Synthetic ion transporters that work with anion-π interactions, halogen bonds, and anion-macrodipole interactions

Accounts of Chemical Research

Volumn 46, Issue 12, 2013, Pages 2791-2800

  Vargas Jentzsch, Andreas ^a   Hennig, Andreas ^a   Mareda, Jiri ^a   Matile, Stefan ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84888602598     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar400014r     Document Type: Article

References (53)

1. Matile, S.; Som, A.; Sordé, N. Recent Synthetic Ion Channels and Pores Tetrahedron 2004, 60, 6405-6435 (Pubitemid 39090238)
2. Sisson, A. L.; Shah, M. R.; Bhosale, S.; Matile, S. Synthetic Ion Channels and Pores (2004-2005) Chem. Soc. Rev. 2006, 35, 1269-1286
3. Matile, S.; Vargas Jentzsch, A.; Fin, A.; Montenegro, J. Recent Synthetic Transport Systems Chem. Soc. Rev. 2011, 40, 2453-2474
4. Chui, J. K.; Fyles, T. M. Ionic Conductance of Synthetic Channels: Analysis, Lessons, and Recommendations Chem. Soc. Rev. 2012, 41, 148-175
5. Davis, J. T.; Okunola, O.; Quesada, R. Recent Advances in the Transmembrane Transport of Anions Chem. Soc. Rev. 2010, 39, 3843-3862
6. Davis, A. P.; Sheppard, D. N.; Smith, B. D. Development of Synthetic Membrane Transporters for Anions Chem. Soc. Rev. 2007, 36, 348-357
7. Gale, P. A. From Anion Receptors to Transporters Acc. Chem. Res. 2011, 44, 216-226
8. Gokel, G. W.; Barkey, N. Transport of Chloride Ion Through Phospholipid Bilayers Mediated by Synthetic Ionophores New J. Chem. 2009, 33, 947-963
9. Fyles, T. M.; Matile, S., Eds. Synthetic Transport Systems in Lipid Bilayer Membranes. Acc. Chem. Res., this issue.
10. Sakai, N.; Mareda, J.; Matile, S. Rigid-Rod Molecules in Biomembrane Models: From Hydrogen-Bonded Chains to Synthetic Multifunctional Pores Acc. Chem. Res. 2005, 38, 79-87 (Pubitemid 40261718)
11. Gorteau, V.; Bollot, G.; Mareda, J.; Perez-Velasco, A.; Matile, S. Rigid Oligonaphthalenediimide Rods as Transmembrane Anion-π Slides J. Am. Chem. Soc. 2006, 128, 14788-14789 (Pubitemid 44851601)
12. Perez-Velasco, A.; Gorteau, V.; Matile, S. Rigid Oligoperylenediimide Rods: Anion-π Slides with Photosynthetic Activity Angew. Chem., Int. Ed. 2008, 47, 921-923 (Pubitemid 351160286)
13. Sakai, N.; Mareda, J.; Matile, S. Artificial β-Barrels Acc. Chem. Res. 2008, 41, 1354-1365
14. Das, G.; Talukdar, P.; Matile, S. Fluorometric Detection of Enzyme Activity with Synthetic Supramolecular Pores Science 2002, 298, 1600-1602 (Pubitemid 35387194)
15. Litvinchuk, S.; Tanaka, H.; Miyatake, T.; Pasini, D.; Tanaka, T.; Bollot, G.; Mareda, J.; Matile, S. Synthetic Pores with Reactive Signal Amplifiers as Artificial Tongues Nat. Mater. 2007, 6, 576-580 (Pubitemid 47201993)
16. 6 and Phytate Sensing in Complex Matrices J. Am. Chem. Soc. 2008, 130, 3270-3271 (Pubitemid 351456014)
17. Hagihara, S.; Tanaka, H.; Matile, S. Boronic Acid Converters for Reactive Hydrazide Amplifiers: Polyphenol Sensing in Green Tea with Synthetic Pores J. Am. Chem. Soc. 2008, 130, 5656-5657 (Pubitemid 351600491)
18. Butterfield, S. M.; Miyatake, T.; Matile, S. Amplifier-Mediated Activation of Cell Penetrating Peptides with Steroids: Multifunctional Anion Transporters for Fluorogenic Cholesterol Sensing in Eggs and Blood Angew. Chem., Int. Ed. 2009, 48, 325-328
