Micellization of Lactosylammonium Surfactants with Different Counter Ions and Their Interaction with DNA

Abstract

So far, the studies about the physical chemical properties of sugar-based surfactants have been still unsystematic; most of the studies have been focused on nonionic sugar-based surfactants. In the present work, we studied the micellization of four lactose-based surfactants, with the same headgroup (lactosylammonium) and the same hydrophobic alkyl chain (dodecyl) but different counterions (malonate, adipate, propionate, and hexanoate), at 25.0 and/or 50.0 °C. We found that these four surfactants could decrease the surface tension of water to ca. 30 mN/m. When the number of carboxylate groups in the counterion was the same, the counterion having a shorter alkyl chain could lead to a smaller minimum area per surfactant molecule. Moreover, the surfactants with monocarboxylates as counterions had much lower critical micelle concentrations than those with dicarboxylates as counterions, and the micelles from the former surfactants had a lower counterion binding degree. The lactosylammonium surfactants could bind with DNA, and low content of the surfactant could decrease the CD signal of DNA, while high content of the surfactant could make DNA unfold somewhat.

Synthesis and characterization of cationic surfactants and their interactions with drug and metal complexes

“…By approaching the post-micellar concentration, the rise in absorption of drug molecules was witnessed showing the increased bioavailability of drug molecules. By increasing surfactant concentration, absorption of drug increases [21] and this surfactant-drug interaction follows a straight line pattern as shown in Fig. 4.…”

Self-Assembly of Amphiphilic Compounds as a Versatile Tool for Construction of Nanoscale Drug Carriers

“…The presence of a lactose moiety in the molecule provides both industrial and biotechnological significance to these compositions. These compounds could be used as efficient micellar catalysts of Ullmann C-S coupling reactions in water (the yield of product could reach 90% by selecting an appropriate alkyl tail length) [ 59 ]; highly-effective antibacterial agents against a wide spectrum of microorganisms [ 60 ]; coatings interrupting undesired adsorption processes [ 61 ]; compounds for condensation with DNA, that could be accurately tuned by selection of the counterion [ 62 ]; a basis of a vehicle for ketoprofen delivery [ 63 ]. Maltose and sucrose amphiphilic derivatives were recommended as components of microemulsions—potential alternative fuel [ 64 ], regulators of wettability of various solid surfaces like quartz and polyethylene [ 65 ] and modifiers of adsorption parameters at the air/liquid interface of systems [ 66 ].…”

Cationic Single-Chained Surfactants with a Functional Group at the End of the Hydrophobic Tail DNA Compacting Efficiency

“…An increment in the positive charge of the surfactant head group, or in the number of the positively charged head groups, tends, a priori, to increase the surfactant DNA compacting efficiency due to an increment in the electrostatic attractions between the negatively charged DNA and the surfactant [ 25 , 26 ]. The influence of the counter ion nature, the effect of substituting H atoms by F atoms in the hydrophobic chains, and the impact of the magnetic properties of the surfactants on the surfactant/DNA interactions, have also been investigated [ 27 , 28 , 29 ].…”

“…An increase in hydrophobic chain length and the presence of additional side hydrophobic tails, results in an improved compacting efficiency [ 16 , 30 , 31 ]. More favorable hydrophobic interactions also explain that, for a given tail length, dimeric surfactants are more efficient DNA-condensing agents than single-chained surfactants [ 1 , 4 , 5 , 25 , 26 , 27 , 28 , 32 , 33 , 34 , 35 , 36 ]. Spacer length, which is a structural characteristic specific for oligomeric surfactants, also influences the surfactant/DNA interactions [ 37 , 38 , 39 , 40 , 41 ].…”