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Volumn 29, Issue 3, 2016, Pages 255-269

Methemoglobin Formation and Characterization of Hemoglobin Adducts of Carcinogenic Aromatic Amines and Heterocyclic Aromatic Amines

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 1 METHYL 6 PHENYLIMIDAZO[4,5 B]PYRIDINE; 4 BIPHENYLAMINE; ANILINE; AROMATIC AMINE; CARCINOGENIC AROMATIC AMINE; CHYMOTRYPSIN; GLU C PROTEIN; HEMOGLOBIN; HETEROCYCLIC AROMATIC AMINE; INDOLE; LYS C PROTEIN; METHEMOGLOBIN; PROTEIN; SULFINAMIDE; SULFONAMIDE; THIOL DERIVATIVE; TRYPSIN; UNCLASSIFIED DRUG; AMINE; AROMATIC HYDROCARBON; CARCINOGEN; HETEROCYCLIC COMPOUND;

EID: 84961710627     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/acs.chemrestox.5b00418     Document Type: Article
Times cited : (42)

References (88)
  • 1
    • 1942504286 scopus 로고    scopus 로고
    • Heterocyclic amines: Mutagens/carcinogens produced during cooking of meat and fish
    • Sugimura, T., Wakabayashi, K., Nakagama, H., and Nagao, M. (2004) Heterocyclic amines: Mutagens/carcinogens produced during cooking of meat and fish Cancer Sci. 95, 290-299 10.1111/j.1349-7006.2004.tb03205.x
    • (2004) Cancer Sci. , vol.95 , pp. 290-299
    • Sugimura, T.1    Wakabayashi, K.2    Nakagama, H.3    Nagao, M.4
  • 2
    • 80051723506 scopus 로고    scopus 로고
    • Metabolism and biomarkers of heterocyclic aromatic amines in molecular epidemiology studies: Lessons learned from aromatic amines
    • Turesky, R. J. and Le Marchand, L. (2011) Metabolism and biomarkers of heterocyclic aromatic amines in molecular epidemiology studies: lessons learned from aromatic amines Chem. Res. Toxicol. 24, 1169-1214 10.1021/tx200135s
    • (2011) Chem. Res. Toxicol. , vol.24 , pp. 1169-1214
    • Turesky, R.J.1    Le Marchand, L.2
  • 4
    • 0032850054 scopus 로고    scopus 로고
    • Development of a solid phase microextraction method for detection of the use of banned azo dyes in coloured textiles and leather
    • Cioni, F., Bartolucci, G., Pieraccini, G., Meloni, S., and Moneti, G. (1999) Development of a solid phase microextraction method for detection of the use of banned azo dyes in coloured textiles and leather Rapid Commun. Mass Spectrom. 13, 1833-1837 10.1002/(SICI)1097-0231(19990930)13:18<1833::AID-RCM725>3.0.CO;2-R
    • (1999) Rapid Commun. Mass Spectrom. , vol.13 , pp. 1833-1837
    • Cioni, F.1    Bartolucci, G.2    Pieraccini, G.3    Meloni, S.4    Moneti, G.5
  • 7
    • 0025922615 scopus 로고
    • Detection of carcinogenic amino-alpha-carbolines and amino-gamma-carbolines in diesel-exhaust particles
    • Manabe, S., Izumikawa, S., Asakuno, K., Wada, O., and Kanai, Y. (1991) Detection of carcinogenic amino-alpha-carbolines and amino-gamma-carbolines in diesel-exhaust particles Environ. Pollut. 70, 255-265 10.1016/0269-7491(91)90013-M
    • (1991) Environ. Pollut. , vol.70 , pp. 255-265
    • Manabe, S.1    Izumikawa, S.2    Asakuno, K.3    Wada, O.4    Kanai, Y.5
  • 8
    • 0019313002 scopus 로고
    • Amino-alpha-carbolines as mutagenic agents in cigarette smoke condensate
    • Yoshida, D. and Matsumoto, T. (1980) Amino-alpha-carbolines as mutagenic agents in cigarette smoke condensate Cancer Lett. 10, 141-149 10.1016/0304-3835(80)90037-3
    • (1980) Cancer Lett. , vol.10 , pp. 141-149
    • Yoshida, D.1    Matsumoto, T.2
  • 9
    • 79251567378 scopus 로고    scopus 로고
    • Quantitative analysis of six heterocyclic aromatic amines in mainstream cigarette smoke condensate using isotope dilution liquid chromatography-electrospray ionization tandem mass spectrometry
    • Zhang, L., Ashley, D. L., and Watson, C. H. (2011) Quantitative analysis of six heterocyclic aromatic amines in mainstream cigarette smoke condensate using isotope dilution liquid chromatography-electrospray ionization tandem mass spectrometry Nicotine Tob. Res. 13, 120-126 10.1093/ntr/ntq219
    • (2011) Nicotine Tob. Res. , vol.13 , pp. 120-126
    • Zhang, L.1    Ashley, D.L.2    Watson, C.H.3
  • 10
    • 0002151911 scopus 로고    scopus 로고
    • Contents in Foods, Beverages and Tobacco
    • (Nagao, M. and Sugimura, T. Eds.), John Wiley & Sons Ltd. Chichester, England
    • Felton, J. S., Jagerstad, M., Knize, M. G., Skog, K., and Wakabayashi, K. (2000) Contents in Foods, Beverages and Tobacco, in Food Borne Carcinogens Heterocyclic Amines (Nagao, M. and Sugimura, T., Eds.) pp 31-71, John Wiley & Sons Ltd., Chichester, England.
