Characterization of N-acetyltransferase 1 activity in human keratinocytes and modulation by para-phenylenediamine

Journal of Pharmacology and Experimental Therapeutics

Volumn 334, Issue 1, 2010, Pages 318-326

  Bonifas, Jutta ^a   Scheitza, Simone ^a   Clemens, Judith ^a   Blömeke, Brunhilde ^a  

^a UNIVERSITY OF TRIER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACYLTRANSFERASE; ACYLTRANSFERASE 1; MESSENGER RNA; PHENYLENEDIAMINE; UNCLASSIFIED DRUG;

ACETYLATION; ARTICLE; CELL CULTURE; CELL CYCLE; CELL CYCLE G0 PHASE; CELL CYCLE G1 PHASE; CELL PROLIFERATION; CONCENTRATION RESPONSE; DOWN REGULATION; ENZYME ACTIVITY; HUMAN; HUMAN CELL; KERATINOCYTE; PRIORITY JOURNAL; PROTEIN EXPRESSION; REVERSE TRANSCRIPTION POLYMERASE CHAIN REACTION; WESTERN BLOTTING;

ACETYLATION; ARYLAMINE N-ACETYLTRANSFERASE; CELL CULTURE TECHNIQUES; CELL CYCLE; CELL LINE; CELL PROLIFERATION; CELL SURVIVAL; DOSE-RESPONSE RELATIONSHIP, DRUG; DOWN-REGULATION; ELECTROPHORESIS, POLYACRYLAMIDE GEL; HAIR DYES; HUMANS; ISOENZYMES; KERATINOCYTES; PHENYLENEDIAMINES; REVERSE TRANSCRIPTASE POLYMERASE CHAIN REACTION; SUBSTRATE SPECIFICITY; TIME FACTORS;

EID: 77953763391     PISSN: 00223565     EISSN: 15210103     Source Type: Journal    
DOI: 10.1124/jpet.110.167874     Document Type: Article

References (40)

