About
Contact
Help
Sending publications
How to publish
Advanced Search
View Item 
  •   Home
  • Facultad de Ciencias Químicas y Farmacéuticas
  • Artículos de revistas
  • View Item
  •   Home
  • Facultad de Ciencias Químicas y Farmacéuticas
  • Artículos de revistas
  • View Item
JavaScript is disabled for your browser. Some features of this site may not work without it.

Browse byCommunities and CollectionsDateAuthorsTitlesSubjectsThis CollectionDateAuthorsTitlesSubjects
Biblioteca Digital - Universidad de Chile
Revistas Chilenas
Repositorios Latinoamericanos
Tesis LatinoAmericanas
Tesis chilenas
Related linksRegistry of Open Access RepositoriesOpenDOARGoogle scholarCOREBASE
My Account
Login to my accountRegister

Fatty acid conjugates of Toluidine Blue O as Amphiphilic Photosensitizers: Synthesis, solubility, photophysics and photochemical properties(dagger)

Artículo
Thumbnail
Open/Download
IconFatty-Acid-Conjugates.pdf (235.2Kb)
Access note
Acceso a solo metadatos
Publication date
2020
Metadata
Show full item record
Cómo citar
Robinson Duggon, José
Cómo citar
Fatty acid conjugates of Toluidine Blue O as Amphiphilic Photosensitizers: Synthesis, solubility, photophysics and photochemical properties(dagger)
.
Copiar
Cerrar
Author
  • Robinson Duggon, José;
  • Pizarro, Nancy;
  • Gunther Sapunar, Germán;
  • Zúñiga Núñez, Daniel;
  • Edwards, Ana María;
  • Greer, Alexander;
  • Fuentealba, Denis;
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.
Patrocinador
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
Indexation
Artículo de publicación ISI
Identifier
URI: https://repositorio.uchile.cl/handle/2250/176878
DOI: 10.1111/php.13304
Quote Item
Photochemistry and Photobiology (2020)
Collections
  • Artículos de revistas
xmlui.footer.title
31 participating institutions
More than 73,000 publications
More than 110,000 topics
More than 75,000 authors
Published in the repository
  • How to publish
  • Definitions
  • Copyright
  • Frequent questions
Documents
  • Dating Guide
  • Thesis authorization
  • Document authorization
  • How to prepare a thesis (PDF)
Services
  • Digital library
  • Chilean academic journals portal
  • Latin American Repository Network
  • Latin American theses
  • Chilean theses
Dirección de Servicios de Información y Bibliotecas (SISIB)
Universidad de Chile

© 2020 DSpace
  • Access my account