Cytochrome P450 CYP1B1 Interacts with 8-Methoxypsoralen (8-MOP) and Influences Psoralen-Ultraviolet A (PUVA) Sensitivity

PLoS ONE

Volumn 8, Issue 9, 2013, Pages

  Deeni, Yusuf Y ^a,c   Ibbotson, Sally H ^a   Woods, Julie A ^a   Wolf, C Roland ^a,b   Smith, Gillian ^a  

^a UNIVERSITY OF DUNDEE   (United Kingdom)

^b UNIVERSITY OF DUNDEE   (United Kingdom)

^c UNIVERSITY OF ABERTAY DUNDEE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOCHROME P450 1A1; CYTOCHROME P450 1A2; CYTOCHROME P450 1B1; CYTOCHROME P450 2A6; CYTOCHROME P450 2E1; CYTOCHROME P450 REDUCTASE; ESTRADIOL; ETHOXYRESORUFIN; ETHOXYRESORUFIN DEETHYLASE; METHOXSALEN;

ANIMAL CELL; ARTICLE; BACTERIAL MEMBRANE; CHO CELL; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG METABOLISM; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME SUBSTRATE; ESCHERICHIA COLI; GENOTYPE; HUMAN; HUMAN CELL; HUMAN TISSUE; MAMMAL CELL; NONHUMAN; PHOTOSENSITIZATION; PROTEIN EXPRESSION; PROTEIN INTERACTION; PUVA;

ANIMALS; ARYL HYDROCARBON HYDROXYLASES; CHO CELLS; CRICETULUS; CYTOCHROME P-450 ENZYME SYSTEM; ESCHERICHIA COLI; ESTRADIOL; FICUSIN; GENOTYPE; HUMANS; METHOXSALEN; OXAZINES; PSORIASIS; SKIN; ULTRAVIOLET THERAPY;

EID: 84884528391     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0075494     Document Type: Article

References (47)

