Cytochrome P450 CYP1A1: Wider roles in cancer progression and prevention

BMC Cancer

Volumn 9, Issue , 2009, Pages

  Androutsopoulos, Vasilis P ^a   Tsatsakis, Aristidis M ^a   Spandidos, Demetrios A ^a  

^a UNIVERSITY OF CRETE   (Greece)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC HYDROCARBON RECEPTOR; CYTOCHROME P450 1A1; CYTOCHROME P450 1A2; CYTOCHROME P450 2A6; ESTROGEN RECEPTOR; GLUCOCORTICOID RECEPTOR; HEAT SHOCK PROTEIN 90; MITOGEN ACTIVATED PROTEIN KINASE;

APOPTOSIS; CANCER GROWTH; CANCER PREVENTION; CARCINOGENESIS; CELL CYCLE REGULATION; CELLULAR DISTRIBUTION; DETOXIFICATION; ENVIRONMENTAL EXPOSURE; ENZYME ACTIVATION; ENZYME ACTIVITY; ENZYME INDUCTION; ENZYME METABOLISM; ENZYME PHOSPHORYLATION; ENZYME POLYMORPHISM; ENZYME SPECIFICITY; ENZYME STRUCTURE; GENE MUTATION; HUMAN; HYDROLYSIS; HYPOXIA; LIVER METABOLISM; NONHUMAN; PROTEIN EXPRESSION; PROTEIN FUNCTION; REVIEW; SIGNAL TRANSDUCTION; XENOBIOTIC METABOLISM; ANIMAL; DISEASE COURSE; ENZYMOLOGY; METABOLISM; NEOPLASM; PATHOLOGY;

ANIMALS; CYTOCHROME P-450 CYP1A1; DISEASE PROGRESSION; HUMANS; NEOPLASMS;

EID: 67650074960     PISSN: None     EISSN: 14712407     Source Type: Journal    
DOI: 10.1186/1471-2407-9-187     Document Type: Review

References (135)

1. Wei Q Gu J Cheng L Bondy ML Jiang H Hong WK Spitz MR Benzo[a]pyrene diol epoxide-induced chromosomal aberrations and risk of lung cancer Cancer Res 1996, 56:3975-3979. 8752166
2. Buterin T Hess MT Luneva N Geacintov NE Amin S Kroth H Seidel A Naegeli H Unrepaired fjord region polycyclic aromatic hydrocarbon-DNA adducts in ras codon 61 mutational hot spots Cancer Res 2000, 60:1849-1856. 10766171
3. Hankinson O The aryl hydrocarbon receptor complex Ann Rev Pharmacol Toxicol 1995, 35:307-340. 10.1146/annurev.pa.35.040195.001515
4. Conney AH Induction of microsomal enzymes by foreign chemicals and carcinogenesis by polycyclic aromatic hydrocarbons: GHA. Clowes memorial lecture Cancer Res 1982, 4:4875-4917.
5. Guengerich FP Shimada T Oxidation of toxic and carcinogenic chemicals by human cytochrome P450 enzymes Chem Res Toxicol 1991, 4:391-407. 10.1021/ tx00022a001 1912325
6. Shimada T Fujii-Kuriyama Y Metabolic activation of polycyclic aromatic hydrocarbons to carcinogens by cytochromes P450 1A1 and 1B1 Cancer Sci 2004, 95:1-6. 10.1111/j.1349-7006.2004.tb03162.x 14720319
7. Tang M-shong Vulimiri SV Viaje A Chen JX Bilolikar DS Morris RJ Harvey RG Slaga TJ DiGiovanni J Both (±) syn- and (±) anti-7,12-dimethylbenz[a]anthracene-3,4-diol-1,2-epoxides initiate tumors in mouse skin that possess-CAA- to CTA- mutations at codon 61 of c-H-ras Cancer Res 2000, 60:5688-5695. 11059761
8. Shimada T Oda Y Gillam EMJ Guengerich FP Inoue K Metabolic activation of polycyclic aromatic hydrocarbons and other procarcinogens by cytochromes P450 1A1 and P450 1B1 allelic variants and other human cytochromes P450 in Salmonella typhimurium NM2009 Drug Metab Dispos 2001, 29:1176-1182. 11502724
9. Shimada T Inoue K Suzuki Y Kawai T Azuma E Nakajima T Shindo M Kurose K Sugie A Yamagishi Y Fujii-Kuriyama Y Hashimoto M Arylhydrocarbon receptor-dependent induction of liver and lung cytochromes P450 1A1,1A2 and 1B1 by polycyclic aromatic hydrocarbons and polychlorinated biphenyls in genetically engineered C57BL/6J mice Carcinogenesis 2002, 23:1199-1207. 10.1093/carcin/23.7.1199 12117779
10. Shimizu Y Nakatsura Y Ichinose M Takahashi Y Kume H Mimura J Fujii-Kuriyama Y Ishikawa T Benzo[a]pyrene carcinogenicity is lost in mice lacking the aryl hydrocarbon receptor Proc Natl Acad Sci USA 2000, 97:779-782. 15407 10639156 10.1073/pnas.97.2.779
11. Shimada T Hayes CL Yamazaki H Amin S Hecht SS Guengerich FP Sutter TR Activation of chemically diverse procarcinogens by human cytochrome P450 1B1 Cancer Res 1996, 56:2979-2984. 8674051
12. Luch A Schober W Soballa VJ Raub G Greim H Jacob J Doehner J Seidel A Metabolic activation of dibenzo[a, l]pyrene by human cytochrome P450 1A1 and 1B1 expressed in V79 Chinese hamster cells Chem Res Toxicol 1999, 12:353-364. 10.1021/tx980240g 10207125
