Large molecular assembly of amphotericin B formed in ergosterol-containing membrane evidenced by solid-state NMR of intramolecular bridged derivative

Journal of the American Chemical Society

Volumn 128, Issue 36, 2006, Pages 11977-11984

  Matsumori, Nobuaki ^a   Sawada, Yuri ^a   Murata, Michio ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BIOASSAY; BIOLOGICAL MEMBRANES; CONFORMATIONS; DERIVATIVES; HYDROPHILICITY; NUCLEAR MAGNETIC RESONANCE;

CELL WALL; CHEMICAL SHIFT ANISOTROPIES; DIPOLAR COUPLINGS; ERGOSTEROL; GLYCINE; MOLECULAR ASSEMBLY;

ANTIBIOTICS;

AMINOSUGAR; AMPHOTERICIN B; AMPHOTERICIN B DERIVATIVE; BRIDGED COMPOUND; DIMYRISTOYLPHOSPHATIDYLCHOLINE; ERGOSTEROL; GLYCINE; ION CHANNEL; MANNOSE; MYCOSAMINE; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; ARTICLE; ASPERGILLUS NIGER; CELL WALL; CONTROLLED STUDY; DRUG ACCUMULATION; DRUG CONFORMATION; DRUG DESIGN; DRUG PENETRATION; DRUG SELECTIVITY; FUNGAL CELL; HUMAN; HUMAN CELL; HYDROPHILICITY; LIPID BILAYER; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; SOLID STATE; STRUCTURE ACTIVITY RELATION;

AMPHOTERICIN B; DIMYRISTOYLPHOSPHATIDYLCHOLINE; ERGOSTEROL; ION CHANNELS; LIPID BILAYERS; LIPOSOMES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; POTASSIUM;

EID: 33748501498     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja063433w     Document Type: Article

References (47)

