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Curcumin as the OO Bidentate Ligand in “2 + 1” Complexes with the [M(CO)3]+ (M = Re, 99mTc) Tricarbonyl Core for Radiodiagnostic Applications

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† Institute of Biology
‡ Institute of Radioisotopes/Radiodiagnostic Products
§ Institute of Materials Science
National Centre for Scientific Research “Demokritos”, 15310 Athens, Greece
*To whom correspondence should be addressed. Telephone: +30210 6503555. Fax: +30210 6511767. E-mail: [email protected]
Cite this: Inorg. Chem. 2011, 50, 4, 1295–1303
Publication Date (Web):January 21, 2011
https://doi.org/10.1021/ic102228u
Copyright © 2011 American Chemical Society
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    Abstract

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    The synthesis and characterization of “2 + 1” complexes of the [M(CO)3]+ (M = Re, 99mTc) core with the β-diketones acetylacetone (complexes 2, 8) and curcumin (complexes 5, 10 and 6, 11) as bidentate OO ligands, and imidazole or isocyanocyclohexane as monodentate ligands is reported. The complexes were synthesized by reacting the [NEt4]2[Re(CO)3Br3] precursor with the β-diketone to generate the intermediate aqua complex fac-Re(CO)3(OO)(H2O) that was isolated and characterized, followed by replacement of the labile water by the monodentate ligand. All complexes were characterized by mass spectrometry, NMR and IR spectroscopies, and elemental analysis. In the case of complex 2, bearing imidazole as the monodentate ligand, X-ray analysis was possible. The chemistry was successfully transferred at 99mTc tracer level. The curcumin complexes 5 and 6, as well as their intermediate aqua complex 4, that bear potential for radiopharmaceutical applications due to the wide spectrum of pharmacological activity of curcumin, were successfully tested for selective staining of β-amyloid plaques of Alzheimer’s disease. The fact that the complexes maintain the affinity of the mother compound curcumin for β-amyloid plaques prompts for further exploration of their chemistry and biological properties as radioimaging probes.

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    1H and 13C spectra of NMR spectra of imidazole in DMSO-d6; NOESY spectrum of complex 2; 1H NMR spectrum of complex 4; IR spectrum of complex 6; UV absorbance and fluorescence spectra of curcumin and complexes 5 and 6; β-amyloid plaque staining with thioflavin S, complex 6, and curcumin. This material is available free of charge via the Internet at http://pubs.acs.org.

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