Promising fluconazole based zinc(II) and copper(II) coordination polymers against Chagas disease

Azevedo-França, José Aleixo de; Barrias, Emile; Franco, Chris H. J.; Villarreal, Wilmer; Vieira, Evanice Menezes Marçal; Ferreira, Ana Maria da Costa; Souza, Wanderley de; Navarro, Maribel

doi:10.1016/j.jinorgbio.2022.111834

Cited by 7 publications

(9 citation statements)

References 34 publications

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“…In this scenario, the use of metal complexes associated with repurposed/novel drugs is a new line of research that is gaining attention, since many of these compounds can be bactericidal, fungicidal, and even present antiparasitic action [ 13 , 14 , 15 , 16 , 17 , 18 ]. In this sense, a previous study from our group showed that two aminopyridine derivatives complexed with Cu 2+ , namely, cis -aquadichloro( N -[4-(hydroxyphenyl)methyl]-2-pyridinemethamino)copper ( 3a ) and its glycosylated ligand cis -dichloro( N -{[4-(2,3,4,6-tetra- O -acetyl-β-D-glucopyranosyloxy)pheny]lmethyl}-2-pyridinemethamino)copper ( 3b ), were effective against the infective form (trypomastigote) of T. cruzi , while non-toxic action was reported for RAW macrophages [ 19 ].…”

Section: Introductionmentioning

confidence: 99%

In Vitro Effects of Aminopyridyl Ligands Complexed to Copper(II) on the Physiology and Interaction Process of Trypanosoma cruzi

et al. 2023

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Chagas disease is derived from the infection by the protozoan Trypanosoma cruzi. In many countries, benznidazole is the only drug approved for clinical use despite several side effects and the emergence of resistant parasite strains. In this context, our group has previously pointed out that two novel aminopyridine derivatives complexed with Cu2+, namely, cis-aquadichloro(N-[4-(hydroxyphenyl)methyl]-2-pyridinemethamino)copper (3a) and its glycosylated ligand cis-dichloro (N-{[4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)pheny]lmethyl}-2-pyridinemethamino)copper (3b), are effective against T. cruzi trypomastigote forms. With this result in mind, the present work aimed to investigate the effects of both compounds on trypomastigotes physiology and on the interaction process with host cells. Apart from loss of plasma membrane integrity, an increased generation of reactive oxygen species (ROS) and decreased mitochondrial metabolism were observed. Pretreatment of trypomastigotes with these metallodrugs inhibited the association index with LLC-MK2 cells in a typical dose-dependent manner. Both compounds showed low toxicity on mammalian cells (CC50 > 100 µM), and the IC50 values calculated for intracellular amastigotes were determined as 14.4 µM for 3a and 27.1 µM for 3b. This set of results demonstrates the potential of these aminopyridines complexed with Cu2+ as promising candidates for further antitrypanosomal drug development.

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Section: Introductionmentioning

confidence: 99%

In Vitro Effects of Aminopyridyl Ligands Complexed to Copper(II) on the Physiology and Interaction Process of Trypanosoma cruzi

et al. 2023

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“…40 Studies show that FCZ complex with silver, zinc and copper shows more effective antifungal activity than fluconazole itself. 27 FCZ-zinc complex shows more antifungal activity against candida krusei and candida parapsilosis. 29,41 The activity of FCZ-copper complex has been confirmed against Candida glabrata and Candida albicans.…”

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confidence: 96%

“…Therefore, the complexation of drugs with metal ions may increase and diversify their medicinal properties. [27][28][29][30][31] In the following, it is better to have a brief overview of drugs and ions that have been used in research. Silver is known as an antiinflammatory, antibacterial and disinfectant agent.…”

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confidence: 99%

“…52 These advantages prompted many researchers to synthesize various complexes of these drugs with cations such as silver, zinc, copper, etc. 27,28,41,43,[50][51][52][53][54][55] All these methods are efficient, although some of them require long reaction time, high temperature and long reflux periods. 43,54,55 As mentioned, all these methods 27,28,41,43,[50][51][52][53][54][55] are based on the chemical reaction between the metal ion and the drug (chemical method) and in them, it is necessary to use the salt of related metals.…”

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confidence: 99%

“…27,28,41,43,[50][51][52][53][54][55] All these methods are efficient, although some of them require long reaction time, high temperature and long reflux periods. 43,54,55 As mentioned, all these methods 27,28,41,43,[50][51][52][53][54][55] are based on the chemical reaction between the metal ion and the drug (chemical method) and in them, it is necessary to use the salt of related metals. On the other hand, to the best of our knowledge, no electrochemical methods have been reported for the complexation of these drugs.…”

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confidence: 99%

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Green Electrochemical Complexation of Fluconazole, Itraconazole, Voriconazole, Ketoconazole and Clotrimazole with Silver, Copper and Zinc Cations

Godini,

Nematollahi,

Zivari-Moshfegh

2023

J. Electrochem. Soc.

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Electrochemical complexation of azole antifungal drugs fluconazole, itraconazole, ketoconazole, voriconazole, and clotrimazole with silver, copper, and zinc cations was carried out galvanostatically in an undivided electrolytic cell equipped with a sacrificial anode under green conditions. In this work, we synthesized 20 different complexes of these drugs by a simple method in water (containing a strong acid)/ethanol mixtures with high yield (average 67%) and purity. The effective synthetic parameters, including the applied current, electricity consumption, acid concentration, cell voltage, energy consumption, and cell design were optimized. Our results indicate that the applied current and acid concentration have no significant effects on the yield and purity of azole complexes. But these factors have a significant effect on cell voltage and energy consumption in such a way that by increasing the applied current or decreasing the acid concentration, the cell voltage and energy consumption increase. Fourier transform infrared spectroscopy, field-emission scanning electron microscopy and energy-dispersive X-ray techniques have been used for the characterization of synthesized complexes. In addition, cyclic voltammetry analysis has been used to investigate the reaction mechanism. This method provides an efficient and green strategy for the complexation of azole drugs in one step without the need for metal salts.

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Biosynthesis of ergosterol as a relevant molecular target of metal-based antiparasitic and antifungal compounds

Scalese,

Mosquillo,

Pérez-Díaz

et al. 2024

Coordination Chemistry Reviews

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Promising fluconazole based zinc(II) and copper(II) coordination polymers against Chagas disease

Cited by 7 publications

References 34 publications

In Vitro Effects of Aminopyridyl Ligands Complexed to Copper(II) on the Physiology and Interaction Process of Trypanosoma cruzi

In Vitro Effects of Aminopyridyl Ligands Complexed to Copper(II) on the Physiology and Interaction Process of Trypanosoma cruzi

Green Electrochemical Complexation of Fluconazole, Itraconazole, Voriconazole, Ketoconazole and Clotrimazole with Silver, Copper and Zinc Cations

Biosynthesis of ergosterol as a relevant molecular target of metal-based antiparasitic and antifungal compounds

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