Synthesis, characterization and comparative evaluation of phenoxy ring containing long chain gemini imidazolium and pyridinium amphiphiles

Bhadani, Avinash; Kataria, Hardeep; Singh, Sukhprit

doi:10.1016/j.jcis.2011.05.023

Cited by 70 publications

(61 citation statements)

References 48 publications

(75 reference statements)

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“…The introduction of ester functionality and Cyclohexyloxy in to the hydrophobic tail makes the compound less toxic. Furthermore, the present compounds have also found to be less toxic as compared to earlier synthesized Imidazolium and Pyridinium amphiphiles [3,4]. …”

mentioning

confidence: 51%

“…From the experimental statistics, it has been cleared that the Gemini amphiphiles possess reasonably good thermal stability as compare to their single tailed amphiphiles. Thermal stability of the compound has been affected by the number of factors like functional group present in the hydrophobic tail [22], heterocyclic moiety [23], symmetry of the cation [3] and size of anions [24]. Our experimental results bare that the Gemini analogue was more thermally stable as compared to single tailed amphiphiles (Table 1), due to the symmetry factors.…”

Section: Thermal Gravimetric Analysis (Tga)mentioning

confidence: 89%

“…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%

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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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mentioning

confidence: 51%

Section: Thermal Gravimetric Analysis (Tga)mentioning

confidence: 89%

Section: Introduction Bioactive Peptidesmentioning

confidence: 99%

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

Aggarwal¹

2017

J Proteomics Bioinform

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“…The cmc's for the Geminis were much lower than the cmc's of the mono imidazolium surfactants. Gemini imidazolium-based surfactants and pyridinium-based surfactants with thioether spacers have very recently been described and characterized [41,42].…”

Section: Association Structuresmentioning

confidence: 99%

Ionic Liquids and Polymeric Ionic Liquids as Stimuli-Responsive Functional Materials

Texter

2015

Applications of Ionic Liquids in Polymer Science and Technology

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“…Nowadays, the focus of researcher shifted to change the nature of the head group such as pyridinium [15][16][17], imidazolium [17][18][19], dimethyl and diethyl quaternary ammonium [20], pyrrolidinium [21], piperidinium [22] and amino acids [23][24][25] or architecture of alkyl tail part such as cholesterol [26][27][28][29], pyrenyl [30], esterquat [31] symmetrical and unsymmetrical alkyl tails [4]. However, spacer aspect of gemini surfactants mostly limited to change in its length [1,4,19,32].…”

Section: Introductionmentioning

confidence: 99%

Physico-biochemical studies on cationic gemini surfactants: Role of spacer

Parikh

Mistry

Jana

et al. 2015

Journal of Molecular Liquids

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Synthesis, characterization and comparative evaluation of phenoxy ring containing long chain gemini imidazolium and pyridinium amphiphiles

Cited by 70 publications

References 48 publications

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

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

Ionic Liquids and Polymeric Ionic Liquids as Stimuli-Responsive Functional Materials

Physico-biochemical studies on cationic gemini surfactants: Role of spacer

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