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Synthesis, photophysics, and potential antifungal activity of Benzo[a]phenoxazines

Guimarães, Bárbara S. G.; Sousa, Maria João; Gonçalves, M. Sameiro T.

The synthesis and full characterization of new hydroxyl benzo[a]phenoxazinium chlorides with N-(di)propyl and/or N-isopropyl groups in the 5 and 9 positions are described. Photophysical studies carried out in ethanol and water revealed strong absorbances and significant fluorescence emissions at up to 676 nm. The antifungal activity was assessed against Saccharomyces cerevisiae and the results provide possible ...


Benzo[a]phenoxazines as potential anti-inflammatory drugs

Pinto, Joana; Gonçalves, M. Sameiro T.; Pereira, David M.

The chemical diversity of natural products provides a promising source of anti-inflammatory drugs, notably targeting COX-2, whose activity is associated with inflammatory processes and carcinogenesis. The COX-2 and LOX inhibitory capacity of several benzo[a]phenoxazines, N- and O-heterocyclic compounds, was studied. The kinetic assay results revealed that these molecules significantly inhibit COX-2 activity, hi...


Combining fluconazole with benzo[a]phenoxazine derivatives as a promising strat...

Pacheco, Maria Inês Costa; Guimarães, Bárbara; Pereira-Silva, Patrícia; Costa-Barbosa, Augusto; Gonçalves, M. Sameiro T.; Sousa, Maria João

The rise in non-albicans Candida species, exhibiting unpredictable antifungal resistance, complicates treatment and contributes to the growing threat of invasive, life-threatening infections. This study evaluates the antifungal activity of four benzo[a]phenoxazine derivatives (C34, C35, A42, and A44) against 14 Candida strains following EUCAST standards. Fluconazole interactions are analysed through fractional ...


Anticancer activity of benzo[a]phenoxazine compounds promoting lysosomal dysfun...

Ferreira, João Carlos Canossa; Gonçalves, M. Sameiro T.; Preto, Ana; Sousa, Maria João

Specific cancer therapy remains a problem to be solved. Breast and colorectal cancer are among the cancers with the highest prevalence and mortality rates. Although there are some therapeutic options, there are still few effective agents for those cancers, which constitutes a clinical problem that requires further research efforts. Lysosomes play an important role in cancer cells’ survival, and targeting lysoso...


Phenolic compounds contribution to portuguese propolis anti-melanoma activity

Caetano, Ana Rita; Oliveira, Rafaela Dias; Celeiro, Sónia Pires; Freitas, Ana Sofia; Cardoso, Susana M.; Gonçalves, M. Sameiro T.; Baltazar, Fátima

Melanoma is the deadliest type of skin cancer, with about 61,000 deaths annually worldwide. Late diagnosis increases mortality rates due to melanoma’s capacity to metastasise rapidly and patients’ resistance to the available conventional therapies. Consequently, the interest in natural products as a strategy for drug discovery has been emerging. Propolis, a natural product produced by bees, has several biologic...


Targeting lysosomes in colorectal cancer: exploring the anticancer activity of ...

Ferreira, João C. C.; Granja, Sara Costa; Almeida, Ana F.; Baltazar, Fátima; Gonçalves, M. Sameiro T.; Preto, Ana; Sousa, Maria João

Colorectal cancer (CRC) has been ranked as one of the cancer types with a higher incidence and one of the most mortal. There are limited therapies available for CRC, which urges the finding of intracellular targets and the discovery of new drugs for innovative therapeutic approaches. In addition to the limited number of effective anticancer agents approved for use in humans, CRC resistance and secondary effects...


Evaluation of antifungal activity and potential application as fluorescent prob...

Gomes, Vanessa S. D.; Ferreira, João C. C.; Boto, Renato E.; Almeida, Paulo; Fernandes, José R.; Sousa, Maria João; Reis, Lucinda V.

The antifungal performance and the possible use as fluorescent probes of a series of squarylium dyes derived from indolenine and benzo[e]indole previously synthesized was evaluated. Some photophysical properties were performed in ethanol and phosphate buffer, and the type of aggregates form in phosphate buffer was analyzed. Using the 1,3-diphenylisobenzofuran assay, a qualitative assessment of the capacity of d...


Novel benzo[α]phenoxazinium chlorides functionalized with sulfonamide groups as...

Ferreira, J. C. C.; Sousa, Rui Pedro Carvalho Lima; Preto, Ana; Sousa, Maria João; Gonçalves, M. Sameiro T.

The demand for new fluorophores for different biological target imaging is increasing. Benzo[<i>a</i>]phenoxazine derivatives are fluorochromophores that show promising optical properties for bioimaging, namely fluorescent emission at the NIR of the visible region, where biological samples have minimal fluorescence emission. In this study, six new benzo[<i>a</i>]phenoxazinium chlorides possessing sulfonamide gr...


Inseticidas inspirados na natureza

Castanheira, Elisabete M. S.; Gonçalves, M. Sameiro T.

Uma equipa multidisciplinar dos Centros de Física e de Química da Universidade do Minho desenvolvem novos compostos de potencial inseticida melhorado. Desenvolvem-se também formulações de nanoencapsulamento para futura aplicação na agricultura.


Targeting lysosomes in colorectal cancer: exploring the anticancer activity of ...

Ferreira, João C. C.; Granja, Sara; Almeida, Ana F.; Baltazar, Fátima; Gonçalves, M. Sameiro T.; Preto, Ana; Sousa, Maria João

Colorectal cancer (CRC) has been ranked as one of the cancer types with a higher incidence and one of the most mortal. There are limited therapies available for CRC, which urges the finding of intracellular targets and the discovery of new drugs for innovative therapeutic approaches. In addition to the limited number of effective anticancer agents approved for use in humans, CRC resistance and secondary effects...


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