Tuning nanopore formation of oligocholate macrocycles by carboxylic acid dimerization in lipid membranes

Journal of Organic Chemistry

Volumn 78, Issue 9, 2013, Pages 4610-4614

  Widanapathirana, Lakmini ^a   Zhao, Yan ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACIDS; DIMERIZATION; LIPID BILAYERS; LIPIDS;

ASSOCIATIVE INTERACTIONS; DICARBOXYLIC ACID; HYDROPHOBIC INTERACTIONS; LIPID MEMBRANES; NANOPORE FORMATION; STRUCTURE AND ACTIVITIES; TEREPHTHALIC ACIDS; TRANSPORT ACTIVITY;

NANOPORES;

CARBOXYLIC ACID; CHOLIC ACID DERIVATIVE; GLUCOSE; MACROCYCLIC COMPOUND; WATER; BIOMIMETIC MATERIAL; LIPID BILAYER;

ARTICLE; DIMERIZATION; GLUCOSE TRANSPORT; HYDROGEN BOND; HYDROPHOBICITY; LIPID BILAYER; LIPID MEMBRANE; MOLECULAR INTERACTION; NANOPORE; SUBSTITUTION REACTION; CHEMICAL PHENOMENA; CHEMISTRY; CONFORMATION; TRANSPORT AT THE CELLULAR LEVEL; ULTRASTRUCTURE;

BIOLOGICAL TRANSPORT; BIOMIMETIC MATERIALS; CARBOXYLIC ACIDS; CHOLATES; DIMERIZATION; GLUCOSE; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; LIPID BILAYERS; MACROCYCLIC COMPOUNDS; MOLECULAR CONFORMATION; NANOPORES;

EID: 84877153371     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo400455x     Document Type: Article

References (45)

1. Yeagle, P. The Structure of Biological Membranes, 2 nd ed.; CRC Press: Boca Raton, 2005.
2. Hopkins, A. L.; Groom, C. R. Nat. Rev. Drug Discovery 2002, 1, 727
3. Lundstrom, K. Curr. Protein Pept. Sci. 2006, 7, 465
4. Zhao, Y.; Zhong, Z.; Ryu, E.-H. J. Am. Chem. Soc. 2007, 129, 218
5. Cho, H.; Zhong, Z.; Zhao, Y. Tetrahedron 2009, 65, 7311
6. Zhang, S.; Zhao, Y. Chem.-Eur. J. 2011, 17, 12444
7. Cho, H.; Zhao, Y. J. Am. Chem. Soc. 2010, 132, 9890
8. Cho, H.; Widanapathirana, L.; Zhao, Y. J. Am. Chem. Soc. 2011, 133, 141
9. Widanapathirana, L.; Zhao, Y. Langmuir 2012, 28, 8165
10. Wang, T.; Widanapathirana, L.; Zhao, Y.; Hong, M. Langmuir 2012, 28, 17071
11. Granja, J. R.; Ghadiri, M. R. J. Am. Chem. Soc. 1994, 116, 10785
12. Sakai, N.; Mareda, J.; Matile, S. Acc. Chem. Res. 2005, 38, 79
13. Das, G.; Talukdar, P.; Matile, S. Science 2002, 298, 1600
14. Sakai, N.; Sorde, N.; Matile, S. J. Am. Chem. Soc. 2003, 125, 7776
15. Ma, L.; Melegari, M.; Colombini, M.; Davis, J. T. J. Am. Chem. Soc. 2008, 130, 2938
16. Chen, L.; Si, W.; Zhang, L.; Tang, G.; Li, Z.-T.; Hou, J.-L. J. Am. Chem. Soc. 2013, 135, 2152
17. Bailey, M.; Brown, C. J. Acta Crystallogr. 1967, 22, 387
18. Sledz, M.; Janczak, J.; Kubiak, R. J. Mol. Struct. 2001, 595, 77
19. Widanapathirana, L.; Li, X.; Zhao, Y. Org. Biomol. Chem. 2012, 10, 5077
20. Kinsky, S. C.; Haxby, J. A.; Zopf, D. A.; Alving, C. R.; Kinsky, C. B. Biochemistry 1969, 8, 4149
21. Stein, W. D. Carriers and Pumps: An Introduction to Membrane Transport; Academic Press: San Diego, 1990.
22. Nezil, F. A.; Bloom, M. Biophys. J. 1992, 61, 1176
23. Holthuis, J. C. M.; van Meer, G.; Huitema, K. Mol. Membr. Biol. 2003, 20, 231
24. Demel, R. A.; Bruckdor, K. R.; van Deene, L. L. Biochim. Biophys. Acta 1972, 255, 321
25. Papahadjopoulos, D.; Nir, S.; Ohki, S. Biochim. Biophys. Acta 1972, 266, 561
26. New, R. R. C. Liposomes: A Practical Approach; IRL Press: Oxford, 1990.
27. Cho, H.; Zhao, Y. Langmuir 2011, 27, 4936
28. Davis, J. T.; Okunola, O.; Quesada, R. Chem. Soc. Rev. 2010, 39, 3843
29. Struck, D. K.; Hoekstra, D.; Pagano, R. E. Biochemistry 1981, 20, 4093
30. Another reason was the flexibility in the macrocycle introduced by the inserted l -cysteine. Our earlier work indicates that rigidity in the macrocycle facilitates the pore formation: Widanapathirana, L.; Zhao, Y. J. Org. Chem. 2012, 77, 4679
31. Yang, J.; Marendaz, J. L.; Geib, S. J.; Hamilton, A. D. Tetrahedron Lett. 1994, 35, 3665
32. Zimmerman, S. C.; Zeng, F. W.; Reichert, D. E. C.; Kolotuchin, S. V. Science 1996, 271, 1095
33. James A, H. In Carbon-13 NMR Spectroscopy of Biological Systems; Academic Press: San Diego, 1995; p 117.
34. Kamp, F.; Hamilton, J. A. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 11367
35. Kamp, F.; Zakim, D.; Zhang, F.; Noy, N.; Hamilton, J. A. Biochemistry 1995, 34, 11928
36. Hamilton, J. A.; Guo, W.; Kamp, F. Mol. Cell. Biochem. 2002, 239, 17
37. Cubberley, M. S.; Iverson, B. L. J. Am. Chem. Soc. 2001, 123, 7560
38. Widanapathirana, L.; Zhao, Y. J. Org. Chem. 2012, 77, 4679
39. Wenograd, J.; Spurr, R. A. J. Am. Chem. Soc. 1957, 79, 5844
40. Goodman, D. S. J. Am. Chem. Soc. 1958, 80, 3887
41. Boccalon, M.; Iengo, E.; Tecilla, P. J. Am. Chem. Soc. 2012, 134, 20310
42. Zhao, Y.; Zhong, Z. J. Am. Chem. Soc. 2005, 127, 17894
43. Struthers, H.; Spingler, B.; Mindt, T. L.; Schibli, R. Chem.-Eur. J. 2008, 14, 6173
44. Morris, W.; Taylor, R. E.; Dybowski, C.; Yaghi, O. M.; Garcia-Garibay, M. A. J. Mol. Struct. 2011, 1004, 94
45. Pokhodylo, N. T.; Matiychuk, V. S. J. Heterocycl. Chem. 2010, 47, 415