Oligocholate foldamers as carriers for hydrophilic molecules across lipid bilayers

Chemistry - A European Journal

Volumn 17, Issue 44, 2011, Pages 12444-12451

  Zhang, Shiyong ^a   Zhao, Yan ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

conformation analysis; foldamers; membranes; oligocholates; transporters

Indexed keywords

CARBOXYFLUORESCEIN; CLICK REACTION; CONFORMATION ANALYSIS; CONFORMATIONAL PROPERTIES; CONFORMATIONAL STUDY; FOLDAMERS; FOLDED STRUCTURES; HELICAL CONFORMATION; HYDROPHILIC MOLECULES; INTERNAL CAVITIES; NONPOLAR ENVIRONMENT; OLIGOCHOLATES; SINGLE BOND; TRANSPORT RATE; TRANSPORTERS; UV/ VIS SPECTROSCOPY;

AMPHIPHILES; CONFORMATIONS; HYDROPHILICITY; HYDROPHOBICITY; MOLECULES; OLIGOMERS; ORGANIC SOLVENTS; SYNTHESIS (CHEMICAL);

LIPID BILAYERS;

CHOLIC ACID DERIVATIVE;

ARTICLE; CHEMICAL PHENOMENA; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; LIPID BILAYER; SOLUTION AND SOLUBILITY; SYNTHESIS; TRANSPORT AT THE CELLULAR LEVEL;

BIOLOGICAL TRANSPORT; CHOLATES; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; LIPID BILAYERS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; SOLUTIONS;

EID: 80054744508     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201101510     Document Type: Article

References (85)

