Quercetin–iron chelates are transported via glucose transporters

Free Radical Biology and Medicine - Tập 50 - Trang 934-944 - 2011
Evangelia Vlachodimitropoulou1, Paul A. Sharp2, Richard J. Naftalin1
1Physiology, Waterloo Campus, King's College London, London SE1 9HN, UK
2Nutritional Sciences, Waterloo Campus, King's College London, London SE1 9HN, UK

Tài liệu tham khảo

McCord, 1996, Effects of positive iron status at a cellular level, Nutr. Rev., 54, 85, 10.1111/j.1753-4887.1996.tb03876.x Kakhlon, 2002, The labile iron pool: characterization, measurement, and participation in cellular processes, Free Radic. Biol. Med., 33, 1037, 10.1016/S0891-5849(02)01006-7 Petrat, 2001, Subcellular distribution of chelatable iron: a laser scanning microscopic study in isolated hepatocytes and liver endothelial cells, Biochem. J., 356, 61, 10.1042/0264-6021:3560061 Goodwin, 1965, Chelation of ferrous sulphate solutions by desferrioxamine B, Nature, 205, 281, 10.1038/205281b0 Bischoff, 2008, Quercetin: potentials in the prevention and therapy of disease, Curr. Opin. Clin. Nutr. Metab. Care, 11, 733, 10.1097/MCO.0b013e32831394b8 Fiorani, 2003, Human red blood cells as a natural flavonoid reservoir, Free Radic. Res., 37, 1331, 10.1080/10715760310001615998 Cunningham, 2006, Docking studies show that D-glucose and quercetin slide through the transporter GLUT1, J. Biol. Chem., 281, 5797, 10.1074/jbc.M509422200 Strobel, 2005, Myricetin, quercetin and catechin-gallate inhibit glucose uptake in isolated rat adipocytes, Biochem. J., 386, 471, 10.1042/BJ20040703 Pascoe, 1996, Differential targeting of facilitative glucose transporters in polarized epithelial cells, Am. J. Physiol. Cell Physiol., 271, C547, 10.1152/ajpcell.1996.271.2.C547 Hertog, 1993, Intake of potentially anticarcinogenic flavonoids and their determinants in adults in The Netherlands, Nutr. Cancer, 20, 21, 10.1080/01635589309514267 Janbaz, 2002, Protective effect of rutin on paracetamol- and CCl4-induced hepatotoxicity in rodents, Fitoterapia, 73, 557, 10.1016/S0367-326X(02)00217-4 Huang, 2006, Transport kinetics of iron chelators and their chelates in Caco-2 cells, Pharm. Res., 23, 280, 10.1007/s11095-005-9258-5 Wyman, 2008, Dcytb (Cybrd1) functions as both a ferric and a cupric reductase in vitro, FEBS Lett., 582, 1901, 10.1016/j.febslet.2008.05.010 Imada, 1999, Analysis of reactive oxygen species generated by neutrophils using a chemiluminescence probe L-012, Anal. Biochem., 271, 53, 10.1006/abio.1999.4107 Shingles, 2001, Direct measurement of ferrous ion transport across membranes using a sensitive fluorometric assay, Anal. Biochem., 296, 106, 10.1006/abio.2001.5209 McKie, 2001, An iron-regulated ferric reductase associated with the absorption of dietary iron, Science, 291, 1755, 10.1126/science.1057206 Guo, 2007, Iron-binding properties of plant phenolics and cranberry's bio-effects, Dalton Trans., 4951, 10.1039/b705136k Fernandez, 2002, Iron and copper chelation by flavonoids: an electrospray mass spectrometry study, J. Inorg. Biochem., 92, 105, 10.1016/S0162-0134(02)00511-1 Vanderzee, 1993, Hydroxyl radical generation by a light-dependent Fenton reaction, Free Radic. Biol. Med., 14, 105, 10.1016/0891-5849(93)90001-B Papadopoulou, 2005, Interaction of flavonoids with bovine serum albumin: a fluorescence quenching study, J. Agric. Food Chem., 53, 158, 10.1021/jf048693g Loban, 1997, Iron-binding antioxidant potential of plasma albumin, Clin. Sci. (London), 93, 445, 10.1042/cs0930445 Bolli, 2010, Flavonoid binding to human serum albumin, Biochem. Biophys. Res. Commun., 398, 444, 10.1016/j.bbrc.2010.06.096 Park, 2000, Intracellular accumulation of ascorbic acid is inhibited by flavonoids via blocking of dehydroascorbic acid and ascorbic acid uptakes in HL-60, U937 and Jurkat cells, J. Nutr., 130, 1297, 10.1093/jn/130.5.1297 Dufour, 2005, Flavonoid–serum albumin complexation: determination of binding constants and binding sites by fluorescence spectroscopy, Biochim. Biophys. Acta, 1721, 164, 10.1016/j.bbagen.2004.10.013 LeFevre, 1961, Sugar transport in the red blood cell: structure–activity relationships in substrates and antagonists, Pharmacol. Rev., 13, 39 Basketter, 1978, Asymmetry of the hexose transfer system in human erythrocytes: comparison of the effects of cytochalasin B, phloretin and maltose as competitive inhibitors, J. Physiol., 278, 389, 10.1113/jphysiol.1978.sp012311 Salas-Burgos, 2004, Predicting the three-dimensional structure of the human facilitative glucose transporter glut1 by a novel evolutionary homology strategy: insights on the