World Journal of Chemical Education
ISSN (Print): 2375-1665 ISSN (Online): 2375-1657 Website: https://www.sciepub.com/journal/wjce Editor-in-chief: Prof. V. Jagannadham
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World Journal of Chemical Education. 2026, 14(1), 18-25
DOI: 10.12691/wjce-14-1-3
Open AccessArticle

Mimicking Nature – Imitating Ion Carriers Using Crown Ethers in a Vertical Pressman Cell

Philipp Meyer1, , Stefan Kubik2 and Amitabh Banerji1

1Department of Chemistry - Chemistry Education, University of Potsdam, Potsdam, Germany

2Department of Chemistry – Organic Chemistry, RPTU University Kaiserslautern-Landau, Kaiserslautern, Germany

Pub. Date: March 29, 2026

Cite this paper:
Philipp Meyer, Stefan Kubik and Amitabh Banerji. Mimicking Nature – Imitating Ion Carriers Using Crown Ethers in a Vertical Pressman Cell. World Journal of Chemical Education. 2026; 14(1):18-25. doi: 10.12691/wjce-14-1-3

Abstract

Valinomycin, an antibiotic ionophore (ion carrier), is a functional analog of the cyclic hexaether [18] crown-6 (18C6). Both valinomycin and 18C6 molecules form lipophilic complexes with alkali metal ions. Hence, upon addition of valinomycin or 18C6, alkali metal salts become soluble in non-polar organic solvents. The ability to complex cations allows valinomycin molecules to transport these ions across cell membranes. Since 18C6 molecules bind alkali metal cations in a similar way, by wrapping them in a “greasy coat”, cell transport processes by valinomycin can be imitated using the more cost-efficient and less hazardous 18C6. In a simple test tube experiment, cell conditions are mimicked by means of a triphasic system consisting of an aqueous magnesium sulfate (MgSO4) solution (bottom phase) and an aqueous potassium permanganate (KMnO4) solution (top phase) which are separated by a methyl benzoate phase serving as a liquid membrane. If a solution of 18C6 is injected into the methyl benzoate phase of this “vertical Pressman cell”, a salt transfer from the upper aqueous phase to the bottom phase can be observed, modelling the effect of valinomycin in living cells. Appropriate simplifications for use in schools are discussed and animations are provided to illustrate the ionophore-facilitated cell transport.

Keywords:
high school organic chemistry hands-on learning crown ethers ionophores/ ion carriers membranes

Creative CommonsThis work is licensed under a Creative Commons Attribution 4.0 International License. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/

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References:

[1]  F. Vögtle, E. Weber, Host Guest Complex Chemistry / Macrocycles. Berlin, Heidelberg: Springer Berlin Heidelberg, 1985.
 
[2]  C. J. Pedersen, „The Discovery of Crown Ethers (Noble Lecture)“, Angew. Chem. Int. Ed. Engl., 27(8), 1021–1027, Aug. 1988.
 
[3]  J. F. Stoddart, „Introduction to Macrocycle Chemistry“, in Crown Ethers and Cryptands, The Royal Society of Chemistry, 1991, 1–21.
 
[4]  C. J. Pedersen, H. K. Frensdorff, „Macrocyclic Polyethers and Their Complexes“, Angew. Chem. Int. Ed. Engl., 11(1), 16–25, Jan. 1972.
 
[5]  L. Fabbrizzi, „The origins of the coordination chemistry of alkali metal ions“, ChemTexts, 6 (2), Jun. 2020.
 
[6]  F. Vögtle, „Wirt/Gast-Chemie mit Kationen und Anionen“, in Supramolekulare Chemie, in Teubner Studienbücher Chemie, Wiesbaden: Vieweg+Teubner Verlag, 1992, 23–167.
 
[7]  S. Kubik, Supramolecular Chemistry: From Concepts to Applications; 2. Ed., De Gruyter: Berlin, 2024.
 
