Orthopalladated tetralone oxime compounds bearing tertiary phosphines: Synthesis, structure, biological and in silico studies

Author(s):Show less -

Velasques, Jecika M. ^[1] ; de Souza, Ronan F. F. ^[1] ; Silva, Debora E. S. ^[1] ; Farias, Renan L. ^[1] ; Zanetti, Renan D. ^[1] ; Moreira, Mariete B. ^[2] ; Ellena, Javier ^[3] ; Pereira, Jose C. M. ^[1] ; Mauro, Antonio E. ^[1] ; Oliveira, Adriano B. ^[4] ; Netto, Adelino V. G. ^[1]

Affiliation

^[1] UNESP Univ Estadual Paulista, Inst Chem, Dept Analyt Phys Chem & Inorgan Chem, BR-14800060 Araraquara, SP - Brazil

^[2] UEL Univ Estadual Londrina, Dept Quim, BR-86051990 Londrina, Parana - Brazil

^[3] Univ Sao Paulo, Inst Fis Sao Carlos, BR-13566590 Sao Carlos, SP - Brazil

^[4] UFS Univ Fed Sergipe, Dept Quim, BR-49100000 Sao Cristovao, SE - Brazil

• Document type: Journal article
• Source: JOURNAL OF ORGANOMETALLIC CHEMISTRY; v. 958, JAN 15 2022.
• Web of Science Citations: 0

Abstract

The halido- alpha-bridge cleavage reactions between {[}Pd( C 2 ,N -tetrox)( mu-Cl)] 2 precursor (tetrox = E- alpha tetralone oxime) with phosphines, in 1:2 molar ratio, have afforded mononuclear cyclopalladated compounds of the type {[}PdCl( C 2 ,N -tetrox)(L)] [ L = triphenylphosphine ( 1 ); tris(4-methylphenyl)phosphine ( 2 ); tris(4-fluorophenyl)phosphine ( 3 ) and tris(4-methoxyphenyl)phosphine ( 4 )]. The compounds have been characterized by elemental analyses, infrared (FT-IR) and 1 H, 13 C[ 1 H] and 31 P[ 1 H]-NMR spectroscopies. The molecular structure of 3 has been determined by single crystal X-ray diffraction (SC-XRD) and the Hirshfeld Surface calculation (HS) has been performed. The antiproliferative activity of compounds 1-4 has been evaluated against breast (MCF-7) and lung (A549) human cancer cells, and human lung fibroblast (MRC-5). All cyclopalladated compounds have been more active than cisplatin against MCF-7 cells, with IC 50 values ranging from 19 to 26 mu M. Binding experiments involving compound 3 with ct-DNA and human serum albumin (HSA) have been carried out using spectroscopic techniques. The interaction between compound 3 and HSA has been studied by means of molecular docking. (c) 2021 Elsevier B.V. All rights reserved. (AU)

• FAPESP's process: 12/15486-3 - Pd(II) compounds: synthesis, cytotoxicity, and DNA binding studies
• Grantee: Regina Celia Galvao Frem
• Support Opportunities: Regular Research Grants
• FAPESP's process: 16/17711-5 - INVESTIGATION OF THE ANTITUMOR POTENTIAL OF PALLADIUM(II) COMPOUNDS CONTAINING ORTHOMETALLATED OR N,S-DONOR LIGANDS
• Grantee: Adelino Vieira de Godoy Netto
• Support Opportunities: Regular Research Grants