    • (2000) Food Borne Carcinogens Heterocyclic Amines , pp. 31-71
    • Felton, J.S.1    Jagerstad, M.2    Knize, M.G.3    Skog, K.4    Wakabayashi, K.5
  • 11
    • 0026049418 scopus 로고
    • Activation of amino-α-carboline, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine, and a copper phthalocyanine cellulose extract of cigarette smoke condensate by cytochrome P-450 enzymes in rat and human liver microsomes
    • Shimada, T. and Guengerich, F. P. (1991) Activation of amino-α-carboline, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine, and a copper phthalocyanine cellulose extract of cigarette smoke condensate by cytochrome P-450 enzymes in rat and human liver microsomes Cancer Res. 51, 5284-5291
    • (1991) Cancer Res. , vol.51 , pp. 5284-5291
    • Shimada, T.1    Guengerich, F.P.2
  • 12
    • 0031815379 scopus 로고    scopus 로고
    • Activation of heterocyclic aromatic amines by rat and human liver microsomes and by purified rat and human cytochrome P450 1A2
    • Turesky, R. J., Constable, A., Richoz, J., Varga, N., Markovic, J., Martin, M. V., and Guengerich, F. P. (1998) Activation of heterocyclic aromatic amines by rat and human liver microsomes and by purified rat and human cytochrome P450 1A2 Chem. Res. Toxicol. 11, 925-936 10.1021/tx980022n
    • (1998) Chem. Res. Toxicol. , vol.11 , pp. 925-936
    • Turesky, R.J.1    Constable, A.2    Richoz, J.3    Varga, N.4    Markovic, J.5    Martin, M.V.6    Guengerich, F.P.7
  • 13
    • 0002973285 scopus 로고    scopus 로고
    • In vitro metabolism
    • Eds. Sugimura, T. and Nagao, M.), John Wiley & Sons. Ltd. (Publisher), Chichester, England
    • Yamazoe, Y. and Nagata, K. (2000) In vitro metabolism, in Food Borne Carcinogens Heterocyclic Amines (Eds. Sugimura, T. and Nagao, M.), John Wiley & Sons., Ltd. (Publisher), Chichester, England, pp 74-89.
    • (2000) Food Borne Carcinogens Heterocyclic Amines , pp. 74-89
    • Yamazoe, Y.1    Nagata, K.2
  • 14
    • 0030995728 scopus 로고    scopus 로고
    • The role of xenobiotic metabolizing enzymes in arylamine toxicity and carcinogenesis: Functional and localization studies
    • Windmill, K. F., McKinnon, R. A., Zhu, X., Gaedigk, A., Grant, D. M., and McManus, M. E. (1997) The role of xenobiotic metabolizing enzymes in arylamine toxicity and carcinogenesis: functional and localization studies Mutat. Res., Fundam. Mol. Mech. Mutagen. 376, 153-160 10.1016/S0027-5107(97)00038-9
    • (1997) Mutat. Res., Fundam. Mol. Mech. Mutagen. , vol.376 , pp. 153-160
    • Windmill, K.F.1    McKinnon, R.A.2    Zhu, X.3    Gaedigk, A.4    Grant, D.M.5    McManus, M.E.6
  • 15
    • 34347256732 scopus 로고    scopus 로고
    • Synthesis and decomposition of an ester derivative of the procarcinogen and promutagen, PhIP, 2-amino-1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridine: Unusual nitrenium ion chemistry
    • Nguyen, T. M. and Novak, M. (2007) Synthesis and decomposition of an ester derivative of the procarcinogen and promutagen, PhIP, 2-amino-1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridine: unusual nitrenium ion chemistry J. Org. Chem. 72, 4698-4706 10.1021/jo070306p
    • (2007) J. Org. Chem. , vol.72 , pp. 4698-4706
    • Nguyen, T.M.1    Novak, M.2
  • 16
    • 0033034183 scopus 로고    scopus 로고
    • DNA adducts of heterocyclic amine food mutagens: Implications for mutagenesis and carcinogenesis
    • Schut, H. A. and Snyderwine, E. G. (1999) DNA adducts of heterocyclic amine food mutagens: implications for mutagenesis and carcinogenesis Carcinogenesis 20, 353-368 10.1093/carcin/20.3.353
    • (1999) Carcinogenesis , vol.20 , pp. 353-368
    • Schut, H.A.1    Snyderwine, E.G.2
  • 17
    • 84867569521 scopus 로고    scopus 로고
    • Quantitation of DNA adducts by stable isotope dilution mass spectrometry
    • Tretyakova, N., Goggin, M., Sangaraju, D., and Janis, G. (2012) Quantitation of DNA adducts by stable isotope dilution mass spectrometry Chem. Res. Toxicol. 25, 2007-2035 10.1021/tx3002548
    • (2012) Chem. Res. Toxicol. , vol.25 , pp. 2007-2035
    • Tretyakova, N.1    Goggin, M.2    Sangaraju, D.3    Janis, G.4
  • 18
    • 0014757218 scopus 로고
    • Carcinogenesis by chemicals: An overview - G. H. A. Clowes memorial lecture
    • Miller, J. A. (1970) Carcinogenesis by chemicals: an overview - G. H. A. Clowes memorial lecture Cancer Res. 30, 559-576
    • (1970) Cancer Res. , vol.30 , pp. 559-576
    • Miller, J.A.1
  • 19
    • 69849102471 scopus 로고    scopus 로고
    • Toward an "omic" physiopathology of reactive chemicals: Thirty years of mass spectrometric study of the protein adducts with endogenous and xenobiotic compounds
    • Rubino, F. M., Pitton, M., Di Fabio, D., and Colombi, A. (2009) Toward an "omic" physiopathology of reactive chemicals: thirty years of mass spectrometric study of the protein adducts with endogenous and xenobiotic compounds Mass Spectrom. Rev. 28, 725-784 10.1002/mas.20207
