Orthopalladated acetophenone oxime compounds bearing thioamides as ligands: Synthesis, structure and cytotoxic evaluation

Author(s):Show less -

de Souza, Ronan F. F. ^[1] ; da Cunha, Gislaine A. ^[1] ; Pereira, Jose C. M. ^[1] ; Garcia, Daniel M. ^[2] ; Bincoletto, Claudia ^[2] ; Goto, Renata N. ^[3] ; Leopoldino, Andreia M. ^[3] ; da Silva, Isabel C. ^[4] ; Pavan, Fernando R. ^[4] ; Deflon, Victor M. ^[5] ; de Almeida, Eduardo T. ^[6] ; Mauro, Antonio E. ^[1] ; Netto, Adelino V. G. ^[1]

Affiliation

^[1] Univ Estadual Paulista, Inst Quim, Dept Quim Geral & Inorgan, UNESP, BR-14800060 Araraquara, SP - Brazil

^[2] UNIFESP Univ Fed Sao Paulo, Escola Paulista Med, Dept Farmacol, BR-04044020 Sao Paulo, SP - Brazil

^[3] Univ Sao Paulo, Fac Ciencias Farmaceut Ribeirao Preto, BR-14040903 Ribeirao Preto, SP - Brazil

^[4] Univ Estadual Paulista, Fac Ciencias Farmaceut, UNESP, BR-14800903 Araraquara, SP - Brazil

^[5] Univ Sao Paulo, Inst Quim Sao Carlos, BR-13560970 Sao Carlos, SP - Brazil

^[6] UNIFAL Univ Fed Alfenas, Inst Quim, BR-37130001 Alfenus, MG - Brazil

• Document type: Journal article
• Source: Inorganica Chimica Acta; v. 486, p. 617-624, FEB 24 2019.
• Web of Science Citations: 2

Abstract

Cleavage reactions involving the halide-bridged {[}Pd(mu-Cl)(C-2,N-aphox)](2) precursor (aphox = acetophenone oxime) with thioamides, in the 1:2 molar ratio, yielded mononuclear cyclopalladated of the type {[}Pd(C-2,N-aphox)(Cl)(L) = thiourea (1); N-methylthiourea (2); N,N'-dimethylthiourea (3); N-phenylthiourea (4); N,N'-diphenylthiour ea (5); thioacetamide (6) and benzothioamide (7)] which were characterized by elemental analyses, infrared and H-1 and C-13[H-1]-NMR spectroscopies. The crystal and molecular structures of 1, 3 and 6 were determined by single-crystal X-ray diffraction studies. The cytotoxicity of the cyclopalladated compounds has been evaluated against a panel of murine [breast (4T1) and melanoma (B16F10-Nex2)] and human [melanoma (A2058, SK-Mel-110 and SK-Mel-05), oral squamous cell carcinoma (Cal27), hepatocellular carcinoma (HepG2)] cancer cell lines. All studied compounds were cytotoxic for the seven cancer cell lines studied and in general, most cyclopalladated compounds obtained in this work were more active than cisplatin to the seven tumor cell lines evaluated. (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