Copper(II) species with 1‐(o‐tolyl)biguanide: Structural characterization, ROS scavenging, antibacterial activity, biocompatibility and in silico studies

The species cis‐[Cu(tbg)2](ClO4)2 (CuTP) (tbg: 1‐(o‐tolyl)biguanide) was designed as a novel antimicrobial and biocompatible agent. The single‐crystal X‐ray diffraction revealed a mononuclear species with a very interesting structure consisting of two tautomeric forms of tbg arranged in a cis‐config...

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Bibliographic Details
Published in:Applied organometallic chemistry 2022-01, Vol.36 (1), p.n/a
Main Authors: Maxim, Catalin, Badea, Mihaela, Rostas, Arpad Mihai, Chifiriuc, Mariana Carmen, Pircalabioru, Gratiela Gradisteanu, Avram, Speranța, Olar, Rodica
Format: Article
Language:English
Subjects:
antibacterial activity
Antimicrobial agents
biguanide complex
Biocompatibility
biofilm
Biofilms
Chemistry
Copper
Enterobacter cloacae
Fibroblasts
Hydrogen bonds
Hydroxyl radicals
in silico
Infectious diseases
Klebsiella
Scavenging
Structural analysis
structure
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Summary:The species cis‐[Cu(tbg)2](ClO4)2 (CuTP) (tbg: 1‐(o‐tolyl)biguanide) was designed as a novel antimicrobial and biocompatible agent. The single‐crystal X‐ray diffraction revealed a mononuclear species with a very interesting structure consisting of two tautomeric forms of tbg arranged in a cis‐configuration. A complex hydrogen bond network with perchlorate anions involved in different interactions leads to a supramolecular structure. The EPR data indicated the formation of a stable cis‐trans mixture in dimethylsulfoxide. Moreover, the EPR experiments evidenced no activity against the superoxide radical (O2·−) but scavenging ability of the hydroxyl radical (HO·). This complex exhibited excellent antibacterial properties against planktonic and biofilm embedded gram‐negative (Klebsiella pneumoniae, Enterobacter cloacae) and gram‐positive (Bacillus subtilis, Lysteria monocytogenes) bacteria. The best efficiency was noticed against E. cloacae and L. monocytogenes with minimal inhibitory concentration and minimal biofilm eradication for a concentration value of 1.95 μg/ml. One of the possible mechanisms of antimicrobial activity is represented by reactive oxygen species (ROS) generation. The complex was not cytotoxic on L929 fibroblasts. The in silico analysis confirmed the drug‐likeness and safety profile of the tested compound and its potential for developing novel antimicrobial and therapeutic tools, targeting other clinical conditions besides infectious diseases.
ISSN:0268-2605
1099-0739
DOI:10.1002/aoc.6471