13. Ma X Idle JR Malfatti MA Krausz KW Nebert DW Chen C Felton JS Waxman DJ Gonzalez FJ Mouse lung CYP1A1 catalyzes the metabolic activation of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) Carcinogenesis 2007, 28:732-737. 1829392 17052995 10.1093/carcin/bgl184
14. Cheung C Ma X Krausz KW Kimura S Feigenbaum L Dalton TP Nebert DW Idle JR Gonzalez FJ Differential metabolism of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in mice humanized for CYP1A1 and CYP1A2 Chem Res Toxicol 2005, 18:1471-1478. 10.1021/ tx050136g 16167840
15. Friesen MD Kaderlik K Lin D Garren L Bartsch H Lang NP Kadlubar FF Analysis of DNA adducts of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in rat and human tissues by alkaline hydrolysis and gas chromatography/electron capture mass spectrometry: Validation by comparison with 32P-postlabeling Chem Res Toxicol 1994, 7:733-739. 10.1021/tx00042a004 7696526
16. Snyderwine EG Yu M Schut HA Knight-Jones L Kimura S Effect of CYP1A2 deficiency on heterocyclic amino DNA adduct levels in mice Food Chem Toxicol 2002, 40:1529-1533. 10.1016/S0278-6915(02)00110-2 12387319
17. Cheung C Ma X Krausz KW Kimura S Feigenbaum L Dalton TP Nebert DW Idle Fujita K Kamataki T Predicting the mutagenicity of tobacco-related N-nitrosamines in humans using 11 strains of Salmonella typhimurium YG7108, each coexpressing a form of human cytochrome P450 along with NADPH-cytochrome P450 reductase Environ Mol Mutagenesis 2001, 38:339-346. 10.1002/em.10036
18. Fujita K Kamataki T Role of human cytochrome P450 (CYP) in the metabolic activation of N-alkylnitrosamines: Application of genetically engineered Salmonella typhimurium YG7108 expressing each form of CYP together with human NADPH-cytochrome P450 reductase Mutation Res 2001 483 35 41 11600130
19. Puga A Ma C Marlowe JL The aryl hydrocarbon receptor cross-talks with multiple signal transduction pathways Biochem Pharmacol 2009, 77:713-722. 10.1016/j.bcp.2008.08.031 18817753
20. Hankinson O Role of coactivators in transcriptional activation by the aryl hydrocarbon receptor Arch Biochem Biophys 2005, 433:379-386. 10.1016/j.abb.2004.09.031 15581594
21. Mimura J Fujii-Kuriyama Y Functional role of AhR in the expression of toxic effects by TCDD Biochim Biophys Acta 2003, 1619:263-268. 12573486
22. Fujii-Kuriyama Y Mimura J Molecular mechanisms of AhR functions in the regulation of cytochrome P450 genes Biochem Biophys Res Commun 2005, 338:311-317. 10.1016/j.bbrc.2005.08.162 16153594
23. Wang S Ge K Roeder RG Hankinson O Role of mediator in transcriptional activation by the aryl hydrocarbon receptor J Biol Chem 2004, 279:13593-13600. 10.1074/jbc.M312274200 14729673
24. Wei YD Tepperman K Huang MY Sartor MA Puga A Chromium inhibits transcription from polycyclic aromatic hydrocarbon-inducible promoters by blocking the release of histone deacetylase and preventing the binding of p300 to chromatin J Biol Chem 2004, 279:4110-4119. 10.1074/ jbc.M310800200 14625279
25. Kung T Murphy KA White LA The aryl hydrocarbon receptor (AhR) pathway as a regulatory pathway for cell adhesion and matrix metabolism Biochem Pharmacol 2009, 77:536-546. 10.1016/j.bcp.2008.09.031 18940186
26. Chan WK Yao G Gu YZ Bradfield CA Cross-talk between the aryl hydrocarbon receptor and hypoxia inducible factor signaling pathways J Biol Chem 1999, 274:12115-12123. 10.1074/jbc.274.17.12115 10207038
27. Carrier F Owens RA Nebert DW Puga A Dioxin-dependent activation of murine Cyp1a-1 gene transcription requires protein kinase C-dependent phosphorylation Mol Cell Biol 1992, 12:1856-1863. 369629 1312672
28. Ikegwuonu FI Christou M Jefcoate CR Regulation of cytochrome P4501B1 (CYP1B1) in mouse embryo fibroblast (C3H10T1/2) cells by protein kinase C (PKC) Biochem Pharmacol 1999, 57:619-630. 10.1016/ S0006-2952(98)00344-X 10037446
