Calix[n]arenes as synthetic membrane transporters: A minireview

Analytical Letters

Volumn 43, Issue 7, 2010, Pages 1355-1366

  Mutihac, Lucia ^a  

^a UNIVERSITY OF BUCHAREST   (Romania)

Author keywords

Biological compounds; Calix n arenes; Carrier; Ion channel; Membrane transport

Indexed keywords

EID: 77952597135     PISSN: 00032719     EISSN: 1532236X     Source Type: Journal    
DOI: 10.1080/00032710903518765     Document Type: Article

References (82)

1. Agre, P., L. S. King, M. Yasui, W. B. Guggino, O. P. Ottersen, Y. Fujiyoshi, A. Engel, and S. Nielsen. 2002. Aquaporin water channels - from atomic structure to clinical medicine. J. Physiol. 542: 3-16.
2. Antipin, I. S., I. I. Stoikov, E. M. Pinkhassik, N. Fitseva, I. Stibor, and A. I. Konovalov. 1997. Calix[4]arene based a-aminophosphonates: Novel carriers for zwitterionic amino acids transport. Tetrahedron Lett. 38: 5865-5868.
3. Araki, K., K. Inada, and S. Shinkai. 1996. Chiral recognition of a-amino acid derivatives with a homooxacalix3arene: Construction of a pseudo-C2-symmetrical compound from a C3 symmetrical macrocycle. Angew. Chem. Int. Ed. Engl. 35: 72-74.
4. 1H NMR investigation supported by molecular modeling. Org. Biomol. Chem. 4: 243-249.
5. Arena, G., G. G. Lombardo, E. Rizzarelli, D. Sciotto, R. Ungaro, and A. Casnati. 1992. Water soluble calix[4]arenes. A thermodynamic investigation of proton complex formation. Supramol. Chem. 1: 19-24.
6. Asfari, Z., V. Bohmer, J. Harrowfield, and J. Vicens (eds.). 2001. Calixarene 2001. Dordrecht: Kluwer Academic Publisher.
7. Atwood, J. L., L. J. Barbour, A. Jerga, L. Brandi, and B. L. Schottel. 2002. Guest transport in a nonporous organic solid via dynamic van der Waals cooperativity. Science. 298: 1000-1002.
8. Baldini, L., A. Casnati, F. Sansone, and R. Ungaro. 2007. Calixarene-based multivalent ligands. Chem. Soc. Rev. 36: 254-266.
9. Bohmer, V. 1995. Calixarenes, macrocycles with (almost) unlimited possibilities. Angew. Chem. Int. Ed. Engl. 34: 713-745.
10. Bois, J., I. Bonnamour, C. Duchamp, H. Parrot-Lopez, U. Darbost, and C. Felix. 2009. Enantioselective recognition of amino acids by chiral peptido-calix[4]arenes and thiacalix[4]- arenes. New J. Chem. 33: 2128-2135.
11. Buschmann, H. J., and L. Mutihac. 2002. Complexation, solvent extraction, an transport through liquid membrane of protonated peptides using crown ethers. Anal. Chim. Acta. 466: 101-108.
12. Buschmann, H.-J., L. Mutihac, and K. Janssen. 2001. Complexation of some amine compounds by macrocyclic receptors. J. Incl. Phenom. Macrocycl. Chem. 39: 1-11.
13. Buschmann, H.-J., L. Mutihac, and E. Schollmeyer. 2003. Complexation of some amino acids and peptides by p-sulfonatocalix[4]arene and hexasodium p-sulfonatocalix[6]arene in aqueous solution. J. Incl. Phenom. Macrocyclic Chem. 46: 133-137.
14. Buschmann, H.-J., L. Mutihac, and E. Schollmeyer. 2006. 11-Aminoundecanoic acid, cyclodextrins (a, b) and cucurbit[n]urils (n1/46, 7) as building blocks for supramolecular assemblies: A thermodynamic study. J. Incl. Phenom. Macrocycl. Chem. 56: 363-368.
