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Huczyński, Adam; Jędrzejczyk, Marta, 2023, "Rate of translocation across lipid bilayer of triphenylphosphonium-linked salinomycin derivatives contributes significantly to their K+/H+ exchange activity on membranes", https://doi.org/10.18150/FOIDGJ, RepOD, V1
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Salinomycin (SAL), a polyether antibiotic exerting K+/H+-exchange on cellular membranes, effectively kills cancer stem cells. A series of cationic triphenylphosphonium (TPP+)-linked SAL derivatives were synthesized aiming to render them mitochondria-targeted. Remarkably, attaching a TPP+ moiety via a triazole linker at the C-20 position of SAL (compound 5) preserved the ion carrier potency of the antibiotic, while analogs with TPP+ linked at the C-1 position of SAL (6, 8) were ineffective. On planar bilayer lipid membranes (BLM), the SAL analogs 6 and 8 exhibited slow electrical current relaxation upon a voltage jump, similar to previously studied alkyl-TPP compounds. However, 5 demonstrated much faster current relaxation, which suggested its high permeability through BLM resulting in its pronounced potency to transport potassium and hydrogen ions across both artificial (liposomal) and mitochondrial membranes. SAL and 5 did not induce a steady-state electrical current through the planar lipid bilayer, thereby confirming that the transport mechanism is the electrically silent K+/H+ exchange. The ion exchange mediated by 5 in energized mitochondria was more active than that caused by SAL, which was apparently due to accumulation of 5 in mitochondria. Thus, compound 5 can be regarded as a promising lead compound for testing anticancer and antimicrobial activity.
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Bilayer lipid membrane, Liposome, Mitochondria
Yuri N. Antonenko, Marta Jędrzejczyk, Tatyana I. Rokitskaya, Ljudmila S. Khailova, Elena A. Kotova, Adam Huczyński, Rate of translocation across lipid bilayer of triphenylphosphonium-linked salinomycin derivatives contributes significantly to their K+/H+ exchange activity on membranes, Bioelectrochemistry, Volume 145, 2022, 108089, ISSN 1567-5394, https://doi.org/10.1016/j.bioelechem.2022.108089 https://www.sciencedirect.com/science/article/pii/S1567539422000408 doi: 10.1016/j.bioelechem.2022.108089
CC BY - Creative Commons Attribution 4.0
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