N-acetylation of the heterocyclic amine batracylin by human liver

Drug Metabolism and Disposition

Volumn 27, Issue 9, 1999, Pages 966-971

  Stevens, Gregory J ^a   Payton, Mark ^b   Sim, Edith ^b   Mcqueen, Charlene A ^a  

^a UNIVERSITY OF ARIZONA   (United States)

^b UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINOBENZOIC ACID; ACETYLATING AGENT; AMINE; BATRACYLIN; CISPLATIN; DOXORUBICIN; SULFADIMIDINE; UNCLASSIFIED DRUG;

ACETYLATION; ANTINEOPLASTIC ACTIVITY; ARTICLE; DOSE RESPONSE; ENZYME ACTIVITY; GENETIC POLYMORPHISM; GENOTYPE; HUMAN; HUMAN TISSUE; MUTAGENICITY; PHENOTYPE; PRIORITY JOURNAL;

4-AMINOBENZOIC ACID; ACETYLATION; ADULT; AGED; ANTINEOPLASTIC AGENTS; ARYLAMINE N-ACETYLTRANSFERASE; CHILD, PRESCHOOL; CLONING, MOLECULAR; CYTOSOL; DNA PRIMERS; FEMALE; GENOTYPE; HUMANS; KINETICS; LIVER; MALE; MIDDLE AGED; QUINAZOLINES; SULFAMETHAZINE;

ANIMALIA;

EID: 0032845415     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (45)

