Design and synthesis of a BODIPY-α-tocopherol adduct for use as an off/on fluorescent antioxidant indicator

Journal of the American Chemical Society

Volumn 129, Issue 7, 2007, Pages 1842-1843

  Oleynik, Paul ^a   Ishihara, Yoshihiro ^a   Cosa, Gonzalo ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; ALPHA TOCOPHEROL; ANTIOXIDANT; BORON DERIVATIVE; CHROMAN DERIVATIVE; DIPYRROMETHENEBORON DIFLUORIDE; DYE; FLUORIDE; FREE RADICAL; HYDROPEROXIDE; INDICATOR; PEROXY RADICAL; TOLUENE; TROLOX C; UNCLASSIFIED DRUG;

APOPTOSIS; ARTICLE; AUTOOXIDATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; DEGENERATIVE DISEASE; DEGRADATION; ELECTRON TRANSPORT; FLUORESCENCE; HYDROPHOBICITY; LIPID MEMBRANE; QUANTUM YIELD; REACTION ANALYSIS; SIGNAL TRANSDUCTION; SYNTHESIS;

ALPHA-TOCOPHEROL; ANTIOXIDANTS; BORON COMPOUNDS; DRUG DESIGN; FLUORESCENT DYES; FREE RADICALS; HYDROPHOBICITY; KINETICS;

EID: 33847264426     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja066789g     Document Type: Article

References (21)

1. Bowry, V. W.; Ingold, K. U. Acc. Chem. Res. 1999, 32, 27-34.
2. Steinberg, D. Lancet 1995, 346, 36-38.
3. (a) Barnham, K. J.; Masters, C. L.; Bush, A. I. Nat. Rev. Drug Discovery 2004, 3, 205-214.
4. (b) Montine, T. J.; Neely, M. D.; Quinn, J. F.; Beal, M. F.; Markesbery, W. R.; Roberts, L. J.; Morrow, J. D. Free Radical Biol. Med. 2002, 33, 620-626.
5. Kagan, V. E.; Fabisiak, J. P.; Shvedova, A. A.; Tyurina, Y. Y.; Tyurin, V. A.; Schor, N. F.; Kawai, K. FEBS Lett. 2000, 477, 1-7.
6. Burton, G. W.; Doba, T.; Gabe, E.; Hughes, L.; Lee, F. L.; Prasad, L.; Ingold, K. U. J. Am. Chem. Soc. 1985, 107, 7053-7065.
7. Niki, E.; Noguchi, N. Acc. Chem. Res. 2004, 37, 45-51.
8. Burton, G. W.; Ingold, K. U. Acc. Chem. Res. 1986, 19, 194-201.
9. Barclay, L. R. C. Can. J. Chem. 1993, 71, 1-16.
10. (a) Liebler, D. C.; Baker, P. F.; Kaysen, K. L. J. Am. Chem. Soc. 1990, 112, 6995-7000.
11. (b) Liebler, D. C.; Burr, J. A.; Matsumoto, S.; Matsuo, M. Chem. Res. Toxicol. 1993, 6, 351-355.
12. Burton, G. W.; Ingold, K. U. J. Am. Chem. Soc. 1981, 103, 6472-6477.
13. (a) Yoshida, Y.; Shimakawa, S.; Itoh, N.; Niki, E. Free Radical Res. 2003, 37, 861-872.
14. (b) Naguib, Y. M. A. Anal. Biochem. 1998, 265, 290-298.
15. (a) de Silva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515-1566.
16. (b) Ueno, T.; Urano, Y.; Kojima, H.; Nagano, T. J. Am. Chem. Soc. 2006, 128, 10640-10641.
17. (c) Ueno, T.; Urano, Y.; Setsukinai, K.; Takakusa, H.; Kojima, H.; Kikuchi, K.; Ohkubo, K.; Fukuzumi, S.; Nagano, T. J. Am. Chem. Soc. 2004, 126, 14079-14085.
18. (d) Gabe, Y.; Urano, Y.; Kikuchi, K.; Kojima, H.; Nagano, T. J. Am. Chem. Soc. 2004, 126, 3357-3367.
19. Johnson, I. D.; Kang, H. C.; Haugland, R. P. Anal. Biochem. 1991, 198, 228-237.
20. Heyne, B.; Maurel, V.; Scaiano, J. C. Org. Biomol. Chem. 2006, 4, 802-807.
21. Boozer, C. E.; Hammond, G. S.; Hamilton, C. E.; Sen, J. N. J. Am. Chem. Soc. 1955, 77, 3233-3237.