作者: Yasuhara, Kazuma ; Louis, Marine ; Martin, Colin J. ; Harada, Daiyu ; Allain, Clémence ; Ferrer, Magin Benedict ; Kawaguchi, Noriaki ; Nakatani, Keitaro ; Métivier, Rémi ; Kawai, Tsuyoshi ; Yanagida, Takayuki

Certain derivatives of terarylene are able to undergo a highly efficient oxidative cycloreversion cascade effect, a ring opening reaction with quantum yields above unity, resulting in a colored-to-colorless transition in solution. In the presence of chloroform, high-energy UV and X-rays can trigger this phenomenon, potentially acting as a visual detection system for ionizing radiation. However, chloroform is sensitive to different irradiation wavelengths without distinction, making it difficult to adapt to a reusable device. Chlorobenzene was chosen as an alternative halogenated solvent, as it offers wavelength selectivity between photocyclization and cascade effect cycloreversion. Nile Red was also incorporated into the system with the aim of improving the sensitivity of the visual detection via fluorescence photoswitching. Finally, microencapsulation of both terarylene and Nile Red was targeted to obtain both the cascade effect and photoswitching in a single system. In microcapsules made from a Pickering emulsion, this terarylene-Nile Red system showed high fatigue resistance to repeated photocyclization and cycloreversion irradiation, giving access to repeated ON/OFF fluorescence photoswitching. The cascade effect was also successfully demonstrated along with fluorescence recovery, showing the versatility of the two phenomena in different media.

2024-09-01·Journal of Hazardous Materials

Fluorescent labeling of micro/nanoplastics for biological applications with a focus on “true-to-life" tracking

Article

作者: Cazorla-Ares, Camila ; Mejia-Carmona, Karen ; Arribas Arranz, Jéssica ; Marcos, Ricard ; Vela, Lourdes ; Valido, Iris H ; Pastor, Susana ; Hernández, Alba ; Velázquez, Antonia ; Villacorta, Aliro ; Morataya-Reyes, Michelle ; López-Mesas, Montserrat ; Fuentes-Cebrian, Victor ; Carrillo-Navarrete, Fernando

The increased environmental presence of micro-/nanoplastics (MNPLs) and the potential health risks associated with their exposure classify them as environmental pollutants with special environmental and health concerns. Consequently, there is an urgent need to investigate the potential risks associated with secondary MNPLs. In this context, using "true-to-life" MNPLs, resulting from the laboratory degradation of plastic goods, may be a sound approach. These non-commercial secondary MNPLs must be labeled to track their presence/journeys inside cells or organisms. Because the cell internalization of MNPLs is commonly analyzed using fluorescence techniques, the use of fluorescent dyes may be a sound method to label them. Five different compounds comprising two chemical dyes (Nile Red and Rhodamine-B), one optical brightener (Opticol), and two industrial dyes (Amarillo Luminoso and iDye PolyPink) were tested to determine their potential for such applications. Using commercial standards of polystyrene nanoplastics (PSNPLs) with an average size of 170 nm, different characteristics of the selected dyes such as the absence of impact on cell viability, specificity for plastic staining, no leaching, and lack of interference with other fluorochromes were analyzed. Based on the overall data obtained in the wide battery of assays performed, iDye PolyPink exhibited the most advantages, with respect to the other compounds, and was selected to effectively label "true-to-life" MNPLs. These advantages were confirmed using a proposed protocol, and labeling titanium-doped PETNPLs (obtained from the degradation of milk PET plastic bottles), as an example of "true-to-life" secondary NPLs. These results confirmed the usefulness of iDye PolyPink for labeling MNPLs and detecting cell internalization.

2024-08-13·Analytical Chemistry

Push–Pull Fluorescent Dyes with Trifluoroacetyl Acceptor for High-Fidelity Sensing of Polarity and Heterogeneity of Lipid Droplets

Article

作者: Aknine, Nathan ; Klymchenko, Andrey S

Imaging and sensing of lipid droplets (LDs) attracted significant attention due to growing evidence for their important role in cell life. Solvatochromic dyes are promising tools to probe LDs' local polarity, but this analysis is biased by their non-negligible emission from intracellular membranes and capacity to emit from both the apolar core and polar interface of LDs. Here, we developed two push-pull solvatochromic dyes based on naphthalene and fluorene cores bearing an exceptionally strong electron acceptor, the trifluoroacetyl group. The latter was found to boost the optical properties of the dyes by shifting their absorption and emission to red and increasing their extinction coefficient, photostability, and sensitivity to solvent polarity (solvatochromism). In contrast to classical solvatochromic dyes, such as parent aldehydes and reference Nile Red, the new dyes exhibited strong fluorescence quenching by millimolar water concentrations in organic solvents. In live cells, the trifluoroacetyl dyes exhibited high specificity to LDs, whereas the parent aldehydes and Nile Red showed a detectable backgrounds from intracellular membranes. Experiments in model lipid membranes and nanoemulsion droplets confirmed the high selectivity of new probes to LDs in contrast to classical solvatochromic dyes. Moreover, the new probes were found to be selective to the LDs oil core, where they can sense lipid unsaturation and chain length. Their ratiometric imaging in cells revealed strong heterogeneity in polarity within LDs, which covered the range of polarities of unsaturated triglyceride oils, whereas Nile Red failed to properly estimate the local polarity of LDs. Finally, the probes revealed that LDs core polarity can be altered by fatty acid diets, which correlates with their chain length and unsaturation.

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