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Chemical Compound Review

toluene     methylbenzene

Synonyms: Tolueen, Tolueno, Toluolo, methacide, Anisen, ...
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Disease relevance of toluene

  • Transposition of Pseudomonas toluene-degrading genes and expression in Escherichia coli [1].
  • Toxic effects of toluene: a new cause of high anion gap metabolic acidosis [2].
  • Although epithelial hyperplasia induced by BP was interpreted as a preneoplastic lesion, no ultrastructural differences were detected between T- and BP-treated mice in any environment [3].
  • Upon expression in Escherichia coli, some of these evolved genes exhibited enhanced degradation capacity, not only for PCB and related biphenyl compounds, but for single aromatic hydrocarbons such as benzene and toluene, which are poor substrates for the original BP Dox [4].
  • We introduced the pTOM toluene-degradation plasmid of Burkholderia cepacia G4 into B. cepacia L.S.2.4, a natural endophyte of yellow lupine [5].

Psychiatry related information on toluene

  • The ratio of 1,4-BQ-Alb:BO-Alb decreased with age and coexposure to toluene, and increased with alcohol consumption [6].
  • We studied the ocular motor abnormalities in 4 patients chronically addicted to sniffing glue containing toluene [7].
  • Dementia in toluene abuse appears to be related to severity of cerebral white matter involvement [8].
  • Enhanced performance is characterized by a wider operational temperature range (-10 to +50 degrees C) over which the sensors displayed, concurrently, an analyte sensitivity of >0.2 Hz/ppm toluene, minimal energy loss (resistance <120 ohms), and response times of <20 min (time required to reach 90% of full response) [9].
  • In the toluene group thoughts were more likely to be slowed, time appeared to pass more quickly and tactile hallucinations were more commonly reported than in the butane group [10].

High impact information on toluene


Chemical compound and disease context of toluene


Biological context of toluene

  • The present studies address the mechanism of aromatic hydroxylation used by the natural and G103L isoforms of the diiron enzyme toluene 4-monooxygenase [20].
  • The genetic organization of the Pseudomonas putida plasmid pWWO-161, which encodes enzymes for the degradation of toluene and related aromatic hydrocarbons, has been investigated by transposition mutagenesis and gene cloning [21].
  • That is, the toluene-treated vesicles showed only V1 for MeGlc phosphorylation [22].
  • The gene cluster adjacent to the sequence of rpoN (encoding sigma factor sigma54) of Pseudomonas putida has been studied with respect to the C source regulation of the Pu promoter of the upper TOL (toluene catabolism) operon [23].
  • The 2-hydroxymuconic semialdehyde hydrolase, XylF, of the Pseudomonas putida TOL plasmid-encoded pathway for the catabolism of toluene and xylenes, catalyzes one of the rarest types of enzyme reaction (EC, the hydrolysis of a carbon-carbon bond in its substrate, the ring-fission product of 3-alkyl-substituted catechols [24].

Anatomical context of toluene

  • Toluene abuse causes diffuse central nervous system white matter changes [25].
  • The findings confirm a previous report of a toluene-induced neurological syndrome that is exclusively central, sparing peripheral nerves [26].
  • Taken in concert, these findings suggest that the pathological and MRI abnormalities are due to either increased water content of the white matter or subtle toluene-induced metabolic changes in myelin [25].
  • Preparation and characterization of liver cells made permeable to macromolecules by treatment with toluene [27].
  • Mutants unable to carry out cis --> trans isomerization of unsaturated lipids, that exhibit altered cell envelopes because of the lack of the OprL protein, or that are unable to exclude toluene from cell membranes are hypersensitive to toluene [28].

Associations of toluene with other chemical compounds


Gene context of toluene

  • Time course of IL1 and IL6 synthesis and release in human bronchial epithelial cell cultures exposed to toluene diisocyanate [32].
  • These results may explain, in part, the lower activity of CYP2B6, which has Phe at position 58 of the protein, for toluene ring oxidations than that of CYP2B1 [33].
  • Although CYP1A2 appears to be responsible for the formation of the minor (phenolic) metabolites of toluene and the xylene isomers, CYP2E1 catalyzed methylhydroxylation will be the major determinant of the clearance of these compounds in humans [34].
  • Neonatal toluene exposure alters N-methyl-D-aspartate receptor subunit expression in the hippocampus and cerebellum in juvenile rats [35].
  • Immunohistochemical analysis with confocal imaging showed that toluene-treated neurons had significant increases in the density of NR1 subunits as compared with control neurons [36].

