Department of Chemistry, University of Warsaw, Pasteura 1, Warsaw 02-093, Poland.
J Phys Chem B. 2013 Jun 13;117(23):6868-73. doi: 10.1021/jp4023508. Epub 2013 May 31.
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.
我们研究了甲氧基和 daunosamine 糖基对水溶液中阿霉素与 Fe(3+) 配合物稳定性的影响。柔红霉素和 daunorubicin 在结构上非常相似，仅在 4 位上存在甲氧基取代基。我们证明甲氧基基团与近侧醌氧原子发生空间相互作用，这种相互作用影响阿霉素-铁（III）配合物的稳定性。类似的空间效应也见于悬垂的 daunosamine 部分。溶液中的游离 daunosamine 与铁（III）没有任何显著相互作用，而悬垂的 daunosamine 部分使阿霉素-铁（III）配合物的形成不稳定。这组信息说明了甲氧基和 daunosamine 部分在阿霉素-铁（III）配合物形成和稳定性中的重要作用。
