Protein Information

Name Acetylcholinesterase
Synonyms ACHE; ACHE protein; AChE; ARACHE; AcChoEase; Acetylcholine acetylhydrolase; Acetylcholinesterase; Acetylcholinesterase isoform E4 E6 variant…

Compound Information

Name methamidophos
CAS

Reference List

PubMed Abstract RScore(About this table)
7059283 de Jong LP, Wolring GZ, Benschop HP: Reactivation of acetylcholinesterase inhibited by methamidophos and analogous (di) methylphosphoramidates. Arch Toxicol. 1982 Jan;49(2):175-83.
405(5,5,5,5) Details
9477223 Mahajna M, Casida JE: Oxidative bioactivation of methamidophos insecticide: synthesis of N-hydroxymethamidophos (a candidate metabolite) and its proposed alternative reactions involving N--> O rearrangement or fragmentation through a metaphosphate analogue. Chem Res Toxicol. 1998 Jan;11(1):26-34.

The systemic insecticide methamidophos, MeO (MeS) P (O) NH2, is a very weak inhibitor of acetylcholinesterase (AChE) in vitro relative to in vivo suggesting bioactivation.
305(3,5,5,5) Details
1781739 Bertolazzi M, Caroldi S, Moretto A, Lotti M: Interaction of methamidophos with hen and human acetylcholinesterase and neuropathy target esterase. Arch Toxicol. 1991;65(7):580-5.
209(2,3,5,9) Details
3798464 Singh AK: Kinetic analysis of acetylcholinesterase inhibition by combinations of acephate and methamidophos. Toxicology. 1986 Dec 15;42(2-3):143-56.
386(4,6,6,6) Details
4060156 Singh AK: Kinetic analysis of inhibition of brain and red blood cell acetylcholinesterase and plasma cholinesterase by acephate or methamidophos. Toxicol Appl Pharmacol. 1985 Nov;81(2):302-9.

In this investigation of two insecticides, methamidophos was at least 75 to 100 times more potent an inhibitor of acetylcholinesterase (AChE) and cholinesterase (ChE) than was acephate.
146(1,3,3,6) Details
15522598 de Oliveira Marques PR, Nunes GS, dos Santos TC, Andreescu S, Marty JL: Comparative investigation between acetylcholinesterase obtained from commercial sources and genetically modified Drosophila melanogaster: application in amperometric biosensors for methamidophos pesticide detection. Biosens Bioelectron. 2004 Nov 1;20(4):825-32.
120(1,2,3,5) Details
14694584 Zhou L, Zhang Y, Shi N: [Comparison of the toxic effect of methamidophos and acephate on acetylcholinesterase]. Zhonghua Lao Dong Wei Sheng Zhi Ye Bing Za Zhi. 2002 Dec;20(6):405-8.

RESULTS: Acephate and methamidophos could directly inhibit AChE activities in human erythrocyte membrane and rat brain synatosomal membrane in dose- and time-dependent manners in vitro, and this effect was irreversible.
202(2,3,4,7) Details
2097819 Singh AK: Molecular properties and inhibition kinetics of acetylcholinesterase obtained from rat brain and cockroach ganglion. Toxicol Ind Health. 1990 Dec;6(6):551-70.

This study also indicated that the ED site in rat-AChE may be peripheral to the active site, and that the binding of acephate to this site prevented the phosphorylation by methamidophos of the rat-AChE.
201(2,3,3,11) Details
19132886 Zhou S, Zhang D, Yang H, Zhang Y, Liu W: Mechanisms of composition change and toxic potentiation of chloramidophos emulsifiable concentrate during storage. J Agric Food Chem. 2009 Feb 11;57(3):930-7.

Following redetermination of the main product (O,S-dimethyl-[(2,2,2)-trichloro-1-methoxyethyl] phosphoramidothioate (MCP)) and high anti-AChE material (methamidophos), which were preconfirmed in the reaction mixture in CP EC, it was successfully demonstrated that the majority of CP in the formulation had been transformed to a new stable compound, MCP.
34(0,1,1,4) Details
3240095 Langenberg JP, De Jong LP, Otto MF, Benschop HP: Spontaneous and oxime-induced reactivation of acetylcholinesterase inhibited by phosphoramidates. Arch Toxicol. 1988;62(4):305-10.

