Effects of pesticide chemicals on the activity of metabolic enzymes: focus on thiocarbamates

Bibliography

• Mulkey ME. MEMORANDUM. Thiocarbamates: a determination of the existence of a common mechanism of toxicity and a screening level cumulative food risk assessment. 2001. Available from: http://epa.gov/pesticides/cumulative/thiocarb.pdf
   Google Scholar
• Axelstad M, Boberg J, Nellemann C, et al. Exposure to the widely used fungicide mancozeb causes thyroid hormone disruption in rat dams but no behavioral effects in the offspring. Toxicol Sci 2011;120(2):439-46
   PubMed Web of Science ®Google Scholar
• Oskarsson A, Lind B. Increased lead levels in brain after long-term treatment with lead and dithiocarbamate or thiuram derivatives in rats. Acta Pharmacol Toxicol (Copenh) 1985;56(4):309-15
   PubMedGoogle Scholar
• Frank N, Christmann A, Frei E. Comparative studies on the pharmacokinetics of hydrophilic prolinedithiocarbamate, sarcosinedithiocarbamate and the less hydrophilic diethyldithiocarbamate. Toxicology 1995;95(1-3):113-22
   PubMed Web of Science ®Google Scholar
• Guven K, Deveci E, Akba O, et al. The accumulation and histological effects of organometallic fungicides Propineb and Maneb in the kidneys of fetus and female rats during pregnancy. Toxicol Lett 1998;99(2):91-8
   PubMed Web of Science ®Google Scholar
• Narayan CR, Rasaputra KS, Liyanage R, et al. Dithiocarbamate toxicity - an appraisal. In: Stoytcheva M, editor. Pesticides in the modern world - effects of pesticides exposure. InTech; Rijeka, Croatia; 2011. 978-953-307-454-2
   Google Scholar
• Sunderman FW. Chelation therapy in nickel poisoning. Ann Clin Lab Sci 1981;11(1):1-8
   PubMed Web of Science ®Google Scholar
• Kitson TM. The disulfiram – ethanol reaction: a review. J Stud Alcohol 1977;38(1):96-113
   PubMed Web of Science ®Google Scholar
• Lipsky JJ, Shen ML, Naylor S. In vivo inhibition of aldehyde dehydrogenase by disulfiram. Chem Biol Interact 2001;130-132(1-3):93-102
   PubMed Web of Science ®Google Scholar
• Viquez OM, Caito SW, McDonald WH, et al. Electrophilic adduction of ubiquitin activating enzyme E1 by N,N-diethyldithiocarbamate inhibits ubiquitin activation and is accompanied by striatal injury in the rat. Chem Res Toxicol 2012;25(11):2310-21
   PubMed Web of Science ®Google Scholar
• Jin L, Davis MR, Hu P, et al. Identification of novel glutathione conjugates of disulfiram and diethyldithiocarbamate in rat bile by liquid chromatography-tandem mass spectrometry. Evidence for metabolic activation of disulfiram in vivo. Chem Res Toxicol 1994;7(4):526-33
   PubMed Web of Science ®Google Scholar
• Staub RE, Quistad GB, Casida JE. Mechanism for benomyl action as a mitochondrial aldehyde dehydrogenase inhibitor in mice. Chem Res Toxicol 1998;11(5):535-43
   PubMed Web of Science ®Google Scholar
• Stromme JH. Effects of diethyldithiocarbamate and disulfiram on glucose metabolism and glutathione content of human erythrocytes. Biochem Pharmacol 1963;12:705-15
   PubMed Web of Science ®Google Scholar
• Madan A, Parkinson A, Faiman MD. Identification of the human P-450 enzymes responsible for the sulfoxidation and thiono-oxidation of diethyldithiocarbamate methyl ester: role of P-450 enzymes in disulfiram bioactivation. Alcohol Clin Exp Res 1998;22(6):1212-19
   PubMed Web of Science ®Google Scholar
• Pace NJ, Weerapana E. Diverse functional roles of reactive cysteines. ACS Chem Biol 2013;8(2):283-96
   PubMed Web of Science ®Google Scholar
• Zimmerman LJ, Valentine HL, Valentine WM. Characterization of S-(N,N-dialkylaminocarbonyl)cysteine adducts and enzyme inhibition produced by thiocarbamate herbicides in the rat. Chem Res Toxicol 2004;17(2):258-67
   PubMed Web of Science ®Google Scholar
• Tsang MM, Trombetta LD. The protective role of chelators and antioxidants on mancozeb-induced toxicity in rat hippocampal astrocytes. Toxicol Ind Health 2007;23(8):459-70
