DNA methylation and its involvement in carboxylesterase 1A1 (CES1A1) gene expression

Xenobiotica

Volumn 40, Issue 2, 2010, Pages 119-128

  Hori, T ^a   Hosokawa, M ^a  

^a CHIBA INSTITUTE OF SCIENCE   (Japan)

Author keywords

CpG island; Oseltamivir; Prodrug; Tissue specific expression

Indexed keywords

5 AZA 2' DEOXYCYTIDINE; BISULFITE; CARBOXYLASE; CARBOXYLESTERASE 1A1; UNCLASSIFIED DRUG;

ARTICLE; CELL STRAIN HEK293; CONTROLLED STUDY; DNA METHYLATION; DRUG MECHANISM; ENZYME ACTIVATION; GENE EXPRESSION; HEPATOMA CELL; HUMAN; HUMAN CELL; TRANSCRIPTION INITIATION SITE;

AZACITIDINE; BASE SEQUENCE; CARBOXYLESTERASE; CELL LINE; DNA METHYLATION; GENE EXPRESSION; HUMANS; HYDROLYSIS; KIDNEY; LIVER; MOLECULAR SEQUENCE DATA; NITROPHENOLS; RNA, MESSENGER; TRANSCRIPTIONAL ACTIVATION;

EID: 75649101801     PISSN: 00498254     EISSN: 13665928     Source Type: Journal    
DOI: 10.3109/00498250903431794     Document Type: Article

References (42)

