Sökning: onr:"swepub:oai:DiVA.org:liu-50118" > Fenton chemistry an...
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000 | 03824naa a2200337 4500 | |
001 | oai:DiVA.org:liu-50118 | |
003 | SwePub | |
008 | 091011s2006 | |||||||||||000 ||eng| | |
024 | 7 | a https://urn.kb.se/resolve?urn=urn:nbn:se:liu:diva-501182 URI |
024 | 7 | a https://doi.org/10.1021/tx060101w2 DOI |
040 | a (SwePub)liu | |
041 | a engb eng | |
042 | 9 SwePub | |
072 | 7 | a ref2 swepub-contenttype |
072 | 7 | a art2 swepub-publicationtype |
100 | 1 | a Merkofer, M.u Laboratorium für Anorganische Chemie, Departement Chemie und Angewandte Biowissenschaften, ETH Zürich, CH-8093 Zürich, Switzerland4 aut |
245 | 1 0 | a Fenton chemistry and iron chelation under physiologically relevant conditions :b Electrochemistry and kinetics |
264 | c 2006-09-27 | |
264 | 1 | b American Chemical Society (ACS),c 2006 |
338 | a print2 rdacarrier | |
520 | a The goal of iron-chelation therapy is to reduce the levels of labile plasma iron, and intravenously administered desferrioxamine is the gold standard of therapeutic agents. Hydroxypyridinones, e.g., CP20 (3-hydroxy-1,2- dimethylpyridin-4(1H)-one), are used or are under investigation as orally administered iron chelators. We determined electrode potentials of CP20, the related hydoxypyridones CP361, CP363, and CP502, and ICL670 (4-[3,5-bis(2- hydroxyphenyl)-1H-1,2,4-triazol-1-yl]benzoic acid) under physiologically relevant conditions to address the question of whether iron in the presence of these chelating agents can carry out Fenton chemistry in vivo. We found that iron(III) but not iron(II) binds tightly to both CP20 and ICL670 at pH 7 and higher, compared to nearly complete binding of 1 µM iron(II) to 10 µM desferrioxamine at pH 7.4 The electrode potentials of the hydroxypyridinones shift to more negative values with decreasing pKa values at lower concentrations of iron(III) (0.02 mM) and ligand (0.1 mM). The electrode potential of the iron-CP20 system decreases as a function of increasing pH, with a minimum near pH 10.5. We estimate an electrode potential for the ascorbyl radical/ascorbate couple under physiological conditions of +105 mV, which is higher than the electrode potential of the iron(III) complex of CP20 at all concentrations of iron. The rate of oxidation of iron(II) in the presence of CP20 by hydrogen peroxide increases with the concentrations of both ligand and peroxide. Although iron(II) is oxidized by hydrogen peroxide, the thus-formed FeIII(CP20)3 complex cannot be reduced by ascorbate. Therefore, the tight binding of iron(III) by this class of chelators prevents redox cycling. © 2006 American Chemical Society. | |
653 | a MEDICINE | |
653 | a MEDICIN | |
700 | 1 | a Kissner, R.u Laboratorium für Anorganische Chemie, Departement Chemie und Angewandte Biowissenschaften, ETH Zürich, CH-8093 Zürich, Switzerland4 aut |
700 | 1 | a Hider, R.C.u Department of Pharmacy, King's College London, Franklin-Wilkins Building, 150 Stamford Street, London SE1 9NN, United Kingdom4 aut |
700 | 1 | a Brunk, Ulfu Linköpings universitet,Hälsouniversitetet,Farmakologi4 aut0 (Swepub:liu)ulfbr20 |
700 | 1 | a Koppenol, W.H.u Laboratorium für Anorganische Chemie, Departement Chemie und Angewandte Biowissenschaften, ETH Zürich, CH-8093 Zürich, Switzerland4 aut |
710 | 2 | a Laboratorium für Anorganische Chemie, Departement Chemie und Angewandte Biowissenschaften, ETH Zürich, CH-8093 Zürich, Switzerlandb Department of Pharmacy, King's College London, Franklin-Wilkins Building, 150 Stamford Street, London SE1 9NN, United Kingdom4 org |
773 | 0 | t Chemical Research in Toxicologyd : American Chemical Society (ACS)g 19:10, s. 1263-1269q 19:10<1263-1269x 0893-228Xx 1520-5010 |
856 | 4 8 | u https://urn.kb.se/resolve?urn=urn:nbn:se:liu:diva-50118 |
856 | 4 8 | u https://doi.org/10.1021/tx060101w |
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