Preparation of dipyrrins from F-BODIPYs by treatment with methanesulfonic acids

An alternative metal-free soft procedure for the preparation of dipyrrins from F-BODIPYs is reported. The new method makes possible to obtain certain dipyrrin derivatives that were unaccessible from F-BODIPYs to date. To demonstrate the ability of the new procedure, dipyrrins having highly reactive groups, such as chloro, cyano or acetoxyl, have been easily obtained from the corresponding F-BODIPY, which shows the synthetic utility of the reported methodology

Circularly Polarized Luminescence from Simple Organic Molecules

This article aims to show the identity of “circularly polarized luminescent active simple organic molecules” as a new concept in organic chemistry due to the potential interest of these molecules, as availed by the exponentially growing number of research articles related to them. In particular, it describes and highlights the interest and difficulty in developing chiral simple (small and non-aggregated) organic molecules able to emit left- or right-circularly polarized light efficiently, the efforts realized up to now to reach this challenging objective, and the most significant milestones achieved to date. General guidelines for the preparation of these interesting molecules are also presented

A BODIPY-Based Fluorescent Sensor for Amino Acids Bearing Thiol

Herein, we describe the synthetic route to access a red-emitting BODIPY from its α-diformylated precursor. The photophysical signatures of this dye are sensitive to the presence of thiol-containing amino acids (like cysteine, homocysteine, and glutathione) in the surrounding environment. This sensor provides up to three detection channels to monitor and quantify these biomolecules, even at low concentrations (down to micromolar). Moreover, owing to the pronounced splitting of the spectral band profile induced by these amino acids, the detection can be visualized following just the evolution of the fluorescence color by the naked eye

Functionalization of photosensitized silica nanoparticles for advanced photodynamic therapy of cancer

BODIPY dyes have recently attracted attention as potential photosensitizers. In this work, commercial and novel photosensitizers (PSs) based on BODIPY chromophores (haloBODIPYs and orthogonal dimers strategically designed with intense bands in the blue, green or red region of the visible spectra and high singlet oxygen production) were covalently linked to mesoporous silica nanoparticles (MSNs) further functionalized with PEG and folic acid (FA). MSNs approximately 50 nm in size with different functional groups were synthesized to allow multiple alternatives of PS-PEG-FA decoration of their external surface. Different combinations varying the type of PS (commercial Rose Bengal, Thionine and Chlorine e6 or custom-made BODIPY-based), the linkage design, and the length of PEG are detailed. All the nanosystems were physicochemically characterized (morphology, diameter, size distribution and PS loaded amount) and photophysically studied (absorption capacity, fluorescence efficiency, and singlet oxygen production) in suspension. For the most promising PS-PEG-FA silica nanoplatforms, the biocompatibility in dark conditions and the phototoxicity under suitable irradiation wavelengths (blue, green, or red) at regulated light doses (10–15 J/cm2) were compared with PSs free in solution in HeLa cells in vitro

Del laboratorio al aula virtual en las prácticas de Química Orgánica

Este proyecto surge de la necesidad de proporcionar a los estudiantes la posibilidad de adquirir las competencias asociadas a las prácticas de laboratorio de Química Orgánica, también en aquellas situaciones en las que no es posible la docencia presencial. Un claro ejemplo de ello ha sido el año 2020 con la situación del COVID-19 y el obligado confinamiento, que ha hecho imposible proporcionar a los estudiantes docencia práctica en el laboratorio. Pero esta no es la única situación en la que la posibilidad de recibir docencia práctica online se hace necesaria. Pueden existir casos de estudiantes que no puedan asistir presencialmente al laboratorio, por ejemplo, por motivos médicos, psicológicos, por discapacidad, cuando no se dispone de un laboratorio convenientemente adaptado, etc. La docencia online tiene la ventaja, frente a la docencia presencial, que se puede recibir desde cualquier lugar, de manera no necesariamente síncrona. Esto facilita que los estudiantes puedan organizar su docencia adaptada a su situación y necesidades. Así, en este proyecto se proporcionan las herramientas para posibilitar que todos los estudiantes puedan recibir esta docencia en cualquier situación, momento y lugar. Es evidente el reto que supone adaptar una docencia práctica de laboratorio a la docencia online, donde no es posible la manipulación de reactivos y material que se trabaja en un laboratorio de prácticas. Por ello, en este proyecto se han diseñado las actividades online que han de sustituir a la docencia presencial en el laboratorio, de manera que se logre la adquisición de las competencias asociadas a las prácticas por parte de la totalidad de los estudiantes, así como su correcta evaluación

Red haloBODIPYs as theragnostic agents: The role of the substitution at meso position

Three 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

Exploring BODIPY Derivatives as Singlet Oxygen Photosensitizers for PDT

This minireview is devoted to honoring the memory of Dr. Thomas Dougherty, a pioneer of modern photodynamic therapy (PDT). It compiles the most important inputs made by our research group since 2012 in the development of new photosensitizers based on BODIPY chromophore which, thanks to the rich BODIPY chemistry, allows a finely tuned design of the photophysical properties of this family of dyes to serve as efficient photosensitizers for the generation of singlet oxygen. These two factors, photophysical tuning and workable chemistry, have turned BODIPY chromophore as one of the most promising dyes for the development of improved photosensitizers for PDT. In this line, this minireview is mainly related to the establishment of chemical methods and structural designs for enabling efficient singlet oxygen generation in BODIPYs. The approaches include the incorporation of heavy atoms, such as halogens (iodine or bromine) in different number and positions on the BODIPY scaffold, and also transition metal atoms, by their complexation with Ir(III) center, for instance. On the other hand, low‐toxicity approaches, without involving heavy metals, have been developed by preparing several orthogonal BODIPY dimers with different substitution patterns. The advantages and drawbacks of all these diverse molecular designs based on BODIPY structural framework are described

Preparación de material de estudio y reflexión para la página web de la asignatura «Ampliación de Química Orgánica»

El objetivo principal de esta comunicación es mostrar parte del material que se está desarrollando para la página web de la asignatura virtual «Ampliación de Química Orgánica» (tercer curso), de la Licenciatura de Química de la Universidad Complutense de Madrid

Nuevos O-BODIPYs como láseres de colorante

La presente invención se refiere a unos nuevos colorantes con estructura de Bodipy caracterizados porque se han remplazado los átomos de flúor presentes en los BODIPYs convencionales por grupos acetoxi, trifluoroacetoxi o ariloxi, a su uso como colorantes láser y como marcadores fluorescentes y a un procedimiento de obtención de algunos de estos compuestosPeer reviewedUniversidad Complutense de MadridB2 Patente con examen previ

Nuevos O-BODIPYs como láseres de colorante

La presente invención se refiere a unos nuevos colorantes con estructura de BODIPY caracterizados porque se han remplazado los átomos de flúor presentes en los BODIPYs convencionales por grupos acetoxi, trifluoroacetoxi o ariloxi, a su uso como colorantes láser y como marcadores fluorescentes y a un procedimiento de obtención de algunos de estos compuestosPeer reviewedUniversidad Complutense de Madrid, Consejo Superior de Investigaciones CientíficasA1 Solicitud de patente con informe sobre el estado de la técnic