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

Pisárčik, Martin; Polakovičová, Mája; Markuliak, Mário; Lukáč, Miloš; Devı́nsky, Ferdinand

doi:10.3390/molecules24081481

Cited by 32 publications

(19 citation statements)

References 33 publications

(57 reference statements)

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“…In recent years, particular attention is focused on gemini surfactants due to their advanced structure-activity correlation, superior aggregation capacity, and versatile morphological behavior [4,43]. Unlike conventional single head surfactants, gemini analogs consist of two equal head groups bearing two tails bridged with a spacer.…”

Section: Structural Diversity Of Biocompatible and Ecologically Frmentioning

confidence: 99%

Cationic Surfactants: Self-Assembly, Structure-Activity Correlation and Their Biological Applications

Zakharova

Pashirova

Doktorovová

et al. 2019

IJMS

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The development of biotechnological protocols based on cationic surfactants is a modern trend focusing on the fabrication of antimicrobial and bioimaging agents, supramolecular catalysts, stabilizers of nanoparticles, and especially drug and gene nanocarriers. The main emphasis given to the design of novel ecologically friendly and biocompatible cationic surfactants makes it possible to avoid the drawbacks of nanoformulations preventing their entry to clinical trials. To solve the problem of toxicity various ways are proposed, including the use of mixed composition with nontoxic nonionic surfactants and/or hydrotropic agents, design of amphiphilic compounds bearing natural or cleavable fragments. Essential advantages of cationic surfactants are the structural diversity of their head groups allowing of chemical modification and introduction of desirable moiety to answer the green chemistry criteria. The latter can be exemplified by the design of novel families of ecological friendly cleavable surfactants, with improved biodegradability, amphiphiles with natural fragments, and geminis with low aggregation threshold. Importantly, the development of amphiphilic nanocarriers for drug delivery allows understanding the correlation between the chemical structure of surfactants, their aggregation behavior, and their functional activity. This review focuses on several aspects related to the synthesis of innovative cationic surfactants and their broad biological applications including antimicrobial activity, solubilization of hydrophobic drugs, complexation with DNA, and catalytic effect toward important biochemical reaction.

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Section: Structural Diversity Of Biocompatible and Ecologically Frmentioning

confidence: 99%

Cationic Surfactants: Self-Assembly, Structure-Activity Correlation and Their Biological Applications

Zakharova

Pashirova

Doktorovová

et al. 2019

IJMS

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“…There are several factors influencing the value of CMC of cationic GS, such as the following: temperature, chemical structure, and the presence of other substances in the solution [ 1 ]. 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 ].…”

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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“…Several researchers reported the efficacy of gemini surfactants in altering the rock wettability [48][49][50]. In addition, gemini surfactant possesses other interesting properties, such as low critical micelle concentration (CMC) [51,52]. In this work, GS was used to reduce the oil-wetness and therefore enhance the condensate mobility.…”

Section: Wettability Alterationmentioning

confidence: 99%

Novel Treatment for Mitigating Condensate Bank Using a Newly Synthesized Gemini Surfactant

et al. 2020

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Condensate accumulation in the vicinity of the gas well is known to curtail hydrocarbon production by up to 80%. Numerous approaches are being employed to mitigate condensate damage and improve gas productivity. Chemical treatment, gas recycling, and hydraulic fracturing are the most effective techniques for combatting the condensate bank. However, the gas injection technique showed temporary condensate recovery and limited improvement in gas productivity. Hydraulic fracturing is considered to be an expensive approach for treating condensate banking problems. In this study, a newly synthesized gemini surfactant (GS) was developed to prevent the formation of condensate blockage in the gas condensate reservoirs. Flushing the near-wellbore area with GS will change the rock wettability and thereby reduce the capillary forces holding the condensate due to the strong adsorption capacity of GS on the rock surface. In this study, several measurements were conducted to assess the performance of GS in mitigating the condensate bank including coreflood, relative permeability, phase behavior, and nuclear magnetic resonance (NMR) measurements. The results show that GS can reduce the capillary pressure by as much as 40%, increase the condensate mobility by more than 80%, and thereby mitigate the condensate bank by up to 84%. Phase behavior measurements indicate that adding GS to the oil–brine system could not induce any emulsions at different salinity levels. Moreover, NMR and permeability measurements reveal that the gemini surfactant has no effect on the pore system and no changes were observed in the T2 relaxation profiles with and without the GS injection. Ultimately, this work introduces a novel and effective treatment for mitigating the condensate bank. The new treatment showed an attractive performance in reducing liquid saturation and increasing the condensate relative permeability.

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

Cited by 32 publications

References 33 publications

Cationic Surfactants: Self-Assembly, Structure-Activity Correlation and Their Biological Applications

Cationic Surfactants: Self-Assembly, Structure-Activity Correlation and Their Biological Applications

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

Novel Treatment for Mitigating Condensate Bank Using a Newly Synthesized Gemini Surfactant

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