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Pereira, Nelson A. M; Laranjo, Mafalda; Nascimento, Bruno F. O; Simões, João C. S; Pina, João; Costa, Bruna D. P; Brites, Gonçalo; Braz, João; Seixas de Melo, J. Sérgio; Pineiro, Marta; Botelho, Maria Filomena; Pinho e Melo, Teresa M. V. D
MedChemComm, 04/2021, Letnik: 12, Številka: 4Journal Article
Investigation of novel 4,5,6,7-tetrahydropyrazolo1,5- 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. Novel 4,5,6,7-tetrahydropyrazolo1,5- a pyridine-fused chlorins, derived from 5,10,15,20-tetrakis(pentafluorophenyl)porphyrin, as impressive photosensitizers for photodynamic therapy of melanoma and esophagus cancer have been developed.
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JCR | SNIP | JCR | SNIP | JCR | SNIP | JCR | SNIP |
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in: SICRIS
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