Biomaterial Database

Protection of linoleic acid hydroperoxide-induced cytotoxicity by phenolic antioxidants. 1994

T Kaneko, and K Kaji, and M Matsuo

Tokyo Metropolitan Institute of Gerontology, Itabashiku, Japan.

The protective effects of phenolic antioxidants on linoleic acid hydroperoxide (LOOH)-induced toxicity to cultured human umbilical vein endothelial cells were examined. Our previous results were confirmed that for tocopherol homologs, lipophilicity and the presence of a phenolic hydroxyl group and two alkyl groups at its ortho positions are critical for protection against LOOH-induced cytotoxicity. Probucol and butylated hydroxytoluene (BHT) were more effective than other simple alkylated phenols. It was found that the protective effects of alkylated phenols were depended on by the presence of two alkyl groups; in particular, two tert-butyl groups, at positions ortho to a hydroxyl group and an alkyl group at the para position. Among alpha-tocopherol, 2,2,5,7,8-pentamethylchroman-6-ol, and BHT, the relative effectiveness of protection against the cytotoxicity (1.0:0.86:0.58, respectively) was inconsistent with the previously reported, relative antioxidant activity in homogeneous solution (1.0:1.2:0.004, respectively). Probably, the effectiveness of protection by phenolic antioxidants against the cytotoxicity depend primarily on their incorporation rate into cells due to their lipophilicity, secondly on their antioxidant activity, and thirdly on their orientation in biomembranes.

UI	MeSH Term	Description	Entries
D008041	Linoleic Acids	Eighteen-carbon essential fatty acids that contain two double bonds.	Acids, Linoleic
D008054	Lipid Peroxides	Peroxides produced in the presence of a free radical by the oxidation of unsaturated fatty acids in the cell in the presence of molecular oxygen. The formation of lipid peroxides results in the destruction of the original lipid leading to the loss of integrity of the membranes. They therefore cause a variety of toxic effects in vivo and their formation is considered a pathological process in biological systems. Their formation can be inhibited by antioxidants, such as vitamin E, structural separation or low oxygen tension.	Fatty Acid Hydroperoxide,Lipid Peroxide,Lipoperoxide,Fatty Acid Hydroperoxides,Lipid Hydroperoxide,Lipoperoxides,Acid Hydroperoxide, Fatty,Acid Hydroperoxides, Fatty,Hydroperoxide, Fatty Acid,Hydroperoxide, Lipid,Hydroperoxides, Fatty Acid,Peroxide, Lipid,Peroxides, Lipid
D010636	Phenols	Benzene derivatives that include one or more hydroxyl groups attached to the ring structure.
D011341	Probucol	A drug used to lower LDL and HDL cholesterol yet has little effect on serum-triglyceride or VLDL cholesterol. (From Martindale, The Extra Pharmacopoeia, 30th ed, p993).	Biphenabid,DH-581,Lorelco,Lurselle,Panavir,Superlipid,DH 581,DH581
D002084	Butylated Hydroxytoluene	A di-tert-butyl PHENOL with antioxidant properties.	Butylhydroxytoluene,2,6-Bis(1,1-dimethylethyl)-4-methylphenol,2,6-Di-t-butyl-4-methylphenol,2,6-Di-tert-butyl-4-methylphenol,2,6-Di-tert-butyl-p-cresol,4-Methyl-2,6-ditertbutylphenol,BHT,Di-tert-butyl-methylphenol,Dibunol,Ionol,Ionol (BHT),2,6 Di t butyl 4 methylphenol,2,6 Di tert butyl 4 methylphenol,2,6 Di tert butyl p cresol,4 Methyl 2,6 ditertbutylphenol,Di tert butyl methylphenol,Hydroxytoluene, Butylated
D002470	Cell Survival	The span of viability of a cell characterized by the capacity to perform certain functions such as metabolism, growth, reproduction, some form of responsiveness, and adaptability.	Cell Viability,Cell Viabilities,Survival, Cell,Viabilities, Cell,Viability, Cell
D002478	Cells, Cultured	Cells propagated in vitro in special media conducive to their growth. Cultured cells are used to study developmental, morphologic, metabolic, physiologic, and genetic processes, among others.	Cultured Cells,Cell, Cultured,Cultured Cell
D002839	Chromans	Benzopyrans saturated in the 2 and 3 positions.	Dihydrobenzopyrans
D004730	Endothelium, Vascular	Single pavement layer of cells which line the luminal surface of the entire vascular system and regulate the transport of macromolecules and blood components.	Capillary Endothelium,Vascular Endothelium,Capillary Endotheliums,Endothelium, Capillary,Endotheliums, Capillary,Endotheliums, Vascular,Vascular Endotheliums
D005609	Free Radicals	Highly reactive molecules with an unsatisfied electron valence pair. Free radicals are produced in both normal and pathological processes. Free radicals include reactive oxygen and nitrogen species (RONS). They are proven or suspected agents of tissue damage in a wide variety of circumstances including radiation, damage from environment chemicals, and aging. Natural and pharmacological prevention of free radical damage is being actively investigated.	Free Radical