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Volumn 51, Issue 8-9, 2010, Pages 800-814

Possible structural and functional determinants contributing to the clastogenicity of pharmaceuticals

Author keywords

Intercalation; Non covalent binding; Pharmaceuticals; Topoisomerase

Indexed keywords

ACLARUBICIN; ALMOTRIPTAN; AMFEPRAMONE; AMITRIPTYLINE; AMONAFIDE; APRINDINE; AURAMINE; AZAPROPAZONE; BAMBUTEROL; BROMPHENIRAMINE; CABERGOLINE; CHLOROPYRILENE; CHLOROQUINE; CHLORPHENIRAMINE; CHLORPROMAZINE; CHLORPROTHIXENE; CITALOPRAM; CLOMIFENE; CLOMIPRAMINE; CLORICROMEN; CYAMEMAZINE; DACARBAZINE; DAMINOZIDE; DNA TOPOISOMERASE; FORSKOLIN; KETONE; MUTAGENIC AGENT; PIPERIDINE; PYRIDINE; UNINDEXED DRUG; DRUG; PIPERIDINE DERIVATIVE; PYRIDINE DERIVATIVE;

EID: 78349277240     PISSN: 08936692     EISSN: 10982280     Source Type: Journal    
DOI: 10.1002/em.20626     Document Type: Review
Times cited : (17)

References (50)
  • 2
    • 43149124005 scopus 로고    scopus 로고
    • (-)-Epigallocatechin gallate, a major constituent of green tea, poisons human type II topoisomerases
    • Bandele OJ, Osheroff N. 2008. (-)-Epigallocatechin gallate, a major constituent of green tea, poisons human type II topoisomerases. Chem Res Toxicol 21: 936-943.
    • (2008) Chem Res Toxicol , vol.21 , pp. 936-943
    • Bandele, O.J.1    Osheroff, N.2
  • 3
    • 0018881537 scopus 로고
    • Lack of correlation between intercalation and plasmid curing ability of some tricyclic compounds
    • Barabus K, Molnar J. 1980. Lack of correlation between intercalation and plasmid curing ability of some tricyclic compounds. Acta Microbiol Acad Sci Hung 27: 55-61.
    • (1980) Acta Microbiol Acad Sci Hung , vol.27 , pp. 55-61
    • Barabus, K.1    Molnar, J.2
  • 4
    • 59449102286 scopus 로고    scopus 로고
    • Update on genotoxicity and carcinogenicity testing of 472 marketed pharmaceuticals
    • Brambilla G, Martelli A. 2009. Update on genotoxicity and carcinogenicity testing of 472 marketed pharmaceuticals. Mutat Res 681: 209-229.
    • (2009) Mutat Res , vol.681 , pp. 209-229
    • Brambilla, G.1    Martelli, A.2
  • 6
    • 63349086953 scopus 로고    scopus 로고
    • The DNA cleavage reaction of topoisomerase II: Wolf in sheep's clothing
    • Deweese JE, Osheroff N. 2009. The DNA cleavage reaction of topoisomerase II: Wolf in sheep's clothing. Nucleic Acids Res 373: 738-748.
    • (2009) Nucleic Acids Res , vol.373 , pp. 738-748
    • Deweese, J.E.1    Osheroff, N.2
  • 7
    • 0344211864 scopus 로고    scopus 로고
    • Use of temozolomide with other cytotoxic chemotherapy in the treatment of patients with recurrent brain metastases from lung cancer
    • Ebert BL, Niemerko E, Shaffer K, Salfia R. 2003. Use of temozolomide with other cytotoxic chemotherapy in the treatment of patients with recurrent brain metastases from lung cancer. Oncologist 8: 69-75.
    • (2003) Oncologist , vol.8 , pp. 69-75
    • Ebert, B.L.1    Niemerko, E.2    Shaffer, K.3    Salfia, R.4
  • 10
    • 0032052817 scopus 로고    scopus 로고
    • The ligand insertion hypothesis in the genomic action of steroid hormones
    • Hendry LB, Bransome EDJr, Mahesh VB. 1998. The ligand insertion hypothesis in the genomic action of steroid hormones. J Steroid Biochem Mol Biol 65: 75-89.
