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The synthesis of thiophenic compounds, previously identified in Tagetes patula, revealed that 4-(5′
-(hydroxymethyl)-[2,2′
-bithiophene]-5-yl)but-3-yn-1-ol), or simply Thio1, has a pronounced in vitro anthelmintic effect
against Haemonchus contortus, showing 100% efficacy in the egg hatch and larval development tests presenting
EC50 = 0.1731 mg.mL− 1 and EC50 = 0.3243 mg.mL− 1
, respectively. So, this compound was selected to preparation of a nanostructured formulation to be orally administered to Santa Inˆes sheep. In general, from the fecal
egg count reduction test (FECRT), it was observed that the product kept the parasitic load in the digestive tract of
the hosts stable, with eggs per gram of faeces (EPG) counts having a mean value < 3,000 (EPGmean = 2167.1,
efficacy = 36,45%), thus protecting the animals from health risks caused by a massive nematode infestation. To
better understand the mode of action of this thiophene derivative, in silico molecular modeling studies were
carried out with the glutamate-activated chloride channel (GluCl), a well-known molecular target of anthelmintic compounds. Based on the affinity score (GlideScore = -5.7 kcal.mol− 1
) and the proposed binding mode,
Thio1 could be classified as a potential GluCl ligand, justifying the promising results observed in the anthelmintic
assays.


Original text

The synthesis of thiophenic compounds, previously identified in Tagetes patula, revealed that 4-(5′
-(hydroxymethyl)-[2,2′
-bithiophene]-5-yl)but-3-yn-1-ol), or simply Thio1, has a pronounced in vitro anthelmintic effect
against Haemonchus contortus, showing 100% efficacy in the egg hatch and larval development tests presenting
EC50 = 0.1731 mg.mL− 1 and EC50 = 0.3243 mg.mL− 1
, respectively. So, this compound was selected to preparation of a nanostructured formulation to be orally administered to Santa Inˆes sheep. In general, from the fecal
egg count reduction test (FECRT), it was observed that the product kept the parasitic load in the digestive tract of
the hosts stable, with eggs per gram of faeces (EPG) counts having a mean value < 3,000 (EPGmean = 2167.1,
efficacy = 36,45%), thus protecting the animals from health risks caused by a massive nematode infestation. To
better understand the mode of action of this thiophene derivative, in silico molecular modeling studies were
carried out with the glutamate-activated chloride channel (GluCl), a well-known molecular target of anthelmintic compounds. Based on the affinity score (GlideScore = -5.7 kcal.mol− 1
) and the proposed binding mode,
Thio1 could be classified as a potential GluCl ligand, justifying the promising results observed in the anthelmintic
assays.

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