Heterocyclic Cationic Gemini Surfactants: A Comparative Overview of Their Synthesis, Self-assembling, Physicochemical, and Biological Properties (original) (raw)
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Journal of Surfactants and Detergents, 2020
In this study, we prepared a novel series of diester-functionalized cationic gemini surfactants (C m-E2O2-C m) containing ethylene oxide as a spacer with varying alkyl chain lengths and characterized by 1 H NMR, FT-IR, elemental analysis, and ESI-MS. The physicochemical properties of the geminis were explored by tensiometry, fluorescence, dye solubilization, and Krafft point. These geminis acquire superior surface activity than the conventional surfactants. Fluorescence spectroscopy analysis affirmed that the micropolarity and aggregation number of micelles diminished with increase in the alkyl chain length. These geminis represent a new group of amphiphiles of considerably high biodegradability, better cleavability, and low toxicity as assessed by BOD test, FT-IR analysis, and HC 50 analysis, respectively. They also showed significant level of antimicrobial activity toward some specified bacterial strains of Gram-positive and Gram-negative by using agar well diffusion method. Furthermore, the thermogravimetric analysis provided information regarding thermal stabilities of the newly synthesized gemini surfactants. Keywords C m-E2O2-C m gemini surfactants Á Physicochemical properties Á Antimicrobial activities Á TGA
Overview of Synthetic Methodologies for Development of Cationic Gemini Surfactants
Journal of the Japan Society of Colour Material, 2017
Cationic surfactants are important category of surfactant molecules, which are important constituent of several commercial formulations. Gemini cationic surfactants consisting of two positively charged hydrophilic headgroup and two hydrophobic tail often connected by a spacer are considered superior surfactants molecules due to their affinity to self-aggregate at much lower concentration in aqueous solution compared to the monomeric counterparts 1,2). In recent years several new types of the cationic gemini surfactants have been developed and investigated for different application areas. These gemini surfactants have demonstrated ability to interact and condense DNA, form complexes with active drug molecules and enhanced ability to kill and retard the growth of pathogenic microorganisms, and hence are presently being investigated for several biomedical applications. These surfactants often self-aggregate for form micelles at very low concentration and demonstrate superior surfactant properties compared to conventional monomeric
Gemini Surfactant Based Carriers in Gene and Drug Delivery
Current Medicinal Chemistry, 2009
Lipid-based drug carriers, such as liposomes or drug/lipid complexes, have been extensively investigated in a large number of therapeutic protocols such as gene therapy, drug delivery, drug targeting and antibacterial treatments, in preclinical and clinical trials. Many formulations composed of natural and/or synthetic amphiphiles have been studied. Many synthetic lipids and surfactants have been designed and tested in order to improve liposomes and lipid complexes performances, such as fusion with cellular membrane, cellular uptake, target selectivity, transfection efficiency, low toxicity. Among these, gemini surfactants have been shown to be highly effective in delivering genetic material to cells, and also have been shown promising as synthetic additives in liposome formulations for drug delivery. The encouraging results obtained in gene therapy have given impulse to chemist creativity: an extensive selection of pH sensitive, sugar-, aminoacid-, and peptide-based gemini surfactants have been developed, many of which have shown good biological features. This review focuses on recent progress in gemini surfactant based formulations and their applications in different therapeutic protocols.
International Journal of Pharmaceutics, 2014
Gemini surfactants have been successfully used as components of gene delivery systems. In the present work, a family of gemini surfactants, represented by the general structure [C m H 2m+1 (CH 3 ) 2 N + (CH 2 ) s N + (CH 3 ) 2 C m H 2m+1 ]2Br À , or simply m-s-m, was used to prepare cationic gene carriers, aiming at their application in transfection studies. An extensive characterization of the gemini surfactant-based complexes, produced with and without the helper lipids cholesterol and DOPE, was carried out in order to correlate their physico-chemical properties with transfection efficiency. The most efficient complexes were those containing helper lipids, which, combining amphiphiles with propensity to form structures with different intrinsic curvatures, displayed a morphologically labile architecture, putatively implicated in the efficient DNA release upon complex interaction with membranes. While complexes lacking helper lipids were translocated directly across the lipid bilayer, complexes containing helper lipids were taken up by cells also by macropinocytosis. This study contributes to shed light on the relationship between important physico-chemical properties of surfactant-based DNA vectors and their efficiency to promote gene transfer, which may represent a step forward to the rational design of gene delivery systems.
