Properties and Applications of Quaternary Ammonium Gemini Surfactant 12-6-12: An Overview.

Surfactants are amphiphilic molecules and one of the most versatile products of the chemical industry. They can be absorbed at the air-water interface and can align themselves so that the hydrophobic part is in the air while the hydrophilic part is in water. This alignment lowers the surface or interfacial tension. Gemini surfactants are a modern variety of surfactants with unique properties and a very wide range of potential applications. Hexamethylene-1,6-bis(N-dodecyl-N,N-dimethylammonium bromide) is one such representative compound that is a better alternative to a single analogue. It shows excellent surface, antimicrobial, and anticorrosion properties. With a highly efficient synthetic method and a good ecological profile, it is a potential candidate for numerous applications, including biomedical applications.

Evaluation of the antiviral potential of gemini surfactants against influenza virus H1N1.

Influenza A virus (IAV) affects human health worldwide as a high-risk disease. It can neither be easily controlled by current vaccines and nor be treated by conventional drugs. Gemini surfactants (GS) have shown several properties including antiviral activity. In this study, the antiviral capacity of some GS compounds with different levels of hydrophobicity was examined. The 50% cytotoxic (CC50) and non-cytotoxic (NCTC) concentrations of the compounds were determined by MTT method. The NCTCs, the same as effective concentrations (EC50s), were tested for the antiviral capacity against IAV in different combination treatments for 1 h incubation on MDCK cells. The HA and MTT assays were used to evaluate the virus titer and cell viabilities, respectively. The hemolytic activity of the compounds was also assessed using an HA inhibition assay. To evaluate the apoptotic effect of GS compounds, Annexin V-PI kit was used. The HA titers decreased between 1-6.5 logs, 1-4.5 logs, and 1-5.5 logs in simultaneous, pre- and post-penetration combination treatments, respectively. The cell viability values in all combination treatments were favorable. The HI assay indicated the hemolytic potential of GSs and their physical interaction with viral HA. The apoptosis test results highlighted anti-apoptotic capacity of the GS compounds alone and in the presence of influenza virus especially for the hydrophobic ones. Gemini surfactants were generally more efficacious in simultaneous treatment. Their antiviral potential may be attributed to their physical interaction with viral membrane or HA glycoprotein that disrupts viral particle or blocks viral entry to the cell and inhibits its propagation.

Fabrication of Encapsulated Gemini Surfactants.

(1) Background: Encapsulation of surfactants is an innovative approach that allows not only protection of the active substance, but also its controlled and gradual release. This is primarily used to protect metallic surfaces against corrosion or to create biologically active surfaces. Gemini surfactants are known for their excellent anticorrosion, antimicrobial and surface properties; (2) Methods: In this study, we present an efficient methods of preparation of encapsulated gemini surfactants in form of alginate and gelatin capsules; (3) Results: The analysis of infrared spectra and images of the scanning electron microscope confirm the effectiveness of encapsulation; (4) Conclusions: Gemini surfactants in encapsulated form are promising candidates for corrosion inhibitors and antimicrobials with the possibility of protecting the active substance against environmental factors and the possibility of controlled outflow.

Cationic gemini surfactant properties, its potential as a promising bioapplication candidate, and strategies for improving its biocompatibility: A review.

Gemini surfactants consist of two cationic monomers of a surfactant linked together with a spacer. The specific structure of a cationic gemini surfactant is the reason for both its high surface activity and its ability to decrease the surface tension of water. The high surface activity and unique structure of gemini surfactants result in outstanding properties, including antibacterial and antifungal activity, anticorrosion properties, unique aggregation behaviour, the ability to form various structures reversibly in response to environmental conditions, and interactions with biomacromolecules such as DNA and proteins. These properties can be tailored by selecting the optimal structure of a gemini surfactant in terms of the nature and length of its alkyl substituents, spacer, and head group. Additionally, regarding their properties, comparison with their monomeric counterparts demonstrates that gemini surfactants have higher performance efficacy at lower concentrations. Hence, less material is needed, and the toxicity is lower. However, there are some limitations regarding their biocompatibility that have led researchers to develop amino acid-based and sugar-based gemini surfactants. Owing to their remarkable properties, cationic gemini surfactants are promising candidates for bioapplications such as drug delivery systems, gene carriers, and biomaterial surface modification.

