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Volumn 25, Issue 1, 2012, Pages 197-206

DNA strand cleavage by the phenazine di- N -oxide natural product myxin under both aerobic and anaerobic conditions

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC N OXIDE; MYXIN; NATURAL PRODUCT; OXIDE; OXYGEN; TIRAPAZAMINE; UNCLASSIFIED DRUG;

EID: 84855834317     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx2004213     Document Type: Article
Times cited : (50)

References (84)
  • 1
    • 79951670097 scopus 로고    scopus 로고
    • Synthesis, hypoxia-selective cytotoxicity of new 3-amino-1,2,4- benzotriazine 1,4-dioxide derivatives
    • Xia, Q., Zhang, L., Zhang, J., Sheng, R., Yang, B., He, Q., and Hu, Y. (2011) Synthesis, hypoxia-selective cytotoxicity of new 3-amino-1,2,4- benzotriazine 1,4-dioxide derivatives Eur. J. Med. Chem. 46, 919-926
    • (2011) Eur. J. Med. Chem. , vol.46 , pp. 919-926
    • Xia, Q.1    Zhang, L.2    Zhang, J.3    Sheng, R.4    Yang, B.5    He, Q.6    Hu, Y.7
  • 2
  • 3
    • 53549100988 scopus 로고    scopus 로고
    • Differential enzymatic reductions governing the differential hypoxia-selective cytotoxicities of phenazine 5,10-dioxides
    • Lavaggi, M. L., Cabrera, M., González, M., and Cerecetto, H. (2008) Differential enzymatic reductions governing the differential hypoxia-selective cytotoxicities of phenazine 5,10-dioxides Chem. Res. Toxicol. 21, 1900-1906
    • (2008) Chem. Res. Toxicol. , vol.21 , pp. 1900-1906
    • Lavaggi, M.L.1    Cabrera, M.2    González, M.3    Cerecetto, H.4
  • 8
    • 79957534572 scopus 로고    scopus 로고
    • Targeting hypoxia in cancer therapy
    • Wilson, W. R. and Hay, M. P. (2011) Targeting hypoxia in cancer therapy Nat. Rev. Cancer 11, 393-409
    • (2011) Nat. Rev. Cancer , vol.11 , pp. 393-409
    • Wilson, W.R.1    Hay, M.P.2
  • 9
    • 35548961829 scopus 로고    scopus 로고
    • Tirapazamine: From the bench to clinical trials
    • Marcu, L. and Olver, I. (2006) Tirapazamine: from the bench to clinical trials Curr. Clin. Oncol. 1, 71-79
    • (2006) Curr. Clin. Oncol. , vol.1 , pp. 71-79
    • Marcu, L.1    Olver, I.2
  • 10
    • 33646454133 scopus 로고    scopus 로고
    • 18F]-misonidazole positron emission tomography-detected tumor hypoxia in patients with advanced head and neck cancer randomly assigned to chemoradiation with or without tirapazamine: A substudy of Trans-Tasman Radiation Oncology Group study 98.02
    • DOI 10.1200/JCO.2005.05.2878
    • 18F]- misonidazole positron emission tomography-detected tumor hypoxia in patients with advanced head and neck cancer randomly assigned to chemoradiation with or without tirapazamine: a substudy of Trans-Tasman Radiation Oncology Group Study 98.02 J. Clin. Oncol. 24, 2098-2104 (Pubitemid 46622121)
    • (2006) Journal of Clinical Oncology , vol.24 , Issue.13 , pp. 2098-2104
    • Rischin, D.1    Hicks, R.J.2    Fisher, R.3    Binns, D.4    Corry, J.5    Porceddu, S.6    Peters, L.J.7
  • 11
    • 77954600498 scopus 로고    scopus 로고
    • Tirapazamine, cisplatin, and radiation versus cisplatin and radiation for advanced squamous cell carcinoma of the head and neck (TROG 02.02, HeadSTART): A phase III trial of the trans-tasman radiation oncology group
