Synthesis and evaluation of micellar properties and antimicrobial activities of imidazole‐based surfactants

Kanjilal, Sanjit; Sadula, Sunitha; Reddy, P. Srinivasa; Kumar, K. Praveen; Murty, U. S. N.; Prasad, R. B. N.

doi:10.1002/ejlt.200800292

Cited by 54 publications

(49 citation statements)

References 13 publications

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“…Baker et al [13] synthesized and evaluated micellar properties of a new class of N-alkyl-N-methylpyrrolidinium ILs. Previously, we have synthesized imidazolium-based monocationic surfactant with an ester and/or amide functional group in the hydrophobic chain [14]. Evaluation of these compounds confirmed them to be soft bioactive and surface active compound.…”

Section: Introductionmentioning

confidence: 91%

“…The hydroxyl group of benzyl alcohol derivative was converted to bromo by the treatment of PBr 3 in chloroform for 4 h at RT (308C) to afford 4-alkyloxy benzyl bromide (5) in 70% yield. The quaternization of N-methyl imidazole with 5 in acetone under refluxing conditions for 24 h afforded the final imidazoliumbased monocationic surfactant (6) in 60% isolated yield [14].…”

Section: Synthesismentioning

confidence: 99%

“…For the synthesis of monocationic surfactant, 4-alkyloxy benzyl bromide is quaternized with N-methylimidazole [14]. Gemini surfactants are synthesized by initial coupling of imidazole to 4-alkyloxy benzyl bromide according to a reported procedure [18].…”

Section: Synthesismentioning

confidence: 99%

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Synthesis and evaluation of new imidazolium‐based aromatic ether functionalized cationic mono and gemini surfactants

Sadula

Reddy

Kanjilal

2011

Eur. J. Lipid Sci. Technol.

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Synthesis of a novel series of imidazolium-based surfactants, [(ROArCH 2 MIm)Br] with aromatic ether functionalized hydrophobic tail of varying chain lengths and also their gemini counterparts were conducted in the present work. Synthesis involves initial conversion of 4-hydroxy benzoic acid to its methyl ester followed by its O-alkylation with long chain fatty alcohols, which was subsequently reduced and brominated to get 4-alkyloxy benzyl bromide. For the synthesis of monocationic surfactant, 4-alkyloxy benzyl bromide is quaternized with N-methylimidazole. Gemini surfactants are synthesized by initial coupling of imidazole to 4-alkyloxy benzyl bromide followed by its quaternization with dibromoalkane. The surface properties of all the synthesized surfactants were determined using surface tensiometry. Within the same homologous series, expected decrease in critical micelle concentration (cmc) with the increase in hydrophobicity was observed for shorter chain homologs. However, the deviation in cmc value from regularity was observed when the number of carbon atoms in the hydrophobic chain exceeded a certain number. The cmc values of the geminis were found to be remarkably low compared to their monomeric counterparts.

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Section: Introductionmentioning

confidence: 91%

Section: Synthesismentioning

confidence: 99%

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Synthesis and evaluation of new imidazolium‐based aromatic ether functionalized cationic mono and gemini surfactants

Sadula

Reddy

Kanjilal

2011

Eur. J. Lipid Sci. Technol.

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“…This type of stipulations can be fulfilled only when the degradable reactants used for the synthesis of ionic liquids or introduction of degradable functionality like amide or ester in to the moiety of the resulted product [1,2] or by synthesizing the ionic liquids with high surface activity and low Critical Micelle Concentrations (CMC) [3][4][5]. Ionic liquids (IL s ) have replaced traditional organic solvent, because of low vapor pressure [6,7], high thermal stability, nonflammability and capability to dissolve wide range of compounds [8,9].…”

Section: Introduction Bioactive Peptidesmentioning

confidence: 99%

Comparison of Physicochemical Studies of Single Tailed and Gemini Cyclohexanoxy Carbonyl Pyridinium Cationic Amphiphiles

