Role of CYP2E1-mediated metabolism in the acute and vestibular toxicities of nineteen nitriles in the mouse

Toxicology Letters

Volumn 208, Issue 2, 2012, Pages 125-132

  Saldaña Ruíz, Sandra ^a,b   Soler Martín, Carla ^a,b   Llorens, Jordi ^a,b  

^a UNIVERSITY OF BARCELONA   (Spain)

^b BELLVITGE BIOMEDICAL RESEARCH INSTITUTE IDIBELL   (Spain)

Author keywords

Acute toxicity test protocol; CYP2E1; Nitrile; Ototoxicity; Vestibular toxicity; Xenobiotic metabolism

Indexed keywords

2 CYANOETHANOL; 2 METHYBUTYRONITRILE; 2 PENTENENITRILE; 3 (DIMETHYLAMINO)PROPIONITRILE; 3 AMINOCROTONONITRILE; 3 DIMETHYLAMINOACRYLONITRILE; 3 HYDROXYBUTYRONITRILE; 3 METHYLAMINOPROPIONITRILE; 3 PENTENENITRILE; 3,3' IMINODIPROPIONITRILE; ALLYL CYANIDE; BUTANONE CYANOHYDRIN; BUTYRONITRILE; CROTONONITRILE; CYTOCHROME P450 2E1; HEXADIENENITRILE; ISOBUTYRONITRILE; LINAMARIN; NITRILE; PROPIONALDEHYDE CYANOHYDRIN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; DISEASE PREDISPOSITION; FEMALE; LD 50; MALE; MOUSE; NEUROTOXICITY; NONHUMAN; OTOTOXICITY; PRIORITY JOURNAL; PROTEIN FUNCTION; PROTEIN METABOLISM; TOXICITY TESTING; VESTIBULAR TOXICITY;

ANIMALS; CYTOCHROME P-450 CYP2E1; DOSE-RESPONSE RELATIONSHIP, DRUG; FEMALE; MALE; MICE; MICE, MUTANT STRAINS; NITRILES; VESTIBULE, LABYRINTH;

ANIMALIA; MUS; RATTUS; RODENTIA;

EID: 81255195896     PISSN: 03784274     EISSN: 18793169     Source Type: Journal    
DOI: 10.1016/j.toxlet.2011.10.016     Document Type: Article

References (42)

