Effects of the genotoxic compounds, benzo[a]pyrene and cyclophosphamide on phase 1 and 2 activities in EpiDerm™ models

References

• Aardema MJ, Barnett BC, Khambatta Z, Reisinger K, Ouedraogo-Arras G, Faquet B, Ginestet AC, Mun GC, Dahl EL, Hewitt NJ, Corvi R, Curren RD. (2010). International prevalidation studies of the EpiDerm 3D human reconstructed skin micronucleus (RSMN) assay: transferability and reproducibility. Mutat Res 701:123–131.
   PubMed Web of Science ®Google Scholar
• Ahmad N, Mukhtar H. (2004). Cytochrome p450: a target for drug development for skin diseases. J Invest Dermatol 123:417–425.
   PubMed Web of Science ®Google Scholar
• Afaq F, Zaid MA, Pelle E, Khan N, Syed DN, Matsui MS, Maes D, Mukhtar H. (2009). Aryl hydrocarbon receptor is an ozone sensor in human skin. J Invest Dermatol 129:2396–2403.
   PubMed Web of Science ®Google Scholar
• Beckley-Kartey SAJ, Swales NJ, Hotchkiss SAM. (1997). The cutaneous metabolism of testosterone. Hum Exp Toxicol 16:51.
   Google Scholar
• Bennett PN, Blackwell E, Davies DS. (1975). Competition for sulphate during detoxification in the gut wall. Nature 258:247–248.
   PubMed Web of Science ®Google Scholar
• Brown HS, Griffin M, Houston JB. (2007). Evaluation of cryopreserved human hepatocytes as an alternative in vitro system to microsomes for the prediction of metabolic clearance. Drug Metab Dispos 35:293–301.
   PubMed Web of Science ®Google Scholar
• Cao J, Leibold E, Beisker W, Schranner T, Nüsse M, Schwarz LR. (1993). Flow cytometric analysis of in vitro micronucleus induction in hepatocytes treated with carcinogens. Toxicol In Vitro, 7, 447–451.
   PubMed Web of Science ®Google Scholar
• Chang TK, Yu L, Maurel P, Waxman DJ. (1997). Enhanced cyclophosphamide and ifosfamide activation in primary human hepatocyte cultures: response to cytochrome P-450 inducers and autoinduction by oxazaphosphorines. Cancer Res 57:1946–1954.
   PubMed Web of Science ®Google Scholar
• Chuong CM, Nickoloff BJ, Elias PM, Goldsmith LA, Macher E, Maderson PA, Sundberg JP, Tagami H, Plonka PM, Thestrup-Pederson K, Bernard BA, Schröder JM, Dotto P, Chang CM, Williams ML, Feingold KR, King LE, Kligman AM, Rees JL, Christophers E. (2002). What is the ‘true’ function of skin? Exp Dermatol 11:159–187.
   PubMed Web of Science ®Google Scholar
• Costa C, Catania S, De Pasquale R, Stancanelli R, Scribano GM, Melchini A. (2010). Exposure of human skin to benzo[a]pyrene: role of CYP1A1 and aryl hydrocarbon receptor in oxidative stress generation. Toxicology 271:83–86.
   PubMed Web of Science ®Google Scholar
• Curren RD, Mun GC, Gibson DP, Aardema MJ. (2006). Development of a method for assessing micronucleus induction in a 3D human skin model (EpiDerm). Mutat Res 607:192–204.
   PubMed Web of Science ®Google Scholar
• Dahl EL, Curren R, Barnett BC, Khambatta Z, Reisinger K, Ouedraogo G, Faquet B, Ginestet AC, Mun G, Hewitt NJ, Carr G, Pfuhler S, Aardema MJ. (2011). The reconstructed skin micronucleus assay (RSMN) in EpiDerm™: detailed protocol and harmonized scoring atlas. Mutat Res 720:42–52.
   PubMed Web of Science ®Google Scholar
• Dirven HA, van Ommen B, van Bladeren PJ. (1994). Involvement of human glutathione S-transferase isoenzymes in the conjugation of cyclophosphamide metabolites with glutathione. Cancer Res 54:6215–6220.
