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    Novel derivatives of the antibiotic NHC–Ag(I) drug candidate SBC3: Synthesis, biological evaluation and 109Ag NMR studies


    O'Beirne, Cillian and Althani, Hessah T. and Dada, Oyinlola and Cassidy, Jennifer and Kavanagh, Kevin and Müller-Bunz, Helge and Ortin, Yannick and Zhu, Xiangming and Tacke, Matthias (2018) Novel derivatives of the antibiotic NHC–Ag(I) drug candidate SBC3: Synthesis, biological evaluation and 109Ag NMR studies. Polyhedron, 149. pp. 95-103. ISSN 0277-5387

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    Abstract

    The synthesis of six novel N-heterocyclic carbene silver(I) acetate complexes, three symmetrical and three non-symmetrical, were achieved using 4,5-diphenylimidazole to produce intermediate imidazolium salts and then obtain the corresponding silver(I) complexes through complexation with silver acetate via the Youngs’ method. In vitro biological testing, using the Kirby–Bauer disk diffusion method, was conducted against Methicillin-resistant Staphylococcus aureus (MRSA) and Escherichia coli, with a NHC–silver(I) acetate compound, SBC3, and Tetracycline as standards. Silver(I) acetate complex 7 resulted in a 4 mm clearance against MRSA, showing the highest antibiotic activity of the novel derivatives. Crystallographic data revealed similar bond lengths and angles to previously reported NHC–silver(I) acetate complexes, with complex 8 showing interesting η2-coordination between the silver atom and acetate oxygens. 109Ag NMR studies were conducted, highlighting the effects of the substituents of the imidazole ring on the silver atom shown by the corresponding shifts in the 109Ag NMR spectra. The incorporation of isopropyl groups to several of the novel complexes resulted in larger upfield 109Ag NMR shift values compared to all other substituents.

    Item Type: Article
    Keywords: NHC–silver(I) acetate complexes; MRSA; Antibiotic resistance; 109Ag NMR; XRD structures;
    Academic Unit: Faculty of Science and Engineering > Biology
    Item ID: 12438
    Identification Number: https://doi.org/10.1016/j.poly.2018.04.017
    Depositing User: Dr. Kevin Kavanagh
    Date Deposited: 17 Feb 2020 16:51
    Journal or Publication Title: Polyhedron
    Publisher: Elsevier
    Refereed: Yes
    URI:

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