Rhenium and technetium tricarbonyl complexes of N-Heterocyclic carbene ligands

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dc.contributor.authorChan, CYen_AU
dc.contributor.authorPellegrini, PAen_AU
dc.contributor.authorGreguric, Ien_AU
dc.contributor.authorBarnard, PJen_AU
dc.date.accessioned2018-09-21T01:13:47Zen_AU
dc.date.available2018-09-21T01:13:47Zen_AU
dc.date.issued2014-10-03en_AU
dc.date.statistics2018-09-20en_AU
dc.description.abstractA strategy for the conjugation of N-heterocyclic carbene (NHC) ligands to biomolecules via amide bond formation is described. Both 1-(2-pyridyl)imidazolium or 1-(2-pyridyl)benzimidazolium salts functionalized with a pendant carboxylic acid group were prepared and coupled to glycine benzyl ester using 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide. A series of 10 rhenium(I) tricarbonyl complexes of the form [ReX(CO)3(ĈN)] (ĈN is a bidentate NHC ligand, and X is a monodentate anionic ligand: Cl–, RCO2–) were synthesized via a Ag2O transmetalation protocol from the Re(I) precursor compound Re(CO)5Cl. The synthesized azolium salts and Re(I) complexes were characterized by elemental analysis and by 1H and 13C NMR spectroscopy, and the molecular structures for one imidazolium salt and seven Re(I) complexes were determined by single-crystal X-ray diffraction. 1H NMR and mass spectrometry studies for an acetonitrile-d3 solution of [ReCl(CO)3(1-(2-pyridyl)-3-methylimidazolylidene)] show that the monodentate chloride ligand is labile and exchanges with this solvent yielding a cationic acetonitrile adduct. For the first time the labeling of an NHC ligand with technetium-99m is reported. Rapid Tc-99m labeling was achieved by heating the imidazolium salt 1-(2-pyridyl)-3-methylimidazolium iodide and Ag2O in methanol, followed by the addition of fac-[99mTc(OH2)3(CO)3]+. To confirm the structure of the 99mTc-labeled complex, the equivalent 99Tc complex was prepared, and mass spectrometric studies showed that the formed Tc complexes are of the form [99m/99Tc(CH3CN)(CO)3(1-(2-pyridyl)-3-methylimidazolylidene)]+ with an acetonitrile molecule coordinated to the metal center. © 2014 American Chemical Societyen_AU
dc.identifier.citationChan, C. Y., Pellegrini, P. A., Greguric, I., & Barnard, P. J. (2014). Rhenium and technetium tricarbonyl complexes of N-heterocyclic carbene ligands. Inorganic chemistry, 53(20), 10862-10873. doi:10.1021/ic500917sen_AU
dc.identifier.govdoc8695en_AU
dc.identifier.issn1520-510Xen_AU
dc.identifier.issue20en_AU
dc.identifier.journaltitleInorganic chemistryen_AU
dc.identifier.pagination10862-10873en_AU
dc.identifier.urihttp://doi.org/10.1021/ic500917sen_AU
dc.identifier.urihttp://apo.ansto.gov.au/dspace/handle/10238/9031en_AU
dc.identifier.volume53en_AU
dc.language.isoenen_AU
dc.publisherAmerican Chemical Societyen_AU
dc.subjectCarboxylic acidsen_AU
dc.subjectSaltsen_AU
dc.subjectMoleculesen_AU
dc.subjectPeptidesen_AU
dc.subjectTechnetiumen_AU
dc.subjectDiseasesen_AU
dc.subjectRadiopharmaceuticalsen_AU
dc.subjectRadiochemistryen_AU
dc.subjectLigandsen_AU
dc.titleRhenium and technetium tricarbonyl complexes of N-Heterocyclic carbene ligandsen_AU
dc.typeJournal Articleen_AU
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