Fatty Acid Conjugates of Toluidine Blue O as Amphiphilic Photosensitizers: Synthesis, Solubility, Photophysics and Photochemical Properties

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dc.contributor.authorRobinson-Duggon, José
dc.contributor.authorPizarro, Nancy
dc.contributor.authorGunther, Germán
dc.contributor.authorZúñiga-Núñez, Daniel
dc.contributor.authorEdwards, Ana María
dc.contributor.authorGreer, Alexander
dc.contributor.authorFuentealba, Denis
dc.date.accessioned2023-11-10T17:55:03Z
dc.date.available2023-11-10T17:55:03Z
dc.date.issued2021-01
dc.descriptionIndexación: Scopuses
dc.description.abstractToluidine 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 TBO’s 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 TBO’s 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 “tails.” 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 “head” group and hydrophobic “tails” for potential to accumulate into biological membranes or membrane/aqueous interfaces in PDT applications.es
dc.identifier.citationPhotochemistry and Photobiology Volume 97, Issue 1, Pages 71 - 79 January/February 2021es
dc.identifier.doi10.1111/php.13304en
dc.identifier.issn0031-8655
dc.identifier.urihttps://repositorio.unab.cl/xmlui/handle/ria/53905
dc.language.isoenes
dc.publisherBlackwell Publishing Inc.es
dc.subjectFatty Acidses
dc.subjectMolecular Structurees
dc.subjectPhotosensitizing Agentses
dc.subjectSinglet Oxygenes
dc.subjectSpectrometry, Fluorescencees
dc.subjectTolonium Chloridees
dc.titleFatty Acid Conjugates of Toluidine Blue O as Amphiphilic Photosensitizers: Synthesis, Solubility, Photophysics and Photochemical Propertieses
dc.typeArtículoes
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