1. Anttila S, Hakkola J, Tuominen P, Elovaara E, Husgafvel-Pursiainen K, Karjalainen A, Hirvonen A, Nurminen T. (2003). Methylation of cytochrome P4501A1 promoter in the lung is associated with tobacco smoking. Cancer Res 63(24):8623-8628
2. Aoki M, Terada T, Kajiwara M, Ogasawara K, Ikai I, Ogawa O, Katsura T, Inui K. (2008). Kidney-specific expression of human organic cation transporter 2 (OCT2/SLC22A2) is regulated by DNA methylation. Am J Phys 295(1):F165-70.
3. Appanah R, Dickerson DR, Goyal P, Groudine M, Lorincz MC. (2007). An unmethylated 3″ promoter-proximal region is required for efficient transcription initiation. PLoS Genet 3(2):e27.
4. Bencharit S, Morton CL, Hyatt JL, Kuhn P, Danks MK, Potter PM, Redinbo MR. (2003). Crystal structure of human carboxylesterase 1 complexed with the Alzheimer's drug tacrine: from binding promiscuity to selective inhibition. Chem Biol 10(4):341-349
5. Bird A. (2002). DNA methylation patterns and epigenetic memory. Genes Develop 16(1):6-21.
6. Bird AP, Wolffe AP. (1999). Methylation-induced repression - belts, braces, and chromatin. Cell 99(5):451-454
7. Bjornsson HT, Sigurdsson MI, Fallin MD, Irizarry RA, Aspelund T, Cui H, Yu W, Rongione MA, Ekstrom TJ, Harris TB, Launer LJ, Eiriksdottir G, Leppert MF, Sapienza C, Gudnason V, Feinberg AP. (2008). Intra-individual change over time in DNA methylation with familial clustering. J Am Med Assoc 299(24):2877-2883
8. Cameron EE, Bachman KE, Myohanen S, Herman JG, Baylin SB. (1999). Synergy of demethylation and histone deacetylase inhibition in the re-expression of genes silenced in cancer. Nat Genet 21(1):103-107
9. Coffee B, Zhang F, Warren ST, Reines D. (1999). Acetylated histones are associated with FMR1 in normal but not fragile X-syndrome cells. Nat Genet 22(1):98-101.
10. El-Osta A, Kantharidis P, Zalcberg JR, Wolffe AP. (2002). Precipitous release of methyl-CpG binding protein 2 and histone deacetylase 1 from the methylated human multidrug resistance gene (MDR1) on activation. Molecular Cell Biol 22(6):1844-1857
11. Fukami T, Nakajima M, Maruichi T, Takahashi S, Takamiya M, Aoki Y, McLeod HL, Yokoi T. (2008). Structure and characterization of human carboxylesterase 1A1, 1A2, and 1A3 genes. Pharmacogenet Genomics 18(10):911-920
12. Gagnon JF, Bernard O, Villeneuve L, Tetu B, Guillemette C. (2006). Irinotecan inactivation is modulated by epigenetic silencing of UGT1A1 in colon cancer. Clin Cancer Res 12(6):1850-1858
13. Graessmann A, Sandberg G, Guhl E, Graessmann M. (1994). Methylation of single sites within the herpes simplex virus tk coding region and the simian virus 40 T-antigen intron causes gene inactivation. Mol Cell Biol 14(3):2004-2010
14. Heymann E, Mentlein R, Schmalz R, Schwabe C, Wagenmann F. (1979). A method for the estimation of esterase synthesis and degradation and its application to evaluate the influence of insulin and glucagon. Eur J Biochem 102(2):509-519
15. Hisano M, Ohta H, Nishimune Y, Nozaki M. (2003). Methylation of CpG dinucleotides in the open reading frame of a testicular germ cell-specific intronless gene, Tact1/Actl7b, represses its expression in somatic cells. Nucleic Acids Res 31(16):4797-4804
16. Hosokawa M. (2008). Structure and catalytic properties of carboxylesterase isozymes involved in metabolic activation of prodrugs. Molecules (Basel) 13(2):412-431
17. Hosokawa M, Furihata T, Yaginuma Y, Yamamoto N, Watanabe N, Tsukada E, Ohhata Y, Kobayashi K, Satoh T, Chiba K. (2008). Structural organization and characterization of the regulatory element of the human carboxylesterase (CES1A1 and CES1A2) genes. Drug Metab Pharmacokinet 23(1):73-84.
18. Hosokawa M, Maki T, Satoh T. (1987). Multiplicity and regulation of hepatic microsomal carboxylesterases in rats. Mol Pharmacol 31(6):579-584
19. Ishizuka H, Konno K, Naganuma H, Sasahara K, Kawahara Y, Niinuma K, Suzuki H, Sugiyama Y. (1997). Temocaprilat, a novel angiotensin-converting enzyme inhibitor, is excreted in bile via an ATP-dependent active transporter (cMOAT) that is deficient in Eisai hyperbilirubinemic mutant rats (EHBR). J Pharmacol Exp Ther 280(3):1304-1311
20. Izumi Y, Tokuda K, O'Dell K A, Zorumski CF, Narahashi T. (2007). Neuroexcitatory actions of Tamiflu and its carboxylate metabolite. Neurosci Lett 426(1):54-58
21. Kikuchi R, Kusuhara H, Hattori N, Kim I, Shiota K, Gonzalez FJ, Sugiyama Y. (2007). Regulation of tissue-specific expression of the human and mouse urate transporter 1 gene by hepatocyte nuclear factor 1 alpha/beta and DNA methylation. Mol Pharmacol 72(6):1619-1625