Analytical, diagnostic and therapeutic context of toluene


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  2. Toxic effects of toluene: a new cause of high anion gap metabolic acidosis. Fischman, C.M., Oster, J.R. JAMA (1979) [Pubmed]
  3. Effect of temperature on benzo[a]pyrene-induced hyperplastic and neoplastic skin lesions in mice. Weisbrode, S.E., Weiss, H.S. J. Natl. Cancer Inst. (1981) [Pubmed]
  4. Enhanced degradation of polychlorinated biphenyls by directed evolution of biphenyl dioxygenase. Kumamaru, T., Suenaga, H., Mitsuoka, M., Watanabe, T., Furukawa, K. Nat. Biotechnol. (1998) [Pubmed]
  5. Engineered endophytic bacteria improve phytoremediation of water-soluble, volatile, organic pollutants. Barac, T., Taghavi, S., Borremans, B., Provoost, A., Oeyen, L., Colpaert, J.V., Vangronsveld, J., van der Lelie, D. Nat. Biotechnol. (2004) [Pubmed]
  6. Albumin adducts of benzene oxide and 1,4-benzoquinone as measures of human benzene metabolism. Rappaport, S.M., Waidyanatha, S., Qu, Q., Shore, R., Jin, X., Cohen, B., Chen, L.C., Melikian, A.A., Li, G., Yin, S., Yan, H., Xu, B., Mu, R., Li, Y., Zhang, X., Li, K. Cancer Res. (2002) [Pubmed]
  7. Acquired pendular nystagmus in toluene addiction. Maas, E.F., Ashe, J., Spiegel, P., Zee, D.S., Leigh, R.J. Neurology (1991) [Pubmed]
  8. White matter dementia in chronic toluene abuse. Filley, C.M., Heaton, R.K., Rosenberg, N.L. Neurology (1990) [Pubmed]
  9. Thin films of block copolymer blends for enhanced performance of acoustic wave-based chemical sensors. Lipert, R.J., Shinar, R., Vaidya, B., Pris, A.D., Porter, M.D., Liu, G., Grabau, T.D., Dilger, J.P. Anal. Chem. (2002) [Pubmed]
  10. Phenomenology of intoxication with toluene-based adhesives and butane gas. Evans, A.C., Raistrick, D. The British journal of psychiatry : the journal of mental science. (1987) [Pubmed]
  11. Long-term mortality study of oil refinery workers. IV. Exposure to the lubricating-dewaxing process. Wen, C.P., Tsai, S.P., Weiss, N.S., Gibson, R.L., Wong, O., McClellan, W.A. J. Natl. Cancer Inst. (1985) [Pubmed]
  12. Engineering Deinococcus radiodurans for metal remediation in radioactive mixed waste environments. Brim, H., McFarlan, S.C., Fredrickson, J.K., Minton, K.W., Zhai, M., Wackett, L.P., Daly, M.J. Nat. Biotechnol. (2000) [Pubmed]
  13. Hypersensitivity pneumonitis induced by toluene diisocyanate: sequelae of continuous exposure. Yoshizawa, Y., Ohtsuka, M., Noguchi, K., Uchida, Y., Suko, M., Hasegawa, S. Ann. Intern. Med. (1989) [Pubmed]
  14. Hypersensitivity pneumonitis and toluene diisocyanate. Grammer, L. Ann. Intern. Med. (1989) [Pubmed]
  15. Glucose-sensitive adenylate cyclase in toluene-treated cells of Escherichia coli B. Harwood, J.P., Peterkofsky, A. J. Biol. Chem. (1975) [Pubmed]
  16. Xylene monooxygenase catalyzes the multistep oxygenation of toluene and pseudocumene to corresponding alcohols, aldehydes, and acids in Escherichia coli JM101. Bühler, B., Schmid, A., Hauer, B., Witholt, B. J. Biol. Chem. (2000) [Pubmed]
  17. Active site engineering of the epoxide hydrolase from Agrobacterium radiobacter AD1 to enhance aerobic mineralization of cis-1,2-dichloroethylene in cells expressing an evolved toluene ortho-monooxygenase. Rui, L., Cao, L., Chen, W., Reardon, K.F., Wood, T.K. J. Biol. Chem. (2004) [Pubmed]
  18. Synthesis and degradation of poly(A) in permeable cells of Escherichia coli. Deutscher, M.P. J. Biol. Chem. (1978) [Pubmed]
  19. Mediator release during nasal provocation. A model to investigate the pathophysiology of rhinitis. Togias, A., Naclerio, R.M., Proud, D., Baumgarten, C., Peters, S., Creticos, P.S., Warner, J., Kagey-Sobotka, A., Adkinson, N.F., Norman, P.S. Am. J. Med. (1985) [Pubmed]
