The effect of low molecular weight substances on the skin. Molecular mechanisms and their consequences;Die wirkung kleinmolekularer substanzen auf die menschliche haut. Molekulare mechanismen und konsequenzen

Hautarzt

Volumn 55, Issue 12, 2004, Pages 1125-1129

  Merk, H F ^a,b   Baron, J M ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

^b UNIVERSITY HOSPITAL RWTH AACHEN   (Germany)

Author keywords

Cytochrome P450; Fragrances; p Phenylendiamine; Transporter proteins

Indexed keywords

4 AMINOPHENOL; ACYLTRANSFERASE; ALLERGEN; CYTOCHROME P450; FRAGRANCE; HYDROQUINONE; PHENYLENEDIAMINE; PORPHYRIN;

DIFFUSION; DRUG HYPERSENSITIVITY; HUMAN; KERATINOCYTE; LIVER CELL; MOLECULAR MECHANICS; MOLECULAR WEIGHT; PHOTODYNAMIC THERAPY; PROTEIN TRANSPORT; REVIEW; SKIN; SKIN ALLERGY; SKIN SENSITIZATION;

CARRIER PROTEINS; DERMATITIS, CONTACT; HUMANS; MOLECULAR WEIGHT; PERFUME; PHENYLENEDIAMINES; SKIN; XENOBIOTICS;

EID: 11244286097     PISSN: 00178470     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00105-004-0839-8     Document Type: Review

References (42)

