A continuous visible light spectrophotometric approach to accurately determine the reactivity of radical-trapping antioxidants

Journal of Organic Chemistry

Volumn 81, Issue 3, 2016, Pages 737-744

  Haidasz, Evan A ^a   Van Kessel, Antonius T M ^a   Pratt, Derek A ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ASSAYS; CHROMOPHORES; KINETICS; OXIDATION; RATE CONSTANTS; REACTION KINETICS; SOLUTIONS; SOLVENTS; SPECTROPHOTOMETERS; SPECTROPHOTOMETRY; STYRENE;

ANTIOXIDANT ASSAYS; HYDROCARBON SUBSTRATES; HYDROPEROXIDE FORMATIONS; INHIBITION RATE CONSTANTS; KINETIC ISOTOPE EFFECTS; RADICAL TRAPPING; REACTION PROGRESS; SYNERGISTIC INTERACTION;

ANTIOXIDANTS;

ANTIOXIDANT; RADICAL; 4,4-DIFLUORO-4-BORA-3A,4A-DIAZA-S-INDACENE; BORON DERIVATIVE; FREE RADICAL; OXIDIZING AGENT; PERHYDROXYL RADICAL; PEROXIDE;

ABSORPTION SPECTROSCOPY; ANTIOXIDANT ASSAY; AQUEOUS SOLUTION; ARTICLE; AUTOOXIDATION; CHROMATOPHORE; LIGHT; LIPID BILAYER; LIPID OXIDATION; PHOSPHOLIPID BILAYER; PULSE RADIOLYSIS; RATE CONSTANT; SPECTROPHOTOMETRY; STOICHIOMETRY; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECTS; LIPID PEROXIDATION; METABOLISM;

ANTIOXIDANTS; BORON COMPOUNDS; FREE RADICALS; LIGHT; LIPID PEROXIDATION; MOLECULAR STRUCTURE; OXIDANTS; PEROXIDES; SPECTROPHOTOMETRY;

EID: 84957540112     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.5b02183     Document Type: Article

References (44)

