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

Chemico-Biological Interactions

Volumn 175, Issue 1-3, 2008, Pages 180-186

  Grigoryan, Hasmik ^a   Schopfer, Lawrence M ^a   Thompson, Charles M ^b   Terry, Alvin V ^c   Masson, Patrick ^d   Lockridge, Oksana ^a  

^a UNIVERSITY OF NEBRASKA MEDICAL CENTER   (United States)

^b UNIVERSITY OF MONTANA   (United States)

^c MEDICAL COLLEGE OF GEORGIA   (United States)

^d CENTRE DE RECHERCHES   (France)

Author keywords

Mass spectrometer; Nerve agent; Organophosphate; Tubulin; Tyrosine

Indexed keywords

10 FLUOROETHOXYPHOSPHINYL N BIOTINAMIDOPENTYLDECANAMIDE; BIOTIN DERIVATIVE; CHLORPYRIFOS OXON; DYFLOS; NERVE GAS; ORGANOPHOSPHORUS COMPOUND; SARIN; SOMAN; TUBULIN; TYROSINE; UNCLASSIFIED DRUG;

ARTICLE; BINDING SITE; CATTLE; CHRONIC TOXICITY; COGNITIVE DEFECT; CRYSTAL STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETER; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; MICROTUBULE; NEUROTOXICITY; NONHUMAN; NUCLEOTIDE SEQUENCE; PEPTIDE ANALYSIS; POLYMERIZATION; PROTEIN BINDING;

BINDING SITES; BIOTIN; CHLORPYRIFOS; CHOLINESTERASE INHIBITORS; ISOFLUROPHATE; ORGANOPHOSPHORUS COMPOUNDS; SARIN; SOMAN; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION; TUBULIN; TYROSINE;

BOVINAE; RATTUS;

EID: 50649103273     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cbi.2008.04.013     Document Type: Article

References (21)

1. Maxwell D.M., Brecht K.M., Koplovitz I., and Sweeney R.I. Acetylcholinesterase inhibition: does it explain the toxicity of organophosphorus compounds?. Arch. Toxicol. 80 (2006) 756-760
2. Roldan-Tapia L., Parron T., and Sanchez-Santed F. Neuropsychological effects of long-term exposure to organophosphate pesticides. Neurotoxicol. Teratol. 27 (2005) 259-266
3. Stephens R., Spurgeon A., Calvert I.A., Beach J., Levy L.S., Berry H., and Harrington J.M. Neuropsychological effects of long-term exposure to organophosphates in sheep dip. Lancet 345 (1995) 1135-1139
4. London L., Flisher A.J., Wesseling C., Mergler D., and Kromhout H. Suicide and exposure to organophosphate insecticides: cause or effect?. Am. J. Ind. Med. 47 (2005) 308-321
5. Terry Jr. A.V., Gearhart D.A., Beck Jr. W.D., Truan J.N., Middlemore M.L., Williamson L.N., Bartlett M.G., Prendergast M.A., Sickles D.W., and Buccafusco J.J. Chronic, intermittent exposure to chlorpyrifos in rats: protracted effects on axonal transport, neurotrophin receptors, cholinergic markers, and information processing. J. Pharmacol. Exp. Ther. 322 (2007) 1117-1128
6. Terry Jr. A.V., Stone J.D., Buccafusco J.J., Sickles D.W., Sood A., and Prendergast M.A. Repeated exposures to subthreshold doses of chlorpyrifos in rats: hippocampal damage, impaired axonal transport, and deficits in spatial learning. J. Pharmacol. Exp. Ther. 305 (2003) 375-384
7. Gearhart D.A., Sickles D.W., Buccafusco J.J., Prendergast M.A., and Terry Jr. A.V. Chlorpyrifos, chlorpyrifos-oxon, and diisopropylfluorophosphate inhibit kinesin-dependent microtubule motility. Toxicol. Appl. Pharmacol. 218 (2007) 20-29
8. Prendergast M.A., Self R.L., Smith K.J., Ghayoumi L., Mullins M.M., Butler T.R., Buccafusco J.J., Gearhart D.A., and Terry Jr. A.V. Microtubule-associated targets in chlorpyrifos oxon hippocampal neurotoxicity. Neuroscience 146 (2007) 330-339
9. Schopfer L.M., Champion M.M., Tamblyn N., Thompson C.M., and Lockridge O. Characteristic mass spectral fragments of the organophosphorus agent FP-biotin and FP-biotinylated peptides from trypsin and bovine albumin (Tyr410). Anal. Biochem. 345 (2005) 122-132
10. Lowe J., Li H., Downing K.H., and Nogales E. Refined structure of alpha beta-tubulin at 3.5 A resolution. J. Mol. Biol. 313 (2001) 1045-1057
11. Nogales E., Wolf S.G., and Downing K.H. Structure of the alpha beta tubulin dimer by electron crystallography. Nature 391 (1998) 199-203
12. Fidder A., Hulst A.G., Noort D., de Ruiter R., van der Schans M.J., Benschop H.P., and Langenberg J.P. Retrospective detection of exposure to organophosphorus anti-cholinesterases: mass spectrometric analysis of phosphylated human butyrylcholinesterase. Chem. Res. Toxicol. 15 (2002) 582-590
13. Michel H.O., Hackley Jr. B.E., Berkowitz L., List G., Hackley E.B., Gillilan W., and Pankau M. Ageing and dealkylation of Soman (pinacolylmethylphosphonofluoridate)-inactivated eel cholinesterase. Arch. Biochem. Biophys. 121 (1967) 29-34
14. Millard C.B., Kryger G., Ordentlich A., Greenblatt H.M., Harel M., Raves M.L., Segall Y., Barak D., Shafferman A., Silman I., and Sussman J.L. Crystal structures of aged phosphonylated acetylcholinesterase: nerve agent reaction products at the atomic level. Biochemistry 38 (1999) 7032-7039
15. Nachon F., Asojo O.A., Borgstahl G.E., Masson P., and Lockridge O. Role of water in aging of human butyrylcholinesterase inhibited by echothiophate: the crystal structure suggests two alternative mechanisms of aging. Biochemistry 44 (2005) 1154-1162
16. Li B., Schopfer L.M., Hinrichs S.H., Masson P., and Lockridge O. Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry assay for organophosphorus toxicants bound to human albumin at Tyr411. Anal. Biochem. 361 (2007) 263-272
17. Means G.E., and Wu H.L. The reactive tyrosine residue of human serum albumin: characterization of its reaction with diisopropylfluorophosphate. Arch. Biochem. Biophys. 194 (1979) 526-530
18. Williams N.H., Harrison J.M., Read R.W., and Black R.M. Phosphylated tyrosine in albumin as a biomarker of exposure to organophosphorus nerve agents. Arch. Toxicol. 81 (2007) 627-639
19. Li B., Nachon F., Froment M.-T., Verdier L., Debouzy J.-C., Gillon E., Brasme B., Schopfer L., Lockridge O., and Masson P. Binding and hydrolysis of soman by human serum albumin. Chem. Res. Toxicol. 21 (2008) 421-431
20. Chaiken I.M., and Smith E.L. Reaction of a specific tyrosine residue of papain with diisopropylfluorophosphate. J. Biol. Chem. 244 (1969) 4247-4250
21. Murachi T., Inagami T., and Yasui M. Evidence for alkylphosphorylation of tyrosyl residues of stem bromelain by diisopropylphosphorofluoridate. Biochemistry 4 (1965) 2815-2825