Modulation of CYP3A4 activity and induction of apoptosis, necrosis and senescence by the anti-tumour imidazoacridinone C-1311 in human hepatoma cells

Cell Biology International

Volumn 37, Issue 2, 2013, Pages 109-120

  Augustin, Ewa ^a   Pawłowska, Monika ^a   Polewska, Joanna ^a   Potega, Agnieszka ^a   Mazerska, Zofia ^a  

^a GDANSK UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

Anti tumour acridinones; Cell death; CYP3A4 inhibition; HepG2 cells; Senescence

Indexed keywords

4',6 DIAMIDINO 2 PHENYLINDOLE; BETA GALACTOSIDASE; CYTOCHROME P450 3A4; DOXORUBICIN; IMIDACRINE; PHOSPHATIDYLSERINE;

APOPTOSIS; ARTICLE; BIOACCUMULATION; CANCER CELL CULTURE; CELL AGING; CELL CYCLE PARAMETERS; CELL METABOLISM; CELL SURVIVAL; CELLULAR DISTRIBUTION; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYP3A4 GENE; DRUG CYTOTOXICITY; DRUG METABOLISM; DRUG TARGETING; ENZYME REGULATION; GENE OVEREXPRESSION; GENETIC VARIABILITY; HUMAN; HUMAN CELL; LIVER CELL CARCINOMA; METABOLITE; SENESCENCE; STAINING;

AMINOACRIDINES; ANTINEOPLASTIC AGENTS; APOPTOSIS; CARCINOMA, HEPATOCELLULAR; CELL AGING; CELL LINE, TUMOR; CELL PROLIFERATION; CELL SURVIVAL; CYTOCHROME P-450 CYP3A; HUMANS; LIVER NEOPLASMS; NECROSIS;

EID: 84874709677     PISSN: 10656995     EISSN: 10958355     Source Type: Journal    
DOI: 10.1002/cbin.10018     Document Type: Article

References (38)

