Department of Pharmacy, King's College London, Franklin-Wilkins Building, 150 Stamford Street, London SE1 9NH, UK.
Bioorg Med Chem. 2009 Dec 1;17(23):8093-101. doi: 10.1016/j.bmc.2009.09.052. Epub 2009 Oct 8.
The synthesis of four hexadentate fluorescent probes is described, where the fluorescent moiety is based on either coumarin or fluorescein and the chelating moiety is based on either 3-hydroxypyridin-4-one or 3-hydroxypyran-4-one. The fluorescence is quenched when the probe chelating moieties bind iron. The probes were found to be selective for iron over other metals such as Cu, Zn, Ni, Mn and Co. The effect of Cu on fluorescence quenching can be eliminated in the presence of N,N,N',N'-tetrakis(2-pyridylmethyl)-ethylenediamine. Competition studies demonstrate that the exchange of iron between pyridinone-based probes and apotransferrin is very slow. The ability to scavenge iron from oligomeric iron(III) citrate complexes demonstrate that the pyridinone probes scavenges iron faster than deferiprone and desferrioxamine. The fluorescence intensity of the fluorescein-based probe is quantitatively related to the iron concentration with the limit of detection being 10(-8)M.
描述了四种六齿荧光探针的合成，其中荧光部分基于香豆素或荧光素，螯合部分基于 3-羟基吡啶-4-酮或 3-羟基吡喃-4-酮。当探针螯合部分与铁结合时，荧光被猝灭。这些探针被发现对铁具有选择性，而对其他金属如 Cu、Zn、Ni、Mn 和 Co 则没有选择性。在存在 N,N,N',N'-四(2-吡啶基甲基)乙二胺的情况下，可以消除 Cu 对荧光猝灭的影响。竞争研究表明，基于吡啶酮的探针与脱铁转铁蛋白之间的铁交换非常缓慢。从低聚铁(III)柠檬酸盐配合物中清除铁的能力表明，吡啶酮探针清除铁的速度比去铁酮和去铁胺快。基于荧光素的探针的荧光强度与铁浓度呈定量关系，检测限为 10(-8)M。
