메뉴 건너뛰기




Volumn 30, Issue 5, 2009, Pages 886-893

Incorporation of 5-chlorocytosine into mammalian DNA results in heritable gene silencing and altered cytosine methylation patterns

Author keywords

[No Author keywords available]

Indexed keywords

5 AZA 2' DEOXYCYTIDINE; 5 CHLOROCYTOSINE; 5 METHYLCYTOSINE; 5 METHYLDEOXYCYTIDINE; 5' CHLORO 2' DEOXYCYTIDINE 5' TRIPHOSPHATE; DEOXYCYTIDINE TRIPHOSPHATE; HYPOXANTHINE PHOSPHORIBOSYLTRANSFERASE; METHYL 2' DEOXYCYTIDINE 5' TRIPHOSPHATE; PYRIMIDINE NUCLEOSIDE; TIOGUANINE; UNCLASSIFIED DRUG;

EID: 65549089202     PISSN: 01433334     EISSN: 14602180     Source Type: Journal    
DOI: 10.1093/carcin/bgp060     Document Type: Article
Times cited : (41)

References (47)
  • 1
    • 1042278765 scopus 로고    scopus 로고
    • The history of cancer epigenetics
    • Feinberg,A.P. et al. (2004) The history of cancer epigenetics. Nat. Rev. Cancer, 4, 143-153.
    • (2004) Nat. Rev. Cancer , vol.4 , pp. 143-153
    • Feinberg, A.P.1
  • 2
    • 13844320649 scopus 로고    scopus 로고
    • Aberrant DNA methylation as a cancer-inducing mechanism
    • Esteller,M. (2005) Aberrant DNA methylation as a cancer-inducing mechanism. Annu. Rev. Pharmacol. Toxicol., 45, 629-656.
    • (2005) Annu. Rev. Pharmacol. Toxicol , vol.45 , pp. 629-656
    • Esteller, M.1
  • 3
    • 32344450824 scopus 로고    scopus 로고
    • Genomic DNA methylation: The mark and its mediators
    • Klose,R.J. et al. (2006) Genomic DNA methylation: The mark and its mediators. Trends Biochem. Sci., 31, 89-97.
    • (2006) Trends Biochem. Sci , vol.31 , pp. 89-97
    • Klose, R.J.1
  • 4
    • 36549056015 scopus 로고    scopus 로고
    • Epigenetic changes in cancer
    • Grønbaek,K. et al. (2007) Epigenetic changes in cancer. APMIS 115, 1039-1059.
    • (2007) APMIS , vol.115 , pp. 1039-1059
    • Grønbaek, K.1
  • 5
    • 0345357773 scopus 로고    scopus 로고
    • Gene silencing in cancer in association with promoter hypermethylation
    • Herman,J.G. et al. (2003) Gene silencing in cancer in association with promoter hypermethylation. N. Engl. J. Med., 349, 2042-2054.
    • (2003) N. Engl. J. Med , vol.349 , pp. 2042-2054
    • Herman, J.G.1
  • 6
    • 0020627846 scopus 로고
    • Hypomethylation of ras oncogenes in primary human cancers
    • Feinberg,A.P. et al. (1983) Hypomethylation of ras oncogenes in primary human cancers. Biochem. Biophys. Res. Commun., 111, 47-54.
    • (1983) Biochem. Biophys. Res. Commun , vol.111 , pp. 47-54
    • Feinberg, A.P.1
  • 7
    • 0036324032 scopus 로고    scopus 로고
    • DNA hypomethylation, cancer, the immunodeficiency, centromeric region instability, facial anomalies syndrome and chromosomal rearrangements
    • Ehrlich,M. (2002) DNA hypomethylation, cancer, the immunodeficiency, centromeric region instability, facial anomalies syndrome and chromosomal rearrangements. J. Nutr., 132, 2424S-2429S.
