Abstract
Natural ion transporters are membrane-bound proteins that play a vital role in many complex biological processes. Malfunction of these proteins is closely associated with various life-threatening diseases called channelopathies. Significant efforts have been devoted to develop transporter replacement therapies that can alleviate the symptoms of channelopathies caused by these faulty proteins. However, due to instability of proteins, much attention has been given to synthesize stable artificial ion transporters that could mimic the function of natural ion transporters. Macrocycle-based ion channels remain much attractive as it has defined cavity to accommodate specific ions and functional group diversity could be easily prepared to mimic the specific function of natural proteins. Hence, this chapter is focused on synthetic ion transporters derived from various macrocycles that transport ions through either unimolecular channels or supramolecular self-assembled channels through non-covalent interactions across the lipid bilayer. An overview of engineering of macrocycles to obtain internally functionalized channels for tuning their ion selectivity has been given. The macrocycle-based ion channels discussed are derived from cyclic peptides, crown ethers, pillar[n]arene, calix[n]arene, resorcin[n]arene, cyclodextrin, hydrazide, organic cages, and metal organic framework units.
References
Hille B (2001) Ion channels of excitable membranes, 3rd edn. Sinauer Associates Inc, Sunderland. Chapter 1
Russell JM (2000) Sodium-Potassium-Chloride Cotransport. Physiol Rev 80(1):211–276. https://doi.org/10.1152/physrev.2000.80.1.211
Lee JH, Lee JH, Choi YR, Kang P, Choi M-G, Jeong K-S (2014) Synthetic K+/cl−-selective symporter across a phospholipid membrane. J Org Chem 79(14):6403–6409. https://doi.org/10.1021/jo501145z
Jentsch TJ, Stein V, Weinreich F, Zdebik AA (2002) Molecular structure and physiological function of chloride channels. Physiol Rev 82(2):503–568. https://doi.org/10.1152/physrev.00029.2001
Davis JT, Okunola O, Quesada R (2010) Recent advances in the transmembrane transport of anions. Chem Soc Rev 39(10):3843–3862. https://doi.org/10.1039/b926164h
Busschaert N, Gale PA (2013) Small-molecule lipid-bilayer anion transporters for biological applications. Angew Chem Int Ed 52(5):1374–1382. https://doi.org/10.1002/anie.201207535
Ashcroft FM (1999) Ion channels and disease: Channelopathies. Academic, San Diego. Chapter 12
Quinton PM (2008) Cystic fibrosis: impaired bicarbonate secretion and mucoviscidosis. Lancet 372(9636):415–417. https://doi.org/10.1016/S0140-6736(08)61162-9
Mount DB, Hoover RS, Hebert SC (1997) The molecular physiology of electroneutral cation-chloride cotransport. J Membrane Biol 158(3):177–186. https://doi.org/10.1007/s002329900255
Shen M-R, Chou C-Y, Hsu K-F, Liu H-S, Dunham PB, Holtzman EJ, Ellory JC (2001) The KCl cotransporter isoform KCC3 can play an important role in cell growth regulation. Proc Nat Acad Sci 98(25):14714–14719. https://doi.org/10.1073/pnas.251388798
Boulenguez P, Liabeuf S, Bos R, Bras H, Jean-Xavier C, Brocard C, Stil A, Darbon P, Cattaert D, Delpire E, Marsala M, Vinay L (2010) Down-regulation of the potassium-chloride cotransporter KCC2 contributes to spasticity after spinal cord injury. Nature Med 16:302. https://doi.org/10.1038/nm.2107
Ashcroft FM (2000) Ion channels and disease: channelopathies. Academic, San Diego
Gouaux E, MacKinnon R (2005) Principles of selective ion transport in channels and pumps. Science 310(5753):1461–1465. https://doi.org/10.1126/science.1113666
