Oxazolidonylethyl adducts to hemoglobin and DNA following nornitrogen mustard exposure

Chemico-Biological Interactions

Volumn 99, Issue 1-3, 1996, Pages 263-275

  Thulin, H ^a   Zorcec, V ^b   Segerback D ^c   Sundwall, A ^a   Tornqvist M ^b  

^a PFIZER INC   (United States)

^b STOCKHOLM UNIVERSITY   (Sweden)

^c KAROLINSKA INSTITUTE   (Sweden)

Author keywords

7 (Oxazolidonylethyl)guanine; Cyclophosphamide; DNA adducts; Hemoglobin adducts; N (oxazolidonylethyl)valine; Nornitrogen mustard

Indexed keywords

CYCLOPHOSPHAMIDE; DICHLORODIETHYLAMINE; DRUG METABOLITE; GUANINE DERIVATIVE; HEMOGLOBIN; OXAZOLIDINONE DERIVATIVE; UNCLASSIFIED DRUG; VALINE DERIVATIVE;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; BIOLOGICAL MONITORING; CONTROLLED STUDY; DNA ADDUCT; FEMALE; INTRAVENOUS DRUG ADMINISTRATION; MOUSE; NONHUMAN; PROTEIN BINDING;

EID: 0030025555     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/0009-2797(95)03674-1     Document Type: Article

References (20)

1. A.D. Tates, T. Grummt. M. Törnqvist, P.B. Farmer, F.J. van Dam, H. van Mossel, H.M. Schoemaker, S. Osterman-Golkar, Ch. Uebel, Y.S. Tang, A.H. Zwinderman, A.T. Natarajan and L. Ehrenberg, Biological and chemical monitoring of occupational exposure to ethylene oxide, Mutat. Res., 250 (1991) 483-497.
2. M. Törnqvist, Current research on hemoglobin adducts and cancer risks, an overview, in: C.C. Travis (Ed.), Use of Biomarkers in Assessing Health and Environmental Impacts of Chemical Pollutants, NATO ARW, Luso, Portugal, Plenum, New York, 1993, pp. 17-30.
3. E. Bailey, P.B. Farmer, Y-S. Tang, H. Vangikar, A. Gray, D. Slee, R.M.J. Ings, D.B. Campbell, J.G. McVie and R. Dubbelman, Hydroxyethylation of hemoglobin by 1-(2-chloroethyl)-1-nitrosoureas, Chem. Res. Toxicol. (1991) 462-466.
4. I. Jardine, C. Fenselau, M. Appler, M.-N. Kan, R.B. Brundrett and M. Colvin, Quantification by gas chromatography-chemical ionization mass spectrometry of cyclophosphamide mustard and nornitrogen mustard in the plasma and urine of patients receiving cyclophosphamide therapy, Cancer Res., 38 (1978) 408-415.
5. P.J. Cox and L. Levin, Novel metabolic products of cyclophosphamide in human urine, Biochem. Pharmacol., 24 (1975) 1233-1235.
6. J. Doskocil and Z. Sormová, The reaction of DNA with mustards I. The reaction products, Collect. Czech. Chem. Commun., 30 (1965) 481-491.
7. K. Hemminki, DNA-binding products of nornitrogen mustard, a metabolite of cyclophosphamide, Chem.-Biol. Interact., 61 (1987) 126-130.
8. K. Hemminki, Nitrogen mustards and ethylene imines, in: K. Hemminki, A. Dipple, D.E.G. Shuker, F.F. Kadlubar, D. Segerbäck and H. Bartsch (Eds.), DNA Adducts: Identification and Biological Significance, IARC Scientific Publication No. 125, International Agency for Research on Cancer, Lyon, 1994, pp. 313-321.
9. J. Benson, C.N. Martin and R.C. Garner, N-(2-Hydroxyethyl)-N-[2-(7-guaninyl)ethyl]amine, the putative major DNA adduct of cyclophosphamide in vitro and in vivo in the rat, Biochem. Pharmacol., 37 (1988) 2979-2985.
10. H. Arnold and H. Bekel, Die Oxazolidon-Reaktion von 2-chloräthyl-substituierten sekundären Ammen, Arzneim.-Forsch., 14 (1964) 750-752.
11. C.B. Robinson and H.F. Herbrandson, Kinetics and mechanism of the reaction of 2,2′-dichlorodiethylamine with aqueous carbon dioxide, J. Am. Chem. Soc. (1972) 7883-7887.
12. E. Balbinder, C.I. Reich, D. Shugarts, J. Koegh, R. Fibiger, T. Jones and A. Banks, Relative mutagenicity of some urinary metabolites of the antitumor drug cyclophosphamide, Cancer Res., 41 (1981) 2967-2972.
13. C.E. Williamson, J.G. Kirby, J.I. Miller, S. Sass, S.P. Kramer, A.M. Seligman and B. Witten, The enzymatic transformation of some nitrogen mustards in the presence of carbon dioxide: implications in respiration, Cancer Res., 26 (1966) 323-330.
14. P.S. Hong, A. Srigritsanapol and K.K. Chan, Pharmacokinetics of 4-hydroxycyclophosphamide and metabolites in the rat, Drug Metab. Dispos., 19 (1991) 1-7.
15. J. Mowrer, M. Törnqvist, S. Jensen, and L. Ehrenberg, Modified Edman degradation applied to hemoglobin for monitoring occupational exposure to alkylating agents, Toxicol. Environ. Chem., 11 (1986) 215-231.
16. M. Törnqvist, Epoxide adducts to N-terminal valine of hemoglobin, Methods Enzymol., 231B (1994) 650-657.
17. M. Törnqvist, J. Mowrer, S. Jensen and L. Ehrenberg, Monitoring of environmental cancer initiators through hemoglobin adducts by a modified Edman degradation method, Anal. Biochem., 154 (1986) 255-266.
18. F. Granath, L. Ehrenberg and M. Törnqvist, Degree of alkylation of macromolecules in vivo from variable exposure, Mutat. Res., 284 (1992) 297-306.
19. N.I. Berlin, Life span of the red cell, in: C. Bishop and D.M. Surgenor (Eds.), The Red Blood Cell, Academic Press, New York, 1964, pp. 423-450.
20. P. Rydberg, B. Lüning, C.A. Wachtmeister and M. Törnqvist, Synthesis and characterization of N-substituted valines and their phenyl- and pentafluorophenyl-thiohydantoins, Acta Chim. Scand., 47 (1993) 813-817.