29. Ikuta T Kobayashi Y Kawajiri K Phosphorylation of nuclear localization signal inhibits the ligand-dependent nuclear import of aryl hydrocarbon receptor Biochem Biophys Res Commun 2004, 317:545-550. 10.1016/ j.bbrc.2004.03.076 15063792
30. Ikuta T Kobayashi Y Kawajiri K Cell density regulates intracellular localization of aryl hydrocarbon receptor J Biol Chem 2004, 279:19209-19216. 10.1074/jbc.M310492200 14985336
31. Diry M Tomkiewicz C Koehle C Coumoul X Bock KW Barouki R Transy C Activation of the dioxin/aryl hydrocarbon receptor (AhR) modulates cell plasticity through a JNK-dependent mechanism Oncogene 2006, 25:5570-5574. 10.1038/sj.onc.1209553 16619036
32. Tan Z Huang M Puga A Xia Y A critical role for MAP kinases in the control of Ah receptor complex activity Toxicol Sci 2004, 82:80-87. 10.1093/toxsci/kfh228 15272135
33. Tan Z Huang M Puga A Xia Y Activation of mitogen-activated protein kinases (MAPKs) by aromatic hydrocarbons: Role in the regulation of aryl hydrocarbon receptor (AHR) function Biochem Pharmacol 2002, 64:771-780. 10.1016/S0006-2952(02)01138-3 12213569
34. Henklová P Vrzal R Ulrichová J Dvoøák Z Role of mitogen-activated protein kinases in aryl hydrocarbon receptor signaling Chem-Biol Interact 2008, 172:93-104. 10.1016/j.cbi.2007.12.005 18282562
35. Chen S Operama T Bonzo J Nguyen N Tukey RH ERK kinase inhibition stabilizes the aryl hydrocarbon receptor: Implications for transcriptional activation and protein degradation J Biol Chem 2005, 280:4350-4359. 10.1074/jbc.M411554200 15572374
36. Ma Q Whitlock JPJ The aromatic hydrocarbon receptor modulates the Hepa 1c1c7 cell cycle and differentiated state independently of dioxin Mol Cell Biol 1996, 16:2144-2150 231202 8628281
37. Elizondo G Fernandez-Salguero P Sheikh MS Kim GY Fornace AJ Lee KS Gonzalez FJ Altered cell cycle control at the G(2)/M phases in aryl hydrocarbon receptor-null embryo fibroblast Mol Pharmacol 2000, 57:1056-1063 10779392
38. Gierthy JF Crane D Reversible inhibition of in vitro epithelial cell proliferation by 2,3,7,8-tetrachlorodibenzo-p-dioxin Toxicol Appl Pharmacol 1984, 74:91-98 10.1016/0041-008X(84)90274-6 6729824
39. Huska DR Greenlee WF 2,3,7,8-Tetrachlorodibenzo-p-dioxin inhibits DNA synthesis in rat primary hepatocytes Mutat Res 1995, 333:89-99 8538640
40. Bauman JW Goldsworthy TL Dunn CS Fox TR Inhibitory effects of 2,3,7,8-tetrachlorodibenzo-p-dioxin on rat hepatocyte proliferation induced by 2/3 partial hepatectomy Cell Prolif 1995, 28:437-451 10.1111/ j.1365-2184.1995.tb00084.x 7548444
41. Wang W Smith IR Safe S Aryl hydrocarbon receptor-mediated antiestrogenicity in MCF-7 cells: Modulation of hormone-induced cell cycle enzymes Arch Biochem Biophys 1998, 356:239-248 10.1006/ abbi.1998.0782 9705214
42. Hestermann EV Stegeman JJ Hahn ME Relationships among the cell cycle, cell proliferation, and aryl hydrocarbon receptor expression in PLHC-1 cells Aquat Toxicol 2002, 58:201-213 10.1016/S0166-445X(01)00229-6 12007875
43. Barnes-Ellerbe S Knudsen KE Puga A 2,3,7,8-Tetrachlorodibenzo-p-dioxin blocks androgen-dependent cell proliferation of LNCaP cells through modulation of pRB phosphorylation Mol Pharmacol 2004, 66:502-511 10.1124/ mol.104.000356 15322241
44. Levine-Fridman A Chen L Elferink CJ Cytochrome P4501A1 promotes G1 phase cell cycle progression by controlling aryl hydrocarbon receptor activity Mol Pharmacol 2004, 65:461-469 10.1124/mol.65.2.461 14742689
45. Marlowe JL Puga A Aryl hydrocarbon receptor, cell cycle regulation, toxicity and tumorigenesis J Cell Biochem 2005, 96:1174-84 10.1002/ jcb.20656 16211578
46. Ge N-L Elferink CJ A direct interaction between the aryl hydrocarbon receptor and retinoblastoma protein J Biol Chem 1998, 273:22708-22713 10.1074/jbc.273.35.22708 9712901
47. Chan HM Smith L La Thangue NB Role of LXCXE motif-dependent interactions in the activity of the retinoblastoma protein Oncogene 2001, 20:6152-6163 10.1038/sj.onc.1204793 11593423
