Photoactivated cell-killing amino-based flavylium compounds

Abstract Photodynamic therapy (PDT) is a well-established therapeutic for the treatment of different diseases. The growing interest of this technique required the development of new photosensitizers with better photo-features. This work reports the study of the potential of five nature-inspired amin...

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Autores principales:	Hélder Oliveira, Paula Araújo, Ana Rita Pereira, Nuno Mateus, Victor de Freitas, Joana Oliveira, Iva Fernandes
Formato:	article
Lenguaje:	EN
Publicado:	Nature Portfolio 2021
Materias:	Medicine R Science Q
Acceso en línea:	https://doaj.org/article/ba2a2ba6a7ff405b985ce868af61ddb2
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spelling	oai:doaj.org-article:ba2a2ba6a7ff405b985ce868af61ddb22021-11-14T12:18:53ZPhotoactivated cell-killing amino-based flavylium compounds10.1038/s41598-021-01485-y2045-2322https://doaj.org/article/ba2a2ba6a7ff405b985ce868af61ddb22021-11-01T00:00:00Zhttps://doi.org/10.1038/s41598-021-01485-yhttps://doaj.org/toc/2045-2322Abstract Photodynamic therapy (PDT) is a well-established therapeutic for the treatment of different diseases. The growing interest of this technique required the development of new photosensitizers with better photo-features. This work reports the study of the potential of five nature-inspired amino-based flavylium compounds with different structural features as photosensitizers towards topical PDT. In terms of dark cytotoxicity the five pigments were tested towards confluent skin cells in both fibroblasts and keratinocytes. In the range of concentrations tested (6.3–100 μM), keratinocytes were more prone to growth inhibition and the IC50 values for 5OH4′NMe2, 7NEt2st4′NMe2 and 7NEt24′NH2 were determined to be 47.3 ± 0.3 μM; 91.0 ± 0.8 μM and 29.8 ± 0.8 μM, respectively. 7NEt24′NMe2, 7NEt2st4′NMe2 and 7NEt24′NH2 showed significant fluorescence quantum yields (from 3.40 to 20.20%) and production of singlet oxygen (1O2). These latter chromophores presented IC50 values of growth inhibition of keratinocytes between 0.9 and 1.5 µM, after 10 min of photoactivation with white light. This cellular damage in keratinocyte cells upon white light activation was accompanied with the production of reactive oxygen species (ROS). It was also found that the compounds can induce damage by either type I (ROS production) or type II (singlet oxygen) PDT mechanism, although a higher cell survival was observed in the presence of 1O2 quenchers. Overall, a structure–activity relationship could be established, ranking the most important functional groups for the photoactivation efficiency as follows: C7-diethylamino > C4′-dimethylamino > C2-styryl.Hélder OliveiraPaula AraújoAna Rita PereiraNuno MateusVictor de FreitasJoana OliveiraIva FernandesNature PortfolioarticleMedicineRScienceQENScientific Reports, Vol 11, Iss 1, Pp 1-16 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	Medicine R Science Q
spellingShingle	Medicine R Science Q Hélder Oliveira Paula Araújo Ana Rita Pereira Nuno Mateus Victor de Freitas Joana Oliveira Iva Fernandes Photoactivated cell-killing amino-based flavylium compounds
description	Abstract Photodynamic therapy (PDT) is a well-established therapeutic for the treatment of different diseases. The growing interest of this technique required the development of new photosensitizers with better photo-features. This work reports the study of the potential of five nature-inspired amino-based flavylium compounds with different structural features as photosensitizers towards topical PDT. In terms of dark cytotoxicity the five pigments were tested towards confluent skin cells in both fibroblasts and keratinocytes. In the range of concentrations tested (6.3–100 μM), keratinocytes were more prone to growth inhibition and the IC50 values for 5OH4′NMe2, 7NEt2st4′NMe2 and 7NEt24′NH2 were determined to be 47.3 ± 0.3 μM; 91.0 ± 0.8 μM and 29.8 ± 0.8 μM, respectively. 7NEt24′NMe2, 7NEt2st4′NMe2 and 7NEt24′NH2 showed significant fluorescence quantum yields (from 3.40 to 20.20%) and production of singlet oxygen (1O2). These latter chromophores presented IC50 values of growth inhibition of keratinocytes between 0.9 and 1.5 µM, after 10 min of photoactivation with white light. This cellular damage in keratinocyte cells upon white light activation was accompanied with the production of reactive oxygen species (ROS). It was also found that the compounds can induce damage by either type I (ROS production) or type II (singlet oxygen) PDT mechanism, although a higher cell survival was observed in the presence of 1O2 quenchers. Overall, a structure–activity relationship could be established, ranking the most important functional groups for the photoactivation efficiency as follows: C7-diethylamino > C4′-dimethylamino > C2-styryl.
format	article
author	Hélder Oliveira Paula Araújo Ana Rita Pereira Nuno Mateus Victor de Freitas Joana Oliveira Iva Fernandes
author_facet	Hélder Oliveira Paula Araújo Ana Rita Pereira Nuno Mateus Victor de Freitas Joana Oliveira Iva Fernandes
author_sort	Hélder Oliveira
title	Photoactivated cell-killing amino-based flavylium compounds
title_short	Photoactivated cell-killing amino-based flavylium compounds
title_full	Photoactivated cell-killing amino-based flavylium compounds
title_fullStr	Photoactivated cell-killing amino-based flavylium compounds
title_full_unstemmed	Photoactivated cell-killing amino-based flavylium compounds
title_sort	photoactivated cell-killing amino-based flavylium compounds
publisher	Nature Portfolio
publishDate	2021
url	https://doaj.org/article/ba2a2ba6a7ff405b985ce868af61ddb2
work_keys_str_mv	AT helderoliveira photoactivatedcellkillingaminobasedflavyliumcompounds AT paulaaraujo photoactivatedcellkillingaminobasedflavyliumcompounds AT anaritapereira photoactivatedcellkillingaminobasedflavyliumcompounds AT nunomateus photoactivatedcellkillingaminobasedflavyliumcompounds AT victordefreitas photoactivatedcellkillingaminobasedflavyliumcompounds AT joanaoliveira photoactivatedcellkillingaminobasedflavyliumcompounds AT ivafernandes photoactivatedcellkillingaminobasedflavyliumcompounds
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Photoactivated cell-killing amino-based flavylium compounds

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