    • (2002) J. Nutr , vol.132
    • Ehrlich, M.1
  • 8
    • 65549128774 scopus 로고    scopus 로고
    • Office of Portfolio Analysis and Strategic Initiatives National Institutes of Health [homepage on the internet]. NIH Roadmap for Medical Research. http://nihroadmap.nih.gov/epigenomics/ (18 April 2008, date last accessed).
    • Office of Portfolio Analysis and Strategic Initiatives National Institutes of Health [homepage on the internet]. NIH Roadmap for Medical Research. http://nihroadmap.nih.gov/epigenomics/ (18 April 2008, date last accessed).
  • 9
    • 0029073020 scopus 로고
    • The causes and prevention of cancer
    • Ames,B.N. et al. (1995) The causes and prevention of cancer. Proc. Natl Acad. Sci. USA, 92, 5258-5265.
    • (1995) Proc. Natl Acad. Sci. USA , vol.92 , pp. 5258-5265
    • Ames, B.N.1
  • 10
    • 0034011261 scopus 로고    scopus 로고
    • Oxyradicals and DNA damage
    • Marnett,L.J. (2000) Oxyradicals and DNA damage. Carcinogenesis, 21, 361-370.
    • (2000) Carcinogenesis , vol.21 , pp. 361-370
    • Marnett, L.J.1
  • 11
    • 0037372157 scopus 로고    scopus 로고
    • 3-Chlorotyrosine as a marker of protein damage by myeloperoxidase in tracheal aspirates from preterm infants: Association with adverse respiratory outcome
    • Buss,I.H. et al. (2003) 3-Chlorotyrosine as a marker of protein damage by myeloperoxidase in tracheal aspirates from preterm infants: association with adverse respiratory outcome. Pediatr. Res., 53 455-462.
    • (2003) Pediatr. Res , vol.53 , pp. 455-462
    • Buss, I.H.1
  • 12
    • 0035834065 scopus 로고    scopus 로고
    • Neutrophils employ the myeloperoxidase system to generate antimicrobial brominating and chlorinating oxidants during sepsis
    • Gaut,J.P. et al. (2001) Neutrophils employ the myeloperoxidase system to generate antimicrobial brominating and chlorinating oxidants during sepsis. Proc. Natl Acad. Sci. USA, 98, 11961-11966.
    • (2001) Proc. Natl Acad. Sci. USA , vol.98 , pp. 11961-11966
    • Gaut, J.P.1
  • 13
    • 0032880537 scopus 로고    scopus 로고
    • Oxidative damage to proteins of bronchoalveolar lavage fluid in patients with acute respiratory distress syndrome: Evidence for neutrophil-mediated hydroxylation, nitration, and chlorination
    • Lamb,N.J. et al. (1999) Oxidative damage to proteins of bronchoalveolar lavage fluid in patients with acute respiratory distress syndrome: Evidence for neutrophil-mediated hydroxylation, nitration, and chlorination. Crit. Care Med., 27, 1738-1744.
    • (1999) Crit. Care Med , vol.27 , pp. 1738-1744
    • Lamb, N.J.1
  • 14
    • 47049119999 scopus 로고    scopus 로고
    • Kang,J.I.Jr et al. (2008) Examination of hypochlorous acid-induced damage to cytosine residues in a CpG dinucleotide in DNA. Chem. Res. Toxicol., 6, 1211-1218.
    • Kang,J.I.Jr et al. (2008) Examination of hypochlorous acid-induced damage to cytosine residues in a CpG dinucleotide in DNA. Chem. Res. Toxicol., 6, 1211-1218.
  • 15
    • 27644541401 scopus 로고    scopus 로고
    • Detection of chlorinated DNA and RNA nucleosides by HPLC coupled to tandem mass spectrometry as potential biomarkers of inflammation
    • Badouard,C. et al. (2005) Detection of chlorinated DNA and RNA nucleosides by HPLC coupled to tandem mass spectrometry as potential biomarkers of inflammation. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci., 827, 26-31.
