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Chemical Compound Review

phorate     diethoxy- (ethylsulfanylmethylsulfanyl) ...

Synonyms: Granutox, Thimenox, Agrimet, Rampart, Foraat, ...
 
 
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Disease relevance of phorate

  • The deduced amino acid sequence showed 66.4% identity to the PepF oligopeptidase from Lactococcus lactis, a member of the M3 or thimet family of zinc metallopeptidases [1].
  • CONCLUSION: The observed statistical interaction suggests a gene-environment interaction between family history and phorate exposure in the incidence of prostate cancer, but other explanations are also possible [2].
  • RESULTS: Phorate use was not related to the incidence of all cancers combined or to any individual cancer, although we had insufficient numbers to study non-Hodgkin lymphoma or leukemia, which have been linked to organophosphates in other studies [2].
  • Characterization of thimet- and neurolysin-like activities in Escherichia coli M 3 A peptidases and description of a specific substrate [3].
  • Application of phorate recorded highest stimulation of fungi in laterite and actinomycetes in alluvial soil [4].
 

Psychiatry related information on phorate

  • Phorate (O,O-diethyl S-ethylthiomethyl phosphorodithioate) dissolved in aqueous solution was almost completely decomposed by ozonation to form various species within 10 minutes of reaction time for the experimental conditions examined in this research [5].
 

High impact information on phorate

  • The core protein sequence is encoded by exons 5-16 which match perfectly with exons 2-13 of the gene for endopeptidase 24.15, another member of the thimet oligopeptidase family [6].
  • Immunolocalization of thimet oligopeptidase in chicken embryonic fibroblasts [7].
  • The peptide derivative Dnp (2,4-dinitrophenyl)-Pro-Leu-Gly-Pro-DL-Amp-D-Lys was cleaved by thimet peptidase at the Leu-Gly bond, with a 20-fold enhancement of fluorescence [8].
  • BACKGROUND: We recently reported a link between use of the organophosphate pesticide phorate and risk of prostate cancer among applicators with a family history of prostate cancer in the Agricultural Health Study (AHS) [2].
  • The odds ratios for four organophosphate insecticides (terbufos, fonofos, chlorpyrifos, and phorate) were elevated when these chemicals were modeled individually and remained elevated, though attenuated somewhat, when chlorimuron-ethyl was included [9].
 

Chemical compound and disease context of phorate

  • Application of the insecticides stimulated the population of bacteria, actinomycetes and fungi in the rhizosphere soils, and the stimulation was more pronounced with phorate as compared to carbofuran [10].
 

Biological context of phorate

  • Mammalian thimet oligopeptidases, which were previously thought to participate in collagen degradation and share catalytic identities with Pz peptidases, were found to have lower identities in the overall primary sequence with Pz peptidases A and B but a significant resemblance in the vicinity of the catalytic site [11].
  • Cysteine residues potentially involved in dimerization were identified by modeling of thimet oliogopeptidase to its homolog, neurolysin [12].
  • M 3 A oligopeptidases from Escherichia coli, with hydrolytic properties similar to Zn-dependent mammalian thimet oligopeptidase (EP 24.15) and neurolysin (EP 24.16), were studied aiming at identification of comparative enzyme and substrate specificity, hydrolytic products, and susceptibility to inhibitors [3].
  • Significant cell cycle delays were only found in the treatments with the highest dose levels of butachlor, paraquat and phorate in CHO cells [13].
  • Except for phorate, all pesticides tested were clastogenic to CHO cells in the absence of in vitro metabolic activation by S9 [14].
 

Anatomical context of phorate

 

Associations of phorate with other chemical compounds

 

Gene context of phorate

  • In addition, FMO1 was shown to metabolize radiolabeled phorate, whereas FMO5 showed no activity toward phorate [20].
  • Mammalian mitochondrial intermediate peptidase: structure/function analysis of a new homologue from Schizophyllum commune and relationship to thimet oligopeptidases [21].
  • The Aspergillus fumigatus mepB gene encodes an 82 kDa intracellular metalloproteinase structurally related to mammalian thimet oligopeptidases [19].
  • Analysis of the deduced amino acid sequence of mepB showed that the MepB protein is a cytosolic zinc metalloproteinase of the thimet oligopeptidase family (M3) and as such is probably involved in the intracellular degradation of small peptides [19].
  • Biochemical and histopathological changes in serum and liver of the male Swiss Albino mouse, Mus musculus, exposed subchronically to the recommended field dose of Thimet (6728.5 mg m(-3)) in a whole body inhalation chamber were studied in the second, fourth, sixth, eighth, tenth and twelfth week of exposure [22].
 

