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lüll Ca(2+) Selective Host Rotaxane Is Highly Toxic Against Prostate Cancer Cells Smithrud DB; Powers L; Lunn J; Abernathy S; Peschka M; Ho SM; Tarapore PACS Med Chem Lett 2017[Feb]; 8 (2): 163-167New therapies are needed to eradicate androgen resistant, prostate cancer. Prostate cancer usually metastasizes to bone where the concentration of calcium is high, making Ca(2+) a promising toxin. Ionophores can deliver metal cations into cells, but are currently too toxic for human use. We synthesized a new rotaxane (CEHR2) that contains a benzyl 15-crown-5 ether as a blocking group to efficiently bind Ca(2+). CEHR2 transfers Ca(2+) from an aqueous solution into CHCl(3) to greater extent than alkali metal cations and Mg(2+). It also transfers Ca(2+) to a greater extent than CEHR1, which is a rotaxane with an 18-crown-6 ether as a blocking group. CEHR2 was more toxic against the prostate cancer cell lines PC-3, 22Rv1, and C4-2 than CEHR1. This project demonstrates that crown ether rotaxanes can be designed to bind a targeted metal cation, and this selective cation association can result in enhanced toxicity.ä |