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

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Vassiliades, Sandra V. ; Arguello, Karina A. B. ; Castro, Carlos E. ; Silva, Clovis A. ; Gonzalez, Ana Clara ; Homem-de-Mello, Paula ; Nantes, Iseli Lourenco ; Aguilar, Andrea M. ; Barbosa-Reis, Gustavo ; Oliveira-Silva, Diogo ; Giuntini, Francesca ; Alves, Wendel A.

• Tipo de documento: Artigo Científico
• Fonte: Journal of Molecular Structure; v. 1322, p. 13-pg., 2024-11-03.

Resumo

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 nonfunctionalized 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 mu mol 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. (AU)

• Processo FAPESP: 14/50867-3 - INCT 2014: Instituto Nacional de Ciência e Tecnologia de Bioanalítica
• Beneficiário: Marco Aurelio Zezzi Arruda
• Modalidade de apoio: Auxílio à Pesquisa - Temático
• Processo FAPESP: 22/14753-0 - Tecnologias de biossensores e sistemas de liberação controlada baseadas em microagulhas para diagnóstico e tratamento de doenças
• Beneficiário: Wendel Andrade Alves
• Modalidade de apoio: Auxílio à Pesquisa - Temático