    • (2009) Mass Spectrom. Rev. , vol.28 , pp. 725-784
    • Rubino, F.M.1    Pitton, M.2    Di Fabio, D.3    Colombi, A.4
  • 20
    • 0025250171 scopus 로고
    • Protein adducts in the molecular dosimetry of chemical carcinogens
    • Skipper, P. L. and Tannenbaum, S. R. (1990) Protein adducts in the molecular dosimetry of chemical carcinogens Carcinogenesis 11, 507-518 10.1093/carcin/11.4.507
    • (1990) Carcinogenesis , vol.11 , pp. 507-518
    • Skipper, P.L.1    Tannenbaum, S.R.2
  • 22
    • 0028300685 scopus 로고
    • Protein adducts as biomarkers of human carcinogen exposure
    • Skipper, P. L., Peng, X., SooHoo, C. K., and Tannenbaum, S. R. (1994) Protein adducts as biomarkers of human carcinogen exposure Drug Metab. Rev. 26, 111-124 10.3109/03602539409029787
    • (1994) Drug Metab. Rev. , vol.26 , pp. 111-124
    • Skipper, P.L.1    Peng, X.2    SooHoo, C.K.3    Tannenbaum, S.R.4
  • 23
    • 0036182039 scopus 로고    scopus 로고
    • Proteomic approaches to characterize protein modifications: New tools to study the effects of environmental exposures
    • Liebler, D. C. (2002) Proteomic approaches to characterize protein modifications: new tools to study the effects of environmental exposures Environ. Health Perspect. 110 (Suppl 1) 3-9 10.1289/ehp.02110s113
    • (2002) Environ. Health Perspect. , vol.110 , pp. 3-9
    • Liebler, D.C.1
  • 24
    • 55249111076 scopus 로고    scopus 로고
    • A tandem MS precursor-ion scan approach to identify variable covalent modification of albumin Cys34: A new tool for studying vascular carbonylation
    • Aldini, G., Regazzoni, L., Orioli, M., Rimoldi, I., Facino, R. M., and Carini, M. (2008) A tandem MS precursor-ion scan approach to identify variable covalent modification of albumin Cys34: a new tool for studying vascular carbonylation J. Mass Spectrom. 43, 1470-1481 10.1002/jms.1419
    • (2008) J. Mass Spectrom. , vol.43 , pp. 1470-1481
    • Aldini, G.1    Regazzoni, L.2    Orioli, M.3    Rimoldi, I.4    Facino, R.M.5    Carini, M.6
  • 25
    • 84864300656 scopus 로고    scopus 로고
    • Adductomics: Characterizing exposures to reactive electrophiles
    • Rappaport, S. M., Li, H., Grigoryan, H., Funk, W. E., and Williams, E. R. (2012) Adductomics: Characterizing exposures to reactive electrophiles Toxicol. Lett. 213, 83-90 10.1016/j.toxlet.2011.04.002
    • (2012) Toxicol. Lett. , vol.213 , pp. 83-90
    • Rappaport, S.M.1    Li, H.2    Grigoryan, H.3    Funk, W.E.4    Williams, E.R.5
  • 26
    • 0018168011 scopus 로고
    • Hemoglobin structure and respiratory transport
    • Perutz, M. F. (1978) Hemoglobin structure and respiratory transport Sci. Am. 239, 92-125 10.1038/scientificamerican1278-92
    • (1978) Sci. Am. , vol.239 , pp. 92-125
    • Perutz, M.F.1
  • 27
    • 33947453415 scopus 로고
    • Spectrophotometric Study of the Reaction of Protein Sulfhydryl Groups with Organic Mercurials
    • Boyer, P. D. (1954) Spectrophotometric Study of the Reaction of Protein Sulfhydryl Groups with Organic Mercurials J. Am. Chem. Soc. 76, 4331-4337 10.1021/ja01646a025
    • (1954) J. Am. Chem. Soc. , vol.76 , pp. 4331-4337
    • Boyer, P.D.1
  • 28
    • 0023915285 scopus 로고
    • Structure of the single stable hemoglobin adduct formed by 4-aminobiphenyl in vivo
    • Ringe, D., Turesky, R. J., Skipper, P. L., and Tannenbaum, S. R. (1988) Structure of the single stable hemoglobin adduct formed by 4-aminobiphenyl in vivo Chem. Res. Toxicol. 1, 22-24 10.1021/tx00001a003
    • (1988) Chem. Res. Toxicol. , vol.1 , pp. 22-24
    • Ringe, D.1    Turesky, R.J.2    Skipper, P.L.3    Tannenbaum, S.R.4
  • 29
    • 84883407801 scopus 로고    scopus 로고
    • Subunit disassembly pathway of human hemoglobin revealing the site-specific role of its cysteine residues
    • Kan, H. I., Chen, I. Y., Zulfajri, M., and Wang, C. C. (2013) Subunit disassembly pathway of human hemoglobin revealing the site-specific role of its cysteine residues J. Phys. Chem. B 117, 9831-9839 10.1021/jp402292b
    • (2013) J. Phys. Chem. B , vol.117 , pp. 9831-9839
    • Kan, H.I.1    Chen, I.Y.2    Zulfajri, M.3    Wang, C.C.4
  • 30
    • 0013943926 scopus 로고
    • The biochemical production of ferrihemoglobin-forming derivatives from aromatic amines, and mechanisms of ferrihemoglobin formation
    • Kiese, M. (1966) The biochemical production of ferrihemoglobin-forming derivatives from aromatic amines, and mechanisms of ferrihemoglobin formation Pharmacol. Rev. 18, 1091-1161
    • (1966) Pharmacol. Rev. , vol.18 , pp. 1091-1161
    • Kiese, M.1
  • 31
    • 34250388872 scopus 로고
    • The fate of phenylhydroxylamine in human red cells