15. Cazacu, A., C. Tong, A. Van der Lee, T. M. Fyles, and M. Barboiu. 2006. Columnar self-assembled ureido crown ethers: An example of ion-channel organization in lipid bilayers. J. Am. Chem. Soc. 128: 9541-9548.
16. Chang, S.-K., H.-S. Hwang, H. Son, J. Youk, and Y. S. Kang. 1991. Selective transport of amino acid esters through in chloroform liquid membrane by a calix[6]arene-based ester carrier. J. Chem. Soc. Chem. Commun. 4: 217-218.
17. Chang, S.-K., H. Son, and H.-S. Hwang. 1990. Selective transport of amino acids derivatives through calix[6]arene-based liquid membrane. Bull. Korean Chem. Soc. 11: 364-365.
18. Cragg, P. J., and K. S. J. Iqbal. 2007. Transmembrane ion transport by calixarenes and their derivatives. Dalton Trans. 1: 26-32.
19. Da Silva, E., and A. W. Coleman. 2003. Synthesis and complexation properties towards amino acids of mono-substituted p-sulphonato-calix-[n]-arenes. Tetrahedron 59: 7357-7364.
20. Danylyuk, O., and K. Suwinska. 2009. Solid-state of calixarenes with biorelevant molecules. Chem. Commun. 5799-5813.
21. Davis, A. P., D. N. Sheppard, and B. D. Smith. 2007. Development of synthetic membrane transporters for anions. Chem. Soc. Rev. 36: 348-357.
22. de Mendoza, J., F. Cuevas, P. Prados, E. S. Meadows, and G. W. Gokel. 1998. A synthetic cation-transporting calix[4]arene derivative active in phospholipid bilayers. Angew. Chem. Int. Ed. 37: 1534-1537.
23. Demirtas, H. N., S. Bozkurt, M. Durmaz, M. Yilmaz, and A. Sirit. 2009. Chiral calix[4]- azacrowns for enantiomeric recognition of amino acid derivatives. Tetrahedron 65: 3014-3018.
24. Douteau-Guevel, N., A. W. Coleman, J.-P. Morel, and N. Morel-Desrosiers. 1999. Complexation of the basic amino acids lysine and arginine by three sulfonatocalix[n]arenes (n1/4 4, 6 and 8) in water: microcalorimetric determination of the Gibbs energies, enthalpies and entropies of complexation. J. Chem. Soc. Perkin Trans. 2: 629-634.
25. Douteau-Guevel, N., F. Perret, A. W. Coleman, J.-P. Morel, and N. Morel-Desrosiers. 2002. Binding of dipeptides and tripeptides containing lysine or arginine by p-sulfonatocalixarenes in water: NMR and microcalorimetric studies. J. Chem. Soc. Perkin Trans. 2: 524-532.
26. {thorn} conduction and selectivity. Science. 280: 69-77.
27. Durmaz, M., S. Alpaydin, A. Sirit, and M. Yilmaz. 2007. Enantiomeric recognition of amino acid derivatives by chiral Schiff base derivatives of calix[n]arene. Tetrahedron: Asymmetry 18: 900-905.
28. Fyles, T. W. 1996. Cation transport across bilayer membranes: Techniques and mechanisms. In Physical supramolecular chemistry, 39-46, ed. L. Echegoyen and E. Kaifer. Dordrecht: Kluwer Academic Publisher.
29. Garrier, E., S. Le Gac, and I. Jabin. 2005. First enantiopure calix[6]aza-cryptand: Synthesis and chiral recognition properties towards neutral molecules. Tetrahedron: Asymmetry 16: 3767-3771.
30. Ghadiri, M. R., J. R. Granja, and L. K. Buehler. 1994. Artificial transmembrane ion channels from self-assembling peptide nanotubes. Nature 369: 301-304.
