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Volumn 531, Issue 1-2, 2003, Pages 191-203

Miscoding properties of 1,N6-ethanoadenine, a DNA adduct derived from reaction with the antitumor agent 1,3-bis(2-chloroethyl)-1- nitrosourea

Author keywords

BCNU; Ethano adduct; Etheno adduct; Polymerase; Translesion DNA synthesis

Indexed keywords

1,N6 ETHANOADENINE; ADENINE DERIVATIVE; ANTINEOPLASTIC AGENT; CARMUSTINE; DNA; DNA POLYMERASE; PHOSPHORAMIDIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0344154365     PISSN: 00275107     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.mrfmmm.2003.07.006     Document Type: Conference Paper
Times cited : (30)

References (59)
  • 1
    • 0031469549 scopus 로고    scopus 로고
    • The chloroethylnitrosoureas: Sensitivity and resistance to cancer chemotherapy at the molecular level
    • Ludlum D.B. The chloroethylnitrosoureas: sensitivity and resistance to cancer chemotherapy at the molecular level. Cancer Invest. 15:1997;588-598.
    • (1997) Cancer Invest. , vol.15 , pp. 588-598
    • Ludlum, D.B.1
  • 3
    • 0028075307 scopus 로고
    • The basis for current treatment recommendations for malignant gliomas
    • Fine H.A. The basis for current treatment recommendations for malignant gliomas. J. Neurooncol. 20:1994;111-120.
    • (1994) J. Neurooncol. , vol.20 , pp. 111-120
    • Fine, H.A.1
  • 5
    • 13844323754 scopus 로고
    • Genotoxicity of 1,3-bis(2-chloroethyl)-1-nitrosourea (BCNU)
    • Wiencke J.K., Wiemels J. Genotoxicity of 1,3-bis(2-chloroethyl)-1- nitrosourea (BCNU). Mutat. Res. 339:1995;91-119.
    • (1995) Mutat. Res. , vol.339 , pp. 91-119
    • Wiencke, J.K.1    Wiemels, J.2
  • 6
    • 0026658165 scopus 로고
    • Mutational specificity of 1,3-bis-(2-chloroethyl)-1-nitrosourea in a Chinese hamster ovary cell line
    • Minnick D.T., Veigl M.L., Sedwick W.D. Mutational specificity of 1,3-bis-(2-chloroethyl)-1-nitrosourea in a Chinese hamster ovary cell line. Cancer Res. 52:1992;4688-4695.
    • (1992) Cancer Res. , vol.52 , pp. 4688-4695
    • Minnick, D.T.1    Veigl, M.L.2    Sedwick, W.D.3
  • 8
    • 0025116511 scopus 로고
    • DNA alkylation by the haloethylnitrosoureas: Nature of modifications produced and their enzymatic repair or removal
    • Ludlum D.B. DNA alkylation by the haloethylnitrosoureas: nature of modifications produced and their enzymatic repair or removal. Mutat. Res. 233:1990;117-126.
    • (1990) Mutat. Res. , vol.233 , pp. 117-126
    • Ludlum, D.B.1
  • 9
    • 0031469549 scopus 로고    scopus 로고
    • The chloroethylnitrosoureas: Sensitivity and resistance to cancer chemotherapy at the molecular level
    • Ludlum D.B. The chloroethylnitrosoureas: sensitivity and resistance to cancer chemotherapy at the molecular level. Cancer Invest. 15:1997;588-598.
    • (1997) Cancer Invest. , vol.15 , pp. 588-598
    • Ludlum, D.B.1
  • 10
    • 0023027829 scopus 로고
    • Formation of cyclic adducts in nucleic acids by the haloethylnitrosoureas
    • B. Singer, H. Bartsch (Eds.) IARC Scientific Publications, Lyon, France
    • D.B. Ludlum, Formation of cyclic adducts in nucleic acids by the haloethylnitrosoureas, in: B. Singer, H. Bartsch (Eds.), The Role of Cyclic Nucleic Acid Adducts in Carcinogenesis and Mutagenesis, vol. 70, IARC Scientific Publications, Lyon, France, 1986, pp. 137-146.
