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Volumn 22, Issue 8, 2009, Pages 1435-1446

Chlorambucil-adducts in DNA analyzed at the oligonucleotide level using HPLC-ESI MS

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; CHLORAMBUCIL; DNA; GUANINE; NUCLEASE S1; OLIGONUCLEOTIDE; TRINUCLEOTIDE;

EID: 68949085188     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx900123r     Document Type: Article
Times cited : (38)

References (39)
  • 1
    • 0023481976 scopus 로고
    • Metabolism and reactions of alkylating agents
    • Farmer, P. B. (1987) Metabolism and reactions of alkylating agents. Pharmacol. Ther 35, 301-358.
    • (1987) Pharmacol. Ther , vol.35 , pp. 301-358
    • Farmer, P.B.1
  • 2
    • 0030844864 scopus 로고    scopus 로고
    • Specificity and kinetics of interstrand and intrastrand bifunctional alkylation by nitrogen mustards at a G-G-C sequence
    • Bauer, G. B., and Povirk, L. F. (1997) Specificity and kinetics of interstrand and intrastrand bifunctional alkylation by nitrogen mustards at a G-G-C sequence. Nucleic Acids Res. 25, 1211-1218.
    • (1997) Nucleic Acids Res , vol.25 , pp. 1211-1218
    • Bauer, G.B.1    Povirk, L.F.2
  • 3
    • 0021362088 scopus 로고
    • Relationships between functionality and genetic toxicology of selected DNA-damaging agents
    • Brendel, M., and Ruhland, A. (1984) Relationships between functionality and genetic toxicology of selected DNA-damaging agents. Mutat. Res. 133, 51-85.
    • (1984) Mutat. Res , vol.133 , pp. 51-85
    • Brendel, M.1    Ruhland, A.2
  • 4
    • 0025249224 scopus 로고
    • Mechlorethamine cross-links deoxyguanosine residues at 5′-GNC sequences in duplex DNA fragments
    • Millard, J. T., Raucher, S., and Hopkins, P. B. (1990) Mechlorethamine cross-links deoxyguanosine residues at 5′-GNC sequences in duplex DNA fragments. J. Am. Chem. Soc. 112, 2459-2460.
    • (1990) J. Am. Chem. Soc , vol.112 , pp. 2459-2460
    • Millard, J.T.1    Raucher, S.2    Hopkins, P.B.3
  • 5
    • 0028709432 scopus 로고
    • DNA Adducts of Nitrogen Mustards and Ethylene Imines
    • IACR Scientific Publications, Lyon, France;
    • Hemminki, K. (1994) DNA Adducts of Nitrogen Mustards and Ethylene Imines. In DNA Adducts: Identification and Biological Significance; IACR Scientific Publications, Lyon, France; Vol. 125.
    • (1994) DNA Adducts: Identification and Biological Significance , vol.125
    • Hemminki, K.1
  • 7
    • 0001676690 scopus 로고    scopus 로고
    • DNA cross-linking agents as antitumor drugs
    • Rajski, S. R., and Williams, R. M. (1998) DNA cross-linking agents as antitumor drugs. Chem. Rev. 98, 2723-2796.
    • (1998) Chem. Rev , vol.98 , pp. 2723-2796
    • Rajski, S.R.1    Williams, R.M.2
  • 8
    • 0005942065 scopus 로고
    • DNA damage and mutagenesis induced by nitrogen mustards
    • Povirk, L. F., and Shuker, D. E. (1994) DNA damage and mutagenesis induced by nitrogen mustards. Mutat. Res. 318, 205-226.
    • (1994) Mutat. Res , vol.318 , pp. 205-226
    • Povirk, L.F.1    Shuker, D.E.2
  • 9
    • 0028208637 scopus 로고
    • High-performance liquid chromatographic method for the separation of chlorambucil and its N-oxide prodrug
    • Chandler, K. J., McCabe, J. B., and Kirkpatrick, D. L. (1994) High-performance liquid chromatographic method for the separation of chlorambucil and its N-oxide prodrug. J. Chromatogr., B 652, 195-202.
