Mesoionic compounds with antifungal activity against Fusarium verticillioides

Abstract

BackgroundFungi contaminate the food of humans and animals, are a risk to health, and can cause financial losses. In this work, the antifungal activities of 16 mesoionic compounds (MI 1–16) were evaluated against mycotoxigenic fungi, including Aspergillus spp., Fusarium verticillioides and Penicillium citrinum. Furthermore, the decreased ergosterol in the total lipid content of Fusarium verticillioides was investigated.ResultsF. verticillioides was the most sensitive fungus to the mesoionic compounds. Among the evaluated compounds, MI-11 and MI-16 presented higher antifungal effects against F. verticillioides, with MIC values of 7.8 μg/ml, and MI-2 and MI-3 followed, with MICs of 15.6 μg/ml. The most active compounds were those with heterocyclic ring phenyl groups substituted by electron donor moieties (MI-11 and MI-16). Among some compounds with higher activity (MI-2, MI-11 and MI-16), decreased ergosterol content in the total lipid fraction of F. verticillioides was demonstrated. MI-2 reduced the ergosterol content approximately 40% and 80% at concentrations of 7.8 μg/ml and 15.6 μg/ml, respectively, and MI-11 and MI-16 decreased the content by 30% and 50%, respectively, when at a concentration of 7.8 μg/ml.ConclusionThese findings indicate that mesoionic compounds have significant antifungal activity against F. verticillioides.

Synthetic (E)-3-Phenyl-5-(phenylamino)-2-styryl-1,3,4-thiadiazol-3-ium Chloride Derivatives as Promising Chemotherapy Agents on Cell Lines Infected with HTLV-1

“…The intermediates 4a-d were prepared in solvent free conditions using a grinding method with aryl-isothiocyanates and phenyl-hydrazine at room temperature for 2 min. These compounds were obtained in quantitative yields and high purity, and their structures were confirmed by FT-IR spectroscopy and NMR 1 H and 13 C spectrometry, in accordance with previous publications on mesoionic compounds [29,50]. The (E)-3-phenyl-5-(phenylamino)-2-styryl-1,3,4-thiadiazol-3-ium chloride derivatives (5a-d) were prepared by reaction of cinnamaldehyde and the N-aryl-2-phenyl-hydrazinecarbothioamides (4a-d) in equimolar amounts, thionyl chloride (excess of three times), and enough drops of 1,4dioxane to homogenize the reagents.…”

“…The intermediates 4a-d were prepared in solvent free conditions using a grinding method with aryl-isothiocyanates and phenyl-hydrazine at room temperature for 2 min. These compounds were obtained in quantitative yields and high purity, and their structures were confirmed by FT-IR spectroscopy and NMR 1 H and 13 C spectrometry, in accordance with previous publications on mesoionic compounds [29,50]. with HTLV-1 and a Jurkat cell line (lymphocytic leukemia).…”

“…The solid formed was obtained in high purity without recrystallization. All mesoionic chlorides ( Figure 10) were identified by melting point, FT-IR, NMR data, and elemental analyses [29].…”

“…In addition, it was also investigated how the mesoionic compounds 5a-d induce apoptotic cell death, as well as their preliminary pharmacokinetic profile via affinity for HSA by multiple spectroscopic techniques combined with molecular docking. It is important to highlight that the synthesis of the mesoionic compounds 5a, 5b, and 5d have already been described [29] (5c is a new synthetic mesoionic), however, this work reports for the first time the evaluation of 5a-d as promising chemotherapy agents.…”

“…Each compound was assayed against C91 and MT2 cell lines infected Heterocyclic compounds of the mesoionic class, especially those with 1,3,4-thiadiazole moiety, have been synthesized and their biological effects investigated, confirming their excellent potential biological activity. Different biological activities have been described for these compounds, such as anticancer [20][21][22][23], antiparasitic [24][25][26], anti-inflammatory, analgesic [27,28], and antimicrobial [29,30]. Mesoionic compounds have a betaine-like characteristic, with a positive charge on the heterocyclic ring and a negative charge on the exocyclic atom and, therefore, can be represented only by dipolar structures [31].…”