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• W2057406912 abstract "A polyunsaturated analogue of alpha-tocopherol was synthesized that is both fluorescent and sensitive to peroxidative chemistry that occurs in phospholipid membranes. alpha-Tocohexaenol 1, [(S)-2,5,7,8-tetramethyl-2-((1E/Z,3E,5E,7E,9E)-4,8,12-trimethyltrideca-1,3,5,7,9,11-hexaenyl)chroman-6-ol, alpha-T6] was prepared by condensing a known triene fragment triphenyl-(2,6-dimethyl-octa-2,4,6-trienoic acid methyl ester)-phosphonium bromide with a protected chromanol aldehyde, (2S)-6-{[tert-butyl(dimethyl)silyl]oxy}-2,5,7,8-tetra-methyl-3,4-dihydro-2H-chromene-2-carbaldehyde. The full side chain was then completed with isopentyl(tri-n-butyl)phosphonium bromide to give 1. The geometry of the C1'-C2' alkene appears to be Z (cis) although the coupling constants of the olefinic protons are intermediate between values normally assigned to E and Z-isomers. In ethanol, alpha-T6 has a maximum absorption at 368nm with an absorption coefficient of 45,000M(-1) cm(-1), and displays a maximum fluorescence emission at 523nm. The susceptibility of alpha-T6 to peroxidative chemistry was dependent on the concentration of azo-initiators of lipid oxidation in acetonitrile solution as well as in phospholipid vesicles. A loss of fluorescence at 520nm was observed when alpha-T6 (vesicles or alpha-T6-lipid mixtures) was exposed to peroxidative conditions, and this loss mirrored the production of conjugated dienes and trienes during the peroxidation of bulk phospholipids. Addition of natural alpha-tocopherol during the AMVN induced oxidation of 4microM alpha-T6 and 0.5mg/ml soybean PC induced a characteristic lag phase, after which the fluorescence of alpha-T6 began to lessen. Thus, alpha-T6 may be a useful reporter not only of tocopherol location in cells, but also of the extent of peroxidative events." @default.
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• W2057406912 date "2010-01-01" @default.
• W2057406912 modified "2023-09-23" @default.
• W2057406912 title "Synthesis of α-tocohexaenol (α-T6) a fluorescent, oxidatively sensitive polyene analogue of α-tocopherol" @default.
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• W2057406912 doi "https://doi.org/10.1016/j.bmc.2009.11.051" @default.
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