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Cytotoxic Terphenyl Neolignans from Fungus Terana coerulea: New Natural Corticins D and E, and Revised Structure for Corticin A

Publication . Maisterra Udi, Maitane; Castro, María Ángeles; Muñoz-Centeno, Luz M.; Calhelha, Ricardo C.; Ferreira, Isabel C.F.R.; García, Pablo A.

The cobalt crust fungus Terana coerulea (Phanerochaetaceae family) was selected for a bio-guided study after an ethnobotanical survey at the Irati's Forest (Navarra, Spain) for its local use as antibiotic. Six extracts of increasing polarity, from hexane to hot water, were obtained from powdered dry fungi and tested for cytotoxicity against four human tumour cell lines and one non-tumour primary cell culture. From the most cytotoxic, EtOAc extract, we isolated and identified three terphenyl neolignans: two of them new natural products, named corticins D and E, and one previously described as corticin A, whose earlier structure has been revised. Their structural elucidation and biological evaluation as cytotoxic agents are described.

2017Journal article

Open access

Methyl 3-[4-(3-arylureido)phenylamino]thieno[3,2-b]pyridine-2-carboxylates as potential inhibitors of VEGFR-2: synthesis and molecular modelling studies

Publication . Peixoto, Daniela; Calhelha, Ricardo C.; Dias, Sofia; Froufe, Hugo J.C.; Abreu, Rui M.V.; Ferreira, Isabel C.F.R.; Queiroz, Maria João R.P.

When over expressed or mutated, protein tyrosine kinases become potent oncoproteins that cause deregulated cell growth angiogenesis and metastasis. Because of these characteristics, they are targets for small molecule inhibitors in the treatment of cancer. Recently some thieno[3,2-c]pyridine 1,3-diarylurea derivatives were prepared as VEGFR-2 (vascular endothelium growth factor receptor-2) inhibitors.1 Here we present the synthesis of methyl 3-[4-(3-arylureido)phenylamino]thieno[3,2-b]pyridine-2-carboxylates 2 in excellent yields, by reaction of the methyl 3-(4-aminophenylamino)thieno[3,2-b]pyridine-2-carboxylate 1, prepared also by us, with different arylisocyanates (Scheme).

2011Conference object

Open access

Measurement of red blood cells deformation index in a hyperbolic microchannel

Publication . Faustino, Vera; Pinho, Diana; Yaginuma, Tomoko; Calhelha, Ricardo C.; Man-Kim, Gyeong; Arana, Sergio; Lima, Rui A.; Ferreira, Isabel C.F.R.; Oliveira, Mónica S.N.

A hyperbolic microchannel was used for the purpose of observing the deformation index of the erythrocytes after contact with human tumour cell line (HCT-15 - colon carcinoma). Three cases were compared and the results showed that the deformation index decreases when erythrocytes are in contact with HCT-15.

2013Conference object

Open access

New potential anti-hepatocellular carcinoma (HCC) agents: in vitro evaluation of anti-HCC activity and hepatotoxicity of 6-substituted methyl 3-aminothieno[3,2-b]pyridine-2-carboxylates and QSAR studies

Publication . Abreu, Rui M.V.; Queiroz, Maria João R.P.; Ferreira, Isabel C.F.R.; Calhelha, Ricardo C.; Adega, Filomena; Chaves, Raquel

Hepatocellular carcinoma (HCC) is a major health problem with more than 660,000 new cases per year worldwide [1]. HCC is resistant to commonly used treatments like chemotherapy and radiotherapy and new anti-HCC therapies are urgently needed. Sorafenib was the first approved small molecule against HCC and underlines the importance of identifying potential new anti-HCC drugs [2]. Thirty-two 6-substituted methyl 3-aminothieno[3,2-b]pyridine-2-carboxylates, previously prepared by some of us [3,4], were evaluated as potential new anti-HCC agents by studying their in vitro cell growth inhibition on human HepG2 cells, generally regarded as a good HCC model, and hepatotoxicity using a porcine liver primary cell culture (PLP1). The presence of amino groups linked to a benzene moiety on the substituent of the 6-position emerged as the key element for the anti-HCC activity.

2011Conference object

Open access

Wild mushrooms and their mycelia as sources of bioactive compounds: Antioxidant, anti-inflammatory and cytotoxic properties

Publication . Souilem, Fedia; Fernandes, Ângela; Calhelha, Ricardo C.; Barreira, João C.M.; Barros, Lillian; Skhiri, Fathia; Martins, Anabela; Ferreira, Isabel C.F.R.

Mushrooms are important sources of natural bioactive compounds. Pleurotus eryngii (DC.) Quél is recognized for its organoleptic quality and health effects, being extensively commercialized. Instead, Suillus bellinii (Inzenga) Watling is an ectomycorrhizal symbiont, whose main properties were scarcely reported. Considering current trends, the mycelia and the culture media of these mushrooms might be potential sources of bioactive compounds. Accordingly, P. eryngii and S. bellinii were studied for their phenolic acids and sterols, antioxidant capacity, anti-inflammatory effect and anti-proliferative activity. S. bellinii mycelia showed higher contents of ergosterol and phenolic compounds (also higher in its fruiting body) and stronger antioxidant activity than P. eryngii. Conversely, P. eryngii mycelia showed anti-inflammatory (absent in S. bellinii mycelia) and a cytotoxicity similar (sometimes superior) to its fruiting bodies, contrarily to S. bellinii. Furthermore, the assayed species showed differences in the growth rate and produced mycelia, which should be considered in further applications.

2017Journal article

Open access