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Volumn 45, Issue 1, 2006, Pages 79-90

Residues of genotoxic alkyl mesylates in mesylate salt drug substances: Real or imaginary problems?

Author keywords

Alkylating agents; Carcinogenicity; EMS; Genotoxicity; MMS; SN1; SN2; Swain Scott constants

Indexed keywords

ALCOHOL; ALKYL GROUP; ALKYLATING AGENT; AMINE; BASE; BROMIDE; CARCINOGEN; CHLORIDE; ESTER; HALIDE; MESYLIC ACID; MESYLIC ACID DERIVATIVE; SODIUM CHLORIDE; SOLVENT; SULFONIC ACID DERIVATIVE;

EID: 33646089419     PISSN: 02732300     EISSN: 10960295     Source Type: Journal    
DOI: 10.1016/j.yrtph.2006.02.003     Document Type: Article
Times cited : (49)

References (80)
  • 1
    • 0037025523 scopus 로고    scopus 로고
    • Zero exposure-a goal for environmental and occupational health?
    • Aitio A. Zero exposure-a goal for environmental and occupational health?. Toxicol. Lett. 134 (2002) 3-8
    • (2002) Toxicol. Lett. , vol.134 , pp. 3-8
    • Aitio, A.1
  • 2
    • 0033953180 scopus 로고    scopus 로고
    • Paracelsus to parascience; the environmental cancer distraction
    • Ames B., and Gold L. Paracelsus to parascience; the environmental cancer distraction. Mutat. Res. 447 (2000) 3-13
    • (2000) Mutat. Res. , vol.447 , pp. 3-13
    • Ames, B.1    Gold, L.2
  • 3
    • 0024422398 scopus 로고
    • Nucleophilic selectivity as a determinant of carcinogenic potency (TD50) in rodents: a comparison of mono- and bi-functional alkylating agents and vinyl chloride metabolites
    • Barbin A., and Bartsch H. Nucleophilic selectivity as a determinant of carcinogenic potency (TD50) in rodents: a comparison of mono- and bi-functional alkylating agents and vinyl chloride metabolites. Mutat. Res. 215 (1989) 95-106
    • (1989) Mutat. Res. , vol.215 , pp. 95-106
    • Barbin, A.1    Bartsch, H.2
  • 4
    • 0020349790 scopus 로고
    • Quantitative comparisons between carcinogenicity, mutagenicity and electrophilicity of direct-acting N-nitroso compounds and other alkylating agents
    • Bartsch H., Malaveille C., Tomatis L., Brun G., Dodet B., and Terracini B. Quantitative comparisons between carcinogenicity, mutagenicity and electrophilicity of direct-acting N-nitroso compounds and other alkylating agents. IARC Sci. Publ. 41 (1982) 525-532
    • (1982) IARC Sci. Publ. , Issue.41 , pp. 525-532
    • Bartsch, H.1    Malaveille, C.2    Tomatis, L.3    Brun, G.4    Dodet, B.5    Terracini, B.6
  • 5
    • 0020595342 scopus 로고
    • Quantitative comparison of carcinogenicity, mutagenicity and electrophilicity of 10 direct-acting alkylating agents and of the initial O6:7-alkylguanine ratio in DNA with carcinogenic potency in rodents
    • Bartsch H., Terracini B., Malaveille C., Tomatis L., Wahrendorf J., Brun G., and Dodet B. Quantitative comparison of carcinogenicity, mutagenicity and electrophilicity of 10 direct-acting alkylating agents and of the initial O6:7-alkylguanine ratio in DNA with carcinogenic potency in rodents. Mutat. Res. 110 (1983) 181-219
    • (1983) Mutat. Res. , vol.110 , pp. 181-219
    • Bartsch, H.1    Terracini, B.2    Malaveille, C.3    Tomatis, L.4    Wahrendorf, J.5    Brun, G.6    Dodet, B.7
  • 6
    • 33646098132 scopus 로고
    • N2 reactions with high carbocation character
    • N2 reactions with high carbocation character. JCS Perkin II (1978) 557-562
    • (1978) JCS Perkin II , pp. 557-562
    • Bentley, T.W.1    Bowen, C.T.2
  • 7
    • 0025288239 scopus 로고
    • Distribution of methyl and ethyl adducts following alkylation with monofunctional alkylating agents
    • Beranek D.T. Distribution of methyl and ethyl adducts following alkylation with monofunctional alkylating agents. Mutat. Res. 231 (1990) 11-30
    • (1990) Mutat. Res. , vol.231 , pp. 11-30
    • Beranek, D.T.1
  • 8
    • 0023153018 scopus 로고
    • Specific targets of alkylating agents in nuclear proteins of cultured hepatocytes
    • Boffa L.C., Bolognesi C., and Mariani M.R. Specific targets of alkylating agents in nuclear proteins of cultured hepatocytes. Mutat. Res. 190 (1987) 119-123
    • (1987) Mutat. Res. , vol.190 , pp. 119-123
    • Boffa, L.C.1    Bolognesi, C.2    Mariani, M.R.3
  • 11
    • 0017837811 scopus 로고
    • Comparative mutagenicity of alkylsulfate and alkanesulfonate derivatives in Chinese hamster ovary cells
    • Couch D.B., Forbes N.L., and Hsie A.W. Comparative mutagenicity of alkylsulfate and alkanesulfonate derivatives in Chinese hamster ovary cells. Mutat. Res. 57 (1978) 217-224
    • (1978) Mutat. Res. , vol.57 , pp. 217-224
    • Couch, D.B.1    Forbes, N.L.2    Hsie, A.W.3
  • 12
    • 33646087391 scopus 로고    scopus 로고
    • Council of Europe. 2000. Enquiry: alkyl mesilate (methanesulphonate) impurities in mesilate salts. Pharmeuropa. 12, 27.