1. Balbuena E., Llorens J. Behavioural disturbances and sensory pathology following allylnitrile exposure in rats. Brain Res. 2001, 904:298-306.
2. Balbuena E., Llorens J. Comparison of cis- and trans-crotononitrile effects in the rat reveals specificity in the neurotoxic properties of nitrile isomers. Toxicol. Appl. Pharmacol. 2003, 187:89-100.
3. Benz F.W., Nerland D.E. Effect of cytochrome P450 inhibitors and anticonvulsants on the acute toxicity of acrylonitrile. Arch. Toxicol. 2005, 79:610-614.
4. Benz F.W., Nerland D.E., Li J., Corbett D. Dose dependence of covalent binding of acrylonitrile to tissue protein and globin in rats. Fundam. Appl. Toxicol. 1997, 36:149-156.
5. Boadas-Vaello P., Riera J., Llorens J. Behavioral and pathological effects in the rat define two groups of neurotoxic nitriles. Toxicol. Sci. 2005, 88:456-466.
6. Boadas-Vaello P., Jover E., Díez-Padrisa N., Bayona J.M., Llorens J. Differential role of CYP2E1-mediated metabolism in the lethal and vestibulotoxic effects of cis-crotononitrile in the mouse. Toxicol. Appl. Pharmacol. 2007, 225:310-317.
7. Boadas-Vaello P., Jover E., Saldaña-Ruíz S., Soler-Martín C., Chabbert C., Bayona J.M., Llorens J. Allylnitrile metabolism by CYP2E1 and other CYPs leads to distinct lethal and vestibulotoxic effects in the mouse. Toxicol. Sci. 2009, 107:461-472.
8. Chanas B., Wang H., Ghanayem B.I. Differential metabolism of acrylonitrile to cyanide is responsible for the greater sensitivity of male vs female mice: role of CYP2E1 and epoxide hydrolases. Toxicol. Appl. Pharmacol. 2003, 193:293-302.
9. Crofton K.M., Knight T. Auditory deficits and motor dysfunction following iminodipropionitrile administration in the rat. Neurotoxicol. Teratol. 1991, 13:575-581.
10. Crofton K.M., Janssen R., Prazma J., Pulver S., Barone S. The ototoxicity of 3,3'-iminodipropionitrile: functional and morphological evidence of cochlear damage. Hear. Res. 1994, 80:129-140.
11. Delay J., Pichot P., Thuillier J., Marquiset J.P. Action de l'amino-dipropionitrile sur le comportement moteur de la souris blanche. C. R. Soc. Biol. 1952, 146:533-534.
12. DeVito S.C. Designing safer nitriles. Designing Safer Chemicals 1996, 194-223. American Chemical Society, Washington, DC. S.C. DeVito, R.L. Garrett (Eds.).
13. DeVito, S. C. 2007. Nitriles. Kirk-Othmer Encyclopedia of Chemical Technology. DOI:10.1002/0471238961.1409201813031109.
14. El Hadri L., Chanas B., Ghanayem B.I. Comparative metabolism of methacrylonitrile and acrylonitrile to cyanide using cytochrome P4502E1 and microsomal epoxide hydrolase-null mice. Toxicol. Appl. Pharmacol. 2005, 205:116-125.
15. Fechter L.D. Promotion of noise-induced hearing loss by chemical contaminants. J. Toxicol. Environ. Health A 2004, 67:727-740.
16. Fechter L.D., Klis S.F.L., Shirwany N.A., Moore T.G., Rao D.B. Acrylonitrile produces transient cochlear function loss and potentiates permanent noise-induced hearing loss. Toxicol. Sci. 2003, 75:117-123.
17. Gagnaire F., Marignac B., Ban M., Langlais C. The ototoxic effects induced in rats by treatment for 12 weeks with 2-butenenitrile, 3-butenenitrile and cis-2-pentenenitrile. Pharmacol. Toxicol. 2001, 88:126-134.
18. Ghanayem B.I., Sanders J.M., Chanas B., Burka L.T., Gonzalez F.J. Role of cytochrome P-450 2E1 in methacrylonitrile metabolism and disposition. J. Pharmacol. Exp. Ther. 1999, 289:1054-1059.
19. Genter M.B., Deamer N.J., Cao Y., Levi P.E. Effects of P450 inhibition and induction on the olfactory toxicity of β,β'-iminodipropionitrile (IDPN) in the rat. J. Biochem. Toxicol. 1994, 9:31-39.
20. Grogan J., DeVito S.C., Pearlman R.S., Korzekwa K.R. Modeling cyanide release from nitriles: prediction of cytochrome P450 mediated acute nitrile toxicity. Chem. Res. Toxicol. 1992, 5:548-552.
21. Khan H.A., Alhomida A.S., Arif I.A. Neurovestibular toxicities of acrylonitrile and iminodipropionitrile in rats: a comparative evaluation of putative mechanisms and target sites. Toxicol. Sci. 2009, 109:124-129.
