Issue 23, 2003

Structural trends in copper(ii) bis(thiosemicarbazone) radiopharmaceuticals

Abstract

Redox-related changes in biological properties of copper bis(thiosemicarbazone) radiopharmaceuticals are induced by backbone alkylation. To determine whether these changes are mediated by changes in core structural parameters, eight X-ray structures of variously alkylated complexes were determined. The complexes include the hypoxia tracer diacetylbis(4-methyl-3-thiosemicarbazonato)copper(II) (CuATSM). The structures of the nickel analogue NiATSM and the corresponding free ligand ATSMH2 were also included. Distortions from planarity were slight and only present when there were significant intermolecular interactions (mainly pairs of N–H–N and N–H–S hydrogen bonds). These give rise to cross-linked flat or helical ribbons of complexes. Alkylation at the terminal nitrogen atoms interrupts hydrogen bonding, allowing complexes to become planar, but does not otherwise affect the coordination sphere. Alkylation at the backbone carbon atoms increases the backbone C–C bond length, allowing the metal to fit better into the ligand cavity with shorter Cu–S bonds.

Graphical abstract: Structural trends in copper(ii) bis(thiosemicarbazone) radiopharmaceuticals

Supplementary files

Article information

Article type
Paper
Submitted
01 Jul 2003
Accepted
16 Sep 2003
First published
30 Sep 2003

Dalton Trans., 2003, 4416-4425

Structural trends in copper(II) bis(thiosemicarbazone) radiopharmaceuticals

P. J. Blower, T. C. Castle, A. R. Cowley, J. R. Dilworth, P. S. Donnelly, E. Labisbal, F. E. Sowrey, S. J. Teat and M. J. Went, Dalton Trans., 2003, 4416 DOI: 10.1039/B307499D

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