    • (1998) J Steroid Biochem Mol Biol , vol.65 , pp. 75-89
    • Hendry, L.B.1    Bransome Jr, E.D.2    Mahesh, V.B.3
  • 11
    • 33846654082 scopus 로고    scopus 로고
    • Chromosome aberrations in Chinese hamster and human cells: A comparison using compounds with various genotoxicity profiles
    • Hilliard C, Hill R, Armstrong M, Fleckenstein C, Crowley J, Freeland E, Duffy D, Galloway SM. 2007. Chromosome aberrations in Chinese hamster and human cells: A comparison using compounds with various genotoxicity profiles. Mutat Res 616: 103-118.
    • (2007) Mutat Res , vol.616 , pp. 103-118
    • Hilliard, C.1    Hill, R.2    Armstrong, M.3    Fleckenstein, C.4    Crowley, J.5    Freeland, E.6    Duffy, D.7    Galloway, S.M.8
  • 12
    • 52049120609 scopus 로고    scopus 로고
    • Molecular docking of intercalators and groove-binders to nucleic acids using autodock and surflex
    • Holt PA, Chaires JB, Trent JO. 2008. Molecular docking of intercalators and groove-binders to nucleic acids using autodock and surflex. J Chem Inf Model 48: 1602-1615.
    • (2008) J Chem Inf Model , vol.48 , pp. 1602-1615
    • Holt, P.A.1    Chaires, J.B.2    Trent, J.O.3
  • 13
    • 78650454065 scopus 로고
    • IARC, Caprolactam (Group 4)., Summary of data reported and evaluation.
    • IARC, Caprolactam (Group 4). 1991. Summary of data reported and evaluation. 71: 383
    • (1991) , vol.71 , pp. 383
  • 14
    • 0026062312 scopus 로고
    • Genotoxicity under extreme culture conditions
    • ICPEMC (International Commission for Protection Against Environmental Mutagens and carcinogens).
    • ICPEMC (International Commission for Protection Against Environmental Mutagens and carcinogens). 1991. Genotoxicity under extreme culture conditions. Mutat Res 257: 147-204.
    • (1991) Mutat Res , vol.257 , pp. 147-204
  • 15
    • 21544473568 scopus 로고    scopus 로고
    • Evaluation of the ability of a battery of three in vitro genotoxicity tests to discriminate rodent carcinogens and non-carcinogens. I. Sensitivity, specificity and relative predictivity
    • Kirkland D, Aardema M, Henderson L, Muller L. 2005. Evaluation of the ability of a battery of three in vitro genotoxicity tests to discriminate rodent carcinogens and non-carcinogens. I. Sensitivity, specificity and relative predictivity. Mutat Res 584: 1-256.
    • (2005) Mutat Res , vol.584 , pp. 1-256
    • Kirkland, D.1    Aardema, M.2    Henderson, L.3    Muller, L.4
  • 16
    • 0032718228 scopus 로고    scopus 로고
    • Inhibitors of topoisomerase II as pH-dependent modulators of etoposide-mediated cytotoxicity
    • Langer SP, Schmidt G, Sorensen M, Sehested M, Jensen PB. 1999. Inhibitors of topoisomerase II as pH-dependent modulators of etoposide-mediated cytotoxicity. Clin Cancer Res 5: 2899-2907.
    • (1999) Clin Cancer Res , vol.5 , pp. 2899-2907
    • Langer, S.P.1    Schmidt, G.2    Sorensen, M.3    Sehested, M.4    Jensen, P.B.5
  • 18
    • 14844347928 scopus 로고    scopus 로고
    • Bacterial topoisomerase inhibitors: Quinolone and pyridine antibacterial agents
    • Mitscher LA. 2005. Bacterial topoisomerase inhibitors: Quinolone and pyridine antibacterial agents. Chem Rev 105: 559-592.
