Biotransformation of nitroso aromatic compounds and 2-oxo acids to N- hydroxy-N-arylacylamides by thiamine-dependent enzymes in rat liver

Drug Metabolism and Disposition

Volumn 26, Issue 7, 1998, Pages 705-710

  Yoshioka, Tadao ^b   Uematsu, Takayoshi ^a  

^a HOKKAIDO INSTITUTE OF TECHNOLOGY   (Japan)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

2 OXO 3 METHYLVALERIC ACID; 2 OXOACID; 2 OXOACID DEHYDROGENASE; 2 OXOBUTYRIC ACID; 2 OXOISOCAPROIC ACID; 2 OXOISOVALERIC ACID; 2 OXOVALERIC ACID; AROMATIC AMIDE; AROMATIC NITRO COMPOUND; CARCINOGEN; GLYOXYLIC ACID; N HYDROXY N PHENYLACYLAMIDE; N HYDROXY N PHENYLFORMAMIDE; N HYDROXY N PHENYLGLYCOLAMIDE; N HYDROXY N PHENYLPHENYLACETAMIDE; NITROSOBENZENE; PYRUVATE DEHYDROGENASE; PYRUVIC ACID; TRANSKETOLASE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; DRUG TRANSFORMATION; ENZYME ACTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIVER CARCINOGENESIS; LIVER CYTOSOL; LIVER MICROSOME; LIVER MITOCHONDRION; MALE; NONHUMAN; PRIORITY JOURNAL; RAT;

ANIMALS; BIOTRANSFORMATION; LIVER; MALE; MITOCHONDRIA, LIVER; NITROSO COMPOUNDS; RATS; RATS, WISTAR; THIAMINE;

EID: 0031817388     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (29)

1. Boyer B and Odessey R (1991) Kinetic characterization of branched chain ketoacid dehydrogenase. Arch Biochem Biophys 285:1-7.
2. Corbett MD, Baden DG and Chipko BR (1979) The nonmicrosomal production of N-(4-chlorophenyl)glycolhydroxamic acid from 4-chloronitrosobenzene by rat liver homogenates. Bioorg Chem 8:227-235.
3. Corbett MD and Chipko BR (1979) Quantitative determination of N-arylaceto- and N-arylglycolhydroxamic acids in biochemical reaction mixtures. Anal Biochem 98:169-177.
4. Corbett MD and Chipko BR (1980) Reaction of nitroso aromatics with glyoxylic acid: a new path to hydroxamic acids. J Org Chem 45:2834-2839.
5. Corbett MD and Corbett BR (1980) Comparative aspects of hydroxamic acid production by thiamine-dependent enzymes. Bioorg Chem 9:273-287.
6. Corbett MD and Corbett BR (1986) Effect of ring substituents on the transketolase-catalyzed conversion of nitroso aromatics to hydroxamic acids. Biochem Pharmacol 35:3613-3621.
7. Corbett MD and Corbett BR (1995) Bioorganic chemistry of the arylhydroxylamine and nitrosoarene functional groups, in Biodegradation of Nitroaromatic Compounds (Spain J ed) pp 151-182, Plenum Press, New York.
8. Corbett MD, Corbett BR and Doerge DR (1982) Hydroxamic acid production and active-site induced Bamberger rearrangement from the action of α-ketoglutarate dehydrogenase on 4-chloronitrosobenzene. J Chem Soc Perkin Trans I 345-350.
9. Goldstein JA and Faletto MB (1993) Advances in mechanisms of activation and deactivation of environmental chemicals. Environ Health Perspect 100:169-176.
10. Hammett LP (1970) Quantitative relationships involving structure and reactivity, in Physical Organic Chemistry (Hammett LP ed) pp 347-390, McGraw-Hill, New York.
11. Hanna PE (1994) N-Acetyltransferases, O-acetyltransferases, and acetyltransferases: enzymology and bioactivation. Adv Pharmacol 27:401-430.
12. Harris RA, Paxton R, Goodwin GW, Kuntz MJ, Shimomura Y and Han A (1986) Regulation of branched-chain amino acid metabolism. Biochem Soc Trans 14:1005-1008.
13. Khailova LS, Korochkina LG and Severin SE (1989) Organization and functioning of muscle pyruvate dehydrogenase active center. Ann NY Acad Sci 573:36-54.
14. Kochetov GA (1982) Transketolase from yeast, rat liver, and pig liver. Methods Enzymol 90:209-223.
15. Koike K, Hamada M, Tanaka N, Otsuka K, Ogasawara K and Koike M (1974) Properties and subunit composition of the pig heart 2-oxoglutarate dehydrogenase. J Biol Chem 249:3836-3842.
16. Markwell MAK, Hass SM, Tolbert NE and Bieber LL (1981) Protein determination in membrane and lipoprotein samples: manual and automated procedures. Methods Enzymol 72:296-303.
17. Michejda CJ and Kroeger-Koepke MB (1994) Carcinogen activation by sulfate conjugate formation. Adv Pharmacol 27:331-363.
18. Paxton R and Harris RA (1982) Isolation of rabbit liver branched chain α-ketoacid dehydrogenase and regulation by phosphorylation. J Biol Chem 257:14433-14439.
19. Paxton R, Scislowski PWD, Davis EJ and Harris RA (1986) Role of branched-chain 2-oxo acid dehydrogenase and pyruvate dehydrogenase in 2-oxobutyrate metabolism. Biochem J 234: 295-303.
20. Sakamoto Y, Yoshioka T and Uematsu T (1989) N-Arylhydroxamic acids: reaction of nitroso aromatics with α-oxo acids. J Org Chem 54:4449-4453.
21. Sakoda M and Hiromi K (1976) Determination of the best-fit values of kinetic parameters of the Michaelis-Menten equation by the method of least squares with Taylor expansion. J Biochem (Tokyo) 80:547-555.
22. Shimomura Y, Paxton R, Ozawa T and Harris RA (1987) Purification of branched chain α-keto acid dehydrogenase complex from rat liver. Anal Biochem 163:74-78.
23. Shorter J (1972) The separation of polar, steric, and resonance effects by the use of linear free energy relationships, in Advances in Linear Free Energy Relationships (Chapman NB and Shorter J ed) pp 71-117. Plenum Press, New York.
24. Wagenmakers AJM, Schepens JTG, Veldhuizen JAM and Veerkamp JH (1984) The activity state of the branched-chain 2-oxo acid dehydrogenase complex in rat tissues. Biochem J 220:273-281.
25. Yeaman SJ (1989) The 2-oxo acid dehydrogenase complexes: recent advances. Biochem J 257:625-632.
26. Yeaman SJ, Cook KG, Bradford AP and Lawson R (1988) Regulation of branched-chain 2-oxo acid dehydrogenase complexes by reversible phosphorylation, in Thiamine Pyrophosphate Biochemistry (Schellenberger A and Schowen RL ed) vol 2, pp 77-82, CRC Press, Boca Raton, FL.
27. Yoshioka T, Ohno H and Uematsu T (1996) Pyruvate dehydrogenase complex-catalyzed formation of N-arylacetohydroxamic acids from nitroso aromatic compounds in rat isolated cells and perfused organs. J Pharmacol Exp Ther 279:1282-1289.
28. Yoshioka T, Suzuki T and Uematsu T (1989) Biotransformation of N-substituted aromatic compounds in mammalian spermatozoa. J Biol Chem 264:12432-12438.
29. Yoshioka T and Uematsu T (1993) Formation of N-hydroxy-N-arylacetamides from nitroso aromatic compounds by the mammalian pyruvate dehydrogenase complex. Biochem J 290: 783-790.