Issue 42, 2017

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

Abstract

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
02 Jun 2017
Accepted
06 Jul 2017
First published
06 Jul 2017

Dalton Trans., 2017,46, 14612-14630

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

O. C. Brown, J. Baguña Torres, K. B. Holt, P. J. Blower and M. J. Went, Dalton Trans., 2017, 46, 14612 DOI: 10.1039/C7DT02008B

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