메뉴 건너뛰기




Volumn 34, Issue 16, 2006, Pages 4458-4466

A modified thymine for the synthesis of site-specific thymine-guanine DNA interstrand crosslinks

Author keywords

[No Author keywords available]

Indexed keywords

3 (2 CHLOROETHYL)THYMIDINE; DNA; ETHYLENE; GUANINE; OLIGONUCLEOTIDE; THYMIDINE DERIVATIVE; THYMINE; UNCLASSIFIED DRUG;

EID: 33750013230     PISSN: 03051048     EISSN: 13624962     Source Type: Journal    
DOI: 10.1093/nar/gkl587     Document Type: Article
Times cited : (21)

References (39)
  • 1
    • 33644623520 scopus 로고    scopus 로고
    • Formation and repair of interstrand cross-links in DNA
    • Noll,D.M., Mason,T.M. and Miller,P.S. (2006) Formation and repair of interstrand cross-links in DNA. Chem. Rev., 106, 277-301.
    • (2006) Chem. Rev. , vol.106 , pp. 277-301
    • Noll, D.M.1    Mason, T.M.2    Miller, P.S.3
  • 2
    • 12344282013 scopus 로고    scopus 로고
    • DNA interstrand crosslinks: Natural and drug-induced DNA adducts that induce unique cellular responses
    • Schärer,O.D. (2005) DNA interstrand crosslinks: Natural and drug-induced DNA adducts that induce unique cellular responses. ChemBioChem., 6, 27-32.
    • (2005) Chem Bio Chem. , vol.6 , pp. 27-32
    • Schärer, O.D.1
  • 3
    • 0035379611 scopus 로고    scopus 로고
    • The emerging genetic and molecular basis of Fanconi anaemia
    • Joenje,H. and Patel,K.J. (2001) The emerging genetic and molecular basis of Fanconi anaemia. Nat. Rev. Genet., 2, 446-457.
    • (2001) Nat. Rev. Genet. , vol.2 , pp. 446-457
    • Joenje, H.1    Patel, K.J.2
  • 4
    • 0037268338 scopus 로고    scopus 로고
    • The Fanconi anaemia/BRCA pathway
    • D'Andrea,A.D. and Grompe,M. (2003) The Fanconi anaemia/BRCA pathway. Nat. Rev. Cancer, 3, 23-34.
    • (2003) Nat. Rev. Cancer , vol.3 , pp. 23-34
    • D'Andrea, A.D.1    Grompe, M.2
  • 5
    • 0035436539 scopus 로고    scopus 로고
    • Repair of DNA interstrand crosslinks: Molecular mechanisms and clinical relevance
    • McHugh,P.J., Spanswick,V.J. and Hartley,J.A. (2001) Repair of DNA interstrand crosslinks: Molecular mechanisms and clinical relevance. Lancet Oncol., 2, 483-490.
    • (2001) Lancet Oncol. , vol.2 , pp. 483-490
    • McHugh, P.J.1    Spanswick, V.J.2    Hartley, J.A.3
  • 7
    • 0042872991 scopus 로고    scopus 로고
    • Chemistry and biology of DNA repair
    • Schärer,O.D. (2003) Chemistry and biology of DNA repair. Angew. Chem. Int. Ed. Engl., 42, 2946-2974.
    • (2003) Angew. Chem. Int. Ed. Engl. , vol.42 , pp. 2946-2974
    • Schärer, O.D.1
  • 9
    • 0035807079 scopus 로고    scopus 로고
    • Repair of DNA interstrand cross-links
    • Dronkert,M.L. and Kanaar,R. (2001) Repair of DNA interstrand cross-links. Mutat. Res., 486, 217-247.
    • (2001) Mutat. Res. , vol.486 , pp. 217-247
    • Dronkert, M.L.1    Kanaar, R.2
  • 10
    • 2542455633 scopus 로고    scopus 로고
    • Preparation of interstrand cross-linked DNA oligonucleotide duplexes
    • Noll,D.M., Noronha,A.M., Wilds,C.J. and Miller,P.S. (2004) Preparation of interstrand cross-linked DNA oligonucleotide duplexes. Front. Biosci., 9, 421-437.
    • (2004) Front. Biosci. , vol.9 , pp. 421-437
    • Noll, D.M.1    Noronha, A.M.2    Wilds, C.J.3    Miller, P.S.4
  • 11
    • 0024355567 scopus 로고
    • Synthesis of a duplex oligonucleotide containing a nitrogen mustard interstrand DNA-DNA cross-link
    • Ojwang,J.O., Grueneberg,D.A. and Loechler,E.L. (1989) Synthesis of a duplex oligonucleotide containing a nitrogen mustard interstrand DNA-DNA cross-link. Cancer Res., 49, 6529-6537.
