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2.B.90.  The Pseudo-Peptidic Cage-Anion Carrier (PPC-AC) Family

Tapia et al. 2019 explored small pseudopeptidic cages 114 (see figure below) which behave as HCl transporters. The nature of the amino acid side chain is key for the transport activity with compound 114c bearing fluorinated phenyl groups as the most active. Using deuterated DPC-micelles efficient internalization of chloride under acidic conditions was demonstrated. The cytotoxicity of the compounds was explored in A549 cells under different external pH conditions. It was found that the toxicity of 114c increased five-fold at acidic pH with IC50 values of 166, 28 and 29 μM for pH 7.6, 7.2 and 6.2, respectively.

Pseudopeptidic cages 114a–e.

References associated with 2.B.90 family:

Tapia, L., Y. Pérez, M. Bolte, J. Casas, J. Solà, R. Quesada, and I. Alfonso. (2019). pH-Dependent Chloride Transport by Pseudopeptidic Cages for the Selective Killing of Cancer Cells in Acidic Microenvironments. Angew Chem Int Ed Engl 58: 12465-12468. 31298461