  20. Insight into the mechanism of aromatic hydroxylation by toluene 4-monooxygenase by use of specifically deuterated toluene and p-xylene. Mitchell, K.H., Rogge, C.E., Gierahn, T., Fox, B.G. Proc. Natl. Acad. Sci. U.S.A. (2003) [Pubmed]
  21. Molecular and functional analysis of the TOL plasmid pWWO from Pseudomonas putida and cloning of genes for the entire regulated aromatic ring meta cleavage pathway. Franklin, F.C., Bagdasarian, M., Bagdasarian, M.M., Timmis, K.N. Proc. Natl. Acad. Sci. U.S.A. (1981) [Pubmed]
  22. Kinetic characterization and regulation of phosphoenolpyruvate-dependent methyl alpha-D-glucopyranoside transport by Salmonella typhimurium membrane vesicles. Liu, K.D., Roseman, S. Proc. Natl. Acad. Sci. U.S.A. (1983) [Pubmed]
  23. The IIANtr (PtsN) protein of Pseudomonas putida mediates the C source inhibition of the sigma54-dependent Pu promoter of the TOL plasmid. Cases, I., Pérez-Martín, J., de Lorenzo, V. J. Biol. Chem. (1999) [Pubmed]
  24. Identification of functional residues in a 2-hydroxymuconic semialdehyde hydrolase. A new member of the alpha/beta hydrolase-fold family of enzymes which cleaves carbon-carbon bonds. Díaz, E., Timmis, K.N. J. Biol. Chem. (1995) [Pubmed]
  25. Toluene abuse causes diffuse central nervous system white matter changes. Rosenberg, N.L., Kleinschmidt-DeMasters, B.K., Davis, K.A., Dreisbach, J.N., Hormes, J.T., Filley, C.M. Ann. Neurol. (1988) [Pubmed]
  26. Persistent cerebellar ataxia after exposure to toluene. Boor, J.W., Hurtig, H.I. Ann. Neurol. (1977) [Pubmed]
  27. Preparation and characterization of liver cells made permeable to macromolecules by treatment with toluene. Hilderman, R.H., Goldblatt, P.J., Deutscher, M.P. J. Biol. Chem. (1975) [Pubmed]
  28. Mechanisms for solvent tolerance in bacteria. Ramos, J.L., Duque, E., Rodríguez-Herva, J.J., Godoy, P., Haïdour, A., Reyes, F., Fernández-Barrero, A. J. Biol. Chem. (1997) [Pubmed]
  29. Energy barriers in binding of carbon monoxide and oxygen to heme model compounds. Tetreau, C., Lavalette, D., Momenteau, M., Lhoste, J.M. Proc. Natl. Acad. Sci. U.S.A. (1987) [Pubmed]
  30. Greatly decreased susceptibility of nonmetabolizing cells towards detergents. Komor, E., Weber, H., Tanner, W. Proc. Natl. Acad. Sci. U.S.A. (1979) [Pubmed]
  31. The broad substrate chlorobenzene dioxygenase and cis-chlorobenzene dihydrodiol dehydrogenase of Pseudomonas sp. strain P51 are linked evolutionarily to the enzymes for benzene and toluene degradation. Werlen, C., Kohler, H.P., van der Meer, J.R. J. Biol. Chem. (1996) [Pubmed]
  32. Time course of IL1 and IL6 synthesis and release in human bronchial epithelial cell cultures exposed to toluene diisocyanate. Mattoli, S., Colotta, F., Fincato, G., Mezzetti, M., Mantovani, A., Patalano, F., Fasoli, A. J. Cell. Physiol. (1991) [Pubmed]
  33. Toluene metabolism by cDNA-expressed human hepatic cytochrome P450. Nakajima, T., Wang, R.S., Elovaara, E., Gonzalez, F.J., Gelboin, H.V., Raunio, H., Pelkonen, O., Vainio, H., Aoyama, T. Biochem. Pharmacol. (1997) [Pubmed]
  34. Human cytochrome P450 isoform specificity in the regioselective metabolism of toluene and o-, m- and p-xylene. Tassaneeyakul, W., Birkett, D.J., Edwards, J.W., Veronese, M.E., Tassaneeyakul, W., Tukey, R.H., Miners, J.O. J. Pharmacol. Exp. Ther. (1996) [Pubmed]
  35. Neonatal toluene exposure alters N-methyl-D-aspartate receptor subunit expression in the hippocampus and cerebellum in juvenile rats. Lee, Y.F., Lo, P.S., Wang, Y.J., Hu, A., Chen, H.H. Neuropharmacology (2005) [Pubmed]
  36. Alterations in glutamatergic and gabaergic ion channel activity in hippocampal neurons following exposure to the abused inhalant toluene. Bale, A.S., Tu, Y., Carpenter-Hyland, E.P., Chandler, L.J., Woodward, J.J. Neuroscience (2005) [Pubmed]
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