Urea-based gemini surfactants: Synthesis, aggregation behaviour and biological activity

Pisárčik, Martin; Pupák, Matúš; Devı́nsky, Ferdinand; Almásy, László; Tian, Qiang; Bukovský, Marián

doi:10.1016/j.colsurfa.2016.03.028

Cited by 23 publications

(12 citation statements)

References 63 publications

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“…A similar observation was also made in our previous study of aggregation of urea-based gemini surfactants [31] where nonlinear dependences of aggregation parameters were found as a function of the spacer length with worse aggregation detected for medium spacer lengths. Moreover, strong aggregation for short spacer gemini molecules with urea groups in the alkyl chains also resulted from the increased hydrogen bonding between urea groups [31]. This could also be the case of gemini molecules with short spacer ( a1, a2 ) where the amide groups in the spacer are separated by just one or two methylene groups and intramolecular hydrogen bonding can take place which results in the increased aggregation number values (Figure 1 and Figure 2A).…”

Section: Resultssupporting

confidence: 87%

“…This results in the formation of small spherical micelles with small hydrodynamic diameter, small aggregation numbers independent of surfactant concentration and large interfacial area per surfactant molecule [29,30]. A similar observation was also made in our previous study of aggregation of urea-based gemini surfactants [31] where nonlinear dependences of aggregation parameters were found as a function of the spacer length with worse aggregation detected for medium spacer lengths. Moreover, strong aggregation for short spacer gemini molecules with urea groups in the alkyl chains also resulted from the increased hydrogen bonding between urea groups [31].…”

Section: Resultssupporting

confidence: 76%

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Self-Assembly Properties of Cationic Gemini Surfactants with Biodegradable Groups in the Spacer

et al. 2019

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: Self-assembly properties of cationic gemini surfactants with biodegradable amide or ester groups in the spacer were investigated utilising time-resolved fluorescence quenching, dynamic light scattering and zeta potential measurements. A correlation between aggregation parameters such as micelle aggregation number, micelle size and zeta potential with the structure of gemini molecules was made. For gemini molecules with medium spacer lengths, micelle aggregation number does not change much with the surfactant concentration. When the spacer is extended, a stronger aggregation tendency is observed for gemini surfactant molecules with two ester groups in the spacer and the aggregation number increases. The assumption of stronger aggregation of ester-based gemini molecules at larger spacer number values is also documented by measurements of the size and zeta potential of ester-based micelles. The explanation of the difference in aggregation ability of amide-based and ester-based gemini molecules is related to the structural features of gemini molecules, notably to the larger flexibility and denser arrangement of ester-based gemini molecules in a micelle. To support this assumption, optimised 3D models of the studied gemini molecules were constructed. Correspondingly, the calculations show smaller size and interfacial area for ester-based gemini conformers.

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Section: Resultssupporting

confidence: 87%

Section: Resultssupporting

confidence: 76%

Self-Assembly Properties of Cationic Gemini Surfactants with Biodegradable Groups in the Spacer

et al. 2019

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“…The reason for this may be that policationic compounds can easily interact with charged cell surfaces. Moreover, they can increase membrane fluidity and consequently lead to cell death [ 32 , 33 , 34 , 35 ]. The results presented in our study are similar to those reported for yeast by Obłąk et al [ 36 ].…”

Section: Discussionmentioning

confidence: 99%

Impact of Cationic and Neutral Gemini Surfactants on Conidia and Hyphal Forms of Aspergillus brasiliensis

Koziróg

Brycki

Pielech‐Przybylska

2018

IJMS

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This study investigates the biological activity of two cationic gemini surfactants, hexamethylene-1,6-bis-(N,N-dimethyl-N-dodecylammonium bromide) C6 and pentamethylene-1,5-bis-(N,N-dimethyl-N-dodecylammonium bromide) C5, and their two neutral analogs, hexamethylene-1,6-bis-(N-methyl-N-dodecylamine) (A6) and pentamethylene-1,5-bis-(N-methyl-N-dodecylamine) (A5). Experiments were performed with Aspergillus brasiliensis, which is used in the standard tests for biocides. The minimal inhibitory concentration (MIC) values for conidia and mycelium were determined using the dilution method. The viability of the conidia was evaluated using the plate count method. The dry mass of the mycelium was determined using the thermogravimetric method. Ergosterol was extracted from the mycelium and evaluated by gas chromatography. The effect of gemini surfactants on fungal morphology was observed using scanning electron microscopy. Cationic gemini surfactants were found to be active at lower concentrations compared to their non-ionic analogues, rapidly reducing the total number of conidia that were able to grow. They also decreased both the ergosterol content in the mycelium and its dry weight. These results suggest that cationic gemini surfactants C6 and C5 could have a wide range of practical applications as active compounds. However, it should be remembered that usage at too low concentrations, below the MIC, will only lead to short-term disturbances in the development of conidia and mycelium.

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“…Analytical, Inorganic, Organic, Physical, Materials Science microorganisms as microbial colloids (Peng et al 2018;Pisarcik et al 2016). It's worth noting that microbial colloids are neither mineral colloids nor soil humus colloids.…”

Section: Chemistry Journalsmentioning

confidence: 99%

Peer Review #1 of "Aggregation kinetics of binary systems containing kaolinite and Pseudomonas putida induced by different 1:1 electrolytes: specific ion effects (v0.1)"

2020

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Background. The interactions between colloidal particles in the binary system or mixture colloids containing clay minerals and bacteria have important influences on formations and stabilities of soil aggregates, transportations of soil water, as well as biological activities of microorganisms. How the interfacial reaction of metal ions affects their interaction therefore becomes an important scientific issue. Methods. Dynamic light scattering studies on the aggregation kinetics of mixture colloids containing kaolinite and Pseudomonas putida (P. putida) were conducted in this study. Results. Aggregation could be observed between kaolinite and kaolinite, between kaolinite and P. putida when P. putida content was less than 33.3%. Additionally, aggregation rates decreased with increasing P. putida content. The critical coagulation concentrations and activation energies indicated that there were strong specific ion effects on the aggregation of mixture colloids. Most importantly, the activation energy increased sharply with increasing P. putida content , which might result from the lower Hamaker constant of P. putida compared with that of kaolinite. Contributions. (1) Strong specific ion effects on mixture colloids aggregation of kaolinite-Pseudomonas putida were observed; (2) the aggregation behavior of mixture colloidal system was determined by the average effects of mixture colloids, rather than the specific component in mixture systems. This finding provides an important methodological guide for further studies on the colloidal aggregation behavior of mixture systems with organic and inorganic materials.

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Urea-based gemini surfactants: Synthesis, aggregation behaviour and biological activity

Abstract: with the maximum antimicrobial activity found at the spacer length of 6 CH2 groups for bacteria and 8 CH2 groups for fungi. This is related to a different composition of cell membrane of the used microorganisms.

Cited by 23 publications

References 63 publications

Self-Assembly Properties of Cationic Gemini Surfactants with Biodegradable Groups in the Spacer

Self-Assembly Properties of Cationic Gemini Surfactants with Biodegradable Groups in the Spacer

Impact of Cationic and Neutral Gemini Surfactants on Conidia and Hyphal Forms of Aspergillus brasiliensis

Peer Review #1 of "Aggregation kinetics of binary systems containing kaolinite and Pseudomonas putida induced by different 1:1 electrolytes: specific ion effects (v0.1)"

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