1. S. H. Gellman, Acc. Chem. Res. 1998, 31, 173-180
2. D. J. Hill, M. J. Mio, R. B. Prince, T. S. Hughes, J. S. Moore, Chem. Rev. 2001, 101, 3893-4012
3. S. Hecht, I. Huc, in Foldamers: Structure, Properties, and Applications, Wiley-VCH, Weinheim, 2007
4. M. S. Cubberley, B. L. Iverson, Curr. Opin. Chem. Biol. 2001, 5, 650-653
5. K. Kirshenbaum, R. N. Zuckermann, K. A. Dill, Curr. Opin. Struct. Biol. 1999, 9, 530-535
6. C. M. Goodman, S. Choi, S. Shandler, W. F. DeGrado, Nat. Chem. Biol. 2007, 3, 252-262
7. A. D. Bautista, C. J. Craig, E. A. Harker, A. Schepartz, Curr. Opin. Chem. Biol. 2007, 11, 685-692.
8. E. A. Porter, B. Weisblum, S. H. Gellman, J. Am. Chem. Soc. 2002, 124, 7324-7330
9. B. P. Mowery, S. E. Lee, D. A. Kissounko, R. F. Epand, R. M. Epand, B. Weisblum, S. S. Stahl, S. H. Gellman, J. Am. Chem. Soc. 2007, 129, 15474-15476
10. N. P. Chongsiriwatana, J. A. Patch, A. M. Czyzewski, M. T. Dohm, A. Ivankin, D. Gidalevitz, R. N. Zuckermann, A. E. Barron, Proc. Natl. Acad. Sci. USA 2008, 105, 2794-2799
11. S. Choi, A. Isaacs, D. Clements, D. Liu, H. Kim, R. W. Scott, J. D. Winkler, W. F. DeGrado, Proc. Natl. Acad. Sci. USA 2009, 106, 6968-6973
12. G. N. Tew, R. W. Scott, M. L. Klein, W. F. DeGrado, Acc. Chem. Res. 2010, 43, 30-39.
13. J. M. Rodriguez, A. D. Hamilton, Angew. Chem. 2007, 119, 8768-8771
14. Angew. Chem. Int. Ed. 2007, 46, 8614-8617
15. P. N. Wyrembak, A. D. Hamilton, J. Am. Chem. Soc. 2009, 131, 4566-4567
16. W. S. Horne, L. M. Johnson, T. J. Ketas, P. J. Klasse, M. Lu, J. P. Moore, S. H. Gellman, Proc. Natl. Acad. Sci. USA 2009, 106, 14751-14756
17. Y. Imamura, N. Watanabe, N. Umezawa, T. Iwatsubo, N. Kato, T. Tomita, T. Higuchi, J. Am. Chem. Soc. 2009, 131, 7353-7359.
18. W. Cai, G. T. Wang, Y. X. Xu, X. K. Jiang, Z. T. Li, J. Am. Chem. Soc. 2008, 130, 6936-6937.
19. G. Maayan, M. D. Ward, K. Kirshenbaum, Proc. Natl. Acad. Sci. USA 2009, 106, 13679-13684.
20. W. D. Stein, Carriers and Pumps: An Introduction to Membrane Transport, Academic Press, San Diego, 1990
21. G. W. Gokel, I. A. Carasel, Chem. Soc. Rev. 2007, 36, 378-389
22. T. M. Fyles, Chem. Soc. Rev. 2007, 36, 335-347
23. B. A. McNally, W. M. Leevy, B. D. Smith, Supramol. Chem. 2007, 19, 29-37
24. J. T. Davis, O. Okunola, R. Quesada, Chem. Soc. Rev. 2010, 39, 3843-3862.
25. S. Litvinchuk, N. Sorde, S. Matile, J. Am. Chem. Soc. 2005, 127, 9316-9317.
26. J. J. Kasianowicz, E. Brandin, D. Branton, D. W. Deamer, Proc. Natl. Acad. Sci. USA 1996, 93, 13770-13773
27. M. Akeson, D. Branton, J. J. Kasianowicz, E. Brandin, D. W. Deamer, Biophys. J. 1999, 77, 3227-3233
28. A. Meller, L. Nivon, E. Brandin, J. Golovchenko, D. Branton, Proc. Natl. Acad. Sci. USA 2000, 97, 1079-1084
29. W. Vercoutere, S. Winters-Hilt, H. Olsen, D. Deamer, D. Haussler, M. Akeson, Nat. Biotechnol. 2001, 19, 248-252
30. S. Howorka, S. Cheley, H. Bayley, Nat. Biotechnol. 2001, 19, 636-639
31. J. Clarke, H. C. Wu, L. Jayasinghe, A. Patel, S. Reid, H. Bayley, Nat. Nanotechnol. 2009, 4, 265-270.
32. N. Sakai, N. Sorde, S. Matile, J. Am. Chem. Soc. 2003, 125, 7776-7777.
33. Y. Zhao, Z. Zhong, J. Am. Chem. Soc. 2005, 127, 17894-17901
34. H. K. Cho, Z. Q. Zhong, Y. Zhao, Tetrahedron 2009, 65, 7311-7316
35. Y. Zhao, J. Org. Chem. 2009, 74, 834-843.
36. H. Danielsson, J. Sjövall, Sterols and Bile Acids, Elsevier, Amsterdam, 1985.
37. L. Ma, M. Melegari, M. Colombini, J. T. Davis, J. Am. Chem. Soc. 2008, 130, 2938-2939
38. P. Bandyopadhyay, V. Janout, L. H. Zhang, J. A. Sawko, S. L. Regen, J. Am. Chem. Soc. 2000, 122, 12888-12889
39. C. Goto, M. Yamamura, A. Satake, Y. Kobuke, J. Am. Chem. Soc. 2001, 123, 12152-12159
40. N. Maulucci, F. De Riccardis, C. B. Botta, A. Casapullo, E. Cressina, M. Fregonese, P. Tecilla, I. Izzo, Chem. Commun. 2005, 1354-1356
41. C. P. Wilson, S. J. Webb, Chem. Commun. 2008, 4007-4009.