   PubMed Web of Science ®Google Scholar
• Törrönen R, Marselos M. Changes in the hepatic copper conent after treatment with foreign compounds. Arch Toxicol Suppl 1978(1):247-9
   PubMedGoogle Scholar
• Lippmann W, Lloyd K. Dopamine-hydroxylase inhibition by dimethyldithiocarbamate and related compounds. Biochem Pharmacol 1969;18(10):2507-16
   PubMed Web of Science ®Google Scholar
• Lushchak V, Semchyshyn H, Lushchak O, et al. Diethyldithiocarbamate inhibits in vivo Cu,Zn-superoxide dismutase and perturbs free radical processes in the yeast Saccharomyces cerevisiae cells. Biochem Biophys Res Commun 2005;338(4):1739-44
   PubMed Web of Science ®Google Scholar
• Chen D, Cui QC, Yang H, et al. Disulfiram, a clinically used anti-alcoholism drug and copper-binding agent, induces apoptotic cell death in breast cancer cultures and xenografts via inhibition of the proteasome activity. Cancer Res 2006;66(21):10425-33
   PubMed Web of Science ®Google Scholar
• Piątkiewicz P, Czech A. Glucose metabolism disorders and the risk of cancer. Arch Immunol Ther Exp (Warsz) 2011;59(3):215-30
   PubMed Web of Science ®Google Scholar
• Beltrán FA, Acuna AI, Paz Miró M, Castro MA. Brain energy metabolism in health and disease. In: Contreras CM, editor. Neuroscience - dealing with frontiers. InTech; 2012. Available from: http://www.intechopen.com/books/neuroscience-dealing-with-frontiers/brainenergy-metabolism-in-health-and-disease
   Google Scholar
• Jay D. Inhibition of membrane-bound succinate dehydrogenase by disulfiram. J Bioenerg Biomembr 1991;23(2):335-43
   PubMed Web of Science ®Google Scholar
• Stromme JH. Inhibition of hexokinase by disulfiram and diethyldithiocarbamate. Biochem Pharmacol 1963;12:157-66
   PubMed Web of Science ®Google Scholar
• Pettersson H, Tottmar O. Inhibition of aldehyde dehydrogenases in rat brain and liver by disulfiram and coprine. J Neurochem 1982;39(3):628-34
   PubMed Web of Science ®Google Scholar
• Veverka KA, Johnson KL, Mays DC, et al. Inhibition of aldehyde dehydrogenase by disulfiram and its metabolite methyl diethylthiocarbamoyl-sulfoxide. Biochem Pharmacol 1997;53(4):511-18
   PubMed Web of Science ®Google Scholar
• Ferraz HB, Bertolucci PH, Pereira JS, et al. Chronic exposure to the fungicide maneb may produce symptoms and signs of CNS manganese intoxication. Neurology 1988;38(4):550-3
   PubMed Web of Science ®Google Scholar
• Meco G, Bonifati V, Vanacore N, et al. Parkinsonism after chronic exposure to the fungicide maneb (manganese ethylene-bis-dithiocarbamate). Scand J Work Environ Health 1994;20(4):301-5
   PubMed Web of Science ®Google Scholar
• Montine TJ, Underhill TM, Valentine WM, et al. Dialkyldithiocarbamates inhibit tyrosine hydroxylase activity in PC12 cells and in fibroblasts that express tyrosine hydroxylase. Neurodegeneration 1995;4(3):283-90
   PubMedGoogle Scholar
• Moretto A, Colosio C. Biochemical and toxicological evidence of neurological effects of pesticides: the example of Parkinson’s disease. Neurotoxicology 2011;32(4):383-91
   PubMed Web of Science ®Google Scholar
• Wang A, Costello S, Cockburn M, et al. Parkinson’s disease risk from ambient exposure to pesticides. Eur J Epidemiol 2011;26(7):547-55
   PubMed Web of Science ®Google Scholar
• Brown TP, Rumsby PC, Capleton AC, et al. Pesticides and Parkinson’s disease--is there a link? Environ Health Perspect 2006;114(2):156-64
   PubMed Web of Science ®Google Scholar
• Tolleson C, Claassen D. The function of tyrosine hydroxylase in the normal and Parkinsonian brain. CNS Neurol Disord Drug Targets 2012;11(4):381-6
   PubMed Web of Science ®Google Scholar
• Szmigielski A. Effect of disulfiram and sodium diethyldithiocarbamate on tyrosine and dopamine-beta-hydroxylases activities in rat brain and heart. Pol J Pharmacol Pharm 1975;27(2):153-9