[8]  P. Meyer, A. Banerji, "Macrocycles in the Classroom. Making Biochemical Processes Understandable with the Help of Crown Ethers"14th “New Perspectives in Science Education - International Conference”, New Perspectives in Science Education. IT: Filodiritto Editore - Pixel Associazione, Mar. 2025.
 
[9]  https://www.nobelprize.org/prizes/chemistry/1987/summary/ [accessed, Jan. 20th 2026].
 
[10]  J. Lehn, „Supramolecular Chemistry—Scope and Perspectives Molecules, Supermolecules, and Molecular Devices (Nobel Lecture)“, Angew. Chem. Int. Ed. Engl., 27(1), 89–112, Jan. 1988.
 
[11]  J. W. Steed, D. R. Turner, K. J. Wallace, Core concepts in supramolecular chemistry and nanochemistry. Chichester: J. Wiley & sons, 2007.
 
[12]  S. Huang, Y. Liu, W.-Q. Liu, P. Neubauer, und J. Li, „The Nonribosomal Peptide Valinomycin: From Discovery to Bioactivity and Biosynthesis“, Microorganisms, 9 (4), 780, Apr. 2021.
 
[13]  H. Brockmann, G. Schmidt‐Kastner, „Valinomycin I, XXVII. Mitteil. über Antibiotica aus Actinomyceten“, Chem. Ber., 88 (1), 57–61, Jan. 1955.
 
[14]  B. C. Pressman, E. J. Harris, W. S. Jagger, J. H. Johnson, „Antibiotic-mediated transport of alkali ions across lipid barriers.“, Proc. Natl. Acad. Sci. U.S.A., 58 (5), 1949–1956, Nov. 1967.
 
[15]  M. Sulik, R. Graniczny, J. Janczak, D. Kłopotowska, J. Wietrzyk, A. Huczyński, „From Pseudocyclic to Macrocyclic Ionophores: Strategies toward the Synthesis of Cyclic Monensin Derivatives“, J. Org. Chem., 90 (3), 1344–1353, Jan. 2025.
 
[16]  M. Antoszczak, „A comprehensive review of salinomycin derivatives as potent anticancer and anti-CSCs agents“, European Journal of Medicinal Chemistry, 166, 48–64, March 2019.
 
[17]  W. Monden, G. Kosmann, H. Harder, „Zur Permeation von Ionen durch Biomembranen“, Unterricht Biologie, 46 (4), 40–43, 1980.
 
[18]  P. Y. Bruice, Organische Chemie: Studieren kompakt, 5., Aktualisierte Auflage. in Always learning. München: Pearson Studium, 2011.
 
[19]  C. J. Pedersen, „SYNTHETIC MULTIDENTATE MACROCYCLIC COMPOUNDS“, in Synthetic Multidentate Macrocyclic Compounds, Elsevier, 1978, 1–51.
 
[20]  L. Sessa, S. Concilio, F. Marrafino, A. Sarkar, R. Diana, S. Piotto, „Theoretical investigation of hydroxylated analogues of valinomycin as potassium transporter“, Computational Biology and Chemistry, 106, 107936, Oct. 2023.
 
[21]  F. Ullah, T.A. Khan, J. Iltaf; S. Anwar, M.F.A. Khan, M.R. Khan, S. Ullah, M. Fayyaz ur Rehman, M. Mustaqeem, K. Kotwica-Mojzych et. al. „Heterocyclic Crown Ethers with Potential Biological and Pharmacological Properties: From Synthesis to Applications“, Applied Sciences, 12 (3), 1102, Jan. 2022.
 
[22]  J. D. Lamb, J. J. Christensen, R. M. Izatt, „Experimenting with liquid membranes“, J. Chem. Educ., 57(3), 227, Mar. 1980.
 
[23]  D. H. Haynes und B. C. Pressman, „Two-phase partition studies of alkali cation complexation by ionophores“, J. Membrain Biol., 18 (1), 1–21, Dec. 1974.
 
[24]  B. C. Pressman, „Ionophorous antibiotics as models for biological transport“, Fed Proc, 27 (6), 1283–1288, 1968.
 
