Supramolecular caging for cytosolic delivery of anionic probes

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Fernández-Caro, Héctor and Lostalé-Seijo, Irene and Martínez-Calvo, Miguel and Mosquera, Jesús and Mascareñas, José L. and Montenegro, Javier (2019) Supramolecular caging for cytosolic delivery of anionic probes. Chemical Science, 10 (39). pp. 8930-8938. ISSN 2041-6539 (https://doi.org/10.1039/c9sc02906k)

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Abstract

The cytosolic delivery of hydrophilic, anionic molecular probes and therapeutics is a major challenge in chemical biology and medicine. Herein, we describe the design and synthesis of peptide-cage hybrids that allow an efficient supramolecular binding, cell membrane translocation and cytosolic delivery of a number of anionic dyes, including pyranine, carboxyfluorescein and several sulfonate-containing Alexa dyes. This supramolecular caging strategy is successful in different cell lines, and the dynamic carrier mechanism has been validated by U-tube experiments. The high efficiency of the reported approach allowed intracellular pH tracking by exploiting the ratiometric excitation of the pyranine fluorescent probe.

ORCID iDs

Fernández-Caro, Héctor, Lostalé-Seijo, Irene, Martínez-Calvo, Miguel, Mosquera, Jesús ORCID logoORCID: https://orcid.org/0000-0001-6878-4567, Mascareñas, José L. and Montenegro, Javier;
CORE (COnnecting REpositories)