Organophosphate Toxicology: Safety Aspects of Nonacetylcholinesterase Secondary Targets

Chemical Research in Toxicology - Tập 17 Số 8 - Trang 983-998 - 2004
John E. Casida1, Gary B. Quistad1
1Environmental Chemistry and Toxicology Laboratory, Department of Environmental Science, Policy and Management, University of California, Berkeley, California, 94720-3112

Tóm tắt

Từ khóa


Tài liệu tham khảo

Tomlin C., 2003, The Pesticide Manual, 13

Eto M., 1974, Organophosphorus Pesticides:  Organic and Biological Chemistry, 387 pp

Ware G. W., 2000, The Pesticide Book, 5

Nauen R., 2002, New modes of action of insecticides. Pestic. Outlook 13, 241−245

Barr D. B., 2004, Concentrations of dialkyl phosphate metabolites of organophosphorus pesticides in the U.S. population. Environ. Health Perspect. 112, 186−200

Taylor P., 2001, Goodman & Gilman's The Pharmacological Basis of Therapeutics, 10, 191

Marrs T. C., 1996, Chemical Warfare Agents:  Toxicology and Treatment, 243 pp

Karczmar A., 1998, Int. 32, 401−411.

Holmstedt B., 1963, Cholinesterases and Anticholinesterase Agents (Koelle, G. B., Sub-Ed.), 485

Gallo M. A., 1991, Handbook of Pesticide Toxicology, 2, 1123

Lotti M., 2000, Experimental and Clinical Neurotoxicology, 2, 925

Pope C. N., 1999, J. Toxicol. Environ. Health, Part B, 2

Ray D. E., 2001, Toxicol. Lett., 120

Savolainen K., 2001, Handbook of Pesticide Toxicology, 2, 1041, 10.1016/B978-012426260-7.50053-7

Rachinsky T. L., 1990, Molecular cloning of mouse acetylcholinesterase:  tissue distribution of alternatively spliced mRNA species. Neuron 5, 317−327

Bourne Y., 1999, J. Biol. Chem., 274

Lockridge O., 1987, J. Biol. Chem., 262

Nicolet Y., 2003, J. Biol. Chem., 278, 10.1074/jbc.M210241200

Lush M. J., 1998, Biochem. J., 332, 4

Cravatt B. F., 1996, Nature, 384, 87, 10.1038/384083a0

Bracey M. H., 2002, Structural adaptations in a membrane enzyme that terminates endocannabinoid signaling. Science 298, 1793−1796

Abood M. E., 1997, Isolation and expression of a mouse CB1 cannabinoid receptor gene. Biochem. Pharmacol. 53, 207−214

Pabarcus M. K., 2002, Biochim. Biophys. Acta, 1596, 10.1016/S0167-4838(02)00232-7

Miyagi M., 1995, J. Biochem. (Tokyo), 118, 10.1093/oxfordjournals.jbchem.a124979

Greenspan R. J., 1980, J. Comp. Neurol., 189, 10.1002/cne.901890409

Kretzschmar D., 1997, J. Neurosci., 17, 10.1523/JNEUROSCI.17-19-07425.1997

Xie W., 2000, J. Pharmacol. Exp. Ther., 293

Winrow C. J., 2003, Loss of neuropathy target esterase in mice links organophosphate exposure to hyperactivity. Nat. Genet. 33, 477−485

Moser M., 2004, Placental failure and impaired vasculogenesis result in embryonic lethality for neuropathy target esterase-deficient mice. Mol. Cell. Biol. 24, 1667−1679