    • (2005) Chem Rev , vol.105 , pp. 559-592
    • Mitscher, L.A.1
  • 19
    • 0026764697 scopus 로고
    • Inhibition of Escherichia coli DNA topoisomerase I activity by phospholipids
    • Mizushima T, Natori S, Sekimizu K. 1992. Inhibition of Escherichia coli DNA topoisomerase I activity by phospholipids. Biochem J 285: 503-506.
    • (1992) Biochem J , vol.285 , pp. 503-506
    • Mizushima, T.1    Natori, S.2    Sekimizu, K.3
  • 20
    • 34247620722 scopus 로고    scopus 로고
    • Synthesis and topoisomerase poisoning activity of A-ring and E-ring substituted lutonin A derivatives
    • Nacro K, Zha C, Guzzo PR, Herr RJ, Peace D, Friedrich TD. 2007. Synthesis and topoisomerase poisoning activity of A-ring and E-ring substituted lutonin A derivatives. Biorg Med Chem 15: 4237-4246.
    • (2007) Biorg Med Chem , vol.15 , pp. 4237-4246
    • Nacro, K.1    Zha, C.2    Guzzo, P.R.3    Herr, R.J.4    Peace, D.5    Friedrich, T.D.6
  • 21
    • 0001129329 scopus 로고    scopus 로고
    • DNA Repair in Higher Eukaryotes
    • In Nickoloff JKA,Hoekstra MF, editors., DNA Damage and Repair, Totowa, NJ, Humana Press. p.
    • Nitiss JL. 1998. DNA topoisomerases in DNA repair and DNA damage tolerance. In Nickoloff JKA, Hoekstra MF, editors. DNA Damage and Repair, Vol 2: DNA Repair in Higher Eukaryotes. Totowa, NJ: Humana Press. p. 517-537.
    • (1998) DNA topoisomerases in DNA repair and DNA damage tolerance , vol.2 , pp. 517-537
    • Nitiss, J.L.1
  • 22
    • 0028263354 scopus 로고
    • Berenil acts as a poison of eucaryotic topoisomerase II
    • Portugal J. 1994. Berenil acts as a poison of eucaryotic topoisomerase II. FEBS Lett 344: 136-138.
    • (1994) FEBS Lett , vol.344 , pp. 136-138
    • Portugal, J.1
  • 23
    • 33847771813 scopus 로고    scopus 로고
    • Synthesis cytotoxicity and DNA topoisomerase II inhibitory activity of benzofuroquinolinediones
    • Rhee H-K, Park HJ, Lee SK, Lee C-O, Choo H-YP. 2007. Synthesis cytotoxicity and DNA topoisomerase II inhibitory activity of benzofuroquinolinediones. Bioorg Med Chem 15: 1651-1658.
    • (2007) Bioorg Med Chem , vol.15 , pp. 1651-1658
    • Rhee, H.1    Park, H.J.2    Lee, S.K.3    Lee, C.4    Choo, H.5
  • 24
    • 0034193242 scopus 로고    scopus 로고
    • Sensitivity of human type II topoisomerases to DNA damage: Stimulation of enzyme-mediated DNA cleavage by abasic, oxidized and alkylated lesions
    • Sabourin M, Osheroff N. 2000. Sensitivity of human type II topoisomerases to DNA damage: Stimulation of enzyme-mediated DNA cleavage by abasic, oxidized and alkylated lesions. Nucleic Acids Res 28: 1947-1954.
    • (2000) Nucleic Acids Res , vol.28 , pp. 1947-1954
    • Sabourin, M.1    Osheroff, N.2
  • 25
    • 33846174381 scopus 로고    scopus 로고
    • QSAR studies and molecular shape analysis of azonafide derivatives as topoisomerase II inhibitors
    • Saravana KR, Moorthy N SHN, Trivedi P. 2003. QSAR studies and molecular shape analysis of azonafide derivatives as topoisomerase II inhibitors. Indian J Pharm Sci 65: 346-350.