   PubMed Web of Science ®Google Scholar
• Elhajouji A, Santos AP, Van Hummelen P, Kirsch-Volders M. (1994). Metabolic differences between whole blood and isolated lymphocyte cultures for micronucleus (MN) induction by cyclophosphamide and benzo[a]pyrene. Mutagenesis 9:307–313.
   PubMed Web of Science ®Google Scholar
• EU, 2003. EC - Directive 2003/15/EC of the European Parliament and of the Council of 27 February 2003 amending Council Directive 76/768/EEC on the approximation of the laws of the Member States relating to cosmetic products. Official Journal L66, 11/03/2003 p.26.
   Google Scholar
• Flamand N, Marrot L, Belaidi JP, Bourouf L, Dourille E, Feltes M, Meunier JR. (2006). Development of genotoxicity test procedures with Episkin, a reconstructed human skin model: towards new tools for in vitro risk assessment of dermally applied compounds? Mutat Res 606:39–51.
   PubMed Web of Science ®Google Scholar
• Gautier JC, Lecoeur S, Cosme J, Perret A, Urban P, Beaune P, Pompon D. (1996). Contribution of human cytochrome P450 to benzo[a]pyrene and benzo[a]pyrene-7,8-dihydrodiol metabolism, as predicted from heterologous expression in yeast. Pharmacogenetics 6:489–499.
   PubMedGoogle Scholar
• Gervot L, Rochat B, Gautier JC, Bohnenstengel F, Kroemer H, de Berardinis V, Martin H, Beaune P, de Waziers I. (1999). Human CYP2B6: expression, inducibility and catalytic activities. Pharmacogenetics 9:295–306.
   PubMedGoogle Scholar
• Goebel C, Hewitt NJ, Kunze G, Wenker M, Hein DW, Beck H, 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.
   PubMed Web of Science ®Google Scholar
• Guy RH, Mak VHW, Kai T, Bommannan D, Potts RO. (1990). Percutaneous penetration enhancers: mode of Action. In: Scott, R.C., Guy, R.H., Hadgraft, J., eds. Prediction of Percutaneous Penetrationm Methods, Measurements and Modelling. London: IBC, 213–223.
   Google Scholar
• Habig WH, Pabst MJ, Jakoby WB. (1974). Glutathione S-transferases. The first enzymatic step in mercapturic acid formation. J Biol Chem 249:7130–7139.
   PubMed Web of Science ®Google Scholar
• Heath EC, Dingell JV. (1974). The interaction of foreign chemical compounds with the glucuronidation of estrogens in vitro. Drug Metab Dispos 2:556–565.
   PubMed Web of Science ®Google Scholar
• Hikima T, Maibach HI. (2007). Gender differences of enzymatic activity and distribution of 17beta-hydroxysteroid dehydrogenase in human skin in vitro. Skin Pharmacol Physiol 20:168–174.
   Google Scholar
• Hu T, Bailey RE, Morrall SW, Aardema MJ, Stanley LA, Skare JA. (2009b). Dermal penetration and metabolism of p-aminophenol and p-phenylenediamine: application of the EpiDerm human reconstructed epidermis model. Toxicol Lett 188:119–129.
   PubMed Web of Science ®Google Scholar
• Hvastkovs EG, So M, Krishnan S, Bajrami B, Tarun M, Jansson I, Schenkman JB, Rusling JF. (2007). Electrochemiluminescent arrays for cytochrome P450-activated genotoxicity screening. DNA damage from benzo[a]pyrene metabolites. Anal Chem 79:1897–1906.
   PubMed Web of Science ®Google Scholar
• Khan WA, Park SS, Gelboin HV, Bickers DR, Mukhtar H. (1989). Epidermal cytochrome P-450: immunochemical characterization of isoform induced by topical application of 3-methylcholanthrene to neonatal rat. J Pharmacol Exp Ther 249:921–927.
   PubMed Web of Science ®Google Scholar
• LeCluyse E, Madan A, Hamilton G, Carroll K, DeHaan R, Parkinson A. (2000). Expression and regulation of cytochrome P450 enzymes in primary cultures of human hepatocytes. J Biochem Mol Toxicol 14:177–188.
   PubMed Web of Science ®Google Scholar
• Li W, Harper PA, Tang BK, Okey AB. (1998). Regulation of cytochrome P450 enzymes by aryl hydrocarbon receptor in human cells: CYP1A2 expression in the LS180 colon carcinoma cell line after treatment with 2,3,7,8-tetrachlorodibenzo-p-dioxin or 3-methylcholanthrene. Biochem Pharmacol 56:599–612.
