Molecular targeting of retinoic acid metabolism in neuroblastoma: The role of the CYP26 inhibitor R116010 in vitro and in vivo

British Journal of Cancer

Volumn 96, Issue 11, 2007, Pages 1675-1683

  Armstrong, J L ^a   Taylor, G A ^a   Thomas, H D ^a   Boddy, A V ^a   Redfern, C P F ^a   Veal, G J ^a  

^a NEWCASTLE UNIVERSITY   (United Kingdom)

Author keywords

CYP26; Neuroblastoma; R116010; Retinoic acid

Indexed keywords

13 4 OXO RETINOIC ACID; 4 OXO RETINOIC AACID; ANTINEOPLASTIC AGENT; CYTOCHROME P450 26 INHIBITOR; DRUG METABOLITE; ISOTRETINOIN; R 116010; RETINOIC ACID; UNCLASSIFIED DRUG;

ADD ON THERAPY; ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; COMBINATION CHEMOTHERAPY; CONTROLLED STUDY; DRUG DOSE INCREASE; DRUG METABOLISM; DRUG POTENTIATION; DRUG TARGETING; ENZYME INDUCTION; FEMALE; GENE EXPRESSION; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; MARKER GENE; MONOTHERAPY; MOUSE; NEUROBLASTOMA; NONHUMAN; PHARMACODYNAMICS; PRIORITY JOURNAL; RNA INTERFERENCE; XENOGRAFT;

ANIMALS; BENZOTHIAZOLES; CELL LINE, TUMOR; CYTOCHROME P-450 ENZYME SYSTEM; DRUG EVALUATION, PRECLINICAL; FEMALE; HUMANS; IMIDAZOLES; ISOENZYMES; MICE; MICE, NUDE; NEUROBLASTOMA; RNA, SMALL INTERFERING; TRANSPLANTATION, HETEROLOGOUS; TRETINOIN;

EID: 34249783140     PISSN: 00070920     EISSN: 15321827     Source Type: Journal    
DOI: 10.1038/sj.bjc.6603779     Document Type: Article

References (27)