31. Gokel, G. W., and I. A. Carasel. 2007. Biologically active, synthetic ion transporters. Chem. Soc. Rev. 36: 378-389.
32. Gokel, G. W., and M. M. Daschbach. 2008. Coordination and transport of alkali metal cations through phospholipid bilayer membranes by hydraphile channels. Coord. Chem. Rev. 252: 886-902.
33. Gutsche, C. D. 1998. Calixarene Revisited. Cambridge: The Royal Society of Chemistry.
34. Hamdi, A., R. Souane, L. Kim, R. Abidi, L. Mutihac, and J. Vicens. 2009. Extraction behaviour of amino acid esters by functionalized calix[4]arenes. J. Incl. Phenom. Macrocycl. Chem. 64: 95-100.
35. Hu, H., J. He, A. S. C. Chan, X. Han, and J.-P. Cheng. 1999. New chiral macrocyclic ligands. Design and synthesis of (R)-cysteine-containing calix[4]arenes. Tetrahedron: Asymmetry 10: 2685-2689.
36. Ikeda, A., and S. Shinkai. 1997. Novel cavity design using calix[n]arene skeletons: Towards molecular recognition and metal binding. Chem. Rev. 97: 1713-1734.
37. Iqbal, K. S., M. C. Allen, F. Fucassi, and P. J. Cragg. 2007. Artificial transmembrane ion channels from commercial surfactants. Chem. Commun. 38: 3951-3953.
38. Izatt, S. R., R. T. Hawkins, J. J. Christensen, and R. M. Izatt. 1985. Cation transport from multiple alkali cation mixture using a liquid membrane system containing a series of calixarene carriers. J. Am. Chem. Soc. 107: 63-66.
39. {thorn} channels. J. Am. Chem. Soc. 124: 15944-15945.
40. Jin, T. 1999. Membrane transport of neurotransmitter acetylcholine and related compounds across a phospholipid bilayer by a calix[6]arene ester. Chem. Commun. 20: 2129-2130.
41. Jin, T., M. Kinjo, Y. Kobayashi., and H. Hirata. 1998. Ion transport activity of calix[n]arene (n1/44,5,6,7,8) esters toward alkali-metal cations in a phospholipid bilayer membrane. J. Chem. Soc., Faraday Trans. 94: 3135-3140.
42. 1H NMR. J. Chem. Soc. Perkin Trans. 2: 258-263.
43. Kim, L., A. Hamdi, A. D. Stancu, R. Souane, L. Mutihac, and J. Vicens. 2010. Selective membrane transport of amino acids by functionalized calix[4]arenes. J. Incl. Phenom. Macrocycl. Chem. 66: 55-59.
44. Kim, L., A.-D. Stancu, E. Diacu, H.-J. Buschmann, and L. Mutihac. 2009. Extraction and transport behavior of aromatic amino acids by modified cyclodextrin. Supramol. Chem. 21: 131-134.
45. Kocabas, E., A. Karakucuk, A. Sirit, and M. Yilmaz. 2006. Synthesis of new chiral calix[4]- arene diamide derivatives for liquid phase extraction of a-amino acid methylesters. Tetrahedron: Asymmetry 17: 1514-1520.
46. Le Gac, S., M. Giorgi, and I. Jabin. 2007. Calix[6]arene tris-carboxylic acid derivatives: X-ray and NMR characterization of their remarkable host-guest properties toward ammonium ions. Supramol. Chem. 19: 185-197.
47. Lehn, J. M. 1995. Supramolecular Chemistry. Concepts and Perspectives. Weinheim: VCH.
48. Lehn, J.-M., R. Meric, J.-P. Vigneron, M. Cesario, J. Gujihem, C. Pascard, Z. Asfari, and J. Vicens. 1995. Binding of acethylcholine and other quaternary ammonium cations by sulfonated calixarenes. Crystal structure of a [choline-tetrasulfonated calyx[4]arene] complex. Supramol. Chem. 5: 97-103.