    • Rischin, D., Peters, L. J., O'Sullivan, B., Giralt, J., Fisher, R., Yuen, K., Trotti, A., Bernier, J., Bourhis, J., Ringash, J., Henke, M., and Kenny, L. (2010) Tirapazamine, cisplatin, and radiation versus cisplatin and radiation for advanced squamous cell carcinoma of the head and neck (TROG 02.02, HeadSTART): a phase III trial of the trans-tasman radiation oncology group J. Clin. Oncol. 28, 2989-2995
    • (2010) J. Clin. Oncol. , vol.28 , pp. 2989-2995
    • Rischin, D.1    Peters, L.J.2    O'Sullivan, B.3    Giralt, J.4    Fisher, R.5    Yuen, K.6    Trotti, A.7    Bernier, J.8    Bourhis, J.9    Ringash, J.10    Henke, M.11    Kenny, L.12
  • 13
    • 0034830902 scopus 로고    scopus 로고
    • Redox-activated, hypoxia-selective DNA cleavage by quinoxaline 1,4-di-N-oxide
    • DOI 10.1016/S0968-0896(01)00163-8, PII S0968089601001638
    • Ganley, B., Chowdhury, G., Bhansali, J., Daniels, J. S., and Gates, K. S. (2001) Redox-activated, hypoxia-selective DNA cleavage by quinoxaline 1,4-di-N-oxide Bioorg. Med. Chem. 9, 2395-2401 (Pubitemid 32834628)
    • (2001) Bioorganic and Medicinal Chemistry , vol.9 , Issue.9 , pp. 2395-2401
    • Ganley, B.1    Chowdhury, G.2    Bhansali, J.3    Daniels J.Scott4    Gates, K.S.5
  • 14
    • 37049157552 scopus 로고
    • Bacterial inhibition by metabolite analogues. Part V. Reactions and antibacterial properties of p -diazine di-N-oxides
    • McIlwain, H. (1943) Bacterial inhibition by metabolite analogues. Part V. Reactions and antibacterial properties of p -diazine di-N-oxides J. Chem. Soc. part I) 322-327
    • (1943) J. Chem. Soc. , Issue.PART I , pp. 322-327
    • McIlwain, H.1
  • 15
    • 0015503670 scopus 로고
    • Antibacterial properties of quindoxin: A new growth promoting agent
    • Hennessey, T. D. and Edwards, J. R. (1972) Antibacterial properties of quindoxin: a new growth promoting agent Vet. Rec. 90, 187-190
    • (1972) Vet. Rec. , vol.90 , pp. 187-190
    • Hennessey, T.D.1    Edwards, J.R.2
  • 16
    • 0018086175 scopus 로고
    • Mode of action of quindoxin and substituted quinoxaline-di-N-oxides on Escherichia coli
    • Suter, W., Rosselet, A., and Knusel, F. (1978) Mode of action of quindoxin and substituted quinoxaline-di- N -oxides on E. coli Antimicrob. Agents Chemother. 13, 770-783 (Pubitemid 8323547)
    • (1978) Antimicrobial Agents and Chemotherapy , vol.13 , Issue.5 , pp. 770-783
    • Suter, W.1    Rosselet, A.2    Knuesel, F.3
  • 17
    • 0029959194 scopus 로고    scopus 로고
    • The one-electron reduction potential of 3-amino-1,2,4-benzotriazine l,4-dioxide (tirapazamine): A hypoxia-selective bioreductive drug
    • Priyadarsini, K. I., Tracy, M., and Wardman, P. (1996) The one-electron reduction potential of 3-amino-1,2,4-benzotriazine 1,4-dioxide (tirapazamine): A hypoxia-selective bioreductive drug Free Radical Res. 25, 393-399 (Pubitemid 26379055)
    • (1996) Free Radical Research , vol.25 , Issue.5 , pp. 393-399
    • Priyadarsini, K.I.1    Tracy, M.2    Wardman, P.3
  • 18
    • 0026047102 scopus 로고
    • Microsomal reduction of 3-amino-1,2,4,-benzotriazine 1,4-dioxide to a free radical
    • Lloyd, R. V., Duling, D. R., Rumyantseva, G. V., Mason, R. P., and Bridson, P. K. (1991) Microsomal reduction of 3-amino-1,2,4,-benzotriazine 1,4-dioxide to a free radical Mol. Pharmacol. 40, 440-445
    • (1991) Mol. Pharmacol. , vol.40 , pp. 440-445
