Metabolism of the EGFR tyrosin kinase inhibitor gefitinib by cytochrome P450 1A1 enzyme in EGFR-wild type non small cell lung cancer cell lines

Molecular Cancer

Volumn 10, Issue , 2011, Pages

  Alfieri, Roberta R ^a   Galetti, Maricla ^a   Tramonti, Stefano ^a   Andreoli, Roberta ^a   Mozzoni, Paola ^a   Cavazzoni, Andrea ^a   Bonelli, Mara ^a   Fumarola, Claudia ^a   La Monica, Silvia ^a   Galvani, Elena ^a   De Palma, Giuseppe ^b   Mutti, Antonio ^a   Mor, Marco ^a   Tiseo, Marcello ^c   Mari, Ettore ^d   Ardizzoni, Andrea ^d   Petronini, Pier G ^a  

^a UNIVERSITY OF PARMA   (Italy)

^b UNIVERSITY OF BRESCIA   (Italy)

^c UNIVERSITY HOSPITAL OF PARMA   (Italy)

^d ASTRAZENECA   (United Kingdom)

Author keywords

CYP1A1; EGFR; Gefitinib; Lung cancer; Metabolism

Indexed keywords

1 (1 CYANO 1 METHYLETHYL) 3 METHYL 8 (3 QUINOLINYL)IMIDAZO[4,5 C]QUINOLIN 2(1H,3H) ONE; 1,4 DIAMINO 1,4 BIS(2 AMINOPHENYLTHIO) 2,3 DICYANOBUTADIENE; 2 (2 AMINO 3 METHOXYPHENYL)CHROMONE; ALPHA NAPHTHOFLAVONE; CETUXIMAB; CIGARETTE SMOKE; CYTOCHROME P450 1A1; DRUG METABOLITE; EPIDERMAL GROWTH FACTOR RECEPTOR; ERLOTINIB; ETHOXYRESORUFIN DEETHYLASE; EVEROLIMUS; GEFITINIB; LAPATINIB; MAMMALIAN TARGET OF RAPAMYCIN; MESSENGER RNA; MITOGEN ACTIVATED PROTEIN KINASE; PHOSPHATIDYLINOSITOL 3 KINASE; PROTEIN KINASE B; WORTMANNIN;

ANTINEOPLASTIC ACTIVITY; ARTICLE; AUTOPHOSPHORYLATION; CANCER CELL CULTURE; CANCER RESISTANCE; CELL DENSITY; CELL HYPOXIA; CELL LEVEL; CELL METABOLISM; CELL PROLIFERATION; CONTROLLED STUDY; DRUG EFFICACY; DRUG METABOLISM; ENZYME ACTIVITY; ENZYME ASSAY; ENZYME INHIBITION; HUMAN; HUMAN CELL; LUNG NON SMALL CELL CANCER; REVERSE TRANSCRIPTION POLYMERASE CHAIN REACTION; SIGNAL TRANSDUCTION; TREATMENT RESPONSE; WILD TYPE;

ANTINEOPLASTIC AGENTS; CARCINOMA, NON-SMALL-CELL LUNG; CELL LINE, TUMOR; CYTOCHROME P-450 CYP1A1; DRUG RESISTANCE, NEOPLASM; HUMANS; LUNG NEOPLASMS; MUTATION; PHOSPHORYLATION; QUINAZOLINES; RECEPTOR, EPIDERMAL GROWTH FACTOR;

EID: 81555230363     PISSN: None     EISSN: 14764598     Source Type: Journal    
DOI: 10.1186/1476-4598-10-143     Document Type: Article

References (39)