    • Kiese, M. and Taeger, K. (1976) The fate of phenylhydroxylamine in human red cells Naunyn-Schmiedeberg's Arch. Pharmacol. 292, 59-66 10.1007/BF00506490
    • (1976) Naunyn-Schmiedeberg's Arch. Pharmacol. , vol.292 , pp. 59-66
    • Kiese, M.1    Taeger, K.2
  • 32
    • 0024568395 scopus 로고
    • Metabolic oxidation of the carcinogens 4-aminobiphenyl and 4,4′-methylenebis(2-chloroaniline) by human hepatic microsomes and by purified rat hepatic cytochrome P-450 monooxygenases
    • Butler, M. A., Guengerich, F. P., and Kadlubar, F. F. (1989) Metabolic oxidation of the carcinogens 4-aminobiphenyl and 4,4′-methylenebis(2-chloroaniline) by human hepatic microsomes and by purified rat hepatic cytochrome P-450 monooxygenases Cancer Res. 49, 25-31
    • (1989) Cancer Res. , vol.49 , pp. 25-31
    • Butler, M.A.1    Guengerich, F.P.2    Kadlubar, F.F.3
  • 33
    • 0024343858 scopus 로고
    • Human cytochrome P-450 PA (P450IA2), the phenacetin O -deethylase, is primarily responsible for the hepatic 3-demethylation of caffeine and N-oxidation of carcinogenic arylamines
    • Butler, M. A., Iwasaki, M., Guengerich, F. P., and Kadlubar, F. F. (1989) Human cytochrome P-450 PA (P450IA2), the phenacetin O -deethylase, is primarily responsible for the hepatic 3-demethylation of caffeine and N-oxidation of carcinogenic arylamines Proc. Natl. Acad. Sci. U. S. A. 86, 7696-7700 10.1073/pnas.86.20.7696
    • (1989) Proc. Natl. Acad. Sci. U. S. A. , vol.86 , pp. 7696-7700
    • Butler, M.A.1    Iwasaki, M.2    Guengerich, F.P.3    Kadlubar, F.F.4
  • 34
    • 0021707452 scopus 로고
    • Analysis of hemoglobin as a dose monitor for alkylating and arylating agents
    • Neumann, H. G. (1984) Analysis of hemoglobin as a dose monitor for alkylating and arylating agents Arch. Toxicol. 56, 1-6 10.1007/BF00316343
    • (1984) Arch. Toxicol. , vol.56 , pp. 1-6
    • Neumann, H.G.1
  • 35
    • 0021168643 scopus 로고
    • In vivo dosimetry of 4-aminobiphenyl in rats via a cysteine adduct in hemoglobin
    • Green, L. C., Skipper, P. L., Turesky, R. J., Bryant, M. S., and Tannenbaum, S. R. (1984) In vivo dosimetry of 4-aminobiphenyl in rats via a cysteine adduct in hemoglobin Cancer Res. 44, 4254-4259
    • (1984) Cancer Res. , vol.44 , pp. 4254-4259
    • Green, L.C.1    Skipper, P.L.2    Turesky, R.J.3    Bryant, M.S.4    Tannenbaum, S.R.5
  • 36
    • 0023920604 scopus 로고
    • Biomonitoring of aromatic amines and alkylating agents by measuring hemoglobin adducts
    • Neumann, H. G. (1988) Biomonitoring of aromatic amines and alkylating agents by measuring hemoglobin adducts Int. Arch. Occup. Environ. Health 60, 151-155 10.1007/BF00378690
    • (1988) Int. Arch. Occup. Environ. Health , vol.60 , pp. 151-155
    • Neumann, H.G.1
  • 37
    • 0028289754 scopus 로고
    • Aromatic amine-hemoglobin adducts
    • Skipper, P. L. and Stillwell, W. G. (1994) Aromatic amine-hemoglobin adducts Methods Enzymol. 231, 643-649 10.1016/0076-6879(94)31044-0
    • (1994) Methods Enzymol. , vol.231 , pp. 643-649
    • Skipper, P.L.1    Stillwell, W.G.2
  • 38
    • 0023143658 scopus 로고
    • Hemoglobin adducts of 4-aminobiphenyl in smokers and nonsmokers
    • Bryant, M. S., Skipper, P. L., Tannenbaum, S. R., and Maclure, M. (1987) Hemoglobin adducts of 4-aminobiphenyl in smokers and nonsmokers Cancer Res. 47, 602-608
    • (1987) Cancer Res. , vol.47 , pp. 602-608
    • Bryant, M.S.1    Skipper, P.L.2    Tannenbaum, S.R.3    Maclure, M.4
  • 39
    • 0024237525 scopus 로고
    • Hemoglobin adducts of aromatic amines: Associations with smoking status and type of tobacco
    • Bryant, M. S., Vineis, P., Skipper, P. L., and Tannenbaum, S. R. (1988) Hemoglobin adducts of aromatic amines: associations with smoking status and type of tobacco Proc. Natl. Acad. Sci. U. S. A. 85, 9788-9791 10.1073/pnas.85.24.9788
    • (1988) Proc. Natl. Acad. Sci. U. S. A. , vol.85 , pp. 9788-9791
    • Bryant, M.S.1    Vineis, P.2    Skipper, P.L.3    Tannenbaum, S.R.4
  • 42
    • 33751357589 scopus 로고    scopus 로고
    • The urinary metabolite profile of the dietary carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine is predictive of colon DNA adducts after a low-dose exposure in humans
    • Malfatti, M. A., Dingley, K. H., Nowell-Kadlubar, S., Ubick, E. A., Mulakken, N., Nelson, D., Lang, N. P., Felton, J. S., and Turteltaub, K. W. (2006) The urinary metabolite profile of the dietary carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine is predictive of colon DNA adducts after a low-dose exposure in humans Cancer Res. 66, 10541-10547 10.1158/0008-5472.CAN-06-1573
    • (2006) Cancer Res. , vol.66 , pp. 10541-10547
    • Malfatti, M.A.1    Dingley, K.H.2    Nowell-Kadlubar, S.3    Ubick, E.A.4    Mulakken, N.5    Nelson, D.6    Lang, N.P.7    Felton, J.S.8    Turteltaub, K.W.9
  • 43
    • 0036262371 scopus 로고    scopus 로고