Methamidophos (CH3O (NH2) P (O) SCH3) and phosphoramidates, with the general structure RO (NH2) P (O) OC6H4-p-NO2, in which R = C2H5, C1CH2CH2, FCH2CH2 and F3CCH2, as well as (NH2) 2P (O) OC6H4-p-NO2 were synthesized to investigate the relationship between the rates of inhibition and of spontaneous reactivation of AChE inhibited by these organophosphates and their potential as prophylactics against nerve agent poisoning.
33(0,1,1,3) Details
1670382 Singh AK: Molecular properties and inhibition kinetics of acetylcholinesterase obtained from rat brain and cockroach ganglion. Toxicol Ind Health. 1990 Dec;6(6):551-70.

This study also indicated that the ED site in rat-AChE may be peripheral to the active site, and that the binding of acephate to this site prevented the phosphorylation by methamidophos of the rat-AChE.
201(2,3,3,11) Details
19371631 Bosgra S, van Eijkeren JC, van der Schans MJ, Langenberg JP, Slob W: Toxicodynamic analysis of the inhibition of isolated human acetylcholinesterase by combinations of methamidophos and methomyl in vitro. Toxicol Appl Pharmacol. 2009 Apr 1;236(1):1-8. Epub 2009 Jan 20.
164(2,2,2,4) Details
16563591 Caldas ED, Boon PE, Tressou J: Probabilistic assessment of the cumulative acute exposure to organophosphorus and carbamate insecticides in the Brazilian diet. Toxicology. 2006 May 1;222(1-2):132-42. Epub 2006 Mar 6.

The exposure to AChE inhibiting pesticides for the general population at P99.9, represented 33.6% of the ARfD as methamidophos and 70.2% ARfD as acephate.
114(1,2,2,4) Details
15464266 Di Angelantonio S, Bernardi G, Mercuri NB: Methamidophos transiently inhibits neuronal nicotinic receptors of rat substantia nigra dopaminergic neurons via open channel block. Neurosci Lett. 2004 Oct 21;369(3):208-13.

Our results conclude that methamidophos has a complex blocking action on neuronal nAChRs that is unlinked to the inhibition of AChE.
113(1,2,2,3) Details
7654138 Lotti M, Moretto A, Bertolazzi M, Peraica M, Fioroni F: Organophosphate polyneuropathy and neuropathy target esterase: studies with methamidophos and its resolved optical isomers. Arch Toxicol. 1995;69(5):330-6.

However, after L-(-) methamidophos (15 mg/kg PO), peak inhibition (80-90%) was obtained within 24 h for AChE, whereas similar NTE inhibition (120 mg/kg PO) was observed only 4 days after dosing.
112(1,2,2,2) Details
1660708 Johnson MK, Vilanova E, Read DJ: Anomalous biochemical responses in tests of the delayed neuropathic potential of methamidophos (O,S-dimethyl phosphorothioamidate), its resolved isomers and of some higher O-alkyl homologues. Arch Toxicol. 1991;65(8):618-24.

The interaction with neural neuropathy target esterase (NTE) and acetylcholinesterase (AChE) in vivo of methamidophos (O,S-dimethyl phosphorothioamidate), its resolved stereoisomers and five higher O-alkyl homologues has been examined along with the ability of these compounds to cause organophosphorus-induced delayed polyneuropathy (OPIDP) in adult hens.
32(0,1,1,2) Details
15207378 Battershill JM, Edwards PM, Johnson MK: Toxicological assessment of isomeric pesticides: a strategy for testing of chiral organophosphorus (OP) compounds for delayed polyneuropathy in a regulatory setting. Food Chem Toxicol. 2004 Aug;42(8):1279-85.

The combination of differential metabolism of chiral organophosphorus (OP) pesticides and opposing stereoselectivity of inhibition of neuropathy target esterase (NTE) and acetylcholinesterase (AChE) can affect the value of the hen test, performed to OECD guidelines, in predicting the potential to cause organophosphate-induced delayed polyneuropathy (OPIDP) in humans.
The experimental data on structural analogues of the pesticide methamidophos and the evidence for stereoselective OPIDP are reviewed and a model is given demonstrating how the properties of a chiral OP can result in the neuropathic potential not being detected by the standard hen test.
1(0,0,0,1) Details
2536970 Johnson MK, Vilanova E, Read DJ: Biochemical and clinical tests of the delayed neuropathic potential of some O-alkyl O-dichlorophenyl phosphoramidate analogues of methamidophos (O,S-dimethyl phosphorothioamidate). Toxicology. 1989 Jan;54(1):89-100.