49. MacKinnon, R. 2004. Potassium channels and the atomic basis of selective ion conduction. Angew. Chem. Int. Ed. 43: 4265-4277.
50. Matile, S. 2001. En route to supramolecular functional plasticity:artificial b-barrels, the barrel-stave motif, and related approaches. Chem. Soc. Rev. 30: 158-167.
51. Matile, S., and N. Sakai. 2006. The characterization of synthetic ion channels and pores. In Analytical methods in supramolecular chemistry, Chapter 11, ed. C. A. Schalley. Weinheim: Wiley-VCH.
52. Maulucci, N., F. De Riccardis, C. B. Botta, A. Casapullo., E. Cressina, M. Fregonese, P. Tecilla, and I. Izzo. 2005. Calix[4]arene-cholic acid conjugates: A new class of efficient synthetic ionophores. Chem. Commun. 10: 1354-1356.
53. McNally, B. A., W. M. Leevy, and B. D. Smith. 2007. Recent Advances in Synthetic Membrane Transporters. Supramol. Chem. 19: 29-37.
54. Middleton Boon, J., and B. D. Smith. 2002. Synthetic membrane transporters. Curr. Opin. Chem. Biol. 6: 749-756.
55. Murillo, O., S. Watanabe, A. Nakano, and G. W. Gokel. 1995. Synthetic models for transmembrane channels: Structural variations that alter cation flux. J. Am. Chem. Soc. 117: 7665-7679.
56. Mutihac, L. 2008. Functionalized calix[n]arenes as membrane transporters for biological compounds. A mini review. Curr. Drug. Discov. Technol. 5: 98-104.
57. Mutihac, L., H.-J. Buschmann, and E. Diacu. 2002. Calixarene derivatives as carriers in liquid membrane separation. Desalination 148: 253-256.
58. Mutihac, L., H.-J. Buschmann, K. Jansen, and A. Wego. 2001. Interaction and transport through liquid membranes of some dipeptide complexes with macrocyclic receptors. Mat. Sci. & Eng. C: Biomimetic and Supramolecular Systems. 18: 259-264.
59. Mutihac, L., H.-J Buschmann, and R. Mutihac. 2003. Relationship between extraction properties and transport through liquid membrane of amino acids by calixarene derivatives. Indian J. Chem. 42 A: 2978-2981.
60. Mutihac, L., H.-J. Buschmann, R.-C. Mutihac, and E. Schollmeyer. 2005. Complexation and separation of amines, amino acids, and peptides by functionalized calix[n]arenes. J. Incl. Phenom. Macrocyclic Chem. 51: 1-10.
61. Mutihac, L., H.-J. Buschmann, A. Tudorescu, and R. Mutihac. 2003. Some aspects of extractibility and transport of amino acids esters by calixarenes. J. Incl. Phenom. Macrocyclic Chem. 47: 123-128.
62. Mutihac, L., and R. Mutihac. 2007. Liquid-liquid extraction and transport through membrane of amino acid methylesters by calix[n]arene derivatives. J. Incl. Phenom. Macrocyclic Chem. 59: 177-181.
63. Okada, Y., Y. Kasai, and J. Nishimura. 1995. The selective extraction and transport of amino acids by calix[4]arene-derived esters. Tetrahedron Lett. 36: 555-558.
64. Oshima, T., K. Inoue, S. Furusaki, and M. Goto. 2003. Liquid membrane transport of amino acids by a calix[6]arene carboxylic acid derivative. J. Membr. Sci. 217: 87-97.
65. Perret, A., A. N. Lazar, and A. W. Coleman. 2006. Biochemistry of the para-sulfonato-calix- [n]arenes. Chem. Commun. 23: 2425-2438.