Akassoglou K., 2004, Proc. Natl. Acad. Sci. U.S.A. 101

Cravatt B. F., 2001, Proc. Natl. Acad. Sci. U.S.A. 98

Zimmer A., 1999, Proc. Natl. Acad. Sci. U.S.A. 96

Rubin G. M., 2000, Comparative genomics of eukaryotes. Science 287, 2204−2215

Quistad G. B., 2001, Toxicol. Appl. Pharmacol., 173, 55, 10.1006/taap.2001.9175

Quistad G. B., 2002, Toxicol. Appl. Pharmacol., 179, 63, 10.1006/taap.2001.9342

Quistad G. B., 2003, Proc. Natl. Acad. Sci. U.S.A. 100

Segall Y., 2003, Bioorg. Med. Chem. Lett., 13, 10.1016/S0960-894X(03)00721-2

Quistad G. B., 2002, Toxicol. Lett., 135, 93, 10.1016/S0378-4274(02)00251-5

Segall Y., 2003, Toxicological and structural features of organophosphorus and organosulfur cannabinoid CB1 receptor ligands. Toxicol. Sci. 76, 131−137

Segall, Y., Quistad, G. B., and Casida, J. E. (2003) Cannabinoid CB1 receptor chemical affinity probes:  methods suitable for preparation of isopropyl [11,12-3H]dodecylfluorophosphonate and [11,12-3H]dodecanesulfonyl fluoride.Synth. Commun.33, 2151−2159.

Menge U., 1979, Formamidase-untersuchungen zu mikroheterogenität, katalytischen eigenschaften und inhibitoren. Hoppe-Seyler's Z. Physiol. Chem. 360, 185−196

Richards P. G., 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

Aldridge W. N., 1972, Enzyme Inhibitors as Substrates:  Interactions of Esterases with Esters of Organophosphorus and Carbamic Acids, 328 pp

Jennings L. L., 2003, Direct analysis of the kinetic profiles of organophosphate-acetylcholinesterase adducts by MALDI-TOF mass spectrometry. Biochemistry 42, 11083−11091

Kropp T. J., 2004, Abstract 1097

Quistad, G. B., Zhang, N., Sparks, S. E., and Casida, J. E. (2000) Phosphoacetylcholinesterase:  toxicity of phosphorus oxychloride to mammals and insects that can be attributed to selective phosphorylation of acetylcholinesterase by phosphorodichloridic acid.Chem. Res. Toxicol.13, 652−657.

Segall Y., 2003, POCl3, PSCl3, and their diethyl esters) are anticholinesterase agents directly or on activation. Chem. Res. Toxicol. 16, 350−356.

Haux J. E., 2002, Specificity of ethephon as a butyrylcholinesterase inhibitor and phosphorylating agent. Chem. Res. Toxicol. 15, 1527−1533

Haux J. E., 2000, Phosphobutyrylcholinesterase:  phosphorylation of the esteratic site of butyrylcholinesterase by ethephon [(2-chloroethyl)phosphonic acid] dianion. Chem. Res. Toxicol. 13, 646−651

Masson P., 1997, Biochem. J., 327, 10.1042/bj3270601

Kropp T. J., 2004, The mipafox-inhibited catalytic domain of human neuropathy target esterase ages by reversible proton loss. Biochemistry 43, 3716−3722

Wing K. D., 1983, Science, 219, 65, 10.1126/science.6849117

Doorn, J. A., Thompson, C. M., Christner, R. B., and Richardson, R. J. (2003) Stereoselective inactivation ofTorpedo californicaacetylcholinesterase by isomalathion:  inhibitory reactions with (1R)- and (1S)-isomers proceed by different mechanisms.Chem. Res. Toxicol.16, 958−965.

Kuhr R. J., 1976, Carbamate Insecticides:  Chemistry, Biochemistry, and Toxicology, 301 pp

Brown J. H., 2001, Goodman and Gilman's The Pharmacological Basis of Therapeutics, 10, 173

O'Brien R. D., 1967, Insecticides:  Action and Metabolism, 332 pp

He F., 2000, Neurotoxic effects of insecticidescurrent and future research:  A review. Neurotoxicology 21, 829−836

Duysen E. G., 2002, Dev. Brain Res., 137, 54, 10.1016/S0165-3806(02)00367-X

Duysen E. G., 2001, J. Pharmacol. Exp. Ther., 299

Li B., 2003, Biochem. Behav. 74, 977−986.

