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Volumn 23, Issue 5, 2010, Pages 880-887

Investigating the mechanisms of aromatic amine-induced protein free radical formation by quantitative structure-activity relationships: Implications for drug-induced agranulocytosis

Author keywords

[No Author keywords available]

Indexed keywords

2 CHLOROANILINE; 2 NITROANILINE; 2,4 DICHLOROANILINE; 2,4 DIMETHOXYANILINE; 2,4 DIMETHYLANILINE; 2,6 DICHLOROANILINE; 2,6 DIMETHYLANILINE; 3 CHLOROANILINE; 3 NITROANILINE; 3,4 DICHLOROANILINE; 3,4 DIMETHYLANILINE; 4 AMINOBENZONITRILE; 4 AMINOVERATROLE; 4 CHLORO ORTHO TOLUIDINE; 4 FLUOROANILINE; 5,5 DIMETHYL 1 PYRROLINE 1 OXIDE; AMINOGLUTETHIMIDE; AMINOSALICYLIC ACID; ANILINE; ANILINE DERIVATIVE; ANISIDINE; BENZONITRILE; ETHYLANILINE; FREE RADICAL; HYDROGEN PEROXIDE; MYELOPEROXIDASE; PROCAINAMIDE; PROTEIN DERIVATIVE; TOLUIDINE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

EID: 77952398669     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx900432d     Document Type: Article
Times cited : (13)

