Environmentally persistent free radicals (EPFRs). 1. Generation of reactive oxygen species in aqueous solutions

Environmental Science and Technology

Volumn 45, Issue 19, 2011, Pages 8559-8566

  Khachatryan, Lavrent ^a   Vejerano, Eric ^a   Lomnicki, Slawo ^a   Dellinger, Barry ^a  

^a LOUISIANA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

APROTIC; AQUEOUS SOLVENTS; CATALYTIC CYCLES; ELECTRON PARAMAGNETIC RESONANCE SPECTROSCOPY; FAST TRANSFORMATION; HYDROXYL RADICAL FORMATION; HYDROXYL RADICALS; INCUBATION TIME; INTERMEDIATE PRODUCT; REACTIVE OXYGEN SPECIES; SPIN TRAP; SUPEROXIDE ANION RADICALS; SUPEROXIDE DISMUTASES; SUPEROXIDE RADICAL; SUPEROXIDES;

ACETONITRILE; DIMETHYL SULFOXIDE; FREE RADICALS; HYDROGEN; HYDROGEN PEROXIDE; MOLECULAR OXYGEN; ORGANIC SOLVENTS; OXIDATION; PARAMAGNETIC RESONANCE; PARAMAGNETISM;

ELECTRON SPIN RESONANCE SPECTROSCOPY;

5,5 DIMETHYL 1 PYRROLINE 1 OXIDE; ACETONITRILE; CATALASE; COPPER OXIDE; DIMETHYL SULFOXIDE; ENVIRONMENTALLY PERSISTENT FREE RADICAL; FREE RADICAL; HYDROGEN PEROXIDE; HYDROXYL RADICAL; OXYGEN; PHENOL DERIVATIVE; REACTIVE OXYGEN METABOLITE; SILICON; SUPEROXIDE; SUPEROXIDE DISMUTASE; UNCLASSIFIED DRUG;

ANION; AQUEOUS SOLUTION; CATALYSIS; CHLOROPHENOL; COPPER COMPOUND; ELECTRON SPIN RESONANCE; ENZYME ACTIVITY; EXPERIMENTAL STUDY; FREE RADICAL; HYDROGEN PEROXIDE; HYDROXYL RADICAL; PERSISTENCE; SILICA; TRANSFORMATION;

AQUEOUS SOLUTION; ARTICLE; CONCENTRATION (PARAMETERS); ELECTRON SPIN RESONANCE;

ANIMALS; CATALASE; CATTLE; CHLOROPHENOLS; CYCLIC N-OXIDES; ELECTRON SPIN RESONANCE SPECTROSCOPY; ENVIRONMENTAL POLLUTANTS; HYDROGEN PEROXIDE; HYDROXYL RADICAL; IRON; OXIDATION-REDUCTION; REACTIVE OXYGEN SPECIES; SOLUTIONS; SOLVENTS; SUPEROXIDE DISMUTASE; SUPEROXIDES; WATER;

EID: 80053410645     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es201309c     Document Type: Article

References (53)