    • Lloyd, R.V.1    Duling, D.R.2    Rumyantseva, G.V.3    Mason, R.P.4    Bridson, P.K.5
  • 20
    • 0023929181 scopus 로고
    • Molecular mechanisms for the hypoxia-dependent activation of 3-amino-1,2,4-benzotriazine-1,4-dioxide (SR 4233)
    • DOI 10.1016/0006-2952(88)90010-X
    • Laderoute, K. L., Wardman, P., and Rauth, M. (1988) Molecular mechanisms for the hypoxia-dependent activation of 3-amino-1,2,4-benzotriazine 1,4-dioxide (SR4233) Biochem. Pharmacol. 37, 1487-1495 (Pubitemid 18093342)
    • (1988) Biochemical Pharmacology , vol.37 , Issue.8 , pp. 1487-1495
    • Laderoute, K.1    Wardman, P.2    Rauth, M.3
  • 21
    • 0027248915 scopus 로고
    • Molecular mechanisms of SR 4233-induced hepatocyte toxicity under aerobic versus hypoxic conditions
    • Silva, J. M. and O'Brien, P. J. (1993) Molecular mechanisms of SR 4233-induced hepatocyte toxicity under aerobic versus hypoxic conditions Br. J. Cancer 68, 484-491 (Pubitemid 23258450)
    • (1993) British Journal of Cancer , vol.68 , Issue.3 , pp. 484-491
    • Silva, J.M.1    O'Brien, P.J.2
  • 22
    • 0022528195 scopus 로고
    • Identification of two major reduction products of the hypoxic cell toxin 3-amino-1,2,4-benzotriazine-1,4-dioxide
    • DOI 10.1016/0006-2952(86)90448-X
    • Laderoute, K. and Rauth, A. M. (1986) Identification of two major reduction products of the hypoxic cell toxin 3-amino-1,2,4-benzotriazine-1,4- dioxide Biochem. Pharmacol. 35, 3417-3420 (Pubitemid 16001459)
    • (1986) Biochemical Pharmacology , vol.35 , Issue.19 , pp. 3417-3420
    • Laderoute, K.R.1    Rauth, A.M.2
  • 23
    • 0027524919 scopus 로고
    • Pharmacokinetics and bioreductive metabolism of the novel benzotriazine di-N-oxide hypoxic cell cytotoxin tirapazamine (WIN 59075; SR 4233; NSC 130181) in mice
    • Walton, M. I. and Workman, P. (1993) Pharmacokinetics and bioreductive metabolism of the novel benzotriazine di- N -oxide hypoxic cell cytotoxin tirapazamine (WIN 59075, SR 4233, NSC 130181) in mice J. Pharmacol. Exp. Ther. 265, 938-947 (Pubitemid 23315608)
    • (1993) Journal of Pharmacology and Experimental Therapeutics , vol.265 , Issue.2 , pp. 938-947
    • Walton, M.I.1    Workman, P.2
  • 24
    • 0022493495 scopus 로고
    • SR-4233: A new bioreductive agent with high selective toxicity for hypoxic mammalian cells
    • Zeman, E. M., Brown, J. M., Lemmon, M. J., Hirst, V. K., and Lee, W. W. (1986) SR 4233: a new bioreductive agent with high selective toxicity for hypoxic mammalian cells Int. J. Radiat. Oncol. Biol. Phys. 12, 1239-1242 (Pubitemid 16055893)
    • (1986) International Journal of Radiation Oncology Biology Physics , vol.12 , Issue.7 , pp. 1239-1242
    • Zeman, E.M.1    Brown, J.M.2    Lemmon, M.J.3
  • 26
    • 0027288316 scopus 로고
    • SR 4233 (tirapazamine): A new anticancer drug exploiting hypoxia in solid tumours
    • Brown, J. M. (1993) SR4233 (Tirapazamine): a new anticancer drug exploiting hypoxia in solid tumours Br. J. Cancer 67, 1163-1170 (Pubitemid 23172847)
    • (1993) British Journal of Cancer , vol.67 , Issue.6 , pp. 1163-1170
    • Brown, J.M.1
  • 29
    • 0029959898 scopus 로고    scopus 로고
    • DNA cleavage by the antitumor agent 3-amino-1,2,4-benzotriazine 1,4-dioxide (SR4233): Evidence for involvement of hydroxyl radical
    • DOI 10.1021/ja9510774