Yagle K., 1996, Effects of organophosphate exposure on muscarinic acetylcholine receptor subtype mRNA levels in the adult rat. Neurotoxicology 17, 523−530

Bernard V., 2003, Dramatic depletion of cell surface m2 muscarinic receptor due to limited delivery from intracytoplasmic stores in neurons of acetylcholinesterase-deficient mice. Mol. Cell. Neurosci. 23, 121−133

Decossas M., 2003, J. Comp. Neurol., 462, 10.1002/cne.10734

Volpicelli-Daley L. A., 2003, Altered hippocampal muscarinic receptors in acetylcholinesterase-deficient mice. Ann. Neurol. 53, 788−796

Volpicelli-Daley L. A., 2003, Altered striatal function and muscarinic cholinergic receptors in acetylcholinesterase knockout mice. Mol. Pharmacol. 64, 1309−1316

Li B., 2000, J. Neurochem., 75

Mesulam M.-M., 2002, Acetylcholinesterase knockouts establish central cholinergic pathways and can use butyrylcholinesterase to hydrolyze acetylcholine. Neuroscience 110, 627−639

Minic J., 2003, Br. J. Pharmacol., 138, 10.1038/sj.bjp.0705010

Chatonnet F., 2003, Eur. J. Neurosci., 18, 10.1046/j.1460-9568.2003.02867.x

Behra M., 2004, The use of zebrafish mutants to identify secondary target effects of acetylcholine esterase inhibitors. Toxicol. Sci. 77, 325−333

Sparks S. E., 1999, J. Biochem. Mol. Toxicol., 13, 10.1002/(SICI)1099-0461(1999)13:2<113::AID-JBT7>3.0.CO;2-8

Herschman Z., 1991, Prolongation of cocaine effect. Anesthesiology 74, 631−632

Hoffman R. S., 1992, J. Pharmacol. Exp. Ther., 263

Broomfield C. A., 1991, J. Pharmacol. Exp. Ther., 259

Duysen E. G., 2002, J. Pharmacol. Exp. Ther., 302, 10.1124/jpet.102.033746

Zhan C.-G., 2003, J. Am. Chem. Soc., 125

Sun H., 2002, J. Pharmacol. Exp. Ther., 302

Gomeza J., 1999, Proc. Natl. Acad. Sci. U.S.A. 96

Silveira C. L. P., 1990, Putative M2 muscarinic receptors of rat heart have high affinity 995 for organophosphorus anticholinesterases. Toxicol. Appl. Pharmacol. 103, 474−481

Jett D. A., 1991, High-affinity activation by paraoxon of a muscarinic receptor subtype in rat brain striatum. Pestic. Biochem. Physiol. 39, 149−157

Ward T. R., 1996, Brain Res. Bull., 39, 55

Huff R. A., 1994, J. Pharmacol. Exp. Ther., 269

Olivier K., Jr., 2001, J. Biochem. Mol. Toxicol., 15

Ward T. R., 1993, Correlation of the anticholinesterase activity of a series of organophosphates with their ability to compete with agonist binding to muscarinic receptors. Toxicol. Appl. Pharmacol. 122, 300−307

Liu J., 2002, vitro effects of organophosphorus anticholinesterases on muscarinic receptor-mediated inhibition of acetylcholine release in rat striatum. Toxicol. Appl. Pharmacol. 178, 102−108

Howard M. D., 2002, Toxicology, 170, 10, 10.1016/S0300-483X(01)00498-X

Katz L. S., 1992, Organophosphate-induced alterations in muscarinic receptor binding and phosphoinositide hydrolysis in the human SK-N-SH cell line. Neurotoxicology 13, 365−378