1. Dellinger, B.; Pryor, W. A.; Ceuto, R.; Squadrito, G. L.; Hedge, V.; Deutsch, W. A. Role of free radicals in the toxicity of airborne fine particulate matter Chem. Res. Toxicol. 2001, 14, 1371-1377 (Pubitemid 32988407)
2. Maskos, Z.; Khachatryan, L.; Dellinger, B. Precursors of radicals in tobacco smoke and the role of particulate matter in forming and stabilizing radicals Energy Fuels 2005, 19, 2466-2473 (Pubitemid 41787183)
3. Knaapen, A. M.; Shi, T. M.; Borm, P. J. A.; Schins, R. P. F. Soluble metals as well as the insoluble particle fraction are involved in cellular DNA damage induced by particulate matter Mol. Cell. Biochem. 2002, 234 (1) 317-326 (Pubitemid 34777871)
4. Dellinger, B.; Pryor, W. A.; Cueto, R.; Squadrito, G. L.; Deutsch, W. A. Combustion-generated radicals and their role in the toxicity of fine particulate Organohalogen Compd. 2000, 46, 302-305
5. Cormier, S. A.; Lomnicki, S.; Backes, W.; Dellinger, B. Origin and health impacts of emissions of toxic by-products and fine particles from combustion and thermal treatment of hazardous wastes and materials Environ. Health Perspect. 2006, 114, 810-817 (Pubitemid 43871726)
6. Pryor, W. A. Oxy-Radicals and Related Species: Their Formation, Lifetimes, and Reactions Annu. Rev. Physiol. 1986, 48, 657-667 (Pubitemid 16047640)
7. Finkelstein, E.; Rosen, G. M.; Rauckman, E. J. Production of Hydroxyl Radical by Decomposition of Superoxide Spin-Trapped Adducts Mol. Pharmacol. 1982, 21 (2) 262-265 (Pubitemid 12139822)
8. Forshult, S.; Lagercra, C. Use of Nitroso Compounds as Scavengers for Study of Short-Lived Free Radicals in Organic Reactions. Acta Chem. Scand. 1969, 23 (2), 522 -&.
9. Janzen, E. G.; Blackbur, B. J. Detection and Identification of Short-Lived Free Radicals by an Electron Spin Resonance Trapping Technique. J. Am. Chem. Soc. 1968, 90 (21), 5909 -&.
10. Truong, H.; Lomnicki, S.; Dellinger, B. Potential for Misidentification of Environmentally Persistent Free Radicals as Molecular Pollutants in Particulate Matter Environ. Sci. Technol. 2010, 44 (6) 1933-1939
11. Nakagawa, K. Is quartz flat cell useful for the detection of superoxide radicals? J. Active Oxygen Free Radical 1994, 5, 81-85
12. Fubini, B.; Mollo, L.; Giamello, E. Free radical generation at the solid/liquid interface in iron containing minerals Free Radical Res. 1995, 23 (6) 593-614
13. Tomita, M.; Okuyama, T.; Watanabe, S.; Watanabe, H. Quantitation of the Hydroxyl Radical Adducts of Salicylic-Acid by Micellar Electrokinetic Capillary Chromatography-Oxidizing Species Formed by a Fenton Reaction Arch. Toxicol. 1994, 68 (7) 428-433 (Pubitemid 24246343)
14. Yamazaki, I.; Piette, L. H. EPR Spin-Trapping Study on the Oxidizing Species Formed in the Reaction of the Ferrous Ion with Hydrogen-Peroxide J. Am. Chem. Soc. 1991, 113 (20) 7588-7593
15. Zhu, B. Z.; Har-El, R.; Kitrossky, N.; Chevion, M. New modes of action of desferrioxamine: scavenging of semiquinone radical and stimulation of hydrolysis of tetrachlorohydroquinone (vol 24, pg 360, 1997) Free Radical Biol. Med. 1998, 24 (5) 880 (Pubitemid 28169577)
16. Finkelstein, E.; Rosen, G. M.; Rauckman, E. J. Spin Trapping-Kinetics of the Reaction of Superoxide and Hydroxyl Radicals with Nitrones J. Am. Chem. Soc. 1980, 102 (15) 4994-4999
17. Yordanov, N. D.; Ranguelova, K. Quantitative electron paramagnetic resonance and spectrophotometric determination of the free radical 4-hydroxy-2,2,6,6-tetramethylpiperidinyloxy Spectrochim. Acta, Part a: Mol. Biomol. Spectrosc. 2000, 56 (2) 373-378
