title: Silver(I) compounds of the anti-inflammatory agents salicylic acid and p-hydroxyl-benzoic acid which modulate cell function.
abstract: Silver nitrate reacts with salicylic acid (salH2) or p-hydroxy-benzoic acid (p-HbzaH2) and equimolar amount of NaOH to yield a white precipitations which are then treated with tri(p-tolyl)phosphine (tptp) or tri(m-tolyl)phosphine (tmtp) to yield the complexes [Ag(tptp)2(salH)] (1), [Ag(tptp)2(p-Hbza)] (2) and [Ag(tmtp)2(salH)] (3). Complexes 1 and 3 are also obtained when aspirin (aspH) is used. The acetic ester of salicylic acid is hydrolyzed to form the complexes 1 and 3. However, when aspirin and tptp are used, a mixture of products was obtained which contains both 1 and an ionic complex of formula {[Ag(tptp)4](+)[(salH)(-)]∙[(CH3)2NCHO)]∙(H2O)} (1a). The complexes were characterized by m.p., e.a., mid-FT-IR, (1)H-,(31)P-NMR, HRMS, UV-vis spectroscopic techniques and X-ray crystallography. Two phosphorus and one carboxylic oxygen atoms form a trigonal planar geometry around Ag(I) ions in complexes 1-3. Complex 1a consists of a [Ag(tptp)4](+) cation and a deprotonated salH(-) counter anion. The influence of 1-3 on the viability of MCF-7 (breast) and HeLa (cervix) adenocarcinoma cells, is evaluated. DNA binding tests indicate the ability of 1-3 to modify the activity of cells. The binding constants of 1-3 towards calf-thymus DNA, reveal stronger interaction of 2. Changes in fluorescent emission light of ethidium bromide (EB) in the presence of DNA suggest intercalation or electrostatic interactions into DNA for 1 and 3. Docking studies on DNA-complex interactions confirm the binding of 1-3 in the minor groove of B-DNA. Moreover, the influence of 1-3 on the peroxidation of linoleic acid to hydroperoxylinoleic acid by the enzyme lipoxygenase (LOX) was kinetically and theoretically studied.
authors.affiliation: Section of Inorganic and Analytical Chemistry, Department of Chemistry, University of Ioannina, 45110 Ioannina, Greece.
authors.forename: C N
authors.initials: CN
authors.lastname: Banti
authors.affiliation: Section of Inorganic and Analytical Chemistry, Department of Chemistry, University of Ioannina, 45110 Ioannina, Greece.
authors.forename: A D
authors.initials: AD
authors.lastname: Giannoulis
authors.affiliation: Medical Physics Laboratory, Medical School, University of Ioannina, 45110 Ioannina, Greece. Electronic address: nkourkou@uoi.gr.
authors.forename: N
authors.initials: N
authors.lastname: Kourkoumelis
authors.affiliation: Department of Chemistry, Adam Mickiewicz University, Umultowska 89b, 61-614 Poznań, Poland.
authors.forename: A M
authors.initials: AM
authors.lastname: Owczarzak
authors.affiliation: Department of Chemistry, Adam Mickiewicz University, Umultowska 89b, 61-614 Poznań, Poland. Electronic address: mkubicki@amu.edu.pl.
authors.forename: M
authors.initials: M
authors.lastname: Kubicki
authors.affiliation: Section of Inorganic and Analytical Chemistry, Department of Chemistry, University of Ioannina, 45110 Ioannina, Greece. Electronic address: shadjika@uoi.gr.
authors.forename: S K
authors.initials: SK
authors.lastname: Hadjikakou
mesh_terms: D000818:Animals; D001565:Benzoates / Q000737:chemistry / Q000494:pharmacology; D002417:Cattle; D002470:Cell Survival / Q000187:drug effects; D056831:Coordination Complexes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D004247:DNA / Q000737:chemistry*; D006367:HeLa Cells; D006801:Humans; D061986:MCF-7 Cells; D062105:Molecular Docking Simulation; D020156:Salicylic Acid / Q000737:chemistry / Q000494:pharmacology; D012834:Silver / Q000737:chemistry / Q000494:pharmacology
chemical_list: D001565:Benzoates; D056831:Coordination Complexes; D012834:Silver; D004247:DNA; C427203:calf thymus DNA; D020156:Salicylic Acid
keywords: Cell studies; DNA and lipoxygenase; Molecular docking; Silver(I) complexes; X-ray structure