Structure-activity relationships in the deacetylation of O-glucosides of N-hydroxy-N-arylacylamides by mammalian liver microsomes

Chemico-Biological Interactions

Volumn 137, Issue 1, 2001, Pages 25-42

  Yoshioka, Tadao ^a   Tatsunami, Ryosuke ^a   Ohno, Hiroaki ^a   Uematsu, Takayoshi ^a  

^a HOKKAIDO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Carboxylesterase; Deacetylation species difference; HOMO; LUMO; O glucosides of N hydroxy N arylacylamides

Indexed keywords

ACETANILIDE DERIVATIVE; AMIDE; GLUCOSIDE; N ACETYL 2 CHLOROANILINO BETA DEXTRO GLUCOPYRANOSIDE; N ACETYL 2 METHYLANILINO BETA DEXTRO GLUCOPYRANOSIDE; N ACETYL 3 CHLOROANILINO BETA DEXTRO GLUCOPYRANOSIDE; N ACETYL 3 METHYLANILINO BETA DEXTRO GLUCOPYRANOSIDE; N ACETYL 4 CHLOROANILINO BETA DEXTRO GLUCOPYRANOSIDE; N ACETYL 4 METHYLANILINO BETA DEXTRO GLUCOPYRANOSIDE; N BUTYRYLANILINO BETA DEXTRO GLUCOPYRANOSIDE; N HYDROXYACETANILIDE; N HYDROXYACYLAMIDE DERIVATIVE; N PROPIONYLANILINO BETA DEXTRO GLUCOPYRANOSIDE; O GLUCOSIDE DERIVATIVE; PYRANOSIDE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CATALYSIS; CATTLE; CELL ACTIVITY; CELLULAR DISTRIBUTION; CONTROLLED STUDY; DEACETYLATION; DRUG INHIBITION; HAMSTER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIPOPHILICITY; LIVER MICROSOME; MALE; METABOLIC ACTIVATION; NONHUMAN; RABBIT; RAT; SPECIES DIFFERENTIATION; STRUCTURE ACTIVITY RELATION; TECHNIQUE;

ANILINE COMPOUNDS; ANIMALS; CELL FRACTIONATION; GLUCOSIDES; HUMANS; KINETICS; MALE; MICROSOMES, LIVER; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY; SWINE;

BOVINAE; CRICETINAE; MAMMALIA; ORYCTOLAGUS CUNICULUS; SUIDAE;

EID: 0035979305     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0009-2797(01)00167-3     Document Type: Article

References (36)

1. Microsomal amidases and carboxylesterases
2. The mammalian carboxylesterases: From molecules to functions
3. Cytochrome P-450 catalysed activation of carcinogenic aromatic amines and amides
4. Rat liver cytochrome P450 metabolism of N-acetylbenzidine and N,N′-diacetylbenzidine
5. Biotransformation of N-substituted aromatic compounds in mammalian spermatozoa
6. Formation of N-hydroxy-N-arylacetamides from nitroso aromatic compounds by the mammalian pyruvate dehydrogenase complex
7. Reductive metabolism of 4-nitrobiphenyl by rat liver fraction
8. Roles of glucuronidation and UDP-glucuronosyltransferases in xenobiotic bioactivation reaction
9. Activation of the O-glucuronide of the carcinogen N-hydroxy-N-2-fluorenylacetamide by enzymatic deacetylation in vivo: Formation of fluorenylamine-tRNA adducts
10. Advances in mechanisms of activation and deactivation of environmental chemicals
11. N-acetyltransferases, O-acetyltransferases, and acetyltransferases
12. Carcinogen activation by sulfate conjugate formation
13. Influence of the aryl group on the reaction of N-arylacethydroxamic acids with polynucleotides
14. Glycosides of N-hydroxy-N-arylamine derivatives. Part 1. Synthesis and mutagenicity of O-glucosides of N-hydroxy-N-arylamines and their acetohydroxamic acids
15. Mutagenicity of N-arylacetohydroxamic acids and their O-glucosides derived from chlorinated 4-nitrobiphenyl ethers
16. AM1: A new general purpose quantum mechanical molecular model
17. Polarimetry
18. High-resolution nuclear magnetic resonance spectroscopy
19. Preparation of microsomes with calcium
20. Protein determination in membrane and lipoprotein samples: Manual and automated procedures
21. Determination of the best-fit values of kinetic parameters of the Michaelis-Menten equation by the method least squares with Taylor expansion
22. Characterization of molecular species of liver microsomal carboxylesterases of several animal species and humans
23. Molecular aspects of carboxylesterase isoforms in comparison with other esterases
24. Conformational preferences and energetics of N-O heterolyses in aryl nitrenium ion precursors: Ab initio and semiempirical molecular orbital calculations
25. Purification and characterization of guinea-pig liver microsomal deacetylase involved in the deacetylation of the O-glucoside of N-hydroxyacetanilide
26. Relationship between nucleic acid adduct formation and deacylation of arylhydroxamic acids
27. Purification and characterization of a porcine liver microsomal triacylglyderol hydrolase
28. Purification and characterization of retinyl ester hydrolase as a member of the non-specific carboxylesterase supergene family
29. Species differences in the induction of hepatic microsomal carboxylesterases caused by dietry exposure to di(2-ethylhexyl)phthalate, a peroxisome proliferator
30. Isolation, properties, and the complete amino acid sequence of a second form of 60-kDa glycoprotein esterase
31. Isolation and complete covalent structure of liver microsomal paraoxonase
32. Regulation of two rat liver microsomal carboxylesterase isozyme: Species differences, tissue distribution, and the effects of age, sex, and xenobiotic treatment of rats
33. Purification and characterization of a neutral, bile salt-independent retinyl ester hydrolase from rat liver microsomes
34. Purification and properties of a cholesteryl ester hydrolase from rat liver microsomes
35. On the mechanism of action at the acylation step of the α-chymotrypsin-catalyzed hydrolysis of anilides
36. Mechanism of in vitro mutagenic activation and covalent binding of N-hydroxy-2-acetylaminofluorene in isolated liver cell nuclei from rat and mouse