Ehrich M., 1994, J. Toxicol. Environ. Health, 43, 63, 10.1080/15287399409531903

Bomser J. A., 2001, Toxicol. Lett., 119, 26, 10.1016/S0378-4274(00)00294-0

Huff R. A., 2001, Effects of sub-chronic in vivo chlorpyrifos exposure on muscarinic receptors and adenylate cyclase of rat striatum. Arch. Toxicol. 75, 480−486

Betancourt A., 2004, Toxicol. Sci., 77, 71

Auman J. T., 2000, Dev. Brain Res., 121, 27, 10.1016/S0165-3806(00)00021-3

Song X., 1997, Cellular mechanisms for developmental toxicity of chlorpyrifos:  targeting the adenylyl cyclase signaling cascade. Toxicol. Appl. Pharmacol. 145, 158−174

Meyer A., 2003, Developmental neurotoxicity elicited by gestational exposure to chlorpyrifos:  when is adenylyl cyclase a target? Environ. Health Perspect. 111

Fryer A. D., 2004, Am. J. Physiol. Lung Cell. Mol. Physiol., 286, 10.1152/ajplung.00343.2003

Chaudhuri J., 1993, J. Biochem. Toxicol., 8, 10.1002/jbt.2570080406

Zhang H., 2002, Age-related effects of chlorpyrifos on muscarinic receptor-mediated signaling in rat cortex. Arch. Toxicol. 75, 676−684

Costa L. G., 1982, Differential alterations of cholinergic muscarinic receptors during chronic and acute tolerance to organophosphorus insecticides. Biochem. Pharmacol. 31, 3407−3413

Tang J., 2003, The effects of repeated oral exposures to methyl parathion on rat brain cholinesterase and muscarinic receptors during postnatal development. Toxicol. Sci. 76, 400−406

Slotkin T. A., 2001, Persistent cholinergic presynaptic deficits after neonatal chlorpyrifos exposure. Brain Res. 902, 229−243

Qiao, D., Seidler, F. J., Tate, C. A., Cousins, M. M., and Slotkin, T. A. (2003) Fetal chlorpyrifos exposure:  adverse effects on brain cell development and cholinergic biomarkers emerge postnatally and continue into adolescence and adulthood.Environ. Health Perspect.111, 536−544.

Richardson J. R., 2003, J. Toxicol. Environ. Health, Part A, 66, 10.1080/15287390306369

Qiao D., 2004, Dev. Brain Res., 148, 52, 10.1016/j.devbrainres.2003.10.004

Liu J., 1996, Fundam. Appl. Toxicol., 34, 90

Liu J., 1998, J. Toxicol. Environ. Health, Part A, 53

Mattio T. G., 1985, Acute effects of cholinesterase inhibitors on uptake of choline in the rat iris. Pharmacology 24, 325−328

Kaufer D., 1999, Anticholinesterases induce multigenic transcriptional feedback response suppressing cholinergic neurotransmission. Chem.-Biol. Interact. 119−120, 349−360

Karanth S., 2003, Age-related effects of chlorpyrifos and parathion on acetylcholine synthesis in rat striatum. Neurotoxicol. Teratol. 25, 599−606

Wu Y.-J., 2003, Nicotinic autoreceptor function in rat brain during maturation and aging:  possible differential sensitivity to organophosphorus anticholinesterases. Chem.-Biol. Interact. 142, 255−268

Katz E. J., 1997, Chlorpyrifos, parathion, and their oxons bind to and desensitize a nicotinic acetylcholine receptor:  relevance to their toxicities. Toxicol. Appl. Pharmacol. 146, 227−236

Johnson M. K., 1975, Organophosphorus esters causing delayed neurotoxic effects:  mechanism of action and structure/activity studies. Arch. Toxicol. 34, 259−288, 10.1007/BF00353848

Smith M. I., 1930, The pharmacological action of certain phenol esters with special reference to the etiology of so-called ginger paralysis. U.S. Publ. Health Rep. 45, 2509−2524

Smith H. V., 1959, Outbreak of paralysis in Morocco due to ortho-cresyl phosphate poisoning. Lancet II, 1019−1021

Ehrich M., 2001, Handbook of Pesticide Toxicology, 2, 2, 1012

Winder, C., and Balouet, J.C. (2002) The toxicity of commercial jet oils.Environ. Res. Sect. A89, 146−164.

