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Issue 10, 2012
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Investigation of isomer formation upon coordination of bifunctional histidine analogues with 99mTc/Re(CO)3

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Abstract

Histidine is a convenient tridentate chelator used in the synthesis of technetium-99m radiopharmaceuticals, as it can be pendantly attached to a biomolecule for molecular imaging applications. Once coordinated, it forms a neutral complex that is capable of forming diastereomers at the alpha amine of the histidine. This is demonstrated through the synthesis and characterization of four different histidine chelators; three small molecule chelators, which consist of a benzylated histidine at the alpha amine, and one modified dipeptide, containing a phenylalanine derivative at the C-terminus and a histidine at the N-terminus. Upon rhenium coordination, two products are observed, each having the desired exact mass of the metal-containing species. The two products have been characterized through LC-MS, 1H, gCOSY, NOESY and ROESY NMR experiments, and the relative stereochemistry determined. The implications of diastereomer formation when using this chelation system for creating molecular imaging agents is also discussed.

Graphical abstract: Investigation of isomer formation upon coordination of bifunctional histidine analogues with 99mTc/Re(CO)3

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Publication details

The article was received on 17 Oct 2011, accepted on 28 Dec 2011 and first published on 23 Jan 2012


Article type: Paper
DOI: 10.1039/C2DT11962E
Citation: Dalton Trans., 2012,41, 2950-2958
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    Investigation of isomer formation upon coordination of bifunctional histidine analogues with 99mTc/Re(CO)3

    E. J. Simpson, J. L. Hickey, D. Breadner and L. G. Luyt, Dalton Trans., 2012, 41, 2950
    DOI: 10.1039/C2DT11962E

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