From cholapod to cholaphane transmembrane anion carriers: Accelerated transport through binding site enclosure

Chemical Communications

Volumn 46, Issue 13, 2010, Pages 2227-2229

  Judd, Luke W ^a   Davis, Anthony P ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CHOLAPHANE; MACROCYCLIC COMPOUND; UNCLASSIFIED DRUG;

ANION TRANSPORT; ARTICLE; CELL MEMBRANE TRANSPORT; CHEMICAL STRUCTURE; CYCLIZATION; HYDROGEN BOND; HYDROGENATION; STEREOSPECIFICITY;

EID: 77949599238     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b927005a     Document Type: Article

References (31)

1. Chloride Movements Across Cellular Membranes, Advances in Molecular and Cell Biology, ed., M. Pusch, Elsevier, San Diego, 2007, vol. 38
2. T. J. Jentsch V. Stein F. Weinreich A. A. Zdebik Phys. Rev. 2002 82 503
3. T. J. Jentsch C. A. Hubner J. C. Fuhrmann Nat. Cell Biol. 2004 6 1039
4. F. M. Ashcroft, Ion Channels and Disease, Academic Press, London, 2000
5. A. P. Davis D. N. Sheppard B. D. Smith Chem. Soc. Rev. 2007 36 348
6. X. Li Y. D. Wu D. Yang Acc. Chem. Res. 2008 41 1428
7. J. Mareda S. Matile Chem.-Eur. J. 2009 15 28
8. G. W. Gokel N. Barkey New J. Chem. 2009 33 947
9. P. V. Santacroce J. T. Davis M. E. Light P. A. Gale J. C. Iglesias-Sanchez P. Prados R. Quesada J. Am. Chem. Soc. 2007 129 1886
10. B. A. McNally E. J. O'Neil A. Nguyen B. D. Smith J. Am. Chem. Soc. 2008 130 17274
11. P. V. Jog M. S. Gin Org. Lett. 2008 10 3693
12. I. Izzo S. Licen N. Maulucci G. Autore S. Marzocco P. Tecilla F. De Riccardis Chem. Commun. 2008 2986
13. J. T. Davis P. A. Gale O. A. Okunola P. Prados J. C. Iglesias-Sanchez T. Torroba R. Quesada Nat. Chem. 2009 1 138
14. 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., Int. Ed. 2003 42 4931
15. B. A. McNally A. V. Koulov B. D. Smith J. B. Joos A. P. Davis Chem. Commun. 2005 1087
16. B. A. McNally A. V. Koulov T. N. Lambert B. D. Smith J. B. Joos A. L. Sisson J. P. Clare V. Sgarlata L. W. Judd G. Magro A. P. Davis Chem.-Eur. J. 2008 14 9599
17. A. P. Davis J.-B. Joos Coord. Chem. Rev. 2003 240 143
18. A. P. Davis Coord. Chem. Rev. 2006 250 2939
19. The term "cholaphane" is used for macrocycles formed from bile acid and aromatic units. See: A. P. Davis, R. P. Bonar-Law and J. K. M. Sanders, in Comprehensive Supramolecular Chemistry, ed., Y. Murakami, Pergamon, Oxford, 1996, vol. 4 (Supramolecular Reactivity and Transport: Bioorganic Systems), p. 257
20. E. Virtanen E. Kolehmainen Eur. J. Org. Chem. 2004 3385
21. A. P. Davis Molecules 2007 12 2106
22. A. L. Sisson J. P. Clare A. P. Davis Chem. Commun. 2005 5263
23. V. del Amo L. Siracusa T. Markidis B. Baragaña K. M. Bhattarai M. Galobardes G. Naredo M. N. Pérez-Payán A. P. Davis Org. Biomol. Chem. 2004 2 3320
24. D. J. Cram J. M. Cram Science 1974 183 803
25. A. J. Ayling S. Broderick J. P. Clare A. P. Davis M. N. Pérez-Payán M. Lahtinen M. J. Nissinen K. Rissanen Chem.-Eur. J. 2002 8 2197
26. J. P. Clare A. J. Ayling J. B. Joos A. L. Sisson G. Magro M. N. Pérez-Payán T. N. Lambert R. Shukla B. D. Smith A. P. Davis J. Am. Chem. Soc. 2005 127 10739
27. A. J. Pope R. A. Leigh Planta 1988 176 451
28. F. Wissing J. A. C. Smith J. Membr. Biol. 2000 177 199
29. As described in ref. 4a, the antiport mechanism has been conclusively demonstrated for cholapod 1 It has been shown that cholapods can carry phospholipid head-groups through membrane interiors. This implies that the cholapod-head-group interaction is significant, and could well interfere with chloride transport. See: T. N. Lambert J. M. Boon B. D. Smith M. N. Pérez-Payán A. P. Davis J. Am. Chem. Soc. 2002 124 5276
30. B. T. Kilbourn J. D. Dunitz L. A. R. Pioda W. Simon J. Mol. Biol. 1967 30 559
31. K. Neupert-Laves M. Dobler Helv. Chim. Acta 1975 58 432