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Title

pH-Dependent Chloride Transport by Pseudopeptidic Cages for the Selective Killing of Cancer Cells in Acidic Microenvironments

AuthorsTapia, Lucía; Pérez, Yolanda ; Bolte, Michael; Casas, Josefina ; Solà Oller, Jordi ; Quesada, Roberto; Alfonso, Ignacio
KeywordsAnionophores
Cancer
Host–guest systems
NMR spectroscopy
Supramolecular chemistry
Issue Date12-Jul-2019
PublisherWiley-Blackwell
CitationAngewandte Chemie - International Edition 58 (36): 12465-12468 (2019)
AbstractAcidic microenvironments in solid tumors are a hallmark of cancer. Inspired by that, we designed a family of pseudopeptidic cage-like anionophores displaying pH-dependent activity. When protonated, they efficiently bind chloride anions. They also transport chloride through lipid bilayers, with their anionophoric properties improving at acidic pH, suggesting an H+/Cl− symport mechanism. NMR studies in DPC micelles demonstrate that the cages bind chloride within the lipid phase. The chloride affinity and the chloride-exchange rate with the aqueous bulk solution are improved when the pH is lowered. This increases cytotoxicity towards lung adenocarcinoma cells at the pH of the microenvironment of a solid tumor. These properties depend on the nature of the amino-acid side chains of the cages, which modulate their lipophilicity and interactions with the cell membrane. This paves the way towards using pH as a parameter to control the selectivity of cytotoxic ionophores as anticancer drugs. © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Publisher version (URL)https://doi.org/10.1002/anie.201905965
URIhttp://hdl.handle.net/10261/189728
DOIhttp://dx.doi.org/10.1002/anie.201905965
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