48. Puga A Barnes SJ Dalton TP Chang C Knudsen ES Maier MA Aromatic hydrocarbon receptor interaction with the retinoblastoma protein potentiates repression of E2F-dependent transcription and cell cycle arrest J Biol Chem 2000, 275:2943-2950 10.1074/jbc.275.4.2943 10644764
49. Chang X Fan Y Karyala S Schwemberger S Tomlinson CR Sartor MA Puga A Ligand-independent regulation of transforming growth factor β1 expression and cell cycle progression by the aryl hydrocarbon receptor Mol Cell Biol 2007, 27:6127-6139 1952156 17606626 10.1128/MCB.00323-07
50. Yang X Solomon S Fraser LR Trombino AF Liu D Sonenshein GE Hestermann EV Sherr DH Constitutive regulation of CYP1B1 by the aryl hydrocarbon receptor (AhR) in pre-malignant and malignant mammary tissue J Cell Biochem 2008, 104:402-417 10.1002/jcb.21630 18059014
51. Monostory K Kohalmy K Prough RA Kobori L Vereczkey L The effect of synthetic glucocorticoid, dexamethasone on CYP1A1 inducibility in adult rat and human hepatocytes FEBS Lett 2005, 579:229-235 10.1016/ j.febslet.2004.11.080 15620718
52. Bielefeld KA Lee C Riddick DS Regulation of aryl hydrocarbon receptor expression and function by glucocorticoids in mouse hepatoma cells Drug Metab Dispos 2008, 36:543-551 10.1124/dmd.107.019703 18086832
53. Prough RA Linder MW Pinaire JA Xiao GH Falkner KC Hormonal regulation of hepatic enzymes involved in foreign compound metabolism Faseb J 1996, 10:1369-1377 8903507
54. Lai KP Wong MH Wong CK Modulation of AhR-mediated CYP1A1 mRNA and EROD activities by 17beta-estradiol and dexamethasone in TCDD-induced H411E cells Toxicol Sci 2004, 78:41-49 10.1093/toxsci/kfh045 14691211
55. Celander M Hahn ME Steceman JJ Cytochromes P450 (CYP) in the Poeciliopsis lucida hepatocellular carcinoma cell line (PLHC-1): Dose- and time- dependent glucocorticoid potentiation of CYP1A induction without induction of CYP3A Arch Biochem Biophys 1996, 329:113-122 10.1006/abbi.1996.0198 8619627
56. Dvoøak Z Vrzal R Pávek P Ulrichová J An evidence for regulatory cross-talk between aryl hydrocarbon receptor and glucocorticoid receptor in HepG2 cells Physiol Res 2008, 57:427-435 17552871
57. Vrzal R Stejskalova L Monostory K Maurel P Bachleda P Pavek P Dvorak Z Dexamethasone controls aryl hydrocarbon receptor (AhR)-mediated CYP1A1 and CYP1A2 expression and activity in primary cultures of human hepatocytes Chem Biol Interact 2009, 179:288-296 10.1016/ j.cbi.2008.10.035 19022236
58. Pearce ST Liu H Radhakrishnan I Abdelrahim M Safe S Jordan VC Interaction of the aryl hydrocarbon receptor ligand 6-methyl-1,3,8-thrichlorodibenzofuran with oestrogen receptor alpha Cancer Res 2004, 64:2889-2897 10.1158/0008-5472.CAN-03-1770 15087408
59. Safe S Wormke M Inhibitory aryl hydrocarbon receptor-estrogen receptor alpha cross-talk and mechanisms of action Chem Res Toxicol 2003, 16:807-816 10.1021/tx034036r 12870882
60. Matthews J Wihlén B Thomsen J Gustafsson J Aryl hydrocarbon receptor-mediated transcription: Ligand-dependent recruitment of estrogen receptor α to 2,3,7,8-tetrachlorodibenzo-p-dioxin-responsive promoters Mol Cell Biol 2005, 25:5317-5328 1156992 15964790 10.1128/MCB.25.13.5317-5328.2005
61. Sarkar S Jana NR Yonemoto J Tohyama C Sone H Estrogen enhances induction of cytochrome P-4501A1 by 2,3,7,8-tetrachlorodibenzo-p-dioxin in liver of female Long-Evans rats Int J Oncol 2000, 16:141-147 10601559
62. Han W Pentecost BT Pietropaolo RL Fasco MJ Spivack SD Estrogen receptor α increases basal and cigarette smoke extract-induced expression of CYP1A1 and CYP1B1, but not GSTP1 in normal human bronchial epithelial cells Mol Carcinogenesis 2005, 44:202-211 10.1002/mc.20128
63. Ohtake F Takeyama K Matsumoto H Kitagawa H Yamamoto Y Nohara K Tohyama C Krust A Mimura J Chambon P Yanagisawa J Fujii-Kuriyama Y Kato S Modulation of oestrogen receptor signaling by association with the activated dioxin receptor Nature 2003, 423:545-550 10.1038/nature01606 12774124
