Unprecedented hydroxyl radical-dependent two-step chemiluminescence production by polyhalogenated quinoid carcinogens and H2O2

Proceedings of the National Academy of Sciences of the United States of America

Volumn 109, Issue 40, 2012, Pages 16046-16051

  Zhu, Ben Zhan ^a,b   Mao, Li ^a   Huang, Chun Hua ^a   Qin, Hao ^a   Fan, Rui Mei ^a   Kalyanaraman, Balaraman ^c   Zhu, Jun Ge ^a  

^a RESEARCH CENTER FOR ECO ENVIRONMENTAL SCIENCES   (China)

^b OREGON STATE UNIVERSITY   (United States)

^c MEDICAL COLLEGE OF WISCONSIN   (United States)

Author keywords

Dichloromaleic acid; Halogenated phenols; Halogenated quinones; Light emission; Trichlorohydroxy 1,4 benzoquinone

Indexed keywords

CHLORANIL; HYDROGEN PEROXIDE; HYDROXYL RADICAL;

ARTICLE; CHEMOLUMINESCENCE; CONCENTRATION (PARAMETERS); CORRELATION ANALYSIS; DECHLORINATION; HALOGENATION; HYDROXYLATION; PH; PRIORITY JOURNAL;

CARCINOGENS; CHLORANIL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CHROMATOGRAPHY, ION EXCHANGE; FLUORESCENCE; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HYDROGEN PEROXIDE; HYDROXYL RADICAL; LUMINESCENCE; MODELS, CHEMICAL; MOLECULAR STRUCTURE;

EID: 84867036556     PISSN: 00278424     EISSN: 10916490     Source Type: Journal    
DOI: 10.1073/pnas.1204479109     Document Type: Article

References (31)