    • (2003) Indian J Pharm Sci , vol.65 , pp. 346-350
    • Saravana, K.R.1    Moorthy N, S.H.N.2    Trivedi, P.3
  • 26
    • 58149099516 scopus 로고    scopus 로고
    • In silico functional profiling of small molecules and its applications
    • Sato T, Matsuo Y, Honma T, Yokoyama S. 2008. In silico functional profiling of small molecules and its applications. J Med Chem 51: 7705-7716.
    • (2008) J Med Chem , vol.51 , pp. 7705-7716
    • Sato, T.1    Matsuo, Y.2    Honma, T.3    Yokoyama, S.4
  • 27
    • 0024985067 scopus 로고
    • Rapid evaluation of topoisomease inhibitors: Caffeine inhibition of topoisomerases in vivo
    • Shin CG, Strayer JM, Wani MA, Snapka RM. 1990. Rapid evaluation of topoisomease inhibitors: Caffeine inhibition of topoisomerases in vivo. Teratog Carcinog Mutagen 10: 41-52.
    • (1990) Teratog Carcinog Mutagen , vol.10 , pp. 41-52
    • Shin, C.G.1    Strayer, J.M.2    Wani, M.A.3    Snapka, R.M.4
  • 28
    • 0030836293 scopus 로고    scopus 로고
    • Differential poisoning of topoisomerases by menogaril and nogalamycin dictated by the minor groove binding nogalose sugar
    • Sim S-P, Gatto B, Yu C, Liu AA, Li T-K, Pilch DS, LaVoie EJ, Liu LF. 1997. Differential poisoning of topoisomerases by menogaril and nogalamycin dictated by the minor groove binding nogalose sugar. Biochemistry 36: 13285-13291.
    • (1997) Biochemistry , vol.36 , pp. 13285-13291
    • Sim, S.1    Gatto, B.2    Yu, C.3    Liu, A.A.4    Li, T.5    Pilch, D.S.6    LaVoie, E.J.7    Liu, L.F.8
  • 29
    • 0032212386 scopus 로고    scopus 로고
    • A review and investigation into the mechanistic basis for the genotoxicity of antihistamines
    • Snyder RD. 1998. A review and investigation into the mechanistic basis for the genotoxicity of antihistamines. Mutat Res 411: 235-248.
    • (1998) Mutat Res , vol.411 , pp. 235-248
    • Snyder, R.D.1
  • 30
    • 0034003770 scopus 로고    scopus 로고
    • The use of catalytic topoisomerase II inhibitors to probe mechanisms of chemical-induced clastogenicity in Chinese hamster V79 cells
    • Snyder RD. 2000. The use of catalytic topoisomerase II inhibitors to probe mechanisms of chemical-induced clastogenicity in Chinese hamster V79 cells. Environ Mol Mutagen 35: 13-21.
    • (2000) Environ Mol Mutagen , vol.35 , pp. 13-21
    • Snyder, R.D.1
  • 31
    • 0037219551 scopus 로고    scopus 로고
    • Evidence from studies with intact mammalian cells that merbarone and bis(dioxopiperazine)s are topoisomerase II poisons
    • Snyder RD. 2003. Evidence from studies with intact mammalian cells that merbarone and bis(dioxopiperazine)s are topoisomerase II poisons. Drug Chem Toxicol 26: 15-22.
    • (2003) Drug Chem Toxicol , vol.26 , pp. 15-22
    • Snyder, R.D.1
  • 32
    • 78650478101 scopus 로고    scopus 로고
    • Non-covalent chemical/DNA interactions: Mechanisms and consequences
    • Snyder RD 2007. Non-covalent chemical/DNA interactions: Mechanisms and consequences. Mutat Res 623: 1-2.
    • (2007) Mutat Res , vol.623 , pp. 1-2
    • Snyder, R.D.1
  • 33
    • 67650752112 scopus 로고    scopus 로고
    • An update on the genotoxicity and carcinogenicity of marketed pharmaceuticals with reference to in silico predictivity
    • Snyder RD. 2009. An update on the genotoxicity and carcinogenicity of marketed pharmaceuticals with reference to in silico predictivity. Environ Mol Mutagen 50: 435-450.
