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).
Enhanced aqueous solubility of polycyclic aromatic hydrocarbons by green diester-linked cationic gemini surfactants and their binary solutions
Panda, Manorama,Fatma, Nazish,Kabir-Ud-Din
, p. 109 - 116 (2016)
Three homologues of a novel biodegradable diester-linked cationic gemini surfactant series, CmH2m+1 (CH3)2N+(CH2COOCH2)2N+(CH3)2CmH2m+1.2Cl- (m-E2-m; m = 12, 14, 16), were used for investigation of the solubilization of polycyclic aromatic hydrocarbons (PAHs) such as naphthalene, anthracene and pyrene in single as well as binary surfactant solutions. Physicochemical parameters of the pure/mixed systems were derived by conductivity and surface tension measurements. Dissolution capacity of the equimolar binary surfactant solutions towards the PAHs was studied from the molar solubilization ratio (MSR), micelle-water partition coefficient (Km) and free energy of solubilization (ΔGs0) of the solubilizates. Influence of hydrophobic chain length of the dimeric surfactants on solubilization was characterized. Aqueous solubility of the PAHs was enhanced linearly with concentration of the surfactant in all the pure and mixed gemini-gemini surfactant systems.
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.
Ester-bonded cationic gemini surfactants: Assessment of their cytotoxicity and antimicrobial activity
Fatma, Nazish,Panda, Manorama,Kabir-ud-Din,Beg, Muheeb
, p. 390 - 394 (2016)
We have assessed the biological properties such as cytotoxicity and antimicrobial activity of a series of biocompatible ester-linked cationic gemini surfactants, ethane-1,2-diyl bis(N, N-dimethyl-N-alkylammoniumacetoxy) dichlorides (m-E2-m, m?=?12, 14, 16). The effect of alkyl chain length (12, 14 and 16 carbon atoms) on their antimicrobial activity and cytotoxicity was examined. Antimicrobial activity of m-E2-m, against various prokaryotic and eukaryotic microorganisms, was studied by measuring the diameter of inhibition zone whereas cytotoxicity was evaluated using 3T3-L1 fibroblast cells. Toxic effect against these cells depends upon the type of the target microorganisms, nature of the cells, and hydrophobicity of the molecules. Antimicrobial activity of the gemini surfactant 16-E2-16 is lower than that of its corresponding single-chain counterpart. The gemini surfactants used for the present study (m-E2-m) which have excellent surface properties and much lower cmc values show low toxicity and significant antimicrobial activity.
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.
Mixed micellization of novel cationic ester-bonded gemini surfactants: Investigations by conductometric and tensiometric measurements
Fatma, Nazish,Panda, Manorama,Kabir-ud-Din
, p. 959 - 966 (2016)
The micellization and interfacial properties of three homologous dicationic ester-bonded cleavable and biodegradable gemini surfactants, ethane-1,2-diyl bis(N,N-dimethyl-N-alkylammoniumacetoxy) dichlorides, referred as m-E2-m (m = 12, 14, 16), and their binary mixtures were investigated in aqueous solution by performing conductivity and surface tension measurements. The decrease in critical micelle concentration (CMC) indicates nonideality of the mixed systems of different compositions. The unequal hydrophobic chain length might be playing a significant role in the reduction of CMC values. Several theoretical treatments were used to analyze and compare the mutual interaction parameters, counter ion binding, surface parameters, excess free energy of micellization and standard free energies for the mixed surfactant systems as well. The negative values of interaction parameters show an overall attractive force, i.e., synergistic effect in the mixed state. The excess free energy of mixing has negative values for all the systems.
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.
Mixed micellization behavior of Gemini (Cationic Ester-Bonded) surfactants with conventional (Cationic, Anionic and Nonionic) surfactants in aqueous medium
Fatma, Nazish,Ansari, Wajid Husain,Panda, Manorama,Kabir-Ud-Din
, p. 133 - 149 (2013)
Two cationic ester-bonded cleavable gemini surfactants of different hydrophobic chain length ethane-1,2-diyl bis(N,N-dimethyl-N- alkylammoniumacetoxy)dichloride, CnH2n+1 (CH 3)2N+ (CH2COOCH2) 2N+(CH3)2CnH2n+1. 2Cl- (n-E2-n, n = 12, 16), having ester linkage in the spacer, were synthesized adopting the reported procedure. Physicochemical properties of the single and binary gemini-conventional mixed micelles of different mole fractions were studied by conductivity measurements at 30°C. The conventional surfactants used were: DTAC (dodecyltrimethylammonium chloride), CTAC (hexadecyltrimethylammonium chloride), CPC (cetylpyridinium chloride), SDS (sodium dodecyl sulfate), SDBS (sodium dodecylbenzene sulfonate), TX-100 (t-octylphenoxypolyethoxyethanol) and Brij 58 (polyoxyethylene (20) cetyl ether). Whereas the critical micelle concentration (cmc) values for the dicationic geminis (12-E2-12 and 16-E2-16) were found to be very low as compared to the respective monomeric surfactant with the same number of carbon atoms in the hydrophobic chain per hydrophilic head group, those for all the binary systems were found to be less than the ideal cmc values studied at different mole fractions of the geminis. This synergistic interaction between the surfactants has been analyzed in the light of various theoretical models such as Clint, Rubingh, Motomura and Maeda. by Oldenbourg Wissenschaftsverlag, Mu?nchen.
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.
Preparation method of tetra-ester gemini quaternary ammonium salt leather sterilization mildew inhibitor
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Paragraph 0016; 0021, (2021/07/31)
The invention discloses a preparation method of a tetra-ester gemini quaternary ammonium salt leather sterilization mildew inhibitor. The preparation method comprises the following steps: firstly, taking hydroxyl-terminated diol and chloroacetyl chloride as reactants, and synthesizing ester dichloride through nucleophilic substitution reaction; then carrying out nucleophilic substitution reaction on the ester group dichloride and diethylamine to synthesize ester group di-tert-amine; then using fatty alcohol and bromoacetyl bromide as reactants to synthesize bromoacetate through acylation reaction; and finally, carrying out quaternization reaction on the obtained bromoacetate and ester group di-tert-amine to obtain the tetra-ester gemini quaternary ammonium salt bactericidal mildew inhibitor, and respectively distributing ester groups on a spacer group and a hydrophobic chain of the gemini quaternary ammonium salt. The tetra-ester gemini quaternary ammonium salt leather sterilization mildew inhibitor prepared by the method has good antibacterial and mildew-proof performance, can be applied to the sterilization and mildew-proof field of leather, and has a good market application prospect.
