Chemiluminescence emission during reactions between superoxide and selected aliphatic and aromatic halocarbons in aprotic media

Journal of Bioluminescence and Chemiluminescence

Volumn 11, Issue 1, 1996, Pages 9-22

  Shoaf, Antony R ^a  

^a WAKE FOREST SCHOOL OF MEDICINE   (United States)

Author keywords

1o2*; Chemiluminescence; CL; Differential pulse polarography; DPP; Organic halocarbons; Peroxidative tissue damage; Reductive dehalogenation; RX; Singlet oxygen; Superoxide; O2

Indexed keywords

2,3,7,8 TETRACHLORODIBENZO PARA DIOXIN; CARBON TETRACHLORIDE; CHLOROFORM; DECACHLOROBIPHENYL; DIMETHYL SULFOXIDE; NITROBLUE TETRAZOLIUM; OXYGEN; POLYCHLORINATED BIPHENYL; SINGLET OXYGEN; SUPEROXIDE;

ANIMAL; ARTICLE; CHEMISTRY; CHEMOLUMINESCENCE; COMPARATIVE STUDY; KINETICS; LIPID PEROXIDATION; METHODOLOGY; PLANT; POLAROGRAPHY;

ANIMALS; CARBON TETRACHLORIDE; CHEMILUMINESCENT MEASUREMENTS; CHLOROFORM; DIMETHYL SULFOXIDE; KINETICS; LIPID PEROXIDATION; NITROBLUE TETRAZOLIUM; OXYGEN; PLANTS; POLAROGRAPHY; POLYCHLORINATED BIPHENYLS; SINGLET OXYGEN; SUPEROXIDES; TETRACHLORODIBENZODIOXIN;

EID: 0029693825     PISSN: 08843996     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-1271(199601)11:1<9::AID-BIO396>3.0.CO;2-N     Document Type: Article

References (53)