    • Daniels, J. S. and Gates, K. S. (1996) DNA cleavage by the antitumor agent 3-amino-1,2,4-benzotriazine 1,4-dioxide (SR4233): evidence for involvement of hydroxyl radical J. Am. Chem. Soc. 118, 3380-3385 (Pubitemid 26145092)
    • (1996) Journal of the American Chemical Society , vol.118 , Issue.14 , pp. 3380-3385
    • Daniels, J.S.1    Gates, K.S.2
  • 30
    • 61749095311 scopus 로고    scopus 로고
    • Initiation of DNA strand cleavage by 1,2,4-benzotriazine 1,4-dioxides: Mechanistic insight from studies of 3-methyl-1,2,4-benzotriazine 1,4-dioxide
    • Junnotula, V., Sarkar, U., Sinha, S., and Gates, K. S. (2009) Initiation of DNA strand cleavage by 1,2,4-benzotriazine 1,4-dioxides: mechanistic insight from studies of 3-methyl-1,2,4-benzotriazine 1,4-dioxide J. Am. Chem. Soc. 131, 1015-1024
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 1015-1024
    • Junnotula, V.1    Sarkar, U.2    Sinha, S.3    Gates, K.S.4
  • 32
    • 3042544368 scopus 로고    scopus 로고
    • Oxidation of 2-deoxyribose by benzotriazinyl radicals of antitumor 3-amino-1,2,4-benzotriazine 1,4-dioxides
    • DOI 10.1021/ja048740l
    • Shinde, S. S., Anderson, R. F., Hay, M. P., Gamage, S. A., and Denny, W. A. (2004) Oxidation of 2-deoxyribose by benzotriazinyl radicals of antitumor 3-amino-1,2,4-benzotriazine 1,4-dioxides J. Am. Chem. Soc. 126, 7865-7874 (Pubitemid 38812777)
    • (2004) Journal of the American Chemical Society , vol.126 , Issue.25 , pp. 7865-7874
    • Shinde, S.S.1    Anderson, R.F.2    Hay, M.P.3    Gamage, S.A.4    Denny, W.A.5
  • 33
    • 70349921764 scopus 로고    scopus 로고
    • Spin trapping of radicals other than the hydroxyl radical upon reduction of the anticancer agent tirapazamine by cytochrome P450 reductase
    • Shinde, S. S., Hay, M. P., Patterson, A. V., Denny, W. A., and Anderson, R. F. (2009) Spin trapping of radicals other than the hydroxyl radical upon reduction of the anticancer agent tirapazamine by cytochrome P450 reductase J. Am. Chem. Soc. 131, 14220-14221
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 14220-14221
    • Shinde, S.S.1    Hay, M.P.2    Patterson, A.V.3    Denny, W.A.4    Anderson, R.F.5
  • 34
    • 77649287770 scopus 로고    scopus 로고
    • Characterization of radicals formed following enzymatic reduction of 3-substituted analogues of the hypoxia-selective cytotoxin 3-amino-1,2,4- benzotriazine 1,4-dioxide (tirapazamine)
    • Shinde, S. S., Maroz, A., Hay, M. P., Patterson, A. V., Denny, W. A., and Anderson, R. F. (2010) Characterization of radicals formed following enzymatic reduction of 3-substituted analogues of the hypoxia-selective cytotoxin 3-amino-1,2,4-benzotriazine 1,4-dioxide (tirapazamine) J. Am. Chem. Soc. 132, 2591-2599
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 2591-2599
    • Shinde, S.S.1    Maroz, A.2    Hay, M.P.3    Patterson, A.V.4    Denny, W.A.5    Anderson, R.F.6
  • 35
    • 0037460188 scopus 로고    scopus 로고
    • Activation of 3-amino-1,2,4-benzotriazine 1,4-dioxide antitumor agents to oxidizing species following their one-electron reduction
    • DOI 10.1021/ja0209363
    • Anderson, R. F., Shinde, S. S., Hay, M. P., Gamage, S. A., and Denny, W. A. (2003) Activation of 3-amino-1,2,4-benzotriazine 1,4-dioxide antitumor agents to oxidizing species following their one-electron Reduction J. Am. Chem. Soc. 125, 748-756 (Pubitemid 36109936)
