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

Toxicology and Applied Pharmacology

Volumn 235, Issue 1, 2009, Pages 114-123

  Goebel, C ^a   Hewitt, N J ^b   Kunze, G ^c   Wenker, M ^d   Hein, D W ^e   Beck, H ^c   Skare, J ^a  

^a PROCTER AND GAMBLE COMPANY   (United States)

^b Cosmital SA ^*  (Germany)

^c Wella Cosmital SA   (Switzerland)

^d Notox BV   (Netherlands)

^e University of Louisville School of Medicine   (United States)

Author keywords

Dermal in vitro models, metabolism 4 Amino 2 hydroxytolune

Indexed keywords

4 AMINO 2 HYDROXYTOLUENE; 4 AMINOBENZOIC ACID; 4 AMINOPHENOL; ACYLTRANSFERASE; AMINOPHENOL DERIVATIVE; UNCLASSIFIED DRUG;

ACETYLATION; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; DRUG TRANSFORMATION; FEMALE; FIRST PASS EFFECT; HUMAN; HUMAN CELL; NONHUMAN; PREDICTION; QUALITATIVE ANALYSIS; RAT; SKIN TOXICITY; TOXICOKINETICS;

4-AMINOBENZOIC ACID; ADULT; ANILINE COMPOUNDS; ANIMALS; ARYLAMINE N-ACETYLTRANSFERASE; CELLS, CULTURED; CRESOLS; FEMALE; GENOTYPE; HUMANS; ISOENZYMES; KERATINOCYTES; MIDDLE AGED; MOLECULAR STRUCTURE; PHENOLS; RATS; RATS, WISTAR; SKIN;

ANIMALIA;

EID: 59149093103     PISSN: 0041008X     EISSN: 10960333     Source Type: Journal    
DOI: 10.1016/j.taap.2008.11.014     Document Type: Article

References (45)

