N-Heterocyclic Carbene Platinum(IV) as Metallodrug Candidates: Synthesis and 195Pt NMR Chemical Shift Trend

Bouché, Mathilde; Vincent, Bruno; Achard, Thierry; Bellemin-Laponnaz, Stéphane

doi:10.3390/molecules25143148

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N-Heterocyclic Carbene Platinum(IV) as Metallodrug Candidates: Synthesis and ¹⁹⁵Pt NMR Chemical Shift Trend

Mathilde Bouché

Bruno Vincent

²,

Thierry Achard

and

Stéphane Bellemin-Laponnaz

^1,*

Institut de Physique et Chimie des Matériaux de Strasbourg, Université de Strasbourg-CNRS UMR7504, 23 rue du Loess, BP 43 CEDEX 2, 67034 Strasbourg, France

Service de RMN, Fédération de Chimie Le Bel, Université de Strasbourg, CNRS FR2010, 1 rue Blaise Pascal, BP 296R8, CEDEX, 67008 Strasbourg, France

Author to whom correspondence should be addressed.

Academic Editor: Yves Canac

Molecules 2020, 25(14), 3148; https://doi.org/10.3390/molecules25143148

Received: 19 June 2020 / Revised: 6 July 2020 / Accepted: 8 July 2020 / Published: 9 July 2020

(This article belongs to the Special Issue Carbon Ligands: From Fundamental Aspects to Applications)

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Abstract

A series of octahedral platinum(IV) complexes functionalized with both N-heterocyclic carbene (NHC) ligands were synthesized according to a straightforward procedure and characterized. The coordination sphere around the metal was varied, investigating the influence of the substituted NHC and the amine ligand in trans position to the NHC. The influence of those structural variations on the chemical shift of the platinum center were evaluated by ¹⁹⁵Pt NMR. This spectroscopy provided more insights on the impact of the structural changes on the electronic density at the platinum center. Investigation of the in vitro cytotoxicities of representative complexes were carried on three cancer cell lines and showed IC₅₀ values down to the low micromolar range that compare favorably with the benchmark cisplatin or their platinum(II) counterparts bearing NHC ligands. View Full-Text

Keywords: N-heterocyclic carbene; platinum; metal complexes; ¹⁹⁵Pt NMR

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Bouché, M.; Vincent, B.; Achard, T.; Bellemin-Laponnaz, S. N-Heterocyclic Carbene Platinum(IV) as Metallodrug Candidates: Synthesis and ¹⁹⁵Pt NMR Chemical Shift Trend. Molecules 2020, 25, 3148. https://doi.org/10.3390/molecules25143148

AMA Style

Bouché M, Vincent B, Achard T, Bellemin-Laponnaz S. N-Heterocyclic Carbene Platinum(IV) as Metallodrug Candidates: Synthesis and ¹⁹⁵Pt NMR Chemical Shift Trend. Molecules. 2020; 25(14):3148. https://doi.org/10.3390/molecules25143148

Chicago/Turabian Style

Bouché, Mathilde, Bruno Vincent, Thierry Achard, and Stéphane Bellemin-Laponnaz. 2020. "N-Heterocyclic Carbene Platinum(IV) as Metallodrug Candidates: Synthesis and ¹⁹⁵Pt NMR Chemical Shift Trend" Molecules 25, no. 14: 3148. https://doi.org/10.3390/molecules25143148

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N-Heterocyclic Carbene Platinum(IV) as Metallodrug Candidates: Synthesis and ¹⁹⁵Pt NMR Chemical Shift Trend

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