Conformationally controlled oligocholate membrane transporters: Learning through water play

Accounts of Chemical Research

Volumn 46, Issue 12, 2013, Pages 2763-2772

  Zhao, Yan ^a   Cho, Hongkwan ^a   Widanapathirana, Lakmini ^a   Zhang, Shiyong ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84890588662     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar300337f     Document Type: Article

References (66)

1. Stein, W. D. Carriers and Pumps: An Introduction to Membrane Transport; Academic Press: San Diego, CA, 1990.
2. McNally, B. A.; O'Neil, E. J.; Nguyen, A.; Smith, B. D. Membrane Transporters for Anions That Use a Relay Mechanism J. Am. Chem. Soc. 2008, 130, 17274
3. Davis, A. P.; Walsh, J. J. Steroid-Based Receptors with Tunable Cavities; Stepwise and Direct Syntheses of a C-3-Symmetrical Prototype Chem. Commun. 1996, 449-451 (Pubitemid 26068706)
4. Brady, P. A.; Bonar-Law, R. P.; Rowan, S. J.; Suckling, C. J.; Sanders, J. K. M. "Living" Macrolactonisation: Thermodynamically-Controlled Cyclisation and Interconversion of Oligocholates Chem. Commun. 1996, 319-320 (Pubitemid 126443236)
5. Virtanen, E.; Kolehmainen, E. Use of Bile Acids in Pharmacological and Supramolecular Applications Eur. J. Org. Chem. 2004, 2004, 3385-3399
6. - Interactions: A New Motif for Anion Coordination? Org. Lett. 2005, 7, 1441-1444 (Pubitemid 40585901)
7. Brotherhood, P. R.; Davis, A. P. Steroid-Based Anion Receptors and Transporters Chem. Soc. Rev. 2010, 39, 3633-3647
8. Zhang, J. W.; Luo, J. T.; Zhu, X. X.; Junk, M. J. N.; Hinderberger, D. Molecular Pockets Derived from Cholic Acid as Chemosensors for Metal Ions Langmuir 2010, 26, 2958-2962
9. Goto, C.; Yamamura, M.; Satake, A.; Kobuke, Y. Artificial Ion Channels Showing Rectified Current Behavior J. Am. Chem. Soc. 2001, 123, 12152-12159 (Pubitemid 33136052)
10. Bandyopadhyay, P.; Janout, V.; Zhang, L. H.; Sawko, J. A.; Regen, S. L. An Ion Conductor Derived from Spermine and Cholic Acid J. Am. Chem. Soc. 2000, 122, 12888-12889 (Pubitemid 32052228)
11. Maulucci, N.; De Riccardis, F.; Botta, C. B.; Casapullo, A.; Cressina, E.; Fregonese, M.; Tecilla, P.; Izzo, I. Calix[4]Arene-Cholic Acid Conjugates: A New Class of Efficient Synthetic Ionophores Chem. Commun. 2005, 1354-1356 (Pubitemid 40459998)
12. Wilson, C. P.; Webb, S. J. Palladium(II)-Gated Ion Channels Chem. Commun. 2008, 4007-4009
13. Ma, L.; Melegari, M.; Colombini, M.; Davis, J. T. Large and Stable Transmembrane Pores from Guanosine-Bile Acid Conjugates J. Am. Chem. Soc. 2008, 130, 2938-2939 (Pubitemid 351455956)
14. Janout, V.; Di Giorgio, C.; Regen, S. L. Molecular Umbrella-Assisted Transport of a Hydrophilic Peptide across a Phospholipid Membrane J. Am. Chem. Soc. 2000, 122, 2671-2672 (Pubitemid 30211991)
15. Janout, V.; Jing, B. W.; Staina, I. V.; Regen, S. L. Selective Transport of ATP across a Phospholipid Bilayer by a Molecular Umbrella J. Am. Chem. Soc. 2003, 125, 4436-4437 (Pubitemid 36418687)
16. Janout, V.; Regen, S. L. A Needle-and-Thread Approach to Bilayer Transport: Permeation of a Molecular Umbrella-Oligonucleotide Conjugate across a Phospholipid Membrane J. Am. Chem. Soc. 2005, 127, 22-23 (Pubitemid 40094345)
17. Koulov, A. V.; Lambert, T. N.; Shukla, R.; Jain, M.; Boon, J. M.; Smith, B. D.; Li, H. Y.; Sheppard, D. N.; Joos, J. B.; Clare, J. P.; Davis, A. P. Chloride Transport across Vesicle and Cell Membranes by Steroid-Based Receptors Angew. Chem., Int. Ed. 2003, 42, 4931-4933 (Pubitemid 37345394)
18. Whitmarsh, S. D.; Redmond, A. P.; Sgarlata, V.; Davis, A. P. Cationic Cyclocholamides; Toroidal Facial Amphiphiles with Potential for Anion Transport Chem. Commun. 2008, 3669-3671
