Synthesis, crystal structure, quantum chemical calculations, DNA interactions, and antimicrobial activity of [Ag(2-amino-3-methylpyridine)(2)]NO(3) and [Ag(pyridine-2-carboxaldoxime)NO(3)]

• Published in: Inorganic chemistry Vol. 49; no. 21; pp. 9788 - 9797
• Main Authors: Abu-Youssef, Morsy A M, Soliman, Saied M, Langer, Vratislav, Gohar, Yousry M, Hasanen, Ahmed A, Makhyoun, Mohamed A, Zaky, Amira H, Öhrström, Lars R
• Format: Journal Article
• Language: English
• Published: United States 01.11.2010
• Subjects: Anti-Infective Agents - chemical synthesis; Anti-Infective Agents - chemistry; Anti-Infective Agents - pharmacology; Crystallography, X-Ray; DNA - chemistry; Microbial Sensitivity Tests; Models, Molecular; Molecular Structure; Organometallic Compounds - chemical synthesis; Organometallic Compounds - chemistry; Organometallic Compounds - pharmacology; Quantum Theory; Temperature; Vibration
• ISSN: 1520-510X
• DOI: 10.1021/ic100581k

[Ag(2-amino-3-methylpyridine)(2)]NO(3) (1) and [Ag(pyridine-2-carboxaldoxime)NO(3)] (2) were prepared from corresponding ligands and AgNO(3) in water/ethanol solutions, and the products were characterized by IR, elemental analysis, NMR, and TGA. The X-ray crystal structures of the two compounds show that the geometry around the silver(I) ion is bent for complex 1 with nitrate as an anion and trigonal planar for complex 2 with nitrate coordinated. ESI-MS results of solutions of 2 indicate the independent existence in solution of the [Ag(pyridine-2-carboxaldoxime)](+) ion. The geometries of the complexes are well described by DFT calculations using the ZORA relativistic approach. The compounds were tested against 14 different clinically isolated and four ATCC standard bacteria and yeasts and also compared with 17 commonly used antibiotics. Both 1 and 2 exhibited considerable activity against S. lutea , M. lutea , and S. aureus and against the yeast Candida albicans , while 2-amino-3-methylpyridine is slightly active and pyridine-2-carboxaldoxime shows no antimicrobial activity. In addition, the interaction of these metal complexes with DNA was investigated. Both 1 and 2 bind to DNA and reduce its electrophoretic mobility with different patterns of migration, while the ligands themselves induce no change.