  • 14
    • 0024588943 scopus 로고
    • The dependence of the mutagenicity of methanesulphonic acid esters in S. typhimurium TA100 on the alkylation mechanism
    • Eder E., and Kutt W. The dependence of the mutagenicity of methanesulphonic acid esters in S. typhimurium TA100 on the alkylation mechanism. Chem. Biol. Interact. 69 (1989) 45-59
    • (1989) Chem. Biol. Interact. , vol.69 , pp. 45-59
    • Eder, E.1    Kutt, W.2
  • 15
    • 0024399520 scopus 로고
    • Methyl methanesulphonate (MMS) is clearly mutagenic in S. typhimurium strain TA 1535; a comparison with strain TA 100
    • Eder E., Deininger C., and Wiedenmann M. Methyl methanesulphonate (MMS) is clearly mutagenic in S. typhimurium strain TA 1535; a comparison with strain TA 100. Mutat. Res. 226 (1989) 145-149
    • (1989) Mutat. Res. , vol.226 , pp. 145-149
    • Eder, E.1    Deininger, C.2    Wiedenmann, M.3
  • 16
    • 0024498352 scopus 로고
    • Genotoxicity of monofunctional methanesulphonates in the SOS chromotest as a function of alkylation mechanisms. A comparison with the mutagenicity in S. typhimurium TA100
    • Eder E., Deininger C., and Kutt W. Genotoxicity of monofunctional methanesulphonates in the SOS chromotest as a function of alkylation mechanisms. A comparison with the mutagenicity in S. typhimurium TA100. Mutat. Res. 211 (1989) 51-64
    • (1989) Mutat. Res. , vol.211 , pp. 51-64
    • Eder, E.1    Deininger, C.2    Kutt, W.3
  • 17
    • 0035979310 scopus 로고    scopus 로고
    • On the role of alkylating mechanisms, O-alkylation and DNA-repair in genotoxicity and mutagenicity of alkylating methanesulfonates of widely varying structures in bacterial systems
    • Eder E., Kutt W., and Deininger C. On the role of alkylating mechanisms, O-alkylation and DNA-repair in genotoxicity and mutagenicity of alkylating methanesulfonates of widely varying structures in bacterial systems. Chem. Biol. Interact. 137 (2001) 89-99
    • (2001) Chem. Biol. Interact. , vol.137 , pp. 89-99
    • Eder, E.1    Kutt, W.2    Deininger, C.3
  • 18
    • 0029977142 scopus 로고    scopus 로고
    • Macromolecule adducts as biomarkers of exposure to environmental mutagens in human populations
    • Ehrenberg L., Granath F., and Tornqvist M. Macromolecule adducts as biomarkers of exposure to environmental mutagens in human populations. Environ. Health Perspect. 104 Suppl. 3 (1996) 423-428
    • (1996) Environ. Health Perspect. , vol.104 , Issue.SUPPL. 3 , pp. 423-428
    • Ehrenberg, L.1    Granath, F.2    Tornqvist, M.3
  • 19
    • 33646082227 scopus 로고    scopus 로고
    • EMEA. 2004. Guideline on the limits of genotoxic impurities. .
  • 21
    • 33646091706 scopus 로고    scopus 로고
    • EPA, IRIS (Environmental Protection Agency, Integrated Risk Information System). .