References (36)
  • 1
    • 34547621062 scopus 로고    scopus 로고
    • Aminoglutethimide-induced protein free radical formation on myeloperoxidase: A potential mechanism of agranulocytosis
    • Siraki, A. G., Bonini, M. G., Jiang, J., Ehrenshaft, M., and Mason, R. P. (2007) Aminoglutethimide-induced protein free radical formation on myeloperoxidase: a potential mechanism of agranulocytosis Chem. Res. Toxicol. 20, 1038-1045
    • (2007) Chem. Res. Toxicol. , vol.20 , pp. 1038-1045
    • Siraki, A.G.1    Bonini, M.G.2    Jiang, J.3    Ehrenshaft, M.4    Mason, R.P.5
  • 2
    • 47549089691 scopus 로고    scopus 로고
    • Procainamide, but not N-acetylprocainamide, induces protein free radical formation on myeloperoxidase: A potential mechanism of agranulocytosis
    • Siraki, A. G., Deterding, L. J., Bonini, M. G., Jiang, J., Ehrenshaft, M., Tomer, K. B., and Mason, R. P. (2008) Procainamide, but not N-acetylprocainamide, induces protein free radical formation on myeloperoxidase: a potential mechanism of agranulocytosis Chem. Res. Toxicol. 21, 1143-1153
    • (2008) Chem. Res. Toxicol. , vol.21 , pp. 1143-1153
    • Siraki, A.G.1    Deterding, L.J.2    Bonini, M.G.3    Jiang, J.4    Ehrenshaft, M.5    Tomer, K.B.6    Mason, R.P.7
  • 3
    • 0024399182 scopus 로고
    • Idiosyncratic drug reactions: Possible role of reactive metabolites generated by leukocytes
    • Uetrecht, J. P. (1989) Idiosyncratic drug reactions: Possible role of reactive metabolites generated by leukocytes Pharm. Res. 6, 265-273
    • (1989) Pharm. Res. , vol.6 , pp. 265-273
    • Uetrecht, J.P.1
  • 4
    • 0024523935 scopus 로고
    • Drug-protein conjugates-XVIII. Detection of antibodies towards the antimalarial amodiaquine and its quinone imine metabolite in man and the rat
    • Christie, G., Breckenridge, A. M., and Park, B. K. (1989) Drug-protein conjugates-XVIII. Detection of antibodies towards the antimalarial amodiaquine and its quinone imine metabolite in man and the rat Biochem. Pharmacol. 38, 1451-1458
    • (1989) Biochem. Pharmacol. , vol.38 , pp. 1451-1458
    • Christie, G.1    Breckenridge, A.M.2    Park, B.K.3
  • 5
    • 0018567227 scopus 로고
    • Antibodies to nuclear antigens in patients treated with procainamide or acetylprocainamide
    • Lahita, R., Kluger, J., Drayer, D. E., Koffler, D., and Reidenberg, M. M. (1979) Antibodies to nuclear antigens in patients treated with procainamide or acetylprocainamide N. Engl. J. Med. 301, 1382-1385
    • (1979) N. Engl. J. Med. , vol.301 , pp. 1382-1385
    • Lahita, R.1    Kluger, J.2    Drayer, D.E.3    Koffler, D.4    Reidenberg, M.M.5
  • 6
    • 0021051368 scopus 로고
    • Aromatic amines and the pathogenesis of lupus erythematosus
    • Reidenberg, M. M. (1983) Aromatic amines and the pathogenesis of lupus erythematosus Am. J. Med. 75, 1037-1042
    • (1983) Am. J. Med. , vol.75 , pp. 1037-1042
    • Reidenberg, M.M.1
  • 7
    • 0025746640 scopus 로고
    • Possible role of free radical formation in clozapine (clozaril)-induced agranulocytosis
    • Fischer, V., Haar, J. A., Greiner, L., Lloyd, R. V., and Mason, R. P. (1991) Possible role of free radical formation in clozapine (clozaril)-induced agranulocytosis Mol. Pharmacol. 40, 846-853
    • (1991) Mol. Pharmacol. , vol.40 , pp. 846-853
    • Fischer, V.1    Haar, J.A.2    Greiner, L.3    Lloyd, R.V.4    Mason, R.P.5
  • 9
    • 0026645711 scopus 로고
    • The role of leukocyte-generated reactive metabolites in the pathogenesis of idiosyncratic drug reactions
    • Uetrecht, J. P. (1992) The role of leukocyte-generated reactive metabolites in the pathogenesis of idiosyncratic drug reactions Drug Metab. Rev. 24, 299-366
    • (1992) Drug Metab. Rev. , vol.24 , pp. 299-366
    • Uetrecht, J.P.1
  • 10
    • 61349202964 scopus 로고    scopus 로고
