Chemical equilibria of Eosin Y and its synthetic ester derivatives in non-ionic and ionic micellar environments
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2021-04-01
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Pellosi, Diogo Silva 
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Eosin (EOS) and its synthetic ester derivatives have adequate properties to be employed as histological markers for and as drugs for photodynamic therapy. However, they present a very complex protolytic and tautomeric equilibrium that reflects on their photophysical properties. Hence their biomedical applications are strongly affected by the medium's pH, charge and hydrophobicity. In this study, we evaluated the effects of two neutral (Pluronic® F-127 and P-123) and two ionic (anionic SDS and cationic CTAB) surfactant micelles as a simple membrane model on the protolytic/tautomeric equilibrium of EOS and its ester derivative dyes. Multivariate analysis based on Q-Imbrie's factor and the K-matrix method on the electronic absorption spectroscopy data in different pH conditions allowed for the understanding of the complex protolytic/tautomeric equilibrium, and the influence of medium microenvironment on the EOS dyes at each pH. Our results demonstrated that, when close to physiological pH (~7.4), and electrostatic attraction towards cationic surfaces favor dyes locating close to the micelle's (biomembrane model) interface, where their biomedical applications are favored. Therefore, the analysis in different environments shows that the interactions of EOS and its derivatives with biomembranes can be modulated based on the hydrophobicity of the xanthene derivative and the cell membrane charge.
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FREITAS, C. F. de; ESTEVÃO, D. S.; PELLOSI, D. S.; SCARMINIO, I. S.; CAETANO, W.; HIOKA, N.; BATISTELA, V. R. Chemical equilibria of Eosin Y and its synthetic ester derivatives in non-ionic and ionic micellar environments. Journal of Molecular Liquids, v. 327, p. 114794, 2021.