    • (1989) Cancer Res. , vol.49 , pp. 6529-6537
    • Ojwang, J.O.1    Grueneberg, D.A.2    Loechler, E.L.3
  • 12
    • 0027159566 scopus 로고
    • Covalent structure of a nitrogen mustard-induced DNA interstrand cross-link: An N7-to-N7-linkage of deoxyguanosine residues at the duplex sequence 5′-d(GNC)
    • Rink,S.M., Solomon,M.S., Taylor,M.J., Rjur,S., McLaughlin,L.W. and Hopkins,P.B. (1993) Covalent structure of a nitrogen mustard-induced DNA interstrand cross-link: An N7-to-N7-linkage of deoxyguanosine residues at the duplex sequence 5′-d(GNC). J. Am. Chem. Soc., 115, 2551-2557.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 2551-2557
    • Rink, S.M.1    Solomon, M.S.2    Taylor, M.J.3    Rjur, S.4    McLaughlin, L.W.5    Hopkins, P.B.6
  • 13
    • 0029966782 scopus 로고    scopus 로고
    • Synthesis and structural characterization of the N2G-mitomycin C-N2G interstrand cross-link in a model synthetic 23 base pair oligonucleotide DNA duplex
    • Warren,A.J. and Hamilton,J.W. (1996) Synthesis and structural characterization of the N2G-mitomycin C-N2G interstrand cross-link in a model synthetic 23 base pair oligonucleotide DNA duplex. Chem. Res. Toxicol., 9, 1063-1071.
    • (1996) Chem. Res. Toxicol. , vol.9 , pp. 1063-1071
    • Warren, A.J.1    Hamilton, J.W.2
  • 14
    • 0033199891 scopus 로고    scopus 로고
    • Direct demonstration in synthetic oligonucleotides that N,N′-bis(2-chloroethyl)-nitrosourea cross links N1 of deoxyguanosine to N3 of deoxycytidine on opposite strands of duplex DNA
    • Fischhaber,P.L., Gall,A.S., Duncan,J.A. and Hopkins,P.B. (1999) Direct demonstration in synthetic oligonucleotides that N,N′-bis(2-chloroethyl)-nitrosourea cross links N1 of deoxyguanosine to N3 of deoxycytidine on opposite strands of duplex DNA. Cancer Res., 59, 4363-4368.
    • (1999) Cancer Res. , vol.59 , pp. 4363-4368
    • Fischhaber, P.L.1    Gall, A.S.2    Duncan, J.A.3    Hopkins, P.B.4
  • 15
    • 0029798674 scopus 로고
    • Deoxyadenosine and thymidine bases held proximal and distal by means of a covalently-linked dimensional analogue of dA·dT: Intramolecular vs intermolcular hydrogen bonding
    • Bhat,B., Leonard,N.J., Robinson,H. and Wang,A.H.-J. (1986) Deoxyadenosine and thymidine bases held proximal and distal by means of a covalently-linked dimensional analogue of dA·dT: Intramolecular vs intermolcular hydrogen bonding. J. Amer. Chem. Soc., 118, 10744-10751.
    • (1986) J. Amer. Chem. Soc. , vol.118 , pp. 10744-10751
    • Bhat, B.1    Leonard, N.J.2    Robinson, H.3    Wang, A.H.-J.4
  • 16
    • 0033516280 scopus 로고    scopus 로고
    • Chemical synthesis and preliminary structural characterization of a nitrous acid interstrand cross-linked duplex DNA
    • Harwood,E.A., Sigurdsson,S.T., Edfeldt,N.B.F., Reid,B.R. and Hopkins,P.B. (1999) Chemical synthesis and preliminary structural characterization of a nitrous acid interstrand cross-linked duplex DNA. J. Am. Chem. Soc., 121, 5081-5082.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 5081-5082
    • Harwood, E.A.1    Sigurdsson, S.T.2    Edfeldt, N.B.F.3    Reid, B.R.4    Hopkins, P.B.5
  • 17
    • 0035901641 scopus 로고    scopus 로고
    • Synthesis of dna oligomers possessing a covalently cross-linked Watson-Crick base pair model
    • Li,H.Y., Qiu,Y.L., Moyroud,E. and Kishi,Y. (2001) Synthesis of dna oligomers possessing a covalently cross-linked Watson-Crick base pair model. Angew. Chem. Int. Ed. Engl., 40, 1471-1475.
