Zinc(II) complexes bearing N,N,S ligands: Synthesis, crystal structure, spectroscopic analysis, molecular docking and biological investigations about its antifungal activity

Souza, Rafael Aparecido Carvalho; Cunha, Vito Labruna; Souza, Jonathan Henrique de; Martins, Carlos Henrique Gomes; Franca, Eduardo de Faria; Pivatto, Marcos; Ellena, Javier; Faustino, Leandro A.; Patrocínio, Antônio Otávio de Toledo; Deflon, Victor M.; Maia, Pedro Ivo da Silva; Oliveira, Carolina Gonçalves

doi:10.1016/j.jinorgbio.2022.111995

Cited by 16 publications

(5 citation statements)

References 58 publications

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“…Because the mechanism results of compound 6r studied above were similar to those of FLC, we speculated that these azole derivatives might operate by inhibition of cytochrome P450, in which the lanosterol 14α-demethylase enzyme (CYP51) is a vital enzyme for sterol biosynthesis of the fungal cell membrane . In this work, compound 6r was theoretically studied to predict the possible binding mode of the structure with the CYP51 enzyme using Discovery Studio 2017R2. , The result was confirmed by a cocrystalline ligand that overlapped with the best conformation after redocking. The three-dimensional crystal structure of C.…”

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confidence: 65%

“…17 In this work, compound 6r was theoretically studied to predict the possible binding mode of the structure with the CYP51 enzyme using Discovery Studio 2017R2. 18,19 The result was confirmed by a cocrystalline ligand that overlapped with the best conformation after redocking. The three-dimensional crystal structure of C. albicans CYP51 enzymes complexed with itraconazole (PDB code 5V5Z), which was downloaded from the Protein Data Bank (http://www.rcsb.org), was used in the molecular docking study.…”

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confidence: 71%

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Synthesis and Antifungal Evaluation of New Azole Derivatives against Candida albicans

Hu,

Xu,

Huang

et al. 2023

ACS Med. Chem. Lett.

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In this study, we designed and prepared a series of new azole derivatives by recombination of fluconazole (FLC) and ketoconazole units, and in vitro antifungal activities against Candida albicans were evaluated. The results indicated that most azoles showed good antifungal activity against the drug-sensitive C. albicans strain, especially compounds 6a, 6e, 6n, 6p, 6r, 6s, 6t, and 6v, which displayed better antifungal activity (MIC50 < 1.0 μg/mL) than FLC against SC5314. The further mechanism study showed that compound 6r could significantly inhibit the formation of C. albicans biofilm, increase the permeability of the cell membrane, reduce the ergosterol level of the cell membrane, damage the membrane structure, and destroy the integrity of the cell structure to exert excellent antifungal activity. Subsequently, a molecular docking study indicated that azole compounds could inhibit cytochrome P450 14α-demethylase (CYP51). Therefore, these azole derivatives can be considered as potent antifungal drugs to treat fungal infections.

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confidence: 65%

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confidence: 71%

Synthesis and Antifungal Evaluation of New Azole Derivatives against Candida albicans

Hu,

Xu,

Huang

et al. 2023

ACS Med. Chem. Lett.

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“…Souza and co-workers analyzed a family of zinc(II) complexes bearing polydentate-N,N,S ligands against the CYP51 enzyme. The calculations revealed that one complex displayed a docking score of -11.12 kcal/mol, mainly due to hydrogen bonds with Tyr118 and Hem601 and confirmation of its considerable antifungal activity [66]. The interactions of complexes 6-10 were investigated by the molecular docking method, and the results were compared to those of Fluconazole (Table 4).…”

Section: Candida Albicansmentioning

confidence: 99%

Benzimidazol-2-ylidene Silver Complexes: Synthesis, Characterization, Antimicrobial and Antibiofilm Activities, Molecular Docking and Theoretical Investigations