  • 22
    • 0033565584 scopus 로고    scopus 로고
    • Natural and man-made mutagens and carcinogens in the human diet
    • Ferguson L.R. Natural and man-made mutagens and carcinogens in the human diet. Mutat. Res. 443 (1999) 1-10
    • (1999) Mutat. Res. , vol.443 , pp. 1-10
    • Ferguson, L.R.1
  • 23
    • 0026570889 scopus 로고
    • Modulation of mutagenic properties in a series of DNA-directed alkylating agents by variation of chain length and alkylator reactivity
    • Ferguson L.R., Turner P.M., Pogai H., and Denny W.A. Modulation of mutagenic properties in a series of DNA-directed alkylating agents by variation of chain length and alkylator reactivity. Mutat. Res. 265 (1992) 181-193
    • (1992) Mutat. Res. , vol.265 , pp. 181-193
    • Ferguson, L.R.1    Turner, P.M.2    Pogai, H.3    Denny, W.A.4
  • 24
    • 0019128228 scopus 로고
    • Evidence for the involvement of lesions other than O6-alkylguanine in mammalian cell mutagenesis
    • Fox M., and Brennand J. Evidence for the involvement of lesions other than O6-alkylguanine in mammalian cell mutagenesis. Carcinogenesis 1 (1980) 795-799
    • (1980) Carcinogenesis , vol.1 , pp. 795-799
    • Fox, M.1    Brennand, J.2
  • 25
    • 13844281029 scopus 로고    scopus 로고
    • Structure-activity considerations and in vitro approaches to assess the genotoxicity of 19 methane-, benzene- and toluenesulfonic acid esters
    • Glowienke S., Frieauff W., Allmendinger T., Martus H.J., Suter W., and Mueller L. Structure-activity considerations and in vitro approaches to assess the genotoxicity of 19 methane-, benzene- and toluenesulfonic acid esters. Mutat. Res. 581 (2005) 23-34
    • (2005) Mutat. Res. , vol.581 , pp. 23-34
    • Glowienke, S.1    Frieauff, W.2    Allmendinger, T.3    Martus, H.J.4    Suter, W.5    Mueller, L.6
  • 26
    • 0031565994 scopus 로고    scopus 로고
    • Studies of transalkylation of phosphotriesters in DNA: reaction conditions and requirements on nucleophiles for determination of DNA adducts
    • Haglund J., Ehrenberg L., and Tornqvist M. Studies of transalkylation of phosphotriesters in DNA: reaction conditions and requirements on nucleophiles for determination of DNA adducts. Chem. Biol. Interact. 108 (1997) 119-133
    • (1997) Chem. Biol. Interact. , vol.108 , pp. 119-133
    • Haglund, J.1    Ehrenberg, L.2    Tornqvist, M.3
  • 27
    • 0019135692 scopus 로고
    • Comparison of alkylation rates and mutagenicity of directly acting industrial and laboratory chemicals: epoxides, glycidyl ethers, methylating and ethylating agents, halogenated hydrocarbons, hydrazine derivatives, aldehydes, thiuram and dithiocarbamate derivatives
    • Hemminki K., Falck K., and Vainio H. Comparison of alkylation rates and mutagenicity of directly acting industrial and laboratory chemicals: epoxides, glycidyl ethers, methylating and ethylating agents, halogenated hydrocarbons, hydrazine derivatives, aldehydes, thiuram and dithiocarbamate derivatives. Arch. Toxicol. 46 (1980) 277-285
    • (1980) Arch. Toxicol. , vol.46 , pp. 277-285
    • Hemminki, K.1    Falck, K.2    Vainio, H.3
  • 28
  • 29
    • 33646116024 scopus 로고    scopus 로고
    • HSDB (Hazardous Substances Data Bank). .
  • 30
    • 33646097655 scopus 로고    scopus 로고
    • IARC (1). .
  • 31
    • 33646081741 scopus 로고    scopus 로고
    • IARC (2). .
  • 32
    • 33646102429 scopus 로고    scopus 로고
    • ICH, Q3C: Impurities: residual solvents. .