    • Excretion of the N 2 -glucuronide conjugate of 2-hydroxyamino-1-methyl-6-phenylimidazo[4,5-b]pyridine in urine and its relationship to CYP1A2 and NAT2 activity levels in humans
    • Stillwell, W. G., Sinha, R., and Tannenbaum, S. R. (2002) Excretion of the N 2 -glucuronide conjugate of 2-hydroxyamino-1-methyl-6-phenylimidazo[4,5-b]pyridine in urine and its relationship to CYP1A2 and NAT2 activity levels in humans Carcinogenesis 23, 831-838 10.1093/carcin/23.5.831
    • (2002) Carcinogenesis , vol.23 , pp. 831-838
    • Stillwell, W.G.1    Sinha, R.2    Tannenbaum, S.R.3
  • 44
    • 4544263908 scopus 로고    scopus 로고
    • Cruciferous vegetable consumption alters the metabolism of the dietary carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in humans
    • Walters, D. G., Young, P. J., Agus, C., Knize, M. G., Boobis, A. R., Gooderham, N. J., and Lake, B. G. (2004) Cruciferous vegetable consumption alters the metabolism of the dietary carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in humans Carcinogenesis 25, 1659-1669 10.1093/carcin/bgh164
    • (2004) Carcinogenesis , vol.25 , pp. 1659-1669
    • Walters, D.G.1    Young, P.J.2    Agus, C.3    Knize, M.G.4    Boobis, A.R.5    Gooderham, N.J.6    Lake, B.G.7
  • 45
    • 0025884641 scopus 로고
    • The measurement of MeIQx adducts with mouse haemoglobin in vitro and in vivo: Implications for human dosimetry
    • Lynch, A. M., Murray, S., Boobis, A. R., Davies, D. S., and Gooderham, N. J. (1991) The measurement of MeIQx adducts with mouse haemoglobin in vitro and in vivo: implications for human dosimetry Carcinogenesis 12, 1067-1072 10.1093/carcin/12.6.1067
    • (1991) Carcinogenesis , vol.12 , pp. 1067-1072
    • Lynch, A.M.1    Murray, S.2    Boobis, A.R.3    Davies, D.S.4    Gooderham, N.J.5
  • 47
    • 0031844149 scopus 로고    scopus 로고
    • Covalent binding of 2-amino-3,8-dimmethylimidazo[4,5-f]quinoxaline to albumin and hemoglobin at environmentally relevant doses. Comparison of human subjects and F344 rats
    • Dingley, K. H., Freeman, S. P., Nelson, D. O., Garner, R. C., and Turteltaub, K. W. (1998) Covalent binding of 2-amino-3,8-dimmethylimidazo[4,5-f]quinoxaline to albumin and hemoglobin at environmentally relevant doses. Comparison of human subjects and F344 rats Drug Metab. Dispos. 26, 825-828
    • (1998) Drug Metab. Dispos. , vol.26 , pp. 825-828
    • Dingley, K.H.1    Freeman, S.P.2    Nelson, D.O.3    Garner, R.C.4    Turteltaub, K.W.5
  • 48
  • 49
    • 0032970624 scopus 로고    scopus 로고
    • DNA and protein adduct formation in the colon and blood of humans after exposure to a dietary-relevant dose of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine
    • Dingley, K. H., Curtis, K. D., Nowell, S., Felton, J. S., Lang, N. P., and Turteltaub, K. W. (1999) DNA and protein adduct formation in the colon and blood of humans after exposure to a dietary-relevant dose of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine Cancer Epidemiol. Biomarkers Prev. 8, 507-512
    • (1999) Cancer Epidemiol. Biomarkers Prev. , vol.8 , pp. 507-512
    • Dingley, K.H.1    Curtis, K.D.2    Nowell, S.3    Felton, J.S.4    Lang, N.P.5    Turteltaub, K.W.6
  • 50
    • 0026040316 scopus 로고
    • Metabolic activation of carcinogenic heterocyclic aromatic amines by human liver and colon
    • Turesky, R. J., Lang, N. P., Butler, M. A., Teitel, C. H., and Kadlubar, F. F. (1991) Metabolic activation of carcinogenic heterocyclic aromatic amines by human liver and colon Carcinogenesis 12, 1839-1845 10.1093/carcin/12.10.1839
    • (1991) Carcinogenesis , vol.12 , pp. 1839-1845
    • Turesky, R.J.1    Lang, N.P.2    Butler, M.A.3    Teitel, C.H.4    Kadlubar, F.F.5
  • 51
    • 0033920961 scopus 로고    scopus 로고
    • In vitro bioactivation of N-hydroxy-2-amino-alpha-carboline
    • King, R. S., Teitel, C. H., and Kadlubar, F. F. (2000) In vitro bioactivation of N-hydroxy-2-amino-alpha-carboline Carcinogenesis 21, 1347-1354 10.1093/carcin/21.7.1347
    • (2000) Carcinogenesis , vol.21 , pp. 1347-1354
    • King, R.S.1    Teitel, C.H.2    Kadlubar, F.F.3
  • 52
    • 0026005327 scopus 로고
    • Absorption spectra of human fetal and adult oxyhemoglobin, de-oxyhemoglobin, carboxyhemoglobin, and methemoglobin
    • Zijlstra, W. G., Buursma, A., and Meeuwsen-van der Roest, W. P. (1991) Absorption spectra of human fetal and adult oxyhemoglobin, de-oxyhemoglobin, carboxyhemoglobin, and methemoglobin Clin. Chem. 37, 1633-1638
    • (1991) Clin. Chem. , vol.37 , pp. 1633-1638
    • Zijlstra, W.G.1    Buursma, A.2    Meeuwsen-Van Der Roest, W.P.3
  • 53
    • 84941312519 scopus 로고    scopus 로고
    • 2-Amino-9H-pyrido[2,3-b]indole (AalphaC) adducts and thiol oxidation of serum albumin as potential biomarkers of tobacco smoke
