메뉴 건너뛰기




Volumn 107, Issue 1, 2009, Pages 144-155

Tyrosines of human and mouse transferrin covalently labeled by organophosphorus agents: A new motif for binding to proteins that have no active site serine

Author keywords

Mass spectrometry; Plasma; Sarin; Soman; Transferrin; Tyrosine residue

Indexed keywords

ALBUMIN; ARGINYLTYROSYLTHREONYLARGININE; CHLORPYRIFOS; DICHLORVOS; DYFLOS; ORGANOPHOSPHORUS COMPOUND; SARIN; SERINE; SOMAN; SYNTHETIC PEPTIDE; TRANSFERRIN; TUBULIN; TYROSINE; UNCLASSIFIED DRUG;

EID: 58049194183     PISSN: 10966080     EISSN: 10960929     Source Type: Journal    
DOI: 10.1093/toxsci/kfn211     Document Type: Article
Times cited : (30)

References (38)
  • 1
    • 0242539881 scopus 로고    scopus 로고
    • Serotonergic systems targeted by developmental exposure to chlorpyrifos: Effects during different critical periods
    • Aldridge, J. E., Seidler, F. J., Meyer, A., Thillai, I., and Slotkin, T. A. (2003). Serotonergic systems targeted by developmental exposure to chlorpyrifos: Effects during different critical periods. Environ. Health Perspect. 111, 1736-1743.
    • (2003) Environ. Health Perspect , vol.111 , pp. 1736-1743
    • Aldridge, J.E.1    Seidler, F.J.2    Meyer, A.3    Thillai, I.4    Slotkin, T.A.5
  • 2
    • 58049207394 scopus 로고
    • The action of diisopropyl phosphorofluoridate and other anticholinesterases on amino acids
    • Ashbolt, R. F., and Rydon, H. N. (1957). The action of diisopropyl phosphorofluoridate and other anticholinesterases on amino acids. Biochem. J. 66, 237-242.
    • (1957) Biochem. J , vol.66 , pp. 237-242
    • Ashbolt, R.F.1    Rydon, H.N.2
  • 3
    • 0015919687 scopus 로고
    • The reaction of ferric salts with transferrin
    • Bates, G. W., and Schlabach, M. R. (1973). The reaction of ferric salts with transferrin. J. Biol. Chem. 248, 3228-3232.
    • (1973) J. Biol. Chem , vol.248 , pp. 3228-3232
    • Bates, G.W.1    Schlabach, M.R.2
  • 4
    • 0035798826 scopus 로고    scopus 로고
    • Diethylphosphorylation of rat cardiac M2 muscarinic receptor by chlorpyrifos oxon in vitro
    • Bomser, J. A., and Casida, J. E. (2001). Diethylphosphorylation of rat cardiac M2 muscarinic receptor by chlorpyrifos oxon in vitro. Toxicol. Lett. 119, 21-26.
    • (2001) Toxicol. Lett , vol.119 , pp. 21-26
    • Bomser, J.A.1    Casida, J.E.2
  • 5
    • 4243148518 scopus 로고    scopus 로고
    • Organophosphate toxicology: Safety aspects of nonacetylcholinesterase secondary targets
    • Casida, J. E., and Quistad, G. B. (2004). Organophosphate toxicology: Safety aspects of nonacetylcholinesterase secondary targets. Chem. Res. Toxicol. 17, 983-998.
    • (2004) Chem. Res. Toxicol , vol.17 , pp. 983-998
    • Casida, J.E.1    Quistad, G.B.2
  • 6
    • 0014670401 scopus 로고
    • Reaction of a specific tyrosine residue of papain with diisopropylfluorophosphate
    • Chaiken, I. M., and Smith, E. L. (1969). Reaction of a specific tyrosine residue of papain with diisopropylfluorophosphate. J. Biol. Chem. 244, 4247-4250.
    • (1969) J. Biol. Chem , vol.244 , pp. 4247-4250
    • Chaiken, I.M.1    Smith, E.L.2
  • 8
    • 0036113678 scopus 로고    scopus 로고
    • Retrospective detection of exposure to organophosphorus anti-cholinesterases: Mass spectrometric analysis of phosphorylated human butyrylcholinesterase
    • Fidder, A., Hulst, A. G., Noort, D., de Ruiter, R., van der Schans, M. J., Benschop, H. P., and Langenberg, J. P. (2002). Retrospective detection of exposure to organophosphorus anti-cholinesterases: Mass spectrometric analysis of phosphorylated human butyrylcholinesterase. Chem. Res. Toxicol. 15, 582-590.