The interaction in vivo of four O-alkyl O-2,5-dichlorophenyl phosphoramidates with neural neuropathy target esterase (NTE) and acetylcholinesterase (AChE) and their ability to cause delayed polyneuropathy in hens has been examined.
1(0,0,0,1) Details
17533655 Lin YW, Wu G, Miyata T: Insecticide susceptibility of surviving Cotesia plutellae (Hym: Braconidae) and Diaeretiella rapae (M'Intosh) (Hym: Aphidiidae) as affected by sublethal insecticide dosages on host insects. Pest Manag Sci. 2007 Sep;63(9):841-50.

The average AChE activity inhibition by methamidophos and dichlorvos in 34-60 adults of the two parasitoids that emerged from the treatments (15.1% and 31.8% respectively for C. plutellae, and 21.1% and 26.9% for D. rapae) was also significantly lower than those of the controls (55.4% and 48.3% respectively for C. plutellae, and 42.9% and 51.7% for D. rapae).
94(1,1,3,4) Details
11328714 Spassova DP, Singh AK: QSAR for acetylcholinesterase inhibition and toxicity of two classes of phosphoramidothioates. SAR QSAR Environ Res. 2001 Feb;11(5-6):453-71.

Methamidophos (Met) is a weak inhibitor of housefly head AChE but at the same time it is highly toxic to the common housefly.
88(1,1,1,8) Details
17382909 Worek F, Aurbek N, Koller M, Becker C, Eyer P, Thiermann H: Kinetic analysis of reactivation and aging of human acetylcholinesterase inhibited by different phosphoramidates. Biochem Pharmacol. 2007 Jun 1;73(11):1807-17. Epub 2007 Feb 16.

However, human AChE inhibited by certain OP, e.g. the phosphoramidates tabun and fenamiphos, is rather resistant towards reactivation by oximes while AChE inhibited by others, e.g. the phosphoramidate methamidophos is easily reactivated by oximes.
88(1,1,1,8) Details
12210959 Li F, Han Z: Purification and characterization of acetylcholinesterase from cotton aphid (Aphis gossypii Glover). Arch Insect Biochem Physiol. 2002 Sep;51(1):37-45.

The purified AChE was more sensitive to eserine, methamidophos, and pirimicarb.
20(0,0,2,10) Details
16249032 Garcia-de la Parra LM, Bautista-Covarrubias JC, Rivera-de la Rosa N, Betancourt-Lozano M, Guilhermino L: Effects of methamidophos on acetylcholinesterase activity, behavior, and feeding rate of the white shrimp (Litopenaeus vannamei). Ecotoxicol Environ Saf. 2006 Nov;65(3):372-80. Epub 2005 Oct 24.
19(0,0,3,4) Details
11453739 Elhanany E, Ordentlich A, Dgany O, Kaplan D, Segall Y, Barak R, Velan B, Shafferman A: Resolving pathways of interaction of covalent inhibitors with the active site of acetylcholinesterases: MALDI-TOF/MS analysis of various nerve agent phosphyl adducts. Chem Res Toxicol. 2001 Jul;14(7):912-8.

Here we describe experiments which allowed to resolve some of the less well understood reaction pathways of phosphylation and "aging" of acetylcholinesterase (AChE) involving phosphoroamidates (P-N agents) such as tabun or the widely used pesticide methamidophos.
17(0,0,2,7) Details
12039681 Singh AK: Acute effects of acephate and methamidophos and interleukin-1 on corticotropin-releasing factor (CRF) synthesis in and release from the hypothalamus in vitro. Comp Biochem Physiol C Toxicol Pharmacol. 2002 May;132(1):9-24.

Acute effects of Ace, Meth and IL-1 on AChE activity, ACh and CRF mRNA levels in, and CRF-release from the hypothalamus were studied in vitro.
1(0,0,0,1) Details
18290547 Pohanka M, Kuca K, Jun D: Amperometric biosensor for pesticide methamidophos assay. Acta Medica (Hradec Kralove). 2007;50(4):239-41.

The measuring principle was based on the inhibition of AChE activity in the presence of methamidophos.
88(1,1,2,3) Details
12449529 Kasagami T, Miyamoto T, Yamamoto I: Activated transformations of organophosphorus insecticides in the case of non-AChE inhibitory oxons. Pest Manag Sci. 2002 Nov;58(11):1107-17.

