6941-69-1Relevant articles and documents
Environment-friendly ester bonded gemini surfactant: Mixed micellization of 14-E2-14 with ionic and nonionic conventional surfactants
Fatma, Nazish,Panda, Manorama,Ansari, Wajid Husain,Kabir-Ud-Din
, p. 247 - 255 (2015)
Abstract This paper deals with a comprehensive study of the biodegradability, cleavability, hemolytic activity, and physicochemical properties of an ester-linked gemini surfactant, ethane-1,2-diyl bis(N,N-dimethyl-N-tetradecylammoniumacetoxy) dichloride (14-E2-14), along with the gemini-conventional mixed surfactant systems at different mole fractions of 14-E2-14. Some typical conventional surfactants of different polarities were used in the investigation at 303.15 K in aqueous medium by performing conductometric and tensiometric measurements. The data from both the techniques were used to obtain the critical micelle concentration (cmc) of mixed surfactant systems at different mole fractions. The decrease in cmc values indicates nonideality of the binary systems, and also occurrence of mixed micellization. Interaction parameters (βm and βσ) along with energetics of mixed micellization were evaluated by using theoretical models suggested by Clint, Rubingh, Rosen, Motomura and Maeda for mixed surfactant systems. Negative values of β indicate an overall attractive force in the mixed state. Also, the excess free energy of mixing has negative values for all the systems. The hydrophilic spacer of the gemini surfactant 14-E2-14 shows strong interaction with the conventional surfactants used as well as with the biological membranes such as human erythrocytes (RBC).
Self-aggregation of surfactant ethane-1,2-diyl bis(N, N -dimethyl- N -hexadecylammoniumacetoxy) dichloride: Tensiometric, microscopic, and spectroscopic studies
Akram, Mohd.,Bhat, Imtiyaz Ahmad,Kabir-Ud-Din
, p. 3499 - 3509 (2015)
We have investigated the effect of salt additives (NaCl, Na2SO4, Na3PO4, NaTos, and NaAn) on the aggregation behavior of a cleavable biodegradable ester-bonded dicationic gemini surfactant, ethane-1,2-diyl bis(N,N-dimethyl-N-hexadecylammoniumacetoxy) dichloride (16-E2-16). A multitechnique approach employing tensiometry, fluorescence, proton magnetic resonance (1H NMR), transmission electron microscopy (TEM), absorption spectrophotometry (UV), and Fourier transform infrared spectroscopy (FTIR) was utilized to probe physicochemical fluctuations. Appreciable changes were observed in various physicochemical parameters, viz., critical micelle concentration (CMC), surface excess concentration (Δmax), minimum area per headgroup (Amin), free energy of micellization (ΔGmic°), free energy of adsorption (ΔGads°), and aggregation number (Nagg). Counter ions were found to affect through electrostatic and hydrophobic influence obeying the overall trend as NaAn > NaTos > Na3PO4 > Na2SO4 > NaCl. 1H NMR, TEM, UV, and FTIR results reveal microstructure evolution and phase transitions. These results thus provide deeper insights in understanding of self-aggregation and microstructure evolution of biocompatible (green) aqueous systems of the gemini surfactant and their implications in the biomedical and pharmaceutical world, which could be helpful to improve their bioavailability and other biochemical aspects like drug delivery and gene transfection.