    • Pathak, K. V., Bellamri, M., Wang, Y., Langouët, S., and Turesky, R. J. (2015) 2-Amino-9H-pyrido[2,3-b]indole (AalphaC) adducts and thiol oxidation of serum albumin as potential biomarkers of tobacco smoke J. Biol. Chem. 290, 16304-16318 10.1074/jbc.M115.646539
    • (2015) J. Biol. Chem. , vol.290 , pp. 16304-16318
    • Pathak, K.V.1    Bellamri, M.2    Wang, Y.3    Langouët, S.4    Turesky, R.J.5
  • 54
    • 84867500404 scopus 로고    scopus 로고
    • Mapping serum albumin adducts of the food-borne carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine by data-dependent tandem mass spectrometry
    • Peng, L., Dasari, S., Tabb, D. L., and Turesky, R. J. (2012) Mapping serum albumin adducts of the food-borne carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine by data-dependent tandem mass spectrometry Chem. Res. Toxicol. 25, 2179-2193 10.1021/tx300253j
    • (2012) Chem. Res. Toxicol. , vol.25 , pp. 2179-2193
    • Peng, L.1    Dasari, S.2    Tabb, D.L.3    Turesky, R.J.4
  • 55
    • 33847401893 scopus 로고    scopus 로고
    • MyriMatch: Highly accurate tandem mass spectral peptide identification by multivariate hypergeometric analysis
    • Tabb, D. L., Fernando, C. G., and Chambers, M. C. (2007) MyriMatch: highly accurate tandem mass spectral peptide identification by multivariate hypergeometric analysis J. Proteome. Res. 6, 654-661 10.1021/pr0604054
    • (2007) J. Proteome. Res. , vol.6 , pp. 654-661
    • Tabb, D.L.1    Fernando, C.G.2    Chambers, M.C.3
  • 57
    • 33744807436 scopus 로고    scopus 로고
    • Gaussian-weighted RMSD superposition of proteins: A structural comparison for flexible proteins and predicted protein structures
    • Damm, K. L. and Carlson, H. A. (2006) Gaussian-weighted RMSD superposition of proteins: a structural comparison for flexible proteins and predicted protein structures Biophys. J. 90, 4558-4573 10.1529/biophysj.105.066654
    • (2006) Biophys. J. , vol.90 , pp. 4558-4573
    • Damm, K.L.1    Carlson, H.A.2
  • 58
    • 84865271039 scopus 로고    scopus 로고
    • Variability in docking success rates due to dataset preparation
    • Corbeil, C. R., Williams, C. I., and Labute, P. (2012) Variability in docking success rates due to dataset preparation J. Comput.-Aided Mol. Des. 26, 775-786 10.1007/s10822-012-9570-1
    • (2012) J. Comput.-Aided Mol. Des. , vol.26 , pp. 775-786
    • Corbeil, C.R.1    Williams, C.I.2    Labute, P.3
  • 59
    • 46449095476 scopus 로고    scopus 로고
    • The generalized Born/volume integral implicit solvent model: Estimation of the free energy of hydration using London dispersion instead of atomic surface area
    • Labute, P. (2008) The generalized Born/volume integral implicit solvent model: estimation of the free energy of hydration using London dispersion instead of atomic surface area J. Comput. Chem. 29, 1693-1698 10.1002/jcc.20933
    • (2008) J. Comput. Chem. , vol.29 , pp. 1693-1698
    • Labute, P.1
  • 60
    • 0015493853 scopus 로고
    • The thiol groups of human hemoglobin carrying heme only on the α-chains
    • Birchmeier, W., Glatthaar, B. E., Winterhalter, K. H., and Bradshaw, R. A. (1972) The thiol groups of human hemoglobin carrying heme only on the α-chains Eur. J. Biochem. 28, 533-537 10.1111/j.1432-1033.1972.tb01941.x
    • (1972) Eur. J. Biochem. , vol.28 , pp. 533-537
    • Birchmeier, W.1    Glatthaar, B.E.2    Winterhalter, K.H.3    Bradshaw, R.A.4
  • 62
    • 78549293591 scopus 로고    scopus 로고
    • Cleavage specificities of the brother and sister proteases Lys-C and Lys-N
    • Raijmakers, R., Neerincx, P., Mohammed, S., and Heck, A. J. (2009) Cleavage specificities of the brother and sister proteases Lys-C and Lys-N Chem. Commun. (Cambridge, U. K.) 46, 8827-8829 10.1039/c0cc02523b
    • (2009) Chem. Commun. (Cambridge, U. K.) , vol.46 , pp. 8827-8829
    • Raijmakers, R.1    Neerincx, P.2    Mohammed, S.3    Heck, A.J.4
  • 63
    • 0026503259 scopus 로고
    • Substrate preferences of glutamic-acid-specific endopeptidases assessed by synthetic peptide substrates based on intramolecular fluorescence quenching
    • Breddam, K. and Meldal, M. (1992) Substrate preferences of glutamic-acid-specific endopeptidases assessed by synthetic peptide substrates based on intramolecular fluorescence quenching Eur. J. Biochem. 206, 103-107 10.1111/j.1432-1033.1992.tb16906.x
    • (1992) Eur. J. Biochem. , vol.206 , pp. 103-107
    • Breddam, K.1    Meldal, M.2
  • 64
    • 30144438909 scopus 로고    scopus 로고
    • Collision-Induced Dissociation (CID) of Peptides and Proteins.
    • Elsevier: San Diego, California
    • Wells, M. J. and McLuckey, S. A. Collision-Induced Dissociation (CID) of Peptides and Proteins. In Biological Mass Spectrometry, Methods in Enzymology, Vol. 402; Elsevier: San Diego, California, 2005; pp 148-185.