Casida J. E., 1961, Biological activity of a tri-o-cresyl phosphate metabolite. Nature 191, 1396−1397

Eto M., 1962, Hydroxylation and cyclization reactions involved in the metabolism of tri-o-cresyl phosphate. Biochem. Pharmacol. 11, 337−352

Eto M., 1967, Plasma albumin as a catalyst in cyclization of diaryl o-(α-hydroxy)tolyl phosphates. Biochem. Pharmacol. 16, 295−308

Johnson M. K., 2001, Handbook of Pesticide Toxicology, 2, 2, 965

Wu S. Y., 1996, Subacute neurotoxicity induced in mice by potent organophosphorus neuropathy target esterase inhibitors. Toxicol. Appl. Pharmacol. 139, 195−202

Johnson M. K., 1977, Improved assay of neurotoxic esterase for screening organophosphates for delayed neurotoxicity potential. Arch. Toxicol. 37, 113−115

Johnson M. K., 1969, Biochem. J., 111, 10.1042/bj1110487

Atkins J., 2000, J. Biol. Chem., 275

van Tienhoven M., 2002, J. Biol. Chem., 277, 10.1074/jbc.M200330200

Xie, M., Yang, D., Matoney, L., and Yan, B. (2003) Rat NTE-related esterase is a membrane-associated protein, hydrolyzes phenyl valerate, and interacts with diisopropylfluorophosphate through a serine catalytic machinery.Arch. Biochem. Biophys.416, 137−146.

Li Y., 2003, J. Biol. Chem., 278

Zaccheo O., 2004, J. Biol. Chem., 279, 10.1074/jbc.M400830200

Wang A., 1999, Biochim. Biophys. Acta, 1439, 16

Xu Y., 2002, Biochim. Biophys. Acta, 1582, 88

Kabarowski J. H. S., 2002, Lysophosphatidylcholine as a ligand for immunoregulation. Biochem. Pharmacol. 64, 161−167

Quistad G. B., 2004, Lysophospholipase inhibition by organophosphorus toxicants. Toxicol. Appl. Pharmacol. 196, 319−326

Wang A., 1997, J. Biol. Chem., 272

Wang A., 1999, Biochim. Biophys. Acta, 1437

El-Sebae A. H., 1977, J. Environ. Sci. Health B, 12

Richardson R. J., 1995, J. Toxicol. Environ. Health, 44, 10.1080/15287399509531952

Glynn P., 2000, Prog. Neurobiol., 61, 74, 10.1016/S0301-0082(99)00043-X

Tahmaz N., 2003, Chronic fatigue and organophosphate pesticides in sheep farming:  a retrospective study amongst people reporting to a UK pharmacovigilance scheme. Ann. Occup. Hyg. 47, 261−267

Institute of Medicine, 2000, Gulf War and Health, 1

Lotti M., 2002, Low-level exposures to organophosphorus esters and peripheral nerve function. Muscle Nerve 25, 492−504

Fukuto T. R., 1983, J. Environ. Sci. Health B, 18, 117, 10.1080/03601238309372359

Rodgers K. E., 1995, Handbook of Pesticide Toxicology, 1, 2, 782

Aldridge W. N., 1985, S47−S60.

Bomser J., 2000, J. Biochem. Mol. Toxicol., 14, 10.1002/1099-0461(2000)14:6<346::AID-JBT7>3.0.CO;2-H

Bomser J. A., 2002, Toxicol. Appl. Pharmacol., 178, 36, 10.1006/taap.2001.9324

Caughlan, A., Newhouse, K., Namgung, U., and Xia, Z. (2004) Chlorpyrifos induces apoptosis in rat cortical neurons that is regulated by a balance between p38 and ERK/JNK MAP kinases.Toxicol. Sci. 78, 125−134.

