Synthesis of Gemini Surfactants and Evaluation of Their Interfacial and Cytotoxic Properties: Exploring the Multifunctionality of Serine as Headgroup

Silva, Sandra G.; Alves, Cláudia; Cardoso, Ana M.; Jurado, Amália S.; Lima, Maria C. Pedroso de; Vale, M. Luísa C. do; Marques, Eduardo F.

doi:10.1002/ejoc.201201396

Cited by 43 publications

(15 citation statements)

References 44 publications

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“…The higher value of Π CMC is achieved by surfactant with the longer hydrophobic spacer – 8–9–8. It confirms the general trend that increasing the hydrophobic chain length causes the surfactant to reduce the surface tension to a greater extent (Mohamed et al, ; Silva et al, ). Results show that the area per molecule at the aqueous solution/air interface – a x for the surfactants investigated stays constant for surfactant with spacer s = 6, 7, and 8.…”

Section: Resultssupporting

confidence: 86%

Antimicrobial and Cytotoxic Properties of Bisquaternary Ammonium Bromides of Different Spacer Length

Łudzik

Kustrzepa

Kowalewicz-Kulbat

et al. 2018

J Surfact & Detergents

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A group of cationic gemini surfactants (bisquaternary ammonium bromides) with different spacer chain lengths (8-6-8, 8-7-8, 8-8-8, 8-9-8) was investigated, paying special attention to antimicrobial and the cytotoxic properties as well as their antimicrobial activity during long-term storage. It was shown that the compounds investigated exhibit excellent antimicrobial activity against Gram-positive bacteria (Staphylococcus aureus) and Gramnegative bacteria (Pseudomonas aeruginosa) as well as antifungal properties (Candida albicans). The gemini surfactants tested had the differential level of cytotoxicity against normal lymphocytes. It was shown that the spacer chain length plays an important role in antibacterial activity and influences the cytotoxicity. The gemini surfactants with shorter spacer chain length, that had higher critical micelle concentration, showed generally weaker antibacterial properties, but on the other hand, these exhibited lower level of cytotoxicity. Furthermore, the aqueous solution of gemini surfactants exhibited the same antimicrobial activity even after 3 months.Keywords Antibacterial properties Á Fungicide Á Cytotoxicity Á Bisquatenary ammonium bromides Á Application of gemini surfactants J Surfact Deterg (2018) 21: 91-99.

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Section: Resultssupporting

confidence: 86%

Antimicrobial and Cytotoxic Properties of Bisquaternary Ammonium Bromides of Different Spacer Length

Łudzik

Kustrzepa

Kowalewicz-Kulbat

et al. 2018

J Surfact & Detergents

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“…The lower value of γ CMC is achieved by the cationic silicone surfactants SiQC 17 Cl and SiQC 15 Cl with the longer hydrophobic carbon chains. It confirms the general trend that increasing the hydrophobic chain length causes the surfactant to reduce the surface tension to a greater extent (Silva et al, ). Comparison with the structure of SiQC 17 Cl and D1821 indicates that a flexible SiOSi group in SiQC 17 Cl enables the methyl groups to orient in low‐energy configurations, with a higher surface activity (Schmaucks et al, ).…”

Section: Resultssupporting

confidence: 86%

Synthesis, Surface Properties, and Antibacterial Activity of Novel Ester‐Containing Cationic Silicone Surfactants and Their Utilization as Fabric‐Finishing Agents