19. Takeuchi, T.; Matile, S. DNA Aptamers as Analyte-Responsive Cation Transporters in Fluorogenic Vesicles: Signal Amplification by Supramolecular Polymerization J. Am. Chem. Soc. 2009, 131, 18048-18049
20. Takeuchi, T.; Montenegro, J.; Hennig, A.; Matile, S. Pattern Generation with Synthetic Sensing Systems in Lipid Bilayer Membranes Chem. Sci. 2011, 2, 303-307
21. Bhosale, S.; Sisson, A. L.; Talukdar, P.; Fürstenberg, A.; Banerji, N.; Vauthey, E.; Bollot, G.; Mareda, J.; Röger, C.; Würthner, F.; Sakai, N.; Matile, S. Photoproduction of Proton Gradients with π-Stacked Fluorophore Scaffolds in Lipid Bilayers Science 2006, 313, 84-86 (Pubitemid 44051257)
22. Winum, J.-Y.; Matile, S. Rigid Push-Pull Oligo(p -Phenylene) Rods: Depolarization of Bilayer Membranes with Negative Membrane Potential J. Am. Chem. Soc. 1999, 121, 7961-7962 (Pubitemid 29420529)
23. Sakai, N.; Matile, S. Recognition of Polarized Bilayer Membranes by p -Oligophenyl Ion Channels: From Push-Pull Rods to Push-Pull β-Barrels J. Am. Chem. Soc. 2002, 124, 1184-1185 (Pubitemid 34169122)
24. Sakai, N.; Houdebert, D.; Matile, S. Voltage-Dependent Formation of Anion Channels by Synthetic Rigid-Rod Push-Pull β-Barrels Chem.-Eur. J. 2003, 9, 223-232
25. Baudry, Y.; Pasini, D.; Nishihara, M.; Sakai, N.; Matile, S. The Depth of Molecular Recognition: Voltage-Sensitive Blockage of Synthetic Multifunctional Pores with Refined Architecture Chem. Commun. 2005, 40, 4798-4800 (Pubitemid 41503192)
26. Sakai, N.; Baumeister, B.; Matile, S. Transmembrane B-DNA ChemBioChem 2000, 1, 123-125
27. Sakai, N.; Sordé, N.; Matile, S. Synthetic Catalytic Pores J. Am. Chem. Soc. 2003, 125, 7776-7777 (Pubitemid 36782135)
28. Dawson, R. E.; Hennig, A.; Weimann, D. P.; Emery, D.; Ravikumar, V.; Montenegro, J.; Takeuchi, T.; Gabutti, S.; Mayor, M.; Mareda, J.; Schalley, C. A.; Matile, S. Experimental Evidence for the Functional Relevance of Anion-π Interactions Nat. Chem. 2010, 2, 533-538
29. Misek, J.; Vargas Jentzsch, A.; Sakurai, S.; Emery, D.; Mareda, J.; Matile, S. A Chiral and Colorful Redox Switch: Enhanced π Acidity in Action Angew. Chem., Int. Ed. 2010, 49, 7680-7683
30. Lin, N.-T.; Vargas Jentzsch, A.; Guénée, L.; Neudörfl, J.-M.; Aziz, S.; Berkessel, A.; Orentas, E.; Sakai, N.; Matile, S. Enantioselective Self-Sorting on Planar, π-Acidic Surfaces of Anion-π Transporters Chem. Sci. 2012, 3, 1121-1127
31. Vargas Jentzsch, A.; Emery, D.; Mareda, J.; Metrangolo, P.; Resnati, G.; Matile, S. Ditopic Ion Transport Systems: Anion-π Interactions and Halogen Bonds at Work Angew. Chem., Int. Ed. 2011, 50, 11675-11678
32. Vargas Jentzsch, A.; Emery, D.; Mareda, J.; Nayak, S. K.; Metrangolo, P.; Resnati, G.; Sakai, N.; Matile, S. Transmembrane Anion Transport Mediated by Halogen-Bond Donors Nat. Commun. 2012, 3, 905
33. Hennig, A.; Fischer, L.; Guichard, G.; Matile, S. Anion-Macrodipole Interactions: Self-Assembling, Macrocyclic Oligourea/Amide Anion Transporters that Respond to Membrane Polarization J. Am. Chem. Soc. 2009, 131, 16889-16895
34. Frontera, A.; Gamez, P.; Mascal, M.; Mooibroek, T. J.; Reedijk, J. Putting Anion-π Interactions Into Perspective Angew. Chem., Int. Ed. 2011, 50, 9564-9583
35. Schottel, B. L.; Chifotides, H. T.; Dunbar, K. R. Anion-π Interactions Chem. Soc. Rev. 2008, 37, 68-83
