title: Tetradecylthioacetic acid and tetradecylselenoacetic acid inhibit lipid peroxidation and interact with superoxide radical.
abstract: Reactive oxygen species are thought to induce cellular damage and to play a pathological role in several human diseases. Tetradecylthioacetic acid (TTA) was previously reported to prevent the oxidative modification of low-density lipoprotein (LDL) particles and to act as an antioxidant. In this study we present a new fatty acid analogue, namely tetradecylselenoacetic acid (TSA), in which the sulfur atom of TTA is replaced by a selenium atom. TSA was more potent than TTA in increasing the lag time before the onset of LDL oxidation and this effect was dose dependent. TTA and TSA were shown to reduce the iron-ascorbate-induced microsomal lipid peroxidation, TSA being more efficient than TTA. TTA and TSA, in the presence of iron, interacted with the superoxide radical as assessed by direct and indirect testing methods. TSA like TTA failed to scavenge 1.1-diphenyl-2-picrylhydrazyl radicals. TSA bound copper ions as shown by the wavelength spectra measurement. These results suggest that TTA and TSA exert their antioxidant capacity by interaction with copper or iron ions in radical scavenging, TSA being more potent than TTA. Nevertheless, a chelating effect resulting in chemically inactive metal ions cannot be excluded.
authors.affiliation: Institute of Clinical Biochemistry, University of Bergen, Haukeland University Hospital, Bergen, Norway.
authors.forename: Z A
authors.initials: ZA
authors.lastname: Muna
authors.forename: B J
authors.initials: BJ
authors.lastname: Bolann
authors.forename: X
authors.initials: X
authors.lastname: Chen
authors.forename: J
authors.initials: J
authors.lastname: Songstad
authors.forename: R K
authors.initials: RK
authors.lastname: Berge
mesh_terms: D000818:Animals; D000975:Antioxidants / Q000378:metabolism / Q000633:toxicity; D001205:Ascorbic Acid / Q000037:antagonists & inhibitors / Q000378:metabolism; D015764:Bepridil / Q000031:analogs & derivatives* / Q000378:metabolism; D001713:Biphenyl Compounds; D003300:Copper / Q000378:metabolism; D003574:Cytochrome c Group / Q000378:metabolism; D004587:Electrophoresis, Agar Gel; D005227:Fatty Acids / Q000378:metabolism / Q000633:toxicity; D005296:Ferrous Compounds / Q000037:antagonists & inhibitors / Q000378:metabolism; D016166:Free Radical Scavengers / Q000378:metabolism* / Q000633:toxicity*; D007501:Iron / Q000378:metabolism; D015227:Lipid Peroxidation / Q000187:drug effects*; D008077:Lipoproteins, LDL / Q000378:metabolism; D008297:Male; D008862:Microsomes, Liver / Q000187:drug effects / Q000378:metabolism; D009942:Organometallic Compounds / Q000378:metabolism* / Q000633:toxicity*; D019308:Palmitic Acid / Q000378:metabolism; D010851:Picrates; D051381:Rats; D017208:Rats, Wistar; D013440:Sulfides / Q000378:metabolism* / Q000633:toxicity*; D013481:Superoxides / Q000378:metabolism*
chemical_list: D000975:Antioxidants; D001713:Biphenyl Compounds; D003574:Cytochrome c Group; D005227:Fatty Acids; D005296:Ferrous Compounds; D016166:Free Radical Scavengers; D008077:Lipoproteins, LDL; D009942:Organometallic Compounds; D010851:Picrates; D013440:Sulfides; C410666:tetradecylselenoacetic acid; D013481:Superoxides; D019308:Palmitic Acid; D015764:Bepridil; D003300:Copper; C062078:1-(carboxymethylthio)tetradecane; C004931:1,1-diphenyl-2-picrylhydrazyl; D007501:Iron; D001205:Ascorbic Acid