Wei

Cheng

Zhang

et al. 2018

J Surfact & Detergents

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In this study, a series of cationic silicone surfactants SiQC n Cl containing ester groups and double longchain alkyls (n = 9, 11, 13, 15, and 17) were synthesized by microwave irradiation and characterized using infrared Fourier transform (FTIR), 1 H nuclear magnetic resonance ( 1 H NMR), and thermogravimetric analysis (TGA). Surface activity and adsorption of these surfactants were investigated by measuring the equilibrium surface tension. The critical micelle concentration (CMC) decreased with increasing alkyl length of SiQC n Cl at 25 C and so did the corresponding surface tension at the CMC (γ CMC ). The aggregation behavior in aqueous solutions was also investigated systemically through transmission electron microscopy (TEM) and dynamic light scattering (DLS). Spherical or ellipsoidal-like aggregates with diameters ranging from 300 to 900 nm were observed. It is also shown that the cationic silicone surfactants exhibit certain antibacterial properties against Staphylococcus aureus but slightly poor to Escherichia coli. The morphological structure of SiQC 15 Cl-treated cotton fabrics was observed using scanning electron microscopy (SEM), which showed that the surface became neat and smooth. What is more, the finished cotton fabrics maintained some antibacterial properties with improved softness, which may provide a more comfortable and healthy lifestyle. This work may also be helpful to the design and application of functional cationic silicone surfactants. Keywords Cationic silicone surfactants Á Ester bonds Á Aggregation behavior Á Performance test Á Fabric finishing J Surfact Deterg (2019) 22: 285-299. The morphologies of the aggregates for SiQC n Cl in aqueous solutions (10 mmol L −1 ) were examined via a JSM-7001F TEM (JEOL, Japan) at 20 kV. The samples were 286 J Surfact Deterg J Surfact Deterg (2019) 22: 285-299

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“…In addition, GS can be synthesized fairly easily and at low cost, therefore making them advantageous from a pharmaceutical industrial manufacturing and economical perspective (Zana and Xia, 2004). Cationic serine-based GSs have enhanced interfacial properties and low cytotoxicities, offering potential use in technical and biological applications (Silva et al, 2013).…”

Section: Gemini Surfactantsmentioning

confidence: 99%

Surfactants: Pharmaceutical and Medicinal Aspects

Sekhon¹

2013

JPTRM

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Surfactants are amphipathic substances with lyophobic and lyophilic groups and are critical components in pharmaceutical products. Surfactants have several uses in pharmaceuticals, i) for solubilisation of hydrophobic drugs in aqueous media, ii) as components of emulsions ,iii) surfactant self-assembly vehicles for oral and transdermal drug delivery, iv) as plasticizers in semisolid delivery systems, and v) as agents to improve drug absorption and penetration. Non-ionic surfactants such as ethers of fatty alcohols are most commonly used in pharmaceuticals. Cationic surfactants are capable of exerting antibacterial properties by disrupting bacterial cell membranes. In pharmaceutical processing, phospholipid lecithin, bile salts, certain fatty acids and their derivatives have become indispensable since they afford a uniquely effective and efficient mechanism of drug carriage by solubilising the drugs of fatty origin. The antibacterial, antifungal and antiviral activities make biosurfactants relevant molecules for applications in combating many diseases and as therapeutic agents. Biosurfactants have the potential for use as major immunomodulatory molecules, as anti-adhesive biological coating for biomaterials, in vaccines and gene therapy, and they may be incorporated into probiotic preparations to combat urogenetical tract infections and pulmonary immunotherapy. Gemini surfactants are effective potential transfection agents for non-viral gene therapy. Ionic liquids act as secondary surfactants and the use of surfactant/ionic liquid systems should be explored to build specific properties in the organized medium, and to explore pharmaceutical applications of traditional, biosurfactant and Gemini surfactants.

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Synthesis of Gemini Surfactants and Evaluation of Their Interfacial and Cytotoxic Properties: Exploring the Multifunctionality of Serine as Headgroup

Cited by 43 publications

References 44 publications

Antimicrobial and Cytotoxic Properties of Bisquaternary Ammonium Bromides of Different Spacer Length

Antimicrobial and Cytotoxic Properties of Bisquaternary Ammonium Bromides of Different Spacer Length

Synthesis, Surface Properties, and Antibacterial Activity of Novel Ester‐Containing Cationic Silicone Surfactants and Their Utilization as Fabric‐Finishing Agents

Surfactants: Pharmaceutical and Medicinal Aspects

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