   PubMed Web of Science ®Google Scholar
• Lindley C, Hamilton G, McCune JS, Faucette S, Shord SS, Hawke RL, Wang H, Gilbert D, Jolley S, Yan B, LeCluyse EL. (2002). The effect of cyclophosphamide with and without dexamethasone on cytochrome P450 3A4 and 2B6 in human hepatocytes. Drug Metab Dispos 30:814–822.
   PubMed Web of Science ®Google Scholar
• Luu-The V, Duche D, Ferraris C, Meunier JR, Leclaire J, Labrie F. (2009). Expression profiles of phases 1 and 2 metabolizing enzymes in human skin and the reconstructed skin models Episkin and full thickness model from Episkin. J Steroid Biochem Mol Biol 116:178–186.
   PubMed Web of Science ®Google Scholar
• Mackenzie PI, Rodbourn L, Iyanagi T. (1993). Glucuronidation of carcinogen metabolites by complementary DNA-expressed uridine 5′-diphosphate glucuronosyltransferases. Cancer Res 53:1529–1533.
   PubMed Web of Science ®Google Scholar
• Milewich L, Kaimal V, Shaw CB, Sontheimer. (1986). Epidermal keratinocytes: a source of 5 alpha-dihydrotestosterone production in human skin. J Clin Endocrinol Metab 62:739–746.
   PubMed Web of Science ®Google Scholar
• Mukhtar H, Bickers DR. (1981). Drug metabolism in skin. Comparative activity of the mixed-function oxidases, epoxide hydratase, and glutathione S-transferase in liver and skin of the neonatal rat. Drug Metab Dispos 9:311–314.
   PubMed Web of Science ®Google Scholar
• Mun GC, Aardema MJ, Hu T, Barnett B, Kaluzhny Y, Klausner M, Karetsky V, Dahl EL, Curren RD. (2009). Further development of the EpiDerm 3D reconstructed human skin micronucleus (RSMN) assay. Mutat Res 673:92–99.
   PubMed Web of Science ®Google Scholar
• Nims RW, Prough RA, Lubet RA. (1984). Cytosol-mediated reduction of resorufin: a method for measuring quinone oxidoreductase. Arch Biochem Biophys 229:459–465.
   PubMed Web of Science ®Google Scholar
• Nohynek GJ, Duche D, Garrigues A, Meunier PA, Toutain H, 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.
   PubMed Web of Science ®Google Scholar
• Oesch F, Fabian E, Oesch-Bartlomowicz B, Werner C, Landsiedel R. (2007). Drug-metabolizing enzymes in the skin of man, rat, and pig. Drug Metab Rev 39:659–698.
   PubMed Web of Science ®Google Scholar
• Pelkonen O, Nebert DW. (1982). Metabolism of polycyclic aromatic hydrocarbons: etiologic role in carcinogenesis. Pharmacol Rev 34:189–222.
   PubMed Web of Science ®Google Scholar
• Pushparajah DS, Umachandran M, Nazir T, Plant KE, Plant N, Lewis DF, Ioannides C. (2008a). Up-regulation of CYP1A/B in rat lung and liver, and human liver precision-cut slices by a series of polycyclic aromatic hydrocarbons; association with the Ah locus and importance of molecular size. Toxicol In Vitro 22:128–145.
   PubMed Web of Science ®Google Scholar
• Pushparajah DS, Umachandran M, Plant KE, Plant N, Ioannides C. (2008b). Up-regulation of the glutathione S-transferase system in human liver by polycyclic aromatic hydrocarbons; comparison with rat liver and lung. Mutagenesis 23:299–308.
   PubMed Web of Science ®Google Scholar
• Raza H, Mukhtar H. (1993). Differences in inducibility of cytochrome P-4501A1, monooxygenases and glutathione S-transferase in cutaneous and extracutaneous tissues after topical and parenteral administration of beta-naphthoflavone to rats. Int J Biochem 25:1511–1516.
   PubMedGoogle Scholar
• Raza H, Awasthi YC, Zaim MT, Eckert RL, Mukhtar H. (1991). Glutathione S-transferases in human and rodent skin: multiple forms and species-specific expression. J Invest Dermatol 96:463–467.
