The reactivity of carotenoid radicals with oxygen

References

• El-Agamey A, McGarvey DJ. First direct observation of reversible oxygen addition to a carotenoid-derived carbon-centered neutral radical. Org Lett 2005; 7: 3957–3960
   PubMed Web of Science ®Google Scholar
• El-Agamey A, McGarvey DJ. Evidence for a lack of reactivity of carotenoid addition radicals towards oxygen: A laser flash photolysis study of the reactions of carotenoids with acylperoxyl radicals in polar and non-polar solvents. J Am Chem Soc 2003; 125: 3330–3340
   PubMedGoogle Scholar
• Gao Y, Webb S, Kispert LD. Deprotonation of carotenoid radical cation and formation of a didehydrodimer. J Phys Chem B 2003; 107: 13237–13240
   Web of Science ®Google Scholar
• Woodall AA, Lee SWM, Weesie RJ, Jackson MJ, Britton G. Oxidation of carotenoids by free radicals: Relationship between structure and reactivity. Biochim Biophys Acta 1997; 1336: 33–42
   PubMed Web of Science ®Google Scholar
• D'Aquino M, Dunster C, Willson RL. Vitamin A and glutathione-mediated free radical damage: Competing reactions with polyunsaturated fatty acids and vitamin C. Biochem Biophys Res Commun 1989; 161: 1199–1203
   PubMed Web of Science ®Google Scholar
• Everett SA, Dennis MF, Patel KB, Maddix S, Kundu SC, Willson RL. Scavenging of nitrogen dioxide, thiyl, and sulfonyl free radicals by the nutritional antioxidant β-carotene. J Biol Chem 1996; 271: 3988–3994
   PubMed Web of Science ®Google Scholar
• Mortensen A, Skibsted LH, Sampson J, Rice-Evans C, Everett SA. Comparative mechanisms and rates of free radical scavenging by carotenoid antioxidants. FEBS Lett 1997; 418: 91–97
   PubMed Web of Science ®Google Scholar
• El-Agamey A, McGarvey DJ. Carotenoid addition radicals do not react with molecular oxygen: Aspects of carotenoid reactions with acylperoxyl radicals in polar and non-polar media. Free Radic Res 2002; 36(Suppl. S)97–100
   Google Scholar
• Frenette M, Aliaga C, Font-Sanchis E, Scaiano JC. Bond dissociation energies for radical dimers derived from highly stabilized carbon-centered radicals. Org Lett 2004; 6: 2579–2582
   PubMedGoogle Scholar
• Font-Sanchis E, Aliaga C, Cornejo R, Scaiano JC. Reactivity toward oxygen of isobenzofuranyl radicals: Effect of nitro group substitution. Org Lett 2003; 5: 1515–1518
   PubMedGoogle Scholar
• Font-Sanchis E, Aliaga C, Focsaneanu KS, Scaiano JC. Greatly attenuated reactivity of nitrile-derived carbon-centered radicals toward oxygen. Chem Commun 2002; 1576–1577
   PubMedGoogle Scholar
• Bejan EV, Font-Sanchis E, Scaiano JC. Lactone-derived carbon-centered radicals: Formation and reactivity with oxygen. Org Lett 2001; 3: 4059–4062
   PubMedGoogle Scholar
• Scaiano JC, Martin A, Yap GPA, Ingold KU. A carbon-centered radical unreactive toward oxygen: Unusual radical stabilization by a lactone ring. Org Lett 2000; 2: 899–901
   PubMedGoogle Scholar
• Burton GW, Ingold KU. β-Carotene: An unusual type of lipid antioxidant. Science 1984; 224: 569–573
   PubMed Web of Science ®Google Scholar
• Tinkler JH, Tavender SM, Parker AW, McGarvey DJ, Mulroy L, Truscott TG. Investigation of carotenoid radical cations and triplet states by laser flash photolysis and time-resolved resonance Raman spectroscopy: Observation of competitive energy and electron transfer. J Am Chem Soc 1996; 118: 1756–1761
   Google Scholar
• Ito O. Reactions of aromatic thiyl radicals. S-Centered radicals, ZB Alfassi. John Wiley & Sons, Chichester 1999; 193–224