    • (2005) J. Chromatogr. B Analyt. Technol. Biomed. Life Sci , vol.827 , pp. 26-31
    • Badouard, C.1
  • 16
    • 0030777056 scopus 로고    scopus 로고
    • Hypochlorous acid-induced base modifications in isolated calf thymus DNA
    • Whiteman,M. et al. (1997) Hypochlorous acid-induced base modifications in isolated calf thymus DNA. Chem. Res. Toxicol., 10, 1240-1246.
    • (1997) Chem. Res. Toxicol , vol.10 , pp. 1240-1246
    • Whiteman, M.1
  • 17
    • 20044370689 scopus 로고    scopus 로고
    • 5-Halogenated pyrimidine lesions within a CpG sequence context mimic 5-methylcytosine by enhancing the binding of the methyl-CpG-binding domain of methyl-CpG-binding protein 2 (MeCP2)
    • Valinluck,V. et al. (2005) 5-Halogenated pyrimidine lesions within a CpG sequence context mimic 5-methylcytosine by enhancing the binding of the methyl-CpG-binding domain of methyl-CpG-binding protein 2 (MeCP2). Nucleic Acids Res., 33, 3057-3064.
    • (2005) Nucleic Acids Res , vol.33 , pp. 3057-3064
    • Valinluck, V.1
  • 18
    • 33847055935 scopus 로고    scopus 로고
    • Endogenous cytosine damage products alter the site selectivity of human DNA maintenance methyltransferase DNMT1
    • Valinluck,V. et al. (2007) Endogenous cytosine damage products alter the site selectivity of human DNA maintenance methyltransferase DNMT1. Cancer Res., 67, 946-950.
    • (2007) Cancer Res , vol.67 , pp. 946-950
    • Valinluck, V.1
  • 19
    • 0021182490 scopus 로고
    • 5-Methyl-2′-deoxycytidine. Metabolism and effects on cell lethality studied with human leukemic cells in vitro
    • Jekunen,A. et al. (1983) 5-Methyl-2′-deoxycytidine. Metabolism and effects on cell lethality studied with human leukemic cells in vitro. Mol. Pharmacol., 25, 431-435.
    • (1983) Mol. Pharmacol , vol.25 , pp. 431-435
    • Jekunen, A.1
  • 20
    • 0020558057 scopus 로고
    • Exclusion of exogenous 5-methyl-2′-deoxycytidine from DNA in human leukemic cells. A study with [2(-14)C]- and [methyl-14C]5-methyl-2′-deoxycytidine
    • Jekunen,A. et al. (1983) Exclusion of exogenous 5-methyl-2′-deoxycytidine from DNA in human leukemic cells. A study with [2(-14)C]- and [methyl-14C]5-methyl-2′-deoxycytidine. Biochem. Pharmacol., 32, 1165-1168.
    • (1983) Biochem. Pharmacol , vol.32 , pp. 1165-1168
    • Jekunen, A.1
  • 21
    • 0027536698 scopus 로고
    • Direct induction of DNA hypermethylation in sea urchin embryos by microinjection of 5-methyl dCTP stimulates early histone gene expression and leads to developmental arrest
    • Chen,J. et al. (1993) Direct induction of DNA hypermethylation in sea urchin embryos by microinjection of 5-methyl dCTP stimulates early histone gene expression and leads to developmental arrest. Dev. Biol. 155, 75-86.
    • (1993) Dev. Biol , vol.155 , pp. 75-86
    • Chen, J.1
  • 22
    • 0026316996 scopus 로고
    • Gene silencing in mammalian cells by direct incorporation of electroporated 5-methyl-2′-deoxycytidine 5′-triphosphate
    • Nyce,J. (1991) Gene silencing in mammalian cells by direct incorporation of electroporated 5-methyl-2′-deoxycytidine 5′-triphosphate. Somat. Cell Mol. Genet., 17, 543-550.