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

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.

Antimicrobial Activity of Gemini Surfactants with Azapolymethylene Spacer.

A series of 21 azapolymethylene gemini surfactants were obtained. The synthesis of the title surfactants in one- or two-step reaction proceeds with good yields. The structure and the purity of the synthesized compounds were determined by 1H and 13C NMR, ESI-MS spectra, and elemental analysis. Moreover, 2D COSY, HMBC, and HSQC spectra were performed. The minimal inhibitory concentrations (MIC) of the synthesized compounds were determined against fungi: Candida albicans, Aspergillus niger, Penicillium chrysogenum and bacteria: Escherichia coli,Pseudomonas aeruginosa, Staphylococcus aureus, and Bacillus subtilis. Also, the critical micelle concentrations (CMC) were determined. The relationship between antimicrobial and surface activity and surfactant structure has been determined.

The biodegradation of monomeric and dimeric alkylammonium surfactants.

Quaternary ammonium compounds (QACs) are salts known for having antiseptic and disinfectant properties. These compounds are toxic to aquatic organisms and should thus be removed from wastewater before its discharge into surface waters. The biodegradation of QACs takes place in the presence of microorganisms under aerobic conditions. The susceptibility of these compounds to degradation depends on numerous parameters. A number of them, such as the structure-adsorption on solids, and concentration of the QACs, as well as the presence of additional substances, have been reviewed in this article. Moreover, the biodegradability of new dimeric alkylammonium salts, i.e., cationic gemini surfactants, has been discussed and compared with that of anionic and nonionic geminis. The biodegradation study of monomeric and dimeric alkylammonium surfactants show that they are not easily degraded. The degradation process is very complex and strongly depends on the structure of the compound, adsorption-desorption processes on sludge, type of microorganism consortia and the presence of anions. Alkylammonium surfactants with biological motifs, like amide, peptides or carbohydrates, are much better degraded.

Gemini alkyldeoxy-D-glucitolammonium salts as modern surfactants and microbiocides: synthesis, antimicrobial and surface activity, biodegradation.

Dimeric quaternary alkylammonium salts possess a favourable surface and antimicrobial activity. In this paper we describe synthesis, spectroscopic analysis, surface and antimicrobial activity as well as biodegradability of polymethylene-α,ω-bis(N,N-dialkyl-N-deoxy-D-glucitolammonium iodides), a new group of dimeric quaternary ammonium salts. This new group of gemini surfactants can be produced from chemicals which come from renewable sources. The structure of products has been determined by the FTIR and (1)H and (13)C NMR spectroscopy. The biodegradability, surface activity and antimicrobial efficacy against Escherichia coli, Staphylococcus aureus, Candida albicans, Aspergillus niger and Penicillium chrysogenum were determined. The influence of the number of alkyl chains and their lengths on surface and antimicrobial properties has been shown. In general, dimeric quaternary alkyldeoxy-D-glucitolammonium salts with long alkyl substituents show favourable surface properties and an excellent antimicrobial activity.

Study of cyclic quaternary ammonium bromides by B3LYP calculations, NMR and FTIR spectroscopies.

N,N-dioctyl-azepanium, -piperidinium and -pyrrolidinium bromides 1-3, have been obtained and characterized by FTIR and NMR spectroscopy. DFT calculations have also been carried out. The optimized bond lengths, bond angles and torsion angles calculated by B3LYP/6-31G(d,p) approach have been presented. Both FTIR and Raman spectra of 1-3 are consistent with the calculated structures in the gas phase. The screening constants for 13C and 1H atoms have been calculated by the GIAO/B3LYP/6-31G(d,p) approach and analyzed. Linear correlations between the experimental 1H and 13C chemical shifts and the computed screening constants confirm the optimized geometry.