1. Recknagel RO. Carbon tetrachloride hepatotoxicity. Pharmacol Rev 1967;19:145-208.
2. Reynolds ES. Liver parenchymal cell injury. IV. Pattern of incorporation of carbon and chlorine from carbontetrachloride into chemical constituents in liver in vivo. J Pharmacol Exp Ther 1967;155:117-26.
3. Recknagel RO, Ghoshal AK. Lipoperoxidation of rat liver microsomal lipids induced by carbon tetrachloride. Nature (London) 1966;210:1162-3.
4. Slater TF. Free radical mechanisms in tissue injury. London: Pion, 1972:85-166.
5. Gregory NL. Carbon tetrachloride toxicity and electron capture. Nature (London) 1966;212:1460-1.
6. Slater TF. Necrogenic action of carbontetrachloride in the rat: a speculative mechanism based on activation. Nature (London) 1966;209:36-40.
7. George P, Griffith JS. Electron transfer and enzyme catalysis. In: Boyer PD, Lardy H, Myrback K editors. The enzymes. 2nd ed. vol. 1, New York: Academic Press 1959:347.
8. 1-DDT in aprotic media. J Am Chem Soc 1981;103:713-4.
9. Gareil M, Pinson J, Saveant JM. Nucleophilic substitution of aromatic halides by electrogenerated superoxide ions. Nouv J Chemie 1981;5:311-8.
10. Recknagel RO, Glende Jr EA, Hruszkewycz AM. In: Pryor WA, editor. Free radicals in biology, vol. III. New York: Academic Press, 1977:
11. Aust SO, Roerig DL, Pederson TC. Evidence for superoxide generation by NADPH-cytochrome C reductase of rate liver microsomes. Biochem Biophys Res Commun 1972;47: 1133-7.
12. Strobel HW, Coon MJ. Effect of superoxide generation and dismutation on hydroxylation reactions catalyzed by liver microsomal cytrochrome p450. J Biol Chem 1971;246:7826-9.
13. 4 hepatotoxicity. Toxicol Appl Pharmacol 1972;23: 789-91.
14. DiLuzio NR, Stege TE. Enhanced hepatic chemiluminescence following carbontetrachloride or hydrazine administration. Life Sci 1977; 21:1457-64.
15. Smith MR, Thor H, Hartzell P, Orrenius S. The measurement of lipid peroxidation in isolated hepatocytes. Biochem Pharmacol 1982; 31:19-26.
16. -) in aprotic media. Toxicologist 1985;5:213 (abstr #852).
17. Adam, RN. Electrochemistry at solid electrodes. New York, Marcel Dekker 1969:50.
18. Kasha M. Transmission filters in the ultraviolet. J Opt Soc Amer 1948;38:292-34.
19. g) dimol chemiluminescence. Photochem Photobiol 1977;25:299-304.
20. -) from whole mammalian liver. J Biolumin Chemilumin 1991;6:87-96.
21. Khan AU. Singlet molecular oxygen from superoxide anion and sensitized fluorescence of organic molecules. Science 1970;168:476-7.
22. Sander U, Stauff J. Excited states of oxygen dimers in the reaction of superoxide-anion radicals with water. Anales Asoc Quim Argentina 1971;59:149-55.
23. Abbott SR, Ness S, Hercules DM. Chemiluminescence from peroxide decomposition reactions. The role of energy transfer. J Am Chem Soc 1970;92:1128-36.
24. Duran N. Singlet oxygen in biological processes. In: Adam W, Cilento G, editors. Chemical and biological generation of excited states. New York: Academic Press, 1982:345-69.
25. Mishin V, Pokravskii A, Lyakhovice VV. Interactions of various acceptors with anion radicals of oxygen in liver microsomes. Biokhimiya 1976;41:763-7.
26. Beauchamp C, Fridovich C. Superoxide dismutase: improved assays and an assay applicable to acrylamide gels. Anal Biolchem 1971;44:276-87.
27. Sawyer DT, Roberts Jr JL. Electrochemistry of oxygen and superoxide ion in dimethylsulfoxide at platinum, gold and mercury electrodes. J Electroanal Chem 1966;12:90-101.
28. g) in the reaction of potassium superoxide with water. J Am Chem Soc 1981;103:6516-7.
29. Corey EJ, Mehrotra MM, Khan AU. Water induced dismutation of superoxide anion generates singlet molecular oxygen. Biochem Biophys Res Commun 1987;145:842-6.
30. Kanofsky JR. Singlet oxygen production in superoxide ion-halocarbon systems. J Am Chem Soc 1986;108:2977-9.
31. Kasha M, Khan AU. The physics, chemistry, and biology of singlet molecular oxygen. Ann NY Acad Sci 1970;171:5-23.
32. Poland A, Knutson JC. 2,3,7,8-Tetrachlorodibenzo-p-dioxin and related halogenated aromatic hydrocarbons: examination of the mechanism of toxicity. Annu Rev Pharmacol Toxicol 1982;22:517-54.
33. Estabrook RW, Werringloer J. The oxygen sensing characteristics of microsomal enzymes. Adv Exp Med Biol 1977;78:19-35.
34. Bartoli GM, Galeotti T, Palombini G, Parisi G, Azzi A. Different contribution of rat liver microsomal pigments in the formation of superoxide anions and hydrogen peroxide during development. Arch Biochem Biophys 1977;184:276-81.
35. Forman HJ, Boveris A. Superoxide radical and hydrogen peroxide in mitochondria. Free Radie Biol 1982;5:65-90.
36. Ugazio G. Halogenoalkanes and liver injury. In: Slater TF, editor. Biochemical mechanisms of liver injury. London: Academic Press, 1978:709-43.
37. Rawls HR, Van Santen PJ. Singlet oxygen and the initiation of fatty acid autoxidation. Tetrahedron Lett 1968;1675-8.
38. 4-treated rats. Biochem Pharmacol 1982;31:609-14.
39. Pohl LR, Mico BA. Electrophilic halogens as potentially toxic metabolites of halogenated compounds. TIPS, 1984;February:61-4.
40. Valentine JS. The chemical reactivity of superoxide anion in aprotic versus protic media: a review. In: Caughey WS, editor. Biochemical and clinical aspects of oxygen. New York: Academic Press, 1979:659-77.
41. Smith JR WF. Kinetic evidence for both quenching and reaction of singlet oxygen with triethylamine in pyridine solution. J Am Chem Soc 1972;94:186-90.
42. Farmilo A, Wilkinson F. On the mechanism of quenching of singlet oxygen in solution. Photochem Photobiol 1973;18:447-50.
43. Foote CS. In: Wasserman HH and Murray RW, editors. Singlet oxygen. New York: Academic Press, 1978:139-71.
44. Foote CS, Fujimoto TT, Chang YC. Chemistry of singlet oxygen. XV. Irrelevance of azide trapping to mechanism of the ene reaction. Tetrahedron Lett 1972;45-8.
45. Foote CS, Ching T-Y. Chemistry of singlet oxygen. XXI. Kinetics of bilirubin photooxygenation. J Am Chem Soc 1975;97:6209-14.
46. Matheson IBC, Etheridge RD, Kratowich NR, Lee J. The quenching of singlet oxygen by amino acids and proteins. Photochem Photobiol 1975;21:165-71.
47. Wu KC, Trozzolo AM. Evidence for the production of singlet molecular-oxygen from the quenching of excited states of dialkyl ketones by molecular oxygen. J Photochem 1979;10: 407-10.
48. Lamola AA. Production of pyrimidine dimers in DNA in the dark. Biochem Biophys Res Commun 1971;43:893-8.
49. Suwa K, Kimura T, Schaap AP. Reactivity of singlet molecular oxygen with cholesterol in a phospholipid membrane matrix. A model for oxidative damage of membranes. Biochem Biophys Res Commun 1977;75:785-92.
50. 2 and/or HOOH adduct derived from the riboflavin-copper(I) chelate. Biochemistry 1970;9:4343-51.
51. Stauff J, Ostrowske J. Chemiluminescence von mitochondria. Z Naturforschung 1967;22b: 734-40.
52. Vasil'ev RF. Spin-orbit coupling and intermolecular energy transfer. Nature, 1963; 200:773-4.
53. Allen RC. Biochemiexcitation. Chemiluminescence and the study of biological oxygenation reactions. In: Adam W, Cilento G, editors. Chemical and biological generation of excited states. New York: Academic Press, 1982:309-44.