McNally BA, O’Neil EJ, Nguyen A, Smith BD (2008) Membrane transporters for anions that use a relay mechanism. J Am Chem Soc 130(51):17274–17275. https://doi.org/10.1021/ja8082363
Bayley H, Cremer PS (2001) Stochastic sensors inspired by biology. Nature 413(6852):226–230
Gu L-Q, Dalla Serra M, Vincent JB, Vigh G, Cheley S, Braha O, Bayley H (2000) Reversal of charge selectivity in transmembrane protein pores by using noncovalent molecular adapters. Proc. Nat. Acad. Sci. 97(8):3959–3964. https://doi.org/10.1073/pnas.97.8.3959
Dartois V, Sanchez-Quesada J, Cabezas E, Chi E, Dubbelde C, Dunn C, Granja J, Gritzen C, Weinberger D, Ghadiri MR, Parr TR (2005) Systemic antibacterial activity of novel synthetic cyclic peptides. Antimicrob Agents Chemother 49(8):3302–3310. https://doi.org/10.1128/aac.49.8.3302-3310.2005
Fernandez-Lopez S, Kim H-S, Choi EC, Delgado M, Granja JR, Khasanov A, Kraehenbuehl K, Long G, Weinberger DA, Wilcoxen KM, Ghadiri MR (2001) Antibacterial agents based on the cyclic d,l-α-peptide architecture. Nature 412(6845):452–455
De Santis P, Morosetti S, Rizzo R (1974) Conformational analysis of regular enantiomeric sequences. Macromolecules 7(1):52–58. https://doi.org/10.1021/ma60037a011
Ghadiri MR, Granja JR, Milligan RA, McRee DE, Khazanovich N (1993) Self-assembling organic nanotubes based on a cyclic peptide architecture. Nature 366(6453):324–327
Ghadiri MR, Granja JR, Buehler LK (1994) Artificial transmembrane ion channels from self-assembling peptide nanotubes. Nature 369(6478):301–304
Montenegro J, Ghadiri MR, Granja JR (2013) Ion Channel models based on self-assembling cyclic peptide nanotubes. Acc Chem Res 46(12):2955–2965. https://doi.org/10.1021/ar400061d
Chapman R, Danial M, Koh ML, Jolliffe KA, Perrier S (2012) Design and properties of functional nanotubes from the self-assembly of cyclic peptide templates. Chem Soc Rev 41(18):6023–6041. https://doi.org/10.1039/C2CS35172B
Sanchez-Quesada J, Ghadiri MR, Bayley H, Braha O (2000) Cyclic peptides as molecular adapters for a pore-forming protein. J Am Chem Soc 122(48):11757–11766. https://doi.org/10.1021/ja002436k
Fletcher JT, Finlay JA, Callow ME, Callow JA, Ghadiri MR (2007) A combinatorial approach to the discovery of biocidal six-residue cyclic d,l-α-peptides against the Bacteria methicillin-resistant Staphylococcus aureus (MRSA) and E. coli and the biofouling Algae Ulva linza and Navicula perminuta. Chem Eur J 13(14):4008–4013. https://doi.org/10.1002/chem.200601583
Horne WS, Wiethoff CM, Cui C, Wilcoxen KM, Amorin M, Ghadiri MR, Nemerow GR (2005) Antiviral cyclic d,l-α-peptides: targeting a general biochemical pathway in virus infections. Bioorg Med Chem 13(17):5145–5153. https://doi.org/10.1016/j.bmc.2005.05.051
Bamberg E, Läuger P (1974) Temperature-dependent properties of gramicidin a channels. Biochim Biophys Acta Biomembr 367(2):127–133. https://doi.org/10.1016/0005-2736(74)90037-6
Granja JR, Ghadiri MR (1994) Channel-mediated transport of glucose across lipid bilayers. J Am Chem Soc 116(23):10785–10786. https://doi.org/10.1021/ja00102a054
Sánchez-Quesada J, Sun Kim H, Ghadiri MR (2001) A synthetic pore-mediated transmembrane transport of glutamic acid. Angew Chem Int Ed 40(13):2503–2506. https://doi.org/10.1002/1521-3773(20010702)40:13<2503::AID-ANIE2503>3.0.CO;2-E
Granja JR, Ghadiri MR (1994) Channel-mediated transport of glucose across lipid bilayers. J Am Chem Soc 116(23):10785–10786. https://doi.org/10.1021/ja00102a054
Suga T, Osada S, Kodama H (2012) Formation of ion-selective channel using cyclic tetrapeptides. Bioorg Med Chem 20(1):42–46. https://doi.org/10.1016/j.bmc.2011.11.036
