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3. A highly fluorescent and readily accessible all-organic photosensitizer model for advancing image-guided cancer PDT.

Author

Garcia-Sampedro, Andres, Prieto-Castañeda, Alejandro, Agarrabeitia, Antonia R., Bañuelos, Jorge, García-Moreno, Inmaculada, Villanueva, Angeles, de la Moya, Santiago, Ortiz, María J., and Acedo, Pilar

Abstract

The potential of using image-guided photodynamic therapy (ig-PDT) for cancer, especially with highly biocompatible fluorescent agents free of heavy atoms, is well recognized. This is due to key advantages related to minimizing adverse side effects associated with standard cancer chemotherapy. However, this theragnostic approach is strongly limited by the lack of synthetically-accessible and easily-modulable chemical scaffolds, enabling the rapid design and construction of advanced agents for clinical ig-PDT. In fact, there are still very few ig-PDT agents clinically approved. Herein we report a readily accessible, easy-tunable and highly fluorescent all-organic small photosensitizer, as a model design for accelerating the development and translation of advanced ig-PDT agents for cancer. This scaffold is based on BODIPY, which assures high fluorescence, accessibility, and ease of performance adaptation by workable chemistry. The optimal PDT performance of this BODIPY dye, tested in highly resistant pancreatic cancer cells, despite its high fluorescent behavior, maintained even after fixation and cancer cell death, is based on its selective accumulation in mitochondria. This induces apoptosis upon illumination, as evidenced by proteomic studies and flow cytometry. All these characteristics make the reported BODIPY-based fluorescent photosensitizer a valuable model for the rapid development of ig-PDT agents for clinical use. [ABSTRACT FROM AUTHOR]

Published
2024
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5. Halogen-free photosensitizers based on meso-enamine-BODIPYs for bioimaging and photodynamic therapy

Author

Prieto-Montero, Ruth, primary, Díaz Andres, Aitor, additional, Prieto-Castañeda, Alejandro, additional, Tabero, Andrea, additional, Longarte, Asier, additional, Agarrabeitia, Antonia R., additional, Villanueva, Angeles, additional, Ortiz, María J., additional, Montero, Raúl, additional, Casanova, David, additional, and Martínez-Martínez, Virginia, additional

Published
2023
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6. Development of Geometry-Controlled All-Orthogonal BODIPY Trimers for Photodynamic Therapy and Phototheragnosis

Author

Prieto-Castañeda, Alejandro, primary, García-Garrido, Fernando, additional, Díaz-Norambuena, Carolina, additional, Escriche-Navarro, Blanca, additional, García-Fernández, Alba, additional, Bañuelos, Jorge, additional, Rebollar, Esther, additional, García-Moreno, Inmaculada, additional, Martínez-Máñez, Ramón, additional, de la Moya, Santiago, additional, Agarrabeitia, Antonia R., additional, and Ortiz, María J., additional

Published
2022
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9. Mitochondria selective trackers for long-term imaging based on readily accessible neutral BODIPYs

Author

Ramos-Torres, Ágata, primary, Avellanal-Zaballa, Edurne, additional, García-Garrido, Fernando, additional, Fernández-Martínez, Ana B., additional, Prieto-Castañeda, Alejandro, additional, Agarrabeitia, Antonia R., additional, Bañuelos, Jorge, additional, García-Moreno, Inmaculada, additional, Lucio-Cazaña, Francisco-Javier, additional, and Ortiz, María J., additional

Published
2021
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11. Nuevos complejos dipirrometénicos como plataformas versátiles para aplicaciones ópticas y/o biomédicas

Author

Prieto Castañeda, Alejandro and Prieto Castañeda, Alejandro

Abstract

La Tesis consta de una introducción general, con un resumen de los antecedentes más relevantes relacionados con el tema, así como los objetivos planteados en este trabajo. A continuación, se recogen en tres capítulos los aspectos clave desarrollados para conseguir dichos objetivos y se completa con un capítulo de conclusiones generales, otro donde se detalla la parte experimental realizada y, finalmente, un capítulo de bibliografía. En primer lugar, se presenta a los dipirrometenos (o dipirrinas) como valiosos intermedios para la obtención de diferentes tipos de sistemas, haciendo un breve resumen de su estructura, síntesis y funcionalización. Seguidamente, se presentan los dos tipos de complejos dipirrometénicos que constituyen el objetivo principal de este trabajo. Se inicia el estudio con la síntesis de derivados de la familia de los aza-BODIPYs para su aplicación como láseres de colorante y cassettes de transferencia de energía en la zona roja del espectro. Estos compuestos presentan absorción y emisión en esta zona y se encuentran prácticamente inexplorados en las aplicaciones mencionadas...