1. Norris PG, Hawk JLM, Baker C, Bilsland D, Diffey BL, et al. (1994) British Photodermatology Group Guidelines for PUVA. British Journal of Dermatology 130: 246-255.
2. Patel RV, Clark LN, Lebwohl M, Weinberg JM, (2009) Treatments for psoriasis and the risk of malignancy. Journal of the American Academy of Dermatology 60: 1001-1017.
3. Inzinger M, Heschl B, Weger W, Hofer A, Legat FJ, et al. (2011) Efficacy of psoralen plus ultraviolet A therapy vs. biologics in moderate to severe chronic plaque psoriasis: retrospective data analysis of a patient registry. British Journal of Dermatology 165: 640-645.
4. Stern RS, Laird N, (1994) The Carcinogenic Risk of Treatments for Severe Psoriasis. Cancer 73: 2759-2764.
5. Ibbotson SH, Dawe RS, Dinkova-Kostova AT, Weidlich S, Farr PM, et al. (2012) Glutathione S-transferases genotype is associated with sensitivity to psoralen-ultraviolet A photochemotherapy. British Journal of Dermatology 166: 380-388.
6. de Wolff FA, Thomas TV, (1986) Clinical pharmacokinetics of methoxsalen and other psoralens. Clin Pharmacokinet 11: 62-75.
7. Goldstein DP, Carter DM, Ljunggren B, Burkholder J, (1982) Minimal photo-toxic doses and 8-MOP plasma levels in PUVA patients. Journal of Investigative Dermatology 78: 429-433.
8. Marrakchi S, Decloquement L, Pollet P, Briand G, Loesche C, et al. (1991) Variation in 8-methoxypsoralen profiles during long-term psoralen plus ultraviolet-A therapy and correlations between serum 8-methoxypsoralen levels and chromametric parameters. Photodermatology Photoimmunology & Photomedicine 8: 206-211.
9. McLelland J, Fisher C, Farr PM, Diffey BL, Cox NH, (1991) The relationship between plasma psoralen concentration and psoralen UVA erythema. British Journal of Dermatology 124: 585-590.
10. Chen Q, Zhang T, Wang JF, Wei DQ, (2011) Advances in human cytochrome p450 and personalized medicine. Current drug metabolism 12: 436-444.
11. Wolf CR, Smith G, (1999) Pharmacogenetics. British Medical Bulletin 55: 366-386.
12. Smith G, Dawe RS, Clark C, Evans AT, Comrie MM, et al. (2003) Quantitative real-time reverse transcription-polymerase chain reaction analysis of drug metabolizing and cytoprotective genes in psoriasis and regulation by ultraviolet radiation. Journal of Investigative Dermatology 121: 390-398.
13. Smith G, Wolf CR, Deeni YY, Dawe RS, Evans AT, et al. (2003) Cutaneous expression of cytochrome P450CYP2S1: individuality in regulation by therapeutic agents for psoriasis and other skin diseases. Lancet 361: 1336-1343.
14. Ahmad N, Agarwal R, Mukhtar H, (2004) Cytochrome P-450 and drug development for skin diseases. Skin Pharmacology 9: 231-241.
15. Ahmad N, Mukhtar H, (2004) Cytochrome p450: a target for drug development for skin diseases. J Invest Dermatol 123: 417-425.
16. Guengerich FP, (2003) Cytochromes P450, drugs, and diseases. Mol Interv 3: 194-204.
17. Nebert DW, (2000) Drug-metabolizing enzymes, polymorphisms and interindividual response to environmental toxicants. Clin Chem Lab Med 38: 857-861.
18. Li W, Schuler MA, Berenbaum MR, (2003) Diversification of furanocoumarin-metabolizing cytochrome P450 monooxygenases in two papilionids: Specificity and substrate encounter rate. Proc Natl Acad Sci U S A 100Suppl 2: 14593-14598.
19. Wen Z, Pan L, Berenbaum MR, Schuler MA, (2003) Metabolism of linear and angular furanocoumarins by Papilio polyxenes CYP6B1 co-expressed with NADPH cytochrome P450 reductase. Insect Biochem Mol Biol 33: 937-947.
20. Guo LQ, Yamazoe Y, (2004) Inhibition of cytochrome P450 by furanocoumarins in grapefruit juice and herbal medicines. Acta Pharmacol Sin 25: 129-136.
21. Kang A-Y, Young L, Dingfelder C, Peterson S, (2011) Effects of Furanocoumarins from Apiaceous Vegetables on the Catalytic Activity of Recombinant Human Cytochrome P-450 1A2. The Protein Journal 30: 447-456.
22. Girennavar B, Poulose SM, Jayaprakasha GK, Bhat NG, Patil BS, (2006) Furocoumarins from grapefruit juice and their effect on human CYP 3A4 and CYP 1B1 isoenzymes. Bioorganic & Medicinal Chemistry 14: 2606-2612.
23. Goto T, Moriuchi H, Fu X, Ikegawa T, Matsubara T, et al. (2010) The Effects of Single Nucleotide Polymorphisms in CYP2A13 on Metabolism of 5-Methoxypsoralen. Drug Metabolism and Disposition 38: 2110-2116.
24. Ueng Y-F, Chen C-C, Chung Y-T, Liu T-Y, Chang Y-P, et al. (2011) Mechanism-based inhibition of cytochrome P450 (CYP)2A6 by chalepensin in recombinant systems, in human liver microsomes and in mice in vivo. British Journal of Pharmacology 163: 1250-1262.
25. Li DN, Seidel A, Pritchard MP, Wolf CR, Friedberg T, (2000) Polymorphisms in P450CYP1B1 affect the conversion of estradiol to the potentially carcinogenic metabolite 4-hydroxyestradiol. Pharmacogenetics 10: 343-353.