19. Chothia, C.; Janin, J. Principles of Protein-Protein Recognition Nature 1975, 256, 705-708
20. Danielsson, H.; Sjövall, J. Sterols and Bile Acids; Elsevier: Amsterdam, 1985.
21. Ryu, E.-H.; Zhao, Y. Environmentally Responsive Molecular Baskets: Unimolecular Mimics of Both Micelles and Reversed Micelles Org. Lett. 2004, 6, 3187-3189 (Pubitemid 39233151)
22. Ryu, E.-H.; Yan, J.; Zhong, Z.; Zhao, Y. Solvent-Induced Amphiphilic Molecular Baskets: Unimolecular Reversed Micelles with Different Size, Shape, and Flexibility J. Org. Chem. 2006, 71, 7205-7213 (Pubitemid 44452898)
23. Ryu, E.-H.; Zhao, Y. An Amphiphilic Molecular Basket Sensitive to Both Solvent Changes and UV Irradiation J. Org. Chem. 2006, 71, 9491-9494 (Pubitemid 44924533)
24. Zhao, Y.; Ryu, E.-H. Solvent-Tunable Binding of Hydrophilic and Hydrophobic Guests by Amphiphilic Molecular Baskets J. Org. Chem. 2005, 70, 7585-7591 (Pubitemid 41318518)
25. Cho, H.; Zhao, Y. Cholate-Derived Amphiphilic Molecular Baskets as Glucose Transporters across Lipid Membranes Chem. Commun. 2011, 47, 8970-8972
26. Granja, J. R.; Ghadiri, M. R. Channel-Mediated Transport of Glucose across Lipid Bilayers J. Am. Chem. Soc. 1994, 116, 10785-10786
27. Westmark, P. R.; Smith, B. D. Boronic Acids Selectively Facilitate Glucose-Transport through a Lipid Bilayer J. Am. Chem. Soc. 1994, 116, 9343-9344 (Pubitemid 24336959)
28. Westmark, P. R.; Gardiner, S. J.; Smith, B. D. Selective Monosaccharide Transport through Lipid Bilayers Using Boronic Acid Carriers J. Am. Chem. Soc. 1996, 118, 11093-11100 (Pubitemid 26399733)
29. Silverman, M. Structure and Function of Hexose Transporters Annu. Rev. Biochem. 1991, 60, 757-794
30. Lienhard, G. E.; Slot, J. W.; James, D. E.; Mueckler, M. M. How Cells Absorb Glucose? Sci. Am. 1992, 266, 86-91
31. Mueckler, M. Facilitative Glucose Transporters Eur. J. Biochem. 1994, 219, 713-725 (Pubitemid 24050938)
32. Manolescu, A. R.; Witkowska, K.; Kinnaird, A.; Cessford, T.; Cheeseman, C. Facilitated Hexose Transporters: New Perspectives on Form and Function Physiology 2007, 22, 234-240
33. Zhao, Y.; Zhong, Z. Oligomeric Cholates: Amphiphilic Foldamers with Nanometer-Sized Hydrophilic Cavities J. Am. Chem. Soc. 2005, 127, 17894-17901 (Pubitemid 43003402)
34. Zhao, Y.; Zhong, Z.; Ryu, E.-H. Preferential Solvation within Hydrophilic Nanocavities and Its Effect on the Folding of Cholate Foldamers J. Am. Chem. Soc. 2007, 129, 218-225 (Pubitemid 46084815)
35. Zhao, Y.; Zhong, Z. Tuning the Sensitivity of a Foldamer-Based Mercury Sensor by Its Folding Energy J. Am. Chem. Soc. 2006, 128, 9988-9989 (Pubitemid 44201064)
36. 2+ in Aqueous Solutions with a Foldamer-Based Fluorescent Sensor Modulated by Surfactant Micelles Org. Lett. 2006, 8, 4715-4717 (Pubitemid 44629443)
37. 2+ Org. Lett. 2007, 9, 2891-2894
38. Cho, H.; Zhong, Z.; Zhao, Y. A DMAP-Functionalized Oligocholate Foldamer for Solvent-Responsive Catalysis Tetrahedron 2009, 65, 7311-7316
39. Pan, X.; Zhao, Y. Efficient Construction of Oligocholate Foldamers via "Click" Chemistry and Their Tolerance of Structural Heterogeneity Org. Lett. 2009, 11, 69-72
40. Cho, H.; Zhao, Y. Environmental Effects Dominate the Folding of Oligocholates in Solution, Surfactant Micelles, and Lipid Membranes J. Am. Chem. Soc. 2010, 132, 9890-9899
41. Zhong, Z.; Zhao, Y. Controlling the Conformation of Oligocholate Foldamers by Surfactant Micelles J. Org. Chem. 2008, 73, 5498-5505
42. Zhao, Y. Conformation of Oligocholate Foldamers with 4-Aminobutyroyl Spacers J. Org. Chem. 2009, 74, 834-843
43. Zhao, Y. Spacer-Dependent Folding and Aggregation of Oligocholates in SDS Micelles J. Org. Chem. 2009, 74, 7470-7480