Lin W.-W., 1999, Br. J. Pharmacol., 126

Kaufer D., 1999, Anticholinesterases induce multigenic transcriptional feedback response suppressing cholinergic neurotransmission. Chem.-Biol. Interact. 119−120, 349−360

Bagchi D., 1997, Toxicol. Lett., 91, 37, 10.1016/S0378-4274(97)03868-X

Lanning C. L., 1996, J. Toxicol. Environ. Health, 47, 10.1080/009841096161726

Fox J. H., 2003, J. Biochem. Mol. Toxicol., 17

Damodaran T. V., 2002, Sarin causes altered time course of mRNA expression of alpha tubulin in the central nervous system of rats. Neurochem. Res. 27, 177−181

Damodaran, T. V., Bilska, M. A., Rahman, A. A., and Abou-Donia, M. B. (2002) Sarin causes early differential alteration and persistent overexpression in mRNAs coding for glial fibrillary acidic protein (GFAP) and vimentin genes in the central nervous system of rats.Neurochem. Res.27, 407−415.

Sekowski J. W., 2003, Alternative Toxicological Methods

Deutsch D. G., 2002, Leukotrienes Essent. Fatty Acids 66, 201−210.

Deutsch D. G., 1997, Methyl arachidonyl fluorophosphonate:  a potent irreversible inhibitor of anandamide amidase. Biochem. Pharmacol. 53, 255−260

Martin B. R., 2000, J. Pharmacol. Exp. Ther., 294

Deutsch D. G., 1997, Fatty acid sulfonyl fluorides inhibit anandamide metabolism and bind to the cannabinoid receptor. Biochem. Biophys. Res. Commun. 231, 217−221

Roger J.-C., 1964, Nicotinic acid analogues:  effects on response of chick embryos and hens to organophosphate toxicants. Science 144, 539−540

Seifert J., 1981, Progress in Pesticide Biochemistry, 246

Roger J.-C., 1969, Structure−activity and metabolism studies on organophosphate teratogens and their alleviating agents in developing hen eggs with special emphasis on Bidrin. Biochem. Pharmacol. 18, 373−392

Proctor N. H., 1975, Organophosphorus and methyl carbamate insecticide teratogenesis:  diminished NAD in chicken embryos. Science 190, 580−582

Proctor N. H., 1976, Chicken embryo NAD levels lowered by teratogenic organophosphorus and methylcarbamate insecticides. Biochem. Pharmacol. 25, 757−762

Moscioni A. D., 1977, Kynurenine formamidase inhibition as a possible mechanism for certain teratogenic effects of organophosphorus and methylcarbamate insecticides in chicken embryos. Biochem. Pharmacol. 26, 2251−2258

Seifert, J., and Casida, J. E. (1978) Relation of yolk sac membrane kynurenine formamidase inhibition to certain teratogenic effects of organophosphorus insecticides and of carbaryl and eserine in chicken embryos.Biochem. Pharmacol. 27, 2611−2615.

Eto M., 1980, Toxicol. Appl. Pharmacol., 54, 30

Upshall D. G., 1968, Biochemical studies on the teratogenic action of Bidrin and other neuroactive agents in developing hen eggs. Biochem. Pharmacol. 17, 1529−1542

Seifert J., 1992, Alteration of mice L-tryptophan metabolism by the organophosphorous acid triester diazinon. Biochem. Pharmacol. 44, 2243−2250

Pewnim T., 1993, Eur. J. Pharmacol., 248

Schuettengruber B., 2003, J. Biol. Chem., 278, 10.1074/jbc.M204843200

Jones W. M., 1994, Acylaminoacyl-peptidase. Methods Enzymol. 244, 227−231

Fujino T., 2000, Biochim. Biophys. Acta, 1478, 10.1016/S0167-4838(00)00004-2

Liu Y., 1999, Proc. Natl. Acad. Sci. U.S.A. 96

Richards P. G., 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

Tsunasawa S., 1984, Amino-terminal acetylation of proteins:  an overview. Methods Enzymol. 106, 165−170