  • 33
    • 2642574948 scopus 로고    scopus 로고
    • Mechanisms and consequences of methylating agent-induced SCEs and chromosomal aberrations: a long road traveled and still a far way to go
    • Kaina B. Mechanisms and consequences of methylating agent-induced SCEs and chromosomal aberrations: a long road traveled and still a far way to go. Cytogenet. Genome Res. 104 (2004) 77-86
    • (2004) Cytogenet. Genome Res. , vol.104 , pp. 77-86
    • Kaina, B.1
  • 34
    • 0342288641 scopus 로고    scopus 로고
    • Interpretation of genotoxicity test results: the importance of thresholds
    • Kirkland D.J., and Müller L. Interpretation of genotoxicity test results: the importance of thresholds. Mutat. Res. 464 (2000) 137-147
    • (2000) Mutat. Res. , vol.464 , pp. 137-147
    • Kirkland, D.J.1    Müller, L.2
  • 35
    • 10844224478 scopus 로고    scopus 로고
    • Setting limits for genotoxic impurities in drug substances; threshold-based and pragmatic approaches
    • Kirkland D.J., and Snodin D.J.. Setting limits for genotoxic impurities in drug substances; threshold-based and pragmatic approaches. Int. J. Pharm. Med. 18 (2004) 197-207
    • (2004) Int. J. Pharm. Med. , vol.18 , pp. 197-207
    • Kirkland, D.J.1    Snodin, D.J..2
  • 37
    • 33646108796 scopus 로고    scopus 로고
    • Kornfeld, E.C., Bach, N.J., 1980. 6-Ethyl(or allyl)-8-methoxymethyl or methylmercaptomethylergolines and related compounds. US Patent 4, 202, 979.
  • 38
    • 0028804163 scopus 로고
    • Variability in DNA repair and individual susceptibility to genotoxins
    • Kyrtopoulos S.A. Variability in DNA repair and individual susceptibility to genotoxins. Clin. Chem. 41 (1995) 1848-1853
    • (1995) Clin. Chem. , vol.41 , pp. 1848-1853
    • Kyrtopoulos, S.A.1
  • 39
    • 16744362253 scopus 로고    scopus 로고
    • O6-Alkylguanine-DNA alkyltransferase: influence on susceptibility to the genetic effects of alkylating agents
    • Kyrtopoulos S.A. O6-Alkylguanine-DNA alkyltransferase: influence on susceptibility to the genetic effects of alkylating agents. Toxicol. Lett. 102-103 (1996) 53-57
    • (1996) Toxicol. Lett. , vol.102-103 , pp. 53-57
    • Kyrtopoulos, S.A.1
  • 40
    • 0026528038 scopus 로고
    • Base alterations in yeast induced by alkylating agents with differing Swain-Scott substrate constants
    • Lee G.S., Blonsky K.S., Van On D.L., Savage E.A., Morgan A.R., and von Borstel R.C. Base alterations in yeast induced by alkylating agents with differing Swain-Scott substrate constants. J. Mol. Biol. 223 (1992) 617-626
    • (1992) J. Mol. Biol. , vol.223 , pp. 617-626
    • Lee, G.S.1    Blonsky, K.S.2    Van On, D.L.3    Savage, E.A.4    Morgan, A.R.5    von Borstel, R.C.6
  • 41
    • 0042346202 scopus 로고    scopus 로고
    • Determination of polar alkylating agents as thiocyanate/isothiocyanate derivatives by reaction headspace gas chromatography
    • Lee C.R., Guivarch F., Nguyen Van Dau C., Tessier D., and Krstulovic A.M. Determination of polar alkylating agents as thiocyanate/isothiocyanate derivatives by reaction headspace gas chromatography. Analyst 128 (2003) 857-863
    • (2003) Analyst , vol.128 , pp. 857-863
    • Lee, C.R.1    Guivarch, F.2    Nguyen Van Dau, C.3    Tessier, D.4    Krstulovic, A.M.5
  • 42
    • 3843114399 scopus 로고    scopus 로고
    • Trace analysis of residual methyl methanesulfonate, ethyl methanesulfonate and isopropyl methanesulfonate in pharmaceuticals by capillary gas chromatography with flame ionization detection
    • Li W. Trace analysis of residual methyl methanesulfonate, ethyl methanesulfonate and isopropyl methanesulfonate in pharmaceuticals by capillary gas chromatography with flame ionization detection. J. Chromatogr. A 1046 (2004) 297-301
    • (2004) J. Chromatogr. A , vol.1046 , pp. 297-301
    • Li, W.1
  • 43
    • 18044381309 scopus 로고    scopus 로고
    • Investigation of solubility and dissolution of a free base and two different salt forms as a function of pH
    • Li S., Wong S., Sethia S., Almoazen H., Joshi Y.M., and Serajuddin A.T. Investigation of solubility and dissolution of a free base and two different salt forms as a function of pH. Pharm. Res. 22 (2005) 628-635
    • (2005) Pharm. Res. , vol.22 , pp. 628-635
    • Li, S.1    Wong, S.2    Sethia, S.3    Almoazen, H.4    Joshi, Y.M.5    Serajuddin, A.T.6
  • 44
    • 0032774819 scopus 로고    scopus 로고
    • Qualitative and quantitative procedures for health risk assessment
    • Lohman P.H. Qualitative and quantitative procedures for health risk assessment. Mutat. Res. 428 (1999) 237-254
    • (1999) Mutat. Res. , vol.428 , pp. 237-254
    • Lohman, P.H.1
  • 45
    • 0036856459 scopus 로고    scopus 로고
    • Mechanisms of carcinogenicity/chemotherapy by O6-methylguanine
    • Margison G.P., Santibanez Koref M.F., and Povey A.C. Mechanisms of carcinogenicity/chemotherapy by O6-methylguanine. Mutagenesis 17 (2002) 483-487
    • (2002) Mutagenesis , vol.17 , pp. 483-487
    • Margison, G.P.1    Santibanez Koref, M.F.2    Povey, A.C.3
  • 46
    • 33646088557 scopus 로고    scopus 로고
    • Miller, S.A., Ju, J., Cucolo, M., Dai, J.Y., Jia, J., Narra, K., Smith, A.M., Aubry, A.-F., 2004. A new capillary GC/MS method for determining ethyl methanesulfonate (EMS) and its stability in a drug product formulation, Poster at 52nd ASMS Conference.
