Synthesis, photophysical properties, and photocytotoxic effects of porphyrin-diphenylalanine conjugates on HeLa cells

•Synthesis of four novel L,L-diphenylalanine (FF) functionalized porphyrins.•Photophysical studies showing that FF conjugation influences porphyrin aggregation.•Post-irradiation with 650 nm light decreased cell viability of a cervical tumor cell line to 70 %, with no cell death induced without light...

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Published in:	Journal of molecular structure Vol. 1322; p. 140545
Main Authors:	Vassiliades, Sandra V., Argüello, Karina A.B., Castro, Carlos E., Silva, Clovis A., Gonzalez, Ana Clara, Homem-de-Mello, Paula, Nantes, Iseli Lourenço, Aguilar, Andrea M., Barbosa-Reis, Gustavo, Oliveira-Silva, Diogo, Giuntini, Francesca, Alves, Wendel A.
Format:	Journal Article
Language:	English
Published:	Elsevier B.V 15-02-2025
Subjects:	antitumor activity L,L-diphenylalanine Photodynamic therapy porphyrin conjugates reactive oxygen species FF DMSO EDC PyBOP ANS Mw TFA UV–vis porphyrin conjugates DMEM 7-AAD THF CHCl3 HRBCs antitumor activity reactive oxygen species HOBt NHS L,L-diphenylalanine CCK-8 HBTU HATU HBOt HPLC CH2Cl2 DIC PBS Photodynamic therapy DCC ESI-HRMS DIPEA TEA NMR HEPES Annexin V FITC FFOMe
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Summary:	•Synthesis of four novel L,L-diphenylalanine (FF) functionalized porphyrins.•Photophysical studies showing that FF conjugation influences porphyrin aggregation.•Post-irradiation with 650 nm light decreased cell viability of a cervical tumor cell line to 70 %, with no cell death induced without light.•Absence of hemolytic activity and non-toxicity to red blood cells at tested concentrations.•Efficient cellular uptake of peptide-porphyrin compounds, demonstrated by flow cytometry after 4 hours of incubation. Photodynamic therapy (PDT) triggers selective cell death through intensive oxidative stress induced by the generation of reactive species by a photosensitizer (PS) excited by light. In this work, we report the synthesis of four novel porphyrins conjugated to the self-assembling dipeptide L,L-diphenylalanine (FF), effectively inhibiting cervical tumor cell growth. The PS were prepared using the classical A3B strategy, with functionalized and non-functionalized porphyrins obtained in moderate yields over 3 to 4 steps. Absorption and fluorescence studies indicate that the FF attached to the porphyrin ring influences their aggregation at micromolar concentrations. The compounds were efficiently internalized by HeLa cells after 4 h of incubation. Cytotoxicity tests performed in the 1.25–5.0 µmol L−1 range showed that cell viability was reduced to 70 % after irradiation (650 nm). A correlation between cell permeation and the cell death mechanism promoted by the porphyrin was observed. [Display omitted]
ISSN:	0022-2860
DOI:	10.1016/j.molstruc.2024.140545