Investigating the role of 2-phenylpropenal in felbamate-induced idiosyncratic drug reactions

Chemical Research in Toxicology

Volumn 17, Issue 12, 2004, Pages 1568-1576

  Popovic M ^a   Nierkens, S ^c   Pieters, R ^c   Uetrecht, J ^a,b  

^a UNIVERSITY OF TORONTO   (Canada)

^b UNIVERSITY OF TORONTO   (Canada)

^c UTRECHT UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

2 PHENYL 1,3 PROPANEDIOL CARBAMATE; 2 PHENYLPROPENAL; 3 CARBAMOYL 2 PHENYLPROPIONALDEHYDE; ACROLEIN; AMMONIA; ANTIGEN; CARBON DIOXIDE; CYTOKINE; FELBAMATE; GAMMA INTERFERON; IMMUNOGLOBULIN G1 ANTIBODY; IMMUNOGLOBULIN M ANTIBODY; INTERCELLULAR ADHESION MOLECULE 1; INTERLEUKIN 4; LYMPHOCYTE SURFACE MARKER; POLYCLONAL ANTIBODY; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTIBODY PRODUCTION; APLASTIC ANEMIA; ARTICLE; B LYMPHOCYTE; BONE MARROW TOXICITY; CELL COUNT; CONTROLLED STUDY; COVALENT BOND; CYTOKINE PRODUCTION; DRUG HYDROLYSIS; DRUG INDUCED DISEASE; DRUG MECHANISM; ENZYME LINKED IMMUNOSORBENT ASSAY; FLOW CYTOMETRY; FOOT PAD; GERMINAL CENTER; IMMUNE MEDIATED INJURY; IMMUNE RESPONSE; IMMUNOBLOTTING; IMMUNOGENICITY; IMMUNOHISTOCHEMISTRY; INFLAMMATION; LIVER TOXICITY; LYMPH NODE; LYMPH NODE CELL; LYMPHOCYTE PROLIFERATION; MOUSE; NONHUMAN; POPLITEAL ARTERY; POPLITEAL LYMPH NODE; RAT; RODENT;

ALDEHYDES; ANEMIA, APLASTIC; ANIMALS; ANTICONVULSANTS; FEMALE; IMMUNOGLOBULIN G; IMMUNOGLOBULIN M; IMMUNOHISTOCHEMISTRY; INTERFERON TYPE II; INTERLEUKIN-4; LIVER; LIVER DISEASES; LYMPH NODES; MICE; MODELS, ANIMAL; PROPYLENE GLYCOLS;

ANIMALIA; MINK CELL FOCUS-FORMING VIRUS; RODENTIA;

EID: 10844281990     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx0498197     Document Type: Article

References (22)