Helsel AJ, Brown AL, Yamato K, Feng W, Yuan L, Clements AJ, Harding SV, Szabo G, Shao Z, Gong B (2008) Highly conducting transmembrane pores formed by aromatic Oligoamide macrocycles. J Am Chem Soc 130(47):15784–15785. https://doi.org/10.1021/ja807078y
Zhou X, Liu G, Yamato K, Shen Y, Cheng R, Wei X, Bai W, Gao Y, Li H, Liu Y, Liu F, Czajkowsky DM, Wang J, Dabney MJ, Cai Z, Hu J, Bright FV, He L, Zeng XC, Shao Z, Gong B (2012) Self-assembling subnanometer pores with unusual mass-transport properties. Nat Commun 3:949. https://doi.org/10.1038/ncomms1949
Baumeister B, Sakai N, Matile S (2001) P-Octiphenyl β-barrels with Ion Channel and esterase activity org. Lett 3(26):4229–4232. https://doi.org/10.1021/ol016914n
Sakai N, Sorde N, Das G, Perrottet P, Gerard D, Matile S (2003) Synthetic multifunctional pores: deletion and inversion of anion/cation selectivity using pM and pH. Org Biomol Chem 1(7):1226–1231. https://doi.org/10.1039/b210604c
Cornell BA, Braach-Maksvytis VLB, King LG, Osman PDJ, Raguse B, Wieczorek L, Pace RJ (1997) A biosensor that uses ion-channel switches. Nature 387(6633):580–583. http://www.nature.com/nature/journal/v387/n6633/suppinfo/387580a0_S1.html
Gu L-Q, Braha O, Conlan S, Cheley S, Bayley H (1999) Stochastic sensing of organic analytes by a pore-forming protein containing a molecular adapter. Nature (London) 398(6729):686–690
Doyle DA, Cabral JM, Pfuetzner RA, Kuo A, Gulbis JM, Cohen SL, Chait BT, MacKinnon R (1998) The structure of the potassium channel: molecular basis of K+ conduction and selectivity. Science (Washington, D C) 280(5360):69–77. https://doi.org/10.1126/science.280.5360.69
Dutzler R, Campbell EB, MacKinnon R (2003) Gating the selectivity filter in ClC chloride channels. Science 300(5616):108–112. https://doi.org/10.1126/science.1082708
Garcia-Fandino R, Amorin M, Castedo L, Granja JR (2012) Transmembrane ion transport by self-assembling α,γ-peptide nanotubes. Chem Sci 3(11):3280–3285. https://doi.org/10.1039/C2SC21068A
Wang D, Guo L, Zhang J, Jones LR, Chen Z, Pritchard C, Roeske RW (2001) Artificial ion channels formed by a synthetic cyclic peptide. J Pept Res 57(4):301–306. https://doi.org/10.1046/j.1397-002X.2000.00823.x
Hennig A, Fischer L, Guichard G, Matile S (2009) Anion-macrodipole interactions: self-assembling oligourea/amide macrocycles as anion transporters that respond to membrane polarization. J Am Chem Soc 131(46):16889–16895. https://doi.org/10.1021/ja9067518
Gilles A, Barboiu M (2016) Highly selective artificial K+ channels: an example of selectivity-induced transmembrane potential. J Am Chem Soc 138(1):426–432. https://doi.org/10.1021/jacs.5b11743
[a] Cazacu A, Tong C, Van der Lee A, Fyles TM, Barboiu M (2006) Columnar self-assembled Ureido crown ethers: an example of Ion-Channel Organization in lipid bilayers. J Am Chem Soc 128(29):9541–9548. https://doi.org/10.1021/ja061861w [b] Barboiu M, Vaughan G, van der Lee A (2003) Self-organized heteroditopic macrocyclic superstructures. Org Lett 5(17):3073–3076. https://doi.org/10.1021/ol035096r
Schneider S, Licsandru E-D, Kocsis I, Gilles A, Dumitru F, Moulin E, Tan J, Lehn J-M, Giuseppone N, Barboiu M (2017) Columnar self-assemblies of Triarylamines as scaffolds for artificial biomimetic channels for ion and for water transport. J Am Chem Soc 139(10):3721–3727. https://doi.org/10.1021/jacs.6b12094
Zhanhu S, Mihail B, Yves-Marie L, Eddy P, Alexandru R (2015) Highly selective artificial cholesteryl crown ether K+-channels. Angew. Chem., Int. Ed. 54(48):14473–14477. https://doi.org/10.1002/anie.201506430