New insights into binding interaction of novel ester-functionalized m-E2-m gemini surfactants with lysozyme: A detailed multidimensional study
Akram, Mohd,Bhat, Imtiyaz Ahmad,Kabir-Ud-Din
, p. 102780 - 102794 (2015)
In this article fluorescence spectroscopy, UV-visible spectroscopy, circular dichroism (CD), isothermal titration calorimetry (ITC), transmission electron microscopy (TEM) and molecular docking methods have been used to examine the interaction between dicationic ester-bonded gemini surfactants (m-E2-m) and hen egg white lysozyme (HEWL). The fluorescence and UV-visible absorption spectral measurements indicate m-E2-m-HEWL complex formation via static procedure. Binding isotherms reveal mainly cooperative binding of m-E2-m surfactants to HEWL. Circular dichroism, and pyrene fluorescence depict conformational changes in HEWL upon m-E2-m combination. Synchronous fluorescence shows that addition of m-E2-m has a remarkable effect on the micropolarity of aromatic residues (Tyr/Trp) of HEWL. Far-UV CD spectra demonstrate that the α-helical network of HEWL is disrupted and its content decreases from 30.68% to 20.83%/20.40%, respectively, upon 12-E2-12/14-E2-14 combination. ITC confirms the endothermicity of m-E2-m-HEWL interactions while slight exothermicity was observed in the 14-E2-14-HEWL system at higher molar ratios of surfactant. TEM micrographs reveal structural change in HEWL upon m-E2-m addition. Molecular docking illustrates that 14-E2-14 binds principally near to predominant fluorophores of lysozyme viz. Trp-108 and Trp-62 while 12-E2-12 binds in proximity of Trp-123. This study provides an important insight, particularly the contribution of Trp-123 in the fluorescence besides already known predominant fluorophores, Trp-62 and Trp-108. Moreover, this study would be significant in context of protein-surfactant interactions in terms of special m-E2-m molecular structure, which is essential in determining their future use as excipients in pharmaceutical/drug delivery related compilations.
Molecular interaction of an ester-functionalized biodegradable gemini surfactant with lysozyme: Insights from spectroscopy, calorimetry and molecular docking
Akram, Mohd.,Bhat, Imtiyaz Ahmad,Anwar, Sana,Ud-Din, Kabir
, p. 641 - 649 (2015)
Designing and compilation of novel chemical molecules to optimize the structural characteristics of biomolecules is an interesting and fascinating domain of research at the interface of chemistry and molecular biology. In this context, we have synthesized a green/biocompatible gemini surfactant, ethane-1, 2-diyl bis(N,N-dimethyl-N-hexadecylammoniumacetoxy) dichloride (16-E2-16), and examined its interaction with the model enzyme hen egg white lysozyme (HEWL) utilizing sophisticated spectroscopic, microscopic, calorimetric and molecular modeling techniques. The results obtained through multidimensional approach demonstrate that 16-E2-16 is able to influence the structural aspects of HEWL. The intrinsic fluorescence and UV spectroscopic results reflect HEWL-16-E2-16 complex formation. Synchronous, three-dimensional and pyrene fluorescences show substantial changes in microenviroment around tyrosine and tryptophan residues. CD results demonstrate conformational change in HEWL upon 16-E2-16 combination. ITC suggests the contribution of hydrophobic forces and spontaneous nature of 16-E2-16-HEWL interaction. Molecular modeling confirms the binding of 16-E2-16 gemini surfactant near predominant fluorophores (Trp-62/Trp-108). TEM micrographs infer structural changes in HEWL. This study is thought to have good potential to help scientists to further interpret the surfactant-HEWL interaction at the molecular level, which will be significant to compile surfactant-protein mixtures in general for pharmaceutical and industrial purposes.
Interaction between DNA and cationic diester-bonded Gemini surfactants
Yaseen, Zahid,Rehman, Sayeed Ur,Tabish, Mohammad,Kabir-Ud-Din
, p. 322 - 327 (2014)
The formation of the polyion-complex between three cationic diester-bonded Gemini surfactants and DNA has been demonstrated systematically. This was studied through the electrostatic attraction between ammonium head groups of Gemini surfactants and the phosphate groups of DNA. Ethidium bromide exclusion assay indicates the interaction between DNA and diester-bonded Gemini surfactants. DNA binding abilities with the Gemini surfactant depends on tail length which has been demonstrated by agarose gel electrophoresis and circular dichroism (CD) measurements. Dynamic light scattering measurements reveal that the ester-bonded Gemini surfactants can induce the collapse of DNA into densely packed bead-like structures with smaller size. Molecular docking technique was also utilized to understand the mode and mechanism of interaction between DNA and the Gemini surfactants (pre-micellar form). In addition to electrostatic interactions between the negatively charged phosphate backbone of DNA and positively charged head groups of Gemini surfactants, self-association due to hydrophobic interactions between the alkyl tails of surfactant and the hydrogen bonding between the ester group of surfactant and nucleotide bases, result in the compaction of nucleotides.
