). The MIC of 12‐6‐12 GS was found to be lowest amongst the synthesized surfactants against E. coli (Gram‐negative) whereas, the MIC of 12‐3‐12 GS was found to be lowest in the case of B. subtilis (Gram‐positive).…”

Section: Resultssupporting

confidence: 57%

Synthesis and application of novel Gemini esterquats in fabric softeners: Role of spacer chain length on surfactant properties

Paranjpe,

Sanap,

Madankar

et al. 2024

J Surfact & Detergents

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Gemini surfactants are dimeric molecules having two monomeric units connected by a spacer. Gemini surfactants, owing to their molecular structure have better surfactant properties than other monomeric surfactants. Esterquat class gemini surfactants can be synthesized using a spacer containing ester linkages. In the current study, the synthesis of novel esterquat gemini surfactants was carried out with spacers of varying chain lengths and was characterized using sophisticated instrumental methods. Various surfactant properties including foaming, emulsification, CMC, surface excess, antimicrobial activity and wetting potential using contact angle were analyzed and compared with benzalkonium chloride. It was observed that the CMC as low as 24.79 × 10−3 mM of the synthesized surfactants is potentially lower than that of conventional monomeric surfactants and was found to increase with an increase in spacer chain length. Further, the applicability and evaluation of performance properties of the synthesized surfactants were studied in fabric softener formulation. The water absorbency and whiteness retention of the formulation prepared using 12‐6‐12 GS was the highest due to its better wettability amongst other synthesized surfactants owing to its higher spacer chain length. To summarize, the surface and anti‐microbial properties of the synthesized surfactants vary greatly with the alteration in spacer chain length.

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Section: Resultssupporting

confidence: 57%

Synthesis and application of novel Gemini esterquats in fabric softeners: Role of spacer chain length on surfactant properties

Paranjpe,

Sanap,

Madankar

et al. 2024

J Surfact & Detergents

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“…The antibacterial activity thus depends on the hydrophilic-hydrophobic balance of the cationic surfactants. Increase in the alkyl chain length (from C 12 to C 16 ) increases the hydrophobic character, which may be too high to facilitate transport through the bacterial cell membrane [41].…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Disinfection Effect of the Pyridine-4-aldoxime Based Salts

et al. 2015

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A set of new quaternary ammonium compounds based on pyridine-4-aldoxime was synthesized, characterized with analytical data (NMR, EA, HPLC, MS) and tested for in vitro antimicrobial activity (antibacterial, antifungal) and cytotoxicity. Quaternary pyridinium-4-aldoxime salts with length of alkyl side chain from C8 to C20 and belonging to the group of cationic surfactants were investigated in this work. An HPLC experimental protocol for characterization of mixtures of all homologues has been found. Antimicrobial evaluation found that yeast-type fungi were most sensitive towards C14 and C16 analogues, whereas the C16 analogue was completely ineffective against filamentous fungi. Antibacterial assessment showed versatility of C14 and relatively high efficacy of C16 OPEN ACCESSMolecules 2015, 20 3682 against G+ strains and C14 against G− strains. Notably, none of the studied compounds exceeded the efficacy and versatility of the benzalkonium C12 analogue, and benzalkonium analogues also exhibited lower cytotoxicity in the cell viability assay.

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“…There were several attempts to evaluate the effectiveness of antibacterial activity of Gemini surfactants. However, these are usually limited to the compound structure-it is directly associated with the type and length of spacer in the molecule and/or the length of hydrophobic chains [8][9][10]. Numerous scientists proved that number of carbon atoms is correlated with the antimicrobial activity [11,12].…”

Section: Introductionmentioning

confidence: 99%

A Systematic Approach: Molecular Dynamics Study and Parametrisation of Gemini Type Cationic Surfactants

Rzycki

Kaczorowska

Kraszewski

et al. 2021

IJMS

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The spreading of antibiotic-resistant bacteria strains is one of the most serious problem in medicine to struggle nowadays. This triggered the development of alternative antimicrobial agents in recent years. One of such group is Gemini surfactants which are massively synthesised in various structural configurations to obtain the most effective antibacterial properties. Unfortunately, the comparison of antimicrobial effectiveness among different types of Gemini agents is unfeasible since various protocols for the determination of Minimum Inhibitory Concentration are used. In this work, we proposed alternative, computational, approach for such comparison. We designed a comprehensive database of 250 Gemini surfactants. Description of structure parameters, for instance spacer type and length, are included in the database. We parametrised modelled molecules to obtain force fields for the entire Gemini database. This was used to conduct in silico studies using the molecular dynamics to investigate the incorporation of these agents into model E. coli inner membrane system. We evaluated the effect of Gemini surfactants on structural, stress and mechanical parameters of the membrane after the agent incorporation. This enabled us to select four most likely membrane properties that could correspond to Gemini’s antimicrobial effect. Based on our results we selected several types of Gemini spacers which could demonstrate a particularly strong effect on the bacterial membranes.

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Synthesis, Surface Property and Antimicrobial Activity of Cationic Gemini Surfactants Containing Adamantane and Amide Groups

Cited by 17 publications

References 26 publications

Synthesis and application of novel Gemini esterquats in fabric softeners: Role of spacer chain length on surfactant properties

Synthesis and application of novel Gemini esterquats in fabric softeners: Role of spacer chain length on surfactant properties

Synthesis and Disinfection Effect of the Pyridine-4-aldoxime Based Salts

A Systematic Approach: Molecular Dynamics Study and Parametrisation of Gemini Type Cationic Surfactants

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