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A Preorganized Metalloreceptor for Alkaline Earth Ions Showing Calcium Versus Magnesium Selectivity in Water: Biological Activity of Selected Metal Complexes
Author(s) -
Amatori Stefano,
Ambrosi Gianluca,
Fanelli Mirco,
Formica Mauro,
Fusi Vieri,
Giorgi Luca,
Macedi Eleonora,
Micheloni Mauro,
Paoli Paola,
Rossi Patrizia
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201403084
Subject(s) - chemistry , alkaline earth metal , magnesium , metal , metal ions in aqueous solution , calcium , maltol , selectivity , ion , alkali metal , naked eye , inorganic chemistry , stereochemistry , crystallography , nuclear chemistry , medicinal chemistry , biochemistry , organic chemistry , chromatography , detection limit , catalysis
The N , N ′‐bis[(3‐hydroxy‐4‐pyron‐2‐yl)methyl]‐ N , N ′‐dimethylethylendiamine (Malten= L ) forms the highly stable [CuH −2 L ] species in water, in which the converging maltol oxygen atoms form an electron‐rich area able to host hard metal ions. When considering the alkaline earth series (AE), the [Cu(H −2 L )] species binds all metal ions, with the exception of Mg 2+ , exhibiting the relevant property to discriminate Ca 2+ versus Mg 2+ at physiological pH 7.4; the binding of the AE metal is visible to the naked eye. The stability constant values of the trinuclear [AE{Cu(H −2 L )} 2 ] 2+ species formed reach the maximum for Ca 2+ (log K =7.7). Ca 2+ also forms a tetranuclear [Ca{Cu(H −2 L )}] 2 4+ species at a high Ca 2+ concentration. Tri‐ and tetranuclear calcium complexes show blue‐ and pink‐colored crystals, respectively. [Cu(H −2 L )] is the most active species in inducing DNA alterations. The DNA damages are compatible with its hydrolytic cleavages.