66. Pregel, M. J., L. Jullien, J. Canceille, L.L. Lacombe and J.-M. Lehn. 1995. Channel-type molecular structures. Part 4. Transmembrane transport of alkali-metal ion by "bouquet" molecules. J. Chem. Soc., Perkin Trans 2: 417-426.
67. Pulpoka, B., L. Baklouti, J. S. Kim, and J. Vicens. 2007. 1,3-Alternate calix tubes. Shuttling of cations. In Calixarenes in the nanoworld, Chapter 7, ed. J. Vicens, and J. Harrowfield. Dordrecht: Springer.
68. Rudkevich, D. M. 2007. Progress in supramolecular chemistry of gases. Eur. J. Org. Chem. 20: 3255-3270.
69. Sansone, F., L. Baldini, A. Casnati, E. Chierici, G. Faimani, F. Ugozzolli, and R. Ungaro. 2004. Chiral dimeric capsules from N, C-linked peptidocalix[4]arenes self-assembled through an antiparallel b-sheetlike motif. J. Am. Chem. Soc. 126: 6204-6205.
70. Sansone, F., S. Barboso, A. Casnati, D. Sciotto, and R. Ungaro, R. 1999. A new chiral rigid cone water soluble peptidocalix[4]arene and its inclusion complexes with a-amino acids and aromatic ammonium cations. Tetrahedron Lett. 40: 4741-4744.
71. Sdira, S. B., C. P. Felix, M.-B. A. Giudicelli, P. F. Seigle-Ferrand, M. Perrin, and R. J. Lamartine. 2003. Synthesis and structure of lower rim C-linked N-tosyl peptidocalix[4]- arenes. J. Org. Chem. 68: 6632-6638.
72. Sidorov, V., F. W. Kotch, G. Abdrakhmanova, R. Mizani, J. C. Fettinger, and J. T. Davis. 2002. Ion channel formation from a calix[4]arene amide that binds HCl. J. Am. Chem. Soc. 124: 2267-2278.
73. Sirit, A., and M. Yilmaz. 2009. Chiral Calixarenes. Turk. J. Chem. 33: 159-200.
74. Sisson, A. L., M. Raza Shah, S. Bhosale, and S. Matile. 2006. Synthetic ion channel and pores (2004-2005). Chem. Soc. Rev. 35: 1269-1286.
75. Tabushi, I., Y.Y. Kuroda and K. Yokota. 1982. A, B, D, F - tetrasubstituted b-cyclodextrin as artificial channel compound. Tetrahedron Lett. 23: 4601-4604.
76. Thallapally, P. K., G. O Lloyd, J. L. Atwood, and L. J. Barbour. 2005. Diffusion of water in a nonporous hydrophobic crystal. Angew. Chem. Int. Ed. 44: 3848-3851.
77. Van Beijnen, A. J. M., R. J. M. Nolte, and J. W. Zwikker. 1982. A molecular cationic channel. Recl. Trav. Chim. Pays-Bas. 101: 409-410.
78. Vicens, J., and J. Harrowfield. 2007. Calixarene in the Nanoworld. Dordrecht: Springer.
79. Voyer, N., L. Potvin, and E. Rousseau. 1997. Electrical activity of artificial ion channel incorporated into planar lipid bilayers. J. Chem. Soc., Perkin Trans. 2: 1469-1471.
80. Weber, M. E., E. K. Elliot, and G. W. Gokel. 2006. Activity of synthetic ion channels is influenced by cation-p interactions with phospholipid headgroups. Org. Biomol. Chem. 4: 83-89.
81. Wright, A. J., S. E. Mattews, W. B. Fischer, and P. D. Beer. 2001. Novel resorcin[4]- arenes as potassium-selective ion-channel and transporter mimics. Chem. Eur. J. 7: 3474-3481.
82. Yoshino, N., A. Satake, and Y. Kokuke. 2001. An artificial ion channel formed by a macrocyclic resorcin[4]arene with amphiphilic cholic acid ether groups. Angew. Chem. Int. Ed. 40: 457-459.