Photodynamic Efficiency of Xanthene Dyes and Their Phototoxicity against a Carcinoma Cell Line: A Computational and Experimental Study

Autor(es)

Buck, Suelen T. G. ; Bettanin, Fernanda ; Orestes, Ednilson ; Homem-de-Mello, Paula ; Imasato, Hidetake ; Viana, Rommel B. ; Perussi, Janice R. ; da Silva, Alberico B. F.

• Tipo de documento: Artigo Científico
• Fonte: JOURNAL OF CHEMISTRY; v. 2017, p. 9-pg., 2017-01-01.

Resumo

The aim of this study is to assess the insights of molecular properties of the xanthene dyes [fluorescein (FL), Rose Bengal (RB), erythrosin B (EB), and eosin Y (EY)] to correlate systematically their photodynamic efficiency as well as their phototoxicity against a carcinoma cell line. The phototoxicity was evaluated by comparing the values of the medium inhibitory concentration (IC50) upon HEp-2 cells with the xanthene corresponding photodynamic activity using the uric acid as a chemical dosimeter and their octanol-water partition coefficient (log P). RB was the more cytotoxic dye against HEp-2 cell line and the most efficient photosensitizer in causing photoxidation of uric acid; nevertheless it was the only one characterized as being hydrophobic among the xanthenes studied here. On the other hand, it was observed that the halogen substituents increased the hydrophilicity and photodynamic activity, consistentwith the cytotoxic experiments. Furthermore, the reactivity index parameters, electric dipole moment, molecular volume, and the frontier orbitals were also obtained by the Density Functional Theory (DFT). The lowest dipole moment and highest molecular volume of RB corroborate with its highest hydrophobicity due to heavy atom substituents like halogens, while the halogen substituents did not affect expressively the electronic features at all. (AU)

• Processo FAPESP: 07/05370-0 - Estudo químico-quântico de corantes e de complexos de metais de transição
• Beneficiário: Paula Homem-de-Mello
• Modalidade de apoio: Auxílio à Pesquisa - Jovens Pesquisadores
• Processo FAPESP: 11/09979-4 - Fotoinativação seletiva de microrganismos empregando planejamento experimental
• Beneficiário: Janice Rodrigues Perussi
• Modalidade de apoio: Auxílio à Pesquisa - Regular
• Processo FAPESP: 10/19790-3 - Estudo teórico de porfirinas, ftalocianinas e clorinas com ênfase para aplicação em terapia fotodinâmica
• Beneficiário: Fernanda Bettanin
• Modalidade de apoio: Bolsas no Brasil - Doutorado
• Processo FAPESP: 12/19175-2 - Caracterização de complexos metálicos com aplicação medicinal: uma investigação espectroscópica e químico-quântica
• Beneficiário: Rommel Bezerra Viana
• Modalidade de apoio: Bolsas no Brasil - Pós-Doutorado