Issue 43, 2020

Two new monofunctional platinum(ii) dithiocarbamate complexes: phenanthriplatin-type axial protection, equatorial-axial conformational isomerism, and anticancer and DNA binding studies

Abstract

The syntheses of two platinum(II) dithiocarbamate complexes (1 and 2) that show quinoplatin- and phenanthriplatin-type axial protection of the Pt-plane are described. The Pt-plane of complex 2 is axially more protected than that of complex 1. Furthermore, both complexes adopt two different stereochemical conformations in the solid state (based on single-crystal X-ray structures) owing to the structurally flexible piperazine backbone; i.e., C-e,e-Anti (1) and C-e,a-Syn (2), where “C” stands for the chair configuration, “e” and “a” stand for the equatorial and axial positions and “Anti” (opposite side) and “Syn” (same side) represent the relative orientations in space of the terminal substituents on the piperazine ring. In complex 2, the C-e,a-Syn conformation may provide additional steric hindrance to the Pt-plane. Despite the lower lipophilicity of 2 as compared to that of 1, the in vitro anticancer action against selected cancer cell lines is better for the former revealing the superior role of the axial protection over lipophilicity in modulating anticancer activity. The activity against the cancer promoting protein NF-κB signifies that the mode of cancer cell death may be the result of hindering the activity of NF-κB in the initiation of apoptosis. The apoptotic mode of cell death has been established earlier in a study using Annexin V-FITC. Finally, DNA binding studies revealed that the complex-DNA adduct formation is spontaneous and the mode of interaction is non-intercalative (electrostatic/covalent).

Graphical abstract: Two new monofunctional platinum(ii) dithiocarbamate complexes: phenanthriplatin-type axial protection, equatorial-axial conformational isomerism, and anticancer and DNA binding studies

Supplementary files

Article information

Article type
Paper
Submitted
28 Aug 2020
Accepted
06 Oct 2020
First published
07 Oct 2020

Dalton Trans., 2020,49, 15385-15396

Two new monofunctional platinum(II) dithiocarbamate complexes: phenanthriplatin-type axial protection, equatorial-axial conformational isomerism, and anticancer and DNA binding studies

M. Imran, Z. U. Rehman, G. Hogarth, D. A. Tocher, G. Chaudhry, I. S. Butler, F. Bélanger-Gariepy and T. Kondratyuk, Dalton Trans., 2020, 49, 15385 DOI: 10.1039/D0DT03018J

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