    • (1986) The Role of Cyclic Nucleic Acid Adducts in Carcinogenesis and Mutagenesis , vol.70 , pp. 137-146
    • Ludlum, D.B.1
  • 11
    • 0019957212 scopus 로고
    • 1-deoxyguanosinyl]ethane in DNA treated with N,N′-bis(2- chloroethyl)-N-nitrosourea)
    • 1-deoxyguanosinyl]ethane in DNA treated with N,N′-bis(2-chloroethyl)-N-nitrosourea). Cancer Res. 42:1982;3102-3105.
    • (1982) Cancer Res. , vol.42 , pp. 3102-3105
    • Tong, W.P.1    Kirk, M.C.2    Ludlum, D.B.3
  • 12
    • 0019126210 scopus 로고
    • DNA cross-linking and monoadduct repair in nitrosourea-treated human tumor cells
    • Erickson L.C., Laurent G., Sharkey N.A., Kohn K.W. DNA cross-linking and monoadduct repair in nitrosourea-treated human tumor cells. Nature. 288:1980;727-729.
    • (1980) Nature , vol.288 , pp. 727-729
    • Erickson, L.C.1    Laurent, G.2    Sharkey, N.A.3    Kohn, K.W.4
  • 13
    • 0033252613 scopus 로고    scopus 로고
    • Matijasevic, Role of base excision repair in protecting cells from the toxicity of chloroethylnitrosoureas
    • B. Singer, H. Bartsch (Eds.) IARC Scientific Publications, Lyon, France
    • D.B. Ludlum, Q. Li, Z. Matijasevic, Role of base excision repair in protecting cells from the toxicity of chloroethylnitrosoureas, in: B. Singer, H. Bartsch (Eds.), Exocyclic DNA Adducts in Mutagenesis and Carcinogenesis, vol. 150, IARC Scientific Publications, Lyon, France, 1999, pp. 271-278.
    • (1999) Exocyclic DNA Adducts in Mutagenesis and Carcinogenesis , vol.150 , pp. 271-278
    • Ludlum, D.B.1    Li, Q.2    Matijasevic, Z.3
  • 14
    • 0025193008 scopus 로고
    • 2,3-ethanoguanine in DNA after in vitro treatment with the therapeutic agent, N-(2-chloroethyl)-N′-cyclohexyl-N- nitrosourea
    • 2,3-ethanoguanine in DNA after in vitro treatment with the therapeutic agent, N-(2-chloroethyl)-N′-cyclohexyl-N-nitrosourea. Carcinogenesis. 11:1990;223-228.
    • (1990) Carcinogenesis , vol.11 , pp. 223-228
    • Habraken, Y.1    Carter, C.A.2    Kirk, M.C.3    Riordan, J.M.4    Ludlum, D.B.5
  • 15
    • 0000168477 scopus 로고
    • Etheno-bridged nucleotides in structural diagnosis and carcinogenesis
    • Leonard N.J. Etheno-bridged nucleotides in structural diagnosis and carcinogenesis. Biochem. Mol. Biol. Chemtracts. 3:1992;273-297.
    • (1992) Biochem. Mol. Biol. Chemtracts , vol.3 , pp. 273-297
    • Leonard, N.J.1
  • 16
    • 0033258504 scopus 로고    scopus 로고
    • Exocyclic adducts as new risk markers for DNA damage in man
    • B. Singer, H. Bartsch (Eds.) IARC Scientific Publications, Lyon, France
    • H. Bartsch, Exocyclic adducts as new risk markers for DNA damage in man, in: B. Singer, H. Bartsch (Eds.), Exocyclic DNA Adducts in Mutagenesis and Carcinogenesis, vol. 150, IARC Scientific Publications, Lyon, France, 1999, pp. 1-16.
    • (1999) Exocyclic DNA Adducts in Mutagenesis and Carcinogenesis , vol.150 , pp. 1-16
    • Bartsch, H.1
  • 17
    • 0034031990 scopus 로고    scopus 로고
    • Etheno-adduct-forming chemicals: From mutagenicity testing to tumor mutation spectra
    • Barbin A. Etheno-adduct-forming chemicals: from mutagenicity testing to tumor mutation spectra. Mutat. Res. 462:2000;55-69.