1. O'Neil, M. G., Perdun, C. S., Wilson, M. B., McGown, S. T., and Patel, S. (1996) Felbamate-associated fatal acute hepatic necrosis. Neurology 46, 1457-1459.
2. Kaufman, D. W., Kelly, J. P., Anderson, T., Harmon, D. C., and Shapiro, S. (1997) Evaluation of case reports of aplastic anemia among patients treated with felbamate. Epilepsia 38, 1265-1269.
3. Nightingale, S. L. (1994) From the Food and Drug Administration. J. Am. Med. Assoc. 272, 995.
4. Pirmohamed, M., Breckenridge, A. M., Kitteringham, N. R., and Park, B. K. (1998) Adverse drug reactions. Br. Med. J. 316, 1295-1298.
5. Park, B. K., Pirmohamed, M., and Kitteringham, N. R. (1998) Role of drug disposition in drug hypersensitivity: A chemical, molecular, and clinical perspective. Chem. Res. Toxicol. 11, 969-988.
6. Thompson, C. D., Kinter, M. T., and Macdonald, T. L. (1996) Synthesis and in vitro reactivity of 3-carbamoyl-2-phenylpropionaldehyde and 2-phenylpropenal: Putative reactive metabolites of felbamate. Chem. Res. Toxicol. 9, 1225-1229.
7. Dieckhaus, C. M., Miller, T. A., Sofia, R. D., and Macdonald, T. L. (2000) A mechanistic approach to understanding species differences in felbamate bioactivation: Relevance to drug-induced idiosyncratic reactions. Drug Metab. Dispos. 28, 814-822.
8. Alexopoulou, L., Holt, A. C., Medzhitov, R., and Flavell, R. A. (2001) Recognition of double-stranded RNA and activation of NF-kappaB by Toll-like receptor 3. Nature 413, 732-738.
9. Knickle, L. C., Spencer, D. F., and Renton, K. W. (1992) The suppression of hepatic cytochrome P4504A mRNA mediated by the interferon inducer polyinosinic acid polycytidylic acid. Biochem. Pharmacol. 44, 604-608.
10. Seguin, B., Teranishi, M., and Uetrecht, J. P. (2003) Modulation of D-penicillamine-induced autoimmunity in the Brown Norway rat using pharmacological agents that interfere with arachidonic acid metabolism or synthesis of inducible nitric oxide synthase. Toxicology 190, 267-278.
11. Heinzel, F. P., Sadick, M. D., Mutha, S. S., and Locksley, R. M. (1991) Production of interferon gamma, interleukin 2, interleukin 4, and interleukin 10 by CD4+ lymphocytes in vivo during healing and progressive murine leishmaniasis. Proc. Natl. Acad. Sci. U.S.A. 88, 7011-7015.
12. Laemmli, U. K., Beguin, F., and Gujer-Kellenberger, G. (1970) A factor preventing the major head protein of bacteriophage T4 from random aggregation. J. Mol. Biol. 47, 69-85.
13. Dess, D. B. M. J. C. (1983) Readily accessible 12-I-5 oxidant for the conversion of primary and secondary alcohols to aldehydes and ketones. J Org. Chem. 48, 4155-4156.
14. Albers, R., van der Pijl, A., Seinen, W., Pieters, R., and Bloksma, N. (1996) The autoimmunogenic chemicals HgCl2 and diphenylhydantoin stimulate IgG production to TNP-Ficoll and TNP-OVA, supporting and extending the graft-versus-host hypothesis for chemical induction of autoimmunity. Immunology 89, 468-473.
15. Schielen, P., van Rodijnen, W., Tekstra, J., Albers, R., and Seinen, W. (1995) Quantification of natural antibody producing B cells in rats by an improved ELISPOT technique using the poly(vinylidene difluoride) membrane as the solid support. J. Immunol. Methods 188, 33-41.
16. Nierkens, S., van Helden, P., Bol, M., Bleumink, R., van Kooten, P., Ramdien-Murli, S., Boon, L., and Pieters, R. (2002) Selective requirement for CD40-CD154 in drug-induced type 1 versus type 2 responses to trinitrophenyl-ovalbumin. J. Immunol. 168, 3747-3754.
17. Roller, S. G., Dieckhaus, C. M., Santos, W. L., Sofia, R. D., and Macdonald, T. L. (2002) Interaction between human serum albumin and the felbamate metabolites 4-Hydroxy-5-phenyl-[1,3]oxazinan-2-one and 2-phenylpropenal. Chem. Res. Toxicol. 15, 815-824.
18. Burcham, P. C., Fontaine, F. R., Petersen, D. R., and Pyke, S. M. (2003) Reactivity with Tris(hydroxymethyl)aminomethane confounds immunodetection of acrolein-adducted proteins. Chem. Res. Toxicol. 16, 1196-1201.
19. Pieters, R. (2000) The popliteal lymph node assay in predictive testing for autoimmunity. Toxicol. Lett. 112-113, 453-459.
20. Dieckhaus, C. M., Roller, S. G., Santos, W. L., Sofia, R. D., and Macdonald, T. L. (2001) Role of glutathione S-transferases A1-1, M1-1, and P1-1 in the detoxification of 2-phenylpropenal, a reactive felbamate metabolite. Chem. Res. Toxicol. 14, 511-516.
21. Katsutani, N., and Shionoya, H. (1992) Popliteal lymph node enlargement induced by procainamide. Int. J. Immunopharmacol. 14, 681-686.
22. Thompson, C. D., Gulden, P. H., and Macdonald, T. L. (1997) Identification of modified atropaldehyde mercapturic acids in rat and human urine after felbamate administration. Chem. Res. Toxicol. 10, 457-462.