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Supramolecular caging for cytosolic delivery of anionic probes.

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.

SUBMITTER: Fernandez-Caro H

PROVIDER: S-EPMC7017865 | biostudies-literature | 2019 Oct

REPOSITORIES: biostudies-literature

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Supramolecular caging for cytosolic delivery of anionic probes.

Fernández-Caro Héctor H Lostalé-Seijo Irene I Martínez-Calvo Miguel M Mosquera Jesús J Mascareñas José L JL Montenegro Javier J

Chemical science 20190820 39

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 ...[more]

PMID: 32110291

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