    • (2001) Angew. Chem. Int. Ed. Engl. , vol.40 , pp. 1471-1475
    • Li, H.Y.1    Qiu, Y.L.2    Moyroud, E.3    Kishi, Y.4
  • 18
    • 0034821215 scopus 로고    scopus 로고
    • Synthesis and characterization of DNA duplexes containing an N(4) C-ethyl-N(4)C interstrand cross-link
    • Noll,D.M., Noronha,A.M. and Miller,P.S. (2001) Synthesis and characterization of DNA duplexes containing an N(4)C-ethyl-N(4)C interstrand cross-link. J. Am. Chem. Soc., 123, 3405-3411.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 3405-3411
    • Noll, D.M.1    Noronha, A.M.2    Miller, P.S.3
  • 19
    • 0037154085 scopus 로고    scopus 로고
    • N(4)C-ethyl-N(4)C cross-linked DNA: Synthesis and characterization of duplexes with interstrand cross-links of different orientations
    • Noronha,A.M., Noll,D.M., Wilds,C.J. and Miller,P.S. (2002) N(4)C-ethyl-N(4)C cross-linked DNA: Synthesis and characterization of duplexes with interstrand cross-links of different orientations. Biochemistry, 41, 760-771.
    • (2002) Biochemistry , vol.41 , pp. 760-771
    • Noronha, A.M.1    Noll, D.M.2    Wilds, C.J.3    Miller, P.S.4
  • 20
    • 3342920613 scopus 로고    scopus 로고
    • 3T interstrand cross-linked DNA: Synthesis and characterization of duplexes with interstrand cross-links of variable length
    • 3T interstrand cross-linked DNA: Synthesis and characterization of duplexes with interstrand cross-links of variable length. J. Am. Chem. Soc., 126, 9257-9265.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 9257-9265
    • Wilds, C.J.1    Noronha, A.M.2    Robidoux, S.3    Miller, P.S.4
  • 21
    • 0001760203 scopus 로고    scopus 로고
    • Solid-phase synthesis of oligonucleotides containing a site-specific psoralen derivative
    • Kobertz,W.R. and Essigmann,J.M. (1997) Solid-phase synthesis of oligonucleotides containing a site-specific psoralen derivative. J. Am. Chem. Soc., 119, 5960-5961.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 5960-5961
    • Kobertz, W.R.1    Essigmann, J.M.2
  • 22
    • 23044438590 scopus 로고    scopus 로고
    • DNA interstrand cross-link formation initiated by reaction between singlet oxygen and a modified nucleotide
    • Hong,I.S. and Greenberg,M.M. (2005) DNA interstrand cross-link formation initiated by reaction between singlet oxygen and a modified nucleotide. J. Am. Chem. Soc., 127, 10510-10511.
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 10510-10511
    • Hong, I.S.1    Greenberg, M.M.2
  • 23
    • 15744405105 scopus 로고    scopus 로고
    • Efficient DNA interstrand cross-link formation from a nucleotide radical
    • Hong,I.S. and Greenberg,M.M. (2005) Efficient DNA interstrand cross-link formation from a nucleotide radical. J. Am. Chem. Soc., 127, 3692-3693.
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 3692-3693
    • Hong, I.S.1    Greenberg, M.M.2
  • 24
    • 0000459358 scopus 로고
    • Synthesis and characterization of disulfide cross-linked oligonucleotides
    • Ferentz,A.E., Keating,T.E. and Verdine,G.L. (1993) Synthesis and characterization of disulfide cross-linked oligonucleotides. J. Am. Chem. Soc., 115, 9006-9014.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 9006-9014
    • Ferentz, A.E.1    Keating, T.E.2    Verdine, G.L.3
  • 25
    • 0027881738 scopus 로고
    • DNA methylation through a locally unpaired intermediate