Licsandru E, Kocsis I, Shen Y-x, Murail S, Legrand Y-M, van der Lee A, Tsai D, Baaden M, Kumar M, Barboiu M (2016) Salt-excluding artificial water channels exhibiting enhanced dipolar water and proton translocation. J Am Chem Soc 138(16):5403–5409. https://doi.org/10.1021/jacs.6b01811
Sun Z, Gilles A, Kocsis I, Legrand Y-M, Petit E, Barboiu M (2016) Squalyl crown ether self-assembled conjugates: an example of highly selective artificial K+ channels. Chem Eur J 22(6):2158–2164. https://doi.org/10.1002/chem.201503979
Ren C, Shen J, Zeng H (2017) Combinatorial evolution of fast-conducting highly selective K+-channels via modularly tunable directional assembly of crown ethers. J Am Chem Soc 139(36):12338–12341. https://doi.org/10.1021/jacs.7b04335
Cazacu A, Legrand Y-M, Pasc A, Nasr G, Van der Lee A, Mahon E, Barboiu M (2009) Dynamic hybrid materials for constitutional self-instructed membranes. Proc Natl Acad Sci 106(20):8117–8122. https://doi.org/10.1073/pnas.0813257106
Barboiu M (2018) Encapsulation versus self-aggregation toward highly selective artificial K+ channels. Acc Chem Res 51(11):2711–2718. https://doi.org/10.1021/acs.accounts.8b00311
Voyer N, Robitaille M (1995) Novel functional artificial Ion Channel. J Am Chem Soc 117(24):6599–6600. https://doi.org/10.1021/ja00129a027
Bao C, Ma M, Meng F, Lin Q, Zhu L (2015) Efficient synthetic supramolecular channels and their light-deactivated ion transport in bilayer lipid membranes. New J Chem 39(8):6297–6302. https://doi.org/10.1039/C5NJ00937E
Zhou Y, Chen Y, Zhu P-P, Si W, Hou J-L, Liu Y (2017) Reversible photo-gated transmembrane channel assembled from an acylhydrazone-containing crown ether triad. Chem Commun 53(26):3681–3684. https://doi.org/10.1039/C7CC01123G
Hall CD, Kirkovits GJ, Hall AC (1999) Towards a redox-active artificial ion channel. Chem Commun 18:1897–1898. https://doi.org/10.1039/A904069B
Murillo O, Watanabe S, Nakano A, Gokel GW (1995) Synthetic models for transmembrane channels: structural variations that Alter cation flux. J Am Chem Soc 117(29):7665–7679. https://doi.org/10.1021/ja00134a011
Gokel GW (2000) Hydraphiles: design, synthesis and analysis of a family of synthetic, cation-conducting channels. Chem Commun 1:1–9. https://doi.org/10.1039/A903825F
Gokel GW, Carasel IA (2007) Biologically active, synthetic ion transporters. Chem Soc Rev 36(2):378–389. https://doi.org/10.1039/B605910B
Abel E, Maguire GEM, Meadows ES, Murillo O, Jin T, Gokel GW (1997) Planar bilayer conductance and fluorescence studies confirm the function and location of a synthetic, sodium-ion-Conducting Channel in a phospholipid bilayer membrane. J Am Chem Soc 119(38):9061–9062. https://doi.org/10.1021/ja971098t
Leevy WM, Huettner JE, Pajewski R, Schlesinger PH, Gokel GW (2004) Synthetic Ion Channel activity documented by electrophysiological methods in living cells. J Am Chem Soc 126(48):15747–15753. https://doi.org/10.1021/ja046626x
Abel E, Maguire GEM, Murillo O, Suzuki I, De Wall SL, Gokel GW (1999) Hydraphile channels: structural and fluorescent probes of position and function in a phospholipid bilayer. J Am Chem Soc 121(39):9043–9052. https://doi.org/10.1021/ja9909172
Gokel GW, Ferdani R, Liu J, Pajewski R, Shabany H, Uetrecht P (2001) Hydraphile channels: models for transmembrane, cation-conducting transporters. Chem Eur J 7(1):33–39. https://doi.org/10.1002/1521-3765(20010105)7:1<33::AID-CHEM33>3.0.CO;2-3