1. Augustin E, Mos-Rompa A, Skwarska A, Witkowski JM, Konopa J (2006) Induction of G2/M arrest and apoptosis of human leukemia cells by potent triazoloacridinone C-1305. Biochem Pharmacol 72: 1668-79.
2. Augustin E, Wheatley DN, Lamb J, Konopa J (1996) Imidazoacridinones arrest cell-cycle progression in the G2 phase of L1210 cells. Cancer Chemother Pharmacol 38: 39-44.
3. Berger B, Marquardt H,Westendorf J (1996) Pharmacological and toxicological aspects of new imidazoacridinone antitumour agents. Cancer Res 56: 2094-104.
4. Capizzi RL, Roman LA, Tjulandin S, Smirnova I, Manikhas A, Paterson JS, Major A, Lundberg AS, Fumoleau P (2008) Phase II trial of C-1311, a novel inhibitor of topoisomerase II in advanced breast cancer. J Clin Oncol 26: 1055.
5. Cholody WM, Martelli S, Konopa J (1992) Chromophore modified antineoplastic imidazoacridiones. Synthesis and activity against murine leukemias. J Med Chem 35: 378-82.
6. De Marco C, Zaffaroni N, Comijn E, Tesei A, Zoli W, Peters GJ (2007) Comparative evaluation of C-1311 cytotoxic activity and interference with cell cycle progression in a panel of human solid tumour and leukemia cell lines. Int J Oncol 31: 907-13.
7. Dziegielewski J, Slusarski B, Konitz A, Składanowski A, Konopa J (2002) Intercalation of imidazoacridinones to DNA and its relevance to cytotoxic and antitumour activity. Biochem Pharmacol 63: 1653-62.
8. Feierman DE, Melnikov Z, Zhang J (2002) The paradoxical effect of acetaminophen on CYP3A4 activity and content in transfected HepG2 cells. Arch Biochem Biophys 398: 109-17.
9. Goetz MP, Knox SK, Suman VJ, Rae JM, Safgren SL, Ames MM, Visscher DW, Reynolds C, Couch FJ, Lingle WL,Weinshilboum RM, Fritcher EG, Nibbe AM, Desta Z, Nguyen A, Flockhart DA, Perez EA, Ingle JN (2007) The impact of cytochrome P450 2D6 metabolism in women receiving adjuvant tamoxifen. Breast Cancer Res Treat 101: 113-21.
10. Guengerich FP (1999) Cytochrome P450 3A4: regulation and role in drug metabolism. Annu Rev Pharmacol Toxicol 139: 1-17.
11. Hewitt NJ, Hewitt P (2004) Phase I and II enzyme characterization of two sources of HepG2 cell lines. Xenobiotica 34: 243-56.
12. Holownia A, Braszko J (2004) Tamoxifen cytotoxicity in hepatoblastoma cells stably transfected with human CYP3A4. Biochem Pharmacol 67: 1057-64.
13. Hyzy M, Bożko P, Konopa J, Składanowski A (2005) Antitumour imidazoacridinone C-1311 induces cell death by mitotic catastrophe in human colon carcinoma cell. Biochem Pharmacol 69: 801-9.
14. IsambertN, Campone M, Bourbouloux E, Drouin M, Major A, Yin W, Loadman P, Capizzi R, Grieshaber C, Fumoleau P (2010) Evaluation of the safety of C-1311 (Symadex) administered in a phase I dose-escalation trial as a weekly infusion for 3 consecutive weeks in patients with advanced solid tumours. Eur J Cancer 46: 729-34.
15. Kostrubsky VE, Lewis LD, Strom SC, Wood SG, Schuetz EG, Schuetz JD, Sinclair PR, Wrighton SA, Sinclair JF (1998) Induction of cytochrome P4503A by Taxol in primary cultures of human hepatocytes. Arch Biochem Biophys 355: 131-6.
16. Lamb J, Wheatley DN (1996) Cell killing by the novel imidazoacridinone antineoplastic agent, C-1311, is inhibited at high concentrations coincident with dose-differentiated cell cycle perturbation. Br J Cancer 74: 1359-68.
17. Lu H, Waxman DJ (2005) Antitumour activity of methoxymorpholinyl doxorubicin: potentiation by cytochrome P450 3A metabolism. Mol Pharmacol 67: 212-9.
18. Lu X,Wan J, Cheng H, Li Y, Ao Y, Peng R (2008) Cytochrome P450 v-hydroxylase inhibition reduces cardiomyocyte apoptosis via activation of ERK1/2 signaling in rat myocardial ischemiareperfusion. Eur J Pharmacol 596: 118-26.
19. Martinez-Jimenez CP, Jover R, Donato MT, Castell JV, Gomez-Lechon MJ (2007) Transcriptional regulation and expression of CYP3A4 in hepatocytes. Curr Drug Metab 8: 185-94.
20. Mazerska Z,Dziegielewski J, Konopa J (2001) Enzymatic activation of new antitumour drug, 5-diethylaminoethylamino-8-hydroxyimidazoacridinone, C-1311, observed after its intercalation into DNA. Biochem Pharmacol 61: 685-94.