64. Schmidt JV Bradfield CA AH receptor signaling pathways Ann Rev Cell Dev Biol 1996, 12:55-89 10.1146/annurev.cellbio.12.1.55
65. Blancher C Harris AL The molecular basis of the hypoxia response pathway: Tumor hypoxia as a therapy target Cancer and Metastasis Rev 1998, 17:187-194 10.1023/A:1006002419244
66. Wood SM Gleadle JM Pugh CW Hankinson O Ratcliffe PJ The role of the aryl hydrocarbon receptor nuclear translocator (ARNT) in hypoxic induction of gene expression-Studies in ARNT deficient cells J Biol Chem 1996, 271:15117-15123 10.1074/jbc.271.48.30392 8662957
67. Chan WK Yao G Gu YZ Bradfield CA Cross-talk between the aryl hydrocarbon receptor and hypoxia inducible factor signaling pathways J Biol Chem 1999, 274:12115-12123 10.1074/jbc.274.17.12115 10207038
68. Zhang N Walker MK Crosstalk between the aryl hydrocarbon receptor and hypoxia on the constitutive expression of cytochrome P4501A1 mRNA Cardiovasc Toxicol 2007, 7:282-290 2213366 17968679 10.1007/ s12012-007-9007-6
69. Frericks M Burgoon LD Zacharewski TR Esser C Promoter analysis of TCDD-inducible genes in a thymic epithelial cell line indicates the potential for cell-specific transcription factor crosstalk in the AhR response Toxicol Appl Pharmacol 2008, 232:268-279 10.1016/ j.taap.2008.07.009 18691609
70. Bhakta KY Jiang W Couroucli XI Fazili IS Muthiah K Moorthy B Regulation of cytochrome P4501A1 expression by hyperoxia in human lung cell lines Toxicol Appl Pharmacol 2008, 233:169-178 10.1016/j.taap.2008.08.016 18824009
71. Bernauer U Heinrich-Hirsch B Tönnies M Peter-Matthias W Gundert-Remy U Characterisation of the xenobiotic-metabolizing cytochrome P450 expression pattern in human lung tissue by immunochemical and activity determination Toxicol Lett 2006, 164:278-288 10.1016/j.toxlet.2006.01.007 16483733
72. Wei C Caccavale RJ Weyand EH Chen S Iba MM Induction of CYP1A1 and CYP1A2 expressions by prototypic and atypical inducers in the human lung Cancer Lett 2002, 178:25-36 10.1016/S0304-3835(01)00809-6 11849738
73. Wei C Caccavale RJ Kehce JJ Thomas PE Iba MM CYP1A2 is expressed along with CYP1A1 in the human lung Cancer Lett 2001, 171:113-120 10.1016/ S0304-3835(01)00529-8 11485833
74. Chang TJ Chang H Chen P Lin S Lin P Requirement of aryl hydrocarbon receptor overexpression for CYP1B1 up-regulation and cell growth in human lung adenocarcinomas Clin Cancer Res 2007, 13:38-45 10.1158/ 1078-0432.CCR-06-1166 17200336
75. Anttila S Hakkola J Tuominen P Elovaara E Husgafvel-Pusiainen K Karjalainen A Hirvonen A Nurminen T Methylation of cytochrome P4501A1 promoter in the lung is associated with tobacco smoking Cancer Res 2003, 63:8623-8628 14695173
76. Oyama T Sugio K Uramoto H Iwata T Onitsuka T Isse T Nozoe T Kagawa N Yasumoto K Kawamoto T Increased cytochrome P450 and aryl hydrocarbon receptor in bronchial epithelium of heavy smokers with non-small cell lung carcinoma carries a poor prognosis Front Biosci 2007, 12:4497-4503 10.2741/2404 17485391
77. Oyama T Sugio K Uramoto H Kawamoto T Kagawa N Nadaf S Carbone D Yasumoto K Cytochrome P450 expression (CYP) in non-small cell lung cancer Front 2007, 12:2299-2308 10.2741/2232
78. Murray GI Taylor MC McFadyen MC McKay JA Greenlee WF Burke MD Melvin WT Tumor specific expression of Cytochrome P450 CYP1B1 Cancer Res 1997, 57:3026-3031 9230218
79. McKay JA Melvin WT Ah-See AK Ewen SW Greenlee WF Marcus CB Burke MD Murray GI Expression of cytochrome P450 CYP1B1 in breast cancer FEBS Lett 1995, 374:270-272 10.1016/0014-5793(95)01126-Y 7589551
80. McKay JA Murray GI Ah-See AK Greenlee WF Marcus CB Burke MD Melvin WT Differential expression of CYP1A1 and CYP1B1 in human breast cancer Biochem Soc Trans 1996, 24:327S 8736985
81. Goth-Goldstein R Stampfer MR Erdmann CA Russell M Interindividual variation in CYP1A1 expression in breast tissue and the role of genetic polymorphism Carcinogenesis 2000, 21:2119-2122 10.1093/carcin/21.11.2119 11062177
