Rhenium Complexes Based on an N2O Tridentate Click Scaffold : From Synthesis, Structural and Theoretical Characterization to a Radiolabelling Study Article - Janvier 2017

Romain Eychenne, Sihem Guizani, Jin-Hui Wang, Claude Picard, Nadia Malek, Paul-Louis Fabre, Mariusz Wolff, Barbara Machura, Nathalie Saffon, Nicolas Lepareur, Eric Benoist

Romain Eychenne, Sihem Guizani, Jin-Hui Wang, Claude Picard, Nadia Malek, Paul-Louis Fabre, Mariusz Wolff, Barbara Machura, Nathalie Saffon, Nicolas Lepareur, Eric Benoist, « Rhenium Complexes Based on an N2O Tridentate Click Scaffold : From Synthesis, Structural and Theoretical Characterization to a Radiolabelling Study  », European Journal of Inorganic Chemistry, janvier 2017, pp. 69-81. ISSN 1434-1948

Abstract

A general synthetic approach to a novel range of semirigid bifunctional chelating agents (BCAs) that include an aromatic ring and a triazolyl moiety in the chelating unit has been investigated for the fac‐[M(CO)3]+ core (M = 185/187Re or 188Re). The strategy includes the facile preparation of these N2O ligands bearing various functionalized arms (carboxylate, terminal alkyne, aromatic amine). The reaction of commercial [Re(CO)5Cl] or a freshly prepared [Re(OH2)3(CO)3]+ precursor with our BCAs in methanol led to the formation of stable neutral tricarbonylrhenium complexes of general formula [Re(CO)3(L)] (LH = 5, 10, 11) in high yields. These compounds were characterized by IR and NMR spectroscopy, mass spectrometry, electrochemistry, and X‐ray crystallography for [Re(CO)3(5–H)] and [Re(CO)3(11–H)] as well as by DFT calculations. The analogous rhenium‐188 complexes [188Re(CO)3(5)] and [188Re(CO)3(11–H)] were also prepared, in acceptable to excellent yields, by the reaction of 5 or 11 with the fac‐[188Re(OH2)3(CO)3]+ precursor in methanol at 80 °C. The structural identities of the radioactive complexes were assessed by HPLC studies. The good affinity of these click ligands for the ReI core combined with the ease of their derivatization make this chelating system promising for the conception of target‐specific radiopharmaceuticals for therapeutic purposes.

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