Aggarwal¹

2017

J Proteomics Bioinform

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In the present research work, the physicochemical studies of surface active Cyclohexanoxy carbonyl Pyridinium single tailed and Gemini amphiphiles had been compared. Thermal stability, size of aggregates in aqueous system and interaction with a globular protein, Bovine Serum Albumin (BSA), was done by using TGA analysis, DLS, UV-visible, steady-state fluorescence and synchronous fluorescence and TEM respectively. On the basis of the experiments, it had been concluded that the Gemini amphiphile possessed less cytotoxicity, high thermally stability, form small sized compact aggregates and stable complex with BSA. The results have further been supported by higher value of Stern-Volmer quenching constant (K SV ) and a higher binding constants for Gemini amphiphiles as compared to single tailed amphiphiles. Moreover, on the basis of synchronous fluorescence spectra and UV spectra, it has been concluded that both the amphiphiles mainly interact with tryptophan residues. The less cytotoxicity values and stabilization of secondary structure of BSA in low concentration of ionic liquids implies that these ionic liquids can replaced the conventional surfactants in the detergent industries and used as a potential vehicles for the drug and gene delivery.the change in the wavelength of emission maximum (λ max ) and intensity parameters found to be sensitive to protein conformation and can be used to investigate the interactions between BSA and ionic liquids. DLS and TEM studies are used to see the change in conformation of the amphiphiles in the presence of BSA. Materials and Methods MaterialsGemini Amphiphiles (GA) and Single Tailed amphiphiles (ST) ( Figure 1) were synthesized in our lab by an earlier reported procedure [18,19]. Bovine Serum Albumin (BSA) (MW=66 kDa) was purchased from Central drug house (New Delhi, India) and was used as received. 0.01 M buffer, pH 7.2, was made from 0.01 M KH 2 PO 4 and 0.01 M sodium hydroxide. Potassium dihydrogen phosphate and sodium hydroxide were purchased from Merck, India. Millipore water was used in all experiments. Thermal gravimetric analysisThermal stability of both the amphiphiles had been investigated by Perkin Elmer Pyris 1 Thermal Gravimetric Analyzer (TGA). Both the samples were completely dried by rotatory vaccum pump. Both the samples were added in to the aluminum pans under the inert atmosphere at a heating rate of 10°C/min. Dynamic Light Scattering (DLS)The size of the studied cationic amphiphiles has been measured by the Zetasizer Nano ZS (Malvern Instrument Ltd.) UK. The inbuilt peltier device controls the temperature with an accuracy of ±0.1 K. The 1.0 mM aqueous solution of both amphiphiles has been filtered through 0.45 μM pore sized filter before measurement. CytotoxicityThe cytotoxicity of, 1.0 mM aqueous solution, both synthesized amphiphiles was carried out on C 6 glioma (cancerous brain cell line, passage number 65) by using MTT assay to calculate the IC 50 value of both the synthesized ionic liquids. Cells were seeded at a density of 10 × 10 3 cells/m...

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“…As propriedades favoráveis dos LIs estão presentes também naqueles que contém cadeias alquílicas longas, os líquidos iônicos tensoativos (LITs GENG et al, 2010;JUNGNICKEL et al, 2008;THOMAIER;KUNZ, 2007;WANG et al, 2010 (BALTAZAR et al, 2007;INOUE et al, 2007;KANJILAL et al, 2009), e C n MeImBF 6 (n = 12, 14, 16) (GORDON et al, 1998) .…”

Section: Líquidos Iônicos Tensoativosunclassified

Líquidos iônicos tensoativos: correlação entre estrutura molecular e propriedades micelares de cloretos de 1,3-dialquilimidazólio

Galgano¹

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The objective of this work is the synthesis and determination of the micelar properties of cationic surface-active ionic liquids (SAILs). Among the important characteristics of these compounds are: high charge delocalization and acid character of hydrogen H2 of the heterocyclic ring and large structural flexibility, the latter is relevant to solution properties of these surfactants, hence to their applications. Synthesis of SAILs was carried out by conventional heating or by microwave irradiation, the later method was more efficient. Initially, we studied the influence of the chain length of the alkyl group (an important factor for the energy of micelle formation) of 1-alkyl-3-methylimidazolium chlorides, n-alkyl group having 10 to 16 carbon atoms. Then, we compared the properties of the above mentioned SAILs with conventional surfactants, 1-alkylpyridinium chlorides and 1alkanoyl-amidoethyl benzyldimethylammonium chlorides. Finally, we studied the influence of the head-group volume, by studying 1-alkyl-3-hexadecylimidazolium chlorides, with secondary n-alkyl group having 1 to 5 carbon atoms. The micelar properties were investigated by surface tension, conductivity, calorimetry, light scattering and nuclear magnetic resonance. Our results have shown that hydrogen bonding (due to the acidic H2 of the imidazolium ring) and hydrophobic interactions are relevant to micelle formation; increasing the head-group volume favors micellization and the formation of pre-micellar aggregates.

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Synthesis and evaluation of micellar properties and antimicrobial activities of imidazole‐based surfactants

Cited by 54 publications

References 13 publications

Synthesis and evaluation of new imidazolium‐based aromatic ether functionalized cationic mono and gemini surfactants

Synthesis and evaluation of new imidazolium‐based aromatic ether functionalized cationic mono and gemini surfactants

Comparison of Physicochemical Studies of Single Tailed and Gemini Cyclohexanoxy Carbonyl Pyridinium Cationic Amphiphiles

Líquidos iônicos tensoativos: correlação entre estrutura molecular e propriedades micelares de cloretos de 1,3-dialquilimidazólio

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