    • (1991) Somat. Cell Mol. Genet , vol.17 , pp. 543-550
    • Nyce, J.1
  • 23
    • 0026332115 scopus 로고
    • Gene silencing in mammalian cells by uptake of 5-methyl deoxycytidine-5′-triphosphate
    • Holliday,R. et al. (1991) Gene silencing in mammalian cells by uptake of 5-methyl deoxycytidine-5′-triphosphate. Somat. Cell Mol. Genet., 17, 537-542.
    • (1991) Somat. Cell Mol. Genet , vol.17 , pp. 537-542
    • Holliday, R.1
  • 24
    • 0036315387 scopus 로고    scopus 로고
    • DNA methylation and epigenetic inheritance
    • Holliday,R. et al. (2002) DNA methylation and epigenetic inheritance. Methods, 27, 179-183.
    • (2002) Methods , vol.27 , pp. 179-183
    • Holliday, R.1
  • 25
    • 4644247467 scopus 로고    scopus 로고
    • Kang,J.I.Jr et al. (2004) Synthesis and characterization of oligonucleotides containing 5-chlorocytosine. Chem. Res. Toxicol., 17, 1236-1244.
    • Kang,J.I.Jr et al. (2004) Synthesis and characterization of oligonucleotides containing 5-chlorocytosine. Chem. Res. Toxicol., 17, 1236-1244.
  • 26
    • 0019760168 scopus 로고
    • A new route to nucleoside 5′-triphosphates
    • Ludwig,J. (1981) A new route to nucleoside 5′-triphosphates. Acta Biochim. Biophys. Acad. Sci. Hung., 16, 131-133.
    • (1981) Acta Biochim. Biophys. Acad. Sci. Hung , vol.16 , pp. 131-133
    • Ludwig, J.1
  • 27
    • 0037106658 scopus 로고    scopus 로고
    • Synthesis of stable-isotope enriched 5-methylpyrimidines and their use as probes of base reactivity in DNA
    • Burdzy,A. et al. (2002) Synthesis of stable-isotope enriched 5-methylpyrimidines and their use as probes of base reactivity in DNA. Nucleic Acids Res., 18, 4068-4074.
    • (2002) Nucleic Acids Res , vol.18 , pp. 4068-4074
    • Burdzy, A.1
  • 28
    • 65549143333 scopus 로고
    • Studies on thymine-5-bromouracil "exchange" in deoxyribonucleic acids of Escherichia coli
    • Zamenhof,S. et al. (1959) Studies on thymine-5-bromouracil "exchange" in deoxyribonucleic acids of Escherichia coli. J. Biol. Chem., 234, 2960-2964.
    • (1959) J. Biol. Chem , vol.234 , pp. 2960-2964
    • Zamenhof, S.1
  • 29
    • 0014425358 scopus 로고
    • Efficiency of utilization of thymine and 5-bromouracil for normal and repair DNA synthesis in bacteria
    • Kanner,L. et al. (1968) Efficiency of utilization of thymine and 5-bromouracil for normal and repair DNA synthesis in bacteria. Biochim. Biophys. Acta, 157, 532-545.
    • (1968) Biochim. Biophys. Acta , vol.157 , pp. 532-545
    • Kanner, L.1
  • 30
    • 33646107882 scopus 로고    scopus 로고
    • Impact of cytosine 5-halogens on the interaction of DNA with restriction endonucleases and methyltransferase
    • Valinluck,V. et al. (2006) Impact of cytosine 5-halogens on the interaction of DNA with restriction endonucleases and methyltransferase. Chem. Res. Toxicol., 19, 556-562.