However, certain S-alkyl phosphorothiolates (RS-P (O) <) such as methamidophos, profenophos and prothiophos oxon are strongly insecticidal, but very poor inhibitors of AChE in vitro.
86(1,1,1,6) Details
11048668 Spassova D, White T, Singh AK: Acute effects of acephate and methamidophos on acetylcholinesterase activity, endocrine system and amino acid concentrations in rats. Comp Biochem Physiol C Toxicol Pharmacol. 2000 May;126(1):79-89.
14(0,0,2,4) Details
18569613 Rajini PS, Melstrom P, Williams PL: A comparative study on the relationship between various toxicological endpoints in Caenorhabditis elegans exposed to organophosphorus insecticides. J Toxicol Environ Health A. 2008;71(15):1043-50.

The toxicity of 10 organophophorus (OP) insecticides-acephate, dimethoate, dichlorvos, dicrotophos, monocrotophos, methamidophos, phosphamidon, omethoate, phosdrin, and trichlorfon-was evaluated in Caenorhabditis elegans using lethality, movement, and acetylcholinesterase (AChE) activity as the endpoints after a 4-hr- exposure period.
9(0,0,1,4) Details
18070496 Wan WG, Zheng SC, Zou HJ, Ma SD, Tao GZ, Xu ZF, Zhang B, Chen JJ, Fang LY, Zhu ZJ: [Different therapeutic efficacy of parlidoxime chloride PAM-Cl on AChE against acute toxicity of methamidophos, dichlorovs and omethoate]. Zhonghua Lao Dong Wei Sheng Zhi Ye Bing Za Zhi. 2007 Oct;25(10):586-9.
8(0,0,1,3) Details
2241237 Maroni M, Catenacci G, Galli D, Cavallo D, Ravazzani G: Biological monitoring of human exposure to acephate. Arch Environ Contam Toxicol. 1990 Sep-Oct;19(5):782-8.

Before, during, and after exposure, the workers were monitored for the urine content of acephate and methamidophos, and for erythrocyte (AChE) and plasma (PChE) cholinesterase levels.
7(0,0,1,2) Details
9192209 Guven M, Unluhizarci K, Goktas Z, Kurtoglu S: Intravenous organophosphate injection: an unusual way of intoxication. Hum Exp Toxicol. 1997 May;16(5):279-80.

Organophosphate insecticides strongly inhibit both true cholinesterase and pseudocholinesterase activities.
In this report, we have reported a patient who injected himself a strong organophosphate compound, methamidophos, and showed the typical clinical picture of organophosphate intoxication.
1(0,0,0,1) Details
3672530 Pauluhn J, Machemer L, Kimmerle G: Effects of inhaled cholinesterase inhibitors on bronchial tonus and on plasma and erythrocyte acetylcholine esterase activity in rats. Toxicology. 1987 Oct 30;46(2):177-90.

The compounds tested were dichlorvos, fenamiphos, methamidophos, parathion, a pyrimidine thiophosphate and the carbamate propoxur.
1(0,0,0,1) Details
18804659 Pohanka M, Jun D, Kuca K: Improvement of acetylcholinesterase-based assay for organophosphates in way of identification by reactivators. Talanta. 2008 Oct 19;77(1):451-4. Epub 2008 Jun 17.

The most significant identification was based on methamidophos inhibited AChE reactivation by HI-6 or pralidoxime and paraoxon-ethyl inhibited AChE by obidoxime; moreover, identification of trichlorfon and paraoxon-methyl was possible, too.
85(1,1,1,5) Details
12748382 Genzen JR, McGehee DS: Short- and long-term enhancement of excitatory transmission in the spinal cord dorsal horn by nicotinic acetylcholine receptors. Proc Natl Acad Sci U S A. 2003 May 27;100(11):6807-12. Epub 2003 May 14.

Inhibition of acetylcholinesterase with methamidophos also enhanced transmission, demonstrating a similar effect of endogenous acetylcholine. nAChR activation also enhanced transmission by dorsal root entry zone stimulation, suggesting that alpha7 nAChRs on the central terminals of DRG afferents mediate this effect.
81(1,1,1,1) Details
8492300 Jokanovic M, Johnson MK: Interactions in vitro of some organophosphoramidates with neuropathy target esterase and acetylcholinesterase of hen brain. J Biochem Toxicol. 1993 Mar;8(1):19-31.