    • (2009) Environ Mol Mutagen , vol.50 , pp. 435-450
    • Snyder, R.D.1
  • 34
    • 0032809432 scopus 로고    scopus 로고
    • Enhancement of bleomycin-induced micronucleus formation in V79 cells as a rapid and sensitive screen for non-covalent DNA-binding compounds
    • Snyder RD, Strekowski L. 1999. Enhancement of bleomycin-induced micronucleus formation in V79 cells as a rapid and sensitive screen for non-covalent DNA-binding compounds. Mutat Res 444: 181-192.
    • (1999) Mutat Res , vol.444 , pp. 181-192
    • Snyder, R.D.1    Strekowski, L.2
  • 35
    • 0034124249 scopus 로고    scopus 로고
    • The bleomycin amplification assay in V79 cells predicts frameshift mutagenicity of intercalative agents
    • Snyder RD, Diehl MS. 2000. The bleomycin amplification assay in V79 cells predicts frameshift mutagenicity of intercalative agents. Mutagen 15: 203-205.
    • (2000) Mutagen , vol.15 , pp. 203-205
    • Snyder, R.D.1    Diehl, M.S.2
  • 36
    • 0037134763 scopus 로고    scopus 로고
    • Putative identification of functional interactions between DNA intercalating agents and topoisomerase II using the V79 in vitro micronucleus assay
    • Snyder RD, Arnone MR. 2002. Putative identification of functional interactions between DNA intercalating agents and topoisomerase II using the V79 in vitro micronucleus assay. Mutat Res 503: 21-35.
    • (2002) Mutat Res , vol.503 , pp. 21-35
    • Snyder, R.D.1    Arnone, M.R.2
  • 37
    • 0036384072 scopus 로고    scopus 로고
    • Evidence for and role of the dimethylamino group in tamoxifen DNA intercalation in intact Chinese hamster V79 cells
    • Snyder RD, Brown JE. 2002. Evidence for and role of the dimethylamino group in tamoxifen DNA intercalation in intact Chinese hamster V79 cells. Drug Chem Toxicol 25: 473-479.
    • (2002) Drug Chem Toxicol , vol.25 , pp. 473-479
    • Snyder, R.D.1    Brown, J.E.2
  • 38
    • 0036938075 scopus 로고    scopus 로고
    • Evaluation of the clastogenic, DNA intercalative and topoisomerase II-interactive properties of bioflavonoids in Chinese hamster V79 cells
    • Snyder RD, Gillies PJ. 2002. Evaluation of the clastogenic, DNA intercalative and topoisomerase II-interactive properties of bioflavonoids in Chinese hamster V79 cells. Environ Mol Mutagen 40: 266-276.
    • (2002) Environ Mol Mutagen , vol.40 , pp. 266-276
    • Snyder, R.D.1    Gillies, P.J.2
  • 39
    • 4043104039 scopus 로고    scopus 로고
    • Evaluation of DNA intercalation potential of pharmaceuticals and other chemicals by cell-based and three-dimensional computational approaches
    • Snyder RD, Ewing DE, Hendry LB. 2004a. Evaluation of DNA intercalation potential of pharmaceuticals and other chemicals by cell-based and three-dimensional computational approaches. Environ Mol Mutagen 44: 163-173.
    • (2004) Environ Mol Mutagen , vol.44 , pp. 163-173
    • Snyder, R.D.1    Ewing, D.E.2    Hendry, L.B.3
  • 40
    • 2442548465 scopus 로고    scopus 로고
    • Assessment of the sensitivity of the computational programs DEREK, TOPKAT and MCASE in the prediction of the genotoxicity of pharmaceutical molecules
    • Snyder RD, Pearl GS, Mandakas G, Choy W-N, Goodsaid F, Rosenblum IY. 2004b. Assessment of the sensitivity of the computational programs DEREK, TOPKAT and MCASE in the prediction of the genotoxicity of pharmaceutical molecules. Environ Mol Mutagen 43: 143-158.