21. Mazerska Z, Sowi_nski P, Konopa J (2003) Molecular mechanism of the enzymatic oxidation investigated for imidazoacridinone antitumour drug, C-1311. Biochem Pharmacol 66: 1727-36.
22. Mitra R, Guo Z,Milani M,Mesaros C, Rodriguez M, Nguyen J, Luo X, Clarke D, Lamba J, Schuetz E, Donner DB, Puli N, Falck JR, Capdevila J, Gupta K, Blair IA, Potter DA (2011) CYP3A4 mediates growth of estrogen receptor-positive breast cancer cells in part by inducing nuclear translocation of phospho-3STAT through biosynthesis of ({{thorn}/_})14,15-epoxyeicosatrienoic acid (EET). J Biol Chem 20: 17543-59.
23. Oguro A, Sakamoto K, Funae Y, Imaoka S (2011) Overexpression of CYP3A4, but not CYP2D6, promotes hypoxic response and cell growth of Hep3B cells. Drug Metab Pharmacokinet 26: 407-15.
24. Poljakova J, Eckschlager T, Hrabeta J, Hrebackova J, Smutny S, Frei E, Martínek V, Kizek R, Stiborová M (2009) The mechanism of cytotoxicity and DNA adduct formation by the anticancer drug ellipticine in human neuroblastoma cells. Biochem Pharmacol 77: 1466-79.
25. Potega A, Dabrowska E, Niemira M, Kot-Wasik A, Ronseaux S, Henderson CJ, Wolf CR, Mazerska Z (2011) The imidazoacridinone antitumour drug, C-1311, is metabolized by flavin monooxygenases but not cytochrome P450s. Drug Metabol Dispos 39: 1423-32.
26. Rodriguez-Antona C, Leskela S, Zajac M, Cuadros M, Alves J, Moneo MV, Martín C, Cigudosa JC, Carnero A, Robledo M, Benitez J, Martínez-Delgado B (2007) Expression of CYP3A4 as a predictor of response to chemotherapy in peripheral T-cell lymphomas. Blood 110: 3345-51.
27. Saretzki G (2010) Cellular senescence in the development and treatment of cancer. Curr Pharm Des 16: 79-100.
28. Skwarska A, Augustin E, Konopa J (2007) Sequential induction of mitotic catastrophe followed by apoptosis in human leukemia MOLT4 cells by imidazoacridinone C-1311. Apoptosis 12: 2245-57.
29. Thomas AL, Anthoney A, Scott E, Ahmed S, Lundberg AS, Major A, Capizzi RL, Twelves CJ (2008) C-1311, a novel inhibitor of FLT3 and topoisomerase II: a phase 1 trial of once every three week schedule in patients with advanced solid tumours. J Clin Oncol 26: 2576.
30. Wang YJ, Yu ChF, Chen LCh, Chen CgH, Lin JK, Liang YC, Lin CH, Lin SY, Chen CF, Ho YS (2002) Ketoconazole potentiates terfenadine-induced apoptosis in human HepG2 cells through inhibition of cytochrome P450 3A4 activity. J Cell Biochem 87: 147-59.
31. Westernick WMA, Schoonen WGEJ (2007) Cytochrome P450 enzyme levels inHepG2 cells and cryopreserved primary human hepatocytes and their induction in HepG2 cells. Toxicol Vitro 21: 1581-91.
32. Wilkening S, Stahl F, Bader A (2003) Comparison of primary human hepatocytes and hepatoma cell line HepG2 with regard to their biotransformation properties. Drug Metab Dispos 31: 1035-42.
33. Wisniewska A, Chrapkowska A, Kot-Wasik A, Konopa J, Mazerska Z (2007) Metabolic transformations of antitumour imidazoacridinone, C-1311, with microsomal fractions of rat human liver enzymes. Acta Biochim Pol 54: 831-8.
34. Wojnowski L, Kamdem LK (2006) Clinical implications of CYP3A polymorphisms. Expert Opin Drug Metab Toxicol 2: 17182.
35. Yao D, Ding S, Burchell B, Wolf CR, Friedberg T (2000) Detoxication of vinca alkaloids by human P450 CYP3A4-mediated metabolism: implications for the development of drug resistance. J Pharmacol Exp Ther 294: 387-95.
36. Zaffaroni N, De Marco C, Villa R, Riboldi S, Daidone MG, Double JA (2001) Cell growth inhibition, G2M cell cycle arrest and apoptosis induced by the imidazoacridinone C-1311 in human tumour cell lines. Eur J Cancer 37: 1953-62.
37. Zucchini N, de Sousa G, Bailly-Maitre B, Gugenheim J, Bars R, Lemaire G, Rahmani R (2005) Regulation of Bcl-2 and Bcl-xL anti-apoptotic protein expression by nuclear receptor PXR in primary cultures of human and rat hepatocytes. Biochim Biophys Acta 1745: 48-58.
38. Zucchini-Pascal N, de Sousa G, Pizzol J, Rahmani R (2009) Pregnane X receptor activation protects rat hepatocytes against deoxycholic acid-induced apoptosis. Liver Int 30: 284-97.