Synthesis, discovery, and quantitation of dihomo-isofurans: Biomarkers for in vivo adrenic acid peroxidation

Angewandte Chemie - International Edition

Volumn 53, Issue 24, 2014, Pages 6249-6252

  De La Torre, Aurélien ^a   Lee, Yiu Yiu ^d   Oger, Camille ^a   Sangild, Per Torp ^c   Durand, Thierry ^a   Lee, Jetty Chung Yung ^b   Galano, Jean Marie ^a  

^a UNIV MONTPELLIER   (France)

^b UNIVERSITY OF HONG KONG   (Hong Kong)

^c UNIVERSITY OF COPENHAGEN   (Denmark)

^d NONE

Author keywords

biomarkers; lipids; mass spectrometry; oxidation; total synthesis

Indexed keywords

LIPIDS; MASS SPECTROMETRY; METABOLITES; OXIDATION; POLYUNSATURATED FATTY ACIDS;

DIVERGENT APPROACH; LIPID PEROXIDATION; LIPIDOMICS; NON-ENZYMATIC; PEROXIDATION; POLYUNSATURATED FATTY ACIDS (PUFAS); TOTAL SYNTHESIS; WHITE MATTER;

BIOMARKERS;

ADRENIC ACID; FURAN DERIVATIVE; UNSATURATED FATTY ACID;

CHEMISTRY; LIPID PEROXIDATION; SYNTHESIS;

FATTY ACIDS, UNSATURATED; FURANS; LIPID PEROXIDATION;

EID: 84902113684     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201402440     Document Type: Article

References (24)

1. J. D. Morrow, K. E. Hill, R. F. Burk, T. M. Nammour, K. F. Badr, L. J. Roberts, Proc. Natl. Acad. Sci. USA 1990, 87, 9383-9387.
2. L. J. Roberts II, T. J. Montine, W. R. Markesbery, A. R. Tapper, P. Hardy, S. Chemtob, W. D. Dettbarn, J. D. Morrow, J. Biol. Chem. 1998, 273, 13605-13612.
3. U. Jahn, J.-M. Galano, T. Durand, Angew. Chem. 2008, 120, 5978-6041
4. Angew. Chem. Int. Ed. 2008, 47, 5894-5955.
5. J. P. Fessel, N. A. Porter, K. P. Moore, J. R. Sheller, L. J. Roberts, Proc. Natl. Acad. Sci. USA 2002, 99, 16713-16718.
6. W.-L. Song, J. A. Lawson, D. Reilly, J. Rokach, C.-T. Chang, B. Giasson, G. A. FitzGerald, J. Biol. Chem. 2008, 283, 6-16.
7. E. R. Skinner, C. Watt, J. a. O. Besson, P. V. Best, Brain 1993, 116, 717-725.
8. C. De Felice, C. Signorini, T. Durand, C. Oger, A. Guy, V. Bultel-Ponce, J.-M. Galano, L. Ciccoli, S. Leoncini, M. D'Esposito, S. Filosa, A. Pecorelli, G. Valacchi, J. Hayek, J. Lipid Res. 2011, 52, 2287-2297.
9. C.-Y. J. Lee, R. C. S. Seet, S. H. Huang, L. H. Long, B. Halliwell, Antioxid. Redox Signaling 2009, 11, 407-420.
10. D. F. Taber, J. P. Fessel, L. J. Roberts II, Prostaglandins Other Lipid Mediators 2004, 73, 47-50.
11. J. R. Falck, L. Manmohan Reddy, K. Byun, W. B. Campbell, X.-Y. Yi, Bioorg. Med. Chem. Lett. 2007, 17, 2634-2638.
12. D. F. Taber, P. Gu, R. Li, J. Org. Chem. 2009, 74, 5516-5522.
13. D. F. Taber, Z. Zhang, J. Org. Chem. 2006, 71, 926-933.
14. D. F. Taber, Y. Pan, X. Zhao, J. Org. Chem. 2004, 69, 7234-7240.
15. M. Valli, P. Bruno, D. Sbarbada, A. Porta, G. Vidari, G. Zanoni, J. Org. Chem. 2013, 78, 5556-5567.
16. T. Zheng, R. S. Narayan, J. M. Schomaker, B. Borhan, J. Am. Chem. Soc. 2005, 127, 6946-6947.
17. B. H. Lipshutz, D. Buzard, C. Olsson, K. Noson, Tetrahedron 2004, 60, 4443-4449.
18. D. J. Phillips, K. S. Pillinger, W. Li, A. E. Taylor, A. E. Graham, Tetrahedron 2007, 63, 10528-10533.
19. M. Oikawa, A. Wada, F. Okazaki, S. Kusumoto, J. Org. Chem. 1996, 61, 4469-4471.
20. Z.-C. Feng, E. L. Roberts Jr., T. J. Sick, M. Rosenthal, Brain Res. 1988, 445, 280-288.
21. M. L. S. Chung, K. Y. E. Lee, C.-Y. J. Lee, Food Chem. Toxicol. 2013, 53, 205-213.
22. R. Solberg, M. Longini, F. Proietti, P. Vezzosi, O. D. Saugstad, G. Buonocore, Free Radical Biol. Med. 2012, 53, 1061-1067.
23. D. R. Euston, A. J. Gruber, B. L. McNaughton, Neuron 2012, 76, 1057-1070.
24. A. C. Andreazza, J.-F. Wang, F. Salmasi, L. Shao, L. T. Young, J. Neurochem. 2013, 127, 552-561.