However, it has been shown recently that certain N-unsubstituted organophosphoro-monoamidates (analogues of methamidophos) cause delayed neuropathy even though the inhibited NTE appeared not to have aged (Johnson et al. (1991).
6(0,0,0,6) Details
15041023 Li F, Han Z: Mutations in acetylcholinesterase associated with insecticide resistance in the cotton aphid, Aphis gossypii Glover. Insect Biochem Mol Biol. 2004 Apr;34(4):397-405.

6(0,0,0,6) Details
6710513 Glickman AH, Wing KD, Casida JE: Profenofos insecticide bioactivation in relation to antidote action and the stereospecificity of acetylcholinesterase inhibition, reactivation, and aging. Toxicol Appl Pharmacol. 1984 Mar 30;73(1):16-22.

Brain AChE from chicks poisoned with profenofos was not reactivated by pralidoxime methanesulfonate, although it was from chicks poisoned with the phosphoramidothiolate, methamidophos.
4(0,0,0,4) Details
9568380 Singh AK, White T, Spassova D, Jiang Y: Physicochemical, molecular-orbital and electronic properties of acephate and methamidophos. Comp Biochem Physiol C Pharmacol Toxicol Endocrinol. 1998 Jan;119(1):107-17.

Me is a potent inhibitor, while Ac is a poor inhibitor of mammalian AChE (mAChE).
3(0,0,0,3) Details
16042503 Lotti M, Moretto A: Organophosphate-induced delayed polyneuropathy. . Toxicol Rev. 2005;24(1):37-49.

The ratio of inhibitory powers for acetylcholinesterase and NTE represents the crucial guideline for the aetiological attribution of OP-induced peripheral neuropathy.
In this article, we mainly discuss OP pesticide poisoning, particularly when caused by chlorpyrifos, dichlorvos, isofenphos, methamidophos, mipafox, trichlorfon, trichlornat, phosphamidon/mevinphos and by certain carbamates.
1(0,0,0,1) Details
19680979 Jensen BH, Petersen A, Christensen T: Probabilistic assessment of the cumulative dietary acute exposure of the population of Denmark to organophosphorus and carbamate pesticides. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2009 Jul;26(7):1038-48.

Organophosphorus and carbamate pesticides are acetylcholinesterase-inhibiting pesticides and as such have a common mode of action.
We used the relative potency factor (RPF) approach to normalize the toxicity of the various organophosphorus and carbamate pesticides to the two index compounds chlorpyriphos and methamidophos.
1(0,0,0,1) Details
19371630 Bosgra S, van Eijkeren JC, van der Schans MJ, Langenberg JP, Slob W: Toxicodynamic analysis of the combined cholinesterase inhibition by paraoxon and methamidophos in human whole blood. Toxicol Appl Pharmacol. 2009 Apr 1;236(1):9-15. Epub 2009 Jan 20.

A toxicodynamic model describing the processes related to both OPs in inhibiting AChE activity was developed, and fit to the observed activities.
1(0,0,0,1) Details
2284053 Wilson BW, Henderson JD, Kellner TP, McEuen SF, Griffis LC, Lai JC: Acetylcholinesterase and neuropathy target esterase in chickens treated with acephate. Neurotoxicology. 1990 Fall;11(3):483-91.

Reports that near-lethal doses of the pesticide methamidophos (O,S-dimethyl phosphoramidothioate) caused a delayed neurotoxicity (OPIDN) in humans and that another phosphoramidate, isofenphos, caused OPIDN in the hen at high doses, prompted a study of the abilities of acephate (O,S-dimethyl acetylphosphoramidothioate) to inhibit brain acetylcholinesterase (AChE) and neuropathy target esterase (NTE) in vivo.
66(0,2,2,6) Details
19680907 Chen C, Li Y, Chen M, Chen Z, Qian Y: Organophosphorus pesticide residues in milled rice (Oryza sativa) on the Chinese market and dietary risk assessment. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2009 Mar;26(3):340-7.

Relative potency factors (RPFs) for each pesticide were calculated with methamidophos as the index compound (IC), using 1- or 2-year chronic non-observed adverse effect levels (NOAEL) for AChE inhibition, mostly in rat brain, obtained from international evaluations of pesticides.
63(0,2,2,3) Details
17421051 Wu G, Miyata T, Kang CY, Xie LH: Insecticide toxicity and synergism by enzyme inhibitors in 18 species of pest insect and natural enemies in crucifer vegetable crops. Pest Manag Sci. 2007 May;63(5):500-10.