44. Zhang, S.; Zhao, Y. Effects of Micelle Properties on the Conformation of Oligocholates and Importance of Rigidity of Foldamers J. Org. Chem. 2011, 77, 556-562
45. Zhang, S.; Zhao, Y. Oligocholate Foldamers as Carriers for Hydrophilic Molecules across Lipid Bilayers Chem.-Eur. J. 2011, 17, 12444-12451
46. Widanapathirana, L.; Zhao, Y. Effects of Amphiphile Topology on the Aggregation of Oligocholates in Lipid Membranes: Macrocyclic Versus Linear Amphiphiles Langmuir 2012, 28, 8165-8173
47. Zhang, S. Y.; Zhao, Y. Flexible Oligocholate Foldamers as Membrane Transporters and Their Guest-Dependent Transport Mechanism Org. Biomol. Chem. 2012, 10, 260-266
48. Wu, J.; Pan, X.; Zhao, Y. Time-Dependent Shrinkage of Polymeric Micelles of Amphiphilic Block Copolymers Containing Semirigid Oligocholate Hydrophobes J. Colloid Interface Sci. 2011, 353, 420-425
49. Sisson, A. L.; Shah, M. R.; Bhosale, S.; Matile, S. Synthetic Ion Channels and Pores (2004-2005) Chem. Soc. Rev. 2006, 35, 1269-1286
50. Gokel, G. W.; Carasel, I. A. Biologically Active, Synthetic Ion Transporters Chem. Soc. Rev. 2007, 36, 378-389
51. Fyles, T. M. Synthetic Ion Channels in Bilayer Membranes Chem. Soc. Rev. 2007, 36, 335-347
52. McNally, B. A.; Leevy, W. M.; Smith, B. D. Recent Advances in Synthetic Membrane Transporters Supramol. Chem. 2007, 19, 29-37
53. Li, X.; Wu, Y. D.; Yang, D. Alpha-Aminoxy Acids: New Possibilities from Foldamers to Anion Receptors and Channels Acc. Chem. Res. 2008, 41, 1428-1438
54. Davis, J. T.; Okunola, O.; Quesada, R. Recent Advances in the Transmembrane Transport of Anions Chem. Soc. Rev. 2010, 39, 3843-3862
55. Litvinchuk, S.; Sorde, N.; Matile, S. Sugar Sensing with Synthetic Multifunctional Pores J. Am. Chem. Soc. 2005, 127, 9316-9317 (Pubitemid 40934715)
56. Sakai, N.; Sorde, N.; Matile, S. Synthetic Catalytic Pores J. Am. Chem. Soc. 2003, 125, 7776-7777 (Pubitemid 36782135)
57. Dunitz, J. D. The Entropic Cost of Bound Water in Crystals and Biomolecules Science 1994, 264, 670 (Pubitemid 24186849)
58. Lewis, B. A.; Engelman, D. M. Bacteriorhodopsin Remains Dispersed in Fluid Phospholipid-Bilayers over a Wide-Range of Bilayer Thicknesses J. Mol. Biol. 1983, 166, 203-210
59. Nezil, F. A.; Bloom, M. Combined Influence of Cholesterol and Synthetic Amphiphillic Peptides Upon Bilayer Thickness in Model Membranes Biophys. J. 1992, 61, 1176-1183
60. Cho, H.; Widanapathirana, L.; Zhao, Y. Water-Templated Transmembrane Nanopores from Shape-Persistent Oligocholate Macrocycles J. Am. Chem. Soc. 2011, 133, 141-147
61. Cho, H.; Zhao, Y. Translocation of Hydrophilic Molecules across Lipid Bilayers by Salt-Bridged Oligocholates Langmuir 2011, 27, 4936-4944
62. Wang, T.; Widanapathirana, L.; Zhao, Y.; Hong, M. Aggregation and Dynamics of Oligocholate Transporters in Phospholipid Bilayers Revealed by Solid-State NMR Spectroscopy Langmuir 2012, 28, 17071-17078
63. Widanapathirana, L.; Zhao, Y. Aromatically Functionalized Cyclic Tricholate Macrocycles: Aggregation, Transmembrane Pore Formation, Flexibility, and Cooperativity J. Org. Chem. 2012, 77, 4679-4687
64. 1H NMR Investigation of Solvent Effects in Aromatic Stacking Interactions J. Am. Chem. Soc. 2001, 123, 7560-7563 (Pubitemid 32899392)
65. Widanapathirana, L.; Li, X.; Zhao, Y. Hydrogen Bond-Assisted Macrocyclic Oligocholate Transporters in Lipid Membranes Org. Biomol. Chem. 2012, 10, 5077-5083
66. Kamp, F.; Hamilton, J. A. pH Gradients across Phospholipid-Membranes Caused by Fast Flip-Flop of Unionized Fatty-Acids Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 11367-11370