   PubMedGoogle Scholar
• Levin EY, Levenberg B, Kaufman S. The enzymatic conversion of 3,4-dihydroxyphenylethylamine to norepinephrine. J Biol Chem 1960;235:2080-6
   PubMed Web of Science ®Google Scholar
• Goldstein M, Lauber E, Mckereghan MR. Studies on the purification and characterization of 3,4-dihydroxyphenylethylamine beta-hydroxylase. J Biol Chem 1965;240:2066-72
   PubMed Web of Science ®Google Scholar
• Goldstein M, Anagnoste B, Lauber E, et al. Inhibition of dopamine-beta-hydroxylase by disulfiram. Life Sci 1964;3:763-7
   PubMed Web of Science ®Google Scholar
• Caroldi S, De Paris P. Comparative effects of two dithiocarbamates disulfiram and thiram, on adrenal catecholamine content and on plasma dopamine-beta-hydroxylase activity. Arch Toxicol 1995;69(10):690-3
   PubMed Web of Science ®Google Scholar
• Musacchio JM, Goldstein M, Anagnoste B, et al. Inhibition of dopamine-beta-hydroxylase by disulfiram in vivo. J Pharmacol Exp Ther 1966;152(1):56-61
   PubMed Web of Science ®Google Scholar
• Carroll KM, Fenton LR, Ball SA, et al. Efficacy of disulfiram and cognitive behavior therapy in cocaine-dependent outpatients: a randomized placebo-controlled trial. Arch Gen Psychiatry 2004;61(3):264-72
   PubMed Web of Science ®Google Scholar
• Di Marzo V, Fontana A, Cadas H, et al. Formation and inactivation of endogenous cannabinoid anandamide in central neurons. Nature 1994;372(6507):686-91
   PubMed Web of Science ®Google Scholar
• Köfalvi A, Rodrigues RJ, Ledent C, et al. Involvement of cannabinoid receptors in the regulation of neurotransmitter release in the rodent striatum: a combined immunochemical and pharmacological analysis. J Neurosci 2005;25(11):2874-84
   PubMed Web of Science ®Google Scholar
• Fernández-Ruiz J. The endocannabinoid system as a target for the treatment of motor dysfunction. Br J Pharmacol 2009;156(7):1029-40
   PubMed Web of Science ®Google Scholar
• Ahn K, McKinney MK, Cravatt BF. Enzymatic pathways that regulate endocannabinoid signaling in the nervous system. Chem Rev 2008;108(5):1687-707
   PubMed Web of Science ®Google Scholar
• Labar G, Bauvois C, Muccioli GG, et al. Disulfiram is an inhibitor of human purified monoacylglycerol lipase, the enzyme regulating 2-arachidonoylglycerol signaling. ChemBioChem 2007;8(11):1293-7
   PubMed Web of Science ®Google Scholar
• Kapanda CN, Muccioli GG, Labar G, et al. Bis(dialkylaminethiocarbonyl)disulfides as potent and selective monoglyceride lipase inhibitors. J Med Chem 2009;52(22):7310-14
   PubMed Web of Science ®Google Scholar
• Nomura DK, Casida JE. Activity-based protein profiling of organophosphorus and thiocarbamate pesticides reveals multiple serine hydrolase targets in mouse brain. J Agric Food Chem 2011;59(7):2808-15
   PubMed Web of Science ®Google Scholar
• Giuffrida A, McMahon LR. In vivo pharmacology of endocannabinoids and their metabolic inhibitors: therapeutic implications in Parkinson’s disease and abuse liability. Prostaglandins Other Lipid Mediat 2010;91(3-4):90-103
   PubMed Web of Science ®Google Scholar
• Amm I, Sommer T, Wolf DH. Protein quality control and elimination of protein waste: the role of the ubiquitin-proteasome system. Biochim Biophys Acta 2014;1843(1):182-96
   PubMed Web of Science ®Google Scholar
• Chou AP, Maidment N, Klintenberg R, et al. Ziram causes dopaminergic cell damage by inhibiting E1 ligase of the proteasome. J Biol Chem 2008;283(50):34696-703
   PubMed Web of Science ®Google Scholar
• Hershko A, Ciechanover A. The ubiquitin system. Annu Rev Biochem 1998;67:425-79
   PubMed Web of Science ®Google Scholar
• Joazeiro CA, Weissman AM. RING finger proteins: mediators of ubiquitin ligase activity. Cell 2000;102(5):549-52
   PubMed Web of Science ®Google Scholar
• Hayakawa M, Miyashita H, Sakamoto I, et al. Evidence that reactive oxygen species do not mediate NF-kappaB activation. EMBO J 2003;22(13):3356-66
