Gemini Imidazolium Surfactants: Synthesis and Their Biophysiochemical Study

Kamboj, Raman; Singh, Sukhprit; Bhadani, Avinash; Kataria, Hardeep; Kaur, Gurcharan

doi:10.1021/la300920p

Cited by 119 publications

(85 citation statements)

References 72 publications

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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: 52%

“…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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confidence: 52%

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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“…The first breakpoint is due to the formation of premicelles in dilute solutions, while the second breakpoint is the CMC. The existence of premicellar aggregates at low concentration has been previously investigated by several research groups [20][21][22]. Zana has reported that premicellar aggregation is observed in solutions of gemini surfactants with a long alkyl chain of at least 14 carbon atoms [19].…”

Section: Resultsmentioning

confidence: 99%

Lysine-based oligomeric surfactants with cyanuric chloride: synthesis and micellization properties

Liang

et al. 2015

Colloid Polym Sci

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Two lysine-based oligomeric surfactants 2C 12 LyNa 2 and 3C 12 LyNa 3 were synthesized using cyanuric chloride and N ε -lauroyl-L-lysine. Their physicochemical properties of aqueous solutions were determined by surface tension and conductivity as well as dynamic light scattering (DLS) and transmission electron microscopy (TEM) measurements. From the results of surface tension and conductivity measurements, the critical micelle concentration decreases by one order of magnitude with increasing degree of oligomerization. 3C 12 LyNa 3 and 2C 12 LyNa 2 tend to form premicellar aggregates in solution at a sufficiently low concentration. In addition, their interface behaviors such as adsorption and micellization are reflected by parameters such as the minimum surface area per molecule (A min ), adsorption efficiency and effectiveness (pC 20 ), maximum surface excess concentration (Γ max ), and standard free energy for micellization and adsorption (ΔG mic ∘ , ΔG ads°) . The A min value of 2C 12 LyNa 2 and 3C 12 LyNa 3 is two times that of the monomeric surfactant sodium N ε -lauroyl-L-lysine (C 12 LyNa). With increasing degree of oligomerization, pC 20 increases, which follows the reverse order for ΔG mic°a nd ΔG ads°. TEM results showed that C 12 LyNa forms slightly entangled rod-like micelles. 2C 12 LyNa 2 and 3C 12 LyNa 2 can self-assemble into regular spherical assemblies; DLS showed that with increasing degree of oligomerization for 2C 12 LyNa 2 and 3C 12 LyNa 3 , the diameters of the spherical aggregates decrease and the hydrophobic interaction and hydrogen bonding become stronger.

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“…Topological aspects of the condensed complexes have been analyzed by scanning microscopy, such as AFM [91,98]. Other methods as surface tension [99,100], FTIR [96,101], UV-vis [91,102], and some others have been also used to analyze additional aspects of the complexes in the absence of cells.…”

Section: Biophysical Methodsmentioning

confidence: 99%

Recent progress in gene therapy to deliver nucleic acids with multivalent cationic vectors

Junquera

Aicart

2016

Advances in Colloid and Interface Science

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Gemini Imidazolium Surfactants: Synthesis and Their Biophysiochemical Study

Cited by 119 publications

References 72 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

Lysine-based oligomeric surfactants with cyanuric chloride: synthesis and micellization properties

Recent progress in gene therapy to deliver nucleic acids with multivalent cationic vectors

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