Pd(II)-mediated assembly of porphyrin channels in bilayer membranes

Langmuir

Volumn 27, Issue 4, 2011, Pages 1448-1456

  Devi, Usha ^a   Brown, James R D ^a   Almond, Andrew ^a   Webb, Simon J ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BI-LAYER; BILAYER MEMBRANES; BINDING MODELS; CARBOXYFLUORESCEIN; FLUORESCENCE TITRATIONS; GEOMETRIC MATCHING; LINEAR OLIGOMERS; PHOSPHOLIPID BILAYER; PYRIDYL; RELEASE RATE;

OLIGOMERIZATION; OLIGOMERS; PALLADIUM COMPOUNDS; PHOSPHOLIPIDS;

PORPHYRINS;

PALLADIUM; PORPHYRIN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; LIPID BILAYER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

LIPID BILAYERS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PALLADIUM; PORPHYRINS;

EID: 79952927771     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la104152s     Document Type: Article

References (58)

1. Sansom, M. S. P. Curr. Opin. Struct. Biol 1998, 8, 237-244.
2. (a) Ghadiri, M. R.; Granja, J. R.; Buehler, L. K. Nature 1994, 369, 301-304.
3. (b) Granja, J. R.; Ghadiri, M. R. J. Am. Chem. Soc. 1994, 16, 10785-10786.
4. (c) Matile, S. Chem. Soc. Rev. 2001, 30, 158-167.
5. (d) Talukdar, P.; Bollot, G.; Mareda, J.; Sakai, N.; Matile, S. J. Am. Chem. Soc. 2005, 127, 6528-6529.
6. (e) Ma, L.; Melegari M.; Colombini, M.; Davis, J. T. J. Am, Chem. Soc. 2008, 130, 2938-2939.
7. Drain, C. M. Proc. Natl. Acad. Sci. U. S. A. 2002, 99, 5178-5182.
8. Doyle, E. L.; Hunter, C. A.; Phillips, H. C.; Webb, S. J.; Williams, N. H. J. Am. Chem. Soc. 2003, 125, 4593-4599.
9. (a) Fujita, M.; Nagao, S.; Iida, M.; Ogata, M.; Ogura, K. J. Am. Chem. Soc. 1993, 115, 1574-1576.
10. (b) Fujita, M.; Yazaki, J.; Ogura, K. J. Am. Chem. Soc. 1990, 112, 5645-5647.
11. (a) Suzuki, K.; Tominaga, M.; Kawano, M.; Fujita, M. Chem. Commun. 2009, 1638-1640.
12. (b) Tominaga, M.; Suzuki, K.; Kawano, M.; Kusukawa, T.; Ozeki, T.; Sakamoto, S.; Yamaguchi, K.; Fujita, M. Angew. Chem., Int. Ed. 2004, 43, 5621-5625.
13. Fyles, T. M.; Tong, C. C. New J. Chem. 2007, 31, 655-661.
14. Fyles, T. M.; Tong., C. C. New J. Chem. 2007, 31, 296-304.
15. (a) Wilson, C. P.; Webb, S. J. Chem. Commun. 2008, 4007-4009.
16. (b) Wilson, C. P.; Boglio, C.; Ma, L.; Cockroft S. L.; Webb, S. J. Chem.-Eur. J. DOI: 10.1002/chem.201002031.
17. (a) Fuhrhop, J.-H.; Köning, J. Membranes and Molecular Assemblies: The Synkinetic Approach; Monographs in Supramolecular Chemistry; The Royal Society of Chemistry: Cambridge, U. K., 1994; Chapter 4.
18. (b) Gokel, G. W.; Daschbach, M. M. Coord. Chem. Rev. 2008, 252, 886-902.
19. Ferdani, R.; Li, R.; Pajewski, R.; Pajewska, J.; Winter, R. K.; Gokel, G. W. Org. Biomol Chem. 2007, 5, 2423-2432.
20. Alessio, E.; Iengo, E.; Marzilli, L. G. Supramol. Chem. 2002, 14, 103-120.
21. Fan, J.; Whiteford, J. A.; Olenyuk, B.; Levin, M. D.; Stang, P. J.; Fleischer, E. B. J. Am. Chem. Soc. 1999, 121, 2741-2752.
22. (a) Anderson, H. L.; Sanders, J. K. M. J. Chem. Soc, Chem. Commun. 1989, 1714-1715.
23. (b) Webb, S. J.; Sanders, J. K. M. Inorg. Chem. 2000, 39, 5920-5929.
24. (c) Mackay, L. G.; Anderson, H. L.; Sanders, J. K. M. J. Chem. Soc, Chem. Commun. 1992, 43-44.
25. Sun, D.; Tham, F. S.; Reed, C. A.; Chaker, L.; Boyd, P. D. W. J. Am. Chem. Soc. 2002, 124, 6604-6612.