82. Liehr JG Ricci MJ 4-Hydroxylation of estrogens as marker of human mammary tumors Proc Nat Acad Sci USA 1996, 93:3294-3296 39600 8622931 10.1073/pnas.93.8.3294
83. Murray GI Shaw D Weaver RJ McKay JA Ewen SW Melvin WT Burke MD Cytochrome P450 expression in oesophageal cancer Gut 1994, 35:599-603 1374739 8200549 10.1136/gut.35.5.599
84. Murray GI Taylor VE McKay JA Weaver RJ Ewen SW Melvin WT Burke MD Expression of xenobiotic metabolizing enzymes in tumors of the urinary bladder Int J Exp Pathol 1995, 76:271-276 7547441
85. Syme MR Paxton JW Keelan JA Drug transfer and metabolism by the human placenta Clin Pharmacokinet 2004, 43:487-514 10.2165/ 00003088-200443080-00001 15170365
86. Myllynen P Pasanen M Vähäkangas K The fate and effects of xenobiotics in human placenta Expert Opin Drug Metab Toxicol 2007, 3:331-346 10.1517/17425255.3.3.331 17539742
87. Pavek P Dvorak Z Xenobiotic-induced transcriptional regulation of xenobiotic metabolizing enzymes of the cytochrome P450 superfamily in human extrahepatic tissues Curr Drug Metab 2008, 9:29-143 10.2174/ 138920008783571774 18288955
88. Avery ML Meek CE Audus KL The presence of inducible cytochrome P450 types 1A1 and 1A2 in the BeWo cell line Placenta 2003, 24:45-52 10.1053/ plac.2002.0876 12495659
89. Kolwankar D Glover DD Ware JA Tracy TS Expression and function of ABCB1 and ABCG2 in human placental tissue Drug Metab Dispos 2005, 33:524-529 10.1124/dmd.104.002261 15640379
90. Hakkola J Pasanen M Pelkonen O Hukkanen J Evisalmi S Anttila S Rane A Mäntylä M Purkunen R Saarikoski S Tooming M Raunio H Expression of CYP1B1 in human adult and fetal tissues and differential inducibility of CYP1B1 and CYP1A1 by Ah receptor ligands in human placenta and cultured cells Carcinogenesis 1997, 18:391-397 10.1093/ carcin/18.2.391 9054634
91. Walle T Absorption and metabolism of flavonoids Free Radic Biol Med 2004, 36:829-837 10.1016/j.freeradbiomed.2004.01.002 15019968
92. Paine MF Hart HL Ludington SS Haining RL Rettie AE Zeldin DC The human intestinal cytochrome P450 "pie" Drug Metab Dispos 2006, 34:880-886 2222892 16467132 10.1124/dmd.105.008672
93. McDonnell WM Scheiman JM Traber PG Induction of cytochrome P450IA genes (CYP1A) by omeprazole in the human alimentary tract Gastroenterology 1992, 103:1509-1516 1426869
94. Eskin SG Turner NA McIntire LV Endothelial cell cytochrome P450 1A1 and 1B1: Up-regulation by shear stress Endothelium 2004, 11:1-10 10.1080/ 10623320490432434 15203874
95. Conway DE Sakurai Y Weiss D Vega JD Taylor WR Jo H Eskin SG Marcus CB McIntire LV Expression of CYP1A1 and CYP1B1 in human endothelial cells: regulation by fluid shear stress Cardiovasc Res 2009, 81:669-677 10.1093/ cvr/cvn360 19126602
96. Bale AE Nebert DW McBride OW Subchromosomal localization of the dioxin-inducible P1450 locus (CYP1) and description of two RFLPs detected within a 3' P1450 cDNA probe Cytogenet Cell Genet 1987, 46:574-575
97. Hayashi S Watanabe J Nakachi K Kawajiri K Genetic linkage of lung cancer-associated MspI polymorphisms with amino acid replacement in the heme binding region of the human cytochrome P4501A1 gene J Biochem 1991, 110:407-411 1722803
98. Tabor HK Risch NJ Myers RM Opinion: Candidate-gene approaches for studying complex genetic traits: Practical considerations Nat Rev Genet 2002, 3:391-397 10.1038/nrg796 11988764
99. Crofts F Taioli E Trachman J Cosma GN Currie D Toniolo P Garte SJ Functional significance of different human CYP1A1 genotypes Carcinogenesis 1994, 15:2961-2963 10.1093/carcin/15.12.2961 8001264
100. Zhang ZY Fasco MJ Huang L Guengerich FP Kaminsky LS Characterization of purified human recombinant cytochrome P4501A1-Ile462 and -Val462: assessment of a role for the rare allele in carcinogenesis Cancer Res 1996, 87:18-24
101. Cosma G Crofts F Taioli E Toniolo P Carte S Relationship between genotype and function of the human CYP1A1 gene J Toxicol Environ Health 1993, 40:309-316 7901425