    • (2006) Chem. Res. Toxicol , vol.19 , pp. 556-562
    • Valinluck, V.1
  • 31
    • 0020032366 scopus 로고
    • Inhibition of DNA methyltransferase and induction of Friend erythroleukemia cell differentiation by 5-azacytidine and 5-aza-2′-deoxycytidine
    • Creusot,F. et al. (1982) Inhibition of DNA methyltransferase and induction of Friend erythroleukemia cell differentiation by 5-azacytidine and 5-aza-2′-deoxycytidine. J. Biol. Chem., 257 2041-2048.
    • (1982) J. Biol. Chem , vol.257 , pp. 2041-2048
    • Creusot, F.1
  • 32
    • 0020308438 scopus 로고
    • Mechanism of action of eukaryotic DNA methyltransferase. Use of 5-azacytosine-containing DNA
    • Taylor,S.M. et al. (1982) Mechanism of action of eukaryotic DNA methyltransferase. Use of 5-azacytosine-containing DNA. J. Mol. Biol. 162, 679-692.
    • (1982) J. Mol. Biol , vol.162 , pp. 679-692
    • Taylor, S.M.1
  • 33
    • 4043112183 scopus 로고    scopus 로고
    • Oxidative damage to methyl-CpG sequences inhibits the binding of the methyl-CpG binding domain (MBD) of MeCP2
    • Valinluck,V. et al. (2004) Oxidative damage to methyl-CpG sequences inhibits the binding of the methyl-CpG binding domain (MBD) of MeCP2. Nucleic Acids Res., 32, 4100-4108.
    • (2004) Nucleic Acids Res , vol.32 , pp. 4100-4108
    • Valinluck, V.1
  • 34
    • 0027495467 scopus 로고
    • Dissection of the methyl-CpG binding domain from the chromosomal protein MeCP2
    • Nan,X. et al. (1993) Dissection of the methyl-CpG binding domain from the chromosomal protein MeCP2. Nucleic Acids Res., 21, 4886-4892.
    • (1993) Nucleic Acids Res , vol.21 , pp. 4886-4892
    • Nan, X.1
  • 35
    • 0035793540 scopus 로고    scopus 로고
    • DNA recognition by the methyl-CpG binding domain of MeCP2
    • Free,A. et al. (2001) DNA recognition by the methyl-CpG binding domain of MeCP2. J. Biol. Chem., 276, 3353-3360.
    • (2001) J. Biol. Chem , vol.276 , pp. 3353-3360
    • Free, A.1
  • 36
    • 0033584939 scopus 로고    scopus 로고
    • Molecular chlorine generated by the myeloperoxidase-hydrogen peroxide-chloride system of phagocytes produces 5-chlorocytosine in bacterial RNA
    • Henderson,J.P. et al. (1999) Molecular chlorine generated by the myeloperoxidase-hydrogen peroxide-chloride system of phagocytes produces 5-chlorocytosine in bacterial RNA. J. Biol. Chem., 274, 33440-33448.
    • (1999) J. Biol. Chem , vol.274 , pp. 33440-33448
    • Henderson, J.P.1
  • 37
    • 0035896545 scopus 로고    scopus 로고
    • Production of brominating intermediates by myeloperoxidase. A transhalogenation pathway for generating mutagenic nucleobases during inflammation
    • Henderson,J.P. et al. (2001) Production of brominating intermediates by myeloperoxidase. A transhalogenation pathway for generating mutagenic nucleobases during inflammation. J. Biol. Chem. 276, 7867-7875.
    • (2001) J. Biol. Chem , vol.276 , pp. 7867-7875
    • Henderson, J.P.1
  • 38
    • 0033551167 scopus 로고    scopus 로고
    • Hypochlorous acid-induced base modification: PotenBiation by nitrite: biomarkers of DNA damage by reactive oxygen species
    • Whiteman,M. et al. (1999) Hypochlorous acid-induced base modification: PotenBiation by nitrite: biomarkers of DNA damage by reactive oxygen species. Biochem. Biophys. Res. Commun., 257 572-576.