26. Alessio, E.; Geremia, S.; Mestroni, S.; Iengo, E.; Srnova, I.; Slouf, M. Inorg. Chem. 1999, 38, 869-875.
27. Mak, C. C.; Bampos, N.; Darling, S. L.; Montalti, L. P.; Sanders, J. K. M. J. Org. Chem. 2001, 66, 4476-4486.
28. Lee, C. H.; Lindsay, J. S. Tetrahedron 1994, 50, 11427-11440.
29. Littler, B. J.; Ciringh, Y.; Lindsay, J. S. J. Org. Chem. 1999, 64, 2864-2872.
30. Taylor, P. N.; Anderson, H. L. J. Am. Chem. Soc. 1999, 121, 11538-11545.
31. Twyman L. J.; King A. S. H. Chem. Commun. 2002 910-911.
32. Chi X.; Guerin A J.; Haycock R A.; Hunter C A.; Sarson L D.; J. Chem. Soc.; Chem. Commun. 1995, 2567-2569;.
33. Ercolani, G.; Ioele, M.; Monti, D. New J. Chem. 2001, 25, 783-789.
34. Ercolani, G. Struct. Bonding (Berlin) 2006, 121, 167-215.
35. Chi X.; Guerin A J.; Haycock R A.; Hunter C A.; Sarson L D.; J. Chem. Soc.; Chem. Commun. 1995, 2563-2565;.
36. We have denoted this as "ucmc" rather than "cmc" as used in Ercolani G J. Phys. Chem. B 1998, 102, 5699-5703.
37. Fleischer, E. B.; Shachter, A. M. Inorg. Chem. 1991, 30, 3763-3769.
38. Devi, U. Ph. D. Thesis. University of Manchester, 2007.
39. Hunter, C. A.; Sanders, J. K. M.; Stone, A. J. Chem. Phys. 1989, 133, 395-404.
40. Ballester, P.; Oliva, A. I.; Costa, A.; Deya, P. M.; Frontera, A.; Gomila, R. M.; Hunter, C. A. J. Am. Chem. Soc. 2006, 128, 5560-5569.
41. (a) Komatsu, T.; Moritake, M.; Tsuchida, E. Chem-Eur. J. 2003, 9, 4626-4633.
42. (b) Tsuchida, E.; Komatsu, T.; Arai, K.; Yamada, K.; Nishide, H.; Fuhrhop, J.-H. Lammuir 1995, 11, 1877-1884.
43. (c) Schell, C.; Hombrecher, H. K. Chem.-Eur. J. 1999, 5, 587-598.
44. Angelova, M.; Dimitrov, D. Faraday Discuss. 1986, 81, 303-311.
45. Chen, W.-H.; Shao, X.-B.; Regen, S. L. J. Am. Chem. Soc. 2005, 127, 12727-12735.
46. Hydrolysis of the ester groups in 1 to give a more amphiphilic porphyrin that can be incorporated into EYPC bilayers up to 4% mol/mol gave a poorer transport system because the hydrolyzed porphyrin transported the dye in the absence of 2.
47. (a) Chen, W.-H.; Janout, V.; Kondo, M.; Mosoian, A.; Mosoyan, G.; Petrov, R. R.; Klotman, M. E.; Regen, S. L. Bioconiugate Chem. 2009, 20, 1711-1715.
48. (b) Fyles, T. M.; Hu, C.-W.; Luong, H. J. Org. Chem. 2006, 71, 8545-8551.
49. (c) Gorteau, V.; Bollot, G.; Mareda, J.; Matile, S. Org. Biomol. Chem. 2007, 5, 3000-3012.
50. (a) Berger, N.; Sachse, A.; Bender, J.; Schubert, R.; Brandl, M. Int. J. Pharm. 2001, 223, 55-68.
51. (b) Mayer, L. D.; Hope, M. J.; Cullis, P. R. Biochim. Biophys. Acta 1986, 858, 161-168.
52. At concentrations of 2 above 100 μM, the metal complex began to initiate 5/6-CF transport in the absence of porphyrin 1.
53. 2 dimers are not the active species.
54. (a) Fyles, T. M. Chem. Soc. Rev. 2007, 36, 335-347.
55. (b) Gokel, G. W.; Schlesinger, P. H.; Djedovic, N. K.; Ferdani, R.; Harder, E..; Hu, J. X.; Leevy, W. M.; Pajewska, J.; Pajewski, R.; Weber, M. E. Bioorg. Med. Chem. 2004, 12, 1291-1304.
56. Todo, H.; Kimura, E.; Yasuno, H.; Tokudome, Y.; Hashimoto, F.; Ikarashi, Y.; Sugibayashi, K. Biol. Pharm. Bull. 2010, 33, 1394-1399.
57. The lack of release can suggest a carrier mechanism but can also be due to other effects, including the "squeezing out" of channel formers and inhibited selfassembly.
58. See Otto, S.; Osifchin, M.; Regen, S. L. J. Am. Chem. Soc. 1999, 121, 10440-10441.