1. Adam PJ, Berry J, Loader JA, Tyson KL, Craggs G, Smith P, De Belin J, Steers G, Pezzella F, Sachsenmeir KF, et al. (2003) Arylamine N-acetyltransferase-1 is highly expressed in breast cancers and conveys enhanced growth and resistance to etoposide in vitro. Mol Cancer Res 1:826-835.
2. Aeby P, Sieber T, Beck H, Gerberick GF, and Goebel C (2009) Skin sensitization to p-phenylenediamine: the diverging roles of oxidation and N-acetylation for dendritic cell activation and the immune response. J Invest Dermatol 129:99-109.
3. Atmane N, Dairou J, Paul A, Dupret JM, and Rodrigues-Lima F (2003) Redox regulation of the human xenobiotic metabolizing enzyme arylamine Nacetyltransferase 1 (NAT1). Reversible inactivation by hydrogen peroxide. J Biol Chem 278:35086-35092.
4. Barker DF, Husain A, Neale JR, Martini BD, Zhang X, Doll MA, States JC, and Hein DW (2006) Functional properties of an alternative, tissue-specific promoter for human arylamine N-acetyltransferase 1. Pharmacogenet Genomics 16:515-525.
5. Blömeke B, Brans R, Coenraads PJ, Dickel H, Bruckner T, Hein DW, Heesen M, Merk HF, and Kawakubo Y (2009) para-Phenylenediamine and allergic sensitization: risk modification by N-acetyltransferase 1 and 2 genotypes. Brit J Derm 161:1130-1135.
6. Blömeke B, Pietzsch T, and Merk HF (2008) Elicitation response characteristics to mono- and to N,N′-diacetyl-para-phenylenediamine. Contact Dermatitis 58:355-358.
7. Bonifas J, Hennen J, Dierolf D, Kalmes M, and Blömeke B (2010) Evaluation of cytochrome p450 1 (CYP1) and N-acetyltransferase 1 (NAT1) activities in HaCaT cells: implications for the development of in vitro techniques for predictive testing of contact sensitizers. Toxicol in Vitro 24:973-980.
8. 1-S border. Exp Cell Res 68:163-168.
9. Boukamp P, Petrussevska RT, Breitkreutz D, Hornung J, Markham A, and Fusenig NE (1988) Normal keratinization in a spontaneously immortalized aneuploid human keratinocyte cell line. J Cell Biol 106:761-771. (Pubitemid 18089976)
10. Butcher NJ, Arulpragasam A, and Minchin RF (2004) Proteasomal degradation of N-acetyltransferase 1 is prevented by acetylation of the active site cysteine: a mechanism for the slow acetylator phenotype and substrate-dependent down-regulation. J Biol Chem 279:22131-22137.
11. Butcher NJ, Ilett KF, and Minchin RF (2000a) Inactivation of human arylamine N-acetyltransferase 1 by the hydroxylamine of p-aminobenzoic acid. Biochem Pharmacol 60:1829-1836.
12. Butcher NJ, Ilett KF, and Minchin RF (2000b) Substrate-dependent regulation of human arylamine N-acetyltransferase-1 in cultured cells. Mol Pharmacol 57:468-473. (Pubitemid 30140876)
13. Butcher NJ and Minchin RF (2010) Arylamine N-acetyltransferase 1 gene regulation by androgens requires a conserved heat shock element for heat shock factor-1. Carcinogenesis, doi:10.1093/carcin/bgp043.
14. Chun HS, Kuzmicky PA, Kado NY, and Rice RH (2000) Toxicity of Trp-P-2 to cultured human and rat keratinocytes. Chem Biol Interact 127:237-253.
15. Gilroy DW, Saunders MA, Sansores-Garcia L, Matijevic-Aleksic N, and Wu KK (2001) Cell cycle-dependent expression of cyclooxygenase-2 in human fibroblasts. Faseb J 15:288-290.
16. Goebel C, Hewitt NJ, Kunze G, Wenker M, Hein DW, Beck H, and Skare J (2009) Skin metabolism of aminophenols: human keratinocytes as a suitable in vitro model to qualitatively predict the dermal transformation of 4-amino-2-hydroxytoluene in vivo. Toxicol Appl Pharmacol 235:114-123.
17. Hein DW (2002) Molecular genetics and function of NAT1 and NAT2: role in aromatic amine metabolism and carcinogenesis. Mutat Res 506-507:65-77.
18. Hu T, Bailey RE, Morrall SW, Aardema MJ, Stanley LA, and Skare JA (2009) Dermal penetration and metabolism of p-aminophenol and p-phenylenediamine: application of the EpiDerm human reconstructed epidermis model. Toxicol Lett 188:119-129.
19. Huang Z, Senoh Y, Katoh S, and Miwa N (2004) Preventive effects of a water-soluble derivative of chroman moiety of vitamin E on lipid hydroperoxide-induced cell injuries and DNA cleavages through repressions of oxidative stress in the cytoplasm of human keratinocytes. J Cell Biochem 92:425-435.
20. Hueber-Becker F, Nohynek GJ, Meuling WJ, Benech-Kieffer F, and Toutain H (2004) Human systemic exposure to a [14C]-para-phenylenediamine-containing oxidative hair dye and correlation with in vitro percutaneous absorption in human or pig skin. Food Chem Toxicol 42:1227-1236.