18. Burkitt, M. J.; Tsang, S. Y.; Tam, S. C.; Bremner, I. Generation of 5,5-Dimethyl-1-Pyrroline N-Oxide Hydroxyl and Scavenger Radical Adducts from Copper/H2o2Mixtures-Effects of Metal-Ion Chelation and the Search for High-Valent Metal-Oxygen Intermediates Arch. Biochem. Biophys. 1995, 323 (1) 63-70
19. Hanna, P. M.; Chamulitrat, W.; Mason, R. P. When Are Metal Ion-Dependent Hydroxyl and Alkoxyl Radical Adducts of 5,5-Dimethyl-1-Pyrroline N-Oxide Artifacts Arch. Biochem. Biophys. 1992, 296 (2) 640-644
20. Chamulitrat, W.; Iwahashi, H.; Kelman, D. J.; Mason, R. P. Evidence against the 1-2-2-1 Quartet Dmpo Spectrum as the Radical Adduct of the Lipid Alkoxyl Radical Arch. Biochem. Biophys. 1992, 296 (2) 645-649
21. Finkelstein, E.; Rosen, G. M.; Rauckman, E. J. Spin Trapping of Superoxide and Hydroxyl Radical-Practical Aspects Arch. Biochem. Biophys. 1980, 200 (1) 1-16
22. Makino, K.; Hagiwara, T.; Murakami, A. Fundamental-Aspects of Spin Trapping with Dmpo Radiat. Phys. Chem. 1991, 37 (5-6) 657-665
23. Zhu, B. Z.; Har-El, R.; Kitrossky, N.; Chevion, M. New modes of action of desferrioxamine: scavenging of semiquinone radical and stimulation of hydrolysis of tetrachlorohydroquinone Free Radical Biol. Med. 1998, 24 (5) 880 (Pubitemid 28169577)
24. 2 Reactive Species in Oxygen-Toxicity in Biology J. Biol. Chem. 1990, 265 (23) 13589-13594
25. Fee, J. A.; Valentine, J. S. Chemical and Physical Properties of Superoxide. In Superoxide and Superoxide Dismutases; Michelson, A M.; McCord, J. M.; Fridovich, I., Eds.; Academic Press: New York, 1977; pp 19-60.
26. Halliwell, B.; Gutteridge, J. M. C. Free Radicals and Metal Ions in Human Disease in Methods in Enzymology Methods Enzymol. 1990, 186, 1-85 (Pubitemid 20279941)
27. Bielski, B. H. J.; Allen, A. O. Mechanism of Disproportionation of Superoxide Radicals J. Phys. Chem. 1977, 81 (11) 1048-1050
28. Buettner, G. R.; Oberley, L. W. Considerations in Spin Trapping of Superoxide and Hydroxyl Radical in Aqueous Systems Using 5,5-Dimethyl-1- Pyrroline-1-Oxide Biochem. Biophys. Res. Commun. 1978, 83 (1) 69-74 (Pubitemid 8378945)
29. Villamena, F. A.; Xia, S.; Merle, J. K. Reactivity of superoxide radical anion with cyclic nitrones: Role of intramolecular H-bond and electrostatic effects J. Am. Chem. Soc. 2007, 129 (26) 8177-8191 (Pubitemid 47035131)
30. Cabelli, D. E.; Allen, D.; Bielski, B. H. J.; Holcman, J. The Interaction between Cu(I) Superoxide-Dismutase and Hydrogen-Peroxide J. Biol. Chem. 1989, 264 (17) 9967-9971
31. Buettner, G. R.; Mason, R. P. Critical reviews of oxidative stress and aging: Advances in basic science, diagnostics and intervention; Cutler, R. G.; Rodrigues, H., Eds.; World Scientific Publishing Co., National Academies Press 2003; Chapter 2, pp 27-38.
32. Zang, L. Y.; Stone, K.; Pryor, W. A. Detection of Free Radicals in Aqeous Extracts of Cigarete Tar by ESR Free Radical Biol. Med. 1995, 19, 161-167
33. Pryor, W. A.; Stone, K.; Zang, L.-Y.; Bermudez, E. Fractionation of Aqueous Cigarette Tar Extracts: Fractions that Contain the Tar Radical Cause DNA Damage Chem. Res. Toxicol. 1998, 11, 441-448 (Pubitemid 28242488)
34. Arroyo, C. M.; Kramer, J. H.; Dickens, B. F.; Weglicki, W. B. Identification of Free-Radicals in Myocardial-Ischemia Reperfusion by Spin Trapping with Nitrone Dmpo FEBS Lett. 1987, 221 (1) 101-104
35. Roubaud, V.; Sankarapandi, S.; Kuppusamy, P.; Tordo, P.; Zweier, J. L. Quantitative measurement of superoxide generation using the spin trap 5-(diethoxyphosphoryl)-5-methyl-1-pyrroline-N-oxide Anal. Biochem. 1997, 247 (2) 404-411 (Pubitemid 27200178)