Meanwhile, the inhibitory effects of these enzyme inhibitors on the activities of acetylcholinesterases (AChE), carboxyesterases (CarE) and glutathione-S-transferases (GST), in vivo, were also studied.
PB showed the highest synergism on methamidophos, fenvalerate, fipronil and avermectin in nine species of pest insects and natural enemies.
3(0,0,0,3) Details
12191869 He F, Chen S, Tang X, Gan W, Tao B, Wen B: Biological monitoring of combined exposure to organophosphates and pyrethroids. Toxicol Lett. 2002 Aug 5;134(1-3):119-24.

In area J, the subgroups Ja (40 subjects) and Jb (36 subjects) sprayed on rice crops either the organophosphate (OP) insecticide methamidophos or the mixture methamidophos-deltamethrin (a pyrethroid, Pyr).
Erythrocyte acetylcholinesterase (AChE) was measured by the Ellman's method before spraying, after 2-h exposure and 1 h later.
3(0,0,0,3) Details
15081274 Vidair CA: Age dependence of organophosphate and carbamate neurotoxicity in the postnatal rat: extrapolation to the human. Toxicol Appl Pharmacol. 2004 Apr 15;196(2):287-302.

Because these compounds probably exert their neurotoxic effects through the inhibition of acetylcholinesterase (AChE), the above question can be narrowed to whether the cholinesterase inhibition and neurotoxicity they produce is age-dependent, both in terms of the effects produced and potency.
Four pesticides were tested in rat pups in their third postnatal week: aldicarb, chlorpyrifos, malathion, and methamidophos.
1(0,0,0,1) Details
17032020 Lin K, Zhou S, Xu C, Liu W: Enantiomeric resolution and biotoxicity of methamidophos. . J Agric Food Chem. 2006 Oct 18;54(21):8134-8.

The t test at the 95% level of confidence indicated significant differences between the enantiomers in their in vitro inhibition toward acetylcholinesterases of bovine erythrocytes and Electrophorus electricus and in vivo acute aquatic toxicity to Daphnia magna.
1(0,0,0,1) Details
9074804 Mahajna M, Quistad GB, Casida JE: Acephate insecticide toxicity: safety conferred by inhibition of the bioactivating carboxyamidase by the metabolite methamidophos. Chem Res Toxicol. 1997 Jan;10(1):64-9.

Acephate is an important systemic organophosphorus insecticide with toxicity attributed to bioactivation on metabolic conversion to methamidophos (or an oxidized metabolite thereof) which acts as an acetylcholinesterase (AChE) inhibitor.
62(0,2,2,2) Details
15568361 Wu G, Jiang S, Miyata T: Seasonal changes of methamidophos susceptibility and biochemical properties in Plutella xylostella (Lepidoptera: Yponomeutidae) and its parasitoid Cotesia plutellae (Hymenoptera: Braconidae). J Econ Entomol. 2004 Oct;97(5):1689-98.

Methamidophos resistance and acetylcholinesterase (AChE) insensitivity to methamidophos, dichlorvos, and carbofuran were determined in the field populations of Plutella xylostella (L.) (Lepidoptera: Yponomeutidae) and its parasitoid Cotesia plutellae Kurdjumov (Hymenoptera: Braconidae) collected from the corresponding hosts between October 1998 and December 2003 in Fuzhou and Minhou, Fijian, China.
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15508279 Timur S, Telefoncu A: Acetylcholinesterase (AChE) electrodes based on gelatin and chitosan matrices for the pesticide detection. Artif Cells Blood Substit Immobil Biotechnol. 2004;32(3):427-42.

Linear ranges for different organophosphates such as malathion, parathion-methyl, and methamidophos were detected by using both types of biosensor system.
3(0,0,0,3) Details
11696925 Singh AK: QSAR for the organophosphate-induced inhibition and 'aging' of the enzyme neuropathy target esterase (NTE). SAR QSAR Environ Res. 2001;12(3):275-95.

The neuropathy-target-esterase (NTE) inhibition data were either obtained from the literature for a number of OP compounds or were determined experimentally for methamidophos, acephate, coumaphos and EPN.
Log10I50 for AChE that determined the OP concentration causing 50% inhibition in AChE activity, correlated with EBOND and Charge-1 (Eq. (3)).
1(0,0,0,1) Details
11350214 Quistad GB, Sparks SE, Casida JE: Fatty acid amide hydrolase inhibition by neurotoxic organophosphorus pesticides. Toxicol Appl Pharmacol. 2001 May 15;173(1):48-55.

