Copper complexes with dissymmetrically substituted bis(thiosemicarbazone) ligands as a basis for PET radiopharmaceuticals: control of redox potential and lipophilicity

Copper( ii ) bis(thiosemicarbazone) derivatives have been used extensively in positron emission tomography (PET) to image hypoxia and blood flow and to radiolabel cells for cell tracking. These applications depend on control of redox potentials and lipophilicity of the bis(thiosemicarbazone) complex...

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Published in:Dalton transactions : an international journal of inorganic chemistry 2017-10, Vol.46 (42), p.14612-1463
Main Authors: Brown, Oliver C, Baguña Torres, Julia, Holt, Katherine B, Blower, Philip J, Went, Michael J
Format: Article
Language:English
Subjects:
Alkylation
Coordination Complexes - chemical synthesis
Coordination Complexes - chemistry
Copper - chemistry
Electrochemistry
Hydrophobic and Hydrophilic Interactions
Ketones - chemistry
Ligands
Oxidation-Reduction
Positron-Emission Tomography - methods
Radiopharmaceuticals - chemical synthesis
Radiopharmaceuticals - chemistry
Thiosemicarbazones - chemistry
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Summary:Copper( ii ) bis(thiosemicarbazone) derivatives have been used extensively in positron emission tomography (PET) to image hypoxia and blood flow and to radiolabel cells for cell tracking. These applications depend on control of redox potentials and lipophilicity of the bis(thiosemicarbazone) complexes, which can be adjusted by altering peripheral ligand substituents. This paper reports the synthesis of a library of new dissymmetrically substituted bis(thiosemicarbazone) ligands by controlling the condensation reactions between dicarbonyl compounds and 4-substituted-3-thiosemicarbazides or using acetal protection. Copper complexes of the new ligands have been prepared by reaction with copper acetate or via transmetallation of the corresponding zinc complexes, which are convenient precursors for the rapid synthesis of radio-copper complexes. Well-defined structure-activity relationships linking ligand alkylation patterns with redox potential and lipophilicity of the complexes are reported. A library of copper( ii ) bis(thiosemicarbazone) complexes offers independently controlled redox potential and lipophilicity for optimal 64 Cu PET tracer design.
ISSN:1477-9226
1477-9234
DOI:10.1039/c7dt02008b