    • Erlanson,D.A., Chen,L. and Verdine,G.L. (1993) DNA methylation through a locally unpaired intermediate. J. Am. Chem. Soc., 115, 12583-12584.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 12583-12584
    • Erlanson, D.A.1    Chen, L.2    Verdine, G.L.3
  • 26
    • 0035961532 scopus 로고    scopus 로고
    • Structural studies of an oligodeoxynucleotide containing a trimethylene interstrand cross-link in a 5′-(CpG) motif: Model of a malondialdehyde cross-link
    • Dooley,P.A., Tsarouhtsis,D., Korbel,G.A., Nechev,L.V., Shearer,J., Zegar,I.S., Harris,C.M., Stone,M.P. and Harris,T.M. (2001) Structural studies of an oligodeoxynucleotide containing a trimethylene interstrand cross-link in a 5′-(CpG) motif: Model of a malondialdehyde cross-link. J. Am. Chem. Soc., 123, 1730-1739.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 1730-1739
    • Dooley, P.A.1    Tsarouhtsis, D.2    Korbel, G.A.3    Nechev, L.V.4    Shearer, J.5    Zegar, I.S.6    Harris, C.M.7    Stone, M.P.8    Harris, T.M.9
  • 27
    • 0031469549 scopus 로고    scopus 로고
    • The chloroethylnitrosoureas: Sensitivity and resistance to cancer chemotherapy at the molecular level
    • Ludlum,D.B. (1997) The chloroethylnitrosoureas: Sensitivity and resistance to cancer chemotherapy at the molecular level. Cancer Invest., 15, 588-598.
    • (1997) Cancer Invest. , vol.15 , pp. 588-598
    • Ludlum, D.B.1
  • 28
    • 0019802611 scopus 로고
    • Synthesis of 4-triazolopyrimidinone nucleotide and its application in synthesis of 5-methylcytosine-containing oligodeoxyribonucleotides
    • Sung,W.L. (1981) Synthesis of 4-triazolopyrimidinone nucleotide and its application in synthesis of 5-methylcytosine-containing oligodeoxyribonucleotides. Nucleic Acids Res., 9, 6139-6151.
    • (1981) Nucleic Acids Res. , vol.9 , pp. 6139-6151
    • Sung, W.L.1
  • 29
    • 0037423339 scopus 로고    scopus 로고
    • Efficient syntheses of 2-chloro-2′-deoxyadenosine (cladribine) from 2′-deoxyguanosine(1)
    • Janeba,Z., Francom,P. and Robins,M.J. (2003) Efficient syntheses of 2-chloro-2′-deoxyadenosine (cladribine) from 2′-deoxyguanosine(1). J. Org. Chem., 68, 989-992.
    • (2003) J. Org. Chem. , vol.68 , pp. 989-992
    • Janeba, Z.1    Francom, P.2    Robins, M.J.3
  • 30
    • 0026069463 scopus 로고
    • Synthetic approaches to new doubly modified nucleosides: Congeners of cordycepin and related 2-deoxyadenosine
    • Nair,V. and Purdy,D.F. (1991) Synthetic approaches to new doubly modified nucleosides: Congeners of cordycepin and related 2-deoxyadenosine. Tetrahedron, 47, 365-382.
    • (1991) Tetrahedron , vol.47 , pp. 365-382
    • Nair, V.1    Purdy, D.F.2
  • 31
    • 0035477234 scopus 로고    scopus 로고
    • Covalent capture of a human O(6)-alkylguanine alkyltransferase-DNA complex using N(1),O(6)-ethanoxanthosine, a mechanism-based crosslinker
    • Noll,D.M. and Clarke,N.D. (2001) Covalent capture of a human O(6)-alkylguanine alkyltransferase-DNA complex using N(1),O(6)-ethanoxanthosine, a mechanism-based crosslinker. Nucleic Acids Res., 29, 4025-4034.
    • (2001) Nucleic Acids Res. , vol.29 , pp. 4025-4034
    • Noll, D.M.1    Clarke, N.D.2
  • 32
    • 0037974281 scopus 로고    scopus 로고
    • Regioselective synthesis of 1,N(2)-etheno-2′-deoxyguanosine and its generation in oligomeric DNA
    • Huang,Y., Torres,M.C., Iden,C.R. and Johnson,F. (2003) Regioselective synthesis of 1,N(2)-etheno-2′-deoxyguanosine and its generation in oligomeric DNA. Chem. Res. Toxicol., 16, 708-714.
    • (2003) Chem. Res. Toxicol. , vol.16 , pp. 708-714
