title: Structure-dependent complexation of Fe3+ by anthracyclines. 2. The roles of methoxy and daunosamine functionalities.
abstract: We have investigated the effects of the methoxy and daunosamine sugar moieties on the stability of anthracycline complexes with Fe(3+) in aqueous solution. Idarubicin and daunorubicin are structurally very similar, differing only by the presence of the methoxy substituent at the 4-position. We demonstrate that the methoxy group interacts sterically with the proximal quinone oxygen atom and this interaction affects the stability of the anthracycline-iron(III) complex. A similar steric effect is seen for the pendent daunosamine moiety. Free daunosamine in solution does not show any significant interactions with iron(III), whereas the pendent daunosamine functionality destabilizes anthracycline-iron(III) complex formation. This body of information illustrates the important role of methoxy and daunosamine moieties in anthracycline-iron(III) complex formation and stability.
authors.affiliation: Department of Chemistry, University of Warsaw, Pasteura 1, Warsaw 02-093, Poland.
authors.forename: Krzysztof
authors.initials: K
authors.lastname: Nawara
authors.forename: Hillary
authors.initials: H
authors.lastname: Beeckman
authors.forename: Paweł
authors.initials: P
authors.lastname: Krysiński
authors.forename: G J
authors.initials: GJ
authors.lastname: Blanchard
mesh_terms: D018943:Anthracyclines / Q000737:chemistry*; D056831:Coordination Complexes / Q000737:chemistry; D005290:Ferric Compounds / Q000737:chemistry*; D006595:Hexosamines / Q000737:chemistry*; D015255:Idarubicin / Q000737:chemistry; D007477:Ions / Q000737:chemistry; D007700:Kinetics; D056004:Molecular Dynamics Simulation; D013816:Thermodynamics; D014867:Water
chemical_list: D018943:Anthracyclines; D056831:Coordination Complexes; D005290:Ferric Compounds; D006595:Hexosamines; D007477:Ions; D014867:Water; C007217:daunosamine; D015255:Idarubicin