Gemini surfactants: A distinct class of self-assembling molecules
2002
Gemini surfactant is the family of surfactant molecules possessing more than one hydrophobic tail and hydrophilic head group. These surfactants usually have better surface-active properties than corresponding conventional surfactants of equal chain length. Geminis are used as promising surfactants in industrial detergency and have shown efficiency in skin care, antibacterial property, metal-encapped porphyrazine and vesicle formation, construction of highporosity materials, etc. This review deals with synthesis, structure, critical micellar concentration, surface active properties and uses of geminis.
New serine-derived gemini surfactants as gene delivery systems
European Journal of Pharmaceutics and Biopharmaceutics, 2015
9 a b s t r a c t 30 Gemini surfactants have been extensively used for in vitro gene delivery. Amino acid-derived gemini sur-31 factants combine the special aggregation properties characteristic of the gemini surfactants with high 32 biocompatibility and biodegradability. In this work, novel serine-derived gemini surfactants, differing 33 in alkyl chain lengths and in the linker group bridging the spacer to the headgroups (amine, amide 34 and ester), were evaluated for their ability to mediate gene delivery either per se or in combination with 35 helper lipids. Gemini surfactant-based DNA complexes were characterized in terms of hydrodynamic dia-36 meter, surface charge, stability in aqueous buffer and ability to protect DNA. Efficient formulations, able 37 to transfect up to 50% of the cells without causing toxicity, were found at very low surfactant/DNA charge 38 ratios (1/1-2/1). The most efficient complexes presented sizes suitable for intravenous administration 39 and negative surface charge, a feature known to preclude potentially adverse interactions with serum 40 components. This work brings forward a new family of gemini surfactants with great potential as gene 41 delivery systems. 42 Ó 2014 Published by Elsevier B.V. 43 44 45 46
Multifunctional Gemini Surfactants: Structure, Synthesis, Properties and Applications
Application and Characterization of Surfactants, 2017
Gemini cationic surfactants are compounds which are composed of two hydrophilic head groups and two hydrophobic tails linked by a spacer at the head groups or closed to them. The spacer can be either hydrophobic or hydrophilic. It can be rigid or flexible. The neutral charge of the molecule is retained by the presence of organic or inorganic counterions. Critical micelle concentrations (CMCs), surface tension (γ) and minimal inhibitory concentration (MIC) are dozen times lower than corresponding parameters of monomeric surfactants. The unique properties of gemini surfactants with a wide range of hydrophiliclipophilic balance (HLB) make them a very useful, innovative material in detergents, cosmetics, personal care products, additives for paints and coatings, biocides, material science, organic synthesis, pharmacy, textiles, enhanced oil recovery, nanotechnology, petroleum and many other branches of life. A large number of papers concerning gemini surfactants have been published so far. This review presents a synthetic look at current work devoted to structure, synthesis and applications of gemini surfactants.
Central European Journal of Chemistry, 2007
A series of homologous gemini surfactants possessing identical hydrophobic chains but different ionic head groups (cationic, anionic, zwitterionic) were synthesized, and their aqueous solution properties were examined. The results showed that the surface activities of gemini surfactants are superior to those of corresponding conventional monomeric surfactants, and molecular arrangements of gemini surfactants at the air-water interface are tighter than those of corresponding conventional surfactants. It was also found that zwitterionic gemini surfactant possesses the highest surface activity among the three surfactants. The behavior at the air-water interface is closely related to the molecular structural features of surfactants, which provide an indication for synthesizing highly-efficient surfactants.