    • (1994) J. Chromatogr., B , vol.652 , pp. 195-202
    • Chandler, K.J.1    McCabe, J.B.2    Kirkpatrick, D.L.3
  • 10
    • 0024599542 scopus 로고
    • Studies on the pharmacokinetics of chlorambucil and prednimustine in patients using a new high-performance liquid chromatographic assay
    • Oppitz, M. M., Musch, E., Malek, M., Rüb, H. P., Unruh, G. E., and Loos, U. (1989) Studies on the pharmacokinetics of chlorambucil and prednimustine in patients using a new high-performance liquid chromatographic assay. Cancer Chemother. Pharmacol. 23, 208-212.
    • (1989) Cancer Chemother. Pharmacol , vol.23 , pp. 208-212
    • Oppitz, M.M.1    Musch, E.2    Malek, M.3    Rüb, H.P.4    Unruh, G.E.5    Loos, U.6
  • 11
  • 12
    • 0017685920 scopus 로고
    • Studies on the toxicity and antitumour activity of prednimustine, a prednisolone ester of chlorambucil
    • Harrap, K. R., Riches, P. G., Gilby, E. D., Sellwood, S. M., Wilkinson, R., and Konyves, I. (1977) Studies on the toxicity and antitumour activity of prednimustine, a prednisolone ester of chlorambucil. Eur. J. Cancer 13, 873-881.
    • (1977) Eur. J. Cancer , vol.13 , pp. 873-881
    • Harrap, K.R.1    Riches, P.G.2    Gilby, E.D.3    Sellwood, S.M.4    Wilkinson, R.5    Konyves, I.6
  • 13
    • 0020701170 scopus 로고
    • Studies on the pharmacokinetics of chlorambucil and prednimustine in man
    • Newell, D. R., Calvert, A. H., Harrap, K. R., and McElwain, T. J. (1983) Studies on the pharmacokinetics of chlorambucil and prednimustine in man. Br. J. Clin. Pharmacol. 15, 253-258.
    • (1983) Br. J. Clin. Pharmacol , vol.15 , pp. 253-258
    • Newell, D.R.1    Calvert, A.H.2    Harrap, K.R.3    McElwain, T.J.4
  • 14
    • 0032864103 scopus 로고    scopus 로고
    • Rapid determination of the anti-cancer drug chlorambucil (Leukeran) and its phenyl acetic acid mustard metabolite in human serum and plasma by automated solid-phase extraction and liquid chromatography-tandem mass spectrometry
    • Davies, I. D., Allanson, J. P., and Causon, R. C. (1999) Rapid determination of the anti-cancer drug chlorambucil (Leukeran) and its phenyl acetic acid mustard metabolite in human serum and plasma by automated solid-phase extraction and liquid chromatography-tandem mass spectrometry. J. Chromatogr., B. 732, 173-184.
    • (1999) J. Chromatogr., B , vol.732 , pp. 173-184
    • Davies, I.D.1    Allanson, J.P.2    Causon, R.C.3
  • 15
    • 0037469374 scopus 로고    scopus 로고
    • Induction of SOS response, cellular efflux and oxidative stress response genes by chlorambucil in DNA repair-deficient escherichia coli cells (ada, ogt and mutS)
    • Salmelin, C., and Vilpo, J. (2003) Induction of SOS response, cellular efflux and oxidative stress response genes by chlorambucil in DNA repair-deficient escherichia coli cells (ada, ogt and mutS). Mutat. Res. 522, 33-44.
    • (2003) Mutat. Res , vol.522 , pp. 33-44
    • Salmelin, C.1    Vilpo, J.2
  • 16
    • 0023898319 scopus 로고
    • Ring-opened 7-methylguanine residues in DNA are a block to in vitro DNA synthesis
    • O'Connor, T. R., Boiteux, S., and Laval, J. (1988) Ring-opened 7-methylguanine residues in DNA are a block to in vitro DNA synthesis. Nucleic Acids Res. 16, 5879-5894.
    • (1988) Nucleic Acids Res , vol.16 , pp. 5879-5894
    • O'Connor, T.R.1    Boiteux, S.2    Laval, J.3
  • 17
    • 0026326721 scopus 로고
    • Thermolabile adenine adducts and A.T base pair substitutions induced by nitrogen-mustard analogs in an Sv40-based shuttle plasmid
    • Wang, P., Bauer, G. B., Bennett, R. A. O., and Povirk, L. F. (1991) Thermolabile adenine adducts and A.T base pair substitutions induced by nitrogen-mustard analogs in an Sv40-based shuttle plasmid. Biochemistry 30, 11515-11521.