1. Andres H.H., Klem A.J., Szabo S.M., and Weber W.W. New spectrophotometric and radiochemical assays for acetyl-CoA: arylamine N-acetyltransferase applicable to a variety of arylamines. Anal. Biochem. 145 2 (1985) 367-375
2. Altenburger R., and Kissel T. The human keratinocyte cell line HaCaT: an in vitro cell culture model for keratinocyte testosterone metabolism. Pharm. Res. 16 5 (1999) 766-771
3. Baron J., Kawabata T.T., Redick J.A., Knapp S.A., Wick D.G., Wallace R.B., Jacoby W.B., and Guengerich F.P. Localisation of carcinogen-metabolising enzymes in human and animal tissues. In: Rydstrom J., Montelius J., and Bengtsson M. (Eds). Extrahepatic Drug Metabolism and Chemical Carcinogenesis (1983), Elsevier, Amsterdam 73-88
4. Bhaiya P., Roychowdhury S., Vyas P.M., Doll M.A., Hein D.W., and Svensson C.K. Bioactivation, protein haptenation, and toxicity of sulfamethoxazole and dapsone in normal human dermal fibroblasts. Tox. Appl. Pharmacol. 215 2 (2006) 158-167
5. Boukamp P., Petrussevska R.T., Breitkreutz D., Hornung J., Markham A., and Fusenig N.E. Normal keratinization in a spontaneously immortalized aneuploid human keratinocyte cell line. J. Cell Biol. 106 3 (1988) 761-771
6. Boukouvala S., and Fakis G. Arylamine N-acetyltransferases: what we learn from genes and genomes. Drug Metab. Rev. 37 3 (2005) 511-564
7. Bronaugh R.L., Collier S.W., Macpherson S.E., and Kraeling M.E. Influence of metabolism in skin on dosimetry after topical exposure. Environmental Health Perspect. 102 Suppl. 11 (1994) 71-74
8. Brown K.C. Hair coloring. In: Johnson D. (Ed). Hair and Hair Care (1997), Marcel Dekker, NY 191-215
9. Butcher N.J., Ilett K.F., and Minchin R.F. Substrate-dependent regulation of human arylamine N-acetyltransferase-1 in cultured cells. Mol. Pharm. 57 3 (2000) 468-473
10. Doll M.A., and Hein D.W. Comprehensive human NAT2 genotype method using single nucleotide polymorphism-specific polymerase chain reaction primers and fluorogenic probes. Anal. Biochem. 288 (2001) 106-108
11. Doll M.A., and Hein D.W. Rapid genotype method to distinguish frequent and/or functional polymorphisms in human N-acetyltransferase-1 (NAT1). Anal. Biochem. 301 (2002) 328-332
12. Dressler W.E., and Appelqvist T. Plasma/blood pharmacokinetics and metabolism after dermal exposure to para-aminophenol or para-phenylenediamine. Food Chem. Toxicol. 44 3 (2006) 371-379
13. Dupret J.M., Goodfellow G.H., Janezic S.A., and Grant D.M. Structure-function studies of human arylamine N-acetyltransferases NAT1 and NAT2. Functional analysis of recombinant NAT1/NAT2 chimeras expressed in Escherichia coli. J. Biol. Chem. 269 43 (1994) 26830-26835
14. Eggenreich K., Golouch S., Töscher B., Beck H., Kuehnelt D., and Wintersteiger R.J. Determination of 4-amino-m-cresol and 5-amino-o-cresol and metabolites in human keratinocytes (HaCaT) by high-performance liquid chromatography with DAD and MS detection. Biochem. Biophys. Methods 61 1-2 (2004) 23-34
15. Finnen M.J. Skin metabolism by oxidation and conjugation. In: Shroot B., and Schaefer H. (Eds). Pharmacology and the Skin. Volume 1. Skin Pharmacokinetics (1987), Karger, Basel 163-169
16. Franz T.J. Kinetics of cutaneous drug penetration. Int. J. Dermatol. 22 9 (1983) 499-505
17. Guy R.H., Mak V.H.W., Kai T., Bommannan D., and Potts R.O. Percutaneous penetration enhancers: mode of action. In: Scott R.C., Guy R.H., and Hadgraft J. (Eds). Prediction of Percutaneous Penetration Methods, Measurements and Modelling (1990), IBC, London 213-223
18. Hedtke B., Gao Z., Chen L.J., Weber W.M., and Dix K.J. Metabolism and disposition of [14C]5-amino-o-cresol in female F344 rats and B6C3F1 mice. Xenobiotica 38 2 (2008) 171-184
19. Hewitt P.G., Perkins J., and Hotchkiss S.A. Metabolism of fluroxypyr, fluroxypyr methyl ester, and the herbicide fluroxypyr methylheptyl ester. I: during percutaneous absorption through fresh rat and human skin in vitro. Drug Metab. Dispos. 28 7 (2000) 748-754
20. Hinz R.S., Lorence C.R., Hodson C.D., Hansch C., Hall L.L., and Guy R.H. Percutaneous penetration of para-substituted phenols in vitro. Fundam. Appl. Toxicol. 17 3 (1991) 575-583
21. Hoath S.B., and Leahy D.G. The organization of human epidermis: functional epidermal units and phi proportionality. J. Invest. Dermatol. 121 6 (2003) 1440-1446
22. Holland J.M., Kao J.Y., and Whitaker M.J. A multisample apparatus for kinetic evaluation of skin penetration in vitro: the influence of viability and metabolic status of the skin. Toxicol. Appl. Pharmacol. 72 2 (1984) 272-280
