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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, OC; Baguña Torres, J; Holt, KB; Blower, PJ; Went, MJ; (2017) Copper complexes with dissymmetrically substituted bis(thiosemicarbazone) ligands as a basis for PET radiopharmaceuticals: control of redox potential and lipophilicity. Dalton Transactions , 46 pp. 14612-14630. 10.1039/c7dt02008b. Green open access

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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.

Type: Article
Title: Copper complexes with dissymmetrically substituted bis(thiosemicarbazone) ligands as a basis for PET radiopharmaceuticals: control of redox potential and lipophilicity
Location: England
Open access status: An open access version is available from UCL Discovery
DOI: 10.1039/c7dt02008b
Publisher version: http://doi.org/10.1039/c7dt02008b
Language: English
Additional information: This version is the author accepted manuscript. For information on re-use, please refer to the publisher’s terms and conditions.
UCL classification: UCL
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry
URI: https://discovery.ucl.ac.uk/id/eprint/1565167
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