36. Dikalov, S. I.; Dikalova, A. E.; Mason, R. P. Noninvasive diagnostic tool for inflammation-induced oxidative stress using electron spin resonance spectroscopy and an extracellular cyclic hydroxylamine Arch. Biochem. Biophys. 2002, 402 (2) 218-226 (Pubitemid 34848639)
37. Bacic, G.; Spasojevic, I.; Secerov, B.; Mojovic, M. Spin-trapping of oxygen free radicals in chemical and biological systems: New traps, radicals and possibilities Spectrochim. Acta, Part a: Mol. Biomol. Spectrosc. 2008, 69 (5) 1354-1366
38. Valentine, J. S.; Foote, C. S.; Grenbery, A.; Liebman, J. F. E. Active oxygen in biochemistry; Academic Press: 1995; Vol. 3.
39. Dvoranova, D.; Brezova, V.; Mazur, M.; Malati, M. A. Investigations of metal-doped titanium dioxide photocatalysts Appl. Catal., B 2002, 37 (2) 91-105 (Pubitemid 34220290)
40. Noda, H.; Oikawa, K.; Ohya-Nishigughi, H.; Kamada, H. Detection of superoxide ions from photoexcited semiconductors in non-aqueous solvents using ESR spin-trapping technique Bull. Chem. Soc. Jpn. 1993, 66 (12) 3542-3547 (Pubitemid 24078269)
41. Baird, W. R.; Foley, R. T. Solubility of Oxygen in Selected Organic Solvents. J. Chem. Eng. Data 1972, 17 (3), 355 -&.
42. Greenwald, R. A. Handbook of Method for oxygen radical research; CRC Press: Boca Raton, FL, 1985; p 65.
43. Lee, M. L.; Markides, K. E. Analytical Supercritical Fluid Chromatography and Extraction; Chromatography Conferences Inc.: Provo, UT, 1990.
44. Zang, L.-Y.; Stone, K.; Pryor, W. A. Detection of free radicals in aqueous extracts of cigarette tar by electron spin resonance Free Radicals Biol. Med. 1995, 19 (2) 161-167
45. Pryor, W. A.; Stone, K.; Zang, L.-Y.; Bermudez, E. Fractionation of aqueous cigarette tar extracts: Fractions that contain the tar radicals cause DNA damage Chem. Res. Toxicol. 1998, 11 (5) 441-448 (Pubitemid 28242488)
46. Squadrito, G. L.; Cueto, R.; Dellinger, B.; Pryor, W. A. Quinoid redox cycling as a mechanism for sustained free radical generation by inhaled airborne particulate matter Free Radical Biol. Med. 2001, 31 (9) 1132-1138 (Pubitemid 33009320)
47. Dellinger, B.; Pryor, W. A.; Cueto, R.; Squadrito, G. L.; Hedge, V.; Deutsch, W. A. Role of free radicals in the toxicity of airborne fine particulate matter Chem. Res. Toxicol. 2001, 14, 1371-1377 (Pubitemid 32988407)
48. Dellinger, B.; Lomnicki, S.; Khachatryan, L. Formation and stabilization of persistent free radicals Proc. Combust. Inst. 2007, 31, 521-528 (Pubitemid 47424424)
49. Lomnicki, S.; Truong, H.; Vejerano, E.; Dellinger, B. Copper oxide-based model of persistent free radical formation on combustion-derived particulate matter Environ. Sci. Technol. 2008, 42 (13) 4982-498
50. Fahmy, B.; Ding, L.; You, D.; Lomnicki, S.; Dellinger, B.; Cormier, S. A. In vitro and in vivo assessment of pulmonary risk associated with exposure to combustion generated fine particles Environ. Toxicol. Pharmacol. 2010, 29, 173-182
51. Balakrishna, S.; Lomnicki, S.; McAvey, K. M.; Cole, R. B.; Dellinger, B.; Cormier, S. A. Environmentally persistent free radicals amplify ultrafine particle mediated cellular oxidative stress and cytotoxicity Part. Fibre Toxicol. 2009, 6, 11
52. Balakrishna, S.; Lomnicki, S.; Dellinger, B.; Cormier, S. A. Resveratrol Ameliorates the Redox Imbalances in Human Airway Epithelial Cells Exposed to Combustion Generated Nanoparticles Free Radical Biol. Med. 2008, 45, S44-S
53. Masarwa, M.; Cohen, H.; Meyerstein, D.; Hickman, D. L.; Bakac, A.; Espenson, J. H. Reactions of Low-Valent Transition-Metal Complexes with Hydrogen-Peroxide-Are They Fenton-Like or Not 0.1The Case of Cu+Aq and Cr-2+Aq J. Am. Chem. Soc. 1988, 110 (13) 4293-4297