1. Bolton JL, Trush MA, Penning TM, Dryhurst G, Monks TJ (2000) Role of quinones in toxicology. Chem Res Toxicol 13:135-160. (Pubitemid 30169958)
2. Song Y, Wagner BA, Witmer JR, Lehmler HJ, Buettner GR (2009) Nonenzymatic displacement of chlorine and formation of free radicals upon the reaction of glutathione with PCB quinones. Proc Natl Acad Sci USA 106:9725-9730.
3. Zhu BZ, Shan GQ (2009) Potential mechanism for pentachlorophenol-induced carcinogenicity: A novel mechanism for metal-independent production of hydroxyl radicals. Chem Res Toxicol 22:969-977.
4. Meunier B (2002) Catalytic degradation of chlorinated phenols. Science 296:270-271.
5. Gupta SS, et al. (2002) Rapid total destruction of chlorophenols by activated hydrogen peroxide. Science 296:326-328.
6. Sorokin A, Seris JL, Meunier B (1995) Efficient oxidative dechlorination and aromatic ring-cleavage of chlorinated phenols catalyzed by iron sulfophthalocyanine. Science 268:1163-1166.
7. Zhao YL, Qin F, Boyd JM, Anichina J, Li XF (2010) Characterization and determination of chloro- and bromo-benzoquinones as new chlorination disinfection byproducts in drinking water. Anal Chem 82:4599-4605.
8. Halliwell B, Gutteridge JMC (2007) Free Radicals in Biology and Medicine (Oxford University Press, Oxford) p 45.
9. Wagner JR, Cadet J (2010) Oxidation reactions of cytosine DNA components by hydroxyl radical and one-electron oxidants in aerated aqueous solutions. Acc Chem Res 43:564-571.
10. Xu G, Chance MR (2007) Hydroxyl radical-mediated modification of proteins as probes for structural proteomics. Chem Rev 107:3514-3543. (Pubitemid 47333548)
11. Voinov MA, Pagan JOS, Morrison E, Smirnova TI, Smirnov AI (2011) Surface-mediated production of hydroxyl radicals as a mechanism of iron oxide nanoparticle biotoxicity. J Am Chem Soc 133:35-41.
12. Montzka SA, et al. (2011) Small interannual variability of global atmospheric hydroxyl. Science 331:67-69.
13. Rohrer F, Berresheim H (2006) Strong correlation between levels of tropospheric hydroxyl radicals and solar ultraviolet radiation. Nature 442:184-187. (Pubitemid 44086562)
14. Zhu BZ, Zhao HT, Kalyanaraman B, Frei B (2002) Metal-independent production of hydroxyl radicals by halogenated quinones and hydrogen peroxide: An ESR spin trapping study. Free Radical Biol Med 32:465-473. (Pubitemid 34178355)
15. Zhu BZ, Kalyanaraman B, Jiang GB (2007) Molecular mechanism for metal-independent production of hydroxyl radicals by hydrogen peroxide and halogenated quinones. Proc Natl Acad Sci USA 104:17575-17578. (Pubitemid 350210876)
16. Zhu BZ, et al. (2007) Mechanism of metal-independent decomposition of organic hydroperoxides and formation of alkoxyl radicals by halogenated quinones. Proc Natl Acad Sci USA 104:3698-3702.
17. Zhu BZ, Shan GQ, Huang CH, Kalyanaraman B, Mao L, Du YG (2009) Metal-independent decomposition of hydroperoxides by halogenated quinones: Detection and identification of a quinone ketoxy radical. Proc Natl Acad Sci USA 106:11466-11471.
18. Zhu BZ, Zhu JG, Mao L, Kalyanaraman B, Shan GQ (2010) Detoxifying carcinogenic polyhalogenated quinones by hydroxamic acids via an unusual double Lossen rearrangement mechanism. Proc Natl Acad Sci USA 107:20686-20690.
19. Kanakubo A, IsobeM(2005) Isolation of brominated quinones showing chemiluminescence activity from luminous acorn worm, Ptychodera flava. Bioorg Med Chem 13:2741-2747. (Pubitemid 40387484)
20. Stevani CV, Silva SM, Badder WJ (2000) Studies on the mechanism of the excitation step in peroxyoxalate chemiluminescence. Eur J Org Chem 24:4037-4046. (Pubitemid 32047880)
21. Schuster GB (1979) Chemiluminescence of organic peroxides. Conversion of ground-state reactants to excited-state products by the chemically initiated electron-exchange luminescence mechanism. Acc Chem Res 12:366-373.
22. Matsumoto M (2004) Advanced chemistry of dioxetane-based chemiluminescent substrates originating from bioluminescence. J Photochem Photobiol C 5:27-53.
23. Adam W, Kazakov DV, Kazakov VP (2005) Singlet-oxygen chemiluminescence in peroxide reactions. Chem Rev 105:3371-3387. (Pubitemid 41435035)
24. Bos R, et al. (2009) In search of a chemiluminescence 1,4-dioxy biradical. J AmChem Soc 131:2770-2771.
25. Saleh L, Plieth C (2010) Total low-molecular-weight antioxidants as a summary parameter, quantified in biological samples by a chemiluminescence inhibition assay. Nat Protoc 5:1627-1634.
26. Widder EA (2010) Bioluminescence in the ocean: Origins of biological, chemical, and ecological diversity. Science 328:704-708.
27. Chignell CF, et al. (2008) EPR studies of in vivo radical production by 3,3′,5,5′-tetrabromobisphenol A (TBBPA) in the Sprague-Dawley rat. Toxicol Appl Pharmacol 230:17-22.
28. Teuten EL, Us L, Reddy CM (2005) Two abundant bioaccumulated halogenated compounds are natural products. Science 307:917-920. (Pubitemid 40229226)
29. Kelly BC, Ikonomou MG, Blair JD, Morin AE, Gobas FAPC (2007) Food web-specific biomagnification of persistent organic pollutants. Science 317:236-239. (Pubitemid 47076197)
30. Pera-Titus M, García-Molina V, Baños MA, Giménez J, Esplugas S (2004) Degradation of chlorophenols by means of advanced oxidation processes: A general review. Appl Catal B 47:219-256. (Pubitemid 38215192)
31. Zimbron JA, Reardon KF (2009) Fenton's oxidation of pentachlorophenol. Water Res 43:1831-1840.