Satoh T., 1987, Reviews in Biochemical Toxicology

Casida J. E., 1983, Annu. Rev. Pharmacol. Toxicol., 23, 10.1146/annurev.pa.23.040183.002213

Ishaaya I., 1983, Pesticide Chemistry:  Human Welfare and the Environment, 310

Abernathy C. O., 1973, Substrate-specificity and toxicological significance of pyrethroid-hydrolyzing esterases of mouse liver microsomes. Pestic. Biochem. Physiol. 3, 300−311

Newcomb R. D., 1997, Proc. Natl. Acad. Sci. U.S.A. 94

Still G. G., 1976, Herbicides:  Chemistry, Degradation, and Mode of Action, 664

Maxwell D. M., 1992, The specificity of carboxylesterase protection against the toxicity of organophosphorus compounds. Toxicol. Appl. Pharmacol. 114, 306−312

Dettbarn W.-D., 1999, Different role of carboxylesterases in toxicity and tolerance to paraoxon and DFP. Chem.-Biol. Interact. 119−120, 445−454

Maxwell D. M., 2001, J. Appl. Toxicol., 21, 10.1002/jat.833

Jokanovic M., 1996, Interaction of organophosphorus compounds with carboxylesterases in the rat. Arch. Toxicol. 70, 444−450

Satoh T., 1973, A liver arylamidase extremely sensitive to organophosphorus compounds. Life Sci. 13, 1181−1188

March R. B., 1956, J. Econ. Entomol., 49

Casida J. E., 1956, J. Agric. Food Chem., 4

Mahajna M., 1997, Chem. Res. Toxicol., 10, 69, 10.1021/tx9601420

Casida J. E., 1963, Biochem. Pharmacol., 12, 83, 10.1016/0006-2952(63)90011-X

Richards P., 1999, Novel protein targets for organophosphorus compounds. Chem.-Biol. Interact. 119−120, 503−511

Richards P., 2002, Functional proteomics using microchannel plate detectors. Proteomics 2, 256−261

Sato T., 1997, J. Biol. Chem., 272

Kidd D., 2001, Profiling serine hydrolase activities in complex proteomes. Biochemistry 40, 4005−4015

Liu Y., 1999, Proc. Natl. Acad. Sci. U.S.A. 96

Glynn P., 1994, Biochem. J., 301, 10.1042/bj3010551

Keshavarz-Shokri A., 1999, Identification of serine esterases in tissue homogenates. Anal. Biochem. 267, 406−411

Snawder J. E., 1993, Osteolathyrogenic effects of malathion in Xenopus embryos. Toxicol. Appl. Pharmacol. 121, 210−216

Schuh R. 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

Saleh A. M., 2003, Toxicol. Appl. Pharmacol., 190, 57, 10.1016/S0041-008X(03)00126-1

Kell P. J., 2003, J. Pharmacol. Exp. Ther., 307

Hattori M., 1993, J. Biol. Chem., 268

Tamura H., 2003, Interaction of organophosphate pesticides and related compounds with the androgen receptor. Environ. Health Perspect. 111, 545−552

Tamura H., 2001, Toxicol. Sci., 60, 62, 10.1093/toxsci/60.1.56

Barber D., 2001, J. Toxicol. Environ. Health, Part A, 63, 10.1080/15287390151126423

Blasiak J., 1995, Cooperative binding of the organophosphate paraoxon to the (Na+ + K+)-ATPase. Z. Naturforsch. 50, 660−663

Pruett S. B., 1994, J. Biochem. Toxicol., 9, 10.1002/jbt.2570090607

Quistad G. B., 2000, J. Biochem. Mol. Toxicol., 14, 56, 10.1002/(SICI)1099-0461(2000)14:1<51::AID-JBT7>3.0.CO;2-W

Crumpton T. L., 2000, Is oxidative stress involved in the developmental neurotoxicity of chlorpyrifos? Dev. Brain Res. 121, 189−195

Eastmond D. A., 2001, Handbook of Pesticide Toxicology, 1, 2, 767

Wright A. S., 1979, Arch. Toxicol., 42, 18

Qiao, D., Seidler, F. J., and Slotkin, T. A. (2001) Developmental neurotoxicity of chlorpyrifos modeled in vitro:  comparative effects of metabolites and other cholinesterase inhibitors on DNA synthesis in PC12 and C6 cells.Environ. Health Perspect.109, 909−913.

