The synthesis and aqueous superoxide anion scavenging of water-dispersible lutein esters

Bioorganic and Medicinal Chemistry Letters

Volumn 16, Issue 4, 2006, Pages 775-781

  Nadolski, Geoff ^a   Cardounel, Arturo J ^b   Zweier, Jay L ^b   Lockwood, Samuel F ^a  

^a HAWAII BIOTECH INC   (United States)

^b OHIO STATE UNIVERSITY   (United States)

Author keywords

Aqueous dispersibility; Carotenoid derivatives; Carotenoids; DEPMPO; Electron paramagnetic resonance; EPR; Lutein; Lutein diphosphate sodium salt; Lutein disuccinate sodium salt; Spin traps; Superoxide anion

Indexed keywords

CAROTENOID; ESTER DERIVATIVE; LUTEIN (BETA EPSILON CAROTENE 3,3' DIOL)DERIVATIVE; LUTEIN DIPHOSPHATE; LUTEIN DISUCCINATE; PHOSPHATE; SODIUM; SUCCINIC ACID; SUPEROXIDE; UNCLASSIFIED DRUG; XANTHOPHYLL;

AQUEOUS SOLUTION; ARTICLE; DISPERSION; DOSE RESPONSE; DRUG FORMULATION; DRUG SYNTHESIS; ELECTRON SPIN RESONANCE; ESTERIFICATION; SCAVENGING SYSTEM;

ANIONS; BIOLOGICAL ASSAY; DOSE-RESPONSE RELATIONSHIP, DRUG; ELECTRON SPIN RESONANCE SPECTROSCOPY; ESTERS; FREE RADICAL SCAVENGERS; HUMANS; LUTEIN; MOLECULAR STRUCTURE; NEUTROPHILS; SOLUBILITY; STRUCTURE-ACTIVITY RELATIONSHIP; SUPEROXIDES; WATER;

EID: 30344447260     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2005.11.024     Document Type: Article

References (31)

1. A.J. Cardounel, C. Dumitrescu, J.L. Zweier, and S.F. Lockwood Biochem. Biophys. Res. Commun. 307 2003 704
2. F. Zsila, M. Simonyi, and S.F. Lockwood Bioorg. Med. Chem. Lett. 13 2003 4093
3. D.A. Frey, E.W. Kataisto, J.L. Ekmanis, S. O'Malley, and S.F. Lockwood Org. Process Res. Dev. 8 2004 796
4. G.J. Gross, and S.F. Lockwood Life Sci. 75 2004 215
5. H.L. Jackson, A.J. Cardounel, J.L. Zweier, and S.F. Lockwood Bioorg. Med. Chem. Lett. 14 2004 3985
6. F. Zsila, I. Fitos, Z. Bikádi, M. Simonyi, H.L. Jackson, and S.F. Lockwood Bioorg. Med. Chem. Lett. 14 2004 5357
7. S.F. Lockwood, S. O'Malley, and G.L. Mosher J. Pharm. Sci. 92 2003 922
8. B.J. Foss, S.N. Naess, H.R. Sliwka, and V. Partali Angew. Chem., Int. Ed. 42 2003 5237
9. B.J. Foss, H.R. Sliwka, V. Partali, A.J. Cardounel, J.L. Zweier, and S.F. Lockwood Bioorg. Med. Chem. Lett. 14 2004 2807
10. L.M. Hix, S.F. Lockwood, and J.S. Bertram Cancer Lett. 211 2004 25
11. L.M. Hix, S.F. Lockwood, and J.S. Bertram Redox Rep. 9 2004 181
12. J.S. Bertram Nutr. Rev. 57 1999 182
13. P.E. Bowen, S.M. Herbst-Espinosa, E.A. Hussain, and M. Stacewicz-Sapuntzakis J. Nutr. 132 2002 3668
14. L.A. Showalter, S.A. Weinman, M. Østerlie, and S.F. Lockwood Comp. Biochem. Physiol. C: Toxicol. Pharmacol. 137 2004 227
15. P. Buchwald, and N. Bodor Pharmazie 59 2004 396
16. S. Richer, W. Stiles, L. Statkute, J. Pulido, J. Frankowski, D. Rudy, K. Pei, M. Tsipursky, and J. Nyland Optometry 75 2004 216
17. J.T. Landrum, and R.A. Bone Arch. Biochem. Biophys. 385 2001 28
18. B. Olmedilla, F. Granado, I. Blanco, and M. Vaquero Nutrition 19 2003 21
19. E.H. Lee, D. Faulhaber, K.M. Hanson, W. Ding, S. Peters, S. Kodali, and R.D. Granstein J. Invest. Dermatol. 122 2004 510
20. 2 (3.76 g, 14.8 mmol). The mixture was stirred at 0°C for 10 min or until the solution became clear and colorless. The solution was then stirred at rt for 10 min and used directly in the next step.
21. A. Fraticelli, C.V. Serrano Jr., B.S. Bochner, M.C. Capogrossi, and J.L. Zweier Biochim. Biophys. Acta 1310 1996 251
22. P. Wang, and J.L. Zweier J. Biol. Chem. 271 1996 29223
23. C. Lee, K. Miura, X. Liu, and J.L. Zweier J. Biol. Chem. 275 2000 38965
24. V. Roubaud, S. Sankarapandi, P. Kuppusamy, P. Tordo, and J.L. Zweier Anal. Biochem. 247 1997 404
25. J.K. Stowell, and T.S. Widlanski Tetrahedron Lett. 36 1995 1825
26. P. Savignac, and G. Lavielle Bull. Soc. Chim. Fr. 7 1974 1506
27. D.J.H. Smith, K.K. Ogilvie, and M.F. Gillen Tetrahedron Lett. 21 1980 861
28. C.J. Salomon, and E. Breuer Tetrahedron Lett. 36 1995 6759
29. F. Zsila, Z. Bikádi, Z. Keresztes, J. Deli, and M. Simonyi J. Phys. Chem. B 105 2001 9413
30. F. Zsila, Z. Bikádi, J. Deli, and M. Simonyi Chirality 13 2001 446
31. P.A. Thürmann, W. Schalch, J.C. Aebischer, U. Tenter, and W. Cohn Am. J. Clin. Nutr. 82 2005 88