1. Ames MM, Mathiesen DA and Reid JM (1991) Differences in N-acetylation of the experimental antitumor agent batracylin in the mouse and the rat. Invest New Drugs 9:219-225.
2. Bell DA, Badawi AF, Lang NF, Ilett KF, Kadlubar FF and Hirvonen AA (1995b) Polymorphism in the N-acetyltransferase 1 (NAT1) polyadenylation signal:-Association of NAT1*10 allele with higher N-acetylation activity in bladder and colon tissue. Cancer Res 55:5226-5229.
3. Bell DA, Stephens EA, Castranio T, Umbach DM, Watson M, Deakin M, Elder J, Hendrickse C, Duncan H and Strange RC (1995a) Polyadenylation polymorphism in the acetyltransferase 1 gene (NAT 1) increases risk of colorectal cancer. Cancer Res 55:3537-3542.
4. Blum M, Demierre A, Grant DM, Heim M and Meyer UA (1991) Molecular mechanism of slow acetylation of drugs and carcinogens in humans. Proc Natl Acad Sci USA 88:5237-5341.
5. Butcher NJ, Ilett KF and Minchin RF (1998) Functional polymorphism of the human arylamine N-acetyltransferase type 1 gene caused by (CT)-T-190 and G(560)A mutations. Pharmacogenetics 8:67-72.
6. Davis CD, Schut HA, Adamson RH, Thorgeirsson UP, Thorgeirsson SS and Snyderwine EG (1993) Mutagenic activation of IQ, PhIP and MeIQx by hepatic microsomes from rat, monkey and man: Low mutagenic activation of MeIQx in cynomologous monkeys in vitro reflects low DNA adduct levels in vivo. Carcinogenesis 14:61-65.
7. Deguchi T (1992) Sequences and expression of alleles of polymorphic arylamine N-acetyltransferase of human liver. J Biol Chem 267:18140-18147.
8. Deitz AC, Doll MA and Hein DW (1997) A restriction fragment length polymorphism assay that differentiates human N-acetyltransferase-1 (NAT1) alleles. Anal Biochem 253:219-224.
9. Derewlany LO, Knie B and Koren B (1994) Arylamine N-acetyllransferase activity of the human placenta. J Pharmacol Exp Ther 269:756-760.
10. DiLella AG and Woo SL (1987) Cloning of large segments of DNA using cosmid vectors. Methods Enzymol 152:199-212.
11. Doll MA, Jiang W, Deitz AC, Rustan TD and Hein DW (1997) Identification of a novel allele at the human NATI acetyltransferase locus. Biochem Biophys Res Commun 133:584-591.
12. El-Hawari M, Stoltz ML and Pallas F (1989) Species differences in the toxic responses to batracylin (NSC-320846) (Abstract). Proc Am Assoc Cancer Res 30:626.
13. Estrada-Rodgers L, Levy GN and Weber WW (1998) Substrate selectivity of mouse N-acetyltransferases 1, 2 and 3 expressed in COS-1 cells. Drug Melab Dispos 26:502-505.
14. Glowinski IB and Weber WW (1982) Biochemical characterization of genetically variant aromatic amine N-acetyltransferase in A/J and C57BL/6J mice. J Biol Chem 257:1431-1437.
15. Glowinski IB, Weber WW, Fysh JM, Vaught JB and King CM (1980) Evidence that arylhydroxamic acid N,O acetyltransferase and the genetic polymorphic N-acetyltransferase are properties of the same enzyme in rabbit liver. J Biol Chem 255:7883-7890.
16. Grant DM, Blum M, Beer M and Meyer UA (1991) Monomorphic and polymorphic human arylamine N-acetyltransferases: A comparison of liver isozymes and expressed products of two cloned genes. Mol Pharmacol 39:184-191.
17. Grant DM, Hughes NC, Janezic SA, Goodfellow GH, Chen HJ, Gaedigk A, Yu VL and Grewal R (1997) Human acetyltransferase polymorphisms. Mutat Res 376:61-70.
18. Hein DW, Omichinski JB, Brewer JA and Weber WW (1982a) A unique pharmacogenetic expression of the N-acetylation polymorphism in the inbred hamster. J Pharmacol Exp Ther 220:8-15.
19. Hein DW, Rustan TD, Ferguson JR, Doll MA and Gray K (1994) Metabolic activation of aromatic and heterocyclic N-hydroxylamines by wild type and mutant recombinant human NAT 1 and NAT 2 acetyltransferases. Arch Toxicol 68:129-133.
20. Hein DW, Smolen TN, Fox RR and Weber WW (1982b) Identification of genetically homozygous rapid and slow acetylators of drugs and environmental carcinogens among established inbred rabbit strains. J Pharmacol Exp Ther 223:40-44.
21. Hickman D, Pope J, Paul SD, Fakis ET, Smelt V, Stanley LA, Payton M, Unadkat JD and Sim E (1998) Expression of arylamine N-acetyltransferase in human intestine. GUT 42:402-409.
22. Hughes NC, Janezic SA, McQueen KL, Jewett MAS, Castranio T, Bell DA and Grant DM (1998) Identification and characterization of variant alleles of human acetyltransferase NAT1 with defective function using p-aminosalicylate as an in vivo and in vitro probe. Pharmacogenetics 8:55-66.