    • (2002) Chem. Res. Toxicol , vol.15 , pp. 582-590
    • Fidder, A.1    Hulst, A.G.2    Noort, D.3    de Ruiter, R.4    van der Schans, M.J.5    Benschop, H.P.6    Langenberg, J.P.7
  • 9
    • 33846025142 scopus 로고    scopus 로고
    • Chlorpyrifos, chlorpyrifos-oxon, and diisopropyl-fluorophosphate inhibit kinesin-dependent microtubule motility
    • Gearhart, D. A., Sickles, D. W., Buccafusco, J. J., Prendergast, M. A., and Terry, A. V., Jr. (2007). Chlorpyrifos, chlorpyrifos-oxon, and diisopropyl-fluorophosphate inhibit kinesin-dependent microtubule motility. Toxicol. Appl. Pharmacol. 218, 20-29.
    • (2007) Toxicol. Appl. Pharmacol , vol.218 , pp. 20-29
    • Gearhart, D.A.1    Sickles, D.W.2    Buccafusco, J.J.3    Prendergast, M.A.4    Terry Jr., A.V.5
  • 10
    • 50649103273 scopus 로고    scopus 로고
    • Mass spectrometry identifies covalent binding of soman, sarin, chlorpyrifos oxon, diisopropyl fluorophosphate, and FP-biotin to tyrosines on tubulin: A potential mechanism of long term toxicity by organophosphorus agents
    • Grigoryan, H., Schopfer, L. M., Thompson, C. M., Terry, A. V., Masson, P., and Lockridge, O. (2008). Mass spectrometry identifies covalent binding of soman, sarin, chlorpyrifos oxon, diisopropyl fluorophosphate, and FP-biotin to tyrosines on tubulin: A potential mechanism of long term toxicity by organophosphorus agents. Chem. Biol. Interact. 175, 180-186.
    • (2008) Chem. Biol. Interact , vol.175 , pp. 180-186
    • Grigoryan, H.1    Schopfer, L.M.2    Thompson, C.M.3    Terry, A.V.4    Masson, P.5    Lockridge, O.6
  • 11
    • 0346037306 scopus 로고    scopus 로고
    • Low-level sarin-induced alteration of immune system reaction in inbred BALB/c mice
    • Kassa, J., Krocova, Z., Sevelova, L., Sheshko, V., Kasalova, I., and Neubauerova, V. (2003). Low-level sarin-induced alteration of immune system reaction in inbred BALB/c mice. Toxicology 187, 195-203.
    • (2003) Toxicology , vol.187 , pp. 195-203
    • Kassa, J.1    Krocova, Z.2    Sevelova, L.3    Sheshko, V.4    Kasalova, I.5    Neubauerova, V.6
  • 12
    • 0030726887 scopus 로고    scopus 로고
    • Chlorpyrifos, parathion, and their oxons bind to and desensitize a nicotinic acetylcholine receptor: Relevance to their toxicities
    • Katz, E. J., Cortes, V. I., Eldefrawi, M. E., and Eldefrawi, A. T. (1997). Chlorpyrifos, parathion, and their oxons bind to and desensitize a nicotinic acetylcholine receptor: Relevance to their toxicities. Toxicol. Appl. Pharmacol. 146, 227-236.
    • (1997) Toxicol. Appl. Pharmacol , vol.146 , pp. 227-236
    • Katz, E.J.1    Cortes, V.I.2    Eldefrawi, M.E.3    Eldefrawi, A.T.4
  • 13
    • 12344289246 scopus 로고    scopus 로고
    • Organophosphorus insecticides induce airway hyperreactivity by decreasing neuronal M2 muscarinic receptor function independent of acetylcholinesterase inhibition
    • Lein, P. J., and Fryer, A. D. (2005). Organophosphorus insecticides induce airway hyperreactivity by decreasing neuronal M2 muscarinic receptor function independent of acetylcholinesterase inhibition. Toxicol. Sci. 83, 166-176.
    • (2005) Toxicol. Sci , vol.83 , pp. 166-176
    • Lein, P.J.1    Fryer, A.D.2
  • 15
    • 33846389181 scopus 로고    scopus 로고
    • Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry assay for organophosphorus toxicants bound to human albumin at Tyr411
    • Li, B., Schopfer, L. M., Hinrichs, S. H., Masson, P., and Lockridge, O. (2007). Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry assay for organophosphorus toxicants bound to human albumin at Tyr411. Anal. Biochem. 361, 263-272.