1. Andreola F, Hayhurst GP, Luo G, Ferguson SS, J GF, Goldstein JA, De Luca LM (2004) Mouse liver CYP2C39 is a novel retinoic acid 4-hydroxylase. Its down-regulation offers a molecular basis for liver retinoid accumulation and fibrosis in aryl hydrocarbon receptor-null mice. J Biol Chem 279: 3434-3438
2. Armstrong JL, Redfern CPF, Veal GJ (2005a) 13-cis retinoic acid and isomerisation in paediatric oncology - is changing shape the key to success? Biochem Pharmacol 69: 1299-1306
3. Armstrong JL, Ruiz M, Boddy AV, Redfern CPF, Pearson ADJ, Veal GJ (2005b) Increasing the intracellular availability of all-trans-retinoic acid in neuroblastoma cells. Br J Cancer 92: 696-704
4. Blaner WS (2001) Cellular metabolism and actions of 13-cis- retinoic acid. J Am Acad Dermatol 45: S129-S135
5. Conley BA, Ramsland TS, Sentz DL, Wu S, Rosen DM, Wollman M, Eiseman JL (1999) Antitumor activity, distribution, and metabolism of 13-cis-retinoic acid as a single agent or in combination with tamoxifen in established human MCF-7 xenografts in mice. Cancer Chemother Pharmacol 43: 183 -197
6. Heise R, Mey J, Neis MM, Marquardt Y, Joussen S, Ott H, Wiederholt T, Kurschat P, Megahed M, Bickers DR, Merk HF, Baron JM (2006) Skin retinoid concentrations are modulated by CYP26AI expression restricted to basal keratinocytes in normal human skin and differentiated 3D skin models. J Invest Dermatol 126: 2473-2480
7. Idres N, Marill J, Flexor MA, Chabot GG (2002) Activation of retinoic acid receptor-dependent transcription by all-trans-retinoic acid metabolites and isomers. J Biol Chem 277: 31491-31498
8. Mangelsdorf DJ, Borgmeyer U, Heyman RA, Zhou JY, Ong ES, Oro AE, Kakizuka A, Evans RM (1992) Characterization of three RXR genes that mediate the action of 9-cis retinoic acid. Genes Dev 6: 329-344
9. Marill J, Capron CC, Idres N, Chabot GG (2002) Human cytochrome P450s involved in the metabolism of 9-cis- and 13-cis-retinoic acids. Biochem Pharmacol 63: 933-943
10. Marill J, Cresteil T, Lanotte M, Chabot GG (2000) Identification of human cytochrome P450s involved in the formation of all-trans-retinoic acid principal metabolites. Mol Pharmacol 58: 1341-1348
11. Matthay KK, Villablanca JG, Seeger RC, Stram DO, Harris RE, Ramsay NK, Swift P, Shimada H, Black CT, Brodeur GM, Gerbing RB, Reynolds CP (1999) Treatment of high-risk neuroblastoma with intensive chemotherapy, radiotherapy, autologous bone marrow transplantation, and 13-cis-retinoic acid. Children's Cancer Group. N Engl J Med 341: 1165-1173
12. Muindi J, Frankel SR, Miller WH, Jakubowski A, Scheinberg DA, Young CW, Dmitrovsky E, Warrell RPJ (1992) Continuous treatment with all-trans retinoic acid causes a progressive reduction in plasma drug concentrations: implications for relapse and retinoid resistance in patients with acute promyelocytic leukemia. Blood 79: 299-303
13. Njar VC, Gediya L, Purushottamachar P, Chopra P, Vasaitis TS, Khandelwal A, Mehta J, Huynh C, Belosay A, Patel J (2006) Retinoic acid metabolism blocking agents (RAMBAs) for treatment of cancer and dermatological diseases. Bioorg Med Chem 14: 4323-4340
14. Njar VCO (2002) Cytochrome P450 retinoic acid 4-hydroxylase inhibitors: potential agents for cancer therapy. Mini Rev Med Chem 2: 261-269
15. Ozpolat B, Mehta K, Lopez-Berestein G (2005) Regulation of a highly specific retinoic acid-4-hydroxylase (CYP26A1) enzyme and all-trans- retinoic acid metabolism in human intestinal, liver, endothelial, and acute promyelocytic leukemia cells. Leuk Lymphoma 46: 1497-1506
16. Petkovich M, Brand NJ, Krust A, Chambon P (1987) A human retinoic acid receptor which belongs to the family of nuclear receptors. Nature 330: 444-450
17. Ponthan F, Borgstrom P, Hassan M, Wassberg E, Redfern CPF, Kogner P (2001) The vitamin A analogues: 13-cis retinoic acid, 9-cis retinoic acid, and Ro 13-6307 inhibit neuroblastoma tumour growth in vivo. Med Pediatr Oncol 36: 127-131
18. Reynolds CP, Matthay KK, Villablanca JG, Maurer BJ (2003) Retinoid therapy of high-risk neuroblastoma. Cancer Lett 197: 182-192
19. Smith G, Ibbotson SH, Comrie MM, Dawe RS, Bryden A, Ferguson J, Wolf CR (2006) Regulation of cutaneous drug-metabolizing enzymes and cytoprotective gene expression by topical drugs in human skin in vivo. Br J Dermatol 155: 275-281
20. Taimi M, Helvig C, Wisniewski J, Ramshaw H,White J, Amad M, Korczak B, Petkovich M (2004) A novel human cytochrome P450, CYP26C1, involved in metabolism of 9-cis and all-trans isomers of retinoic acid. J Biol Chem 279: 77-85
21. Tsukada M, Schroder M, Roos TC, Chandraratna RA, Reichert U, Merk HF, Orfanos CE, Zouboulis CC (2000) 13-cis retinoic acid exerts its specific activity on human sebocytes through selective intracellular isomerization to all-trans retinoic acid and binding to retinoid acid receptors. J Invest Dermatol 115: 321-327
22. Van Heusden J, Van Ginckel R, Bruwiere H, Moelans P, Janssen B, Floren W, van der Leede BJ, van Dun J, Sanz G, Venet M, Dillen L, Van Hove C, Willemsens G, Janicot M, Wouters W (2002) Inhibition of all-trans-retinoic acid metabolism by R116010 induces antitumour activity. Br J Cancer 86: 605-611
23. Veal GJ, Cole M, Errington J, Pearson ADJ, Foot ABM, Whyman G, Boddy AV (2007) Pharmacokinetics and metabolism of 13-cis-retinoic acid (isotretinoin) in children with high-risk neuroblastoma - a study of the United Kingdom Children's Cancer Study Group. Br J Cancer 96: 424-431
24. Veal GJ, Errington J, Redfern CPF, Pearson ADJ, Boddy AV (2002) Influence of isomerisation on the growth inhibitory effects and cellular activity of 13-cis and all-trans retinoic acid in neuroblastoma cells. Biochem Pharmacol 63: 207-215
25. Villablanca JG, Khan AA, Avramis VI, Seeger RC, Matthay KK, Ramsay NK, Reynolds CP (1995) Phase I trial of 13-cis-retinoic acid in children with neuroblastoma following bone marrow transplantation. J Clin Oncol 13: 894-901
26. White JA, Beckett-Jones B, Guo YD, Dilworth FJ, Bonasoro J, Jones G, Petkovich M (1997) cDNA cloning of human retinoic acid-metabolizing enzyme (hP450RAI) identifies a novel family of cytochromes P450. J Biol Chem 272: 18538-18541
27. White JA, Ramshaw H, Taimi M, Stangle W, Zhang A, Everingham S, Creighton S, Tam S-P, Jones G, Petkovich M (2000) Identification of the human cytochrome P450, P450RAI-2, which is predominantly expressed in the adult cerebellum and is responsible for all-trans-retinoic acid metabolism. Proc Natl Acad Sci USA 97: 6403-6408