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Functionalized Ruthenium Complexes: Selective “Turn‐on” Detection of Biologically Relevant Anionic Species
Author(s) -
Berni Emanuela,
Le Henaff Laurent,
Jarrige Lucie,
Girard Emeline,
Jonusauskas Gediminas,
Gosse Isabelle,
Pinet Sandra
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700586
Subject(s) - chemistry , ruthenium , selectivity , pyrophosphate , combinatorial chemistry , ligand (biochemistry) , hydrogen bond , stacking , adenosine diphosphate , nucleotide , stereochemistry , organic chemistry , receptor , molecule , catalysis , enzyme , biochemistry , platelet , platelet aggregation , gene , immunology , biology
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.