The thulium complex of 1,4,7,10-tetrakis {[N-(1H-imidazol-2-yl)-carbamoyl]methyl]-1,4,7,10-tetraazacyclododecane (dotami) as a paraCEST contrast agent

Dirk Burdinski, Johan Lub, Jeroen A. Pikkemaat, Sander Langereis, Holger Grüll, Wolter ten Hoeve

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    Abstract

    1,4,7,10-Tetrakis{[N-(1H-imidazol-2-yl)carbamoyl]methyl}-1,4,7, 10-tetraazacyclododecane (dotami), a tetra(1H-imidazol-2-yl) derivative of the well-studied octadentate 1,4,7,10-tetrakis[(carbamoyl)methyl]- 1,4,7,10-tetraazacyclododecane (dotam) ligand, was synthesized by reaction of 1,4,7,10-tetraazacyclododecane with N-(1H-imidazol-2-yl) chloroacetamide in high yield. Its tricationic thulium complex was isolated as a water-soluble chloride salt. The detection of the mildly acidic amide and amine protons by direct proton NMR in aqueous solution was unsuccessful, but such exchangeable protons could be detected via their chemical exchange-dependent saturation transfer (CEST) effect. The observed CEST effect was distinctly different from that found for respective dotam complexes and is, therefore, ascribed to exchangeable protons associated with the imidazole substituent.

    Original languageEnglish
    Pages (from-to)1505-1512
    Number of pages8
    JournalChemistry and Biodiversity
    Volume5
    Issue number8
    DOIs
    Publication statusPublished - 1 Dec 2008

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