Synthesis, characterization and antiamoebic activity of chalcones bearing N-substituted ethanamine tail

Zaidi, Saadia Leeza; Mittal, Sonam; Rajala, Maitreyi S.; Avecilla, Fernando; Husain, Mohammad; Azam, Amir

doi:10.1016/j.ejmech.2015.05.013

Cited by 17 publications

(3 citation statements)

References 32 publications

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“…Chalcones are the important class of antamoebic drugs and their analogs have been synthesized having better activity. A series of chalcones were synthesized bearing N-substituted ethanamine by aldol condensation reaction and the compound ( 17 ) was found to be very potent amoebicidal indicating that such compounds can be the effective therapeutic candidates (Zaidi et al, 2015 ). Metronidazole hydrazone conjugates were synthesized and screened in vitro for antiamoebic activity, the compound ( 18 ) was found more active (Ansari et al, 2015 ).…”

Section: Entamoeba Histolyticamentioning

confidence: 99%

Parasitic diarrheal disease: drug development and targets

2015

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Diarrhea is the manifestation of gastrointestinal infection and is one of the major causes of mortality and morbidity specifically among the children of less than 5 years age worldwide. Moreover, in recent years there has been a rise in the number of reports of intestinal infections continuously in the industrialized world. These are largely related to waterborne and food borne outbreaks. These occur by the pathogenesis of both prokaryotic and eukaryotic organisms like bacteria and parasites. The parasitic intestinal infection has remained mostly unexplored and under assessed in terms of therapeutic development. The lack of new drugs and the risk of resistance have led us to carry out this review on drug development for parasitic diarrheal diseases. The major focus has been depicted on commercially available drugs, currently synthesized active heterocyclic compounds and unique drug targets, that are vital for the existence and growth of the parasites and can be further exploited for the search of therapeutically active anti-parasitic agents.

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Section: Entamoeba Histolyticamentioning

confidence: 99%

Parasitic diarrheal disease: drug development and targets

2015

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“…Chalcones have been considered promising molecules due to their broad range of biological activities, multi-target action, simple chemistry and low toxicity [ 31 ]. The effect of chalcones and their derivatives has already been described for other protozoa [ 20 , 21 , 26 , 32 , 33 ]. In a previous screening, our group selected a chalcone derivative named NaF based on its activity in reducing P. serpens viability in vitro [ 29 ].…”

Section: Discussionmentioning

confidence: 98%

Chalcone Derivative Induces Flagellar Disruption and Autophagic Phenotype in Phytomonas serpens In Vitro

et al. 2023

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Phytomonas serpens is a trypanosomatid phytoparasite, found in a great variety of species, including tomato plants. It is a significant problem for agriculture, causing high economic loss. In order to reduce the vegetal infections, different strategies have been used. The biological activity of molecules obtained from natural sources has been widely investigated to treat trypanosomatids infections. Among these compounds, chalcones have been shown to have anti-parasitic and anti-inflammatory effects, being described as having a remarkable activity on trypanosomatids, especially in Leishmania species. Here, we evaluated the antiprotozoal activity of the chalcone derivative (NaF) on P. serpens promastigotes, while also assessing its mechanism of action. The results showed that treatment with the derivative NaF for 24 h promotes an important reduction in the parasite proliferation (IC50/24 h = 23.6 ± 4.6 µM). At IC50/24 h concentration, the compound induced an increase in reactive oxygen species (ROS) production and a shortening of the unique flagellum of the parasites. Electron microscopy evaluation reinforced the flagellar phenotype in treated promastigotes, and a dilated flagellar pocket was frequently observed. The treatment also promoted a prominent autophagic phenotype. An increased number of autophagosomes were detected, presenting different levels of cargo degradation, endoplasmic reticulum profiles surrounding different cellular structures, and the presence of concentric membranar structures inside the mitochondrion. Chalcone derivatives may present an opportunity to develop a treatment for the P. serpens infection, as they are easy to synthesize and are low in cost. In order to develop a new product, further studies are still necessary.

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“…Other compounds with anti-amebic effects are the chalcones. Leeza Zaidi et al ( 2015 ) synthetized modified chalcones (N-substituted ethanamine). In vitro assays showed that their derivatives displayed a better anti-amebic activity than the MTZ reference drug (Leeza Zaidi et al, 2015 ).…”

Section: In Vitro Studies and Molecular Targetsmentioning

confidence: 99%

Flavonoids as a Natural Treatment Against Entamoeba histolytica

Martínez-Castillo

Pacheco‐Yépez

Flores-Huerta

et al. 2018

Front. Cell. Infect. Microbiol.

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Over the past 20 years, gastrointestinal infections in developing countries have been a serious health problem and are the second leading cause of morbidity among all age groups. Among pathogenic protozoans that cause diarrheal disease, the parasite Entamoeba histolytica produces amebic colitis as well as the most frequent extra-intestinal lesion, an amebic liver abscess (ALA). Usually, intestinal amebiasis and ALA are treated with synthetic chemical compounds (iodoquinol, paromomycin, diloxanide furoate, and nitroimidazoles). Metronidazole is the most common treatment for amebiasis. Although the efficacy of nitroimidazoles in killing amebas is known, the potential resistance of E. histolytica to this treatment is a concern. In addition, controversial studies have reported that metronidazole could induce mutagenic effects and cerebral toxicity. Therefore, natural and safe alternative drugs against this parasite are needed. Flavonoids are natural polyphenolic compounds. Flavonoids depend on malonyl-CoA and phenylalanine to be synthesized. Several flavonoids have anti-oxidant and anti-microbial properties. Since the 1990s, several works have focused on the identification and purification of different flavonoids with amebicidal effects, such as, -(-)epicatechin, kaempferol, and quercetin. In this review, we investigated the effects of flavonoids that have potential amebicidal activity and that can be used as complementary and/or specific therapeutic strategies against E. histolytica trophozoites. Interestingly, it was found that these natural compounds can induce morphological changes in the amebas, such as chromatin condensation and cytoskeletal protein re-organization, as well as the upregulation and downregulation of fructose-1,6-bisphosphate aldolase, glyceraldehyde-phosphate dehydrogenase, and pyruvate:ferredoxin oxidoreductase (enzymes of the glycolytic pathway). Although the specific molecular targets, bioavailability, route of administration, and doses of some of these natural compounds need to be determined, flavonoids represent a very promising and innocuous strategy that should be considered for use against E. histolytica in the era of microbial drug resistance.

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Synthesis, characterization and antiamoebic activity of chalcones bearing N-substituted ethanamine tail

Cited by 17 publications

References 32 publications

Parasitic diarrheal disease: drug development and targets

Parasitic diarrheal disease: drug development and targets

Chalcone Derivative Induces Flagellar Disruption and Autophagic Phenotype in Phytomonas serpens In Vitro

Flavonoids as a Natural Treatment Against Entamoeba histolytica

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