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. 2018 Jan 12;8:607. doi: 10.1038/s41598-017-18747-3

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© The Author(s) 2018

Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.

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Fluorinated derivatives of 4-AP. (A) Compounds tested in this study: (1) 4-aminopyridine. (2) 3,4-diaminopyridine. (3) 3-hydroxymethyl-4-aminopyridine. (4) 3-fluoro-4-aminopyridine. (5) 3-fluoromethyl-4-aminopyridine. (6) 3-fluoroethyl-4-aminopyridine. (7) 2-fluoro-4-aminopyridine. (B) Drug binding to K⁺ channels expressed in frog oocytes: K⁺ currents were generated by a series of 50 ms pulses from −70 mV to +40 mV in increments of 10 mV in the presence of cumulative concentrations of 4-AP derivatives. Each panel represents the K⁺ current recorded from the same oocyte before and after addition of each drug. Scale bar: 1 μA/10 ms. (C) Relative K⁺ current vs. concentration for each drug obtained at +20 mV. (D) Half-maximal inhibitory concentration of each molecule and 95% confidence interval obtained from fitting the data to the Hill equation. n = number of times each drug was tested in separate oocytes. (E) Drug binding to K⁺ channels in explanted mouse optic nerves: compound action potential (CAP) traces before (solid line) and after (dashed line) addition of each drug. Scale bar: 5 mV/5 ms. (F) Relative increase of maximum CAP amplitude vs. concentration for each drug. Amplitude was normalized to the amplitude before the drug. (G) Half-maximal effective concentration of each molecule and 95% confidence interval obtained from fitting the data to the Hill equation. n = number of times each drug was tested in separate nerves.