1. Ingold, K. U. Chem. Rev. 1961, 61, 563-589 10.1021/cr60214a002
2. Ingold, K. U.; Pratt, D. A. Chem. Rev. 2014, 114, 9022-9046 10.1021/cr500226n
3. Valgimigli, L.; Pratt, D. A. In Encyclopedia of Radicals in Chemistry, Biology and Materials; Chatgilialoglu, C.; Studer, A., Eds.; John Wiley & Sons,: Chichester, UK, 2012.
4. Li, B.; Pratt, D. A. Free Radical Biol. Med. 2015, 82, 187-202 10.1016/j.freeradbiomed.2015.01.020
5. Amorati, R.; Valgimigli, L. Free Radical Res. 2015, 49, 633-649 10.3109/10715762.2014.996146
6. Hanthorn, J. J.; Haidasz, E.; Gebhardt, P.; Pratt, D. A. Chem. Commun. 2012, 48, 10141-10143 10.1039/c2cc35214a
7. Re, R.; Pellegrini, N.; Proteggente, A.; Pannala, A.; Yang, M.; Rice-Evans, C. Free Radical Biol. Med. 1999, 26, 1231-1237 10.1016/S0891-5849(98)00315-3
8. Benzie, I. F.; Strain, J. J. Anal. Biochem. 1996, 239, 70-76 10.1006/abio.1996.0292
9. Blois, M. S. Nature 1958, 181, 1199-1200 10.1038/1811199a0
10. Huang, D.; Ou, B.; Prior, R. L. J. Agric. Food Chem. 2005, 53, 1841-1856 10.1021/jf030723c
11. Foti, M. J. Agric. Food Chem. 2015, 63, 8765-8776 10.1021/acs.jafc.5b03839
12. Litwinienko, G.; Ingold, K. U. Acc. Chem. Res. 2007, 40, 222-230 10.1021/ar0682029
13. Kang, H. C.; Haugland, R. P. Long Wavelength Chemically Reactive Dipyrrometheneboron Difluoride Dyes and Conjugates. US5451663 A, 1993.
14. Drummen, G. P.; van Liebergen, L. C.; Op den Kamp, J. A.; Post, J. A. Free Radical Biol. Med. 2002, 33, 473-490 10.1016/S0891-5849(02)00848-1
15. Yoshida, Y.; Shimakawa, S.; Itoh, N.; Niki, E. Free Radic. Res. 2003, 37, 861-872 10.1080/1071576031000148736
16. Kang, H. C.; Haugland, R. P. Ethenyl-Substituted Dipyrrometheneboron Difluoride Dyes and Their Synthesis. US5187288, 1993.
17. De Cremer, G.; Roeffaers, M. B. J.; Bartholomeeusen, E.; Lin, K.; Dedecker, P.; Pescarmona, P. P.; Jacobs, P. A.; De Vos, D. E.; Hofkens, J.; Sels, B. F. Angew. Chem., Int. Ed. 2010, 49, 908-911 10.1002/anie.200905039
18. Naguib, Y. M. Anal. Biochem. 1998, 265, 290-298 10.1006/abio.1998.2931
19. Hammond, G. S.; Sen, J. N.; Boozer, C. E. J. Am. Chem. Soc. 1955, 77, 3244-3248 10.1021/ja01617a028
20. Van Hook, J. P.; Tobolsky, A. V. J. Am. Chem. Soc. 1958, 80, 779-782 10.1021/ja01537a006
21. Howard, J.; Ingold, K. Can. J. Chem. 1967, 45, 793-802 10.1139/v67-132
22. 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 10.1021/ja00310a049
23. Valgimigli, L.; Amorati, R.; Petrucci, S.; Pedulli, G. F.; Hu, D.; Hanthorn, J. J.; Pratt, D. A. Angew. Chem., Int. Ed. 2009, 48, 8348-8351 10.1002/anie.200903360
24. Valgimigli, L.; Bartolomei, D.; Amorati, R.; Haidasz, E.; Hanthorn, J. J.; Nara, S. J.; Brinkhorst, J.; Pratt, D. A. Beilstein J. Org. Chem. 2013, 9, 2781-2792 10.3762/bjoc.9.313
25. Brownlie, I. T.; Ingold, K. U. Can. J. Chem. 1966, 44, 861-868 10.1139/v66-127
26. Hanthorn, J. J.; Amorati, R.; Valgimigli, L.; Pratt, D. A. J. Org. Chem. 2012, 77, 6895-6907 10.1021/jo301012x
27. Burton, G. W.; Ingold, K. U. J. Am. Chem. Soc. 1981, 103, 6472-6477 10.1021/ja00411a035
28. Jensen, R. K.; Korcek, S.; Zinbo, M.; Gerlock, J. L. J. Org. Chem. 1995, 60, 5396-5400 10.1021/jo00122a014
29. Haidasz, E. A.; Shah, R.; Pratt, D. A. J. Am. Chem. Soc. 2014, 136, 16643-16650 10.1021/ja509391u
30. Enes, R. F.; Tomé, A. C.; Cavaleiro, J. A. S.; Amorati, R.; Fumo, M. G.; Pedulli, G. F.; Valgimigli, L. Chem.-Eur. J. 2006, 12, 4646-4653 10.1002/chem.200501495
31. von Sonntag, C.; Schuchmann, H.-P. Angew. Chem., Int. Ed. Engl. 1991, 30, 1229-1253 10.1002/anie.199112291
32. Neta, P.; Huie, R. E.; Ross, A. B. J. Phys. Chem. Ref. Data 1990, 19, 413-513 10.1063/1.555854
33. Howard, J. A.; Ingold, K. U. Can. J. Chem. 1969, 47, 3809-3815 10.1139/v69-635
34. Howard, J. A. Adv. Free Radical Chem. 1972, 4, 49-173
35. Alfassi, Z. B.; Huie, R. E.; Kumar, M.; Neta, P. J. Phys. Chem. 1992, 96, 767-770 10.1021/j100181a045
36. -1 for cumylperoxyls). The difference (13.8-fold) can be rationalized by the greater electrophilicity of the THF-derived peroxyl radical compared to the cumylperoxyl radical and the significant polar effects known to operate in the transition states of radical additions to alkenes. For a discussion, see: Russell, G. A. In Free Radicals; Kochi, J. K., Ed.; Wiley: New York, 1973; Vol. 1, pp 275-332.
37. Snelgrove, D. W.; Lusztyk, J.; Banks, J. T.; Mulder, P.; Ingold, K. U. J. Am. Chem. Soc. 2001, 123, 469-477 10.1021/ja002301e
38. See: Wayner, D. D. M.; Burton, G. W.; Ingold, K. U. Biochim. Biophys. Acta, Gen. Subj. 1986, 884, 119-123 and references cited therein 10.1016/0304-4165(86)90234-5
39. Doba, T.; Burton, G. W.; Ingold, K. U. Biochim. Biophys. Acta, Lipids Lipid Metab. 1985, 835, 298-303 10.1016/0005-2760(85)90285-1
40. Barclay, L. R. C.; Locke, S. J.; MacNeil, J. M. Can. J. Chem. 1983, 61, 1288-1290 10.1139/v83-225
41. Nam, T.-G.; Nara, S. J.; Zagol-Ikapitte, I.; Cooper, T.; Valgimigli, L.; Oates, J. A.; Porter, N. A.; Boutaud, O.; Pratt, D. A. Org. Biomol. Chem. 2009, 7, 5103-5112 10.1039/b912528k
42. Hanthorn, J. J.; Valgimigli, L.; Pratt, D. A. J. Org. Chem. 2012, 77, 6908-6916 10.1021/jo301013c
43. Ryskiewicz, R. M.; Silverstein, E. E.; Willard, C. Org. Synth. 1956, 36, 74 10.15227/orgsyn.036.0074
44. Hanthorn, J. J.; Pratt, D. A. J. Org. Chem. 2012, 77, 276-284 10.1021/jo201862s