   PubMed Web of Science ®Google Scholar
• Brahemi G, Kona FR, Fiasella A, et al. Exploring the structural requirements for inhibition of the ubiquitin E3 ligase breast cancer associated protein 2 (BCA2) as a treatment for breast cancer. J Med Chem 2010;53(7):2757-65
   PubMed Web of Science ®Google Scholar
• Buac D, Schmitt S, Ventro G, et al. Dithiocarbamate-based coordination compounds as potent proteasome inhibitors in human cancer cells. Mini Rev Med Chem 2012;12(12):1193-201
   PubMed Web of Science ®Google Scholar
• Nalepa G, Rolfe M, Harper JW. Drug discovery in the ubiquitin-proteasome system. Nat Rev Drug Discov 2006;5(7):596-613
   PubMed Web of Science ®Google Scholar
• Zhou Y, Shie FS, Piccardo P, et al. Proteasomal inhibition induced by manganese ethylene-bis-dithiocarbamate: relevance to Parkinson’s disease. Neuroscience 2004;128(2):281-91
   PubMed Web of Science ®Google Scholar
• Yerlikaya A, Yöntem M. The significance of ubiquitin proteasome pathway in cancer development. Recent Pat Anticancer Drug Discov 2013;8(3):298-309
   PubMed Web of Science ®Google Scholar
• Rae C, Tesson M, Babich JW, et al. The role of copper in disulfiram-induced toxicity and radiosensitization of cancer cells. J Nucl Med 2013;54(6):953-60
   PubMed Web of Science ®Google Scholar
• Cvek B, Dvorak Z. Targeting of nuclear factor-kappaB and proteasome by dithiocarbamate complexes with metals. Curr Pharm Des 2007;13(30):3155-67
   PubMed Web of Science ®Google Scholar
• Amici M, Forti K, Nobili C, et al. Effect of neurotoxic metal ions on the proteolytic activities of the 20S proteasome from bovine brain. J Biol Inorg Chem 2002;7(7-8):750-6
   PubMed Web of Science ®Google Scholar
• Kona FR, Buac D, M Burger A. Disulfiram, and disulfiram derivatives as novel potential anticancer drugs targeting the ubiquitin-proteasome system in both preclinical and clinical studies. Curr Cancer Drug Targets 2011;11(3):338-46
   PubMed Web of Science ®Google Scholar
• Ellis MK, Richardson AG, Foster JR, et al. The reproductive toxicity of molinate and metabolites to the male rat: effects on testosterone and sperm morphology. Toxicol Appl Pharmacol 1998;151(1):22-32
   PubMed Web of Science ®Google Scholar
• Franco M, Chávez E, Pérez-Méndez O. Pleiotropic effects of thyroid hormones: learning from hypothyroidism. J Thyroid Res 2011;2011:321030
   PubMedGoogle Scholar
• Kackar R, Srivastava MK, Raizada RB. Studies on rat thyroid after oral administration of mancozeb: morphological and biochemical evaluations. J Appl Toxicol 1997;17(6):369-75
   PubMed Web of Science ®Google Scholar
• Marinovich M, Guizzetti M, Ghilardi F, et al. Thyroid peroxidase as toxicity target for dithiocarbamates. Arch Toxicol 1997;71(8):508-12
   PubMed Web of Science ®Google Scholar
• Doerge DR, Takazawa RS. Mechanism of thyroid peroxidase inhibition by ethylenethiourea. Chem Res Toxicol 3(2):98-101
   PubMed Web of Science ®Google Scholar
• Stewart PM, Krozowski ZS. 11 beta-Hydroxysteroid dehydrogenase. Vitam Horm 1999;57:249-324
   PubMed Web of Science ®Google Scholar
• Atanasov AG, Tam S, Röcken JM, et al. Inhibition of 11 beta-hydroxysteroid dehydrogenase type 2 by dithiocarbamates. Biochem Biophys Res Commun 2003;308(2):257-62
   PubMed Web of Science ®Google Scholar
• Garbrecht MR, Krozowski ZS, Snyder JM, et al. Reduction of glucocorticoid receptor ligand binding by the 11-beta hydroxysteroid dehydrogenase type 2 inhibitor, Thiram. Steroids 2006;71(10):895-901
   PubMed Web of Science ®Google Scholar
• Brady JF, Xiao F, Wang MH, et al. Effects of disulfiram on hepatic P450IIE1, other microsomal enzymes, and hepatotoxicity in rats. Toxicol Appl Pharmacol 1991;108(2):366-73
   PubMed Web of Science ®Google Scholar
• Pratt-Hyatt M, Lin HL, Hollenberg PF. Mechanism-based inactivation of human CYP2E1 by diethyldithocarbamate. Drug Metab Dispos 2010;38(12):2286-92
