Copper-Coordinated Thiazoles and Benzothiazoles: A Perfect Alliance in the Search for Compounds with Antibacterial and Antifungal Activity

Colorado‐Peralta, Raúl; Olivares‐Romero, José Luis; Rosete-Luna, Sharon; García-Barradas, Óscar; Reyes‐Márquez, Viviana; Hernández-Romero, Delia; Morales‐Morales, David

doi:10.3390/inorganics11050185

Cited by 6 publications

(6 citation statements)

References 117 publications

(147 reference statements)

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“…The variations in the activity of the metal complexes against different strains are contingent upon factors such as penetrability and potential differences in the ribosomes of microbial cells. These differences are also influenced by the geometry and types of groups linked to the metal ion 50 . The ineffectiveness of certain compounds against particular strains is attributed to either the functioning of efflux pumps or the obstacles posed by these microbes 50 .…”

Section: Resultsmentioning

confidence: 99%

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Synthesis, characterization, biological potency, and molecular docking of Co2+, Ni2+ and Cu2+ complexes of a benzoyl isothiocyanate based ligand

Al-Farraj,

Younis,

El-Reash

2024

Sci Rep

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The primary objective of the present study was to produce metal complexes of H4DAP ligand (N,N'-((pyridine-2,6-diylbis(azanediyl))bis(carbonothioyl))dibenzamide) derived from 2,6-diaminopyridine and benzoyl isothiocyanate with either ML or M2L stoichiometry. There are three distinct coordination complexes obtained with the formulas [Co(H2DAP)]·H2O, [Ni2(H2DAP)Cl2(H2O)2]·H2O, and [Cu(H4DAP)Cl2]·3H2O. The confirmation of the structures of all derivatives was achieved through the utilization of several analytical techniques, including FT-IR, UV–Vis, NMR, GC–MS, PXRD, SEM, TEM analysis, and QM calculations. Aiming to analyze various noncovalent interactions, topological methods such as QTAIM, NCI, ELF, and LOL were performed. Furthermore, the capacity of metal–ligand binding was examined by fluorescence emission spectroscopy. An in vitro investigation showed that the viability of MDA-MB-231 and HepG-2 cells was lower when exposed to the manufactured Cu2+ complex, in comparison to the normal cis-platin medication. The compounds were further evaluated for their in vitro antibacterial activity. The Ni2+ complex has shown promising activity against all tested pathogens, comparable to the reference drugs Gentamycin and Ketoconazole. Furthermore, a computational docking investigation was conducted to further examine the orientation, interaction, and conformation of the recently created compounds on the active site of the Bcl-2 protein.

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Section: Resultsmentioning

confidence: 99%

“…These differences are also influenced by the geometry and types of groups linked to the metal ion 50 . The ineffectiveness of certain compounds against particular strains is attributed to either the functioning of efflux pumps or the obstacles posed by these microbes 50 .…”

Section: Resultsmentioning

confidence: 99%

Synthesis, characterization, biological potency, and molecular docking of Co2+, Ni2+ and Cu2+ complexes of a benzoyl isothiocyanate based ligand

Al-Farraj,

Younis,

El-Reash

2024

Sci Rep

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“…Another group of gramine derivatives contained indole moieties attached by a methylene linker at the C3 position to azoles or benzazoles. Azole-based compounds are essential building blocks in many pharmaceutical agents, and they have various effects, including antimicrobial properties [25][26][27][28][29]. Their activities are explained by the existence of a tautomeric equilibrium.…”

Section: Introductionmentioning

confidence: 99%

Novel C3-Methylene-Bridged Indole Derivatives with and without Substituents at N1: The Influence of Substituents on Their Hemolytic, Cytoprotective, and Antimicrobial Activity

