Biocidal and inhibitory activity screening of de novo synthesized surfactants against two eukaryotic and two prokaryotic microbial species

Tiecco, Marcello; Cardinali, Gianluigi; Roscini, Luca; Germani, Raimondo; Corte, Laura Della

doi:10.1016/j.colsurfb.2013.06.033

Cited by 30 publications

(23 citation statements)

References 56 publications

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“…However, it is also possible that more than one mechanism is responsible for interaction of the tested nanoemulsion and bacterial cells [40]. Tiecco et al tested antimicrobial activity of 36 quaternary ammonium salts, including 28 structurally different non-commercial surfactants [41]. In this group there were two sulfobetaines, which displayed reduced biocidal activity in comparison with other surfactants.…”

Section: Discussionmentioning

confidence: 99%

Surface and Antimicrobial Activity of Sulfobetaines

Wieczorek

Gwiazdowska

Staszak

et al. 2016

J Surfact & Detergents

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Sulfobetaines belong to the group of zwitterionic surfactants. They are electroneutral salts, which have in the same molecule, two ionic centers with different charge. Due to the specific structure they exhibit excellent properties such as good solubility in water and detergency. In this paper we present surface properties and adsorption parameters of sulfobetaines in water/air systems. From the adsorption isotherms the CMC value, the surface tension and surface pressure at the CMC as well as the efficiency of adsorption were determined. Physicochemical analyses of the data allowed for the further description of adsorption process. Results showed that sulfobetaines exhibit good surface properties especially low CMC and p20 values. Additionally the antimicrobial activity of sulfobetaines solutions against gram‐positive and gram‐negative bacteria were tested by the well‐diffusion method. MIC values and growth kinetics were determined by microdilution method. Antimicrobial assays demonstrated that sulfobetaines can be good antibacterial agents, but the activity of surfactants strongly depends on alkyl chain length.

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Section: Discussionmentioning

confidence: 99%

Surface and Antimicrobial Activity of Sulfobetaines

Wieczorek

Gwiazdowska

Staszak

et al. 2016

J Surfact & Detergents

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“…CTABr, TBABr, TPeABr, THeABr, TBPBr, CTBPBr, and SB3‐12 were purchased from Sigma‐Aldrich and recrystallized from acetone or ethyl acetate with different amounts of methanol before use. Other cationic surfactants and quaternary ammonium salts were synthesized by quaternization reaction of the correspondent tertiary amines with the appropriate alkyl halide or mesylate, following published procedures and purified by subsequent crystallizations from acetone, ethyl acetate, or acetonitrile with different amounts of methanol. CB1‐12 was synthesized by a literature procedure .…”

Section: Experimental Chemoinformatics and Materialsmentioning

confidence: 98%

“…Other cationic surfactants and quaternary ammonium salts were synthesized by quaternization reaction of the correspondent tertiary amines with the FIGURE 1 Families of tested compounds: general formulas for tetralkylammonium surfactants (I) (A), tetralkylammonium salts (B), tetraalkylammonium surfactants with endocyclic ammonium (I) (C), tetralkylammonium salts with endocyclic ammonium (D), twin chain (TC) (E), and sulfobetaines (SB) (F). For an exhaustive list, see the Supporting Information appropriate alkyl halide or mesylate, following published procedures [19][20][21][22] and purified by subsequent crystallizations from acetone, ethyl acetate, or acetonitrile with different amounts of methanol. CB1-12 was synthesized by a literature procedure.…”

