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Development of eugenol derivatives with 5-LOX inhibitory activity

Filho, José L. Pereira; Pereira, Renato B.; Vieira, Tatiana F.; Sousa, Sérgio F.; Coelho, José Ricardo Alves; Pinto, Nuno F. S.; Coelho, Catarina M. M.

Eugenol (4-allyl-2-methoxyphenol), is the major chemical constituent in the essential oil of numerous plant species. Several biological properties have been described for this molecule, including modulation of enzymatic targets relevant for the inflammatory response, such as 5-lipoxygenase (5-LOX). As so, there is interest in expanding the chemical space of this molecule to develop new molecules to be used in i...


The fungicide cymoxanil impairs respiration in Saccharomyces cerevisiae via cyt...

Mendes, Filipa Diana Silva; Santos-Pereira, Cátia; Vieira, Tatiana F.; Pinto, Mélanie Martins; Castro, Bruno B.; Sousa, Sérgio F.; Sousa, Maria João

Cymoxanil (CYM) is a widely used synthetic acetamide fungicide, but its biochemical mode of action remains elusive. Since CYM inhibits cell growth, biomass production, and respiration in Saccharomyces cerevisiae, we used this model to characterize the effect of CYM on mitochondria. We found it inhibits oxygen consumption in both whole cells and isolated mitochondria, specifically inhibiting cytochrome c oxidase...


Cymoxanil inhibits respiration through inhibition of mitochondrial complex IV

Mendes, Filipa; Vieira, Tatiana F.; Pereira, Cátia Sofia Santos; Pinto, Mélanie Martins; Castro, Bruno B.; Sousa, Sérgio F.; Sousa, Maria João

Cymoxanil is a synthetic acetamide fungicide, used against oomycetes. It was first introduced in 1977 and can be used against downy mildew diseases induced by Plasmopara viticola in grapevine cultures and late blight diseases caused by Phytophthora infestans, in tomatoes and potatoes cultures. This fungicide is used in mixed formulations and its higher solubility enables a relatively widespread occurrence in to...


Liposomal formulations loaded with a eugenol derivative for application as inse...

Fernandes, Maria José Gomes; Pereira, Renato B.; Rodrigues, Ana Rita Oliveira; Vieira, Tatiana F.; Fortes, A. Gil; Pereira, David M.; Sousa, Sérgio F.

A recently synthesized new eugenol derivative, ethyl 4-(2-methoxy-4-(oxiran-2-ylmethyl)phenoxy)butanoate, with a high insecticidal activity against Sf9 (Spodoptera frugiperda) insect cells, was encapsulated in the liposomal formulations of egg-phosphatidylcholine/cholesterol (Egg-PC:Ch) 70:30 and 100% dioleoylphosphatidylglycerol (DOPG), aiming at the future application as insecticides. Compound-loaded DOPG lip...


Synthesis, computational and nanoencapsulation studies on eugenol-derived insec...

Coelho, Catarina M. M.; Pereira, Renato B.; Vieira, Tatiana F.; Teixeira, Cláudia M.; Fernandes, Maria José Gomes; Rodrigues, Ana Rita O.

A new set of alkoxy alcohols were synthesised by reaction of eugenol oxirane with aliphatic and aromatic alcohols. These eugenol derivatives were evaluated against their effect upon the viability of the insect cell line Sf9 (Spodoptera frugiperda). The most promising compounds, 4-(3-(tert-butoxy)-2-hydroxypropyl)-2-methoxyphenol and 4-(2-((4-fluorobenzyl)oxy)-3-hydroxypropyl)-2-methoxyphenol were submitted to i...


New carvacrol and thymol derivatives as potential insecticides: synthesis, biol...

Natal, Carolina M.; Fernandes, Maria José Gomes; Pinto, Nuno F. S.; Pereira, Renato B.; Vieira, Tatiana F.; Rodrigues, Ana Rita Oliveira

New compounds with potential insecticide activity were synthesized by structural modifications performed in the monoterpenoids phenolic moieties of carvacrol and thymol, resulting in a set of derivatives with the ether function containing the propyl, chloropropyl or hydroxypropyl chains, as well as a bicyclic ether with an unsaturated chain containing a carboxylic acid terminal. In addition, an analogue of carv...


Amino alcohols from eugenol as potential semisynthetic insecticides: chemical, ...

Pereira, Renato B.; Pinto, Nuno F. S.; Fernandes, Maria José Gomes; Vieira, Tatiana F.; Rodrigues, Ana Rita Oliveira; Pereira, David M.

A series of β-amino alcohols were prepared by the reaction of eugenol epoxide with aliphatic and aromatic amine nucleophiles. The synthesized compounds were fully characterized and evaluated as potential insecticides through the assessment of their biological activity against Sf9 insect cells, compared with a commercial synthetic pesticide (chlorpyrifos, CHPY). Three derivatives bearing a terminal benzene ring,...


Selection of a new peptide homing SK-BR-3 breast cancer cells

Pereira, Ana Cláudia Santos; Ferreira, Débora; Santos-Pereira, Cátia; Vieira, Tatiana F.; Sousa, Sérgio F.; Sales, M. G. F.; Rodrigues, L. R.

Breast cancer diagnosis remains a challenge, mostly due to its heterogeneity. This reality translates in delayed treatments, increasing treatment aggressiveness and lower chances of overall survival. The conventional detection techniques, although becoming increasingly sophisticated each year, still lack the ability to provide reliable conclusions without being time consuming, expensive and uncomfortable for th...


Desenvolvimento e validação de um método para a análise de conservantes em vinh...

Vieira, Tatiana F.; Simões, T.; Ribeiro, Natália; Oliveira, Ana; Bettencourt, Ana Paula


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