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 |
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Authors: | Burdinski Dirk Lub Johan Pikkemaat Jeroen A Langereis Sander Grüll Holger ten Hoeve Wolter |
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Institution: | Department of Bio-Molecular Engineering, Philips Research, High Tech Campus 11, NL-5656 AE Eindhoven. dirk.burdinski@philips.com |
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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. |
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Keywords: | Macrocyclic ligands Thulium complexes Magnetization transfer Chemical exchange‐dependent saturation transfer (CEST) MRI Contrast agents dotam Derivatives |
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