1. Cataldo VD, Gibbons DL, Perez-Soler R, Quintas-Cardama A. Treatment of non-small-cell lung cancer with erlotinib or gefitinib. N Engl J Med 2011, 364:947-955.
2. Douillard JY, Shepherd FA, Hirsh V, Mok T, Socinski MA, Gervais R, Liao ML, Bischoff H, Reck M, Sellers MV, et al. Molecular predictors of outcome with gefitinib and docetaxel in previously treated non-small-cell lung cancer: data from the randomized phase III INTEREST trial. J Clin Oncol 2010, 28:744-752.
3. Hirsch FR, Varella-Garcia M, Bunn PA, Franklin WA, Dziadziuszko R, Thatcher N, Chang A, Parikh P, Pereira JR, Ciuleanu T, et al. Molecular predictors of outcome with gefitinib in a phase III placebo-controlled study in advanced non-small-cell lung cancer. J Clin Oncol 2006, 24:5034-5042.
4. Janne PA, Gray N, Settleman J. Factors underlying sensitivity of cancers to small-molecule kinase inhibitors. Nat Rev Drug Discov 2009, 8:709-723.
5. Engelman JA, Janne PA. Mechanisms of acquired resistance to epidermal growth factor receptor tyrosine kinase inhibitors in non-small cell lung cancer. Clin Cancer Res 2008, 14:2895-2899.
6. van Erp NP, Gelderblom H, Guchelaar HJ. Clinical pharmacokinetics of tyrosine kinase inhibitors. Cancer Treat Rev 2009, 35:692-706.
7. Huang Y, Sadee W. Membrane transporters and channels in chemoresistance and -sensitivity of tumor cells. Cancer Lett 2006, 239:168-182.
8. Li X, Kamenecka TM, Cameron MD. Bioactivation of the epidermal growth factor receptor inhibitor gefitinib: implications for pulmonary and hepatic toxicities. Chem Res Toxicol 2009, 22:1736-1742.
9. Galetti M, Alfieri RR, Cavazzoni A, La Monica S, Bonelli M, Fumarola C, Mozzoni P, De Palma G, Andreoli R, Mutti A, et al. Functional characterization of gefitinib uptake in non-small cell lung cancer cell lines. Biochem Pharmacol 2010, 80:179-187.
10. Swaisland HC, Cantarini MV, Fuhr R, Holt A. Exploring the relationship between expression of cytochrome P450 enzymes and gefitinib pharmacokinetics. Clin Pharmacokinet 2006, 45:633-644.
11. McKillop D, McCormick AD, Millar A, Miles GS, Phillips PJ, Hutchison M. Cytochrome P450-dependent metabolism of gefitinib. Xenobiotica 2005, 35:39-50.
12. Li J, Zhao M, He P, Hidalgo M, Baker SD. Differential metabolism of gefitinib and erlotinib by human cytochrome P450 enzymes. Clin Cancer Res 2007, 13:3731-3737.
13. McKillop D, Hutchison M, Partridge EA, Bushby N, Cooper CM, Clarkson-Jones JA, Herron W, Swaisland HC. Metabolic disposition of gefitinib, an epidermal growth factor receptor tyrosine kinase inhibitor, in rat, dog and man. Xenobiotica 2004, 34:917-934.
14. McKillop D, McCormick AD, Miles GS, Phillips PJ, Pickup KJ, Bushby N, Hutchison M. In vitro metabolism of gefitinib in human liver microsomes. Xenobiotica 2004, 34:983-1000.
15. Androutsopoulos VP, Tsatsakis AM, Spandidos DA. Cytochrome P450 CYP1A1: wider roles in cancer progression and prevention. BMC Cancer 2009, 9:187.
16. Bieche I, Narjoz C, Asselah T, Vacher S, Marcellin P, Lidereau R, Beaune P, de Waziers I. Reverse transcriptase-PCR quantification of mRNA levels from cytochrome (CYP)1, CYP2 and CYP3 families in 22 different human tissues. Pharmacogenet Genomics 2007, 17:731-742.
17. Thum T, Erpenbeck VJ, Moeller J, Hohlfeld JM, Krug N, Borlak J. Expression of xenobiotic metabolizing enzymes in different lung compartments of smokers and nonsmokers. Environ Health Perspect 2006, 114:1655-1661.
18. La Monica S, Galetti M, Alfieri RR, Cavazzoni A, Ardizzoni A, Tiseo M, Capelletti M, Goldoni M, Tagliaferri S, Mutti A, et al. Everolimus restores gefitinib sensitivity in resistant non-small cell lung cancer cell lines. Biochem Pharmacol 2009, 78:460-468.
19. Carp H, Janoff A. Possible mechanisms of emphysema in smokers. In vitro suppression of serum elastase-inhibitory capacity by fresh cigarette smoke and its prevention by antioxidants. Am Rev Respir Dis 1978, 118:617-621.
20. Drakoulis N, Cascorbi I, Brockmoller J, Gross CR, Roots I. Polymorphisms in the human CYP1A1 gene as susceptibility factors for lung cancer: exon-7 mutation (4889 A to G), and a T to C mutation in the 3'-flanking region. Clin Investig 1994, 72:240-248.