1. Al Masaoudi T, Sieben S, Callahan CP et al. (2001) Eugenol but not isoeugenol induces CYPIA1 mRNA in human keratinocytes. Int Arch Allergy Immunol 124:309-311
2. Baron JM, Heise R, Blaner WS et al. (in press) The 4-oxo-metabolites of retinoic acid are functionally active in human skin cells. J Invest Dermatol
3. Baron JM, Höller D, Schiffer R et al. (2001) Expression of multiple cytochrome P450 enzymes and MDR-associated transport proteins in human skin keratinocytes. J Invest Dermatol 116:541-548
4. Baron JM, Zwadlo-Klarwasser G, Jugert F et al. (1998) Cytochrome P450 1B1: a major P450 isoenzyme in human blood monocytes and macrophage subsets. Biochem Pharmacol 56:1105-1110
5. Basketter DA, Pendlington RU, Saril A, Scholes EW (1996) The role of P450-1A in the activation of prohaptens in skin sensitization. J Invest Dermatol 106:779 [A]
6. Bertrand F, Basketter DA, Roberts DW, Lepoittevin JP (1997) Skin sensitization to Eugenol and isoeugenol in mice: possible metabolic pathways involving ortho-Quinone and quinone methide intermediates. Chem Res Tox 10:335-343
7. Bickers DR, Keogh L, Rifkind AB et al. (1977) Studies in porphyria. VI. Biosynthesis of porphyrins in mammalian skin and in the skin of porphyric patients. J Invest Dermatol 68:5-9
8. Conney AH (1982) Induction of microsomal enzymes by foreign chemicals and carcinogenesis by polycyclic aromatic hydrocarbons: GHA Clowes Memorial Lecture. Cancer Res 42:4875-4917
9. Dickel H, Bruckner T, Bernhard-Klimt C et al. (2002) Surveillance scheme for occupational skin disease in the Saarland, FRG. Cont Derm 46:197-206
10. Dreuw A, Hermanns HM, Heise R et al. (in press) Interleukin-6-type cytokines upregulate expression of multidrug resistance-associated proteins in NHEK and dermal fibroblasts. J Invest Dermatol
11. Fischer IU, von Unruh G, Dengler HJ (1990) The metabolism of eugenol in man. Xenobiotica 20:209-222
12. Friedberg T (1998) Molecular biological methods for characterising drug-metabolizing enzymes in hepatic and extrahepatic tissues. Skin Pharmacol Appl Skin Physiol 11:61-69
13. Gäfvert E, Karlberg AT (1998) Isolation and identification of contact allergens. In: Lepoittevin JP, Basketter DA, Goossens A, Karlberg AT(eds) Allergic contact dermatitis. The molecular basis. Springer, Berlin Heidelberg New York Tokyo, pp 43-67
14. Goerz G, Merk H, Bolsen K et al. (1983) Influence of chronic UV-light exposure on hepatic and cutaneous monooxygenases. Experientia 39:385-386
15. Goh LB, Spears KJ, Yao D et al. (2002) Endogenous drug transporters in in vitro and in vivo models fort he prediction of drug disposition in man. Biochem Pharmacol 64:1569-1578
16. Harris IR, Siefken W, Beck-Oldach K (2002) Comparison of activities dependent on glutathione S-transferase and cytochrome P450 1A1 in cultured keratinocytes and reconstructed epidermal models. Skin Pharmacol Appl Skin Physiol 5:59-67
17. Johansen JD (2002) Fragrance allergy: an overview of an increasing problem. Cont Derm 46 [Suppl 4]:39-40
18. Jugert FK, Agarwal R, Khun A et al. (1994) Multiple cytochrome P450 isoenzymes in murine skin: induction of P450 1A1, 2B, 2E, and 3A by dexamethasone. J Invest Dermatol 102:970-975
19. Kawakubo Y, Merk HF, Massaoudi TA et al. (2000) N-acetylation of paraphenylendiamine in human skin an keratinocytes. J Pharmacol Experiment Therapeut 292 (1):150-155
20. Keeney DS, Skinner C, Wie S et al. (1998) A keratinocyte-specific epoxygenase, CYP2B12, metabolizes arachidonic acid with unusual selectivity, producing a single major epoxyeicosatrienoic acid. J Biol Chem 273:9279-9284
21. Kuipers AL, Van Pelt JP, Bergers M (1998) The effects of oral liarazole on epidermal proliferation and differentiation in severe plaque psoriasis are comparable with those of acitretin. Br J Dermatol 139:380-389
22. Merk H, Mukhtar H, Kaufmann I et al. (1987) Human hair follicle benzo(a)pyrene7,8-diol metabolism: effect of exposure to a coal tar-containing shampoo. J Invest Dermatol 88:71-76
23. Merk H, Rumpf M, Bolsen K et al. (1984) Inducibility of arylhydrocarbon-hydroxylase activity in human hair follicles by topical application of liquor carbonis detergens (coal tar). Br J Dermatol 111:279-284
24. Merk HF, Abel J, Baron JM, Krutmann J (2002) Molecular pathway in dermatotoxicology. Toxicol Appl Pharmacol 195:267-277
25. Merk HF (2002) Allergisches Kontaktekzem. Z Hautkr 77:466-472
26. Nebert DR (2000) Drug-metabolizing enzymes, polymorphisms, and interindividual response to environmental toxicants. Clin Chem Lab Med 38:857-861
27. Reiners JJ, Cantu AR, Thai G (1992) Differential expression of basal and hydrocarbon induced cytochrome P450 monooxygenase and quinone reductase activities in subpopulations of murine epidermal cells differing in their stages of differentiation. Drug Met Dispos 20:360-366
28. Renton KW (2000) Hepatic drug metabolism and immunostimulation. Toxicology 142:173-178
29. Schäfer T, Böhler E, Ruhdorfer S et al. (2001) Epidemiology of contact allergy in adults. Allergy 56:1192-1196
30. Schiffer R, Neis M, Höller D et al. (2003) Active influx transport is mediated by members of the organic anion transporting polypeptide family in human epidermal keratinocytes. J Invest Dermatol 120:285-291
31. Schröder C, Lichtental C, Merk HF (2001) Henna-Tä towierung. Z Hautkr 76:758
32. Sieben S, Baron JM, Blömeke B, Merk HF (1999) Multiple cytochrome P450 isoenzymes mRNA are expressed in dendritic cells. Int Arch Allergy Immunol 118:358-361
33. Sieben S, Hertl M, Massaoudi TA et al. (2001) Characterization of T cell responses to fragrances. Toxicol Appl Pharmacol 172:172-178
34. Sieben S, Kawakubo Y, Massaoudi TA et al. (2002) Delayed-type hypersensitivity reaction to paraphenylendiamine is mediated by 2 different pathways of antigen recognition by specific αβ+human T-cell clones. J Allergy Clin Immunol 109:1005-1011
35. Sieben S, Kawakubo Y, Sachs B et al. (2001) T cell responses to paraphenylenediamine and to its metabolites mono-, and diacetyl- paraphenylenediamine. Int Arch Allergy Immunol 124:356-358
36. Smith G, Wolf CR, Deeni YY et al. (2003) Cutaneous expression of cytochrome P450 CYP2S1: individuality in regulation by therapeutic agents for psoriasis and other skin diseases. Lancet 361:1336-1343
37. Stark K, Törma H, Cristea M, Oliw EH (2003) Expression of CYP4F8 (prostaglandin H 19-hydroxylase) in human epithelia and prominent induction in epidermis of psoriatic lesions. Arch Biochem Biophys 409:188-196
38. Stauber KL, Laskin JD, Yurkow EJ (2000) Flow cytometry reveals subpopulations of murine epidermal cells that are refractory to induction of cytochrome P-450 1A1 by β-naphthoflavone. J Pharm Exp Ther 293:304-312
39. Sumenicht S (1994) Die Wirkung von Eugenol auf fremdstoffmetabolisierende Enzyme. Inauguraldissertation, Köln
40. Tamai I, Nezu J, Uchino H et al. (2000) Molecular identification and characterisation of novel members of the human organic anion transporter (OATP) family. Biochem Biophys Res Commun 273:251-260
41. Wattenberg LW, Leong JL (1962) Histochemical studies of polycyclic hydrocarbon metabolizing systems. J Histochem Soc 10:659
42. Wulferink M, Dierkes S, Gleichmann E (2002) Cross-sensitization to haptens: formation of common haptenic metabolites, T cell recognition of cryptic peptides, and true T cell cross-reactivity. Eur J Immunol 32:1338-1348