Ethanol-induced reorganization of the liquid-ordered phase: Enhancement of cholesterol - Phospholipid association

Journal of the American Chemical Society

Volumn 128, Issue 1, 2006, Pages 265-269

  Zhang, Jianbing ^a   Cao, Honghua ^a   Jing, Bingwen ^a   Regen, Steven L ^a  

^a LEHIGH UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHOLESTEROL; DIMERS; MEMBRANES; MIXTURES; MOLECULAR DYNAMICS; PHOSPHOLIPIDS;

1,2-DIPALMITOYI-SN-GLYCERO-3-PHOSPHOCHOLINE (DPPC); LIQUID-ORDERED PHASE; NEAREST-NEIGHBOR RECOGNITION (NNR) EXPERIMENTS; PHOSPHOLIPID ASSOCIATION;

ETHANOL;

1,2 DISTEAROYLLYCERO 3 PHOSPHOCHOLINE; ALCOHOL; CHOLESTEROL; DIPALMITOYLPHOSPHATIDYLCHOLINE; PHOSPHOLIPID; UNCLASSIFIED DRUG;

ARTICLE; DIMERIZATION; LIPID TRANSPORT; LIQUID ORDERED PHASE; MATHEMATICAL ANALYSIS; MOLECULAR RECOGNITION; NEAREST NEIGHBOR RECOGNITION; PHASE TRANSITION; THERMODYNAMICS;

1,2-DIPALMITOYLPHOSPHATIDYLCHOLINE; CHOLESTEROL; ETHANOL; KINETICS; LIPID BILAYERS; PHOSPHATIDYLCHOLINES;

EID: 30744474716     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja056918d     Document Type: Article

References (40)

1. Chin, J. H.; Goldsterin, D. B. Mol. Pharmacol. 1981, 19, 425-431.
2. Chin, J. H.; Goldstein, D. B. Mol. Pharmacol. 1977, 13, 435-441.
3. Barry, J. A.; Gawrisch, K. Biochemistry 1995, 34, 8852-8860.
4. Wood, W. G.; Schroeder, F. Life Sci. 1988, 43, 467-475.
5. Trandum, C.; Westh, P.; Jorgensen, K.; Mouritsen, O. G. Biophys. J. 2000, 78, 2486-2492.
6. Trandum, C.; Westh, P.; Jorgensen, K.; Mouritsen, O. G. J. Phys. Chem. B 1999, 103, 4751-4756.
7. Komatsu, H.; Guy, P. T.; Rowe, E. S. Chem. Phys. Lipids 1993, 65, 11-21.
8. Goldstein, D. B. Annu. Rev. Pharmacol. Toxicol. 1984, 24, 43-64.
9. Goldstein, D. B. Annals of Emergency Medicine 1986, 15, 43/1013-48/1048.
10. Sun, G. Y.; Sun, A. Y. Alcohol.: Clin. Exp. Res. 1985, 9, 164-179.
11. Rowe, E. S.; Cutrera, T. A. Biochemistry 1990, 29, 10398-10404.
12. Nambi, P.; Rowe, E. S.; McIntosh, T. J. Biochemistry 1988, 27, 9175-9182.
13. Komatsu, H.; Rowe, E. S. Biochemistry 1991, 30, 2463-2470.
14. Mou, J.; Yang, J.; Huang, C.; Shno, Z. Biochemistry 1994, 33, 9981-9985.
15. McClain, R. L.; Breen, J. J. Langmuir 2001, 17, 5121-5124.
16. Barry, J. A.; Gawrisch, K. Biochemistry 1994, 33, 8082-8088.
17. Wachtel, E.; Borochov, N.; Bach, D.; Miller, I. R. Chem. Phys. Lipids 1998, 92, 127-137.
18. Bach, D.; Borochov, N.; Wachtel, E. Chem. Phys. Lipids 2002, 114, 123-130.
19. Hote, L. L.; Gawrisch, K. Biochemistry 1997, 36, 4669-4674.
20. Feller, S. E.; Brown, C. A.; Nizza, D. T.; Gawrisch, K. Biophys. J. 2002, 82, 1396-1404.
21. Edidin, M. Annu. Rev. Biomol. Struct. 2003, 32, 257-283.
22. Simons, K.; Vaz, W. L. C. Annu. Rev. Biomol. Struct. 2004, 33, 269-295.
23. Simons, K.; Toomre, D. Nat. Rev. Mol. Cell Biol. 2000, 1, 31-39.
24. McConnell, H. M.; Radhakrishnan, A. Biochim. Biophys. Acta 2003, 1610, 159-173.
25. Sugahara, M.; Uragami, M.; Regen, S. L. J. Am. Chem. Soc. 2003, 125, 13040-13041.
26. Cao, H.; Zhang, J.; Jing, B.; Regen, S. L. J. Am. Chem. Soc. 2005, 127, 8813-8816.
27. For a review of the NNR method, see: (a) Davidson, S. K. M.; Regen, S. L. Chem. Rev. 1997, 97, 1269-1280.
28. (b) Cao, H.; Tokutake, N.; Regen, S. L. J. Am. Chem. Soc. 2003, 125, 16182-16183.
29. (c) Sugahara, M.; Uragami, M.; Regen, S. L. J. Am. Chem. Soc. 2002, 124, 4253-4256.
30. Sankaram, M. B.; Thompson, T. E. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 8686-8690.
31. Almeida, P. F.; Vaz, W. C. C.; Thompson, T. E. Biophys. J. 1993, 64, 399-412.
32. Sugahara, M.; Uragami, M.; Yan, X.; Regen, S. L. J. Am. Chem. Soc. 2001, 123, 7939-7940.
33. Krisovitch, S. M.; Regen, S. L. J. Am. Chem. Soc. 1992, 114, 9828-9835.
34. 1H NMR indicated less than 13 ethanol molecules were taken up per phospholipid. On the basis of partition coefficients that have been previously estimated for analogous membranes made from 1,2-dimyristoyl-sn-glycero-3-phosphocholine (DMPC) and cholesterol by isothermal litration calorimetry, one can estimate that ca, 10-50 ethanol molecules are being taken up per 100 phospholipids (ref 5).
35. NNR measurements that were carried out using 30 mol % sterol, in the absence and in the presence of 2.9% ethanol, showed no variation in K when the NaCl concentration in the buffer was varied from 100 to 300 mM. These results indicate that electrostatic effects do not contribute significantly to the observed mixing of 1 with 2.
36. Vidal, A.; McIntosh, T. J. Biophys. J. 2005, 89, 1102-1108.
37. Romanenko, V. G.; Fang, Y.; Byfield, F.; Travis, A. J.; Vandenberg, C. A.; Rothblat, G. H.; Levitan, I. Biophys. J. 2004, 87, 3850-3861.
38. Results from previous NNR studies have led to the suggestion that cholesterol can associate with nc-gA to form complexes (refs 37 and 38). The lower value of K for 1 and 2 in the presence of nc-gA is consistent with this hypothesis, since it would reduce the amount of sterol that is available for associating with the phospholipid.
39. Sugahara, M.; Regen, S. L. Langmuir 2001, 17, 4413-4415.
40. Kishihara, K.; Jing, B.; Regen, S. L. Langmuir 2002, 18, 9635-9637.