ABSTRACT
Redox-active azothioformamides (ATFs) contain an NNCS 1,3-heterodiene motif typically found in other molecular subclasses that exhibit a wide range of cytotoxic and anti-neoplastic effects, either alone or as chelation complexes with various metals. For this study, a small library of ATF compounds was synthesized and tested across a range of microbes, fungi, and cancer cell lines for biological activity, both alone and as metal chelates of copper(I) and silver(I) salts. Alone, the ATF compounds exhibited little antimicrobial activity, but all inhibited the cell growth of A549 lung carcinoma cells (IC50 values of 1-6 µM). As copper(I) and silver(I) coordination complexes, several of the ATFs showed antimicrobial activity against gram positive Staphylococcus aureus and Bacillus subtilis cells (IC50 â¼ 5-20 µM) and the fungi Candida albicans (IC50 â¼ 8-12 µM); as well as cytotoxicity against both lung carcinoma A549 cells and lymphoblastic leukemia K562 cells.
Subject(s)
Anti-Infective Agents , Antineoplastic Agents , Carcinoma , Coordination Complexes , Humans , Copper/pharmacology , Anti-Infective Agents/pharmacology , Anti-Infective Agents/metabolism , Silver/pharmacology , Cell Line , Coordination Complexes/pharmacology , Chelating Agents/pharmacology , Fungi , Microbial Sensitivity Tests , Antineoplastic Agents/pharmacology , Anti-Bacterial Agents/pharmacologyABSTRACT
The structure of the title complex, [Ag(C11H15N3S)2]PF6, has monoclinic (P21/c) symmetry, and the silver atom has a distorted square-planar geometry. The coordination complex crystallized from mixing silver hexa-fluorido-phosphate with a concentrated tetra-hydro-furan solution of N,N-di-ethyl-phenyl-azo-thio-formamide [ATF; systematic name: 3,3-diethyl-1-(phenyl-imino)-thio-urea] under ambient conditions. The resultant coordination complex exhibits a 2:1 ligand-to-metal ratio, with the silver(I) atom having a fourfold AgN2S2 coordination sphere, with a single PF6 counter-ion. In the crystal, however, one sulfur atom from an ATF ligand of a neighboring complex coordinates to the silver atom, with a bond distance of 2.9884â (14)â Å. This creates a polymeric zigzag chain propagating along the c-axis direction. The chains are linked by C-Hâ¯F hydrogen bonds, forming slabs parallel to the ac plane.