Section: Chemical Productsmentioning

confidence: 99%

Chemoinformatic design of amphiphilic molecules for methane hydrate inhibition

Profio

Canale

Marvulli

et al. 2018

Journal of Chemometrics

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Cationic surfactants and other low molecular weight compounds are known to inhibit nucleation and agglomeration of methane hydrates. In particular, tetralkylammonium salts are kinetic hydrate inhibitors; ie, they reduce the rate of hydrate formation. This work relates to the in‐silico determination of structural features of molecules modulating methane hydrate formation, as found experimentally, and the prediction of novel structures to be tested as candidate inhibitors. Experimental data for each molecule are the amount of absorbed methane. By inserting these numerical values into a chemoinformatic model, it was possible to find a mutual correlation between structural features and inhibition properties. A maximum amount of information is extracted from the structural features and experimental variables, and a model is generated to explain the relationship therebetween. Chemometric analysis was performed by using the software package Volsurf+ with the aim of finding a primary correlation between surfactant structures and their properties. Experimental parameters (pressure, temperature, and concentration) were further processed through an optimization procedure. A careful study of the chemometric analysis responses and the numerical descriptors of tested surfactants allowed to define the features of a good inhibitor, as far as the amount of absorbed gas is concerned. An external prediction is finally made to project external compounds, whose structures and critical micellar concentration are known, in a statistical model, to predict the inhibition properties of a particular molecule in advance of synthesis and testing. This method allowed to find novel amphiphilic molecules for testing as candidate inhibitors in flow‐assurance.

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“…19,20,[36][37][38][39][40][41][42][43][44][45][46][47] In previous works, Kumar et al 19 found that elastic hydrogel was formed by the zwitterionic surfactant erucyl dimethyl amidopropyl betaine (EDAB, with an unsaturated C 22 tail) and Chu et al 20 also found that hydrogel was formed by concentrated 3-(N-erucamido-propyl-N,N-dimethyl ammonium) propane-sulfonate (EDAS, with an unsaturated C 22 tail) in the presence of NaCl. 19,20,[36][37][38][39][40][41][42][43][44][45][46][47] In previous works, Kumar et al 19 found that elastic hydrogel was formed by the zwitterionic surfactant erucyl dimethyl amidopropyl betaine (EDAB, with an unsaturated C 22 tail) and Chu et al 20 also found that hydrogel was formed by concentrated 3-(N-erucamido-propyl-N,N-dimethyl ammonium) propane-sulfonate (EDAS, with an unsaturated C 22 tail) in the presence of NaCl.…”

Section: Introductionmentioning

confidence: 99%

Formation and phase transition of hydrogel in a zwitterionic/anionic surfactant system

Fan

Zhao

et al. 2015

RSC Adv.

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The phase behavior and microstructure in a mixture of the zwitterionic surfactant N-hexadecyl-N,Ndimethyl-3-ammonio-1-propane sulfonate (HDPS) and anionic surfactant sodium dodecylsulfate (SDS) were studied. Analysis of its macroscopic appearance, tube inversion testing and rheological measurements were employed to characterize its phase behavior, and it was found that a hydrogel formed in an appropriate total concentration (C T ) and molar percentage of SDS (X SDS ) at 25 C for HDPS/ SDS systems. Microstructures in the hydrogel were identified to be long wormlike micelles and small spherical vesicles, using transmission electron microscopy (TEM). The coexistence of wormlike micelles and small vesicles brings an appropriate packing parameter (p), which indicates that the wormlike micelles reached a sufficient length and degree of entanglement to form the three-dimensional elastic hydrogel. The HDPS/SDS hydrogel transforms into a viscoelastic sol upon increasing the temperature, and the determined gel-sol transition temperature (T g-s ) has been determined to be around 30 C, using optical and rheological methods. Besides, adding salt causes the wormlike micelles to lengthen and the rheological properties of the solution to change, such that it may even induce a sol-gel phase transition in the mixed zwitterionic and anionic surfactant system.

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Biocidal and inhibitory activity screening of de novo synthesized surfactants against two eukaryotic and two prokaryotic microbial species

Cited by 30 publications

References 56 publications

Surface and Antimicrobial Activity of Sulfobetaines

Surface and Antimicrobial Activity of Sulfobetaines

Chemoinformatic design of amphiphilic molecules for methane hydrate inhibition

Formation and phase transition of hydrogel in a zwitterionic/anionic surfactant system

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