102. Kiyohara C Hirohata T Inutsuka S The relationship between aryl hydrocarbon hydroxylase and polymorphisms of the CYP1A1 gene Jpn J Cancer Res 1996, 87:18-24 8609043
103. Daly AK Fairbrother KS Smart J Recent advances in understanding the molecular basis of polymorphisms in genes encoding cytochrome P450 enzymes Toxicol Lett 1998, 102-103:143-147 10.1016/S0378-4274(98)00299-9
104. Smart J Daly AK Variation in induced CYP1A1 levels: Relationship to CYP1A1, Ah receptor and GSTM1 polymorphisms Pharmacogenetics 2000, 10:11-24 10.1097/00008571-200002000-00003 10739168
105. Nakachi K Imai K Hayashi S Kawajiri K Polymorphisms of the CYP1A1 and glutathione S-transferase genes associated with susceptibility to lung cancer in relation to cigarette dose in a Japanese population Cancer Res 1993, 53:2994-2999 8319207
106. Kelsey KT Wiencke JK Spitz MR A race-specific genetic polymorphism in the CYP1A1 gene is not associated with lung cancer in African Americans Carcinogenesis 1994, 15:1121-1124 10.1093/carcin/15.6.1121 8020143
107. Niranjan BG Avadhani NG DiGiovanni J Formation of benzo[a]pyrene metabolites and DNA adducts catalyzed by a rat liver mitochondrial monooxygenase system Biochem Biophys Res Commun 1985, 131:935-942 10.1016/0006-291X(85)91329-4 2996532
108. Raza H Avadhani NG Hepatic mitochondrial cytochrome P-450 system. Purification and characterization of two distinct forms of mitochondrial cytochrome P-450 from b-naphthoflavone-induced rat liver J Biol Chem 1988, 263:9533-9541 2837492
109. Anandatheerthavarada HK Vijayasarathy C Bhagwat SV Biswas G Mullick J Avadhani NG Physiological role of the N-terminal processed P450 1A1 targeted to mitochondria in erythromycin metabolism and reversal of erythromycin-mediated inhibition of mitochondrial protein synthesis J Biol Chem 1999, 274:6617-6625 10.1074/jbc.274.10.6617 10037757
110. Dong H Dalton TP Miller ML Chen Y Uno S Shi Z Shertzer HG Bansal S Avadhani NG Nebert DW Knock-in mouse lines expressing either mitochondrial or microsomal CYP1A1: Differing responses to dietary benzo[a]pyrene as proof of principle Mol Pharmacol 2009, 75:555-567 10.1124/mol.108.051888 19047483
111. Uno S Dalton TP Derkenne S Curran CP Miller ML Shertzer HG Nebert DW Oral exposure to benzo[a]pyrene in the mouse: Detoxication by inducible cytochrome P450 is more important than metabolic activation Mol Pharmacol 2004, 65:1225-1237 10.1124/mol.65.5.1225 15102951
112. Uno S Dalton TP Dragin N Curran CP Derkenne S Miller ML Shertzer HG Gonzalez FJ Nebert DW Oral benzo[a]pyrene in Cyp1 knockout mouse lines: CYP1A1 important in detoxication, CYP1B1 metabolism required for immune damage independent of total-body burden and clearance rate Mol Pharmacol 2006, 69:1103-1114 10.1124/mol.105.021501 16377763
113. Dragin N Shi Z Madan R Karp CL Sartor MA Chen C Gonzalez FJ Nebert DW Phenotype of the Cyp1a1/1a2/1b1(-/-) triple-knockout mouse Mol Pharmacol 2008, 73:1844-1856 10.1124/mol.108.045658 18372398
114. Dragin N Uno S Wang B Dalton TP Nebert DW Generation of 'humanized' CYP1A1_1A2_Cyp1a1/1a2(-/-) mouse line Biochem Biophys Res Commun 2007, 359:635-642 1994648 17560947 10.1016/j.bbrc.2007.05.202
115. Chiaro CR Patel RD Marcus CB Perdew GH Evidence for an aryl hydrocarbon receptor-mediated cytochrome P450 autoregulatory pathway Mol Pharmacol 2007, 72:1369-1379 10.1124/mol.107.038968 17720764
116. Chua MS Kashiyama E Bradshaw TD Stinson SF Brantley E Sausville EA Stevens MFG Role of CYP1A1 in modulation of antitumor properties of the novel agent 2-(4-amino-3-methylphenyl)benzothiazole (DF 203, NSC 674495) in human breast cancer cells Cancer Res 2000, 60:5196-5203 11016648
117. Brantley E Trapani V Alley MC Hose CD Bradshaw TD Stevens MGF Sausville EA Stinson SF Fluorinated 2-(4-amino-3-methylphenyl)benzothiazoles induce CYP1A1 expression, become metabolized, and bind to macromolecules in sensitive human cancer cells Drug Metab Dispos 2004, 32:1392-1401 10.1124/dmd.104.001057 15355884
