Membrane transporters for anions that use a relay mechanism

Journal of the American Chemical Society

Volumn 130, Issue 51, 2008, Pages 17274-17275

  McNally, Beth A ^a   O'Neil, Edward J ^a   Nguyen, Anh ^a   Smith, Bradley D ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACCEPTOR MOLECULES; ACYL CHAIN; AMPHIPHILIC COMPOUND; BI-LAYER; BIOMEDICAL RESEARCH; CHLORIDE IONS; COUNTERTRANSPORT; DIANION; MEMBRANE SURFACE; PHOSPHATIDYLCHOLINE; SYNTHETIC MEMBRANES; THERAPEUTIC AGENTS; TRANSPORT RATE; UREA GROUPS;

CHLORINE COMPOUNDS; DERIVATIVES; ELECTRIC RELAYS; HYDROGEN; HYDROGEN BONDS; METABOLISM; NEGATIVE IONS; UREA;

MEMBRANES;

ANION; CARRIER PROTEIN; CHLORIDE; MEMBRANE PROTEIN; UREA;

ANION EXCHANGE; ANION TRANSPORT; ARTICLE; BINDING AFFINITY; CHLORIDE TRANSPORT; MEMBRANE TRANSPORT; ACTIVE TRANSPORT; BIOLOGICAL MODEL; CHEMISTRY; DIMERIZATION; DRUG DESIGN; HYDROGEN BOND; KINETICS; LIPID BILAYER; METABOLISM; METHODOLOGY; SURFACE PROPERTY; TRANSPORT AT THE CELLULAR LEVEL;

ANIONS; BIOLOGICAL TRANSPORT; BIOLOGICAL TRANSPORT, ACTIVE; CHEMISTRY, PHARMACEUTICAL; DIMERIZATION; DRUG DESIGN; HYDROGEN BONDING; KINETICS; LIPID BILAYERS; MEMBRANE PROTEINS; MEMBRANE TRANSPORT PROTEINS; MODELS, BIOLOGICAL; SURFACE PROPERTIES; UREA;

EID: 67849128241     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja8082363     Document Type: Article

References (28)

1. (a) Stein, W. D. Channels, Carriers and Pumps, An Introduction to Membrane Transport; Academic: San Diego, CA, 1990.
2. (b) Smith, B. D. ; Lambert, T. N. Chem. Commun. 2003, 2261-2268.
3. Recent reviews of synthetic transporters: (a) Gokel, G. W. ; Carasel, I. A. Chem. Soc. Rev. 2007, 36, 378-389.
4. (b) Sakai, N. ; Mareda, J. ; Matile, S. Mol. Biosyst. 2007, 10, 658-666.
5. (c) Fyles, T. M. Chem. Soc. Rev. 2007, 36, 335-347.
6. (d) McNally, B. A. ; Leevy, W. M. ; Smith, B. D. Supramol. Chem. 2007, 19, 29-37.
7. (e) Koert, U. ; Al-Momani, L. ; Pfeifer, J. R. Synthesis 2004, 8, 112911-112946.
8. Davis, A. P. ; Sheppard, D. N. ; Smith, B. D. Chem. Soc. Rev. 2007, 34, 8-357, and references therein.
9. Ashcroft, F. M. Ion Channels and Disease; Academic Press: London, 2000.
10. Notable exceptions are (a) the water soluble peptide transporters designed by Tomich and coworkers. For a leading reference, see: Shank, L. P. ; Broughman, J. R. ; Takeguchi, W. ; Cook, G. ; Robbins, A. S. ; Hahn, L. ; Radke, G. ; Iwamoto, T. ; Schultz, B. D. ; Tomich, J. M. Biophys. J. 2006, 90, 2138-2150.
11. (b) The amphiphilic peptide transporters designed by Gokel and coworkers. For a leading reference, see: Elliott, E. K. ; Stine, K. J. ; Gokel, G. W. J. Membr. Sci. 2008, 321, 43-50.
12. For studies of relay transport processes in much thicker synthetic plasticized membranes, see: (a) Riggs, J. A. ; Smith, B. D. J. Am. Chem. Soc. 1997, 119, 2765-2766.
13. (b) White, K. M. ; Duggan, P. J. ; Sheahan, S. L. ; Tyndall, E. M. ; Smith, B. D. J. Membr. Sci. 2001, 194, 165-175.
14. For membrane active phospholipids with simple acyl chain modifications, see:(a) Menger, F. M. ; Aikens, P. Angew. Chem., Int. Ed. 1992, 31, 898-900.
15. (b) Menger, F. M. ; Galloway, A. L. ; Chlebowski, M. E. ; Wu, S. J. Am. Chem. Soc. 2006, 128, 14034-14035.
16. It is well established that a modestly polar group appended to the end of a phospholipid's acyl chain undergoes substantially dynamic movement between the lipophilic membrane interior and the polar membrane surface. (a) Huster, D. ; Mü ller, P. ; Arnold, K. ; Herrmann, A. Biophys. J. 2001, 80, 822-831.
17. (b) Loura, L. M. S. ; Ramalho, J. P. P. Biochim. Biophys. Acta 2007, 1768, 467-478.
18. (c) Menger, F. M. ; Keiper, J. S. ; Caran, K. L. J. Am. Chem. Soc. 2002, 124, 11842-11843.
19. McNally, B. A. ; Koulov, A. V. ; Lambert, T. N. ; Smith, B. D. ; Joos, J. -B. ; Sisson, A. L. ; Clare, J. P. ; Sgarlata, V. ; Judd, L. W. ; Magro, G. ; Davis, A. P. Chem-Eur. J. 2008, 14, 9599-9606.
20. (a) Roseto, R. ; Hajdu, J. Tetrahedron Lett. 2005, 46, 2941-2944.
21. (b) Lampkins, A. J. ; O'Neil, E. J. ; Smith, B. D. J. Org. Chem. 2008, 73, 6053-6058.
22. -1 for N-(4-tert- butylphenyl)-N′ -octyl urea as determined by the method in ref 9.
23. McNally, B. A. ; Koulov, A. V. ; Smith, B. D. ; Joos, J. B. ; Davis, A. P. Chem. Commun. 2005, 1087-1089.
24. 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. Angew, Chem., Int. Ed. 2003, 42, 4931-4933.
25. Otto, S. ; Osifchin, M. ; Regen, S. L. J. Am. Chem. Soc. 1999, 121, 7276-7277.
26. DiGiogio, A. F. ; Otto, S. ; Bandyopadhyaya, P. ; Regen, S. L. J. Am. Chem. Soc. 2000, 122, 11029-11030.
27. Lewis, B. A. ; Engelman, D. M. J. Mol. Biol. 1983, 166, 211-217.
28. Membrane thickness studies with a classic mobile carrier like valinomycin report a moderate ten-fold decrease in transport rate as the acyl chain carbon number is increased from 16 to 22 (Benz, R. ; Frohlich, O. ; Lä uger, P. Biochim. Biophys. Acta 1977, 464, 465-481. With channel transport processes there is a bell-shaped relationship with membrane thickness; optimal transport is observed when the membrane thickness matches the length of the channel structure: Weber, M. E. ; Schlesinger, P. H. ; Gokel, G. W. J. Am. Chem. Soc. 2005, 127, 636-642.