  • 47
    • 13844316739 scopus 로고    scopus 로고
    • Epoxide hydrolases: mechanisms, inhibitor designs, and biological roles
    • Morisseau M., and Hammock B.D. Epoxide hydrolases: mechanisms, inhibitor designs, and biological roles. Annu. Rev. Pharmacol. Toxicol. 45 (2005) 311-333
    • (2005) Annu. Rev. Pharmacol. Toxicol. , vol.45 , pp. 311-333
    • Morisseau, M.1    Hammock, B.D.2
  • 48
    • 0030871409 scopus 로고    scopus 로고
    • Evaluation of the rodent micronucleus assay in the screening of IARC carcinogens (groups 1, 2A and 2B) the summary report of the 6th collaborative study by CSGMT/JEMS MMS. Collaborative Study of the Micronucleus Group Test. Mammalian Mutagenicity Study Group
    • Morita T., Asano N., Awogi T., Sasaki Y.F., Sato S., Shimada H., Sutou S., Suzuki T., Wakata A., Sofuni T., and Hayashi M. Evaluation of the rodent micronucleus assay in the screening of IARC carcinogens (groups 1, 2A and 2B) the summary report of the 6th collaborative study by CSGMT/JEMS MMS. Collaborative Study of the Micronucleus Group Test. Mammalian Mutagenicity Study Group. Mutat. Res. 389 (1997) 3-122
    • (1997) Mutat. Res. , vol.389 , pp. 3-122
    • Morita, T.1    Asano, N.2    Awogi, T.3    Sasaki, Y.F.4    Sato, S.5    Shimada, H.6    Sutou, S.7    Suzuki, T.8    Wakata, A.9    Sofuni, T.10    Hayashi, M.11
  • 49
    • 0033977243 scopus 로고    scopus 로고
    • DNA damage and repair: consequences on dose-responses
    • Moustacchi E. DNA damage and repair: consequences on dose-responses. Mutat. Res. 464 (2000) 35-40
    • (2000) Mutat. Res. , vol.464 , pp. 35-40
    • Moustacchi, E.1
  • 50
    • 0342316476 scopus 로고    scopus 로고
    • Human biological relevance and the use of threshold arguments in regulatory genotoxicity assessment: experience with pharmaceuticals
    • Müller L., and Kasper P. Human biological relevance and the use of threshold arguments in regulatory genotoxicity assessment: experience with pharmaceuticals. Mutat. Res. 464 (2000) 19-34
    • (2000) Mutat. Res. , vol.464 , pp. 19-34
    • Müller, L.1    Kasper, P.2
  • 52
    • 0018865117 scopus 로고
    • Mutagenicity of carcinogenic methylating agents is associated with a specific DNA modification
    • Newbold R.F., Warren W., Medcalf A.S., and Amos J. Mutagenicity of carcinogenic methylating agents is associated with a specific DNA modification. Nature 283 5747 (1980) 596-599
    • (1980) Nature , vol.283 , Issue.5747 , pp. 596-599
    • Newbold, R.F.1    Warren, W.2    Medcalf, A.S.3    Amos, J.4
  • 53
    • 0029760175 scopus 로고    scopus 로고
    • Conformational change in human DNA repair enzyme O6-methylguanine-DNA methyltransferase upon alkylation of its active site by SN1 (indirect-acting) and SN2 (direct-acting) alkylating agents: breaking a "salt-link"
    • Oh H.K., Teo A.K., Ali R.B., Lim A., Ayi T.C., Yarosh D.B., and Li B.F. Conformational change in human DNA repair enzyme O6-methylguanine-DNA methyltransferase upon alkylation of its active site by SN1 (indirect-acting) and SN2 (direct-acting) alkylating agents: breaking a "salt-link". Biochemistry 35 (1996) 12259-12266
    • (1996) Biochemistry , vol.35 , pp. 12259-12266
    • Oh, H.K.1    Teo, A.K.2    Ali, R.B.3    Lim, A.4    Ayi, T.C.5    Yarosh, D.B.6    Li, B.F.7
  • 54
    • 33947332005 scopus 로고
    • Application of the principle of hard and soft acids and bases to organic chemistry
    • Pearson R.G., and Songstad J. Application of the principle of hard and soft acids and bases to organic chemistry. J. Am. Chem. Soc. 89 (1967) 1827-1836
    • (1967) J. Am. Chem. Soc. , vol.89 , pp. 1827-1836
    • Pearson, R.G.1    Songstad, J.2