118. Bradshaw TD Westwell AD The development of the antitumor benzothiazole prodrug, Phortress as a clinical candidate Curr Med Chem 2004, 11:1009-1021 10.2174/0929867043455530 15078163
119. Trapani V Patel V Leong CO Ciolino HP Yeh GC Hose C Trepel JB Stevens MF Sausville EA Loaiza-Pérez AI DNA damage and cell cycle arrest induced by 2-(4-amino-3-methylphenyl)-5-fluorobenzothiazole (5F 203, NSC 703786) is attenuated in aryl hydrocarbon receptor deficient MCF-7 cells Br J Cancer 2003, 88:599-605 10.1038/sj.bjc.6600722 12592376
120. Loaiza-Pérez AI Kenney S Boswell J Hollingshead M Alley MC Hose C Ciolino HP Yeh GC Trepel JB Vistica DT Sausville EA Aryl hydrocarbon receptor activation of an antitumor aminoflavone: Basis of selective toxicity for MCF-7 breast tumor cells Mol Cancer Ther 2004, 3:715-725 15210858
121. Meng LH Shankavaram U Chen C Agama K Fu HQ Gonzalez FJ Weinstein J Pommier Y Activation of aminoflavone (NSC 686288) by a sulfotransferase is required for the antiproliferative effect of the drug and for induction of histone gamma-H2AX Cancer Res 2006, 66:9656-9664 10.1158/ 0008-5472.CAN-06-0796 17018623
122. Androutsopoulos V Arroo RRJ Hall JF Surichan S Potter GA Antiproliferative and cytostatic effects of the natural product eupatorin due to CYP1 mediated metabolism Breast Cancer Res 2008, 10:R39 2481486 18454852 10.1186/bcr2090
123. Atherton K Mutch E Ford D Metabolism of the soyabean isoflavone daidzein by CYP1A2 and the extra-hepatic CYPs 1A1 and 1B1 affects biological activity Biochem Pharmacol 2006, 72:624-31 10.1016/j.bcp.2006.05.015 16814747
124. Androutsopoulos V Wilsher N Arroo RRJ Potter GA Bioactivation of the phytoestrogen diosmetin by CYP1 cytochromes P450 Cancer Lett 2009, 274:54-60 10.1016/j.canlet.2008.08.032 18976853
125. Androutsopoulos VP Mahale S Arroo RRJ Potter G Anticancer effects of the flavonoid diosmetin on cell cycle progression and proliferation of MDA-MB 468 breast cancer cells due to CYP1 activation Oncol Rep 2009, 21:1525-1528 19424633
126. Walle UK Walle T Cytochrome P450-mediated metabolism of methoxyflavones Drug Metab Dispos 2007, 35:1985-1989 10.1124/dmd.107.016782 17709371
127. Otake Y Walle T Oxidation of the flavonoids galangin and kaempferide by human liver microsomes and CYP1A1, CYP1A2 and CYP2C9 Drug Metab Dispos 2002, 30:103-105 10.1124/dmd.30.2.103 11792676
128. Somerset SM Johannot L Dietary flavonoids sources in Australian adults Nutr Cancer 2008, 60:442-449 10.1080/01635580802143836 18584477
129. Ciolino HP Wang TTY Yeh GC Diosmin and diosmetin are agonists of the aryl hydrocarbon receptor that differentially affect cytochrome P450 1A1 activity Cancer Res 1998, 58:2754-2760 9661887
130. Ciolino HP Daschner PJ Yeh GC Dietary flavonols quercetin and kaempferol are ligands of the aryl hydrocarbon receptor that affect CYP1A1 transcription differentially Biochem J 1999, 340:715-722 1220303 10359656 10.1042/0264-6021:3400715
131. Ciolino HP Yeh GC The flavonoid galangin is an inhibitor of CYP1A1 activity and an agonist/antagonist of the aryl hydrocarbon receptor Br J Cancer 1999, 79:1340-1346 10.1038/sj.bjc.6690216 10188874
132. Ciolino HP Yeh GC Inhibition of aryl hydrocarbon-induced cytochrome P-450 1A1 enzyme activity and CYP1A1 expression by resveratrol Mol Pharmacol 1999, 56:760-767 10496959
133. Denison MS Nagy SR Activation of the aryl hydrocarbon receptor by structurally diverse exogenous and endogenous chemicals Ann Rev Pharmacol Toxicol 2003, 43:309-334 10.1146/ annurev.pharmtox.43.100901.135828
134. Arroo RRJ Androutsopoulos V Patel A Surichan S Wilsher N Potter GA Phytoestrogens as natural prodrugs in cancer prevention: A novel concept Phytochem Rev 2008, 431:443 10.1007/s11101-008-9093-5
135. Gonzalez FJ Gelboin HV Role of human cytochromes P450 in the metabolic activation of chemical carcinogens and toxins Drug Metab Rev 1994, 26:165-183. 10.3109/03602539409029789 8082563