[25]  R. Ashton, L. K. Steinrauf, „Thermodynamic consideration of the ion transporting antibiotics“, Journal of Molecular Biology, 49 (3), 547–556, May 1970.
 
[26]  G. W. Gokel, S. Negin, M.R. Cantwell, „Crown Ethers“, in Comprehensive Supramolecular Chemistry II, Elsevier, 2017, 3–48.
 
[27]  R. D. Dyson, Cell biology: a molecular approach, 2. ed. Boston: Allyn and Bacon, 1978.
 
[28]  B. C. Pressman, N. T. De Guzman, „NEW IONOPHORES FOR OLD ORGANELLES*“, Annals of the New York Academy of Sciences, 227 (1), 380–391, Feb. 1974.
 
[29]  M. Kirch, J. Lehn, „Selective Transport of Alkali Metal Cations through a Liquid Membrane by Macrobicyclic Carriers“, Angew. Chem. Int. Ed. Engl., 14 (8), 555–556, Aug. 1975.
 
[30]  C. F. Reusch, E. L. Cussler, „Selective membrane transport“, AIChE Journal, 19 (4), 736–741, Jul. 1973.
 
[31]  „Valinomycin, Sigma Aldrich“.
 
[32]  J. Friedrich; M. Oetken, „Modellexperimente zum Durchtritt von Ionen durch eine Biomembran“, Praxis der Naturwissenschaften - Chemie in der Schule, 62 (8), 29–34, 2013.
 
[33]  P. Meyer, A. Banerji, „Wie Kationen Zellwände durchdringen“, Nachr Chem, 72 (7–8), 28–32, Jul. 2024.
 
[34]  Md. M. Mostafiz, E. Hassan, K.-Y. Lee, „Methyl Benzoate as a Promising, Environmentally Safe Insecticide: Current Status and Future Perspectives“, Agriculture, 12 (3), 378, Mar. 2022.
 
[35]  H. J. Bader, H. Schmidtkunz, „Das Experiment im Chemieunterricht“, in Konkrete Fachdidaktik Chemie, Neubearb., 3. ed., P. Pfeifer, B. Lutz, und H. J. Bader, Hrsg., München: Oldenbourg, 2002.
 
[36]  A. Banerji, A. Schönbein, J. Wolff, „OLED Reloaded: Die Synthese des Halbleiterpolymers MEH‐PPV als Schulversuch“, Chemkon, 24 (4), 251–256, 2017.
 
[37]  D. J. Sam, H. E. Simmons, „Crown polyether chemistry. Potassium permanganate oxidations in benzene“, J. Am. Chem. Soc., 94 (11), 4024–4025, May 1972.
 
[38]  https://banerji-lab.com/downloads/ [accessed, Jan. 20th 2026].
 
[39]  G. Gokel, A. Nakano, „Feeble Forces and Flexible Frameworks“, in Crown Compounds. Toward Future Applications, Weinheim: VCH, 1992, 1–26.
 
[40]  M. K. Janssen, „Mit biologischen Inhalten Brücken zur Chemie bauen. Entwicklung und Erprobung eines Seminars für Sachunterrichtsstudierende“, Universität Siegen, Siegen.
 
[41]  J. Lewing, P. Klein, S. Schneider, „Wirkung technischer und biologischer Kontexte auf das situationale Interesse beim Bearbeiten physikalischer Lernaufgaben zum Energiekonzept“, ZfDN, 29 (1), 8, Dec. 2023.
 
[42]  J. Bennett, F. Lubben, „Context‐based Chemistry: The Salters approach“, International Journal of Science Education, 28 (9), 999–1015, Jul. 2006.
 
[43]  L. Mendez, A. T. Rivera, I. Vasquez, A. Godínez Aguilar, M. T. Owens, und C. L. Meaders, „How students taking introductory biology experience the chemistry content“, J Microbiol Biol Educ., 25(3), e00111-24, Dec. 2024.