Analytical, diagnostic and therapeutic context of phorate

  • The HPLC analysis of phorate in bioaugmented soil revealed its complete disappearance within 40 days [23].
  • Confocal microscopy reveals thimet oligopeptidase (EC 3.4.24.15) and neurolysin (EC 3.4.24.16) in the classical secretory pathway [24].
  • Exposure of 40 formulators to a highly toxic OP insecticide (phorate) showed that over 60% of the workers suffered from toxic effects in spite of using a complete set of protective clothing [25].
  • Confirmation of phorate, terbufos, and their sulfoxides and sulfones in water by capillary gas chromatography/chemical ionization mass spectrometry [26].
  • Combining the analytical results by various instruments, including gas chromatograph equipped with an electron ionization detector (GC-EID), high performance liquid chromatography (HPLC), ion chromatography (IC), and total organic carbon (TOC), the temporal sequence of phorate ozonation was proposed in this study [5].

References

  1. Characterization of PepB, a group B streptococcal oligopeptidase. Lin, B., Averett, W.F., Novak, J., Chatham, W.W., Hollingshead, S.K., Coligan, J.E., Egan, M.L., Pritchard, D.G. Infect. Immun. (1996) [Pubmed]
  2. Phorate exposure and incidence of cancer in the agricultural health study. Mahajan, R., Bonner, M.R., Hoppin, J.A., Alavanja, M.C. Environ. Health Perspect. (2006) [Pubmed]
  3. Characterization of thimet- and neurolysin-like activities in Escherichia coli M 3 A peptidases and description of a specific substrate. Paschoalin, T., Carmona, A.K., Oliveira, V., Juliano, L., Travassos, L.R. Arch. Biochem. Biophys. (2005) [Pubmed]
  4. A comparative study on the dissipation and microbial metabolism of organophosphate and carbamate insecticides in orchaqualf and fluvaquent soils of West Bengal. Das, A.C., Chakravarty, A., Sen, G., Sukul, P., Mukherjee, D. Chemosphere (2005) [Pubmed]
  5. Decomposition of phorate in aqueous solution by ozonation. Ku, Y., Lin, H.S., Wang, W., Ma, C.M. Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes (2007) [Pubmed]
  6. Targeting of endopeptidase 24.16 to different subcellular compartments by alternative promoter usage. Kato, A., Sugiura, N., Saruta, Y., Hosoiri, T., Yasue, H., Hirose, S. J. Biol. Chem. (1997) [Pubmed]
  7. Immunolocalization of thimet oligopeptidase in chicken embryonic fibroblasts. Chen, J.M., Changco, A., Brown, M.A., Barrett, A.J. Exp. Cell Res. (1995) [Pubmed]
  8. A quenched fluorescent substrate for thimet peptidase containing a new fluorescent amino acid, DL-2-amino-3-(7-methoxy-4-coumaryl)propionic acid. Knight, C.G. Biochem. J. (1991) [Pubmed]
  9. Pesticides associated with wheeze among commercial pesticide applicators in the Agricultural Health Study. Hoppin, J.A., Umbach, D.M., London, S.J., Lynch, C.F., Alavanja, M.C., Sandler, D.P. Am. J. Epidemiol. (2006) [Pubmed]
  10. Influence and persistence of phorate and carbofuran insecticides on microorganisms in rice field. Das, A.C., Chakravarty, A., Sukul, P., Mukherjee, D. Chemosphere (2003) [Pubmed]
  11. Two thimet oligopeptidase-like Pz peptidases produced by a collagen-degrading thermophile, Geobacillus collagenovorans MO-1. Miyake, R., Shigeri, Y., Tatsu, Y., Yumoto, N., Umekawa, M., Tsujimoto, Y., Matsui, H., Watanabe, K. J. Bacteriol. (2005) [Pubmed]