42. V. Janout, C. Di Giorgio, S. L. Regen, J. Am. Chem. Soc. 2000, 122, 2671-2672
43. V. Janout, I. V. Staina, P. Bandyopadhyay, S. L. Regen, J. Am. Chem. Soc. 2001, 123, 9926-9927
44. V. Janout, B. W. Jing, I. V. Staina, S. L. Regen, J. Am. Chem. Soc. 2003, 125, 4436-4437
45. V. Janout, S. L. Regen, J. Am. Chem. Soc. 2005, 127, 22-23.
46. A. V. Koulov, T. N. Lambert, R. Shukla, M. Jain, J. M. Boon, B. D. Smith, H. Y. Li, D. N. Sheppard, J. B. Joos, J. P. Clare, A. P. Davis, Angew. Chem. 2003, 115, 5081-5083
47. Angew. Chem. Int. Ed. 2003, 42, 4931-4933
48. S. D. Whitmarsh, A. P. Redmond, V. Sgarlata, A. P. Davis, Chem. Commun. 2008, 3669-3671.
49. H. Cho, Y. Zhao, J. Am. Chem. Soc. 2010, 132, 9890-9899
50. H. Cho, L. Widanapathirana, Y. Zhao, J. Am. Chem. Soc. 2011, 133, 141-147
51. H. Cho, Y. Zhao, Langmuir 2011, 27, 4936-4944.
52. G. W. Gokel, O. Murillo, Acc. Chem. Res. 1996, 29, 425-432
53. G. W. Gokel, A. Mukhopadhyay, Chem. Soc. Rev. 2001, 30, 274-286
54. S. Matile, A. Som, N. Sorde, Tetrahedron 2004, 60, 6405-6435
55. N. Sakai, J. Mareda, S. Matile, Acc. Chem. Res. 2005, 38, 79-87
56. A. L. Sisson, M. R. Shah, S. Bhosale, S. Matile, Chem. Soc. Rev. 2006, 35, 1269-1286.
57. V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem. 2002, 114, 2708-2711
58. Angew. Chem. Int. Ed. 2002, 41, 2596-2599.
59. H. Cho, Y. Zhao, Chem. Commun. 2011, 47, 8970-8972.
60. A. Som, S. Matile, Chem. Biodiversity 2005, 2, 717-729.
61. P. A. Brady, R. P. Bonar-Law, S. J. Rowan, C. J. Suckling, J. K. M. Sanders, Chem. Commun. 1996, 319-320.
62. J. B. Birks, I. H. Munro, D. J. Dyson, Proc. R. Soc. London Ser. A 1963, 275, 575-588.
63. R. Scott Lokey, B. L. Iverson, Nature 1995, 375, 303-305
64. G. J. Gabriel, B. L. Iverson, J. Am. Chem. Soc. 2002, 124, 15174-15175
65. G. J. Gabriel, S. Sorey, B. L. Iverson, J. Am. Chem. Soc. 2005, 127, 2637-2640
66. V. J. Bradford, B. L. Iverson, J. Am. Chem. Soc. 2008, 130, 1517-1524.
67. Y. Zhao, Z. Zhong, E. H. Ryu, J. Am. Chem. Soc. 2007, 129, 218-225.
68. Z. Zhong, X. Li, Y. Zhao, J. Am. Chem. Soc. 2011, 133, 8862-8865.
69. H. S. Chan, S. Bromberg, K. A. Dill, Philos. Trans. R. Soc. London Ser. B 1995, 348, 61-70
70. R. B. Prince, J. G. Saven, P. G. Wolynes, J. S. Moore, J. Am. Chem. Soc. 1999, 121, 3114-3121.
71. T. E. Creighton, Protein Structure: A Practical Approach, IRL Press, Oxford, 1997.
72. Y. Zhao, J. S. Moore, in Foldamers: Structure, Properties, and Applications, (Eds.:, S. Hecht, I. Huc,), Wiley-VCH, Weinheim, 2007, pp. 75-108.
73. S. A. Smith, J. H. Morrissey, J. Thromb. Haemostasis 2004, 2, 1155-1162.
74. O. S. Andersen, R. E. Koeppe, Annu. Rev. Biophys. Biomol. Struct. 2007, 36, 107-130.
75. B. A. Lewis, D. M. Engelman, J. Mol. Biol. 1983, 166, 203-210
76. N. Kucerka, Y. F. Liu, N. J. Chu, H. I. Petrache, S. Tristram-Nagle, J. F. Nagle, Biophys. J. 2005, 88, 2626-2637.
77. The hydrophobic diameter of a micelle is roughly twice the hydrophobic chain length of the surfactant. See:, M. J. Rosen, Surfactants and Interfacial Phenomena, Wiley, New York, 1989, p. 112.
78. F. A. Nezil, M. Bloom, Biophys. J. 1992, 61, 1176-1183.
79. R. R. C. New, Liposomes: A Practical Approach, IRL Press, Oxford, 1990, pp. 131-134.
80. S. Otto, M. Osifchin, S. L. Regen, J. Am. Chem. Soc. 1999, 121, 10440-10441
81. M. Merritt, M. Lanier, G. Deng, S. L. Regen, J. Am. Chem. Soc. 1998, 120, 8494-8501.
82. S. Litvinchuk, G. Bollot, J. Mareda, A. Som, D. Ronan, M. R. Shah, P. Perrottet, N. Sakai, S. Matile, J. Am. Chem. Soc. 2004, 126, 10067-10075.
83. J. C. M. Holthuis, G. van Meer, K. Huitema, Mol. Membr. Biol. 2003, 20, 231-241.
84. S. Krasne, G. Eisenman, G. Szabo, Science 1971, 174, 412-415.
85. H. Tanaka, S. Litvinchuk, D.-H. Tran, G. Bollot, J. Mareda, N. Sakai, S. Matile, J. Am. Chem. Soc. 2006, 128, 16000-16001.