36. Ballester, P. Experimental Quantification of Anion-π Interactions in Solution Using Neutral Host-Guest Model Systems. Acc. Chem. Res., in press.
37. a Values Beilstein J. Org. Chem. 2011, 7, 320-328
38. Giese, M.; Albrecht, M.; Wiemer, K.; Kubik, G.; Valkonen, A.; Rissanen, K. Weak Intermolecular Anion-π Interactions in Pentafluorobenzyl-Substituted Ammonium Betaines Eur. J. Inorg. Chem. 2012, 2995-2999
39. Bhosale, S.; Matile, S. A Simple Method to Identify Supramolecules in Action: Hill Coefficients for Exergonic Self-Assembly Chirality 2006, 18, 849-856 (Pubitemid 44619178)
40. Stadler, E.; Dedek, P.; Yamashita, K.; Regen, S. L.; Amphotericin, B. Mimics: A Sterol-Based Ionophore J. Am. Chem. Soc. 1994, 116, 6677-6682
41. Chang, J.; Ye, Q.; Huang, K.-W.; Zhang, J.; Chen, Z.-K.; Wu, J.; Chi, C. Stepwise Cyanation of Naphthalene Diimide for n-Channel Field-Effect Transistors Org. Lett. 2012, 14, 2964-2967
42. Behr, J.-P.; Kirch, M.; Lehn, J.-M. Carrier-Mediated Transport Through Bulk Liquid Membranes: Dependence of Transport Rates and Selectivity on Carrier Properties in a Diffusion-Limited Process J. Am. Chem. Soc. 1985, 107, 241-246
43. Ponnuswamy, N.; Pantoş, G. D.; Smulders, M. M. J.; Sanders, J. M. K. Thermodynamics of Supramolecular Naphthalenediimide Nanotube Formation: The Influence of Solvents, Side Chains, and Guest Templates J. Am. Chem. Soc. 2012, 134, 566-573
44. Cavallo, G.; Metrangolo, P.; Pilati, T.; Resnati, G.; Sansotera, M.; Terraneo, G. Halogen Bonding: A General Route in Anion Recognition and Coordination Chem. Soc. Rev. 2010, 39, 3772-3783
45. Zapata, F.; Caballero, A.; White, N. G.; Claridge, T. D. W.; Costa, P. J.; Félix, V.; Beer, P. D. Fluorescent Charge-Assisted Halogen-Bonding Macrocyclic Halo-Imidazolium Receptors for Anion Recognition and Sensing in Aqueous Media J. Am. Chem. Soc. 2012, 134, 11533-11541
46. Chudzinski, M. G.; McClary, C. A.; Taylor, M. S. Anion Receptors Composed of Hydrogen- and Halogen-Bond Donor Groups: Modulating Selectivity with Combinations of Distinct Noncovalent Interactions J. Am. Chem. Soc. 2011, 113, 10559-10567
47. Hardegger, L. A.; Kuhn, B.; Spinnler, B.; Anselm, L.; Ecabert, R.; Stihle, M.; Gsell, B.; Thoma, R.; Diez, J.; Benz, J.; Plancher, J. M.; Hartmann, G.; Banner, D. W.; Haap, W.; Diederich, F. Systematic Investigation of Halogen Bonding in Protein-Ligand Interactions Angew. Chem., Int. Ed. 2011, 50, 314-318
48. Auffinger, P.; Hays, F. A.; Westhof, E.; Ho, P. S. Halogen Bonds in Biological Molecules Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 16789-16794 (Pubitemid 39601317)
49. Bruckmann, A.; Pena, M. A.; Bolm, C. Organocatalysis through Halogen-Bond Activation Synlett 2008, 6, 900-902 (Pubitemid 351518056)
50. Fischer, L.; Guichard, G. Folding and Self-Assembly of Aromatic and Aliphatic Urea Oligomers: Towards Connecting Structure and Function Org. Biomol. Chem. 2010, 8, 3101-3117
51. Ma, J. C.; Dougherty, D. A. The Cation-π Interaction Chem. Rev. 1997, 97, 1303-1324
52. Knowles, R. R.; Lin, S.; Jacobsen, E. N. Enantioselective Thiourea-Catalyzed Cationic Polycyclizations J. Am. Chem. Soc. 2010, 132, 5030-5032
53. Vargas Jentzsch, A.; Matile, S. Transmembrane Halogen-Bonding Cascades J. Am. Chem. Soc. 2013, DOI: 10.1021/ja4013276