    • (1991) Biochemistry , vol.30 , pp. 11515-11521
    • Wang, P.1    Bauer, G.B.2    Bennett, R.A.O.3    Povirk, L.F.4
  • 18
    • 0028110638 scopus 로고
    • Effect of distamycin on chlorambucil-induced mutagenesis in pZ189: Evidence of a role for minor groove alkylation at adenine N-3
    • Wang, P., Bauer, G. B., Kellogg, G. E., Abraham, D. J., and Povirk, L. F. (1994) Effect of distamycin on chlorambucil-induced mutagenesis in pZ189: evidence of a role for minor groove alkylation at adenine N-3. Mutagenesis 9, 133-139.
    • (1994) Mutagenesis , vol.9 , pp. 133-139
    • Wang, P.1    Bauer, G.B.2    Kellogg, G.E.3    Abraham, D.J.4    Povirk, L.F.5
  • 19
    • 0032486147 scopus 로고    scopus 로고
    • Comparative mutational spectra of the nitrogen mustard chlorambucil and its half-mustard analogue in Chinese hamster AS52 cells
    • Yaghi, B. M., Turner, P. M., Denny, W. A., Turner, P. R., O'Connor, C. J., and Ferguson, L. R. (1998) Comparative mutational spectra of the nitrogen mustard chlorambucil and its half-mustard analogue in Chinese hamster AS52 cells. Mutat. Res. 401, 153-164.
    • (1998) Mutat. Res , vol.401 , pp. 153-164
    • Yaghi, B.M.1    Turner, P.M.2    Denny, W.A.3    Turner, P.R.4    O'Connor, C.J.5    Ferguson, L.R.6
  • 20
    • 0034867532 scopus 로고    scopus 로고
    • Reactions of N, N-bis(2-chloroethyl)-p-aminophenylbutyric acid (chlorambucil) with 2′-deoxyguanosine
    • Haapala, E., Hakala, K., Jokipelto, E., Vilpo, J., and Hovinen, J. (2001) Reactions of N, N-bis(2-chloroethyl)-p-aminophenylbutyric acid (chlorambucil) with 2′-deoxyguanosine. Chem. Res. Toxicol. 14, 988-995.
    • (2001) Chem. Res. Toxicol , vol.14 , pp. 988-995
    • Haapala, E.1    Hakala, K.2    Jokipelto, E.3    Vilpo, J.4    Hovinen, J.5
  • 21
    • 0037350191 scopus 로고    scopus 로고
    • Reactions of N, N-bis(2-chloroethyl)-p-aminophenylbutyric acid (chlorambucil) with 2′-deoxyadenosine
    • Florea-Wang, D., Haapala, E., Mattinen, J., Hakala, K., Vilpo, J., and Hovinen, J. (2003) Reactions of N, N-bis(2-chloroethyl)-p-aminophenylbutyric acid (chlorambucil) with 2′-deoxyadenosine. Chem. Res. Toxicol. 16, 403-408.
    • (2003) Chem. Res. Toxicol , vol.16 , pp. 403-408
    • Florea-Wang, D.1    Haapala, E.2    Mattinen, J.3    Hakala, K.4    Vilpo, J.5    Hovinen, J.6
  • 22
    • 1642398310 scopus 로고    scopus 로고
    • Reactions of N, N-bis(2-chloroethyl)-p-aminophenylbutyric acid (chlorambucil) with 2′-deoxycytidine, 2′-deoxy-5- methylcytidine, and thymidine
    • Florea-Wang, D., Haapala, E., Mattinen, J., Hakala, K., Vilpo, J., and Hovinen, J. (2004) Reactions of N, N-bis(2-chloroethyl)-p-aminophenylbutyric acid (chlorambucil) with 2′-deoxycytidine, 2′-deoxy-5- methylcytidine, and thymidine. Chem. Res. Toxicol. 17, 383-391.
    • (2004) Chem. Res. Toxicol , vol.17 , pp. 383-391
    • Florea-Wang, D.1    Haapala, E.2    Mattinen, J.3    Hakala, K.4    Vilpo, J.5    Hovinen, J.6
  • 23
    • 0030750297 scopus 로고    scopus 로고
    • Styrene oxide DNA adducts: In vitro reaction and sensitive detection of modified oligonucleotides using capillary zone electrophoresis interfaced to electrospray mass spectrometry
    • Schrader, W., and Linscheid, M. (1997) Styrene oxide DNA adducts: in vitro reaction and sensitive detection of modified oligonucleotides using capillary zone electrophoresis interfaced to electrospray mass spectrometry. Arch. Toxicol. 71, 588-595.