    • (2000) Mutat. Res. , vol.462 , pp. 55-69
    • Barbin, A.1
  • 18
    • 0028978050 scopus 로고
    • 4-ethano, and 3-(2-hydroxyethyl) derivatives of 2′-deoxycytidine and their incorporation into oligomeric DNA
    • 4-ethano, and 3-(2-hydroxyethyl) derivatives of 2′-deoxycytidine and their incorporation into oligomeric DNA. Chem. Res. Toxicol. 8:1995;148-156.
    • (1995) Chem. Res. Toxicol. , vol.8 , pp. 148-156
    • Zhang, W.1    Rieger, R.2    Iden, C.3    Johnson, F.4
  • 20
    • 0032569071 scopus 로고    scopus 로고
    • 6-ethano-2′-deoxyadenosine, a metabolic product of 1,3-bis(2-chloroethyl)nitrosourea, and its incorporation into oligomeric DNA
    • 6-ethano-2′-deoxyadenosine, a metabolic product of 1,3-bis(2-chloroethyl)nitrosourea, and its incorporation into oligomeric DNA. J. Org. Chem. 63:1998;4385-4389.
    • (1998) J. Org. Chem. , vol.63 , pp. 4385-4389
    • Maruenda, H.1    Chenna, A.2    Liem, L.K.3    Singer, B.4
  • 21
    • 0036715036 scopus 로고    scopus 로고
    • Structural insights by molecular dynamics simulations into differential repair efficiency for ethano-A versus etheno-A adducts by the human alkylpurine-DNA-N-glycosylase (APNG)
    • Guliaev A.B., Hang B., Singer B. Structural insights by molecular dynamics simulations into differential repair efficiency for ethano-A versus etheno-A adducts by the human alkylpurine-DNA-N-glycosylase (APNG). Nucl. Acid Res. 30:2002;3778-3787.
    • (2002) Nucl. Acid Res. , vol.30 , pp. 3778-3787
    • Guliaev, A.B.1    Hang, B.2    Singer, B.3
  • 23
    • 0033200360 scopus 로고    scopus 로고
    • A plethora of lesion-replicating DNA polymerases
    • Woodgate R. A plethora of lesion-replicating DNA polymerases. Genes Dev. 13:1999;2191-2195.
    • (1999) Genes Dev. , vol.13 , pp. 2191-2195
    • Woodgate, R.1
  • 25
    • 0035850235 scopus 로고    scopus 로고
    • Translesion synthesis by the UmuC family of DNA polymerases
    • Wang Z.-G. Translesion synthesis by the UmuC family of DNA polymerases. Mutat. Res. 486:2001;59-70.
    • (2001) Mutat. Res. , vol.486 , pp. 59-70
    • Wang, Z.-G.1
  • 26
    • 0033538470 scopus 로고    scopus 로고
    • HRAD30 mutations in the variant form of xeroderma pigmentosum
    • Johnson R.E., Kondratick C.M., Prakash S., Prakash L. hRAD30 mutations in the variant form of xeroderma pigmentosum. Science. 285:1999;263-265.
    • (1999) Science , vol.285 , pp. 263-265
    • Johnson, R.E.1    Kondratick, C.M.2    Prakash, S.3    Prakash, L.4
  • 28
    • 0034425754 scopus 로고    scopus 로고
    • Efficient and accurate replication in the presence of 7,8-dihydro-8-oxoguanine by DNA polymerase η
    • Haracska L., Yu S.L., Johnson R.E., Prakash L., Prakash S. Efficient and accurate replication in the presence of 7,8-dihydro-8-oxoguanine by DNA polymerase η Nat. Genet. 25:2000;458-461.
    • (2000) Nat. Genet. , vol.25 , pp. 458-461
    • Haracska, L.1    Yu, S.L.2    Johnson, R.E.3    Prakash, L.4    Prakash, S.5
  • 29
    • 0034738983 scopus 로고    scopus 로고
    • Eukaryotic polymerases ι and ζ act sequentially to bypass DNA lesions
    • Johnson R.E., Washington M.T., Haracska L., Prakash S., Prakash L. Eukaryotic polymerases ι and ζ act sequentially to bypass DNA lesions. Nature. 406:2000;1015-1019.