    • (1999) Biochem. Biophys. Res. Commun , vol.257 , pp. 572-576
    • Whiteman, M.1
  • 39
    • 0017240322 scopus 로고
    • Studies on the chlorinating activity of myeloperoxidase
    • Harrison,J.E. et al. (1976) Studies on the chlorinating activity of myeloperoxidase. J. Biol. Chem., 251, 1371-1374.
    • (1976) J. Biol. Chem , vol.251 , pp. 1371-1374
    • Harrison, J.E.1
  • 40
    • 0020702109 scopus 로고
    • Assessment of chlorination by human neutrophils
    • Foote,C.S. et al. (1983) Assessment of chlorination by human neutrophils. Nature, 301, 715-716.
    • (1983) Nature , vol.301 , pp. 715-716
    • Foote, C.S.1
  • 41
    • 0030046117 scopus 로고    scopus 로고
    • Neutrophils convert tyrosyl residues in albumin to chlorotyrosine
    • Kettle,A.J. (1996) Neutrophils convert tyrosyl residues in albumin to chlorotyrosine. FEBS Lett., 379, 103-106.
    • (1996) FEBS Lett , vol.379 , pp. 103-106
    • Kettle, A.J.1
  • 42
    • 18244390487 scopus 로고    scopus 로고
    • Myeloperoxidase: Friend and foe
    • Klebanoff,S.J. (2005) Myeloperoxidase: Friend and foe. J. Leukoc. Biol., 77, 598-625.
    • (2005) J. Leukoc. Biol , vol.77 , pp. 598-625
    • Klebanoff, S.J.1
  • 43
    • 33847082795 scopus 로고    scopus 로고
    • Secretion and inactivation of myeloperoxidase by isolated neutrophils
    • King,C.C. et al. (2002) Secretion and inactivation of myeloperoxidase by isolated neutrophils. J. Leukoc. Biol., 61 239-302.
    • (2002) J. Leukoc. Biol , vol.61 , pp. 239-302
    • King, C.C.1
  • 44
    • 0029001483 scopus 로고
    • DNA adduct 8-hydroxyl-2′-deoxyguanosine (8-hydroxyguanine) affects function of human DNA methyltransferase
    • Turk,P.W. et al. (1995) DNA adduct 8-hydroxyl-2′-deoxyguanosine (8-hydroxyguanine) affects function of human DNA methyltransferase. Carcinogenesis, 16, 1253-1255.
    • (1995) Carcinogenesis , vol.16 , pp. 1253-1255
    • Turk, P.W.1
  • 45
    • 0032722062 scopus 로고    scopus 로고
    • Pradhan,S. et al. (1999) Recombinant human DNA (cytosine-5) methyltransferase. I. Expression, purification, and comparison of de novo and maintenance methylation. J. Biol. Chem., 274, 33002-33010.
    • Pradhan,S. et al. (1999) Recombinant human DNA (cytosine-5) methyltransferase. I. Expression, purification, and comparison of de novo and maintenance methylation. J. Biol. Chem., 274, 33002-33010.
  • 46
    • 0032731355 scopus 로고    scopus 로고
    • Recombinant human DNA (cytosine-5) methyltransferase. II. Steady-state kinetics reveal allosteric activation by methylated dna
    • Bacolla,A. et al. (1999) Recombinant human DNA (cytosine-5) methyltransferase. II. Steady-state kinetics reveal allosteric activation by methylated dna. J. Biol. Chem., 274, 33011-33019.
    • (1999) J. Biol. Chem , vol.274 , pp. 33011-33019
    • Bacolla, A.1
  • 47
    • 38449113853 scopus 로고    scopus 로고
    • DNA methylation analysis by pyrosequencing
    • Tost,J. et al. (2007) DNA methylation analysis by pyrosequencing. Nat. Protoc., 2, 2265-2275.
    • (2007) Nat. Protoc , vol.2 , pp. 2265-2275
    • Tost, J.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.