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Esterification vs 1,3-dipolar cycloaddition synthetic approaches for preparation of the fluorescently labelled iron(II) clathrochelates

Roman A. Selin,1,@ Viktor Ya. Chernii,1 Dmytro V. Kryvorotenko,2 Andriy Mokhir,3 Yan Z. Voloshin4,5,@
1Vernadskii Institute of General and Inorganic Chemistry NASU, 32/34 Palladin Prosp., 03080 Kiev, Ukraine.
2Institute of Molecular Biology and Genetics, NASU, 150 Zabolotnogo St., 03143 Kyiv, Ukraine.
3Organic Chemistry II, Friedrich-Alexander-University of Erlangen–Nuremberg, 42 Henke st., 91054 Erlangen, German.
4Kurnakov Institute of General and Inorganic Chemistry of the Russian Academy of Sciences, 31 Leninsky Prosp., 119991 Moscow, Russia.
5Nesmeyanov Institute of the Organoelement Compounds of the Russian Academy of Sciences, 28 Vavilova St., 119991 Moscow, Russia.
 

Two most common synthetic approaches (i.e. the esterification and 1,3-dipolar cycloaddition reactions) to a functionalization of the reactive three-dimensional molecular platforms, allowing to obtain the fluorescently labeled iron(II) clathrochelates and, therefore, to study their localization and accumulation in cancer cells, were compared. Because an esterification approach gave them in very low, if any, yields, such functionalization of a known propargylamine iron(II) clathrochelate complex with terminal CºC bond as a reactive macrobicyclic precursor by the copper-promoted 1,3-dipolar cycloaddition “click”-reaction was also tested. This one-pot synthetic procedure allowed to obtain the cumarin-terminated iron(II) cage complex in the high yield; it was characterized using elemental analysis, ESI-TOF mass, and 1H and 13C{1H} NMR spectra.