title: Effects of different substituents on the crystal structures and antimicrobial activities of six Ag(I) quinoline compounds.
abstract: The syntheses and single crystal X-ray structures of [Ag(5-nitroquinoline)2]NO3 (1), [Ag(8-nitroquinoline)2]NO3·H2O (2), [Ag(6-methoxy-8-nitroquinoline)(NO3)]n (3), [Ag(3-quinolinecarbonitrile)(NO3)]n (4), [Ag(3-quinolinecarbonitrile)2]NO3 (5), and [Ag(6-quinolinecarboxylic acid)2]NO3 (6) are described. As an alternative to solution chemistry, solid-state grinding could be used to prepare compounds 1 and 3, but the preparation of 4 and 5 in this way failed. The Ag(I) ions in the monomeric compounds 1, 2, 5, and 6 are coordinated to two ligands via the nitrogen atoms of the quinoline rings, thereby forming a distorted linear coordination geometry with Ag-N bond distances of 2.142(2)-2.336(2) Å and N-Ag-N bond angles of 163.62(13)°-172.25(13)°. The 1D coordination polymers 3 and 4 contain Ag(I) centers coordinating one ligand and two bridging nitrate groups, thereby forming a distorted trigonal planar coordination geometry with Ag-N bond distances of 2.2700(14) and 2.224(5) Å, Ag-O bond distances of 2.261(4)-2.536(5) Å, and N-Ag-O bond angles of 115.23(5)°-155.56(5)°. Hirshfeld surface analyses of compounds 1-6 are presented as d(norm) and curvedness maps. The d(norm) maps show different interaction sites around the Ag(I) ions, i.e., Ag···Ag interactions and possible O-H···O, C-H···O, C-H···N, and C-H···C hydrogen bonds. Curvedness maps are a good way of visualizing π-π stacking interactions between molecules. The antimicrobial activities of compounds 1, 2, and 6 were screened against 15 different multidrug-resistant strains of bacteria isolated from diabetic foot ulcers and compared to the antimicrobial activities of the clinically used silver sulfadiazine (SS). Compound 2 showed activity similar to SS against this set of test organisms, being active against all strains and having slightly better average silver efficiency than SS (5 vs 6 μg Ag/mL). Against the standard nonresistant bacterial strains of Staphylococcus aureus , Pseudomonas aeruginosa , Proteus mirabilis , and Streptococcus pyogenes , compound 1 performed better than silver nitrate, with an average MIC of 6 μg Ag/mL versus 18 μg Ag/mL for the reference AgNO3. Electrospray ionization mass spectrometry (ESI-MS) analyses of compounds 3 and 6 in DMSO/MeOH confirm the two-coordinated Ag(+) complexes in solution, and the results of the (1)H NMR titrations of DMSO solutions of 5-nitroquinoline and 8-nitroquinoline with AgNO3 in DMSO suggest that 5-nitroquinoline is more strongly coordinated to the silver ion.
authors: Department of Chemical and Biological Engineering, Chalmers University of Technology, SE-412 96 Gothenburg, Sweden. shimo_chem@hotmail.com
authors: Alshima'a A
authors: AA
authors: Massoud
authors: Vratislav
authors: V
authors: Langer
authors: Yousry M
authors: YM
authors: Gohar
authors: Morsy A M
authors: MA
authors: Abu-Youssef
authors: Janne
authors: J
authors: Jänis
authors: Gabriella
authors: G
authors: Lindberg
authors: Karl
authors: K
authors: Hansson
authors: Lars
authors: L
authors: Öhrström
mesh_terms: D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D056831:Coordination Complexes / Q000138:chemical synthesis* / Q000494:pharmacology; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D008024:Ligands; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D011513:Proteus mirabilis / Q000187:drug effects / Q000254:growth & development; D011550:Pseudomonas aeruginosa / Q000187:drug effects / Q000254:growth & development; D011804:Quinolines / Q000737:chemistry*; D012834:Silver / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D013211:Staphylococcus aureus / Q000187:drug effects / Q000254:growth & development; D013297:Streptococcus pyogenes / Q000187:drug effects / Q000254:growth & development; D013329:Structure-Activity Relationship
chemical_list: D000890:Anti-Infective Agents; D056831:Coordination Complexes; D008024:Ligands; D011804:Quinolines; D012834:Silver