    • (2007) Anal. Biochem , vol.361 , pp. 263-272
    • Li, B.1    Schopfer, L.M.2    Hinrichs, S.H.3    Masson, P.4    Lockridge, O.5
  • 16
    • 27544478172 scopus 로고    scopus 로고
    • Butyrylcholinesterase, paraoxonase, and albumin esterase, but not carboxylesterase, are present in human plasma
    • Li, B., Sedlacek, M., Manoharan, I., Boopathy, R., Duysen, E. G., Masson, P., and Lockridge, O. (2005). Butyrylcholinesterase, paraoxonase, and albumin esterase, but not carboxylesterase, are present in human plasma. Biochem. Pharmacol. 70, 1673-1684.
    • (2005) Biochem. Pharmacol , vol.70 , pp. 1673-1684
    • Li, B.1    Sedlacek, M.2    Manoharan, I.3    Boopathy, R.4    Duysen, E.G.5    Masson, P.6    Lockridge, O.7
  • 17
    • 27544478065 scopus 로고    scopus 로고
    • Large scale purification of butyrylcholinesterase from human glasma suitable for injection into monkeys; a potential new therapeutic for protection against cocaine and nerve agent toxicity
    • online publication
    • Lockridge, O., Schopfer, L. M., Winger, G., and Woods, J. H. (2005). Large scale purification of butyrylcholinesterase from human glasma suitable for injection into monkeys; a potential new therapeutic for protection against cocaine and nerve agent toxicity. J. Med. CBR Def. 3, online publication
    • (2005) J. Med. CBR Def , vol.3
    • Lockridge, O.1    Schopfer, L.M.2    Winger, G.3    Woods, J.H.4
  • 18
    • 53049095404 scopus 로고    scopus 로고
    • Pseudo-esterase activity of human albumin: Slow turnover on tyrosine 411 and stable acetylation of 82 residues including 59 lysines
    • Lockridge, O., Xue, W., Gaydess, A., Grigoryan, H., Ding, S. J., Schopfer, L. M., Hinrichs, S. H., and Masson, P. (2008). Pseudo-esterase activity of human albumin: Slow turnover on tyrosine 411 and stable acetylation of 82 residues including 59 lysines. J. Biol. Chem. 283, 22582-22590.
    • (2008) J. Biol. Chem , vol.283 , pp. 22582-22590
    • Lockridge, O.1    Xue, W.2    Gaydess, A.3    Grigoryan, H.4    Ding, S.J.5    Schopfer, L.M.6    Hinrichs, S.H.7    Masson, P.8
  • 20
    • 0013300287 scopus 로고    scopus 로고
    • Carboxylesterase: Specificity and spontaneous reactivation of an endogenous scavenger for organophosphorus compounds
    • Maxwell, D. M., and Brecht, K. M. (2001). Carboxylesterase: Specificity and spontaneous reactivation of an endogenous scavenger for organophosphorus compounds. J. Appl. Toxicol. 21(Suppl. 1), S103-S107.
    • (2001) J. Appl. Toxicol , vol.21 , Issue.SUPPL. 1
    • Maxwell, D.M.1    Brecht, K.M.2
  • 21
    • 0013830343 scopus 로고
    • Evidence for alkylphosphorylation of tyrosyl residues of stem bromelain by diisopropylphosphorofluoridate
    • Murachi, T., Inagami, T., and Yasui, M. (1965). Evidence for alkylphosphorylation of tyrosyl residues of stem bromelain by diisopropylphosphorofluoridate. Biochemistry 4, 2815-2825.
    • (1965) Biochemistry , vol.4 , pp. 2815-2825
    • Murachi, T.1    Inagami, T.2    Yasui, M.3
  • 23
    • 0033434080 scopus 로고    scopus 로고
    • Probability-based protein identification by searching sequence databases using mass spectrometry data
    • Perkins, D. N., Pappin, D. J., Creasy, D. M., and Cottrell, J. S. (1999). Probability-based protein identification by searching sequence databases using mass spectrometry data. Electrophoresis 20, 3551-3567.
    • (1999) Electrophoresis , vol.20 , pp. 3551-3567
    • Perkins, D.N.1    Pappin, D.J.2    Creasy, D.M.3    Cottrell, J.S.4
  • 24
    • 0033369584 scopus 로고    scopus 로고
    • Organophosphorus pesticides: Do they all have the same mechanism of toxicity?
    • Pope, C. N. (1999). Organophosphorus pesticides: Do they all have the same mechanism of toxicity? J. Toxicol. Environ. Health B Crit. Rev. 2, 161-181.
