Antibacterial activity of transition metal complexes containing a tridentate NNO phenoxymethylpenicillin-based Schiff base. An anti-MRSA iron (II) complex

Juan Roberto Anacona, Karen Ruiz, Marcos Loroño, Freddy Celis

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4 Scopus citations

Abstract

Transition metal complexes containing a phenoxymethylpenicillin-derived Schiff base (HL) 3 obtained from the condensation of phenoxymethylpenicillin (PMP) 1, with 1,2-diaminobenzene 2, were prepared. Spectroscopic and physicochemical techniques, namely, UV–Vis, FT-IR, 1 H-NMR, EPR, mass spectrometry, magnetic susceptibility, molar conductance, DFT studies, together with elemental and thermal analyses were used to characterize the synthesized complexes. Based on the characterization studies, the general formulae [ML (OAc)(H 2 O) 2 ] where M = Fe 4, Co 5, Ni 6, Cu 7, and Zn 8, were proposed for the complexes. The Schiff base ligand 3 behaved as a monoanionic tridentate NNO chelating agent. On the basis of magnetic and spectral data an octahedral geometry for all the complexes was suggested. Schiff base ligand 3, and the metal complexes 4–8 were tested against G(+) or bactericidal activity by agar disc diffusion method and minimal inhibitory concentration (MIC). The results were compared with the activity of the standard drug PMP 1. In vitro bacterial viability revealed that 3 had similar activity than 1 and exhibited modification in its bactericidal activity when formed metal complexes. It was found that the complexes 4, 6 and 7 exhibited much better bactericidal activity than 1 against methicillin-resistant Staphilococcus Aureus (MRSA) being complex 4 the most promising compound showing a MIC value of 0.042 μmol/ml.

Original languageEnglish
Article numbere4744
JournalApplied Organometallic Chemistry
Volume33
Issue number4
DOIs
StatePublished - Apr 2019

Bibliographical note

Funding Information:
The authors gratefully acknowledge to the Universidad de Oriente and the Universidad de Playa Ancha for their support.

Publisher Copyright:
© 2019 John Wiley & Sons, Ltd.

Copyright:
Copyright 2019 Elsevier B.V., All rights reserved.

Keywords

  • Schiff base
  • antibacterial activity
  • phenoxymethylpenicillin-based Schiff base metal complexes
  • transition metal complexes

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