Babijczuk,

Berdzik,

Nowak

et al. 2024

IJMS

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Alkaloids are natural compounds useful as scaffolds for discovering new bioactive molecules. This study utilized alkaloid gramine to synthesize two groups of C3-substituted indole derivatives, which were either functionalized at N1 or not. The compounds were characterized by spectroscopic methods. The protective effects of the new compounds against in vitro oxidative hemolysis induced by standard oxidant 2,2′-azobis(2-amidinopropane dihydro chloride (AAPH) on human erythrocytes as a cell model were investigated. Additionally, the compounds were screened for antimicrobial activity. The results indicated that most of the indole derivatives devoid of the N1 substitution exhibited strong cytoprotective properties. The docking studies supported the affinities of selected indole-based ligands as potential antioxidants. Furthermore, the derivatives obtained exhibited potent fungicidal properties. The structures of the eight derivatives possessing indole moiety bridged to the imidazole-, benzimidazole-, thiazole-, benzothiazole-, and 5-methylbenzothiazoline-2-thiones were determined by X-ray diffraction. The C=S bond lengths in the thioamide fragment pointed to the involvement of zwitterionic structures of varying contribution. The predominance of zwitterionic mesomers may explain the lack of cytoprotective properties, while steric effects, which limit multiple the hydrogen-bond acceptor properties of a thione sulfur, seem to be responsible for the high hemolytic activity.

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“…Advances in this field have been carefully reviewed in recent papers and books [ 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 ]. On the other hand, a few highly effective antibacterial low-toxicity compounds have been obtained based on the fused heterocyclic benzothiazole system [ 38 , 39 , 40 , 41 , 42 ]. These findings inspired us to synthesize benzothiazole derivatives of chitosan and study their antibacterial properties in the framework of our current work in the hope that the summation of the antibacterial effects of both chitosan and benzothiazole pharmacophore results in an increased antibacterial activity of the resulting polymers.…”

Section: Introductionmentioning

confidence: 99%

Benzothiazole Derivatives of Chitosan and Their Derived Nanoparticles: Synthesis and In Vitro and In Vivo Antibacterial Effects

Shakola,

Rubanik,

Rubanik

et al. 2023

Polymers

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In this work, we focused on synthesizing and assessing novel chitosan-based antibacterial polymers and their nanoparticles by incorporating benzothiazole substituents. The growing resistance to antibiotics has necessitated the search for alternative antimicrobial compounds. This study aimed to synthesize and evaluate chitosan-based polymers and nanoparticles with benzothiazole substituents for their antibacterial properties and toxicity. The benzothiazole derivatives of chitosan and their nanoparticles were synthesized through electrochemical coupling. The in vivo antibacterial efficacy was tested on white rats with induced peritonitis using a microbial suspension containing S. aureus and E. coli. Additionally, in vitro and in vivo toxicity assessments were conducted. The chitosan-based antibacterial systems showed significant in vivo antibacterial activity, surpassing that of unmodified chitosan and commercial antibiotics. Moreover, the toxicity studies revealed low toxicity levels of the synthesized derivatives, which did not differ significantly from native chitosan. The synthesized chitosan-based polymers and nanoparticles demonstrated potent antibacterial activity and low toxicity, highlighting their potential as effective alternatives to traditional antibiotics. Further investigations in pharmacology and preclinical trials are recommended to explore their application in clinical settings.

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Copper-Coordinated Thiazoles and Benzothiazoles: A Perfect Alliance in the Search for Compounds with Antibacterial and Antifungal Activity

Cited by 6 publications

References 117 publications

Synthesis, characterization, biological potency, and molecular docking of Co2+, Ni2+ and Cu2+ complexes of a benzoyl isothiocyanate based ligand

Synthesis, characterization, biological potency, and molecular docking of Co2+, Ni2+ and Cu2+ complexes of a benzoyl isothiocyanate based ligand

Novel C3-Methylene-Bridged Indole Derivatives with and without Substituents at N1: The Influence of Substituents on Their Hemolytic, Cytoprotective, and Antimicrobial Activity

Benzothiazole Derivatives of Chitosan and Their Derived Nanoparticles: Synthesis and In Vitro and In Vivo Antibacterial Effects

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