Das K. P., 1999, Neuronal differentiation in PC12 cells is inhibited by chlorpyrifos and its metabolites:  is acetylcholinesterase inhibition the site of action? Toxicol. Appl. Pharmacol. 160, 217−230

Li W., 1998, Toxicol. Lett., 98

Massicotte C., 2003, Morphological effects of neuropathy-inducing organophosphorus compounds in primary dorsal root ganglia cell cultures. Neurotoxicology 24, 787−796

Hong M. S., 2003, Neurotoxicity induced in differentiated SK-N-SH-SY5Y human neuroblastoma cells by organophosphorus compounds. Toxicol. Appl. Pharmacol. 186, 110−118

Carlson K., 1999, Toxicol. Appl. Pharmacol., 160, 42, 10.1006/taap.1999.8741

Johnson P. S., 1991, Characterization of organophosphate interactions at N-methyl-D-aspartate receptors in brain synaptic membranes. Mol. Pharmacol. 41, 750−756

Li, Q., Nagahara, N., Takahashi, H., Takeda, K., Okumura, K., and Minami, M. (2002) Organophosphorus pesticides markedly inhibit the activities of natural killer, cytotoxic T lymphocyte and lymphokine-activated killer:  a proposed inhibiting mechanism via granzyme inhibition.Toxicology172, 181−190.

Slotkin T. A., 2004, Cholinergic systems in brain development and disruption by neurotoxicants:  nicotine, environmental tobacco smoke, organophosphates. Toxicol. Appl. Pharmacol

Roy T. S., 1998, Teratology, 58, 68

Garcia S. J., 2003, Developmental neurotoxicity elicited by prenatal or postnatal chlorpyrifos exposure:  effects on neurospecific proteins indicate changing vulnerabilities. Environ. Health Perspect. 111, 297−303

Aldridge J. E., 2003, Serotonergic systems targeted by developmental exposure to chlorpyrifos:  effects during different critical periods. Environ. Health Perspect. 111, 1736−1743

Terry A. V., Jr., 2003, J. Pharmacol. Exp. Ther., 305

Jett D. A., 2000, vitro and in vivo effects of chlorpyrifos on glutathione peroxidase and catalase in developing rat brain. Neurotoxicology 21, 141−146

Whitney K. D., 1995, Toxicol. Appl. Pharmacol., 134, 62, 10.1006/taap.1995.1168

Gordon C. J., 1996, Pharmacological analysis of diisopropyl fluorophosphate:  effects on core temperature, heart rate, and motor activity in the unrestrained rat. Pharmacol. Biochem. Behav. 55, 185−194

Gupta, R. C., Milatovic, D., and Dettbarn, W.D. (2002) Involvement of nitric oxide in myotoxicity produced by diisopropylphosphorofluoridate (DFP)-induced muscle hyperactivity.Arch. Toxicol.76, 715−726.

Galloway T., 2003, Immunotoxicity of organophosphorous pesticides. Ecotoxicology 12, 345−363

Casida J. E., 1998, Rev. Entomol., 43, 16, 10.1146/annurev.ento.43.1.1

Krieger R. I., 2001, Handbook of Pesticide Toxicology, 1, 2

Krieger R. I., 2001, Handbook of Pesticide Toxicology, 2, 2

Mileson B. E., 1998, Toxicol. Sci., 41, 20

Abbreviations, acetylcholine