  • 55
    • 0021704198 scopus 로고
    • Properties of the O6-alkylguanine-DNA repair system of mammalian cells
    • Pegg A.E. Properties of the O6-alkylguanine-DNA repair system of mammalian cells. IARC Sci. Publ. 57 (1984) 575-580
    • (1984) IARC Sci. Publ. , Issue.57 , pp. 575-580
    • Pegg, A.E.1
  • 56
    • 0027487416 scopus 로고
    • The electrophile counterattack response: protection against neoplasia and toxicity
    • Prestera T., Zhang Y., Spencer S.R., Wilczak C.A., and Talalay P. The electrophile counterattack response: protection against neoplasia and toxicity. Adv. Enzyme Regul. 33 (1993) 281-296
    • (1993) Adv. Enzyme Regul. , vol.33 , pp. 281-296
    • Prestera, T.1    Zhang, Y.2    Spencer, S.R.3    Wilczak, C.A.4    Talalay, P.5
  • 57
    • 0034069585 scopus 로고    scopus 로고
    • DNA repair: counteragent in mutagenesis and carcinogenesis - accomplice in cancer therapy resistance
    • Rajewsky M.F., Engelbergs J., Thomale J., and Schweer T. DNA repair: counteragent in mutagenesis and carcinogenesis - accomplice in cancer therapy resistance. Mutat. Res. 462 (2000) 101-105
    • (2000) Mutat. Res. , vol.462 , pp. 101-105
    • Rajewsky, M.F.1    Engelbergs, J.2    Thomale, J.3    Schweer, T.4
  • 58
    • 0029738238 scopus 로고    scopus 로고
    • Gas chromatographic/mass spectrometric analysis of methyl methanesulphonate and ethyl methanesulphonate of DPI 201-106, a positive inotropic agent for the treatment of heart failure
    • Ramjit H.G., Singh M.M., and Coddington A.B. Gas chromatographic/mass spectrometric analysis of methyl methanesulphonate and ethyl methanesulphonate of DPI 201-106, a positive inotropic agent for the treatment of heart failure. J. Mass Spectrom. 31 (1996) 867-872
    • (1996) J. Mass Spectrom. , vol.31 , pp. 867-872
    • Ramjit, H.G.1    Singh, M.M.2    Coddington, A.B.3
  • 59
    • 0021717853 scopus 로고
    • A review of the genetic effects of ethyl methanesulfonate
    • Sega G.A. A review of the genetic effects of ethyl methanesulfonate. Mutat. Res. 134 (1984) 113-142
    • (1984) Mutat. Res. , vol.134 , pp. 113-142
    • Sega, G.A.1
  • 60
    • 0019482760 scopus 로고
    • A comparison of the molecular action of an SN1-type methylating agent, methyl nitrosourea and an SN2-type methylating agent, methyl methanesulfonate, in the germ cells of male mice
    • Sega G.A., Wolfem K.W., and Owensm J.G. A comparison of the molecular action of an SN1-type methylating agent, methyl nitrosourea and an SN2-type methylating agent, methyl methanesulfonate, in the germ cells of male mice. Chem. Biol. Interact. 33 (1981) 253-269
    • (1981) Chem. Biol. Interact. , vol.33 , pp. 253-269
    • Sega, G.A.1    Wolfem, K.W.2    Owensm, J.G.3
  • 61
    • 0023224249 scopus 로고
    • Induction of thymic lymphomas and squamous cell carcinomas following topic application of isopropyl methanesulfonate to female Hsd:(ICR)BR mice
    • Segal A., Seidman I., and Melchionne S. Induction of thymic lymphomas and squamous cell carcinomas following topic application of isopropyl methanesulfonate to female Hsd:(ICR)BR mice. Cancer Res. 47 (1987) 3402-3405
    • (1987) Cancer Res. , vol.47 , pp. 3402-3405
    • Segal, A.1    Seidman, I.2    Melchionne, S.3
  • 62
    • 0021287403 scopus 로고
    • Alkylation of the O6 of guanine is only one of many chemical events that may initiate carcinogenesis
    • Singer B. Alkylation of the O6 of guanine is only one of many chemical events that may initiate carcinogenesis. Cancer Invest. 2 (1984) 233-238
    • (1984) Cancer Invest. , vol.2 , pp. 233-238
    • Singer, B.1
  • 63