    • (1999) J. Toxicol. Environ. Health B Crit. Rev , vol.2 , pp. 161-181
    • Pope, C.N.1
  • 26
    • 26444451703 scopus 로고    scopus 로고
    • Blood acylpeptide hydrolase activity is a sensitive marker for exposure to some organophosphate toxicants
    • Quistad, G. B., Klintenberg, R., and Casida, J. E. (2005). Blood acylpeptide hydrolase activity is a sensitive marker for exposure to some organophosphate toxicants. Toxicol. Sci. 86, 291-299.
    • (2005) Toxicol. Sci , vol.86 , pp. 291-299
    • Quistad, G.B.1    Klintenberg, R.2    Casida, J.E.3
  • 27
    • 0037026728 scopus 로고    scopus 로고
    • Cannabinoid CB1 receptor as a target for chlorpyrifos oxon and other organophosphorus pesticides
    • Quistad, G. B., Nomura, D. K., Sparks, S. E., Segall, Y., and Casida, J. E. (2002). Cannabinoid CB1 receptor as a target for chlorpyrifos oxon and other organophosphorus pesticides. Toxicol. Lett. 135, 89-93.
    • (2002) Toxicol. Lett , vol.135 , pp. 89-93
    • Quistad, G.B.1    Nomura, D.K.2    Sparks, S.E.3    Segall, Y.4    Casida, J.E.5
  • 28
    • 0033851169 scopus 로고    scopus 로고
    • Identification of acylpeptide hydrolase as a sensitive site for reaction with organophosphorus compounds and a potential target for cognitive enhancing drugs
    • Richards, P. G., Johnson, M. K., and Ray, D. E. (2000). Identification of acylpeptide hydrolase as a sensitive site for reaction with organophosphorus compounds and a potential target for cognitive enhancing drugs. Mol. Pharmacol. 58, 577-583.
    • (2000) Mol. Pharmacol , vol.58 , pp. 577-583
    • Richards, P.G.1    Johnson, M.K.2    Ray, D.E.3
  • 29
    • 27744603887 scopus 로고    scopus 로고
    • Structure/function overview of proteins involved in iron storage and transport
    • Sargent, P. J., Farnaud, S., and Evans, R. W. (2005). Structure/function overview of proteins involved in iron storage and transport. Curr. Med. Chem. 12, 2683-2693.
    • (2005) Curr. Med. Chem , vol.12 , pp. 2683-2693
    • Sargent, P.J.1    Farnaud, S.2    Evans, R.W.3
  • 30
    • 27544434661 scopus 로고    scopus 로고
    • Characteristic mass spectral fragments of the organophosphorus agent FP-biotin and FP-biotinylated peptides from trypsin and bovine albumin (Tryr410)
    • Schopfer, L. M., Champion, M. M., Tamblyn, N., Thompson, C. M., and Lockridge, O. (2005). Characteristic mass spectral fragments of the organophosphorus agent FP-biotin and FP-biotinylated peptides from trypsin and bovine albumin (Tryr410). Anal. Biochem. 345, 122-132.
    • (2005) Anal. Biochem , vol.345 , pp. 122-132
    • Schopfer, L.M.1    Champion, M.M.2    Tamblyn, N.3    Thompson, C.M.4    Lockridge, O.5
  • 31
    • 0036353211 scopus 로고    scopus 로고
    • Noncholinesterase mechanisms of chlorpyrifos neurotoxicity: Altered phosphorylation of Ca2+/cAMP response element binding protein in cultured neurons
    • Schuh, R. A., Lein, P. J., Beckles, R. A., and Jett, D. A. (2002). Noncholinesterase mechanisms of chlorpyrifos neurotoxicity: Altered phosphorylation of Ca2+/cAMP response element binding protein in cultured neurons. Toxicol. Appl. Pharmacol. 182, 176-185.
    • (2002) Toxicol. Appl. Pharmacol , vol.182 , pp. 176-185
    • Schuh, R.A.1    Lein, P.J.2    Beckles, R.A.3    Jett, D.A.4
  • 32
    • 10044255212 scopus 로고    scopus 로고
    • Block of neuronal nicotinic acetylcholine receptors by organophosphate insecticides
    • Smulders, C. J., Bueters, T. J., Vailati, S., van Kleef, R. G., and Vijverberg, H. P. (2004). Block of neuronal nicotinic acetylcholine receptors by organophosphate insecticides. Toxicol. Sci. 85, 545-554.