   PubMed Web of Science ®Google Scholar
• Schäfer-Korting M, Mahmoud A, Lombardi Borgia S, Brüggener B, Kleuser B, Schreiber S, Mehnert W. (2008). Reconstructed epidermis and full-thickness skin for absorption testing: influence of the vehicles used on steroid permeation. Altern Lab Anim 36:441–452.
   PubMed Web of Science ®Google Scholar
• Skare JA, Hewitt NJ, Doyle E, Powrie R, Elcombe C. (2009). Metabolite screening of aromatic amine hair dyes using in vitro hepatic models. Xenobiotica 39:811–825.
   PubMed Web of Science ®Google Scholar
• Sherratt PJ, Hayes JD. (2002). Glutathione S-transferases. In: Ioannides C, ed. Enzyme systems that metabolise drugs and other xenobiotics. Chichester, UK: Wiley & Sons, 319–352.
   Google Scholar
• Slominski A, Wortsman J, Foecking MF, Shackleton C, Gomez-Sanchez C, Szczesniewski A. (2002). Gas chromatography/mass spectrometry characterization of corticosteroid metabolism in human immortalized keratinocytes. J Invest Dermatol 118:310–315.
   Google Scholar
• Slominski A, Zjawiony J, Wortsman J, Semak I, Stewart J, Pisarchik A, Sweatman T, Marcos J, Dunbar C, C Tuckey R. (2004). A novel pathway for sequential transformation of 7-dehydrocholesterol and expression of the P450scc system in mammalian skin. Eur J Biochem 271:4178–4188.
   PubMedGoogle Scholar
• Swanson HI. (2004). Cytochrome P450 expression in human keratinocytes: an aryl hydrocarbon receptor perspective. Chem Biol Interact 149:69–79.
   PubMed Web of Science ®Google Scholar
• Tachibana S, Tanaka M. (2001). Simultaneous determination of testosterone metabolites in liver microsomes using column-switching semi-microcolumn high-performance liquid chromatography. Anal Biochem 295:248–256.
   PubMed Web of Science ®Google Scholar
• van de Sandt JJ, van Burgsteden JA, Cage S, Carmichael PL, Dick I, Kenyon S, Korinth G, Larese F, Limasset JC, Maas WJ, Montomoli L, Nielsen JB, Payan JP, Robinson E, Sartorelli P, Schaller KH, Wilkinson SC, Williams FM. (2004). In vitro predictions of skin absorption of caffeine, testosterone, and benzoic acid: a multi-centre comparison study. Regul Toxicol Pharmacol, 39(3), 271–281.
   Google Scholar
• Wei W, Zhang C, Liu AL, Xie SH, Chen XM, Lu WQ. (2009). Effect of PCB153 on BaP-induced genotoxicity in HepG2 cells via modulation of metabolic enzymes. Mutat Res 675:71–76.
   PubMed Web of Science ®Google Scholar
• Xie HJ, Yasar U, Lundgren S, Griskevicius L, Terelius Y, Hassan M, Rane A. (2003). Role of polymorphic human CYP2B6 in cyclophosphamide bioactivation. Pharmacogenomics J 3:53–61.
   PubMed Web of Science ®Google Scholar
• Yamazaki H, Shimada T. (1997). Progesterone and testosterone hydroxylation by cytochromes P450 2C19, 2C9, and 3A4 in human liver microsomes. Arch Biochem Biophys 346:161–169.
   PubMed Web of Science ®Google Scholar
• Zhang Y, Gonzalez V, Xu MJ. (2002). Expression and regulation of glutathione S-transferase P1-1 in cultured human epidermal cells. J Dermatol Sci 30:205–214.
   PubMed Web of Science ®Google Scholar
• Zhao JF, Zhang YJ, Kubilus J, Jin XH, Santella RM, Athar M, Wang ZY, Bickers DR. (1999). Reconstituted 3-dimensional human skin as a novel in vitro model for studies of carcinogenesis. Biochem Biophys Res Commun 254:49–53.
   PubMed Web of Science ®Google Scholar
• Zuber R, Anzenbacherová E, Anzenbacher P. (2002). Cytochromes P450 and experimental models of drug metabolism. J Cell Mol Med 6:189–198.
   PubMed Web of Science ®Google Scholar