   PubMed Web of Science ®Google Scholar
• Martini R, Ingelman-Sundberg M, Murray M. Pretranslational and posttranslational regulation of rat hepatic CYPs 3A2 and 2E1 by disulfiram. Biochem Pharmacol 1997;54(12):1323-9
   PubMed Web of Science ®Google Scholar
• Eagling VA, Tjia JF, Back DJ. Differential selectivity of cytochrome P450 inhibitors against probe substrates in human and rat liver microsomes. Br J Clin Pharmacol 1998;45(2):107-14
   PubMed Web of Science ®Google Scholar
• Kharasch ED, Hankins DC, Jubert C, et al. Lack of single-dose disulfiram effects on cytochrome P-450 2C9, 2C19, 2D6, and 3A4 activities: evidence for specificity toward P-450 2E1. Drug Metab Dispos 1999;27(6):717-23
   PubMed Web of Science ®Google Scholar
• Frye RF, Branch RA. Effect of chronic disulfiram administration on the activities of CYP1A2, CYP2C19, CYP2D6, CYP2E1, and N-acetyltransferase in healthy human subjects. Br J Clin Pharmacol 2002;53(2):155-62
   PubMed Web of Science ®Google Scholar
• Sim E, Lack N, Wang CJ, et al. Arylamine N-acetyltransferases: structural and functional implications of polymorphisms. Toxicology 2008;254(3):170-83
   PubMed Web of Science ®Google Scholar
• Malka F, Dairou J, Ragunathan N, et al. Mechanisms and kinetics of human arylamine N-acetyltransferase 1 inhibition by disulfiram. FEBS J 2009;276(17):4900-8
   PubMed Web of Science ®Google Scholar
• Ragunathan N, Dairou J, Pluvinage B, et al. Identification of the xenobiotic-metabolizing enzyme arylamine N-acetyltransferase 1 as a new target of cisplatin in breast cancer cells: molecular and cellular mechanisms of inhibition. Mol Pharmacol 2008;73(6):1761-8
   PubMed Web of Science ®Google Scholar
• Adam PJ, Berry J, Loader JA, et al. Arylamine N-acetyltransferase-1 is highly expressed in breast cancers and conveys enhanced growth and resistance to etoposide in vitro. Mol Cancer Res 2003;1(11):826-35
   PubMed Web of Science ®Google Scholar
• Ploemen JP, van Iersel ML, Wormhoudt LW, et al. In vitro inhibition of rat and human glutathione S-transferase isoenzymes by disulfiram and diethyldithiocarbamate. Biochem Pharmacol 1996;52(2):197-204
   PubMed Web of Science ®Google Scholar
• Siddiqui A, Ali B, Srivastava SP. Effect of mancozeb on hepatic glutathione S-transferase in rat. Toxicol Lett 1993;68(3):301-5
   PubMed Web of Science ®Google Scholar
• Takahashi RN, Rogerio R, Zanin M. Maneb enhances MPTP neurotoxicity in mice. Res Commun Chem Pathol Pharmacol 1989;66(1):167-70
   PubMedGoogle Scholar
• Thiruchelvam M, Richfield EK, Baggs RB, et al. The nigrostriatal dopaminergic system as a preferential target of repeated exposures to combined paraquat and maneb: implications for Parkinson’s disease. J Neurosci 2000;20(24):9207-14
   PubMed Web of Science ®Google Scholar
• Costello S, Cockburn M, Bronstein J, et al. Parkinson’s disease and residential exposure to maneb and paraquat from agricultural applications in the central valley of California. Am J Epidemiol 2009;169(8):919-26
   PubMed Web of Science ®Google Scholar
• Sauna ZE, Shukla S, Ambudkar SV. Disulfiram, an old drug with new potential therapeutic uses for human cancers and fungal infections. Mol Biosyst 2005;1(2):127-34
   PubMed Web of Science ®Google Scholar
• Hoogenraad TU. Dithiocarbamates and Parkinson’s disease. Lancet 1988;1(8588):767
   PubMed Web of Science ®Google Scholar
• Fitzmaurice AG, Rhodes SL, Lulla A, et al. Aldehyde dehydrogenase inhibition as a pathogenic mechanism in Parkinson disease. Proc Natl Acad Sci USA 2013;110(2):636-41
   PubMed Web of Science ®Google Scholar
• Shen ML, Lipsky JJ, Naylor S. Role of disulfiram in the in vitro inhibition of rat liver mitochondrial aldehyde dehydrogenase. Biochem Pharmacol 2000;60(7):947-53
   PubMed Web of Science ®Google Scholar