Synthesis, crystallographic studies, molecular modeling and in vitro biological studies of silver(I) complexes with aminoadamantane ligands

Author(s)

dos Santos Pereira, Anna Karla ^[1] ; Nakahata, Douglas Hideki ^[1] ; Manzano, Carlos Marrote ^[1] ; Simoni, Deborah de Alencar ^[1] ; Pereira, Douglas Henrique ^[2] ; Lustri, Wilton Rogerio ^[3] ; Barboza Formiga, Andre Luiz ^[1] ; Corbi, Pedro Paulo ^[1]

Affiliation

^[1] Univ Campinas UNICAMP, Inst Chem, POB 6154, BR-13083970 Campinas, SP - Brazil

^[2] Fed Univ Tocantins, Chem Coll, Campus Gurupi, POB 66, BR-77402970 Gurupi - Brazil

^[3] Univ Araraquara, UNIARA, Dept Biol & Hlth Sci, BR-14801320 Sao Paulo, SP - Brazil

• Document type: Journal article
• Source: Polyhedron; v. 173, NOV 15 2019.
• Web of Science Citations: 1

Abstract

Silver(I) complexes with amantadine (atd) and memantine (mtn) were synthesized and characterized. Elemental, thermogravimetric and mass spectrometric analyses indicated a 1:2 metal/ligand ratio, with the molecular composition AgC20H34N2 center dot NO3 for Ag-atd and AgC24H42N2 center dot NO3 center dot H2O for Ag-mtn. The crystal structures of the silver(I) complexes were determined by single crystal X-ray diffractometric studies and show the coordination of amantadine and memantine to the Ag(I) ion by the nitrogen atom of the NH2 group. The spectral analysis by infrared and H-1, C-13 and [N-15, H-1] nuclear magnetic resonance (NMR) spectroscopies confirmed the coordination sites of the ligands to the silver ions. Computational studies revealed modes of vibration and bond lengths similar to those found experimentally. The in vitro antibacterial activity assays showed that amantadine is not active over the tested strains while memantine showed a low activity against Staphylococcus aureus and Pseudomonas aeruginosa. On the other hand, the complexes had a pronounced antibacterial activity over the same strains with minimum inhibitory concentration (MIC) values in the micromolar range. Biophysical assays based on fluorescence spectroscopy indicated that the silver(I) complexes interact weakly with bovine serum albumin, while agarose gel electrophoresis and competitive binding experiments revealed that the compounds interact with DNA by non-covalent interactions. (C) 2019 Elsevier Ltd. All rights reserved. (AU)

• FAPESP's process: 15/20882-3 - Metal complexes of sulfamethoxydiazine and sulfadimethoxine: synthesis, characterization and applications as antimicrobial agents for topical use
• Grantee: Douglas Hideki Nakahata
• Support Opportunities: Scholarships in Brazil - Doctorate
• FAPESP's process: 14/50906-9 - INCT 2014: in Functional Complex Materials
• Grantee: Fernando Galembeck
• Support Opportunities: Research Projects - Thematic Grants
• FAPESP's process: 18/12062-4 - Synthesis, characterization and studies of interaction with biomolecules of metal complexes containing biologically active ligands: a strategy in the preparation of new agents with antibacterial and antiviral activities
• Grantee: Pedro Paulo Corbi
• Support Opportunities: Regular Research Grants
• FAPESP's process: 13/22127-2 - Development of novel materials strategic for integrated analytical devices
• Grantee: Lauro Tatsuo Kubota
• Support Opportunities: Research Projects - Thematic Grants
• FAPESP's process: 17/25995-6 - New Ag(I), Pd(II) and Pt(II) metal complexes with ligands used for the treatment of Tuberculosis: synthesis and in vitro evaluation of antimicrobial and antiproliferative activities
• Grantee: Carlos Marrote Manzano
• Support Opportunities: Scholarships in Brazil - Doctorate
• FAPESP's process: 18/12590-0 - Synthesis of metal complexes with bioactive N,N or N,O-coordinating ligands for use in sustainable delivery system based on bacterial cellulose
• Grantee: Wilton Rogério Lustri
• Support Opportunities: Regular Research Grants