Murillo O, Abel E, Maguire GEM, Gokel GW (1996) A tris(macrocycle) that exhibits H-bond-induced blockage of the cation channel faction in a phospholipid bilayer. Chem Commun 18:2147–2148. https://doi.org/10.1039/CC9960002147
Pechulis AD, Thompson RJ, Fojtik JP, Schwartz HM, Lisek CA, Frye LL (1997) The design, synthesis and transmembrane transport studies of a biomimetic sterol-based ion channel. Bioorg Med Chem 5(10):1893–1901. https://doi.org/10.1016/S0968-0896(97)00085-0
Carmichael VE, Dutton PJ, Fyles TM, James TD, Swan JA, Zojaji M (1989) Biomimetic ion transport: a functional model of a unimolecular ion channel. J Am Chem Soc 111(2):767–769. https://doi.org/10.1021/ja00184a075
Fyles TM, James TD, Pryhitka A, Zojaji M (1993) Assembly of ion channel mimics from a modular construction set. J Org Chem 58(26):7456–7468. https://doi.org/10.1021/jo00078a026
Fyles TM, James TD, Kaye KC (1993) Activities and modes of action of artificial ion channel mimics. J Am Chem Soc 115(26):12315–12321. https://doi.org/10.1021/ja00079a011
Si W, Hu XB, Liu XH, Fan RH, Chen ZX, Weng LH, Hou JL (2011) Self-assembly and proton conductance of organic nanotubes from pillar[5]arenes. Tetrahedron Lett 52(19):2484–2487. https://doi.org/10.1016/j.tetlet.2011.03.019
Si W, Chen L, Hu X-B, Tang G, Chen Z, Hou J-L, Li Z-T (2011) Selective artificial transmembrane channels for protons by formation of water wires. Angew. Chem., Int. Ed 50(52):12564–12568. https://doi.org/10.1002/anie.201106857
Hu XB, Chen ZX, Tang GF, Hou JL, Li ZT (2012) Single-molecular artificial transmembrane water channels. J Am Chem Soc 134(20):8384–8387. https://doi.org/10.1021/ja302292c
Si W, Xin PY, Li ZT, Hou JL (2015) Tubular unimolecular transmembrane channels: construction strategy and transport activities. Acc Chem Res 48(6):1612–1619. https://doi.org/10.1021/acs.accounts.5b00143
Chen L, Si W, Zhang L, Tang GF, Li ZT, Hou JL (2013) Chiral selective transmembrane transport of amino acids through artificial channels. J Am Chem Soc 135(6):2152–2155. https://doi.org/10.1021/ja312704e
Si W, Li ZT, Hou JL (2014) Voltage-driven reversible insertion into and leaving from a lipid bilayer: tuning transmembrane transport of artificial channels. Angew Chem Int Ed 53(18):4578–4581. https://doi.org/10.1002/anie.201311249
Zhang M, Zhu P-P, Xin P, Si W, Li Z-T, Hou J-L (2017) Synthetic Channel specifically inserts into the lipid bilayer of gram-positive Bacteria but not that of mammalian erythrocytes. Angew Chem Int Ed 56(11):2999–3003. https://doi.org/10.1002/anie.201612093
Chen J-Y, Haoyang W-W, Zhang M, Wu G, Li Z-T, Hou J-L (2018) A synthetic channel that efficiently inserts into mammalian cell membranes and destroys cancer cells. Faraday Discuss. https://doi.org/10.1039/C8FD00009C
Feng W-X, Sun Z, Zhang Y, Legrand Y-M, Petit E, Su C-Y, Barboiu M (2017) Bis-15-crown-5-ether-pillar[5]arene K+-responsive channels. Org Lett 19(6):1438–1441. https://doi.org/10.1021/acs.orglett.7b00352
Xin P, Kong H, Sun Y, Zhao L, Fang H, Zhu H, Jiang T, Guo J, Zhang Q, Dong W, Chen CP (2019) Artificial K+ channels formed by Pillararene-Cyclodextrin hybrid molecules: tuning cation selectivity and generating membrane potential. Angew Chem Int Ed Engl 58(9):2779–2784. https://doi.org/10.1002/anie.201813797
Xin PY, Zhang L, Su P, Hou JL, Li ZT (2015) Hydrazide macrocycles as effective transmembrane channels for ammonium. Chem Commun 51(23):4819–4822. https://doi.org/10.1039/c5cc00691k
Xin P, Tan S, Sun Y, Ren Q, Dong W, Guo J, Jiang T, Chen C-P (2017) One-pot formation of hydrazide macrocycles with modified cavities: an example of pH-sensitive unimolecular cation channels. Chem Commun 53(38):5322–5325. https://doi.org/10.1039/C7CC02076G
