Antiradical Properties of N-Oxide Surfactants—Two in One

Abstract

Surfactants are molecules that lower surface or interfacial tension, and thus they are broadly used as detergents, wetting agents, emulsifiers, foaming agents, or dispersants. However, for modern applications, substances that can perform more than one function are desired. In this study we evaluated antioxidant properties of two homological series of N-oxide surfactants: monocephalic 3-(alkanoylamino)propyldimethylamine-N-oxides and dicephalic N,N-bis[3 ,3′-(dimethylamino)propyl]alkylamide di-N-oxides. Their antiradical properties were tested against stable radicals using electron paramagnetic resonance (EPR) and UV-vis spectroscopy. The experimental investigation was supported by theoretical density functional theory (DFT) and ab initio modeling of the X–H bonds dissociation enthalpies, ionization potentials, and Gibbs free energies for radical scavenging reactions. The evaluation was supplemented with a study of biological activity. We found that the mono- and di-N-oxides are capable of scavenging reactive radicals; however, the dicephalic surfactants are more efficient than their linear analogues.

Medicinal Chemistry of Drugs with N-Oxide Functionalities

“…Pyridine- N -oxide has been shown to have similar properties as the tyrosine/tyrosyl radical redox couple and can thus serve as an electron shuttle in artificial photosynthesis (Figure D). , Along the same lines, polymeric N -oxides have been found to have special electron transport properties useful for the construction of semiconducting polymers and interlayer materials for organic solar cells . This special radical reactivity might also be the reason for the antioxidant properties, which have been suggested for several amphiphilic N -oxides used in cosmetic applications. , …”

Design and Engineering of “Green” Nanoemulsions for Enhanced Topical Delivery of Bakuchiol Achieved in a Sustainable Manner: A Novel Eco-Friendly Approach to Bioretinol

“…The in vitro cytotoxicity evaluation of the studied nanoemulsions was performed using a 3-[4,5-dimethylthiazol-2-yl]-2,5 diphenyl tetrazolium bromide (MTT) cell viability assay as in our previous studies [ 12 , 34 ]. For the experiments, human skin cells were removed by trypsinization (trypsin 0.025% and EDTA 0.002% solution) and rinsed twice with PBS.…”

Understanding the Exchange Interaction between Paramagnetic Metal Ions and Radical Ligands: DFT and Ab Initio Study on Semiquinonato Cu(II) Complexes

“…It is now well established that theoretical methods are an efficient multipurpose tool for chemistry, biochemistry, and material science. Recent scientific efforts have shown that they can help us understand various phenomena, for example, reaction mechanisms or reactivity [ 35 , 36 , 37 , 38 ], electron density distribution [ 39 , 40 , 41 ], and elusive structure of complex biochemical systems or radical centers [ 42 , 43 , 44 ], anticancer [ 35 , 45 ] and antioxidant properties [ 46 , 47 , 48 , 49 , 50 , 51 ], soot formation [ 52 ] or pesticide decomposition [ 53 ]. The exchange coupling between paramagnetic centers has been a subject of such investigations at the density functional theory (DFT) and ab initio levels, but these studies were mainly limited to the interaction between metallic centers [ 54 , 55 , 56 , 57 , 58 , 59 , 60 , 61 , 62 , 63 , 64 , 65 , 66 , 67 , 68 , 69 , 70 , 71 , 72 , 73 , 74 , 75 , 76 ].…”