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

References

• Slack J L, Gallagher R E. The molecular biology of acute promyelocytic leukemia. Cancer Treat Res 1999; 99: 75–124
   PubMedGoogle Scholar
• Warrell R P, Frankel S R, Miller W H. Differentiation therapy of acute promyelocytic leukemia with tretinoin (all-trans-retinoic acid). N Engl J Med 1991; 324: 1385–1393
   PubMed Web of Science ®Google Scholar
• Lotan R. Retinoids and apoptosis: implications for cancer chemoprevention and therapy. J Natl Cancer Inst 1995; 87: 1655–1657
   PubMed Web of Science ®Google Scholar
• Lotan R. Effects of vitamin A and its analogs (retinoids) on normal and neoplastic cells. Biochim Biophys Acta 1980; 605: 33–91
   PubMed Web of Science ®Google Scholar
• Lotan R. Vitamin A analogs (retinoids) as biological response modifiers. Prog Clin Biol Res 1988; 259: 261–271
   PubMedGoogle Scholar
• Chambon P. A decade of molecular biology of retinoic acid receptors. FASEB J 1999; 10: 940–954
   Google Scholar
• Tallman M S, Andersen J W, Schiffer C A, Appelbaum F R, Feusner J H, Woods W G, et al. All-trans retinoic acid in acute promyelocytic leukemia: long-term outcome and prognostic factor analysis from the North American Intergroup protocol. Blood 2002; 100: 4298–4302
   PubMed Web of Science ®Google Scholar
• Warrell R -P. Retinoid resistance in acute promyelocytic leukemia: new mechanisms, strategies, and implications. Blood 1992; 82: 1949–1953
   Web of Science ®Google Scholar
• Muindi J, Frankel S R, Miller W H, Javbowski A, Scheinberp D A, Young C W, et al. 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 1992; 79: 299–303
   PubMed Web of Science ®Google Scholar
• Lefebvre P, Thomas G, Gourmel B, Apader A, Castaipre S, Dreux C, et al. Pharmacokinetics of oral all-trans retinoic acid in patients with acute promyelocytic leukemia. Leukemia 1991; 5: 1054–1058
   PubMed Web of Science ®Google Scholar
• Muindi J -R, Young C -W, Warrell R -P. Clinical pharmacology of all-trans retinoic acid. Leukemia 1994; 8: 1807–1812
   PubMed Web of Science ®Google Scholar
• Smith M A, Adamson P C, Balis F M, Feusner J, Aronson L, Murphy R Fetal. Phase I and pharmacokinetic evaluation of all-trans-retinoic acid in pediatric patients with cancer. J Clin Oncol 1992; 10: 1666–1673
   PubMed Web of Science ®Google Scholar
• Napoli J-L. Interactions of retinoid binding proteins and enzymes in retinoid metabolism. Biochim Biophys Acta 1999; 1440: 139–162
   PubMed Web of Science ®Google Scholar
• Delva L, Cornic M, Balitrand N, Guidez F, Miclea J M, Delmer A, et al. Resistance to all-trans retinoic acid (ATRA) therapy in relapsing acute promyelocytic leukemia: study of in vitro ATRA sensitivity and cellular retinoic acid binding protein levels in leukemic cells. Blood 1993; 82: 2175–2181
   PubMed Web of Science ®Google Scholar
• Ozpolat B, Lopez-Berestein G, Adamson P, Fu C J, Williams A H. Pharmacokinetics of intravenously administered liposomal all-trans-retinoic acid (ATRA) and orally administered ATRA in healthy volunteers. J Pharm Pharm Sci 2003; 2: 292–301
   Google Scholar
• Harris M, Ozpolat B, Tirado-Gomez M, Bradbury E M, Lopez-Berestein G, Chen X. Comparative proteomics analysis of all-trans-retinoic acid treatment reveals systematic post-transcriptional control mechanisms in acute promyelocytic leukemia. Blood 2004; 104: 1314–1323
   PubMed Web of Science ®Google Scholar
• Shao W, Benedetti L, Lamph W -W, Nervi C, Miller W -H. A retinoid-resistant acute promyelocytic leukemia subclone expresses a dominant negative PML-RAR alpha mutation. Blood 1997; 89: 4282–4289
   PubMed Web of Science ®Google Scholar
• Ozpolat B, Lopez-Berestein G, Mehta K. ATRA(ouble) in treatment of acute promyelocytic leukemia. J Biol Regul Homeostatic Agents 2001; 15: 107–122
   PubMed Web of Science ®Google Scholar
• Mehta K, Sadeghi T, McQueen T, Lopez-Berestein G. Liposome encapsulation circumvents the hepatic clearance mechanisms of all-trans-retinoic acid. Leuk Res 1994; 18: 587–596
   PubMed Web of Science ®Google Scholar
• Estey E, Thall P F, Mehta K, Rosenblum M, Brewer T, Simmons V, et al. Alterations in tretinoin pharmacokinetics following administration of liposomal all-trans retinoic acid. Blood 1996; 87: 3650–3654
   PubMed Web of Science ®Google Scholar
• Tsimberidou A M, Tirado-Gomez M, Andreeff M S, O'Brien H M, Kantarjian M J, Keating G, et al. Single agent liposomal-encapsulated (Lipo) all-trans retinoic acid (ATRA) can cure patients with untreated acute promyelocytic leukemia (APL): an update and comparison with an ATRA + idarubicin induction regimen. J Clin Oncol 2004; 6513, 2004 ASCO Annual Meeting Proceedings (Post-Meeting Edition). Vol 22, No 14S (July 15 Supplement)