Xin P, Tan S, Wang Y, Sun Y, Wang Y, Xu Y, Chen C-P (2017) Functionalized hydrazide macrocycle ion channels showing pH-sensitive ion selectivities. Chem Commun 53(3):625–628. https://doi.org/10.1039/C6CC08943G
de Mendoza J, Cuevas F, Prados P, Meadows ES, Gokel GW (1998) A synthetic cation-transporting calix[4]arene derivative active in phospholipid bilayers. Angew Chem Int Ed 37(11):1534–1537. https://doi.org/10.1002/(SICI)1521-3773(19980619)37:11<1534::AID-ANIE1534>3.0.CO;2-B
Maulucci N, De Riccardis F, Botta CB, Casapullo A, Cressina E, Fregonese M, Tecilla P, Izzo I (2005) Calix[4]arene-cholic acid conjugates: a new class of efficient synthetic ionophores. Chem Commun (10):1354–1356. https://doi.org/10.1039/B415908J
Iqbal KSJ, Cragg PJ (2007) Transmembrane ion transport by calixarenes and their derivatives. Dalton Trans (1):26–32. https://doi.org/10.1039/B613867P
Iqbal KSJ, Allen MC, Fucassi F, Cragg PJ (2007) Artificial transmembrane ion channels from commercial surfactants. Chem Commun 38:3951–3953. https://doi.org/10.1039/B707194A
Lawal O, Iqbal KSJ, Mohamadi A, Razavi P, Dodd HT, Allen MC, Siddiqui S, Fucassi F, Cragg PJ (2009) An artificial sodium ion channel from calix[4]arene in the 1,3-alternate conformation. Supramol Chem 21(1–2):55–60. https://doi.org/10.1080/10610270802528307
Yoshino N, Satake A, Kobuke Y (2001) An artificial ion channel formed by a macrocyclic resorcin[4]arene with amphiphilic cholic acid ether groups. Angew Chem Int Ed 40(2):457–459. https://doi.org/10.1002/1521-3773(20010119)40:2<457::AID-ANIE457>3.0.CO;2-F
Tanaka Y, Kobuke Y, Sokabe M (1995) A non-peptidic ion channel with K+ selectivity. Angew Chem Int Ed Engl 34(6):693–694. https://doi.org/10.1002/anie.199506931
Wright AJ, Matthews SE, Fischer WB, Beer PD (2001) Novel resorcin[4]arenes as potassium-selective ion-channel and transporter mimics. Chem Eur J 7(16):3474–3481. https://doi.org/10.1002/1521-3765(20010817)7:16<3474::AID-CHEM3474>3.0.CO;2-6
Paquet V, Zumbuehl A, Carreira EM (2006) Biologically active amphotericin B-calix[4]arene conjugates. Bioconjug Chem 17(6):1460–1463. https://doi.org/10.1021/bc060205i
Jin T (2000) Photocontrol of Na+ transport across a phospholipid bilayer containing a bisanthroylcalix[4]arene carrier. Chem Commun (Cambridge) (15):1379–1380. https://doi.org/10.1039/b002034f
Davis JT, Okunola O, Quesada R (2010) Recent advances in the transmembrane transport of anions. Chem Soc Rev 39(10):3843–3862. https://doi.org/10.1039/B926164H
Okunola OA, Seganish JL, Salimian KJ, Zavalij PY, Davis JT (2007) Membrane-active calixarenes: toward ‘gating’ transmembrane anion transport. Tetrahedron 63(44):10743–10750. https://doi.org/10.1016/j.tet.2007.06.124
Sidorov V, Kotch FW, Kuebler JL, Lam Y-F, Davis JT (2003) Chloride transport across lipid bilayers and transmembrane potential induction by an Oligophenoxyacetamide. J Am Chem Soc 125(10):2840–2841. https://doi.org/10.1021/ja029372t
Sidorov V, Kotch FW, Abdrakhmanova G, Mizani R, Fettinger JC, Davis JT (2002) Ion Channel formation from a calix[4]arene amide that binds HCl. J Am Chem Soc 124(10):2267–2278. https://doi.org/10.1021/ja012338e
Seganish JL, Santacroce PV, Salimian KJ, Fettinger JC, Zavalij P, Davis JT (2006) Regulating supramolecular function in membranes: calixarenes that enable or inhibit transmembrane cl¯ transport. Angew Chem Int Ed 45(20):3334–3338. https://doi.org/10.1002/anie.200504489