   Google Scholar
• Britton G. UV/visible spectroscopy. Carotenoids. Volume 1B: Spectroscopy, G Britton, S Liaaen-Jensen, H Pfander. Birkhäuser Verlag, Basel 1995; 13–62
   Google Scholar
• Neta P, Huie RE, Ross AB. Rate constants for reactions of peroxyl radicals in fluid solutions. J Phys Chem Ref Data 1990; 19: 413–513
   Web of Science ®Google Scholar
• Pratt DA, Mills JH, Porter NA. Theoretical calculations of carbon-oxygen bond dissociation enthalpies of peroxyl radicals formed in the autoxidation of lipids. J Am Chem Soc 2003; 125: 5801–5810
   PubMed Web of Science ®Google Scholar
• Tallman KA, Pratt DA, Porter NA. Kinetic products of linoeate peroxidation: Rapid β-fragmentation of nonconjugated peroxyls. J Am Chem Soc 2001; 123: 11827–11828
   PubMedGoogle Scholar
• Porter NA, Caldwell SE, Mills KA. Mechanisms of free-radical oxidation of unsaturated lipids. Lipids 1995; 30: 277–290
   PubMed Web of Science ®Google Scholar
• Porter NA, Mills KA, Carter RL. A mechanistic study of oleate autoxidation: Competing peroxyl H-atom abstraction and rearrangement. J Am Chem Soc 1994; 116: 6690–6696
   Web of Science ®Google Scholar
• Krinsky NI, Yeum K-J. Carotenoid-radical interactions. Biochem Biophys Res Commun 2003; 305: 754–760
   PubMed Web of Science ®Google Scholar
• El-Agamey A, Lowe GM, McGarvey DJ, Mortensen A, Phillip DM, Truscott TG, Young AJ. Carotenoid radical chemistry and antioxidant/pro-oxidant properties. Arch Biochem Biophys 2004; 430: 37–48
   PubMed Web of Science ®Google Scholar
• Edge R, McGarvey DJ, Truscott TG. The carotenoids as anti-oxidants–a review. J Photochem Photobiol B: Biol 1997; 41: 189–200
   PubMed Web of Science ®Google Scholar
• Martin HD, Jäger C, Ruck C, Schmidt M, Walsh R, Paust J. Anti- and prooxidant properties of carotenoids. J Prakt Chem 1999; 341: 302–308
   Google Scholar
• Rice-Evans CA, Sampson J, Bramley PM, Holloway DE. Why do we expect carotenoids to be antioxidants in vivo?. Free Radic Res 1997; 26: 381–398
   PubMed Web of Science ®Google Scholar
• Kennedy TA, Liebler DC. Peroxyl radical scavenging by β-carotene in lipid bilayers. J Biol Chem 1992; 267: 4658–4663
   PubMed Web of Science ®Google Scholar
• Palozza P. Prooxidant actions of carotenoids in biologic systems. Nutr Rev 1998; 56: 257–265
   PubMed Web of Science ®Google Scholar
• Palozza P, Luberto C, Calviello G, Ricci P, Bartoli GM. Antioxidant and prooxidant role of β-carotene in murine normal and tumor thymocytes: Effects of oxygen partial pressure. Free Radic Biol Med 1997; 22: 1065–1073
   PubMed Web of Science ®Google Scholar
• Tsuchihashi H, Kigoshi M, Iwatsuki M, Niki E. Action of β-carotene as an antioxidant against lipid peroxidation. Arch Biochem Biophys 1995; 323: 137–147
   PubMed Web of Science ®Google Scholar
• Tesoriere L, D'Arpa D, Re R, Livrea MA. Antioxidant reactions of all-trans retinol in phospholipid bilayers: Effect of oxygen partial pressure, radical fluxes, and retinol concentration. Arch Biochem Biophys 1997; 343: 13–18
   PubMedGoogle Scholar
• Vile GF, Winterbourn CC. Inhibition of adriamycin-promoted microsomal lipid peroxidation by β-carotene, α-tocopherol and retinol at high and low oxygen partial pressures. FEBS Lett 1988; 238: 353–356
   PubMed Web of Science ®Google Scholar
• Young AJ, Lowe GM. Antioxidant and prooxidant properties of carotenoids. Arch Biochem Biophys 2001; 385: 20–27
   PubMed Web of Science ®Google Scholar