N-Methylcarbamoyl-lysine adduct in globin: A new metabolic product and potential biomarker of N,N-dimethylformamide in humans

Toxicology Letters

Volumn 162, Issue 2-3 SPEC. ISS., 2006, Pages 211-218

  Mraz J ^a   Cimlova J ^b   Stransky V ^a   Nohova H ^a   Kicova R ^a   Siimek P ^b  

^a NATIONAL INSTITUTE OF PUBLIC HEALTH   (Czech Republic)

^b INSTITUTE OF ENTOMOLOGY   (Czech Republic)

Author keywords

Adducts; Globin; Lysine; N,N Dimethylformamide; N terminal valine

Indexed keywords

3 METHYL 5 ISOPROYLHYDANTOIN; BIOLOGICAL MARKER; GLOBIN; HYDANTOIN DERIVATIVE; LYSINE DERIVATIVE; METHYL ISOCYANATE; N EPSILON (N METHYLCARBAMOYL)LYSINE; N METHYLCARBAMOYLLYSINE; N METHYLCARBAMOYLVALINE; N METHYLFORMAMIDE; N,N DIMETHYLFORMAMIDE; PRONASE; UNCLASSIFIED DRUG; VALINE;

ARTICLE; CONTROLLED STUDY; ENZYME ACTIVITY; ENZYME RELEASE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HYDROLYSIS; LONG TERM EXPOSURE; MASS SPECTROMETRY; OCCUPATIONAL EXPOSURE; PRIORITY JOURNAL; PROTEIN BLOOD LEVEL;

BIOLOGICAL MARKERS; DIMETHYLFORMAMIDE; GLOBINS; HUMANS; HYDANTOINS; LYSINE; OCCUPATIONAL EXPOSURE; PROTEIN BINDING;

EID: 32644442639     PISSN: 03784274     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.toxlet.2005.09.039     Document Type: Article

References (20)