    • Huang, Y.1    Torres, M.C.2    Iden, C.R.3    Johnson, F.4
  • 33
    • 17144362544 scopus 로고    scopus 로고
    • Site-specific incorporation of N-(deoxyguanosin-8-yl)- 2-acetylaminofluorene (dG-AAF) into oligonucleotides using modified 'ultra-mild' DNA synthesis
    • Gillet,L.C., Alzeer,J. and Schärer,O.D. (2005) Site-specific incorporation of N-(deoxyguanosin-8-yl)-2-acetylaminofluorene (dG-AAF) into oligonucleotides using modified 'ultra-mild' DNA synthesis. Nucleic Acids Res., 33, 1961-1969.
    • (2005) Nucleic Acids Res. , vol.33 , pp. 1961-1969
    • Gillet, L.C.1    Alzeer, J.2    Schärer, O.D.3
  • 34
    • 0030943626 scopus 로고    scopus 로고
    • Hydroquinone-O,O'-diacetic acid as a more labile replacement of succinic acid linkers in solid-phase oligonucleotide synthesis
    • Pon,R.T. and Yu,S. (1997) Hydroquinone-O,O'-diacetic acid as a more labile replacement of succinic acid linkers in solid-phase oligonucleotide synthesis. Tetrahedron Let., 38, 3327-3330.
    • (1997) Tetrahedron Let. , vol.38 , pp. 3327-3330
    • Pon, R.T.1    Yu, S.2
  • 35
    • 0016236559 scopus 로고
    • Some chemical aspects of dose-response relationships in alkylation mutagenesis
    • Lawley,P.D. (1974) Some chemical aspects of dose-response relationships in alkylation mutagenesis. Mutat. Res., 23, 283-295.
    • (1974) Mutat. Res. , vol.23 , pp. 283-295
    • Lawley, P.D.1
  • 36
    • 0028301897 scopus 로고
    • A violation of the Swain-Scott principle, and not SN1 versus SN2 reaction mechanisms, explains why carcinogenic alkylating agents can form different proportions of adducts at oxygen versus nitrogen in DNA
    • Loechler,E.L. (1994) A violation of the Swain-Scott principle, and not SN1 versus SN2 reaction mechanisms, explains why carcinogenic alkylating agents can form different proportions of adducts at oxygen versus nitrogen in DNA. Chem. Res. Toxicol., 7, 277-280.
    • (1994) Chem. Res. Toxicol. , vol.7 , pp. 277-280
    • Loechler, E.L.1
  • 37
    • 0035079294 scopus 로고    scopus 로고
    • Active oligonucleotides incorporating alkylating an agent as potential sequence- and base selective modifier of gene expression
    • Sasaki,S. (2001) Active oligonucleotides incorporating alkylating an agent as potential sequence- and base selective modifier of gene expression. Eur. J. Pharm. Sci., 13, 43-51.
    • (2001) Eur. J. Pharm. Sci. , vol.13 , pp. 43-51
    • Sasaki, S.1
  • 38
    • 0036120314 scopus 로고    scopus 로고
    • Triplex-forming oligonucleotides: Principles and applications
    • Vasquez,K.M. and Glazer,P.M. (2002) Triplex-forming oligonucleotides: principles and applications. Q. Rev. Biophys., 35, 89-107.
    • (2002) Q. Rev. Biophys. , vol.35 , pp. 89-107
    • Vasquez, K.M.1    Glazer, P.M.2
  • 39
    • 33746255457 scopus 로고    scopus 로고
    • Intracellular inducible alkylation system that exhibits antisense effects with greater potency and selectivity than the natural oligonucleotide
    • Ali,M.M., Oishi,M., Nagatsugi,F., Mori,K., Nagasaki,Y., Kataoka,K. and Sasaki,S. (2006) Intracellular inducible alkylation system that exhibits antisense effects with greater potency and selectivity than the natural oligonucleotide. Angew. Chem. Int. Ed. Engl., 45, 3136-3140.
    • (2006) Angew. Chem. Int. Ed. Engl. , vol.45 , pp. 3136-3140
    • Ali, M.M.1    Oishi, M.2    Nagatsugi, F.3    Mori, K.4    Nagasaki, Y.5    Kataoka, K.6    Sasaki, S.7


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.