    • Preservation of basophils in dapsone-induced agranulocytosis suggests a possible pathogenetic role for leucocyte peroxidases
    • Besser, M., Vera, J., Clark, J., Chitnavis, D., Beatty, C., and Vassiliou, G. (2009) Preservation of basophils in dapsone-induced agranulocytosis suggests a possible pathogenetic role for leucocyte peroxidases Int. J. Lab. Hematol. 31, 245-247
    • (2009) Int. J. Lab. Hematol. , vol.31 , pp. 245-247
    • Besser, M.1    Vera, J.2    Clark, J.3    Chitnavis, D.4    Beatty, C.5    Vassiliou, G.6
  • 11
    • 0033567245 scopus 로고    scopus 로고
    • Oxidation of clozapine and ascorbate by myeloperoxidase
    • Hsuanyu, Y. and Dunford, H. B. (1999) Oxidation of Clozapine and Ascorbate by Myeloperoxidase Arch. Biochem. Biophys. 368, 413-420
    • (1999) Arch. Biochem. Biophys. , vol.368 , pp. 413-420
    • Hsuanyu, Y.1    Dunford, H.B.2
  • 12
    • 41049100518 scopus 로고
    • A spectrophotometric method for measuring the breakdown of hydrogen peroxide by catalase
    • Beers, R. F., Jr. and and Sizer, I. W. (1952) A spectrophotometric method for measuring the breakdown of hydrogen peroxide by catalase J. Biol. Chem. 195, 133-140
    • (1952) J. Biol. Chem. , vol.195 , pp. 133-140
    • Beers Jr., R.F.1    Sizer, I.W.2
  • 13
    • 0000224832 scopus 로고
    • Spin trapping of some short-lived radicals by the nitroxide method
    • Lagercrantz, C. (1971) Spin trapping of some short-lived radicals by the nitroxide method J. Phys. Chem. 75, 3466-3475
    • (1971) J. Phys. Chem. , vol.75 , pp. 3466-3475
    • Lagercrantz, C.1
  • 16
    • 0842338693 scopus 로고    scopus 로고
    • Thermodynamics of Chlorinated Phenols, Polychlorinated Dibenzo- p -Dioxins, Polychlorinated Dibenzofurans, Derived Radicals, and Intermediate Species
    • Burcat, A., Khachatryan, L., and Dellinger, B. L. (2003) Thermodynamics of Chlorinated Phenols, Polychlorinated Dibenzo- p -Dioxins, Polychlorinated Dibenzofurans, Derived Radicals, and Intermediate Species J. Phys. Chem. Ref. Data 32, 443-517
    • (2003) J. Phys. Chem. Ref. Data , vol.32 , pp. 443-517
    • Burcat, A.1    Khachatryan, L.2    Dellinger, B.L.3
  • 20
    • 0017129482 scopus 로고
    • Substituent effect on the oxidation of phenols and aromatic amines by horseradish peroxidase compound i
    • Job, D. and Dunford, H. B. (1976) Substituent effect on the oxidation of phenols and aromatic amines by horseradish peroxidase compound I Eur. J. Biochem. 66, 607-614
    • (1976) Eur. J. Biochem. , vol.66 , pp. 607-614
    • Job, D.1    Dunford, H.B.2
  • 21
    • 0024801405 scopus 로고
    • Drug metabolism by leukocytes and its role in drug-induced lupus and other idiosyncratic drug reactions
    • Uetrecht, J. (1989) Drug metabolism by leukocytes and its role in drug-induced lupus and other idiosyncratic drug reactions Crit. Rev. Toxicol. 20, 213-235
    • (1989) Crit. Rev. Toxicol. , vol.20 , pp. 213-235
    • Uetrecht, J.1
  • 23
    • 0343796932 scopus 로고
    • Nitroxides. IX. Electron paramagnetic resonance of parasubstituted tert-butylphenylnitroxide
    • Lemaire, H., Marechal, Y., Ramasseul, R., and Rassat, A. (1965) Nitroxides. IX. Electron paramagnetic resonance of parasubstituted tert-butylphenylnitroxide Bull. Soc. Chim. Fr. 2, 372-378
    • (1965) Bull. Soc. Chim. Fr. , vol.2 , pp. 372-378
    • Lemaire, H.1    Marechal, Y.2    Ramasseul, R.3    Rassat, A.4
  • 24
    • 0346342712 scopus 로고
    • Nitroxides. XXXIV. Substituted tert-butyl phenyl nitroxide derivatives electron paramagnetic resonance. Ultrafine deviations due to nitrogen
    • Barbarella, G. and Rassat, A. (1969) Nitroxides. XXXIV. Substituted tert-butyl phenyl nitroxide derivatives electron paramagnetic resonance. Ultrafine deviations due to nitrogen Bull. Soc. Chim. Fr. 7, 2378-2385