    • (2000) Nature , vol.406 , pp. 1015-1019
    • Johnson, R.E.1    Washington, M.T.2    Haracska, L.3    Prakash, S.4    Prakash, L.5
  • 32
    • 0034660259 scopus 로고    scopus 로고
    • Mechanisms of accurate translesion synthesis by human DNA polymerase η
    • Masutani C., Kusumoto R., Iwai S., Hanaoka F. Mechanisms of accurate translesion synthesis by human DNA polymerase η EMBO J. 19:2000;3100-3109.
    • (2000) EMBO J. , vol.19 , pp. 3100-3109
    • Masutani, C.1    Kusumoto, R.2    Iwai, S.3    Hanaoka, F.4
  • 35
    • 0037065724 scopus 로고    scopus 로고
    • 4-etheno-C, a potential carcinogenic glycidaldehyde product, miscodes in vitro using mammalian DNA polymerases
    • 4-etheno-C, a potential carcinogenic glycidaldehyde product, miscodes in vitro using mammalian DNA polymerases. Biochemistry. 41:2002;1778-1785.
    • (2002) Biochemistry , vol.41 , pp. 1778-1785
    • Singer, B.1    Medina, M.2    Zhang, Y.3    Wang, Z.4    Guliaev, A.B.5    Hang, B.6
  • 36
    • 0037020269 scopus 로고    scopus 로고
    • Human DNA polymerase kappa bypasses and extends beyond thymine glycols during translesion synthesis in vitro, preferentially incorporating correct nucleotides
    • Fischhaber P.L., Gerlach V.L., Feaver W.J., Hatahet Z., Wallace S.S., Friedberg E.C. Human DNA polymerase kappa bypasses and extends beyond thymine glycols during translesion synthesis in vitro, preferentially incorporating correct nucleotides. J. Biol. Chem. 277:2002;37604-37611.
    • (2002) J. Biol. Chem. , vol.277 , pp. 37604-37611
    • Fischhaber, P.L.1    Gerlach, V.L.2    Feaver, W.J.3    Hatahet, Z.4    Wallace, S.S.5    Friedberg, E.C.6
  • 38
    • 0031431889 scopus 로고    scopus 로고
    • 6-ethenodeoxyadenosine (εA): Formation of εa basepairs and elongation in defined templates
    • 6- ethenodeoxyadenosine (εA): formation of εA basepairs and elongation in defined templates. Carcinogenesis. 18:1997;1609-1615.
    • (1997) Carcinogenesis , vol.18 , pp. 1609-1615
    • Litinski, V.1    Chenna, A.2    Sagi, J.3    Singer, B.4
  • 40
    • 0032100860 scopus 로고    scopus 로고
    • Mammalian base excision repair and DNA polymerase β
    • Wilson S.H. Mammalian base excision repair and DNA polymerase β Mutat. Res. 407:1998;203-215.
    • (1998) Mutat. Res. , vol.407 , pp. 203-215
    • Wilson, S.H.1
  • 41
    • 0034596992 scopus 로고    scopus 로고
    • Misinsertion and bypass of thymine-thymine dimers by human DNA polymerase ι
    • Tissier A., Frank E.G., McDonald J.P., Iwai S., Hanaoka F., Woodgate R. Misinsertion and bypass of thymine-thymine dimers by human DNA polymerase ι EMBO J. 19:2000;5259-5266.
    • (2000) EMBO J. , vol.19 , pp. 5259-5266
    • Tissier, A.1    Frank, E.G.2    McDonald, J.P.3    Iwai, S.4    Hanaoka, F.5    Woodgate, R.6
  • 42
    • 0036920449 scopus 로고    scopus 로고
    • Translesion replication of benzo[a]pyrene and benzo[c]phenanthrene diol epoxide adducts of deoxyadenosine and deoxyguanosine by human DNA polymerase ι
    • Frank E.G., Sayer J.M., Kroth H., Ohashi E., Ohmori H., Jerina D.M., Woodgate R. Translesion replication of benzo[a]pyrene and benzo[c]phenanthrene diol epoxide adducts of deoxyadenosine and deoxyguanosine by human DNA polymerase ι Nucl. Acids Res. 30:2002;5284-5292.
