Silver(I) Complexes Based on Oxadiazole-Functionalized α -Aminophosphonate: Synthesis, Structural Study, and Biological Activities.

Publisher: MDPI Country of Publication: Switzerland NLM ID: 100964009 Publication Model: Electronic Cited Medium: Internet ISSN: 1420-3049 (Electronic) Linking ISSN: 14203049 NLM ISO Abbreviation: Molecules Subsets: MEDLINE

Original Publication: Basel, Switzerland : MDPI, c1995-

Silver*/pharmacology ; Silver*/chemistry ; Organophosphonates*/pharmacology; Ligands ; Oxadiazoles/pharmacology ; Molecular Docking Simulation ; Vascular Endothelial Growth Factor A

Two silver(I) complexes, bis{diethyl[(5-phenyl-1,3,4-oxadiazol-2-yl-κ N ³ :κ N ⁴ -amino) (4-trifluoromethylphenyl)methyl]phosphonate-(tetrafluoroborato-κ F )}-di-silver(I) and tetrakis-{diethyl[(5-phenyl-1,3,4-oxadiazol-2-yl-κ N ³ -amino)(4-trifluoromethylphenyl)methyl]phosphonate} silver(I) tetrafluoroborate, were prepared starting from the diethyl[(5-phenyl-1,3,4-oxadiazol-2-yl-amino)(4-trifluoromethylphenyl)methyl]phosphonate ( 1 ) ligand and AgBF 4 salt in Ag/ligand ratios of 1/1 and 1/4, respectively. The structure, stoichiometry, and geometry of the silver complexes were fully characterized by elemental analyses, infrared, single-crystal X-ray diffraction studies, multinuclear NMR, and mass spectroscopies. The binuclear complex ([Ag 2 ( 1 ) 2 (BF 4 ) 2 ]; 2 ) crystallizes in the monoclinic asymmetric space group P 2 1 /c and contains two silver atoms adopting a {AgN 2 F} planar trigonal geometry, which are simultaneously bridged by two oxadiazole rings of two ligands, while the mononuclear complex ([Ag( 1 ) 4 ]BF 4 ; 3 ) crystallizes in the non-usual cubic space group Fd-3 c in which the silver atom binds to four distinct electronically enriched nitrogen atoms of the oxadiazole ring, in a slightly distorted {AgN 4 } tetrahedral geometry. The α -aminophosphonate and the monomeric silver complex were evaluated in vitro against MCF-7 and PANC-1 cell lines. The silver complex is promising as a drug candidate for breast cancer and the pancreatic duct with half-maximal inhibitory concentration (IC 50 ) values of 8.3 ± 1.0 and 14.4 ± 0.6 μM, respectively. Additionally, the interactions of the ligand and the mononuclear complex with Vascular Endothelial Growth Factor Receptor-2 and DNA were evaluated by molecular docking methods.

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Keywords: 1,3,4-oxadiazole; MCF-7 cell line; PANC-1 cell line; X-ray structure; in vitro cytotoxicity; molecular docking; silver(I) complex

3M4G523W1G (Silver)
0 (Ligands)
0 (Oxadiazoles)
0 (Vascular Endothelial Growth Factor A)
0 (Organophosphonates)

Date Created: 20221211 Date Completed: 20221216 Latest Revision: 20240924

20240924

PMC9738469

10.3390/molecules27238131

36500224