    • (1969) Bull. Soc. Chim. Fr. , vol.7 , pp. 2378-2385
    • Barbarella, G.1    Rassat, A.2
  • 25
    • 37049134150 scopus 로고
    • Stability of aryl-tert-butylnitroxides
    • Calder, A. and Forrester, A. R. (1967) Stability of aryl-tert- butylnitroxides Chem. Commun. (Camb) 14, 682-684
    • (1967) Chem. Commun. (Camb) , vol.14 , pp. 682-684
    • Calder, A.1    Forrester, A.R.2
  • 26
    • 0344532783 scopus 로고
    • Nitroxide radicals 0.7. Nuclear and electron resonance spectra of some aromatic tert-butyl nitroxides
    • Calder, A., Forrester, A. R., Emsley, J. W., Luckhurst, G. R., and Storey, R. A. (1970) Nitroxide radicals 0.7. Nuclear and electron resonance spectra of some aromatic tert-butyl nitroxides Mol. Phys. 18, 481-489
    • (1970) Mol. Phys. , vol.18 , pp. 481-489
    • Calder, A.1    Forrester, A.R.2    Emsley, J.W.3    Luckhurst, G.R.4    Storey, R.A.5
  • 27
    • 37049121654 scopus 로고
    • Nitroxide radicals. VIII. Stability of ortho-alkyl-substituted phenyl tert-butyl nitroxides
    • Forrester, A. R. and Hepburn, S. P. (1970) Nitroxide radicals. VIII. Stability of ortho-alkyl-substituted phenyl tert-butyl nitroxides J. Chem. Soc. C 9, 1277-1280
    • (1970) J. Chem. Soc. C , vol.9 , pp. 1277-1280
    • Forrester, A.R.1    Hepburn, S.P.2
  • 28
    • 2142759063 scopus 로고
    • Electron spin resonance and nuclear magnetic resonance spectra of sterically hindered aromatic nitroxide radicals - Synthesis of stable nitroxide radicals
    • Pedersen, J. A. and Torssell, K. (1971) Electron spin resonance and nuclear magnetic resonance spectra of sterically hindered aromatic nitroxide radicals-synthesis of stable nitroxide radicals Acta Chem. Scand. 25, 3151-3162
    • (1971) Acta Chem. Scand. , vol.25 , pp. 3151-3162
    • Pedersen, J.A.1    Torssell, K.2
  • 29
    • 0001635821 scopus 로고
    • Investigation of radical intermediates in organic reactions by use of nitroso compounds as scavengers the nitroxide method
    • Torssell, K. (1970) Investigation of radical intermediates in organic reactions by use of nitroso compounds as scavengers the nitroxide method Tetrahedron 26, 2759-2773
    • (1970) Tetrahedron , vol.26 , pp. 2759-2773
    • Torssell, K.1
  • 33
    • 37049127499 scopus 로고
    • Nitroxide radicals. XII. Decomposition of o-, m-, and p-halophenyl tert-butyl nitroxides
    • Organic and Bio-Organic Chemistry
    • Calder, A., Forrester, A. R., and Hepburn, S. P. (1973) Nitroxide radicals. XII. Decomposition of o-, m-, and p-halophenyl tert-butyl nitroxides J. Chem. Soc., Perkin Trans. 1: Organic and Bio-Organic Chemistry 5 456-465
    • (1973) J. Chem. Soc., Perkin Trans. 1 , vol.5 , pp. 456-465
    • Calder, A.1    Forrester, A.R.2    Hepburn, S.P.3
  • 34
    • 37049126466 scopus 로고
    • Nitroxide radicals. IV. Oxidation of cyclic N-hydroxyimides
    • Calder, A., Forrester, A. R., and Thomson, R. H. (1969) Nitroxide radicals. IV. Oxidation of cyclic N-hydroxyimides J. Chem. Soc. C 3, 512-516
    • (1969) J. Chem. Soc. C , vol.3 , pp. 512-516
    • Calder, A.1    Forrester, A.R.2    Thomson, R.H.3
  • 35
    • 37049118262 scopus 로고
    • Nitroxide radicals. XVI. Unpaired electron distribution in para substituted aryl tert -butyl nitroxides and 2-naphthyl phenyl nitroxides
    • Forrester, A. R., Hepburn, S. P., and McConnachie, G. (1974) Nitroxide radicals. XVI. Unpaired electron distribution in para substituted aryl tert -butyl nitroxides and 2-naphthyl phenyl nitroxides J. Chem. Soc., Perkin Trans. 1: Org. Bio-Org. Chem. 19, 2213-2219
    • (1974) J. Chem. Soc., Perkin Trans. 1: Org. Bio-Org. Chem. , vol.19 , pp. 2213-2219
    • Forrester, A.R.1    Hepburn, S.P.2    McConnachie, G.3


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