    • (2004) Environ Mol Mutagen , vol.43 , pp. 143-158
    • Snyder, R.D.1    Pearl, G.S.2    Mandakas, G.3    Choy, W.4    Goodsaid, F.5    Rosenblum, I.Y.6
  • 41
    • 25844472235 scopus 로고    scopus 로고
    • The influence of N-dialkyl and other cationic substituents on DNA intercalation and genotoxicity
    • Snyder RD, McNulty J, Zairov G, Ewing DE, Hendry LB. 2005. The influence of N-dialkyl and other cationic substituents on DNA intercalation and genotoxicity. Mutat Res 578: 88-99.
    • (2005) Mutat Res , vol.578 , pp. 88-99
    • Snyder, R.D.1    McNulty, J.2    Zairov, G.3    Ewing, D.E.4    Hendry, L.B.5
  • 42
    • 33748178209 scopus 로고    scopus 로고
    • DNA intercalative potential of marketed drugs testing positive in in vitro cytogenetics assays
    • Snyder RD, Ewing D, Hendry LB. 2006. DNA intercalative potential of marketed drugs testing positive in in vitro cytogenetics assays. Mutat Res 609: 47-59.
    • (2006) Mutat Res , vol.609 , pp. 47-59
    • Snyder, R.D.1    Ewing, D.2    Hendry, L.B.3
  • 43
    • 0018383777 scopus 로고
    • The effect on sister chromatid exchanges of drugs and dyes by intercalation and photoactivation
    • Speit G, Vogel W. 1979. The effect on sister chromatid exchanges of drugs and dyes by intercalation and photoactivation. Mutat Res 59: 223-229.
    • (1979) Mutat Res , vol.59 , pp. 223-229
    • Speit, G.1    Vogel, W.2
  • 44
    • 0012458399 scopus 로고
    • Molecular basis for the enhancement or inhibition of bleomycin-mediated degradation of DNA by DNA binding compounds
    • Strekowski L. 1992. Molecular basis for the enhancement or inhibition of bleomycin-mediated degradation of DNA by DNA binding compounds. Adv Detailed React Mech 2: 61-109.
    • (1992) Adv Detailed React Mech , vol.2 , pp. 61-109
    • Strekowski, L.1
  • 46
    • 39749119942 scopus 로고    scopus 로고
    • Next generation topoisomerase I inhibitors: Rationale and biomarker strategies
    • Teicher BA. 2008. Next generation topoisomerase I inhibitors: Rationale and biomarker strategies. Biochem Pharmacol 75: 1262-1271.
    • (2008) Biochem Pharmacol , vol.75 , pp. 1262-1271
    • Teicher, B.A.1
  • 47
    • 0026068727 scopus 로고
    • The effects of inhibitors of topoisomerase II, quinacrine of ultraviolet-induced DNA incision in normal and xeroderma pigmentosum fibroblasts
    • Thielmann HW, Popamda O, Edler L. 1991. The effects of inhibitors of topoisomerase II, quinacrine of ultraviolet-induced DNA incision in normal and xeroderma pigmentosum fibroblasts. J Cancer Res Clin Oncol 117: 1432-1435.
    • (1991) J Cancer Res Clin Oncol , vol.117 , pp. 1432-1435
    • Thielmann, H.W.1    Popamda, O.2    Edler, L.3
  • 48
    • 33947701471 scopus 로고    scopus 로고
    • Exploring DNA topoisomerases as targets of novel therapeutic agents in the treatment of infectious diseases
    • Tse-Dinh YC. 2007. Exploring DNA topoisomerases as targets of novel therapeutic agents in the treatment of infectious diseases. Infect Disord Drug Targets 7: 3-9.
    • (2007) Infect Disord Drug Targets , vol.7 , pp. 3-9
    • Tse-Dinh, Y.C.1


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