1. J. Angerer, T. Göen, A. Krämer, and H.U. Käfferlein N-methylcarbamoyl adducts at the N-terminal valine of globin in workers exposed to N,N-dimethylformamide Arch. Toxicol. 72 1998 309 313
2. T.R. Fennell, S.C.J. Sumner, and V.E. Walker A model for the formation and removal of the hemoglobin adducts Cancer Epidemiol. Biomarkers Prev. 1 1992 213 219
3. H.U. Käfferlein, and J. Angerer N-Methylcarbamoylated valine of hemoglobin in humans after exposure to N,N-dimethylformamide: evidence for the formation of methyl isocyanate? Chem. Res. Toxicol. 14 2001 833 840
4. P. Kestell, M.H. Gill, M.D. Threadgill, A. Gescher, O.W. Howarth, and E.H. Curzon Identification by proton NMR of N-(hydroxymethyl)-N-methylformamide as the major urinary metabolite of N,N-dimethylformamide in mice Life Sci. 38 1986 719 724
5. P. Kestell, A.P. Gledhill, M.D. Threadgill, and A. Gescher S-(N-Methylcarbamoyl)-N-acetylcysteine: a urinary metabolite of the hepatotoxic experimental antitumour agent N-methylformamaide (NSC 3051) in mouse, rat and man Biochem. Pharmacol. 35 1986 2283 2286
6. P. Kestell, M.D. Threadgill, A. Gescher, A.P. Gledhill, A.J. Shaw, and P.B. Farmer An investigation on the relationship between the hepatotoxicity and the metabolism of N-alkylformamides J. Pharmacol. Exp. Ther. 240 1986 265 270
7. J. Mráz, E. Gálová, H. Nohová, Š. Boušková, and M. Hornychová Formation of N-methylcarbamoyl adduct with N-terminal valine of globin following the exposure to N,N-dimethylformamide (DMF) and N-methylformamide (MF) in rats (Abstract) 4th International Symposium on Biological Monitoring in Occupational and Environmental Health Seoul, Korea, September 23-25, 1998 1998 125 126 Book of abstracts
8. J. Mráz, E. Gálová, H. Nohová, and Š. Boušková N-Methylcarbamoyl adduct with N-terminal valine of globin: a new biomarker of exposure to N,N-dimethylformamide (DMF) in humans (Abstract) 4th International Symposium on Biological Monitoring in Occupational and Environmental Health Seoul, Korea, September 23-25, 1998 1998 145 146 Book of abstracts
9. J. Mráz, Š. Dušková, E. Gálová, H. Nohová, and M. Brabec Biological monitoring of N,N-dimethylformamide. Reference value for N-methylcarbamoyl adduct at the N-terminal valine of globin as biomarker of chronic occupational exposure Int. Arch. Occup. Environ. Health 75 Suppl. 2002 S93 S96
10. J. Mráz, Š. Dušková, E. Gálová, H. Nohová, P. Krausová, I. Linhart, and P. Šimek Improved gas chromatographic-mass spectrometric determination of the N-methylcarbamoyl adduct at the N-terminal valine of globin, a metabolic product of the solvent N,N-dimethylformamide J. Chromatogr. B 778 2002 357 365
11. J. Mráz, and H. Nohová Absorption, metabolism and elimination of N,N-dimethylformamide in humans Int. Arch. Occup. Environ. Health 64 1992 85 92
12. J. Mráz, P. Šimek, D. Chvalová, H. Nohová, and P. Šmigolová Studies on the methyl isocyanate adducts in globin Chem. Biol. Interact. 148 2004 1 10
13. J. Mráz, and F. Tureček Identification of N-acetyl-S-(N-methylcarbamoyl)cysteine, a human metabolite of N,N-dimethylformamide and N-methylformamide J. Chromatogr. Biomed. Appl. 414 1987 399 404
14. P.G. Pearson, J.G. Slatter, M.S. Rashed, D.-H. Han, and T.A. Baillie Carbamoylation of peptides and proteins in vitro by S-(N-methylcarbamoyl) glutathione and S-(N-methylcarbamoyl)cysteine, two electrophilic S-linked conjugates of methyl isocyanate Chem. Res. Toxicol. 4 1991 436 444
15. P.K. Ramachandran, B.R. Gandhe, K.S. Venkateswaran, M.P. Kaushik, R. Vijayaraghavan, G.S. Agarwal, N. Gopalan, M.V.S. Suryanarayana, and S.K. Shinde Gas chromatographic studies of the carbamylation of hemoglobin by methylisocyanate in rats and rabbits J. Chromatogr. Biomed. Appl. 426 1988 239 247
16. V. Scailteur, and R. Lauwerys In vivo metabolism of dimethylformamide and relationship to toxicity in the male rat Arch. Toxicol. 56 1984 87 91
17. A.J. Shaw, A. Gescher, and J. Mráz Cytotoxicity and metabolism of the hepatotoxin N-methylformamide and related formamides in mouse hepatocytes Toxicol. Appl. Pharmacol. 95 1988 162 170
18. K.H. Slotta, and L. Lorenz Uber Isocyanate. I. Darstellung aliphatischer isocyanate Chem. Ber. 58 1925 1320 1325
19. M.D. Threadgill, D.B. Axworthy, T.A. Baillie, P.B. Farmer, K.C. Farrow, A. Gescher, P. Kestell, P.B. Pearson, and A.J. Shaw Metabolism of N-methylformamide in mice: primary kinetic deuterium isotope effect and identification of S-(N-methylcarbamoyl)glutathione as a metabolite J. Pharmacol. Exp. Ther. 242 1987 312 319
20. M. Tornqvist, C. Fred, J. Haglund, H. Helleberg, B. Paulsson, and P. Rydberg Protein adducts: quantitative and qualitative aspects of their formation, analysis and applications J. Chromatogr. B 778 2002 279 308