22. Kondo Y, Shen L, Issa JP. (2003). Critical role of histone methylation in tumor suppressor gene silencing in colorectal cancer. Mol Cell Biol 23(1):206-215
23. Kumaki Y, Oda M, Okano M. (2008). QUMA: quantification tool for methylation analysis. Nucleic Acids Res 36(Web Server issue):W170-5.
24. Larsen F, Gundersen G, Lopez R, Prydz H. (1992). CpG islands as gene markers in the human genome. Genomics 13(4):1095-1107
25. Li B, Carey M, Workman JL. (2007). The role of chromatin during transcription. Cell 128(4):707-719
26. Li LC, Dahiya R. (2002). MethPrimer: designing primers for methylation PCRs. Bioinformatics 18(11):1427-1431
27. Lin JC, Jeong S, Liang G, Takai D, Fatemi M, Tsai YC, Egger G, Gal-Yam EN, Jones PA. (2007). Role of nucleosomal occupancy in the epigenetic silencing of the MLH1 CpG island. Cancer Cell 12(5):432-444
28. McGurk KA, Brierley CH, Burchell B. (1998). Drug glucuronidation by human renal UDP-glucuronosyltransferases. Biochem Pharmacol 55(7):1005-1012
29. Morimoto K, Nakakariya M, Shirasaka Y, Kakinuma C, Fujita T, Tamai I, Ogihara T. (2008). Oseltamivir (Tamiflu) efflux transport at the blood-brain barrier via P-glycoprotein. Drug Metab Disposit 36(1):6-9.
30. Ose A, Ito M, Kusuhara H, Yamatsugu K, Kanai M, Shibasaki M, Hosokawa M, Schuetz JD, Sugiyama Y. (2009). Limited brain distribution of [3R,4R,5S]-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate phosphate (Ro 64-0802), a pharmacologically active form of oseltamivir, by active efflux across the blood-brain barrier mediated by organic anion transporter 3 (Oat3/Slc22a8) and multidrug resistanceassociated protein 4 (Mrp4/Abcc4). Drug Metab Disposit 37(2):315-321
31. Ose A, Kusuhara H, Yamatsugu K, Kanai M, Shibasaki M, Fujita T, Yamamoto A, Sugiyama Y. (2008). P-glycoprotein restricts the penetration of oseltamivir across the blood-brain barrier. Drug Metab Disposit 36(2):427-434
32. Peters AH, Mermoud JE, O'Carroll D, Pagani M, Schweizer D, Brockdorff N, Jenuwein T. (2002). Histone H3 lysine 9 methylation is an epigenetic imprint of facultative heterochromatin. Nat Genet 30(1):77-80.
33. Razin A. (1998). CpG methylation, chromatin structure and gene silencing - a three-way connection. EMBO J 17(17):4905-4908
34. Sanghani SP, Quinney SK, Fredenburg TB, Davis WI, Murry DJ, Bosron WF. (2004). Hydrolysis of irinotecan and its oxidative metabolites, 7-ethyl-10-[4-N-(5-aminopentanoic acid)-1-piperidino] carbonyloxycamptothecin and 7-ethyl-10-[4-(1-piperidino)-1-amino]-carbonyloxycamptothecin, by human carboxylesterases CES1A1, CES2, and a newly expressed carboxylesterase isoenzyme, CES3. Drug Metab Disposit 32(5):505-511
35. Satoh T, Hosokawa M. (2006). Structure, function and regulation of carboxylesterases. Chemico-Biol Interact 162(3):195-211.
36. Satoh T, Taylor P, Bosron WF, Sanghani SP, Hosokawa M, La Du BN. (2002). Current progress on esterases: from molecular structure to function. Drug Metab Disposit 30(5):488-493
37. Saxonov S, Berg P, Brutlag DL. (2006). A genome-wide analysis of CpG dinucleotides in the human genome distinguishes two distinct classes of promoters. Proc Natl Acad Sci USA 103(5):1412-1417
38. Shi D, Yang J, Yang D, LeCluyse EL, Black C, You L, Akhlaghi F, Yan B. (2006). Anti-influenza prodrug oseltamivir is activated by carboxylesterase human carboxylesterase 1, and the activation is inhibited by antiplatelet agent clopidogrel. J Pharmacol Exp Ther 319(3):1477-1484
39. Tanimoto K, Kaneyasu M, Shimokuni T, Hiyama K, Nishiyama M. (2007). Human carboxylesterase 1A2 expressed from carboxylesterase 1A1 and 1A2 genes is a potent predictor of CPT-11 cytotoxicity in vitro. Pharmacogenet Genom 17(1):1-10.
40. Yang D, Pearce RE, Wang X, Gaedigk R, Wan YJ, Yan B. (2009). Human carboxylesterases HCE1 and HCE2: ontogenic expression, interindividual variability and differential hydrolysis of oseltamivir, aspirin, deltamethrin and permethrin. Biochem Pharmacol 77(2):238-247
41. Zegerman P, Canas B, Pappin D, Kouzarides T. (2002). Histone H3 lysine 4 methylation disrupts binding of nucleosome remodeling and deacetylase (NuRD) repressor complex. J Biol Chem 277(14):11621-11624
42. Zehnder D, Bland R, Walker EA, Bradwell AR, Howie AJ, Hewison M, Stewart PM. (1999). Expression of 25-hydroxyvitamin D3-1alpha-hydroxylase in the human kidney. J Am Soc Nephrol 10(12):2465-2473