    • (2002) Nucl. Acids Res. , vol.30 , pp. 5284-5292
    • Frank, E.G.1    Sayer, J.M.2    Kroth, H.3    Ohashi, E.4    Ohmori, H.5    Jerina, D.M.6    Woodgate, R.7
  • 43
    • 0033830464 scopus 로고    scopus 로고
    • Preferential incorporation of G opposite template T by the low-fidelity human DNA polymerase ι
    • Zhang Y., Yuan F., Wu X., Wang Z. Preferential incorporation of G opposite template T by the low-fidelity human DNA polymerase ι Mol. Cell. Biol. 20:2000;7099-7108.
    • (2000) Mol. Cell. Biol. , vol.20 , pp. 7099-7108
    • Zhang, Y.1    Yuan, F.2    Wu, X.3    Wang, Z.4
  • 44
    • 0034214838 scopus 로고    scopus 로고
    • Pol ι, a remarkably error-prone human DNA polymerase
    • Tissier A., McDonald J.P., Frank E.G., Woodgate R. Pol ι, a remarkably error-prone human DNA polymerase. Genes Dev. 14:2000;1642-1650.
    • (2000) Genes Dev. , vol.14 , pp. 1642-1650
    • Tissier, A.1    McDonald, J.P.2    Frank, E.G.3    Woodgate, R.4
  • 46
    • 0035355203 scopus 로고    scopus 로고
    • Altered nucleotide misinsertion fidelity associated with pol ι-dependent replication at the end of a DNA template
    • Frank E.G., Tissier A., McDonald J.P., Rapic-Otrin V., Zeng X., Gearhart P.J., Woodgate R. Altered nucleotide misinsertion fidelity associated with pol ι-dependent replication at the end of a DNA template. EMBO J. 20:2001;2914-2922.
    • (2001) EMBO J. , vol.20 , pp. 2914-2922
    • Frank, E.G.1    Tissier, A.2    McDonald, J.P.3    Rapic-Otrin, V.4    Zeng, X.5    Gearhart, P.J.6    Woodgate, R.7
  • 48
    • 0030787013 scopus 로고    scopus 로고
    • What structural features determine repair enzyme specificity and mechanism in chemically modified DNA?
    • Singer B., Hang B. What structural features determine repair enzyme specificity and mechanism in chemically modified DNA? Chem. Res. Toxicol. 10:1997;713-732.
    • (1997) Chem. Res. Toxicol. , vol.10 , pp. 713-732
    • Singer, B.1    Hang, B.2
  • 49
    • 0003670569 scopus 로고    scopus 로고
    • Exocyclic DNA Adducts in Mutagenesis and Carcinogenesis
    • Lyon, France
    • B. Singer, H. Bartsch, Exocyclic DNA Adducts in Mutagenesis and Carcinogenesis, vol. 150, IARC Scientific Publications, Lyon, France, 1999, pp. 361.
    • (1999) IARC Scientific Publications , vol.150 , pp. 361
    • Singer, B.1    Bartsch, H.2
  • 50
    • 0035313218 scopus 로고    scopus 로고
    • Endogenous DNA damage and mutation
    • Marnett L.J., Plastaras J.P. Endogenous DNA damage and mutation. Trends Genet. 17:2001;214-221.
    • (2001) Trends Genet. , vol.17 , pp. 214-221
    • Marnett, L.J.1    Plastaras, J.P.2
  • 51
    • 0037058976 scopus 로고    scopus 로고
    • Role of human DNA polymerase kappa as an extender in translesion synthesis
    • Haracska L., Prakash L., Prakash S. Role of human DNA polymerase kappa as an extender in translesion synthesis. Proc. Natl. Acad. Sci. U.S.A. 99:2002;16000-16005.
