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Synthesis and Characterization of fac-[M(CO)3(P)(OO)] and cis-trans-[M(CO)2(P)2(OO)] Complexes (M = Re, 99mTc) with Acetylacetone and Curcumin as OO Donor Bidentate Ligands

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    Synthesis and Characterization of fac-[M(CO)3(P)(OO)] and cis-trans-[M(CO)2(P)2(OO)] Complexes (M = Re, 99mTc) with Acetylacetone and Curcumin as OO Donor Bidentate Ligands
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    † †Institute of Nuclear and Radiological Sciences and Technology, Energy and Safety, ‡Institute of Biosciences & Applications, and §Institute of Advanced Materials, Physicochemical Processes, Nanotechnology and Microsystems, Department of Materials Science, National Centre for Scientific Research “Demokritos”, 15310 Athens, Greece
    *E-mail: [email protected]. Phone: + 30210 6503909. Fax: + 30210 6503829.
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    Inorganic Chemistry

    Cite this: Inorg. Chem. 2013, 52, 22, 12995–13003
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    https://doi.org/10.1021/ic401503b
    Published November 7, 2013
    Copyright © 2013 American Chemical Society
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    The synthesis and characterization of neutral mixed ligand complexes fac-[M(CO)3(P)(OO)] and cis-trans-[M(CO)2(P)2(OO)] (M = Re, 99mTc), with deprotonated acetylacetone or curcumin as the OO donor bidentate ligands and a phosphine (triphenylphosphine or methyldiphenylphosphine) as the monodentate P ligand, is described. The complexes were synthesized through the corresponding fac-[M(CO)3(H2O)(OO)] (M = Re, 99mTc) intermediate aqua complex. In the presence of phosphine, replacement of the H2O molecule of the intermediate complex at room temperature generates the neutral tricarbonyl monophosphine fac-[Re(CO)3(P)(OO)] complex, while under reflux conditions further replacement of the trans to the phosphine carbonyl generates the new stable dicarbonyl bisphosphine complex cis-trans-[Re(CO)2(P)2(OO)]. The Re complexes were fully characterized by elemental analysis, spectroscopic methods, and X-ray crystallography showing a distorted octahedral geometry around Re. Both the monophosphine and the bisphosphine complexes of curcumin show selective binding to β-amyloid plaques of Alzheimer’s disease. At the 99mTc tracer level, the same type of complexes, fac-[99mTc(CO)3(P)(OO)] and cis-trans-[99mTc(CO)2(P)2(OO)], are formed introducing new donor combinations for 99mTc(I). Overall, β-diketonate and phosphine constitute a versatile ligand combination for Re(I) and 99mTc(I), and the successful employment of the multipotent curcumin as β-diketone provides a solid example of the pharmacological potential of this system.

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    HMBC spectrum of curcuminato complex 8; 1H NMR spectra of complexes 4 and 7; 13C NMR spectra of curcuminato complexes 5 and 8; tables with selected bond distances and angles for 3, 4, and 6–8; HPLC chromatograms of rhenium and technetium-99m complexes and stability studies of the technetium-99m complexes. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Inorganic Chemistry

    Cite this: Inorg. Chem. 2013, 52, 22, 12995–13003
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ic401503b
    Published November 7, 2013
    Copyright © 2013 American Chemical Society
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