1. Gallis, H. A.; Drew, R. H.; Pickard, W. W. Rev. Infect. Dis. 1990, 12, 308-329.
2. Hartsel, S. C.; Bolard, J. Trends Pharmacol. Sci. 1996, 12, 445-449.
3. Ablordeppey, S. Y.; Fan, P. C.; Ablordeppey, J. H.; Mardenborough, L. Curr. Med. Chem. 1999, 6, 1151-1195.
4. Vanden-Bossche, H.; Dromer, F.; Improvisi, I.; LozanoChiu, M.; Rex, J. H.; Sanglard, D. Med. Mycol. 1998, 36, 119-128.
5. Andreoli, T. E. Ann. N.Y. Acad. Sci. 1974, 235, 448-468.
6. De-Kruijff, B.; Demel, R. A. Biochim. Biophys. Acta 1974, 339, 57-70.
7. Cohen, B. E. Biochim. Biophys. Acta 1986, 857, 117-122.
8. Vertut-Croquin, A.; Bolard, J.; Chabbert, M.; Gary-Bobo, C. Biochemistry 1983, 22, 2939-2944.
9. Van-Hoogevest, P.; De-Kruijff, B. Biochim. Biophys. Acta 1978, 511, 397-407.
10. Milhaud, J.; Hartman, M. A.; Bolard, J. Biochimie 1989, 71, 49-56.
11. Vertut-Qroquin, A.; Bolard, J.; Gary-Bobo, C. M. Biochem. Biophys. Res. Commun. 1984, 125, 360-366.
12. Baginski, M.; Gariboldi, P.; Bruni, P.; Borowski, E. Biophys. Chem. 1997, 65, 91-100.
13. Baginski, M.; Resat, H.; Borowski, E. Biochim. Biophys. Acta 2002, 1567, 63-78.
14. Matsumori, N.; Sawada, Y.; Murata, M. J. Am. Chem. Soc. 2005, 127, 10667-10675.
15. Herve, M.; Cybulska, B.; Gary-Bobo, C. M. Eur. Biophys. J. 1985, 12, 121-128.
16. Herve, M.; Debouzy, J. C.; Borowski, E.; Cybulska, B.; Gary-Bobo, C. M. Biochim. Biophys. Acta 1989, 980, 261-272.
17. Matsumori, N.; Yamaji, N.; Matsuoka, S.; Oishi, T.; Murata, M. J. Am. Chem. Soc. 2002, 124, 4180-4181.
18. Yamaji, N.; Matsumori, N.; Matsuoka, S.; Oishi, T.; Murata, M. Org. Lett. 2002, 4, 2087-2089.
19. Matsuoka, S.; Murata, M. Biochim. Biophys. Acta 2002, 1564, 429-434.
20. Matsuoka, S.; Murata, M. Biochim. Biophys. Acta 2003, 1617, 109-115.
21. Matsuoka, S.; Matsumori, N.; Murata, M. Org. Biomol. Chem. 2003, 1, 3882-3884.
22. Matsumori, N.; Eiraku, N.; Matsuoka, S.; Oishi, T.; Murata, M.; Aoki, T.; Ide, T. Chem. Biol. 2004, 11, 673-679.
23. Cotero, B. V.; Rebolledo-AntUnez, S.; Ortega-Blake, I. Biochim. Biophys. Acta 1998, 1375, 43-51.
24. Dufourc, E. J.; Smith, I. C. P.; Jarrell, H. C. Biochim. Biophys. Acta 1984, 776, 317-329.
25. Ruckwardt, T.; Scott, A.; Scott, J.; Mikulecky, P.; Hartsel, S. C. Biochim. Biophys. Acta 1998, 1372, 283-288.
26. Cuntinho, A.; Prieto, M. Biophys. J. 1995, 69, 2541-2557.
27. Legrand, P.; Romero, E. A.; Cohen, B. E.; Bolard, J. Antimicrob. Agents Chemother. 1992, 36, 2518-2522.
28. Ganis, P.; Avitabile, G.; Mechlinski, W.; Schaffner, C. P. J. Am. Chem. Soc. 1971, 93, 4560-4564.
29. Mohamadi, F.; Richards, N. G.; Guida, W. C.; Liskamp, R.; Lipton, M.; Canfield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440-467.
30. Gullion, T.; Schaefer, J. J. Magn. Reson. 1989, 81, 196-200.
31. Saito, H.; Tuzi, S.; Naito, A. Annu. Rep. NMR Spectrosc. 1998, 36, 79-121.
32. Naito, A.; Saito, H. Encycl. Nucl. Magn. Reson. 2002, 9, 283-291.
33. Buffy, J. J.; Waring, A. J.; Lehrer, R. I.; Hong M. Biochemistry 2003, 42, 13725-13734.
34. Matsuoka, S.; Ikeuchi, H.; Matsumori, N.; Murata, M. Biochemistry 2005, 44, 704-710.
35. Dufourc, E. J.; Smith, I. C. P.; Jarrell, H. C. Biochim. Biophys. Acta 1984, 778, 435-442.
36. Saffman, P. G.; Delbruck, M. Proc. Natl. Acad. Sci. U.S.A. 1975, 72, 3111-3113.
37. Tamm, L. K. Biochim. Biophys. Acta 1991, 1071, 123-148.
38. Scherrer, R.; Gerhardt, P. J. Bacteriol. 1971, 107, 718-735.
39. Katsu, T. Biol. Pharm. Bull. 1999, 22, 978-980.
40. Houdai, T.; Matsuoka, S.; Matsumori, N.; Murata, M. Biochim. Biophys. Acta 2004, 1667, 91-100.
41. Gruszecki, W. I.; Gagos, M.; Kemen, P. FEBS Lett. 2002, 524, 92-96.
42. Milhaud, J.; Ponsinet, V.; Takahashi, M.; Mchels, B. Biochim. Biophys. Acta 2002, 1558, 95-108.
43. Hing, A. W.; Schaefer, J.; Kobayashi, G. S. Biochim. Biophys. Acta 2000, 1463, 323-332.
44. Perkins, W. R.; Minchey, S. R.; Boni, L. T.; Swenson, C. E.; Popescu, M. C.; Pasternack, R. F.; Janoff, A. S. Biochim. Biophys. Acta 1992, 1107, 271-282.
45. Kolossvary, I.; Guida, W. C. J. Comput. Chem. 1999, 20, 1671-1684.
46. Halgren, T. A. J. Comput. Chem. 1999, 20, 730-748.
47. Gullion, T.; Baker, D. B.; Conradi, M. S. J. Magn. Reson. 1990, 89, 479-484.