    • 0028981666 scopus 로고
    • Inactivation of O6-methylguanine-DNA methyltransferase in vivo by SN2 alkylating agents
    • Sledziewska-Gojska E. Inactivation of O6-methylguanine-DNA methyltransferase in vivo by SN2 alkylating agents. Mutat. Res. 336 (1995) 61-67
    • (1995) Mutat. Res. , vol.336 , pp. 61-67
    • Sledziewska-Gojska, E.1
  • 64
    • 18844467938 scopus 로고    scopus 로고
    • Different repair of O6-methylguanine occurring in DNA modified by MMS in vivo or in vitro
    • Sledziewska-Gojska E., and Torzewska D. Different repair of O6-methylguanine occurring in DNA modified by MMS in vivo or in vitro. Mutat. Res. 383 (1997) 31-37
    • (1997) Mutat. Res. , vol.383 , pp. 31-37
    • Sledziewska-Gojska, E.1    Torzewska, D.2
  • 65
    • 0021078520 scopus 로고
    • Cytotoxicity of monofunctional alkylating agents. Methyl methanesulfonate and methyl-N'-nitro-N-nitrosoguanidine have different mechanisms of toxicity for 10T1/2 cells
    • Smith G.J., and Grisham J.W. Cytotoxicity of monofunctional alkylating agents. Methyl methanesulfonate and methyl-N'-nitro-N-nitrosoguanidine have different mechanisms of toxicity for 10T1/2 cells. Mutat. Res. 111 (1983) 405-417
    • (1983) Mutat. Res. , vol.111 , pp. 405-417
    • Smith, G.J.1    Grisham, J.W.2
  • 66
    • 0000003828 scopus 로고
    • Quantitative correlation of reaction rates. Comparison of hydroxide ion with other nucleophilic reagents towards alkyl halides, esters, epoxides and acyl halides
    • Swain C.G., and Scott C.B. Quantitative correlation of reaction rates. Comparison of hydroxide ion with other nucleophilic reagents towards alkyl halides, esters, epoxides and acyl halides. J. Am. Chem. Soc. 75 (1953) 141-147
    • (1953) J. Am. Chem. Soc. , vol.75 , pp. 141-147
    • Swain, C.G.1    Scott, C.B.2
  • 67
    • 0020988012 scopus 로고
    • Significance of electrophilic reactivity and especially DNA alkylation in carcinogenesis and mutagenesis
    • Swenson D.H. Significance of electrophilic reactivity and especially DNA alkylation in carcinogenesis and mutagenesis. Dev. Toxicol. Environ. Sci. 11 (1983) 247-254
    • (1983) Dev. Toxicol. Environ. Sci. , vol.11 , pp. 247-254
    • Swenson, D.H.1
  • 68
    • 0017816766 scopus 로고
    • Alkylation of deoxyribonucleic acid by carcinogens dimethyl sulphate, ethyl methanesulphonate, N-ethyl-N-nitrosourea and N-methyl-N-nitrosourea. Relative reactivity of the phosphodiester site thymidylyl(3'-5')thymidine
    • Swenson D.H., and Lawley P.D. Alkylation of deoxyribonucleic acid by carcinogens dimethyl sulphate, ethyl methanesulphonate, N-ethyl-N-nitrosourea and N-methyl-N-nitrosourea. Relative reactivity of the phosphodiester site thymidylyl(3'-5')thymidine. Biochem. J. 171 (1978) 575-587
    • (1978) Biochem. J. , vol.171 , pp. 575-587
    • Swenson, D.H.1    Lawley, P.D.2
  • 69
    • 0029764211 scopus 로고    scopus 로고
    • Ethylene oxide as a biologically reactive intermediate of endogenous origin
    • Tornqvist M. Ethylene oxide as a biologically reactive intermediate of endogenous origin. Adv. Exp. Med. Biol. 387 (1996) 275-283
    • (1996) Adv. Exp. Med. Biol. , vol.387 , pp. 275-283
    • Tornqvist, M.1
  • 70
    • 0026038948 scopus 로고
    • Biological and chemical properties of alkanediazotates as active species of N-nitroso compounds
    • Ukawa S., and Mochizuki M. Biological and chemical properties of alkanediazotates as active species of N-nitroso compounds. IARC Sci. Publ. 105 (1991) 404-406
    • (1991) IARC Sci. Publ. , Issue.105 , pp. 404-406
    • Ukawa, S.1    Mochizuki, M.2
  • 71
    • 33646103875 scopus 로고    scopus 로고
    • Varsal Inc, .
