BERNI, Emanuela; LE HENAFF, Laurent; JARRIGE, Lucie; GIRARD, Emeline; JONUSAUSKAS, Gediminas; GOSSE, Isabelle; PINET, Sandra

doi:10.1002/ejoc.201700586

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BERNI, Emanuela
Institut des Sciences Moléculaires [ISM]

LE HENAFF, Laurent
Institut des Sciences Moléculaires [ISM]

JARRIGE, Lucie
Institut des Sciences Moléculaires [ISM]

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European Journal of Organic Chemistry. 2017, vol. 2017, n° 25, p. 3620-3630

Wiley-VCH Verlag

Résumé en anglais

To study the effect of the structure of 3,3′-modified bipyridyl ruthenium complexes on their ability to recognize organic anions, various ruthenium complexes have been prepared. The binding functions and large-sized modified bipyridyl ligand turned out to be essential for selectivity in acetonitrile. The selectivity for dicarboxylates or phosphates can be switched by using guanidinium- or ammonium-functionalized probes. One of these probes turned out to be selective towards glutamate over aspartate and γ-aminobutyric acid (GABA). Another was selective towards adenosine 5′-triphosphate (ATP) over adenosine 5′-diphosphate (ADP), pyrophosphate (PPi), adenosine 5′-monophosphate (AMP), and orthophosphate (Pi). In both cases, the binding was attributed to coulombic interactions and hydrogen bonding. π-stacking interactions also occurred with nucleotides. Replacing ammonium by zinc-dipicolylamine units made possible the recognition of phosphorylated species in buffered aqueous systems. To our delight, this probe showed selectivity for ADP over ATP and we proved that the selectivity was partly due to substitution at the 3- and 3′-positions of the ligand.< Réduire

Mots clés en anglais

Molecular recognition

Luminescence

Ruthenium

Glutamate

Nucleotides

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Functionalized Ruthenium Complexes: Selective “Turn-on” Detection of Biologically Relevant Anionic Species

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