   Web of Science ®Google Scholar
• White J A, Beckett-Jones B, Guo Y D, Dilworth F J, Bonasoro J, Jones G, Petkoulch M. cDNA cloning of human retinoic acid-metabolizing enzyme (hP450RAI) identifies a novel family of cytochromes P450. J Biol Chem 1997; 272: 18538–18541
   PubMed Web of Science ®Google Scholar
• Ray W -J, Bain G, Yao M, Gottlieb D -I. CYP26, a novel mammalian cytochrome P450, is induced by retinoic acid and defines a new family. J Biol Chem 1997; 272: 18702–18708
   PubMed Web of Science ®Google Scholar
• White J A, Ramshaw H, Taimi M, Stangle W, Zhang A, Everingham S, et al. 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 2000; 12: 6403–6408
   Web of Science ®Google Scholar
• Taimi M, Helvig C, Wisniewski J, Ramshaw H, White J, Amad M, et al. A novel human cytochrome P450, CYP26C1 involved in metabolism of 9-cis and all-trans, isomers of retinoic acid. J Biol Chem 2003; 15: 713–719
   Google Scholar
• Ozpolat B, Mehta K, Tari A M, Lopez-Berestein G. All-trans-retinoic acid-induced expression and regulation of retinoic acid 4-hydroxylase (CYP26) in human promyelocytic leukemia. Am J Hematol 2002; 70: 39–47
   PubMed Web of Science ®Google Scholar
• Diaz B, Lopez-Berestein G. A distinct element involved in lipopolysaccharide activation of the tumor necrosis factor-alpha promoter in monocytes. J Interferon Cytokine Res 2000; 20: 741–748
   PubMed Web of Science ®Google Scholar
• Gubler M L, Sherman S I. Metabolism of retinoic acid and retinol by intact cells and cell extracts. Methods Enzymol 189; 60: 525–530
   Google Scholar
• Lansink M, van Bennekum A M, Blaner W S, Kooistra T. Differences in metabolism and isomerization of all-trans-retinoic acid and 9-cis-retinoic acid between human endothelial cells and hepatocytes. Eur J Biochem 1997; 247: 596–604
   PubMedGoogle Scholar
• Adamson P C, Bailey J, Pluda J, Poplack D, Bavza S, Murphy R F, et al. Pharmacokinetics of all-trans-retinoic acid administered on an intermittent schedule. J Clin Oncol 1995; 13: 1238–1241
   PubMed Web of Science ®Google Scholar
• Parthasarathy R, Mehta K. Altered metabolism of all-trans-retinoic acid in liposome-encapsulated form. Cancer Lett 1998; 134: 121–128
   PubMed Web of Science ®Google Scholar
• McSorley L -C, Daly A -K. Identification of human cytochrome P450 isoforms that contribute to all- trans-retinoic acid 4-hydroxylation. Biochem Pharmacol 2000; 60: 517–521
   PubMed Web of Science ®Google Scholar
• Muindi J R, Young C W, Warrell R P. Clinical pharmacology of all-trans retinoic acid. Leukemia 1994; 8: 1807–1812
   PubMed Web of Science ®Google Scholar
• Cornic M, Delva L, Guidez F, Balitrand N, Degos L, Chomienne C. Induction of retinoic acid-binding protein in normal and malignant human myeloid cells by retinoic acid in acute promyelocytic leukemia patients. Cancer Res 1992; 52: 3329–3334
   PubMed Web of Science ®Google Scholar
• Adamson P C, Boylan J F, Balis F M, Murphy R F, Godwin K A, Gudas L J, Poplack D G. Time course of induction of metabolism of all-trans-retinoic acid and the up-regulation of cellular retinoic acid-binding protein. Cancer Res 1993; 53: 472–476
   PubMed Web of Science ®Google Scholar
• Rigas J R, Francis P A, Muindi J R, Kris M G, Huselton C, DeGrazia F, et al. Constitutive variability in the pharmacokinetics of the natural retinoid, all-trans-retinoic acid, and its modulation by ketoconazole. J Natl Cancer Inst 1993; 85: 1921–1926
   PubMed Web of Science ®Google Scholar
• Miller W H. The emerging role of retinoids and retinoic acid metabolism blocking agents in the treatment of cancer. Cancer 1998; 83: 1471–1482
   PubMed Web of Science ®Google Scholar
• Lopez-Berestein G, Rosenblum M, Sadeghi T, Mehta K. Pharmacokinetics, tissue distribution, and toxicity of tretinoin incorporated in liposomes. J Liposome Res 1994; 4: 689–700
   Google Scholar
• Lopez-Berestein G, Kasi L, Rosenblum M G, Haynie T, Jahns M, Glenn H, et al. Clinical pharmacology of 99mTc-labeled liposomes in patients with cancer. Cancer Res 1984; 44: 375–378
   PubMed Web of Science ®Google Scholar
• Estey E H, Giles F J, Kantarjian H, O'Brien S, Cortes J, Freireich E J, et al. Molecular remissions induced by liposomal-encapsulated all-trans retinoic acid in newly diagnosed acute promyelocytic leukemia. Blood 1999; 94: 2230–2235
   PubMed Web of Science ®Google Scholar
• Ozpolat B, Lopez-Berestein G. Liposomal-all-trans-retinoic acid in treatment of acute promyelocytic leukemia. Leuk Lymphoma 2002; 43: 933–941
   PubMed Web of Science ®Google Scholar