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

Brown, Oliver C., Baguña Torres, Julia, Holt, Katherine B., Blower, Philip J., Went, Michael J. (2017) Copper complexes with dissymmetrically substituted bis(thiosemicarbazone) ligands as a basis for PET radiopharmaceuticals: control of redox potential and lipophilicity. Dalton Transactions, (42). pp. 14612-14630. ISSN 1477-9226. E-ISSN 1477-9234. (doi:10.1039/C7DT02008B)

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Official URL
https://doi.org/10.1039/C7DT02008B

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.

Item Type: Article
DOI/Identification number: 10.1039/C7DT02008B
Subjects: Q Science
Divisions: Faculties > Sciences > School of Physical Sciences > Functional Materials Group
Depositing User: Michael J Went
Date Deposited: 07 Jul 2017 08:27 UTC
Last Modified: 12 Jul 2019 14:01 UTC
Resource URI: https://kar.kent.ac.uk/id/eprint/62230 (The current URI for this page, for reference purposes)
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