molecular mechanism of substrate migration, and binding sites for glucose and inhibitory molecules, Biophys. J., 87, 2990, 10.1529/biophysj.104.047886 Cloherty, 2001, The red blood cell glucose transporter presents multiple, nucleotide-sensitive sugar exit sites, Biochemistry, 40, 15549, 10.1021/bi015586w Comporti, 2002, Iron release, oxidative stress and erythrocyte ageing, Free Radic. Biol. Med., 32, 568, 10.1016/S0891-5849(02)00759-1 Hershko, 2005, Objectives and mechanism of iron chelation therapy, Ann. NY Acad. Sci., 1054, 124, 10.1196/annals.1345.015 Petrat, 1999, Determination of the chelatable iron pool of isolated rat hepatocytes by digital fluorescence microscopy using the fluorescent probe, Phen Green SK, Hepatology, 29, 1171, 10.1002/hep.510290435 Browne, 1997, Removal of erythrocyte membrane iron in vivo ameliorates the pathobiology of murine thalassemia, J. Clin. Invest., 100, 1459, 10.1172/JCI119666 Porter, 2009, Optimizing iron chelation strategies in beta-thalassaemia major, Blood Rev., 23, S3, 10.1016/S0268-960X(09)70003-7 Giardina, 2001, Chelation therapy in beta-thalassemia: an optimistic update, Semin. Hematol., 38, 360, 10.1016/S0037-1963(01)90030-7 Vlachodimitropoulou, 2010, Quercetin is a substrate for the transmembrane oxidoreductase Dcytb, Free Radic. Biol. Med., 48, 1366, 10.1016/j.freeradbiomed.2010.02.021 Savini, 2008, SVCT1 and SVCT2: key proteins for vitamin C uptake, Amino Acids, 34, 347, 10.1007/s00726-007-0555-7 Naftalin, 2003, Interactions of androgens, green tea catechins and the antiandrogen flutamide with the external glucose-binding site of the human erythrocyte glucose transporter GLUT1, Br. J. Pharmacol., 140, 487, 10.1038/sj.bjp.0705460 Naftalin, 2004, Piracetam and TRH analogues antagonise inhibition by barbiturates, diazepam, melatonin and galanin of human erythrocyte D-glucose transport, Br. J. Pharmacol., 142, 594, 10.1038/sj.bjp.0705798 Dwyer, 2009, The effects of midazolam on the acquisition and expression of fructose- and maltodextrin-based flavour preferences, Pharmacol. Biochem. Behav., 91, 503, 10.1016/j.pbb.2008.09.001 Kottra, 2007, Flavonoid glycosides are not transported by the human Na+/glucose transporter when expressed in Xenopus laevis oocytes, but effectively inhibit electrogenic glucose uptake, J. Pharmacol. Exp. Ther., 322, 829, 10.1124/jpet.107.124040 Wang, 2007, Flavonoids modulate monocarboxylate transporter-1-mediated transport of gamma-hydroxybutyrate in vitro and in vivo, Drug Metab. Dispos., 35, 201, 10.1124/dmd.106.012369 Wu, 2005, Interactions of mefloquine with ABC proteins, MRP1 (ABCC1) and MRP4 (ABCC4) that are present in human red cell membranes, Biochem. Pharmacol., 70, 500, 10.1016/j.bcp.2005.05.022 Sen, 1962, Variations of the parameters of glucose transfer across the human erythrocyte membrane in the presence of inhibitors of transfer, J. Physiol., 160, 404, 10.1113/jphysiol.1962.sp006855 Ader, 2001, Interaction of quercetin glucosides with the intestinal sodium/glucose co-transporter (SGLT-1), Cancer Lett., 162, 175, 10.1016/S0304-3835(00)00645-5 Grady, 1998, Iron chelation: combined therapy could be a better approach, Blood, 92, 3046 Hider, 2003, Emerging understanding of the advantage of small molecules such as hydroxypyridinones in the treatment of iron overload, Curr. Med. Chem., 10, 1051, 10.2174/0929867033457629 Hershko, 2005, Objectives and mechanism of iron chelation therapy, Cooley's Anemia Eighth Symp., 1054, 124 Ferrali, 1997, Protection against oxidative damage of erythrocyte membrane by the flavonoid quercetin and its relation to iron chelating activity, FEBS Lett., 416, 123, 10.1016/S0014-5793(97)01182-4 Barber, 1962, Enzymic glycosylation of quercetin to rutin, Biochemistry, 1, 463, 10.1021/bi00909a015 Williams, 2004, Flavonoids: antioxidants or signalling molecules?, Free Radic. Biol. Med., 36, 838, 10.1016/j.freeradbiomed.2004.01.001 Lee, 2010, Mitochondrial GLUT10 facilitates dehydroascorbic acid import and protects cells against oxidative stress: mechanistic insight into arterial tortuosity syndrome, Hum. Mol. Genet., 19, 3721, 10.1093/hmg/ddq286 Erlund, 2006, Bioavailability of quercetin from berries and the diet, Nutr. Cancer, 54, 13, 10.1207/s15327914nc5401_3 Shanzer, 1991, Reversed siderophores act as antimalarial agents, Proc. Natl Acad. Sci. USA, 88, 6585, 10.1073/pnas.88.15.6585 Afzal-Ahmed, 2007, Preeclampsia inactivates glucose-6-phosphate dehydrogenase and impairs the redox status of erythrocytes and fetal endothelial cells, Free Radic. Biol. Med., 42, 1781, 10.1016/j.freeradbiomed.2007.02.032