Izzo I, Licen S, Maulucci N, Autore G, Marzocco S, Tecilla P, De Riccardis F (2008) Cationic calix[4]arenes as anion-selective ionophores. Chem Commun (Cambridge, UK) (26):2986–2988. https://doi.org/10.1039/b719482j
Tabushi I, Kuroda Y, Yokota K (1982) A,C,D,F-tetrasubstituted β-cyclodextrin as an artificial channel compound. Tetrahedron Lett 23(44):4601–4604. https://doi.org/10.1016/S0040-4039(00)85664-6
Madhavan N, Robert EC, Gin MS (2005) A highly active anion-selective amino-cyclodextrin ion channel. Angew Chem Int Ed 44(46):7584–7587. https://doi.org/10.1002/anie.200501625
Madhavan N, Gin MS (2007) Increasing pH causes faster anion- and cation-transport rates through a synthetic ion channel. Chembiochem 8(15):1834–1840. https://doi.org/10.1002/cbic.200700321
Jog PV, Gin MS (2008) A light-gated synthetic Ion Channel. Org Lett 10(17):3693–3696. https://doi.org/10.1021/ol8013045
Chadwick DJ, Cardew G (eds) (1999) Gramicidin and related ion channel-forming peptides. In: Proceedings of a symposium held at the Novartis Foundation, London, 17–19 Nov 1998. [Novartis foundation symposium, 1999; 225]. vol Copyright (C) 2016 American Chemical Society (ACS). All Rights Reserved. Wiley
Reiß P, Koert U (2013) Ion-channels: goals for function-oriented synthesis. Acc Chem Res 46(12):2773–2780. https://doi.org/10.1021/ar400007w
Pfeifer JR, Reiß P, Koert U (2006) Crown ether–gramicidin hybrid ion channels: dehydration-assisted ion selectivity. Angew Chem Int Ed 45(3):501–504. https://doi.org/10.1002/anie.200502570
Jeon YJ, Kim H, Jon S, Selvapalam N, Oh DH, Seo I, Park C-S, Jung SR, Koh D-S, Kim K (2004) Artificial Ion Channel formed by cucurbit[n]uril derivatives with a carbonyl group fringed portal reminiscent of the selectivity filter of K+ channels. J Am Chem Soc 126(49):15944–15945. https://doi.org/10.1021/ja044748j
Benke BP, Aich P, Kim Y, Kim KL, Rohman MR, Hong S, Hwang I-C, Lee EH, Roh JH, Kim K (2017) Iodide-selective synthetic ion channels based on shape-persistent organic cages. J Am Chem Soc 139(22):7432–7435. https://doi.org/10.1021/jacs.7b02708
Fyles TM, Tong CC (2007) Long-lived and highly conducting ion channels formed by lipophilic ethylenediamine palladium(ii) complexes. New J Chem 31(5):655–661. https://doi.org/10.1039/B610660A
Satake A, Yamamura M, Oda M, Kobuke Y (2008) Transmembrane Nanopores from porphyrin Supramolecules. J Am Chem Soc 130(20):6314–6315. https://doi.org/10.1021/ja801129a
Boccalon M, Iengo E, Tecilla P (2012) Metal–organic transmembrane Nanopores. J Am Chem Soc 134(50):20310–20313. https://doi.org/10.1021/ja310425j
Jung M, Kim H, Baek K, Kim K (2008) Synthetic Ion Channel based on metal–organic Polyhedra. Angew Chem Int Ed 47(31):5755–5757. https://doi.org/10.1002/anie.200802240
Kulikov OV, Li R, Gokel GW (2009) A synthetic Ion Channel derived from a Metallogallarene capsule that functions in phospholipid bilayers. Angew Chem Int Ed 48(2):375–377. https://doi.org/10.1002/anie.200804099
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2019 Springer Nature Singapore Pte Ltd.
About this entry
Cite this entry
Behera, H., Hou, JL. (2019). Macrocycle-Based Synthetic Ion Channels. In: Liu, Y., Chen, Y., Zhang, HY. (eds) Handbook of Macrocyclic Supramolecular Assembly . Springer, Singapore. https://doi.org/10.1007/978-981-13-1744-6_64-1
Download citation
DOI: https://doi.org/10.1007/978-981-13-1744-6_64-1
Received:
Accepted:
Published:
Publisher Name: Springer, Singapore
Print ISBN: 978-981-13-1744-6
Online ISBN: 978-981-13-1744-6
eBook Packages: Springer Reference Chemistry and Mat. ScienceReference Module Physical and Materials ScienceReference Module Chemistry, Materials and Physics