Tutar,

Çelik,

Üstün

et al. 2023

Inorganics

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Five silver(I) complexes, namely chloro[1-methallyl-3-benzyl)benzimidazol-2-ylidene] silver (6), chloro[1-methallyl-3-(2,3,5,6-tetramethylbenzyl)benzimidazol-2-ylidene]silver (7), chloro[1-methallyl-3-(3,4,5-trimethoxylbenzyl)benzimidazol-2-ylidene]silver (8), chloro[1-methallyl- 3-(naphthylmethyl)benzimidazol-2-ylidene]silver (9), and chloro [1-methallyl-3-(anthracen-9-yl- methyl)benzimidazol-2-ylidene]silver (10), were prepared starting from their corresponding benzimidazolium salts and silver oxide in 71–81% yields. A single-crystal X-ray structure of 7 was determined. These five Ag-NHC complexes were evaluated for their antimicrobial and biofilm formation inhibition properties. Complex 10 exhibited high antimicrobial activities comparable to those obtained with standard drugs such as Fluconazole in contact with Staphylococcus aureus, Enterococcus faecalis, Escherichia coli, Acinetobacter baumannii, and Candida albicans. The latter complex has been shown to be very efficient in antibiofilm activity, with 92.9% biofilm inhibition at 1.9 μg/mL on Escherichia coli. Additionally, the molecules were optimized with DFT-based computational methods for obtaining insight into the structure/reactivity relations through the relative energies of the frontier orbitals. The optimized molecules were also analyzed by molecular docking method against DNA gyrase of Escherichia coli and CYP51 from Candida albicans.

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“…In this sense, thiosemicarbazone ligands and many of their complexes have been tested as antitumor agents, some compounds reaching phases I-III of clinical trials [11,12]. They have also been tested as antibacterial [13][14][15] and antifungal [16,17] therapeutics, among many other pathologies. All these studies make clear the need to know in depth the biochemical targets of thiosemicarbazone complexes, or the transformations that they may experience in physiological media.…”

Section: Introductionmentioning

confidence: 99%

Exploring the Biological Properties of Zn(II) Bisthiosemicarbazone Helicates

Fernández-Fariña

Velo-Heleno

Carballido

et al. 2023

IJMS

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The design of artificial helicoidal molecules derived from metal ions with biological properties is one of the objectives within metallosupramolecular chemistry. Herein, we report three zinc helicates derived from a family of bisthiosemicarbazone ligands with different terminal groups, Zn2(LMe)2∙2H2O 1, Zn2(LPh)2∙2H2O 2 and Zn2(LPhNO2)23, obtained by an electrochemical methodology. These helicates have been fully characterized by different techniques, including X-ray diffraction. Biological studies of the zinc(II) helicates such as toxicity assays with erythrocytes and interaction studies with proteins and oligonucleotides were performed, demonstrating in all cases low toxicity and an absence of covalent interaction with the proteins and oligonucleotides. The in vitro cytotoxicity of the helicates was tested against MCF-7 (human breast carcinoma), A2780 (human ovarian carcinoma cells), NCI-H460 (human lung carcinoma cells) and MRC-5 (normal human lung fibroblasts), comparing the IC50 values with cisplatin. We will try to demonstrate if the terminal substituent of the ligand precursor exerts any effect in toxicity or in the antitumor activity of the zinc helicates.

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Zinc(II) complexes bearing N,N,S ligands: Synthesis, crystal structure, spectroscopic analysis, molecular docking and biological investigations about its antifungal activity

Cited by 16 publications

References 58 publications

Synthesis and Antifungal Evaluation of New Azole Derivatives against Candida albicans

Synthesis and Antifungal Evaluation of New Azole Derivatives against Candida albicans

Benzimidazol-2-ylidene Silver Complexes: Synthesis, Characterization, Antimicrobial and Antibiofilm Activities, Molecular Docking and Theoretical Investigations

Exploring the Biological Properties of Zn(II) Bisthiosemicarbazone Helicates

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