The thiyl radical-mediated isomerization of cis-monounsaturated fatty acid residues in phospholipids: A novel path of membrane damage?

Chemical Communications

Volumn , Issue 5, 1999, Pages 407-408

  Ferreri, Carla ^a,b   Costantino, Cristina ^a   Landi, Laura ^c   Mulazzani, Quinto G ^a   Chatgilialoglu, Chryssostomos ^a  

^a CNR   (Italy)

^b UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^c UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

LIPID; MONOUNSATURATED FATTY ACID; PHOSPHOLIPID; RADICAL; THIOL;

ARTICLE; ISOMERISM; LIPID VESICLE; MEMBRANE DAMAGE;

EID: 0033531412     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a809674k     Document Type: Article

References (23)

1. For reviews, see E. Niki, in Organic Peroxides, ed. W. Ando, Wiley, New York, 1992, pp. 764-787; L. C. R. Barclay, Can. J. Chem., 1993, 33, 1.
2. For reviews, see E. Niki, in Organic Peroxides, ed. W. Ando, Wiley, New York, 1992, pp. 764-787; L. C. R. Barclay, Can. J. Chem., 1993, 33, 1.
3. S. N. Muller, R. Batra, M. Senn, B. Giese, M. Kisel and O. Shadyro, J. Am. Chem. Soc., 1997, 119, 2795.
4. R. Holtwick, F. Meinhardt and H. Keweloh, Appl. Environ. Microbiol., 1997, 63, 4292; B. Loffeld and H. Keweloh, Lipids, 1996, 31, 811; H. Keweloh and H. J. Heipieper, Lipids, 1996, 31, 129.
5. R. Holtwick, F. Meinhardt and H. Keweloh, Appl. Environ. Microbiol., 1997, 63, 4292; B. Loffeld and H. Keweloh, Lipids, 1996, 31, 811; H. Keweloh and H. J. Heipieper, Lipids, 1996, 31, 129.
6. R. Holtwick, F. Meinhardt and H. Keweloh, Appl. Environ. Microbiol., 1997, 63, 4292; B. Loffeld and H. Keweloh, Lipids, 1996, 31, 811; H. Keweloh and H. J. Heipieper, Lipids, 1996, 31, 129.
7. R. L. Wolff and B. Entressangles, Biochim. Biophys. Acta, 1994, 1211, 198.
8. For a review, see P. E. Sonnet, Tetrahedron, 1980, 36, 557.
9. For catalytic hydrogenation of oils, see L. Ovesen, T. Leth and K. Hausen, Lipids, 1996, 31, 971 and references cited therein.
10. C. Chatgilialoglu, M. Ballestri, C. Ferreri and D. Vecchi, J. Org. Chem., 1995, 60, 3826.
11. For a review, see C. Chatgilialoglu and M. Guerra, in Supplement S: The Chemistry of Sulfur-containing Functional Groups, ed. S. Patai and Z. Rappoport, Wiley, London, 1993, pp. 363-394.
12. Liposomes a practical approach, ed. R. R. C. New, IRL Press, Oxford, 1990.
13. L. L. M. Van Deenen, in Progress in the Chemistry of Fats and Other Lipids. Vol. VIII, ed. R. T. T. Helman, Pergamon, Oxford, 1965, pp. 1-127.
14. C. Schöneich, U. Dillinger, F. von Bruchhausen and K.-D. Asmus, Arch. Biochem. Biophys., 1992, 292, 456.
15. L. R. C. Barclay, J. M. McNeil, J. J. VanKessel, B. Forrest, N. A. Porter, L. S. Lehman, K. J. Smith and J. C. Ellington Jr., J. Am. Chem. Soc., 1984, 106, 6740.
16. C. Schöneich, M. Bonifacic and K.-D. Asmus, Free Radical Res. Commun., 1989, 6, 393.
17. Transesterification in alkaline medium is preferable, as reported by: J. F. K. Kramer, V. Fellner, M. E. R. Dugan, F. D. Sauer, M. M. Mossoba and M. P. Yurawecz, Lipids, 1997, 32, 1219.
18. R. C. MacDonald, R. I. MacDonald, B. Ph. M. Menco, K. Takeshita, N. K. Subbarao and L. Hu, Biochim. Biophys. Acta, 1991, 1061, 297.
19. G. L. Newton, J. A. Aguilera, T. Kim, J. F. Ward and R. C. Fahey, Radiat. Res., 1996, 134, 215 and references cited therein.
20. For example, see R. Zhao, J. Lind, G. Merenyi and T. E. Eriksen, J. Am. Chem. Soc., 1994, 116, 12010; M. S. Akhlaq and C. von Sonntag, J. Am. Chem. Soc., 1986, 108, 3542.
21. For example, see R. Zhao, J. Lind, G. Merenyi and T. E. Eriksen, J. Am. Chem. Soc., 1994, 116, 12010; M. S. Akhlaq and C. von Sonntag, J. Am. Chem. Soc., 1986, 108, 3542.
22. G. Stark, Biochim. Biophys. Acta , 1991, 1071, 103 and references cited therein.
23. After completion of this manuscript, the following paper on thiyl-induced cis-trans isomerization of linoleate derivatives has appeared: J. Schwinn, H. Sprinz, K. Drößler, S. Leistner and O. Brede, Int. J. Radiat. Biol., 1998, 74, 359.