    • (2005) Biological Mass Spectrometry, Methods in Enzymology , vol.402 , pp. 148-185
    • Wells, M.J.1    McLuckey, S.A.2
  • 65
    • 0345547409 scopus 로고    scopus 로고
    • Neutral loss of amino acid residues from protonated peptides in collision-induced dissociation generates N- or C-terminal sequence ladders
    • Salek, M. and Lehmann, W. D. (2003) Neutral loss of amino acid residues from protonated peptides in collision-induced dissociation generates N- or C-terminal sequence ladders J. Mass Spectrom. 38, 1143-1149 10.1002/jms.531
    • (2003) J. Mass Spectrom. , vol.38 , pp. 1143-1149
    • Salek, M.1    Lehmann, W.D.2
  • 66
    • 33847415405 scopus 로고    scopus 로고
    • Genetic variation in mouse beta globin cysteine content modifies glutathione metabolism: Implications for the use of mouse models
    • Hempe, J. M., Ory-Ascani, J., and Hsia, D. (2007) Genetic variation in mouse beta globin cysteine content modifies glutathione metabolism: implications for the use of mouse models Exp. Biol. Med. 232, 437-444
    • (2007) Exp. Biol. Med. , vol.232 , pp. 437-444
    • Hempe, J.M.1    Ory-Ascani, J.2    Hsia, D.3
  • 68
    • 33745571654 scopus 로고    scopus 로고
    • 1.25 A resolution crystal structures of human haemoglobin in the oxy, deoxy and carbonmonoxy forms
    • Park, S. Y., Yokoyama, T., Shibayama, N., Shiro, Y., and Tame, J. R. (2006) 1.25 A resolution crystal structures of human haemoglobin in the oxy, deoxy and carbonmonoxy forms J. Mol. Biol. 360, 690-701 10.1016/j.jmb.2006.05.036
    • (2006) J. Mol. Biol. , vol.360 , pp. 690-701
    • Park, S.Y.1    Yokoyama, T.2    Shibayama, N.3    Shiro, Y.4    Tame, J.R.5
  • 70
    • 20444417111 scopus 로고    scopus 로고
    • The enigma of the liganded hemoglobin end state: A novel quaternary structure of human carbonmonoxy hemoglobin
    • Safo, M. K. and Abraham, D. J. (2005) The enigma of the liganded hemoglobin end state: a novel quaternary structure of human carbonmonoxy hemoglobin Biochemistry 44, 8347-8359 10.1021/bi050412q
    • (2005) Biochemistry , vol.44 , pp. 8347-8359
    • Safo, M.K.1    Abraham, D.J.2
  • 71
    • 0030000410 scopus 로고    scopus 로고
    • Crystal structure of T state haemoglobin with oxygen bound at all four haems
    • Paoli, M., Liddington, R., Tame, J., Wilkinson, A., and Dodson, G. (1996) Crystal structure of T state haemoglobin with oxygen bound at all four haems J. Mol. Biol. 256, 775-792 10.1006/jmbi.1996.0124
    • (1996) J. Mol. Biol. , vol.256 , pp. 775-792
    • Paoli, M.1    Liddington, R.2    Tame, J.3    Wilkinson, A.4    Dodson, G.5
  • 72
    • 0033562690 scopus 로고    scopus 로고
    • High-precision measurement of hydrogen bond lengths in proteins by nuclear magnetic resonance methods
    • Harris, T. K. and Mildvan, A. S. (1999) High-precision measurement of hydrogen bond lengths in proteins by nuclear magnetic resonance methods Proteins: Struct., Funct., Genet. 35, 275-282 10.1002/(SICI)1097-0134(19990515)35:3<275::AID-PROT1>3.0.CO;2-V
    • (1999) Proteins: Struct., Funct., Genet. , vol.35 , pp. 275-282
    • Harris, T.K.1    Mildvan, A.S.2
  • 75
    • 84872527191 scopus 로고    scopus 로고
    • Capturing labile sulfenamide and sulfinamide serum albumin adducts of carcinogenic arylamines by chemical oxidation
    • Peng, L. and Turesky, R. J. (2013) Capturing labile sulfenamide and sulfinamide serum albumin adducts of carcinogenic arylamines by chemical oxidation Anal. Chem. 85, 1065-1072 10.1021/ac3028273
    • (2013) Anal. Chem. , vol.85 , pp. 1065-1072
    • Peng, L.1    Turesky, R.J.2
  • 76
    • 84947235522 scopus 로고    scopus 로고
    • Data-independent-acquisition mass spectrometry for identification of targeted-peptide site-specific modifications
    • Porter, C. J. and Bereman, M. S. (2015) Data-independent-acquisition mass spectrometry for identification of targeted-peptide site-specific modifications Anal. Bioanal. Chem. 407, 6627-6635 10.1007/s00216-015-8819-7
    • (2015) Anal. Bioanal. Chem. , vol.407 , pp. 6627-6635
    • Porter, C.J.1    Bereman, M.S.2
  • 77
    • 0042560666 scopus 로고
    • Oxidation of phenylhydroxylamine in aqueous solution: A model for study of the carcinogenic effect of primary aromatic amines
    • Becker, A. R. and Sternson, L. A. (1981) Oxidation of phenylhydroxylamine in aqueous solution: a model for study of the carcinogenic effect of primary aromatic amines Proc. Natl. Acad. Sci. U. S. A. 78, 2003-2007 10.1073/pnas.78.4.2003
    • (1981) Proc. Natl. Acad. Sci. U. S. A. , vol.78 , pp. 2003-2007
    • Becker, A.R.1    Sternson, L.A.2
  • 78
    • 0023692347 scopus 로고
    • Superoxide dismutase-mediated reversible conversion of 3-hydroxyamino-1-methyl-5H-pyrido[4,3-b]indole, the N-hydroxy derivative of Trp-P-2, into its nitroso derivative
    • Hiramoto, K., Negishi, K., Namba, T., Katsu, T., and Hayatsu, H. (1988) Superoxide dismutase-mediated reversible conversion of 3-hydroxyamino-1-methyl-5H-pyrido[4,3-b]indole, the N-hydroxy derivative of Trp-P-2, into its nitroso derivative Carcinogenesis 9, 2003-2008 10.1093/carcin/9.11.2003