23. Juberg DR, Bond JT and Weber WW (1991) N-acetylation of aromatic amines: Genetic polymorphism in inbred rat strains. Pharmacogenetics 1:50-57.
24. Kato R (1986) Metabolic activation of mutagenic heterocyclic aromatic amines from protein pyrolysates. CRC Crit Rev Tox 16:307-348.
25. Kato R and Yamazoe Y (1994) Metabolic activation of N-hydroxylated metabolites of carcinogenic and mutagenic arylamines and arylamides by esterification. Drug Metab Rev 26:413-430.
26. Kilbane AJ, Petroff T and Weber WW (1991) Kinetics of acetyl CoA: Arylamine N-acetyltransferase from rapid and slow acetylator human liver. Drug Metab Dispos 19:503-507.
27. Lower GM and Bryan GT (1973) Enzymatic N-acetylation of carcinogenic aromatic amines by liver cytosol of species displaying different organ susceptibilities. Biochem Pharmacol 22: 1581-1588.
28. Malfatti MA, Buonarati MH, Turteltaub KW, Shen NH and Felton JS (1994) The role of sulfation and/or acetylation in the metabolism of the cooked-food mutagen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in Salmonella typhimurium and isolated rat hepatocytes. Chem Res Toxicol 7:139-147.
29. Maltano SS, Land S, King CM and Weber WW (1989) Purification and biochemical characterization of hepatic arylamine N-acetyltransferase from rapid and slow acetytator mice: Identity with arylhydroxamic acid N,O-acelyltransferase and N-hydroxylamine O-acetyltransferase. Mol Pharmacol 35:599-609.
30. Mattano SS and Weber WW (1987) Kinetics of arylamine N-acetyltransferase in tissues from rapid and slow acetylator mice. Carcinogenesis 8:133-137.
31. Meegalla, SK, Stevens GJ, McQueen CA, Chen AY, Yu C, Liu LF, Burrows LR and LaVoie EJ (1994) Synthesis and pharmacological evaluation of isoindolo[1,2-b]quinazolinone and isoindolo[2,1-a]benimidazole derivatives related to the antitumor agent batracylin. Med Chem 37:3434-3439.
32. Payton MA and Sim E (1998) Genotyping human arylamine N-acetyltransferase type 1 (NAT 1). Biochem Pharmacol 55:361-366.
33. Plowman J, Paul KD, Atassi B, Harrison SD, Dykes DJ, Dabbe HJ, Narayanan VL and Yoder OC (1988) Preclinical antitumor activity of batracylin (NSC 320846). Invest New Drugs 6:147-153.
34. Risch A, Smelt V, Lane D, Stanley L, van der Slot W, Ward A and Sim E (1996) Arylamine N-acetyltransferase in erythrocytes of cystic fibrosis patients. Pharmacol Toxicol 78:235-240.
35. Risch A, Wallace DMA, Bathers S and Sim E (1995) Slow N-acetylation genotype is a susceptibility factor in occupational and smoking related bladder cancer. Hum Mol Genet 4:231-236.
36. Shinohara A, Saito K, Yamazoe Y, Kamataki T and Kato R (1986) Acetyl coenzyme A dependent activation of N-hydroxy derivatives of carcinogenic arylamines: Mechanism of activation, species difference, tissue distribution, and acetyl donor specificity. Cancer Res 44:4362-4367.
37. Smelt VA, Mardon HJ and Sim E (1998) Placental expression of arylamine N-acetyltransferases: Evidence for linkage disequilibrium between NAT1*10and NAT2*4 alleles of the two human arylamine N-acetyltransferase loci NAT1 and NAT2. Pharmacol Toxicol 83:149-157.
38. Stanley LA, Mills IG and Sim E (1997) Localization of polymorphic N-acetyltransferase (NAT2) in tissues of inbred mice. Pharmacogenetics 7:121-130.
39. Stevens GJ, Bardsley B and McQueen CA (1996a) N-acetylation of the heterocyclic amine batracylin by mouse, rat and human liver. Fundam Appl Toxicol 30:1, part 2, 217.
40. Stevens GJ, LaVoie EJ and McQueen CA (1996b) The role of acetylation in the mutagenicity of the antitumor agent, batracylin. Carcinogenesis 17:115-119.
41. Stevens GJ and McQueen CA (1994) Species variation in the genotoxicity of batracylin. Toxicol Appl Pharmacol 126:39-44.
42. Vatsis KP, Martell KJ and Weber WW (1991) Diverse point mutations in the human gene for polymorphic N-acetyltransferase. Proc Natl Acad Sci USA 88:6333-6337.
43. Vatsis KP and Weber WW (1993) Structural heterogeneity of Caucasian N-acetyltransferase at the NAT1 gene locus. Arch Biochem Biophys 301:71-76.
44. Vatsis KP, Weber WW, Bell DA, Dupret JM, Evans DAP, Grant DM, Hein DW, Lin HJ, Meyer UA, Relling MV, Sim E, Suzuki T and Yamazoe Y (1995) Nomenclature for N-acetyltransferase. Pharmacogenetics 5:1-17.
45. Waud WR, Harrison SD, Gilbert KL, Laster WR and Griswold DP (1991) Antitumor drug cross-resistance in vivo in a cisplatin-resistant murine P388 leukemia. Cancer Chemother Pharmacol 27:456-463.