    • (1997) Arch. Toxicol , vol.71 , pp. 588-595
    • Schrader, W.1    Linscheid, M.2
  • 24
    • 0028675623 scopus 로고
    • A new mass spectrometric approach to detect modifications in DNA
    • Janning, P., Schrader, W., and Linscheid, M. (1994) A new mass spectrometric approach to detect modifications in DNA. Rapid Commun. Mass Spectrom. 8, 1035-1040.
    • (1994) Rapid Commun. Mass Spectrom , vol.8 , pp. 1035-1040
    • Janning, P.1    Schrader, W.2    Linscheid, M.3
  • 25
    • 0033428560 scopus 로고    scopus 로고
    • Identification of single stranded regions of DNA by enzymatic digestion with matrix-assisted laser desorption/ionization analysis
    • Bartolini, W. P., Bentzley, C. M., Johnston, M. V., and Larsen, B. S. (1999) Identification of single stranded regions of DNA by enzymatic digestion with matrix-assisted laser desorption/ionization analysis. J. Am. Soc. Mass Spectrom. 10, 521-528.
    • (1999) J. Am. Soc. Mass Spectrom , vol.10 , pp. 521-528
    • Bartolini, W.P.1    Bentzley, C.M.2    Johnston, M.V.3    Larsen, B.S.4
  • 26
    • 0032933110 scopus 로고
    • Quantitative determination of DNA adducts using liquid chromatography/ electrospray ionization mass spectrometry and liquid chromatography/ high-resolution inductively coupled plasma mass spectrometry
    • Siethoff, C., Feldmann, I., Jakubowski, N., and Linscheid, M. (1993) Quantitative determination of DNA adducts using liquid chromatography/ electrospray ionization mass spectrometry and liquid chromatography/ high-resolution inductively coupled plasma mass spectrometry. J. Mass Spectrom. 34, 421-426.
    • (1993) J. Mass Spectrom , vol.34 , pp. 421-426
    • Siethoff, C.1    Feldmann, I.2    Jakubowski, N.3    Linscheid, M.4
  • 27
    • 33847650014 scopus 로고    scopus 로고
    • Investigation of enzymatic behavior of benzonase/alkaline phosphatase in the digestion of oligonucleotides and DNA by ESI-LC/MS
    • Liao, Q., Chiu, N. H., Shen, C., Chen, Y., and Vouros, P. (2007) Investigation of enzymatic behavior of benzonase/alkaline phosphatase in the digestion of oligonucleotides and DNA by ESI-LC/MS. Anal. Chem. 79, 1907-1917.
    • (2007) Anal. Chem , vol.79 , pp. 1907-1917
    • Liao, Q.1    Chiu, N.H.2    Shen, C.3    Chen, Y.4    Vouros, P.5
  • 28
    • 54549125794 scopus 로고    scopus 로고
    • Separation and identification of trinucleotide-melphalan adducts from enzymatically digested DNA using HPLC-ESI MS
    • Mohamed, D., and Linscheid, M. (2008) Separation and identification of trinucleotide-melphalan adducts from enzymatically digested DNA using HPLC-ESI MS. Anal. Bioanal. Chem. 392, 805-817.
    • (2008) Anal. Bioanal. Chem , vol.392 , pp. 805-817
    • Mohamed, D.1    Linscheid, M.2
  • 29
    • 0030982858 scopus 로고    scopus 로고
    • High sensitivity and fragmentation specificity in the analysis of drug-DNA adducts by electrospray tandem mass spectrometry
    • Iannitti, P., Sheil, M. M., and Wickham, G. (1997) High sensitivity and fragmentation specificity in the analysis of drug-DNA adducts by electrospray tandem mass spectrometry. J. Am. Chem. Soc. 119, 1490-1491.
    • (1997) J. Am. Chem. Soc , vol.119 , pp. 1490-1491
    • Iannitti, P.1    Sheil, M.M.2    Wickham, G.3
  • 30
    • 0000529864 scopus 로고
    • Decompositions of multiply-charged oligonucleotide anions
    • Mcluckey, S. A., and Habibigoudarzi, S. (1993) Decompositions of multiply-charged oligonucleotide anions. J. Am. Chem. Soc. 115, 12085-12095.
