A quantitative assessment of the influence of permanent kinks on the mixing behavior of phospholipids in cholesterol-rich bilayers

Journal of the American Chemical Society

Volumn 126, Issue 47, 2004, Pages 15344-15345

  Jing, Bingwen ^a   Tokutake, Nobuya ^a   McCullough III, Donald H ^a   Regen, Steven L ^a  

^a LEHIGH UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHOLESTEROL; PHOSPHOLIPID;

ARTICLE; ISOMERIZATION; LIPID COMPOSITION; MEMBRANE; MOLECULAR RECOGNITION; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTITATIVE ANALYSIS; SIGNAL TRANSDUCTION; STEREOCHEMISTRY;

EID: 9644290722     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja044517c     Document Type: Article

References (25)

1. (a) Hu, F. B.; Stampfer, M. J.; Manson, J. E.; Rimm, E.; Colditz, G. A.; Rosner, B. A.; Hennekens, C. H.; Willett, W. C. N. Engl. J. Med. 1997, 337, 1491.
2. (b) Allison, D.; Denke, M.; Dietschy, J.; Emken, E.; Kris-Etherton, P.; Nicolosi, R. Am. J. Clin. Nutr. 1995, 62, 655S.
3. Roach, C.; Feller, S. E.; Ward, J. A.; Shaikh, S. R.; Zerouga, M.; Stillwell, W. Biochemistry 2004, 43, 6344.
4. (a) Davidson, S. K. M.; Regen, S. L. Chem. Rev. 1997, 97, 1269.
5. (b) Sugahara, M.; Uragami, M.; Regen, S. L. J. Am. Chem. Soc. 2003, 125, 13040.
6. (c) Cao, H.; Tokutake, N.; Regen, S. L. J. Am. Chem. Soc. 2003, 125, 16182.
7. (d) Krisovitch, S. M.; Regen, S. L. J. Am. Chem. Soc. 1992, 114, 9828.
8. (e) Tokutake, N.; Cao, H.; Jing, B.; Regen, S. L. J. Am. Chem. Soc. 2003, 125, 15764.
9. (f) Dewa, T.; Vigmond, S. J.; Regen, S. L. J. Am. Chem. Soc. 1996, 118, 3435.
10. (g) Sugahara, M.; Uragami, M.; Regen, S. L. J. Am. Chem. Soc. 2002, 124, 4253.
11. (a) Chatgilialoglu, C.; Ferreri, C.; Ballestri, M.; Mulazzani, Qu, G.; Landi, L. J. Am. Chem. Soc. 2000, 122, 4593.
12. (b) Ferreri, C.; Costantino, C.; Perrotta, L.; Landi, L.; Mulazzani, Q. G.; Chatgilialoglu, C. J. Am. Chem. Soc. 2001, 123, 4459.
13. (c) Ferreri, C.; Samadi, A.; Sassatelli, F.; Landi, L.; Chatgilialoglu, C. J. Am. Chem. Soc. 2004, 126, 1063.
14. (a) Jarrell, H. C.; Tulloch, A. P.; Smith, I. C. P. Biochemistry 1983, 22, 5611.
15. (b) Silvius, J. R.; McElhaney, R. N. Chem. Phys. Lipids 1979, 25, 125.
16. Due to the presence of two stereogenic centers in their cyclopropyl moiety, phospholipids 1 and 2 are mixtures of stereoisomers.
17. Gennis, R. B. Biomembranes: Molecular Structure and Function; Springer-Verlag: New York, 1989.
18. (a) Ipsen, J. H.; Karlstrom, G.; Mouritsen, O. G.; Wennerstrom, H.; Zuckermann, M. J. Biochim. Biophys. Acta 1987, 905, 162.
19. (b) Rubenstein, J. L. R.; Smith, B. A.; McConnell, H. M. Proc. Natl. Acad. Sci. U.S.A. 1979, 76, 15.
20. (c) McConnell, H. M.; Radhakrishnan, A. Biochim. Biophys. Acta 2003, 1610, 159.
21. (d) Sankaram, M. B.; Thompson, T. E. Proc. Natl. Acad. Sci., U.S.A. 1991, 88, 8686.
22. m = -20°C) [Ulrich, A. S.; Sami, M.; Watts, A. Biochim. Biophys. Acta 1994, 1191, 225]. Thus, 2 is a reasonable mimic of a trans-olefinic phospholipid by having a melting temperature that lies between that of a cis-olefinic (1) and a saturated phospholipid analogue (3c).
23. m = -20°C) [Ulrich, A. S.; Sami, M.; Watts, A. Biochim. Biophys. Acta 1994, 1191, 225]. Thus, 2 is a reasonable mimic of a trans-olefinic phospholipid by having a melting temperature that lies between that of a cis-olefinic (1) and a saturated phospholipid analogue (3c).
24. m = -20°C) [Ulrich, A. S.; Sami, M.; Watts, A. Biochim. Biophys. Acta 1994, 1191, 225]. Thus, 2 is a reasonable mimic of a trans-olefinic phospholipid by having a melting temperature that lies between that of a cis-olefinic (1) and a saturated phospholipid analogue (3c).
25. Simons, K.; Toomre, D. Nat. Rev. Mol. Cell Biol. 2000, 1, 31.