These BDPOs and EOPF inhibit mouse brain FAAH in vitro with > or =200-fold higher potency than for AChE.
Five OP pesticides inhibit 50% of the brain FAAH activity (ED50) at <30 mg/kg 4 h after ip administration to mice; while inhibition by chlorpyrifos, diazinon, and methamidophos occurs near acutely toxic levels, profenofos and tribufos are effective at asymptomatic doses.
1(0,0,0,1) Details
6662290 Eigenberg DA, Pazdernik TL, Doull J: Hemoperfusion and pharmacokinetic studies with methamidophos in the rat. Fundam Appl Toxicol. 1983 Nov-Dec;3(6):496-501.

0(0,0,0,0) Details
17402711 Hornberg A, Tunemalm AK, Ekstrom F: Crystal structures of acetylcholinesterase in complex with organophosphorus compounds suggest that the acyl pocket modulates the aging reaction by precluding the formation of the trigonal bipyramidal transition state. Biochemistry. 2007 Apr 24;46(16):4815-25. Epub 2007 Apr 3.

In this study, we present crystal structures of the non-aged and aged complexes between Mus musculus AChE (mAChE) and the nerve agents sarin, VX, and diisopropyl fluorophosphate (DFP) and the OP-based insecticides methamidophos (MeP) and fenamiphos (FeP).
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10530896 Singh AK: Quantitative structure-activity relationships for phosphoramidothioate toxicity in housefly. Comp Biochem Physiol C Pharmacol Toxicol Endocrinol. 1999 Jul;123(3):241-55.

The 3D structure of a potent phosphoramidothioate such as methamidophos was such that its P-O (-) group interacted with the enzyme's 'oxy-anion hole', NH2+ group formed an H-bond with the enzyme's H-bonding site, and leaving group (-S) oriented toward the AChE 'gorge' opening.
35(0,1,1,5) Details
8783813 Worek F, Kirchner T, Backer M, Szinicz L: Reactivation by various oximes of human erythrocyte acetylcholinesterase inhibited by different organophosphorus compounds. Arch Toxicol. 1996;70(8):497-503.

For this purpose human erythrocyte AChE (EC 3.1.1.7) was inhibited (30 min) by chlorfenvinphos, dichlorvos, dicrotophos, heptenophos, mevinphos, monocrotophos, paraoxon, phosphamidon, trichlorfon, malaoxon, omethoate, oxydemeton-methyl or methamidophos by 85-98% of control.
34(0,1,1,4) Details
11962304 Yao H, Jiang C, Ye G, Cheng J: [Insecticide resistance of different populations of white-backed planthopper, Sogatella furcifera (Horvath) (Homoptera:Delphacidae)]. Ying Yong Sheng Tai Xue Bao. 2002 Jan;13(1):101-5.

The specific activities of some resistance-associated enzymes, i.e. esterase, carboxylesterase, glutathione S-transferase and acetylcholinesterase from these populations were also measured.
The resistant levels to malathion, methamidophos, isoprocarb and buprofezin were markedly higher in Yunnan and Hainan populations than in other populations, but considerably more heterogeneity in response to insecticides was found in Zhejiang and Guangxi populations.
1(0,0,0,1) Details
19674799 Tryfonos M, Papaefthimiou C, Antonopoulou E, Theophilidis G: Comparing the inhibitory effects of five protoxicant organophosphates (azinphos-methyl, parathion-methyl, chlorpyriphos-methyl, methamidophos and diazinon) on the spontaneously beating auricle of Sparus aurata: an in vitro study. Aquat Toxicol. 2009 Sep 14;94(3):211-8. Epub 2009 Jul 16.

Organophosphates (OPs) can provoke toxicity by inhibiting acetylcholinesterase (AChE) in non-target organisms, like fish.
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19442833 Lima CS, Ribeiro-Carvalho A, Filgueiras CC, Manhaes AC, Meyer A, Abreu-Villaca Y: Exposure to methamidophos at adulthood elicits depressive-like behavior in mice. Neurotoxicology. 2009 May;30(3):471-8. Epub 2009 Feb 7.

During exposure, acetylcholinesterase activity was inhibited in the HiD (43%) and LoD (15%) groups.
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