    • (2004) Toxicol. Sci , vol.85 , pp. 545-554
    • Smulders, C.J.1    Bueters, T.J.2    Vailati, S.3    van Kleef, R.G.4    Vijverberg, H.P.5
  • 33
    • 0031194056 scopus 로고    scopus 로고
    • Cellular mechanisms for developmental toxicity of chlorpyrifos: Targeting the adenylyl cyclase signaling cascade
    • Song, X., Seidler, F. J., Saleh, J. L., Zhang, J., Padilla, S., and Slotkin, T. A. (1997). Cellular mechanisms for developmental toxicity of chlorpyrifos: Targeting the adenylyl cyclase signaling cascade. Toxicol. Appl. Pharmacol. 145, 158-174.
    • (1997) Toxicol. Appl. Pharmacol , vol.145 , pp. 158-174
    • Song, X.1    Seidler, F.J.2    Saleh, J.L.3    Zhang, J.4    Padilla, S.5    Slotkin, T.A.6
  • 34
    • 34548098919 scopus 로고    scopus 로고
    • Terry, A. V., Jr., Gearhart, D. A., Beck, W. D., Jr., Truan, J. N., Middlemore, M. L., Williamson, L. N., Bartlett, M. G., Prendergast, M. A., Sickles, D. W., and Buccafusco, J. J. (2007). Chronic, intermittent exposure to chlorpyrifos in rats: Protracted effects on axonal transport, neurotrophin receptors, cholinergic markers, and information processing. J. Pharmacol. Exp. Ther. 322, 1117-1128.
    • Terry, A. V., Jr., Gearhart, D. A., Beck, W. D., Jr., Truan, J. N., Middlemore, M. L., Williamson, L. N., Bartlett, M. G., Prendergast, M. A., Sickles, D. W., and Buccafusco, J. J. (2007). Chronic, intermittent exposure to chlorpyrifos in rats: Protracted effects on axonal transport, neurotrophin receptors, cholinergic markers, and information processing. J. Pharmacol. Exp. Ther. 322, 1117-1128.
  • 35
    • 5344245964 scopus 로고    scopus 로고
    • Retrospective detection of exposure to nerve agents: Analysis of phosphofluoridates originating from fluoride-induced reactivation of phosphorylated BuChE
    • Van Der Schans, M. J., Polhuijs, M., Van Dijk, C., Degenhardt, C. E., Pleijsier, K., Langenberg, J. P., and Benschop, H. P. (2004). Retrospective detection of exposure to nerve agents: Analysis of phosphofluoridates originating from fluoride-induced reactivation of phosphorylated BuChE. Arch. Toxicol. 78, 508-524.
    • (2004) Arch. Toxicol , vol.78 , pp. 508-524
    • Van Der Schans, M.J.1    Polhuijs, M.2    Van Dijk, C.3    Degenhardt, C.E.4    Pleijsier, K.5    Langenberg, J.P.6    Benschop, H.P.7
  • 36
    • 33747641642 scopus 로고    scopus 로고
    • The crystal structure of iron-free human serum transferrin provides insight into inter-lobe communication and receptor binding
    • Wally, J., Halbrooks, P. J., Vonrhein, C., Rould, M. A., Everse, S. J., Mason, A. B., and Buchanan, S. K. (2006). The crystal structure of iron-free human serum transferrin provides insight into inter-lobe communication and receptor binding. J. Biol. Chem. 281, 24934-24944.
    • (2006) J. Biol. Chem , vol.281 , pp. 24934-24944
    • Wally, J.1    Halbrooks, P.J.2    Vonrhein, C.3    Rould, M.A.4    Everse, S.J.5    Mason, A.B.6    Buchanan, S.K.7
  • 37
    • 0024369232 scopus 로고
    • A comparison of the structure and properties of human, rat and rabbit senim transferrin
    • Welch, S., and Skinner, A. (1989). A comparison of the structure and properties of human, rat and rabbit senim transferrin. Comp. Biochem. Physiol. B 93, 417-424.
    • (1989) Comp. Biochem. Physiol. B , vol.93 , pp. 417-424
    • Welch, S.1    Skinner, A.2
  • 38
    • 34547800796 scopus 로고    scopus 로고
    • Phosphorylated tyrosine in albumin as a biomarker of exposure to organophosphorus nerve agents
    • Williams, N. H., Harrison, J. M., Read, R. W., and Black, R. M. (2007). Phosphorylated tyrosine in albumin as a biomarker of exposure to organophosphorus nerve agents. Arch. Toxicol. 81, 627-639.
    • (2007) Arch. Toxicol , vol.81 , pp. 627-639
    • Williams, N.H.1    Harrison, J.M.2    Read, R.W.3    Black, R.M.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.