21. Jefferson FA, Xiao GH, and Hein DW (2009) 4-Aminobiphenyl down-regulation of NAT2 acetylator genotype-dependent N- and O-acetylation of aromatic and heterocyclic amine carcinogens in primary mammary epithelial cell cultures from rapid and slow acetylator rats. Toxicol Sci 107:293-297.
22. Kalmes M, Neumeyer A, Rio P, Hanenberg H, Fritsche E, and Blömeke B (2006) Impact of the arylhydrocarbon receptor on eugenol- and isoeugenol-induced cell cycle arrest in human immortalized keratinocytes (HaCaT). Biol Chem 387:1201-1207.
23. Kawakubo Y, Merk HF, Masaoudi TA, Sieben S, and Blömeke B (2000) N-acetylation of paraphenylenediamine in human skin and keratinocytes. J Pharmacol Exp Ther 292:150-155. (Pubitemid 30026365)
24. Lee JH, Chung JG, Lai JM, Levy GN, and Weber WW (1997) Kinetics of arylamine N-acetyltransferase in tissues from human breast cancer. Cancer Lett 111:39-50.
25. Liu L, Wagner CR, and Hanna PE (2009) Isoform-selective inactivation of human arylamine N-acetyltransferases by reactive metabolites of carcinogenic arylamines. Chem Res Toxicol 22:1962-1974.
26. McQueen CA and Chau B (2003) Neonatal ontogeny of murine arylamine Nacetyltransferases: implications for arylamine genotoxicity. Toxicol Sci 73:279-286.
27. Meyer A, Blömeke B, and Fischer K (2009) Determination of p-phenylenediamine and its metabolites MAPPD and DAPPD in biological samples using HPLC-DAD and amperometric detection. J Chromatogr B Analyt Technol Biomed Life Sci 877:1627-1633.
28. Moeller R, Lichter J, and Blömeke B (2008) Impact of para-phenylenediamine on cyclooxygenases expression and prostaglandin formation in human immortalized keratinocytes (HaCaT). Toxicology 249:167-175.
29. Nohynek GJ, Duche D, Garrigues A, Meunier PA, Toutain H, and Leclaire J (2005) Under the skin: biotransformation of para-aminophenol and para-phenylenediamine in reconstructed human epidermis and human hepatocytes. Toxicol Lett 158:196-212.
30. Nohynek GJ, Skare JA, Meuling WJ, Hein DW, De Bie AT, and Toutain H (2004) Urinary acetylated metabolites and N-acetyltransferase-2 genotype in human subjects treated with a para-phenylenediamine-containing oxidative hair dye. Food Chem Toxicol 42:1885-1891.
31. Ragunathan N, Dairou J, Pluvinage B, Martins M, Petit E, Janel N, Dupret JM and Rodrigues-Lima F (2008) Identification of the xenobiotic-metabolizing enzyme arylamine N-acetyltransferase 1 (NAT1) as a new target of cisplatin in breast cancer cells: molecular and cellular mechanisms of inhibition. Mol Pharmacol 73:1761-1768.
32. Reilly TP, Lash LH, Doll MA, Hein DW, Woster PM, and Svensson CK (2000) A role for bioactivation and covalent binding within epidermal keratinocytes in sulfonamide-induced cutaneous drug reactions. J Invest Dermatol 114:1164-1173.
33. Rodrigues-Lima F, Dairou J, and Dupret JM (2008) Effect of environmental substances on the activity of arylamine N-acetyltransferases. Curr Drug Metab 9:505-509.
34. Schnuch A, Lessmann H, Frosch PJ, and Uter W. (2008) para- Phenylenediamine: the profile of an important allergen. Results of the IVDK. Br J Dermatol 159:379-386.
35. Sinclair JC, Delgoda R, Noble ME, Jarmin S, Goh NK, and Sim E (1998) Purification, characterization, and crystallization of an N-hydroxyarylamine O-acetyltransferase from Salmonella typhimurium. Protein Expr Purif 12:371-380.
36. Tiang JM, Butcher NJ, and Minchin RF (2010) Small molecule inhibition of arylamine N-acetyltransferase type I inhibits proliferation and invasiveness of MDA-MB-231 breast cancer cells. Biochem Biophys Res Commun 393:95-100.
37. Vindeløv LL, Christensen IJ, and Nissen NI (1983) A detergent-trypsin method for the preparation of nuclei for flow cytometric DNA analysis. Cytometry 3:323-327.
38. Wakefield L, Boukouvala S, and Sim E (2010) Characterisation of CpG methylation in the upstream control region of mouse Nat2: evidence for a gene-environment interaction in a polymorphic gene implicated in folate metabolism. Gene 452:16-21.
39. Wakefield L, Robinson J, Long H, Ibbitt JC, Cooke S, Hurst HC, and Sim E (2008) Arylamine N-acetyltransferase 1 expression in breast cancer cell lines: a potential marker in estrogen receptor-positive tumors. Genes Chromosomes Cancer 47:118-126.
40. Windmill KF, Gaedigk A, Hall PM, Samaratunga H, Grant DM, and McManus ME (2000) Localization of N-acetyltransferases NAT1 and NAT2 in human tissues. Toxicol Sci 54:19-29. (Pubitemid 30152452)