Fatty Acid Conjugates of Toluidine Blue O as Amphiphilic Photosensitizers: Synthesis, Solubility, Photophysics and Photochemical Properties
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Fecha
2021-01
Profesor/a GuĂa
Facultad/escuela
Idioma
en
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Editor
Blackwell Publishing Inc.
Nombre de Curso
Licencia CC
Licencia CC
Resumen
Toluidine blue O (TBO) is a water-soluble photosensitizer that has been used in photodynamic antimicrobial and anticancer treatments, but suffers from limited solubility in hydrophobic media. In an effort to incrementally increase TBOâs hydrophobicity, we describe the synthesis of hexanoic (TBOC6) and myristic (TBOC14) fatty acid derivatives of TBO formed in low to moderate percent yields by condensation with the free amine site. Covalently linking 6 and 14 carbon chains led to modifications of not only TBOâs solubility, but also its photophysical and photochemical properties. TBOC6 and TBOC14 derivatives were more soluble in organic solvents and showed hypsochromic shifts in their absorption and emission bands. The solubility in phosphate buffer solution was low for both TBOC6 and TBOC14, but unexpectedly slightly greater in the latter. Both TBOC6 and TBOC14 showed decreased triplet excited-state lifetimes and singlet oxygen quantum yields in acetonitrile, which was attributed to heightened aggregation of these conjugates particularly at high concentrations due to the hydrophobic âtails.â While in diluted aqueous buffer solution, indirect measurements showed similar efficiency in singlet oxygen generation for TBOC14 compared to TBO. This work demonstrates a facile synthesis of fatty acid TBO derivatives leading to amphiphilic compounds with a delocalized cationic âheadâ group and hydrophobic âtailsâ for potential to accumulate into biological membranes or membrane/aqueous interfaces in PDT applications.
Notas
IndexaciĂłn: Scopus
Palabras clave
Fatty Acids, Molecular Structure, Photosensitizing Agents, Singlet Oxygen, Spectrometry, Fluorescence, Tolonium Chloride
CitaciĂłn
Photochemistry and Photobiology Volume 97, Issue 1, Pages 71 - 79 January/February 2021
DOI
10.1111/php.13304