Published
2020

13. Exploring BODIPY Derivatives as Singlet Oxygen Photosensitizers for PDT

Author

Prieto‐Montero, Ruth, primary, Prieto‐Castañeda, Alejandro, additional, Sola‐Llano, Rebeca, additional, Agarrabeitia, Antonia R., additional, García‐Fresnadillo, David, additional, López‐Arbeloa, Iñigo, additional, Villanueva, Angeles, additional, Ortiz, María J., additional, Moya, Santiago, additional, and Martínez‐Martínez, Virginia, additional

Published
2020
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20. Exploring BODIPY meso-enamines as singlet-oxygen photosensitizers for PDT

Author

Ortiz, Maria J., primary, Agarrabeitia, Antonia R., primary, Palao, Eduardo, additional, Prieto-Moreno, Ruth, additional, Epelde-Elezcano, Nerea, additional, Moreno, Florencio, additional, Martinez-Martinez, Virginia, additional, de la Moya, Santiago, additional, Prieto-Castañeda, Alejandro, additional, and Maroto, Beatriz L., additional

Published
2017
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21. Rational Design of Advanced Photosensitizers Based on Orthogonal BODIPY Dimers to Finely Modulate Singlet Oxygen Generation

Author

Epelde‐Elezcano, Nerea, primary, Palao, Eduardo, additional, Manzano, Hegoi, additional, Prieto‐Castañeda, Alejandro, additional, Agarrabeitia, Antonia R., additional, Tabero, Andrea, additional, Villanueva, Angeles, additional, de la Moya, Santiago, additional, López‐Arbeloa, Íñigo, additional, Martínez‐Martínez, Virginia, additional, and Ortiz, María J., additional

Published
2017
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22. Adapting BODIPYs to singlet oxygen production on silica nanoparticles

Author

Epelde-Elezcano, Nerea, primary, Prieto-Montero, Ruth, additional, Martínez-Martínez, Virginia, additional, Ortiz, María J., additional, Prieto-Castañeda, Alejandro, additional, Peña-Cabrera, Eduardo, additional, Belmonte-Vázquez, José L., additional, López-Arbeloa, Iñigo, additional, Brown, Ross, additional, and Lacombe, Sylvie, additional

Published
2017
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23. Halogen-free photosensitizers based on meso -enamine-BODIPYs for bioimaging and photodynamic therapy.

Author

Prieto-Montero R, Díaz Andres A, Prieto-Castañeda A, Tabero A, Longarte A, Agarrabeitia AR, Villanueva A, Ortiz MJ, Montero R, Casanova D, and Martínez-Martínez V

Subjects
Humans, HeLa Cells, Halogens, Photosensitizing Agents pharmacology, Photosensitizing Agents chemistry, Photochemotherapy
Abstract

The 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.

Published
2022
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24. Red/NIR Thermally Activated Delayed Fluorescence from Aza-BODIPYs.

Author

Avellanal-Zaballa E, Prieto-Castañeda A, García-Garrido F, Agarrabeitia AR, Rebollar E, Bañuelos J, García-Moreno I, and Ortiz MJ

Abstract

The search for long-lived red and NIR fluorescent dyes is challenging and hitherto scarcely reported. Herein, the viability of aza-BODIPY skeleton as a promising system for achieving thermal activated delayed fluorescent (TADF) probes emitting in this target region is demonstrated for the first time. The synthetic versatility of this scaffold allows the design of energy and charge transfer cassettes modulating the stereoelectronic properties of the energy donors, the spacer moieties and the linkage positions. Delayed emission from these architectures is recorded in the red spectral region (695-735 nm) with lifetimes longer than 100 μs in aerated solutions at room temperature. The computational-aided photophysical study under mild and hard irradiation regimes disclose the interplay between molecular structure and photonic performance to develop long-lived fluorescence red emitters through thermally activated reverse intersystem crossing. The efficient and long-lasting NIR emission of the newly synthesized aza-BODIPY systems provides a basis to develop advanced optical materials with exciting and appealing photonic response., (© 2020 Wiley-VCH GmbH.)

Published
2020
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25. Rational Design of Advanced Photosensitizers Based on Orthogonal BODIPY Dimers to Finely Modulate Singlet Oxygen Generation.

Author

Epelde-Elezcano N, Palao E, Manzano H, Prieto-Castañeda A, Agarrabeitia AR, Tabero A, Villanueva A, de la Moya S, López-Arbeloa Í, Martínez-Martínez V, and Ortiz MJ

Abstract

The synthesis, photophysical characterization, and modeling of a new library of halogen-free photosensitizers (PS) based on orthogonal boron dipyrromethene (BODIPY) dimers are reported. Herein we establish key structural factors in order to enhance singlet oxygen generation by judiciously choosing the substitution patterns according to key electronic effects and synthetic accessibility factors. The photosensitization mechanism of orthogonal BODIPY dimers is demonstrated to be strongly related to their intrinsic intramolecular charge transfer (ICT) character through the spin-orbit charge-transfer intersystem crossing (SOCT-ISC) mechanism. Thus, singlet oxygen generation can be effectively modulated through the solvent polarity and the presence of electron-donating or withdrawing groups in one of the BODIPY units. The photodynamic therapy (PDT) activity is demonstrated by in vitro experiments, showing that selected photosensitizers are efficiently internalized into HeLa cells, exhibiting low dark toxicity and high phototoxicity, even at low PS concentration (0.05-5×10 -6  m)., (© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)

Published
2017
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