    • (2003) Journal of the American Chemical Society , vol.125 , Issue.3 , pp. 748-756
    • Anderson, R.F.1    Shinde, S.S.2    Hay, M.P.3    Gamage, S.A.4    Denny, W.A.5
  • 36
    • 20844438807 scopus 로고    scopus 로고
    • Radical properties governing the hypoxia-selective cytotoxicity of antitumor 3-amino-1,2,4-benzotriazine 1,4-dioxidest
    • DOI 10.1039/b502586a
    • Anderson, R. F., Shinde, S. S., Hay, M. P., Gamage, S. A., and Denny, W. A. (2005) Radical properties governing the hypoxia-selective cytotoxicity of antitumor 3-amino-1,2,4-benzotriazine 1,4-dioxides Org. Biomol. Chem. 3, 2167-2174 (Pubitemid 40859896)
    • (2005) Organic and Biomolecular Chemistry , vol.3 , Issue.11 , pp. 2167-2174
    • Anderson, R.F.1    Shinde, S.S.2    Hay, M.P.3    Gamage, S.A.4    Denny, W.A.5
  • 37
    • 0035847180 scopus 로고    scopus 로고
    • 3-amino-1,2,4-benzotriazine 4-oxide: Characterization of a new metabolite arising from bioreductive processing of the antitumor agent 3-amino-1,2,4-benzotriazine 1,4-dioxide (tirapazamine)
    • DOI 10.1021/jo001232j
    • Fuchs, T., Chowdhary, G., Barnes, C. L., and Gates, K. S. (2001) 3-Amino-1,2,4-benzotriazine 4-oxide: characterization of a new metabolite arising from bioreductive processing of the antitumor agent 3-amino-1,2,4- benzotriazine 1,4-dioxide (tirapazamine) J. Org. Chem. 66, 107-114 (Pubitemid 32057846)
    • (2001) Journal of Organic Chemistry , vol.66 , Issue.1 , pp. 107-114
    • Fuchs, T.1    Chowdhury, G.2    Barnes, C.L.3    Gates, K.S.4
  • 38
    • 14444277952 scopus 로고
    • On a new antibiotic, emimycin. II. on the structure of emimycin
    • Terao, M. (1963) On a new antibiotic, emimycin. II. On the structure of emimycin J. Antibiot. (Tokyo), Sec. A 16, 182-186
    • (1963) J. Antibiot. (Tokyo), Sec. A , vol.16 , pp. 182-186
    • Terao, M.1
  • 39
    • 85008067739 scopus 로고
    • Studies on the constituents of Ailanthus altissima Swingle. on the alkaloidal constituents
    • Ohmoto, T., Tanaka, R., and Nikaido, T. (1976) Studies on the constituents of Ailanthus altissima Swingle. On the alkaloidal constituents Chem. Pharm. Bull. 24, 1532-1536
    • (1976) Chem. Pharm. Bull. , vol.24 , pp. 1532-1536
    • Ohmoto, T.1    Tanaka, R.2    Nikaido, T.3
  • 40
    • 0000720490 scopus 로고
    • The structure of orellanine and orelline
    • Antkowiak, W. Z. and Gessner, W. P. (1979) The structure of orellanine and orelline Tetrahedron Lett. 20, 1931-1934
    • (1979) Tetrahedron Lett. , vol.20 , pp. 1931-1934
    • Antkowiak, W.Z.1    Gessner, W.P.2
  • 42
    • 0035094418 scopus 로고    scopus 로고
    • Cortamidine oxide, a novel disulfide metabolite from the New Zealand basidiomycete (mushroom) cortinarius species
    • DOI 10.1021/np000408+
    • Nicholas, G. M., Blunt, J. W., and Munro, M. H. G. (2001) Cortamidine oxide, a novel disulfide metabolite from the New Zealand Basidiomycete (mushroom) Cortinarius species J. Nat. Prod. 64, 341-344 (Pubitemid 32249799)
    • (2001) Journal of Natural Products , vol.64 , Issue.3 , pp. 341-344
    • Nicholas, G.M.1    Blunt, J.W.2    Munro, M.H.G.3
  • 44
    • 0013895661 scopus 로고
    • A wide spectrum antibiotic produced by a species of Sorangium
    • Peterson, E. A., Gillespie, D. C., and Cook, F. D. (1966) A wide spectrum antibiotic produced by a species of Sorangium Can. J. Microbiol. 12, 221-230