    • (1993) J. Am. Chem. Soc , vol.115 , pp. 12085-12095
    • Mcluckey, S.A.1    Habibigoudarzi, S.2
  • 31
    • 0032232419 scopus 로고    scopus 로고
    • Structure and fragmentation mechanisms of isomeric T-rich oligodeoxynucleotides: A comparison of four tandem mass spectrometric methods
    • Wang, Z., Wan, K. X., Ramanathan, R., Taylor, J. S., and Gross, M. L. (1998) Structure and fragmentation mechanisms of isomeric T-rich oligodeoxynucleotides: a comparison of four tandem mass spectrometric methods. J. Am. Soc. Mass Spectrom. 9, 683-691.
    • (1998) J. Am. Soc. Mass Spectrom , vol.9 , pp. 683-691
    • Wang, Z.1    Wan, K.X.2    Ramanathan, R.3    Taylor, J.S.4    Gross, M.L.5
  • 32
    • 0017194182 scopus 로고
    • All oxygens in nucleic acids react with carcinogenic ethylating agents
    • Singer, B. (1976) All oxygens in nucleic acids react with carcinogenic ethylating agents. Nature 264, 333-339.
    • (1976) Nature , vol.264 , pp. 333-339
    • Singer, B.1
  • 33
    • 0020016636 scopus 로고
    • DNA repair enzymes
    • Lindahl, T. (1982) DNA repair enzymes. Annu. Rev. Biochem. 51, 61-87.
    • (1982) Annu. Rev. Biochem , vol.51 , pp. 61-87
    • Lindahl, T.1
  • 34
    • 3242727654 scopus 로고    scopus 로고
    • Biologically relevant chemical reactions of N7-alkylguanine residues in DNA
    • Gates, K. S., Nooner, T., and Dutta, S. (2004) Biologically relevant chemical reactions of N7-alkylguanine residues in DNA. Chem. Res. Toxicol. 17, 839-856.
    • (2004) Chem. Res. Toxicol , vol.17 , pp. 839-856
    • Gates, K.S.1    Nooner, T.2    Dutta, S.3
  • 35
    • 0037139197 scopus 로고    scopus 로고
    • Chlorambucil-induced high mutation rate and suicidal gene downregulation in a base excision repairdeficient Escherichia coli strain
    • Salmelin, C., and Vilpo, J. (2002) Chlorambucil-induced high mutation rate and suicidal gene downregulation in a base excision repairdeficient Escherichia coli strain. Mutat. Res. 500, 125-134.
    • (2002) Mutat. Res , vol.500 , pp. 125-134
    • Salmelin, C.1    Vilpo, J.2
  • 36
    • 0037068446 scopus 로고    scopus 로고
    • Oxidative demethylation by Escherichia coli AlkB directly reverts DNA base damage
    • Trewick, S. C., Henshaw, T. F., Hausinger, R. P., Lindahl, T., and Sedgwick, B. (2002) Oxidative demethylation by Escherichia coli AlkB directly reverts DNA base damage. Nature 419, 174-178.
    • (2002) Nature , vol.419 , pp. 174-178
    • Trewick, S.C.1    Henshaw, T.F.2    Hausinger, R.P.3    Lindahl, T.4    Sedgwick, B.5
  • 37
    • 0027514969 scopus 로고
    • Alkylation of DNA by melphalan with special reference to adenine derivatives and adenineguanine cross-linking
    • Osborne, M. R., and Lawley, P. D. (1993) Alkylation of DNA by melphalan with special reference to adenine derivatives and adenineguanine cross-linking. Chem. Biol. Interact. 89, 49-60.
    • (1993) Chem. Biol. Interact , vol.89 , pp. 49-60
    • Osborne, M.R.1    Lawley, P.D.2
  • 39
    • 54549108750 scopus 로고    scopus 로고
    • Separation and characterization of oxaliplatin dinucleotides from DNA using HPLC-ESI ion trap mass spectrometry
    • Mowaka, S., and Linscheid, M. (2008) Separation and characterization of oxaliplatin dinucleotides from DNA using HPLC-ESI ion trap mass spectrometry. Anal. Bioanal. Chem. 392, 819-830.
    • (2008) Anal. Bioanal. Chem , vol.392 , pp. 819-830
    • Mowaka, S.1    Linscheid, M.2


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