Author | dc.contributor.author | Robinson Duggon, José | |
Author | dc.contributor.author | Pizarro, Nancy | |
Author | dc.contributor.author | Gunther Sapunar, Germán | |
Author | dc.contributor.author | Zúñiga Núñez, Daniel | |
Author | dc.contributor.author | Edwards, Ana María | |
Author | dc.contributor.author | Greer, Alexander | |
Author | dc.contributor.author | Fuentealba, Denis | |
Admission date | dc.date.accessioned | 2020-09-28T22:37:58Z | |
Available date | dc.date.available | 2020-09-28T22:37:58Z | |
Publication date | dc.date.issued | 2020 | |
Cita de ítem | dc.identifier.citation | Photochemistry and Photobiology (2020) | es_ES |
Identifier | dc.identifier.other | 10.1111/php.13304 | |
Identifier | dc.identifier.uri | https://repositorio.uchile.cl/handle/2250/176878 | |
Abstract | dc.description.abstract | 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 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_ES |
Patrocinador | dc.description.sponsorship | CONICYT through their FONDECYT research program 1160443 CONICYT/FONDEQUIP/UHPLC-MS/MS EQM 120065 ANID FONDECYT/POSTDOCTORADO 3200403 National Science Foundation (NSF) CHE-1856765 CONICYT/FONDEQUIP/Laser Flash Photolysis EQM160099 CONICYT-PCHA/Doctorado Nacional/2015-21150894 | es_ES |
Lenguage | dc.language.iso | en | es_ES |
Publisher | dc.publisher | Wiley | es_ES |
Source | dc.source | Photochemistry and Photobiology | es_ES |
Keywords | dc.subject | Set model chemistry | es_ES |
Keywords | dc.subject | Photodynamic therapy | es_ES |
Keywords | dc.subject | In-vitro | es_ES |
Keywords | dc.subject | Total energies | es_ES |
Keywords | dc.subject | Cationic dyes | es_ES |
Keywords | dc.subject | Cancer | es_ES |
Keywords | dc.subject | Molecules | es_ES |
Keywords | dc.subject | 2-anthracenecarboxylate | es_ES |
Keywords | dc.subject | Photocyclodimerization | es_ES |
Keywords | dc.subject | Derivatives | es_ES |
Título | dc.title | Fatty acid conjugates of Toluidine Blue O as Amphiphilic Photosensitizers: Synthesis, solubility, photophysics and photochemical properties(dagger) | es_ES |
Document type | dc.type | Artículo de revista | |
dcterms.accessRights | dcterms.accessRights | Acceso a solo metadatos | es_ES |
Cataloguer | uchile.catalogador | ctc | es_ES |
Indexation | uchile.index | Artículo de publicación ISI | es_ES |