    • (2002) Proc. Natl. Acad. Sci. U.S.A. , vol.99 , pp. 16000-16005
    • Haracska, L.1    Prakash, L.2    Prakash, S.3
  • 52
    • 0029665327 scopus 로고    scopus 로고
    • 6-Ethenodeoxyadenosine, a DNA adduct highly mutagenic in mammalian cells
    • 6-Ethenodeoxyadenosine, a DNA adduct highly mutagenic in mammalian cells. Biochemistry. 35:1996;11487-11492.
    • (1996) Biochemistry , vol.35 , pp. 11487-11492
    • Pandya, G.A.1    Moriya, M.2
  • 54
    • 0036529562 scopus 로고    scopus 로고
    • Response of human REV1 to different DNA damage: Preferential dCMP insertion opposite the lesion
    • Zhang Y., Wu X., Rechkoblit O., Geacintov N.E., Taylor J.-S., Wang Z. Response of human REV1 to different DNA damage: preferential dCMP insertion opposite the lesion. Nucl. Acids Res. 30:2002;1630-1638.
    • (2002) Nucl. Acids Res. , vol.30 , pp. 1630-1638
    • Zhang, Y.1    Wu, X.2    Rechkoblit, O.3    Geacintov, N.E.4    Taylor, J.-S.5    Wang, Z.6
  • 55
    • 0030930760 scopus 로고    scopus 로고
    • Crystal structures of human DNA polymerase β complexed with gapped and nicked DNA: Evidence for an induced fit mechanism
    • Sawaya M.R., Prasad R., Wilson S.H., Kraut J., Pelletier H. Crystal structures of human DNA polymerase β complexed with gapped and nicked DNA: evidence for an induced fit mechanism. Biochemistry. 36:1997;11205-11215.
    • (1997) Biochemistry , vol.36 , pp. 11205-11215
    • Sawaya, M.R.1    Prasad, R.2    Wilson, S.H.3    Kraut, J.4    Pelletier, H.5
  • 56
    • 0032005866 scopus 로고    scopus 로고
    • Structural and functional insights provided by crystal structures of DNA polymerases and their substrate complexes
    • Brautigam C.A., Steitz T.A. Structural and functional insights provided by crystal structures of DNA polymerases and their substrate complexes. Curr. Opin. Struct. Biol. 8:1998;54-63.
    • (1998) Curr. Opin. Struct. Biol. , vol.8 , pp. 54-63
    • Brautigam, C.A.1    Steitz, T.A.2
  • 57
    • 0037227566 scopus 로고    scopus 로고
    • Structure of DNA polymerase β with the mutagenic DNA lesion 8-oxodeoxyguanine reveals structural insights into its coding potential
    • Krahn J.M., Beard W.A., Miller H., Grollman A.P., Wilson S.H. Structure of DNA polymerase β with the mutagenic DNA lesion 8-oxodeoxyguanine reveals structural insights into its coding potential. Structure (Camb.). 11:2003;121-127.
    • (2003) Structure (Camb.) , vol.11 , pp. 121-127
    • Krahn, J.M.1    Beard, W.A.2    Miller, H.3    Grollman, A.P.4    Wilson, S.H.5
  • 58
    • 0034847259 scopus 로고    scopus 로고
    • Structure of the catalytic core of S. cerevisiae DNA polymerase η: Implications for translesion DNA synthesis
    • Trincao J., Johnson R.E., Escalante C.R., Prakash S., Prakash L., Aggarwal A.K. Structure of the catalytic core of S. cerevisiae DNA polymerase η: implications for translesion DNA synthesis. Mol. Cell. 8:2001;417-426.
    • (2001) Mol. Cell , vol.8 , pp. 417-426
    • Trincao, J.1    Johnson, R.E.2    Escalante, C.R.3    Prakash, S.4    Prakash, L.5    Aggarwal, A.K.6
  • 59
    • 0035812849 scopus 로고    scopus 로고
    • Crystal structure of a Y family DNA polymerase in action: A mechanism for error-prone and lesion-bypass replication
    • Ling H., Boudsocq F., Woodgate R., Yang W. Crystal structure of a Y family DNA polymerase in action: a mechanism for error-prone and lesion-bypass replication. Cell. 107:2001;91-102.
    • (2001) Cell , vol.107 , pp. 91-102
    • Ling, H.1    Boudsocq, F.2    Woodgate, R.3    Yang, W.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.