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3 results on '"Bruna D. P. Costa"'

1. Ring-Fused meso-Tetraarylchlorins as Auspicious PDT Sensitizers: Synthesis, Structural Characterization, Photophysics, and Biological Evaluation

Author

Mafalda Laranjo, Nelson A. M. Pereira, Andreia S. R. Oliveira, Márcia Campos Aguiar, Gonçalo Brites, Bruno F. O. Nascimento, Beatriz Serambeque, Bruna D. P. Costa, João Pina, J. Sérgio Seixas de Melo, Marta Pineiro, M. Filomena Botelho, and Teresa M. V. D. Pinho e Melo

Subjects
chlorins, photodynamic therapy, photosensitizer, subcellular accumulation, cancer, Chemistry, QD1-999
Abstract

Novel 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-fused meso-tetraarylchlorins, with different degrees of hydrophilicity (with methyl ester, hydroxymethyl, and carboxylic acid moieties), have been synthesized and their photophysical characterization as well as in vitro photocytotoxicity assessment against human melanoma and esophageal and bladder carcinomas was carried out. An integrated analysis of the photosensitizers’ performance, considering the singlet oxygen generation data, cell internalization, and intracellular localization, allowed to establish relevant structure-photoactivity relationships and the rationalization of the observed photocytotoxicity. In the diacid and monoalcohol series, chlorins derived from meso-tetraphenylporphyrin proved to be the most efficient photodynamic therapy agents, showing IC50 values of 68 and 344 nM against A375 cells, respectively. These compounds were less active against OE19 and HT1376 cells, the diacid chlorin with IC50 values still in the nano-molar range, whereas the monohydroxymethyl-chlorin showed significantly higher IC50 values. The lead di(hydroxymethyl)-substituted meso-tetraphenylchlorin confirmed its remarkable photoactivity with IC50 values below 75 nM against the studied cancer cell lines. Subcellular accumulation of this chlorin in the mitochondria, endoplasmic reticulum, and plasma membrane was demonstrated.

Published
2022
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2. Ring-Fused

Author

Mafalda, Laranjo, Nelson A M, Pereira, Andreia S R, Oliveira, Márcia, Campos Aguiar, Gonçalo, Brites, Bruno F O, Nascimento, Beatriz, Serambeque, Bruna D P, Costa, João, Pina, J Sérgio, Seixas de Melo, Marta, Pineiro, M Filomena, Botelho, and Teresa M V D, Pinho E Melo

Abstract

Novel 4,5,6,7-tetrahydropyrazolo[1,5

Published
2022

3. Novel fluorinated ring-fused chlorins as promising PDT agents against melanoma and esophagus cancer

Author

Mafalda Laranjo, João Simões, João Pina, Maria Filomena Botelho, J. Sérgio Seixas de Melo, Bruno F.O. Nascimento, Teresa M. V. D. Pinho e Melo, Bruna D P Costa, Marta Pineiro, João Braz, Gonçalo Brites, and Nelson A. M. Pereira

Subjects
Pharmacology, 0303 health sciences, 010405 organic chemistry, Singlet oxygen, Organic Chemistry, Diol, Pharmaceutical Science, Quantum yield, Pyrazole, 01 natural sciences, Biochemistry, Combinatorial chemistry, Porphyrin, Cycloaddition, 0104 chemical sciences, 03 medical and health sciences, chemistry.chemical_compound, Chemistry, chemistry, Drug Discovery, polycyclic compounds, Molecular Medicine, Moiety, Photosensitizer, 030304 developmental biology
Abstract

Investigation of novel 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-fused chlorins, derived from 5,10,15,20-tetrakis(pentafluorophenyl)porphyrin, as PDT agents against melanoma and esophagus cancer is disclosed. Diol and diester fluorinated ring-fused chlorins, including derivatives with 2-(2-hydroxyethoxy)ethanamino groups at the phenyl rings, were obtained via a two-step methodology, combining S(N)Ar and [8π + 2π] cycloaddition reactions. The short-chain PEG groups at the para-position of the phenyl rings together with the diol moiety at the fused pyrazole ring promote a red-shift of the Soret band, a decrease of the fluorescence quantum yield and an increase of the singlet oxygen formation quantum yield, improving the photophysical characteristics required to act as a photosensitizer. Introduction of these hydrophilic groups also improves the incorporation of the sensitizers by the cells reaching cellular uptake values of nearly 50% of the initial dose. The rational design led to a photosensitizer with impressive IC(50) values, 13 and 27 nM against human melanoma and esophageal carcinoma cell lines, respectively.

Published
2021

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