23. Hotchkiss S.A., Chidgey M.A., Rose S., and Caldwell J. Percutaneous absorption of benzyl acetate through rat skin in vitro. 1. Validation of an in vitro model against in vivo data. Food Chem. Toxicol. 28 6 (1990) 443-447
24. Janmohamed A., Dolphin C.T., Phillips I.R., and Shephard E.A. Quantification and cellular localization of expression in human skin of genes encoding flavin-containing monooxygenases and cytochromes P450. Biochem. Pharmacol. 62 6 (2001) 777-786
25. Järvinen A., Granander M., Nykänen S., Laine T., Geurts P., and Viitanen A. Steady-state pharmacokinetics of oestradiol gel in post-menopausal women: effects of application area and washing. BJOG 104 Suppl. 16 (1997) 14-18
26. Kastings G.B., Smith R.L., and Cooper E.R. Effect of lipid solubility and molecular size on percutaneous absorption. In: Shroot B., and Schaefer H. (Eds). Pharmacology of the Skin (1987), Kager, Basel 138-153
27. Kawakubo Y., Yamazoe Y., Kato R., and Nishikawa T. High capacity of human skin for N-acetylation of arylamines. Skin Pharmacol. 3 3 (1990) 180-185
28. Kawakubo Y., Merk H.F., Masaoudi T.A., Sieben S., and Blömeke B. N-Acetylation of paraphenylenediamine in human skin and keratinocytes. J. Pharmacol. Exp. Ther. 292 1 (2000) 150-155
29. Löffler B.M., and Kunze H. Refinement of the coomassie brilliant blue G assay for quantitative protein determination. Anal. Biochem. 177 1 (1989) 100-102
30. Nohynek G.J., Duche D., Garrigues A., Meunier P.A., Toutain H., and Leclaire J. Under the skin: biotransformation of para-aminophenol and para-phenylenediamine in reconstructed human epidermis and human hepatocytes. Toxicol. Lett. 158 3 (2005) 196-212
31. Organisation for Economic Co-operation and Development (OECD). OECD Guidelines for Testing of Chemicals, Section 4, Health Effects, Number 427:. "Percutaneous Absorption: In Vivo Method" (2004) adopted April 13
32. Organisation for Economic Co-operation and Development (OECD). Guidelines for Testing of Chemicals, Section 4, Health Effects, Number 428: "Percutaneous Absorption: In Vitro Method" (2004) adopted April 13
33. Potts R.O., Bommannan B., and Guy R.H. Percutaneous absorption. In: Mukhtar H. (Ed). Pharmacology of the Skin (1992), CRC Press, USA 12-27
34. SCCP(EU Scientific Committee on Consumer Products) (10 October 2006). Opinion on 4-amino-2-hydroxytoluene. pp 1-38. (http://ec.europa.eu/health/ph_risk/committees/04_sccp/docs/sccp_o_070.pdf).
35. Schadow A., Scholz-Pedretti K., Lambeau G., Gelb M.H., Fürstenberger G., Pfeilschifter J., and Kaszkin M. Characterization of group X phospholipase A(2) as the major enzyme secreted by human keratinocytes and its regulation by the phorbol ester TPA. J. Invest. Dermatol. of 116 1 (2001) 31-39
36. Skare J.A., Powrie R., and Elcombe C. Metabolite Screening of Aromatic Amines Using In Vitro Hepatic Models (2008) Submitted
37. Skare J.A., Powrie R., Meuling W., Hein D.W., Duche D., and Nohynek G.J. Metabolism of oxidative hair dyes-a key consideration for safety assessment. SOT Seattle 2008. The Toxicologist 102 1 (2008) 134
38. Smith C.K., and Hotchkiss S.A.M. Allergic Contact Dermatitis: Chemical and Metabolic Mechanisms (2001), Taylor and Francis, London
39. Storm J.E., Collier S.W., Stewart R.F., and Bronaugh R.L. Metabolism of xenobiotics during percutaneous penetration: role of absorption rate and cutaneous enzyme activity. Fundam. Appl. Toxicol. 15 1 (1990) 132-141
40. Villard P.H., Sampol E., Elkaim J.L., Puyoou F., Casanova D., Sérée E., Durand A., and Lacarelle B. Increase of CYP1B1 transcription in human keratinocytes and HaCaT cells after UV-B exposure. Toxicol. Appl. Pharmacol. 178 3 (2002) 137-143
41. Weber W.W., and Hein D.W. N-acetylation pharmacogenetics. Pharmacol. Rev. 37 (1985) 25-79
42. Wilhelm K.P., Böttjer B., and Siegers C.P. Quantitative assessment of primary skin irritants in vitro in a cytotoxicity model: comparison with in vivo human irritation tests. Br. J. Dermatol. 145 5 (2001) 709-715
43. Zenser T.V., Lakshmi V.M., Rustan T.D., Doll M.A., Deitz A.C., Davis B.B., and Hein D.W. Human N-acetylation of benzidine: role of NAT1 and NAT2. Cancer Res. 56 17 (1996) 3941-3947
44. Zhang Y., Gonzalez V., and Xu M.J. Expression and regulation of glutathione S-transferase P1-1 in cultured human epidermal cells. J. Dermatol. Sci. 30 3 (2002) 205-214
45. Zhu Q.G., Hu J.H., Liu J.Y., Lu S.W., Liu Y.X., and Wang J. Stereoselective characteristics and mechanisms of epidermal carboxylesterase metabolism observed in HaCaT keratinocytes. Biol. Pharm. Bull. 30 3 (2007) 532-536