    • (1966) Can. J. Microbiol. , vol.12 , pp. 221-230
    • Peterson, E.A.1    Gillespie, D.C.2    Cook, F.D.3
  • 46
    • 0015609260 scopus 로고
    • Sensitivity to myxin of Escherichia coli treated with ethylenediaminetetraacetic acid
    • Lesley, S. M. and Behki, R. M. (1973) Sensitivity to myxin of Escherichia coli treated with ethylenediaminetetraacetic acid Can. J. Microbiol. 19, 531-533
    • (1973) Can. J. Microbiol. , vol.19 , pp. 531-533
    • Lesley, S.M.1    Behki, R.M.2
  • 48
    • 0015253066 scopus 로고
    • Deoxyribnucleic acid degradation and the lethal effect by myxin in E. coli
    • Behki, R. M. and Lesley, S. M. (1972) Deoxyribnucleic acid degradation and the lethal effect by myxin in E. coli J. Bacteriol. 109, 250-261
    • (1972) J. Bacteriol. , vol.109 , pp. 250-261
    • Behki, R.M.1    Lesley, S.M.2
  • 49
    • 0015502608 scopus 로고
    • Inhibition of ribonucleic acid synthesis by myxin
    • Hollstein, U. and Butler, P. L. (1972) Inhibition of ribonucleic acid synthesis by myxin Biochemistry 11, 1345-1350
    • (1972) Biochemistry , vol.11 , pp. 1345-1350
    • Hollstein, U.1    Butler, P.L.2
  • 50
    • 0015766317 scopus 로고
    • Comparison of hycanthone(Etrenol), some hycanthone analogs, myxin, and 4-nitroquinoline 1-oxide as frameshift mutagens
    • Hartman, P. E., Berger, H., and Hartman, Z. (1973) Comparison of hycanthone(Etrenol), some hycanthone analogs, myxin, and 4-nitroquinoline 1-oxide as frameshift mutagens J. Pharmacol. Exp. Ther. 186, 390-398
    • (1973) J. Pharmacol. Exp. Ther. , vol.186 , pp. 390-398
    • Hartman, P.E.1    Berger, H.2    Hartman, Z.3
  • 51
    • 0015207544 scopus 로고
    • Interaction of phenazines with polydeoxyribonucleotides
    • Hollstein, U. and Van Gemert, R. J. J. (1971) Interaction of phenazines with polydeoxyribonucleotides Biochemistry 10, 497-504
    • (1971) Biochemistry , vol.10 , pp. 497-504
    • Hollstein, U.1    Van Gemert, R.J.J.2
  • 52
    • 0014171125 scopus 로고
    • Mode of action of myxin on Escherichia coli
    • Lesley, S. M. and Behki, R. M. (1967) Mode of action of myxin on Escherichia coli J. Bacteriol. 94, 1837-1845
    • (1967) J. Bacteriol. , vol.94 , pp. 1837-1845
    • Lesley, S.M.1    Behki, R.M.2
  • 53
    • 0008235020 scopus 로고
    • The Wohl-Aue reaction. I. Structure of benzo [a] phenazine oxides and syntheses of 1,6-dimethoxyphenazine and 1,6-dichlorophenazine
    • Pachter, I. J. and Kloetzel, M. C. (1951) The Wohl-Aue reaction. I. Structure of benzo [a] phenazine oxides and syntheses of 1,6-dimethoxyphenazine and 1,6-dichlorophenazine J. Am. Chem. Soc. 73, 4958-4961
    • (1951) J. Am. Chem. Soc. , vol.73 , pp. 4958-4961
    • Pachter, I.J.1    Kloetzel, M.C.2
  • 55
    • 0010701954 scopus 로고
    • N-Dioxides, a new class of amine oxides
    • Edwards, O. E. and Gillespie, D. C. (1966) N-Dioxides, a new class of amine oxides Tetrahedron Lett. 40, 4867-4870
    • (1966) Tetrahedron Lett. , vol.40 , pp. 4867-4870
    • Edwards, O.E.1    Gillespie, D.C.2
  • 56
    • 0014413509 scopus 로고
    • The interaction of closed circular DNA with intercalative dyes. I. the superhelix density of SV40 DNA in the presence and absence of dye
    • Bauer, W. and Vinograd, J. (1968) The interaction of closed circular DNA with intercalative dyes. I. The superhelix density of SV40 DNA in the presence and absence of dye J. Mol. Biol. 33, 141-171
