ArticleToxicology and applied pharmacology2009
Mass spectrometry identifies multiple organophosphorylated sites on tubulin.
Article in Toxicology and applied pharmacology, 2009. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 22 papers.
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Who cites it
22 citing papers in PubMed, 46 citations in OpenAlex.
- Current review on inducible nitric oxide synthase and Src tyrosine kinase inhibitors as disease-modifiers in preclinical models of epilepsy.Histology and histopathology · 2026Review
- Effects of the nerve agent VX on hiPSC-derived motor neurons.Archives of toxicology · 2024Article
- Article
- Ensemble machine learning to evaluate the in vivo acute oral toxicity and in vitro human acetylcholinesterase inhibitory activity of organophosphates.Archives of toxicology · 2021Article
- Positron emission tomography studies of organophosphate chemical threats and oxime countermeasures.Neurobiology of disease · 2020Review
- The inhibition, reactivation and mechanism of VX-, sarin-, fluoro-VX and fluoro-sarin surrogates following their interaction with HuAChE and HuBuChE.Chemico-biological interactions · 2018Article
- Covalent binding of the organophosphate insecticide profenofos to tyrosine on α- and β-tubulin proteins.Chemosphere · 2018Article
- Blood-Brain Barrier Cellular Responses Toward Organophosphates: Natural Compensatory Processes and Exogenous Interventions to Rescue Barrier Properties.Frontiers in cellular neuroscience · 2018Article
- Monoclonal Antibody That Recognizes Diethoxyphosphotyrosine-Modified Proteins and Peptides Independent of Surrounding Amino Acids.Chemical research in toxicology · 2017Article
- Developmental neurotoxicity of the organophosphorus insecticide chlorpyrifos: from clinical findings to preclinical models and potential mechanisms.Journal of neurochemistry · 2017Review
- Pharmacologically increasing microtubule acetylation corrects stress-exacerbated effects of organophosphates on neurons.Traffic (Copenhagen, Denmark) · 2017Article
- Resolving pathways of interaction of mipafox and a sarin analog with human acetylcholinesterase by kinetics, mass spectrometry and molecular modeling approaches.Archives of toxicology · 2016Article
- Preparation and characterization of diethoxy- and monoethoxy phosphylated ('aged') serine haptens and use in the production of monoclonal antibodies.Chemico-biological interactions · 2014Article
- PON1 status does not influence cholinesterase activity in Egyptian agricultural workers exposed to chlorpyrifos.Toxicology and applied pharmacology · 2012Article
- Cresyl saligenin phosphate, an organophosphorus toxicant, makes covalent adducts with histidine, lysine, and tyrosine residues of human serum albumin.Chemical research in toxicology · 2012Article
- Functional consequences of repeated organophosphate exposure: potential non-cholinergic mechanisms.Pharmacology & therapeutics · 2012Review
- Review of tyrosine and lysine as new motifs for organophosphate binding to proteins that have no active site serine.Chemico-biological interactions · 2010Review
- Mass spectral characterization of organophosphate-labeled, tyrosine-containing peptides: characteristic mass fragments and a new binding motif for organophosphates.Journal of chromatography. B, Analytical technologies in the biomedical and life sciences · 2010Article
- Mice treated with chlorpyrifos or chlorpyrifos oxon have organophosphorylated tubulin in the brain and disrupted microtubule structures, suggesting a role for tubulin in neurotoxicity associated with exposure to organophosphorus agents.Toxicological sciences : an official journal of the Society of Toxicology · 2010Article
- Mass spectral characterization of organophosphate-labeled lysine in peptides.Analytical biochemistry · 2009Article
Corrections and comments
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Authors and funding
7 authors at 3 institutions in 1 country.
Funding
Abstract
Acute toxicity of organophosphorus poisons (OP) is explained by inhibition of acetylcholinesterase in nerve synapses. Low-dose effects are hypothesized to result from modification of other proteins, whose identity is not yet established. The goal of the present work was to obtain information that would make it possible to identify tubulin as a target of OP exposure. Tubulin was selected for study because live mice injected with a nontoxic dose of a biotinylated organophosphorus agent appeared to have OP-labeled tubulin in brain as determined by binding to avidin beads and mass spectrometry. The experiments with live mice were not conclusive because binding to avidin beads could be nonspecific. To be convincing, it is necessary to find and characterize the OP-labeled tubulin peptide. The search for OP-labeled tubulin peptides was begun by identifying residues capable of making a covalent bond with OP. Pure bovine tubulin (0.012 mM) was treated with 0.01-0.5 mM chlorpyrifos oxon for 24 h at 37 degrees C in pH 8.3 buffer. The identity of labeled amino acids and percent labeling was determined by mass spectrometry. Chlorpyrifos oxon bound covalently to tyrosines 83, 103, 108, 161, 224, 262, 272, 357, and 399 in bovine alpha tubulin, and to tyrosines 50, 51, 59, 106, 159, 281, 310, and 340 in bovine beta tubulin. The most reactive were tyrosine 83 in alpha and tyrosine 281 in beta tubulin. In the presence of 1 mM GTP, percent labeling increased 2-fold. Based on the crystal structure of the tubulin heterodimer (PDB 1jff) tyrosines 83 and 281 are well exposed to solvent. In conclusion seventeen tyrosines in tubulin have the potential to covalently bind chlorpyrifos oxon. These results will be useful when searching for OP-labeled tubulin in live animals.
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Registered trials
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