  12. Involvement of surface cysteines in activity and multimer formation of thimet oligopeptidase. Sigman, J.A., Sharky, M.L., Walsh, S.T., Pabon, A., Glucksman, M.J., Wolfson, A.J. Protein Eng. (2003) [Pubmed]
  13. Induction of sister-chromatid exchanges by pesticides in primary rat tracheal epithelial cells and Chinese hamster ovary cells. Wang, T.C., Lee, T.C., Lin, M.F., Lin, S.Y. Mutat. Res. (1987) [Pubmed]
  14. Pesticide clastogenicity in Chinese hamster ovary cells. Lin, M.F., Wu, C.L., Wang, T.C. Mutat. Res. (1987) [Pubmed]
  15. Regulators of the neuropeptide-degrading enzyme, EC 3.4.24.15 (thimet oligopeptidase), in cerebrospinal fluid. Shrimpton, C.N., Wolfson, A.J., Smith, A.I., Lew, R.A. J. Neurosci. Res. (2003) [Pubmed]
  16. A distinct thimet peptidase from rat liver mitochondria. Tisljar, U., Barrett, A.J. FEBS Lett. (1990) [Pubmed]
  17. Histopathological and biochemical changes in the liver and testes of desert gerbil, after repeated exposures of Thimet (phorate). Saxena, A.K., Sarin, K. Toxicology (1980) [Pubmed]
  18. S-oxygenation of the thioether organophosphate insecticides phorate and disulfoton by human lung flavin-containing monooxygenase 2. Henderson, M.C., Krueger, S.K., Siddens, L.K., Stevens, J.F., Williams, D.E. Biochem. Pharmacol. (2004) [Pubmed]
  19. The Aspergillus fumigatus mepB gene encodes an 82 kDa intracellular metalloproteinase structurally related to mammalian thimet oligopeptidases. Ibrahim-Granet, O., D'Enfert, C. Microbiology (Reading, Engl.) (1997) [Pubmed]
  20. Molecular cloning, sequence, and expression of mouse flavin-containing monooxygenases 1 and 5 (FMO1 and FMO5). Cherrington, N.J., Falls, J.G., Rose, R.L., Clements, K.M., Philpot, R.M., Levi, P.E., Hodgson, E. J. Biochem. Mol. Toxicol. (1998) [Pubmed]
  21. Mammalian mitochondrial intermediate peptidase: structure/function analysis of a new homologue from Schizophyllum commune and relationship to thimet oligopeptidases. Isaya, G., Sakati, W.R., Rollins, R.A., Shen, G.P., Hanson, L.C., Ullrich, R.C., Novotny, C.P. Genomics (1995) [Pubmed]
  22. Inhalation toxicity studies of thimet (phorate) in male Swiss albino mouse, Mus musculus: I. Hepatotoxicity. Morowati, M. Environ. Pollut. (1997) [Pubmed]
  23. Isolation and characterization of phorate degrading soil bacteria of environmental and agronomic significance. Bano, N., Musarrat, J. Lett. Appl. Microbiol. (2003) [Pubmed]
  24. Confocal microscopy reveals thimet oligopeptidase (EC 3.4.24.15) and neurolysin (EC 3.4.24.16) in the classical secretory pathway. Garrido, P.A., Vandenbulcke, F., Ramjaun, A.R., Vincent, B., Checler, F., Ferro, E., Beaudet, A. DNA Cell Biol. (1999) [Pubmed]
  25. Health surveillance and biological monitoring of pesticide formulators in India. Kashyap, S.K. Toxicol. Lett. (1986) [Pubmed]
  26. Confirmation of phorate, terbufos, and their sulfoxides and sulfones in water by capillary gas chromatography/chemical ionization mass spectrometry. Stout, S.J., daCunha, A.R., Boyd, J.E., Devine, J.M. Journal - Association of Official Analytical Chemists. (1989) [Pubmed]
 
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