    • (1968) J. Mol. Biol. , vol.33 , pp. 141-171
    • Bauer, W.1    Vinograd, J.2
  • 58
    • 4644348540 scopus 로고
    • Über die Einwirkung von Nitrobenzol auf Anilin bei Gegenwart von Alkali
    • Wohl, A. and Aue, W. (1901) Über die Einwirkung von Nitrobenzol auf Anilin bei Gegenwart von Alkali Chem. Ber. 34, 2442-2450
    • (1901) Chem. Ber. , vol.34 , pp. 2442-2450
    • Wohl, A.1    Aue, W.2
  • 59
    • 37049175468 scopus 로고
    • The constitution of the pigment of Chromobacterium iodinum
    • Clemo, G. R. and Daglish, A. F. (1950) The constitution of the pigment of Chromobacterium iodinum J. Chem. Soc. 1481-1485
    • (1950) J. Chem. Soc. , pp. 1481-1485
    • Clemo, G.R.1    Daglish, A.F.2
  • 60
    • 0017672745 scopus 로고
    • Electrophoresis of DNA in agarose gels. Optimizing separations of conformational isomers of double and single-stranded DNAs
    • Jonson, P. H. and Grossman, L. I. (1977) Electrophoresis of DNA in agarose gels. Optimizing separations of conformational isomers of double and single-stranded DNAs Biochemistry 16, 4217-4224
    • (1977) Biochemistry , vol.16 , pp. 4217-4224
    • Jonson, P.H.1    Grossman, L.I.2
  • 61
    • 0021986125 scopus 로고
    • Quantitative measurement of single- and double-strand breakage of DNA in Escherichia coli by the antitumor antibiotics bleomycin and talisomycin
    • Mirabelli, C. K., Huang, C. H., Fenwick, R. G., and Crooke, S. T. (1985) Quantitative measurement of single- and double-strand breakage of DNA in Escherichia coli by the antitumor antibiotics bleomycin and talisomycin Antimicrob. Agents Chemother. 27, 460-467 (Pubitemid 15097639)
    • (1985) Antimicrobial Agents and Chemotherapy , vol.27 , Issue.4 , pp. 460-467
    • Mirabelli, C.K.1    Huang, C.-H.2    Fenwick, R.G.3    Crooke, S.T.4
  • 62
    • 0019886153 scopus 로고
    • Separation of closed circular DNA from linear DNA by electrophoresis in two dimensions in agarose gels
    • Oppenheim, A. (1981) Separation of closed circular DNA from linear DNA by electrophoresis in two dimensions in agarose gels Nucleic Acids Res. 9, 6805-6812
    • (1981) Nucleic Acids Res. , vol.9 , pp. 6805-6812
    • Oppenheim, A.1
  • 63
    • 0019445345 scopus 로고
    • Simple procedure for distinguishing CCC, OC, and L forms of plasmid DNA by agarose gel electrophoresis
    • DOI 10.1016/0147-619X(81)90012-3
    • Hintermann, G., Fischer, H. M., Crameri, R., and Hutter, R. (1981) Simple procedure for distinguishing CCC, OC, and L forms of plasmid DNA by agarose gel electrophoresis Plasmid 5, 371-373 (Pubitemid 11035706)
    • (1981) Plasmid , vol.5 , Issue.3 , pp. 371-373
    • Hintermann, G.1    Fischer, H.M.2    Crameri, R.3    Hutter, R.4
  • 64
    • 0029862714 scopus 로고    scopus 로고
    • Dual action of tirapazamine in the induction of DNA strand breaks
    • Jones, G. D. D. and Weinfeld, M. (1996) Dual action of tirapazamine in the induction of DNA strand breaks Cancer Res. 56, 1584-1590 (Pubitemid 26104022)
    • (1996) Cancer Research , vol.56 , Issue.7 , pp. 1584-1590
    • Jones, G.D.D.1    Weinfeld, M.2
  • 65
    • 8844256506 scopus 로고    scopus 로고
    • Enzyme-activated, hypoxia-selective DNA damage by 3-amino-2- quinoxalinecarbonitrile 1,4-di-N-oxide