The influence of various solvents on the interaction between gemini surfactant (ester-bonded) and imipramine hydrochloride: An aggregational, interfacial, and thermodynamic study
Asiri, Abdullah M.,Khan, Farah,Rub, Malik Abdul
, (2021/06/07)
In this study, aggregation, air/solvent interfacial surfaces and thermodynamic characteristics of the mixture of antidepressant drug imipramine hydrochloride (IMP) and ester-bonded gemini surfactant (ethane-1, 2-diyl bis(N,N-dimethyl-N-cetylammoniumacetoxy) dichloride (16-E2-16)) with different mole fractions (α1) of 16-E2-16 were explored through tensiometry technique at a temperature of 298.15 K. IMP is used to treat depression (antidepressant). The effect of several solvents (50 mmol·kg?1 NaCl, 500 mmol·kg?1 urea (U), and 500 mmol·kg?1 thiourea (TU)) other than the aqueous system on the interaction between IMP and 16-E2-16 were also explored. In aqueous system, the interactions between IMP and 16-E2-16 were estimated using UV–visible and FT-IR spectroscopy. Although the 16-E2-16 surfactant is biodegradable and IMP is used to treat depression, both ingredients are cationic. Tensiometric measurements that attained the critical micelle concentration (cmc) value of mixtures (IMP + 16-E2-16) were significantly less compared with the ideal cmc (cmcid) value. This confirmed a fair interaction between IMP and 16-E2-16 and that the interaction rises through a surge in α1 of 16-E2-16. In NaCl solvent, the attained cmc values of entire pure and mixed systems were less than with the aqueous system, whereas in U or TU solvent, the respective systems cmc values were more than with the aqueous system. U was found to be less effective than TU. Diverse parameters of aggregation and air/solvent interfacial and thermodynamic characteristics have been determined using Clint, Motomura, Rubingh, Rosen, etc. theoretical models. The activity coefficients parameter of micellar on air/solvent interfacial surfaces were regularly below 1 for each component, demonstrating the intermolecular interaction among components and non-ideal behavior of the mixed system. Akin to the tensiometric technique, UV–visible and FT-IR examination characterize the straightforward interaction between IMP and 16-E2-16. Overall, the obtained outcomes indicate an open method to design ester-bonded gemini surfactants to be proficient ingredients for the drug delivery vehicle.
Rational design, synthesis and evaluation of new azido-ester structures as green energetic plasticizers
Fareghi-Alamdari, Reza,Sheibani, Nasser,Zohari, Narges
supporting information, p. 12695 - 12706 (2020/10/02)
Computer-aided molecular design (CAMD) is a well-known tool for the theoretical assessment of chemical structures before their experimental synthesis. In this study, we used this method to consider the important criteria for a chemical structure as an energetic plasticizer for an energetic azido binder. The number of new azido-ester structures were initially designed, and their physicochemical and energetic properties were determinedviatheoretical calculation by molecular dynamics simulations and machine learning-based methods. Considering the balances between several criteria, two of these theoretical chemical structures (including GTAA (glyceryl tris(azidoacetate)) and TEGBAA (triethyleneglycol bis(azidoacetate))) were then selected, synthesized, and characterized. The comparison of experimental and theoretical results to evaluate the physicochemical properties of these new azido-ester plasticizers showed an acceptable agreement between the two methods. Finally, the compatibility and efficiency of these two new azido-ester plasticizers on the rheological and thermal properties of glycidyl azide polymer (GAP) were investigated using rheometry and DSC analyses, and compared with some common energetic plasticizers. The results confirmed that these two new azido-esters are appropriate plasticizers for GAP since they exhibited higher safety over comparable plasticizers, in addition to the real performance.