22. Lee S.S., Buters J.T., Pineau T., Fernandez-Salguero P., Gonzalez F.J. Role of CYP2E1 in the hepatotoxicity of acetaminophen. J. Biol. Chem. 1996, 271:12063-12067.
23. Lewis D.F.V., Ioannides C., Parke D.V. Interaction of a series of nitriles with the alcohol-inducible isoform of P450: computer analysis of structure-activity relationships. Xenobiotica 1994, 24:401-408.
24. Llorens J., Demêmes D., Sans A. The behavioral syndrome caused by 3,3'-iminodipropionitrile and related nitriles in the rat is associated with degeneration of the vestibular sensory hair cells. Toxicol. Appl. Pharmacol. 1993, 123:199-210.
25. Llorens J., Rodríguez-Farré E. Comparison of behavioral, vestibular, and axonal effects of subchronic IDPN in the rat. Neurotoxicol. Teratol. 1997, 19:117-127.
26. Llorens J., Aguiló A., Rodríguez-Farré E. Behavioral disturbances and vestibular pathology following crotonitrile exposure in rats. J. Peripher. Nerv. Syst. 1998, 3:189-196.
27. Llorens J., Soler-Martín C., Saldaña-Ruíz S., Cutillas B., Ambrosio S., Boadas-Vaello P. A new unifying hypothesis for lathyrism, konzo and tropical ataxic neuropathy: nitriles are the causative agents. Food Chem. Toxicol. 2011, 49:563-570.
28. Moser V.C., Boyes W.K. Prolonged neurobehavioral and visual effects of short-term exposure to 3,3'-iminodipropionitrile (IDPN) in rats. Fundam. Appl. Toxicol. 1993, 21:277-290.
29. Ohkawa H., Ohkawa R., Yamamoto I., Casida J.E. Enzymatic mechanisms and toxicological significance of hydrogen cyanide liberation from various organothiocyanates and organonitriles in mice and houseflies. Pestic. Biochem. Physiol. 1972, 2:95-112.
30. Pouyatos B., Gearhart C., Nelson-Miller A., Fulton S., Fechter L. Oxidative stress pathways in the potentiation of noise-induced hearing loss by acrylonitrile. Hear. Res. 2007, 224:61-74.
31. Seoane A., Apps R., Balbuena E., Herrero L., Llorens J. Differential effects of trans-crotononitrile and 3-acetylpyridine on inferior olive integrity and behavioural performance in the rat. Eur. J. Neurosci. 2005, 22:880-894.
32. Seoane A., Demêmes D., Llorens J. Relationship between insult intensity and mode of hair cell loss in the vestibular system of rats exposed to 3,3'-iminodipropionitrile. J. Comp. Neurol. 2001, 439:385-399.
33. Soler-Martín C., Diez-Padrisa N., Boadas-Vaello P., Llorens J. Behavioral disturbances and hair cell loss in the inner ear following nitrile exposure in mice, guinea pigs, and frogs. Toxicol. Sci. 2007, 96:123-132.
34. Soria A.C., Martínez-Castro I., de Lorenzo C., Sanz J. Occurrence of nitriles in Taraxacum labelled honeys. Food Chem. 2008, 107:439-443.
35. Suhua W., Rongzhu L., Wenrong X., Guangwei X., Xiaowu Z., Shizhong W., Ye Z., Fangan H., Aschner M. Induction or inhibition of cytochrome P450 2E1 modifies the acute toxicity of acrylonitrile in rats: biochemical evidence. Arch. Toxicol. 2010, 84:461-469.
36. Tanii H., Hashimoto K. Studies on the mechanism of acute toxicity of nitriles in mice. Arch. Toxicol. 1984, 55:47-54.
37. Tanii H., Hashimoto K. Influence of ethanol on the in vivo and in vitro metabolism of nitriles in mice. Arch. Toxicol. 1986, 58:171-176.
38. Tanii H., Hayashi M., Hashimoto K. Nitrile-induced behavioral abnormalities in mice. Neurotoxicology 1989, 10:157-165.
39. Tanii H., Kurosaka Y., Hayashi M., Hashimoto K. Allylnitrile: a compound which induces long-term dyskinesia in mice following a single administration. Exp. Neurol. 1989, 103:64-67.
40. Tanii H., Takayasu T., Higashi T., Leng S., Saijoh K. Allylnitrile: generation from cruciferous vegetables and behavioral effects on mice of repeated exposure. Food Chem. Toxicol. 2004, 42:453-458.
41. Wang H., Chanas B., Ghanayem B.I. Cytochrome P450 2E1 (CYP2E1) is essential for acrylonitrile metabolism to cyanide: comparative studies using CYP2E1-null and wild-type mice. Drug Metab. Dispos. 2002, 30:911-917.
42. Willhite C.C., Smith R.P. The role of cyanide liberation in the acute toxicity of aliphatic nitriles. Toxicol. Appl. Pharmacol. 1981, 59:589-602.