Oxime-derived palladacycles bearing 2,6-lutidine: Synthesis, cytotoxicity evaluation and interactions with biomolecules

•New compounds bearing orthopalladated oximes and 2,6-lutidine have been successfully synthesized.•Their molecular and crystal structures have been determined by single-crystal X-ray crystallography.•Compounds showed IC50 values in the range 3–8 µM against MDA-MB-231 cancer cells.•The orthopalladate...

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Veröffentlicht in:Journal of molecular structure 2025-02, Vol.1321, p.140232, Article 140232
Hauptverfasser: Polez, Ana M.R., Farias, Renan L., de Lima, Andresa A., Lazzarini, Ana Beatriz, de Moura, Thales R., Velasques, Jecika M., Souza, Jessica Carolina, Rocha, Fillipe V., Lima, Mauro Almeida, Ellena, Javier, Miranda, Victor Maia, Deflon, Victor M., Moreira, Mariete B., Netto, Adelino V.G.
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Sprache:eng
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Zusammenfassung:•New compounds bearing orthopalladated oximes and 2,6-lutidine have been successfully synthesized.•Their molecular and crystal structures have been determined by single-crystal X-ray crystallography.•Compounds showed IC50 values in the range 3–8 µM against MDA-MB-231 cancer cells.•The orthopalladated tetraloneoxime derivative interacted with DNA through non-intercalative binding mode. In this study, we report the synthesis, characterization and biological studies on new organometallic compounds bearing orthopalladated oximes and 2,6-lutidine. Cyclopalladated compounds of the type [PdCl(C2,N-ox)(lut)] {ox: bzox = benzaldehydeoxime (1), aphox = acetophenoneoxime (2), tetrox = E-α-tetralone oxime (3); lut = 2,6-lutidine} have been obtained from the reaction between the suitable [Pd(C2,N-ox)(µ-Cl)]2 precursor with 2,6-lutidine. The compounds have been characterized by elemental analyses, infrared (IR) and NMR spectroscopies. The molecular and crystal structures of 1 – 3 have been determined by single-crystal X-ray crystallography. The cytotoxic activity of compounds 1–3 has been evaluated towards breast (MCF-7 and MD-MBA-231) and lung (A549) human cancer cells along with human lung fibroblast (MRC-5). The level of cytotoxicity is dependent on the tested tumour cell line and the type of orthometallated oxime. The binding properties of the model compound 3 on ct-DNA have been studied using UV–Vis titration, circular dichroism and fluorescence spectroscopy. [Display omitted]
ISSN:0022-2860
DOI:10.1016/j.molstruc.2024.140232