Please use this identifier to cite or link to this item: https://hdl.handle.net/10316/107505
Title: Novel fluorinated ring-fused chlorins as promising PDT agents against melanoma and esophagus cancer
Authors: Pereira, Nelson A. M. 
Laranjo, Mafalda 
Nascimento, Bruno F. O. 
Simões, João C. S. 
Pina, João 
Costa, Bruna D. P. 
Brites, Gonçalo Sousa 
Braz, João 
Melo, J. Sérgio Seixas de 
Piñeiro Gomez, Marta 
Botelho, Maria Filomena 
Pinho e Melo, Teresa M. V. D. 
Keywords: Photodynamic Therapy; Ring-Fused Chlorins; PEGylated Photosensitizers; Fluorinated Photosensitizer; Skin Malignant Melanoma; Esophageal Adenocarcinoma
Issue Date: 28-Apr-2021
Publisher: Royal Society of Chemistry
Project: UIDB/00313/2020 
UIDP/QUI/00313/2020 
UID/NEU/04539/2013 
POCI-01-0145-FEDER-007440 
UIDB/04539/2020 
UIDP/04539/2020 
CIMAGO/06/2019/ 
info:eu-repo/grantAgreement/MATIS/CENTRO-01-0145-FEDER-000014/PT 
Serial title, monograph or event: RSC Medicinal Chemistry
Volume: 12
Issue: 4
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 SNAr 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 IC50 values, 13 and 27 nM against human melanoma and esophageal carcinoma cell lines, respectively.
URI: https://hdl.handle.net/10316/107505
DOI: 10.1039/d0md00433b
Rights: embargoedAccess
Appears in Collections:FMUC Medicina - Artigos em Revistas Internacionais
I&D CIBB - Artigos em Revistas Internacionais
I&D ICBR - Artigos em Revistas Internacionais
I&D CQC - Artigos em Revistas Internacionais

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