26. Deeni YY, Paine MJI, Ayrton AD, Clarke SE, Chenery R, et al. (2001) Expression, Purification, and Biochemical Characterization of A Human Cytochrome P450 CYP2D6-NADPH Cytochrome P450 Reductase Fusion Protein. Archives of Biochemistry and Biophysics 396: 16-24.
27. Omura T, Sato R, (1964) The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature. J Biol Chem 239: 2370-2378.
28. Gasparro FP, Battista J, Song J, Edelson RL, (1988) Rapid and sensitive analysis of 8-methoxypsoralen in plasma. Journal of Investigative Dermatology 90: 234-236.
29. McNeilly AD, Woods JA, Ibbotson SH, Wolf CR, Smith G, (2011) Characterisation of a Human Keratinocyte HaCaT Cell Line Model to Study the Regulation of Cytochrome P450 CYP2S1. Drug Metabolism and Disposition 40: 283-289.
30. Smith GC, Tew DG, Wolf CR, (1994) Dissection of NADPH-cytochrome P450 oxidoreductase into distinct functional domains. Proceedings of the National Academy of Sciences 91: 8710-8714.
31. Li W, Zangerl AR, Schuler MA, Berenbaum MR, (2004) Characterization and evolution of furanocoumarin-inducible cytochrome P450s in the parsnip webworm, Depressaria pastinacella. Insect Molecular Biology 13: 603-613.
32. Obach RS, Reed-Hagen AE, (2002) Measurement of Michaelis constants for cytochrome P450-mediated biotransformation reactions using a substrate depletion approach. Drug Metab Dispos 30: 831-837.
33. Burke MD, Thompson S, Elcombe CR, Halpert J, Haaparanta T, et al. (1985) Ethoxy-, pentoxy- and benzyloxyphenoxazones and homologues: a series of substrates to distinguish between different induced cytochromes P-450. Biochem Pharmacol 34: 3337-3345.
34. Ding S, Yao D, Deeni YY, Burchell B, Wolf CR, et al. (2001) Human NADPH-P450 oxidoreductase modulates the level of cytochrome P450 CYP2D6 holoprotein via haem oxygenase-dependent and-independent pathways. Biochem J 356: 613-619.
35. Triglia D, Braa SS, Yonan C, Naughton GK, (1991) In vitro toxicity of various classes of test agents using the neutral red assay on a human 3-dimentional physiological skin model. In Vitro Cellular & Developmental Biology 27: 239-244.
36. Mays DC, Hecht SG, Unger SE, Pacula CM, Climie JM, et al. (1987) Disposition of 8-methoxypsoralen in the rat. Induction of metabolism in vivo and in vitro and identification of urinary metabolites by thermospray mass spectrometry. Drug Metab Dispos 15: 318-328.
37. Kharasch ED, Hankins DC, Taraday JK, (2000) Single-dose methoxsalen effects on human cytochrome P-450 2A6 activity. Drug Metab Dispos 28: 28-33.
38. Koenigs LL, Trager WF, (1998) Mechanism-based inactivation of P450 2A6 by furanocoumarins. Biochemistry 37: 10047-10061.
39. von Weymarn LB, Chun JA, Hollenberg PF, (2006) Effects of benzyl and phenethyl isothiocyanate on P450s 2A6 and 2A13: potential for chemoprevention in smokers. Carcinogenesis 27: 782-790.
40. Mammen JS, Kleiner HE, DiGiovanni J, Sutter TR, Strickland PT, (2005) Coumarins are competitive inhibitors of cytochrome P4501B1, with equal potency for allelic variants. Pharmacogenetics and Genomics 15: 183-188.
41. Kleiner HE, Vulimiri SV, Reed MJ, Uberecken A, DiGiovanni J, (2002) Role of cytochrome P450 1a1 and 1b1 in the metabolic activation of 7,12-dimethylbenz[a]anthracene and the effects of naturally occurring furanocoumarins on skin tumor initiation. Chem Res Toxicol 15: 226-235.
42. Koenigs LL, Trager WF, (1998) Mechanism-based inactivation of cytochrome P450 2B1 by 8-methoxypsoralen and several other furanocoumarins. Biochemistry 37: 13184-13193.
43. Tantcheva-Poor I, Servera-Llaneras M, Scharffetter-Kochanek K, Fuhr U, (2001) Liver cytochrome P450 CYP1A2 is markedly inhibited by systemic but not by bath PUVA in dermatological patients. Br J Dermatol 144: 1127-1132.
44. Mukhtar H, Elmets CA, (1996) Photocarcinogenesis: Mechanisms, models and human health implications. Introduction. Photochemistry and Photobiology 63: 355-357.
45. Papadopoulo D, Averbeck D, (1985) Genotoxic effects and DNA photoadducts induced in Chinese hamster V79 cells by 5-methoxypsoralen and 8-methoxypsoralen. Mutation Research/Fundamental and Molecular Mechanisms of Mutagenesis 151: 281-291.
46. Shimada T, Watanabe J, Kawajiri K, Sutter TR, Guengerich FP, et al. (1999) Catalytic properties of polymorphic human cytochrome P450 1B1 variants. Carcinogenesis 20: 1607-1614.
47. Bandiera S, Weidlich S, Harth V, Broede P, Friedberg T, (2005) Proteasomal degradation of human CYP1B1: Effect of the Asn453Ser polymorphism on the post-translational regulation of CYP1B1 expression. Molecular Pharmacology 67: 435-443.