Person: Rodríguez Agarrabeitia, Antonia
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First Name
Antonia
Last Name
Rodríguez Agarrabeitia
Affiliation
Universidad Complutense de Madrid
Faculty / Institute
Óptica y Optometría
Department
Química Orgánica
Area
Química Orgánica
Identifiers
4 results
Search Results
Now showing 1 - 4 of 4
Item Tailoring the Molecular Skeleton of Aza-BODIPYs to Design Photostable Red-Light-Emitting Laser Dyes(ChemPhotoChem, 2018) Prieto Castañeda, Alejandro; Avellanal Zaballa, Edurne; Gartzia Rivero, Leire; Cerdán Pedraza, Luis; Rodríguez Agarrabeitia, Antonia; García Moreno, Inmaculada; Bañuelos Prieto, Jorge; Ortiz García, María JosefaIn this article the design and characterization of a set of novel red‐light‐emitting laser aza‐BODIPY dyes is reported. The applied synthetic method allows an exhaustive and versatile functionalization of both the dipyrrin core and the boron bridge. From the analysis of the photophysical and laser signatures, we determine the suitable modifications of the chromophoric backbone necessary to modulate the emission spectral region, efficiency and photostability under a strong irradiation regime. These dyes are endowed with efficient fluorescence and laser emission, and are particularly outstanding in terms of their high photostability, a key parameter to guarantee long‐lasting emission in any (bio)technological application. The herein‐reported results support, for the first time, the viability of aza‐BODIPYs as tunable red laser dyes. In fact, the laser performances of some of the tested aza‐BODIPYs surpass those of commercially available laser dyes in the same spectral region.Item Halogen-free photosensitizers based on meso-enamine-BODIPYs for bioimaging and photodynamic therapy(Journal of Materials Chemistry B, 2022) Prieto Montero, Ruth; Díaz Andrés, Aitor; Prieto Castañeda, Alejandro; Tabero Truchado, Andrea; Longarte Aldama, Asier; Rodríguez Agarrabeitia, Antonia; Villanueva Oroquieta, Ángeles; Ortiz García, María Josefa; Montero Santos, Raul; Casanova, David; Martínez Martínez, VirginiaThe search for efficient heavy atom free photosensitizers (PSs) for photodynamic therapy (PDT) is a very active field. We describe herein a simple and easily accessible molecular design based on the attachment of an enamine group as an electron-donor moiety at the meso position of the BODIPY core with different alkylation patterns. The effect of the alkylation degree and solvent polarity on the photophysical properties in terms of splitting absorption bands, fluorescence efficiencies and singlet oxygen production is analyzed in depth experimentally using spectroscopic techniques, including femtosecond and nanosecond transient absorption (fs- and ns-TA) and using computational simulations based on time-dependent density functional theory. The correlation between the theoretical/experimental results permits the rationalization of the observed photophysical behavior exhibited by meso-enamine-BODIPY compounds and the determination of mechanistic details, which rule the population of the triplet state manifold. The potential applicability as a theragnostic agent for the most promising compound is demonstrated through in vitro assays in HeLa cells by analyzing the internalization, localization and phototoxic action.Item FormylBODIPYs by PCC-Promoted Selective Oxidation of α-MethylBODIPYs. Synthetic Versatility and Applications(Organic Letters, 2019) Ramos Torres, Ágata; Avellanal Zaballa, Edurne; Prieto Castañeda, Alejandro; García Garrido, Fernando; Bañuelos Prieto, Jorge; Rodríguez Agarrabeitia, Antonia; Ortiz García, María JosefaAn efficient synthesis of formylBODIPYs has been established based on an oxidation with PCC of 3-methylBODIPYs. It has been demonstrated that this reagent can oxidize methyl groups at such position of the BODIPY core, regardless of its substitution pattern. Moreover, through this procedure it is possible to synthesize 8-aryl-3,5-diformylBODIPYs, which are otherwise difficult to obtain. These precursors have been functionalized to develop fluorescent sensors of amino acids or photosensitizers for singlet oxygen generation.Item Red haloBODIPYs as theragnostic agents: The role of the substitution at meso position(Dyes and Pigments, 2021) Prieto Montero, Ruth; Prieto Castañeda, Alejandro; Katsumiti, Alberto; Sola Llano, Rebeca; Rodríguez Agarrabeitia, Antonia; Cajaraville, Miren P.; Ortiz García, María Josefa; Martínez Martínez, VirginiaThree different molecular designs based on BODIPY dye have been proposed as photosensitizers (PSs) for photodynamic therapy (PDT) by the inclusion of halogen atoms (Iodine) at 2,6-positions and with extended conjugation at 3, 5-positions and varying the substitution at meso position. The synthesis is described and their main photophysical features including singlet oxygen production and triplet states were characterized by absorption and fluorescence spectroscopy (steady-state and time-correlated) and nanosecond transient absorption spectroscopy. The results were compared with the commercial Chlorin e6. The three new red-halogen-BODIPYs showed a great balance between singlet oxygen generation (ΦΔ≥0.40) and fluorescence (Φfl≥0.22) for potential application on PDT, and particularly in theragnosis. In vitro experiments in HeLa cells were done to study their performance and to elucidate the best potential candidate for PDT.