21. Hayashi SI, Watanabe J, Nakachi K, Kawajiri K. PCR detection of an A/G polymorphism within exon 7 of the CYP1A1 gene. Nucleic Acids Res 1991, 19:4797.
22. Cavazzoni A, Alfieri RR, Carmi C, Zuliani V, Galetti M, Fumarola C, Frazzi R, Bonelli M, Bordi F, Lodola A, et al. Dual mechanisms of action of the 5-benzylidene-hydantoin UPR1024 on lung cancer cell lines. Mol Cancer Ther 2008, 7:361-370.
23. Alfieri RR, Bonelli MA, Cavazzoni A, Brigotti M, Fumarola C, Sestili P, Mozzoni P, De Palma G, Mutti A, Carnicelli D, et al. Creatine as a compatible osmolyte in muscle cells exposed to hypertonic stress. J Physiol 2006, 576:391-401.
24. Kennedy SW, Jones SP. Simultaneous measurement of cytochrome P4501A catalytic activity and total protein concentration with a fluorescence plate reader. Anal Biochem 1994, 222:217-223.
25. Ozvegy-Laczka C, Hegedus T, Varady G, Ujhelly O, Schuetz JD, Varadi A, Keri G, Orfi L, Nemet K, Sarkadi B. High-affinity interaction of tyrosine kinase inhibitors with the ABCG2 multidrug transporter. Mol Pharmacol 2004, 65:1485-1495.
26. Shimada T, Gillam EM, Sutter TR, Strickland PT, Guengerich FP, Yamazaki H. Oxidation of xenobiotics by recombinant human cytochrome P450 1B1. Drug Metab Dispos 1997, 25:617-622.
27. Doostdar H, Burke MD, Mayer RT. Bioflavonoids: selective substrates and inhibitors for cytochrome P450 CYP1A and CYP1B1. Toxicology 2000, 144:31-38.
28. Shimada T, Yamazaki H, Foroozesh M, Hopkins NE, Alworth WL, Guengerich FP. Selectivity of polycyclic inhibitors for human cytochrome P450s 1A1, 1A2, and 1B1. Chem Res Toxicol 1998, 11:1048-1056.
29. Dubey RK, Gillespie DG, Zacharia LC, Barchiesi F, Imthurn B, Jackson EK. CYP450- and COMT-derived estradiol metabolites inhibit activity of human coronary artery SMCs. Hypertension 2003, 41:807-813.
30. Fradette C, Du Souich P. Effect of hypoxia on cytochrome P450 activity and expression. Curr Drug Metab 2004, 5:257-271.
31. van Schaik RH. CYP450 pharmacogenetics for personalizing cancer therapy. Drug Resist Updat 2008, 11:77-98.
32. McKillop D, Guy SP, Spence MP, Kendrew J, Kemp JV, Bushby N, Wood PG, Barnett S, Hutchison M. Minimal contribution of desmethyl-gefitinib, the major human plasma metabolite of gefitinib, to epidermal growth factor receptor (EGFR)-mediated tumour growth inhibition. Xenobiotica 2006, 36:29-39.
33. Anttila S, Hukkanen J, Hakkola J, Stjernvall T, Beaune P, Edwards RJ, Boobis AR, Pelkonen O, Raunio H. Expression and localization of CYP3A4 and CYP3A5 in human lung. Am J Respir Cell Mol Biol 1997, 16:242-249.
34. Hukkanen J, Lassila A, Paivarinta K, Valanne S, Sarpo S, Hakkola J, Pelkonen O, Raunio H. Induction and regulation of xenobiotic-metabolizing cytochrome P450s in the human A549 lung adenocarcinoma cell line. Am J Respir Cell Mol Biol 2000, 22:360-366.
35. Sutter CH, Yin H, Li Y, Mammen JS, Bodreddigari S, Stevens G, Cole JA, Sutter TR. EGF receptor signaling blocks aryl hydrocarbon receptor-mediated transcription and cell differentiation in human epidermal keratinocytes. Proc Natl Acad Sci USA 2009, 106:4266-4271.
36. Zhou SF, Liu JP, Chowbay B. Polymorphism of human cytochrome P450 enzymes and its clinical impact. Drug Metab Rev 2009, 41:89-295.
37. Nie Q, Yang XN, An SJ, Zhang XC, Yang JJ, Zhong WZ, Liao RQ, Chen ZH, Su J, Xie Z, Wu YL. CYP1A1*2A polymorphism as a predictor of clinical outcome in advanced lung cancer patients treated with EGFR-TKI and its combined effects with EGFR intron 1 (CA)n polymorphism. Eur J Cancer 2011, 47:1962-1970.
38. Inoue A, Saijo Y, Maemondo M, Gomi K, Tokue Y, Kimura Y, Ebina M, Kikuchi T, Moriya T, Nukiwa T. Severe acute interstitial pneumonia and gefitinib. Lancet 2003, 361:137-139.
39. Kudoh S, Kato H, Nishiwaki Y, Fukuoka M, Nakata K, Ichinose Y, Tsuboi M, Yokota S, Nakagawa K, Suga M, et al. Interstitial lung disease in Japanese patients with lung cancer: a cohort and nested case-control study. Am J Respir Crit Care Med 2008, 177:1348-1357.