  • 72
    • 0027952799 scopus 로고
    • International Commission for Protection Against Environmental Mutagens and Carcinogens. The subtlety of alkylating agents in reactions with biological macromolecules
    • Vogel E.W., and Nivard M.J. International Commission for Protection Against Environmental Mutagens and Carcinogens. The subtlety of alkylating agents in reactions with biological macromolecules. Mutat. Res. 305 (1994) 13-32
    • (1994) Mutat. Res. , vol.305 , pp. 13-32
    • Vogel, E.W.1    Nivard, M.J.2
  • 73
    • 0025605873 scopus 로고
    • Nucleophilic selectivity of alkylating agents and their hypermutability in Drosophila as predictors of carcinogenic potency in rodents
    • Vogel E.W., Barbin A., Nivard M.J., and Bartsch H. Nucleophilic selectivity of alkylating agents and their hypermutability in Drosophila as predictors of carcinogenic potency in rodents. Carcinogenesis 11 (1990) 2211-2217
    • (1990) Carcinogenesis , vol.11 , pp. 2211-2217
    • Vogel, E.W.1    Barbin, A.2    Nivard, M.J.3    Bartsch, H.4
  • 75
    • 0032565515 scopus 로고    scopus 로고
    • Heritable and cancer risks of exposures to anticancer drugs: inter-species comparisons of covalent deoxyribonucleic acid-binding agents
    • Vogel E.W., Barbin A., Nivard M.J., Stack H.F., Waters M.D., and Lohman P.H. Heritable and cancer risks of exposures to anticancer drugs: inter-species comparisons of covalent deoxyribonucleic acid-binding agents. Mutat. Res. 400 (1998) 509-540
    • (1998) Mutat. Res. , vol.400 , pp. 509-540
    • Vogel, E.W.1    Barbin, A.2    Nivard, M.J.3    Stack, H.F.4    Waters, M.D.5    Lohman, P.H.6
  • 76
    • 13644253379 scopus 로고    scopus 로고
    • Mutagenicity testing with transgenic mice. Part I: comparison with the mouse bone marrow micronucleus test
    • Wahnschaffe U., Bitch A., Kielhorn J., and Mangelsdorf I. Mutagenicity testing with transgenic mice. Part I: comparison with the mouse bone marrow micronucleus test. J. Carcinog. 4 (2005) 3
    • (2005) J. Carcinog. , vol.4 , pp. 3
    • Wahnschaffe, U.1    Bitch, A.2    Kielhorn, J.3    Mangelsdorf, I.4
  • 77
    • 13644265958 scopus 로고    scopus 로고
    • Mutagenicity testing with transgenic mice. Part II: comparison with the mouse spot test
    • Wahnschaffe U., Bitch A., Kielhorn J., and Mangelsdorf I. Mutagenicity testing with transgenic mice. Part II: comparison with the mouse spot test. J. Carcinog. 4 (2005) 4
    • (2005) J. Carcinog. , vol.4 , pp. 4
    • Wahnschaffe, U.1    Bitch, A.2    Kielhorn, J.3    Mangelsdorf, I.4
  • 78
    • 0018877345 scopus 로고
    • Determination of reaction rate constants for alkylation of 4-(p-nitrobenzyl) pyridine by different alkylating agents
    • Walles S.A. Determination of reaction rate constants for alkylation of 4-(p-nitrobenzyl) pyridine by different alkylating agents. Toxicol. Lett. 5 (1980) 161-167
    • (1980) Toxicol. Lett. , vol.5 , pp. 161-167
    • Walles, S.A.1
  • 79
    • 33646116774 scopus 로고    scopus 로고
    • Wohl, R.A., 1980. Process for preparing substituted bis(aminoureas). US Patent 4, 209, 624.
  • 80
    • 0030786804 scopus 로고    scopus 로고
    • New tester strains of Salmonella typhimurium lacking O6-methylguanine DNA methyltransferases and highly sensitive to mutagenic alkylating agents
    • Yamada M., Matsui K., Sofuni T., and Nohmi T. New tester strains of Salmonella typhimurium lacking O6-methylguanine DNA methyltransferases and highly sensitive to mutagenic alkylating agents. Mutat. Res. 381 (1997) 15-24
    • (1997) Mutat. Res. , vol.381 , pp. 15-24
    • Yamada, M.1    Matsui, K.2    Sofuni, T.3    Nohmi, T.4


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