    • (1988) Carcinogenesis , vol.9 , pp. 2003-2008
    • Hiramoto, K.1    Negishi, K.2    Namba, T.3    Katsu, T.4    Hayatsu, H.5
  • 79
    • 0027221713 scopus 로고
    • Hemoglobin binding of aromatic amines: Molecular dosimetry and quantitative structure-activity relationships for N-oxidation
    • Sabbioni, G. (1993) Hemoglobin binding of aromatic amines: molecular dosimetry and quantitative structure-activity relationships for N-oxidation Environ. Health Perspect. 99, 213-216 10.1289/ehp.9399213
    • (1993) Environ. Health Perspect. , vol.99 , pp. 213-216
    • Sabbioni, G.1
  • 80
    • 0024437247 scopus 로고
    • Comparison of in vivo binding of aromatic nitro and amino compounds to rat hemoglobin
    • Junzo, S., Shin-Ichl, M., Osamu, M., Seiji, H., and Shizuo, S. (1989) Comparison of in vivo binding of aromatic nitro and amino compounds to rat hemoglobin Biochem. Pharmacol. 38, 3511-3519 10.1016/0006-2952(89)90122-6
    • (1989) Biochem. Pharmacol. , vol.38 , pp. 3511-3519
    • Junzo, S.1    Shin-Ichl, M.2    Osamu, M.3    Seiji, H.4    Shizuo, S.5
  • 81
    • 0041003970 scopus 로고
    • The influence of oxygenation on the reactivity of the - SH groups of hemoglobin
    • Benesch, R. E. and Benesch, R. (1962) The influence of oxygenation on the reactivity of the - SH groups of hemoglobin Biochemistry 1, 735-738 10.1021/bi00911a002
    • (1962) Biochemistry , vol.1 , pp. 735-738
    • Benesch, R.E.1    Benesch, R.2
  • 82
    • 0011680913 scopus 로고
    • The Characterization of Modified Human Hemoglobin. I. Reaction with Iodoacetamide and N-Ethylmaleimide
    • Guidotti, G. and Konigsberg, W. (1964) The Characterization of Modified Human Hemoglobin. I. Reaction with Iodoacetamide and N-Ethylmaleimide J. Biol. Chem. 239, 1474-1484
    • (1964) J. Biol. Chem. , vol.239 , pp. 1474-1484
    • Guidotti, G.1    Konigsberg, W.2
  • 83
    • 33947312669 scopus 로고    scopus 로고
    • The role of beta93 Cys in the inhibition of Hb S fiber formation
    • Knee, K. M., Roden, C. K., Flory, M. R., and Mukerji, I. (2007) The role of beta93 Cys in the inhibition of Hb S fiber formation Biophys. Chem. 127, 181-193 10.1016/j.bpc.2007.02.002
    • (2007) Biophys. Chem. , vol.127 , pp. 181-193
    • Knee, K.M.1    Roden, C.K.2    Flory, M.R.3    Mukerji, I.4
  • 84
    • 0001720527 scopus 로고
    • A new method for the preparation of alpha and beta subunits of human hemoglobin
    • Bucci, E. and Fronticelli, C. (1965) A new method for the preparation of alpha and beta subunits of human hemoglobin J. Biol. Chem. 240, PC551-552
    • (1965) J. Biol. Chem. , vol.240 , pp. PC551-552
    • Bucci, E.1    Fronticelli, C.2
  • 85
    • 0036010944 scopus 로고    scopus 로고
    • Structural analysis of styrene oxide/haemoglobin adducts by mass spectrometry: Identification of suitable biomarkers for human exposure evaluation
    • Basile, A., Ferranti, P., Mamone, G., Manco, I., Pocsfalvi, G., Malorni, A., Acampora, A., and Sannolo, N. (2002) Structural analysis of styrene oxide/haemoglobin adducts by mass spectrometry: identification of suitable biomarkers for human exposure evaluation Rapid Commun. Mass Spectrom. 16, 871-878 10.1002/rcm.655
    • (2002) Rapid Commun. Mass Spectrom. , vol.16 , pp. 871-878
    • Basile, A.1    Ferranti, P.2    Mamone, G.3    Manco, I.4    Pocsfalvi, G.5    Malorni, A.6    Acampora, A.7    Sannolo, N.8
  • 86
    • 0031015162 scopus 로고    scopus 로고
    • Characterisation of S-nitrosohaemoglobin by mass spectrometry
    • Ferranti, P., Malorni, A., Mamone, G., Sannolo, N., and Marino, G. (1997) Characterisation of S-nitrosohaemoglobin by mass spectrometry FEBS Lett. 400, 19-24 10.1016/S0014-5793(96)01258-6
    • (1997) FEBS Lett. , vol.400 , pp. 19-24
    • Ferranti, P.1    Malorni, A.2    Mamone, G.3    Sannolo, N.4    Marino, G.5
  • 87
    • 77956881778 scopus 로고    scopus 로고
    • Identification of covalent binding sites of ethyl 2-cyanoacrylate, methyl methacrylate and 2-hydroxyethyl methacrylate in human hemoglobin using LC/MS/MS techniques
    • Jeppsson, M. C., Mortstedt, H., Ferrari, G., Jonsson, B. A., and Lindh, C. H. (2010) Identification of covalent binding sites of ethyl 2-cyanoacrylate, methyl methacrylate and 2-hydroxyethyl methacrylate in human hemoglobin using LC/MS/MS techniques J. Chromatogr. B: Anal. Technol. Biomed. Life Sci. 878, 2474-2482 10.1016/j.jchromb.2010.04.026
    • (2010) J. Chromatogr. B: Anal. Technol. Biomed. Life Sci. , vol.878 , pp. 2474-2482
    • Jeppsson, M.C.1    Mortstedt, H.2    Ferrari, G.3    Jonsson, B.A.4    Lindh, C.H.5
  • 88
    • 0026512811 scopus 로고
    • Hemoglobin binding of monocyclic aromatic amines: Molecular dosimetry and quantitative structure activity relationships for the N-oxidation
    • Sabbioni, G. (1992) Hemoglobin binding of monocyclic aromatic amines: molecular dosimetry and quantitative structure activity relationships for the N-oxidation Chem.-Biol. Interact. 81, 91-117 10.1016/0009-2797(92)90029-K
    • (1992) Chem.-Biol. Interact. , vol.81 , pp. 91-117
    • Sabbioni, G.1


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