    • DOI 10.1021/tx049836w
    • Chowdhury, G., Kotandeniya, D., Barnes, C. L., and Gates, K. S. (2004) Enzyme-activated, hypoxia-selective DNA damage by 3-amino-2- quinoxalinecarbonitrile 1,4-di-N-oxide Chem. Res. Toxicol. 17, 1399-1405 (Pubitemid 39532308)
    • (2004) Chemical Research in Toxicology , vol.17 , Issue.11 , pp. 1399-1405
    • Chowdhury, G.1    Kotandeniya, D.2    Daniels, J.S.3    Barnes, C.L.4    Gates, K.S.5
  • 66
    • 77951204822 scopus 로고    scopus 로고
    • DNA strand cleaving properties and hypoxia-selective cytotoxicity of 7-chloro-2-thienylcarbonyl-3-trifluoromethylquinoxaline 1,4-dioxide
    • Junnotula, V., Rajapakse, A., Abrillaga, L., Lopez de Cerain, A., Solano, B., Villar, R., Monge, A., and Gates, K. S. (2010) DNA strand cleaving properties and hypoxia-selective cytotoxicity of 7-chloro-2-thienylcarbonyl-3- trifluoromethylquinoxaline 1,4-dioxide Bioorg. Med. Chem. 18, 3125-3132
    • (2010) Bioorg. Med. Chem. , vol.18 , pp. 3125-3132
    • Junnotula, V.1    Rajapakse, A.2    Abrillaga, L.3    Lopez De Cerain, A.4    Solano, B.5    Villar, R.6    Monge, A.7    Gates, K.S.8
  • 67
    • 0033388928 scopus 로고    scopus 로고
    • Photosensitization of guanine-specific DNA damage by a cyano-substituted quinoxaline di-N-oxide
    • DOI 10.1021/tx990149s
    • Fuchs, T., Gates, K. S., Hwang, J.-T., and Greenberg, M. M. (1999) Photosensitization of guanine-specific DNA damage by a cyano-substituted quinoxaline di- N -oxide Chem. Res. Toxicol. 12, 1190-1194 (Pubitemid 30013529)
    • (1999) Chemical Research in Toxicology , vol.12 , Issue.12 , pp. 1190-1194
    • Fuchs, T.1    Gates, K.S.2    Hwang, J.-T.3    Greenberg, M.M.4
  • 68
    • 0032567479 scopus 로고    scopus 로고
    • Photochemical DNA cleavage by the antitumor agent 3-amino-1,2,4- benzotriazine 1,4-dioxide (tirapazamine, WIN 59075, SR4233)
    • DOI 10.1021/jo981314w
    • Daniels, J. S., Chatterji, T., MacGillivray, L. R., and Gates, K. S. (1998) Photochemical DNA cleavage by the antitumor agent 3-amino-1,2,4- benzotriazine 1,4-dioxide (Tirapazamine, WIN 59075, SR4233) J. Org. Chem. 63, 10027-10030 (Pubitemid 29035172)
    • (1998) Journal of Organic Chemistry , vol.63 , Issue.26 , pp. 10027-10030
    • Daniels, J.S.1    Chatterji, T.2    MacGillivray, L.R.3    Gates, K.S.4
  • 69
    • 0030954581 scopus 로고    scopus 로고
    • A model of the interaction of substrates and inhibitors with xanthine oxidase
    • DOI 10.1021/ja962309h
    • Rastelli, G., Costantino, L., and Albasini, A. (1997) A model of the interaction of substrates and inhibitors with xanthine oxidase J. Am. Chem. Soc. 119, 3007-3016 (Pubitemid 27204515)
    • (1997) Journal of the American Chemical Society , vol.119 , Issue.13 , pp. 3007-3016
    • Rastelli, G.1    Costantino, L.2    Albasini, A.3
  • 70
    • 0018246504 scopus 로고
    • Oxidation of quinazoline and quinoxaline by xanthine oxidase and aldehyde oxidase
    • McCormack, J. J., Allen, B. A., and Hodnett, C. N. (1978) Oxidation of quinazoline and quinoxaline by xanthine oxidase and aldehyde oxidase J. Heterocyclic Chem. 15, 1249-1254 (Pubitemid 9104810)
    • (1978) Journal of Heterocyclic Chemistry , vol.15 , Issue.8 , pp. 1249-1254
    • McCormack, J.J.1    Allen, B.A.2    Hodnett, C.N.3
  • 71
    • 0015359969 scopus 로고
    • A comparison of the specificities of xanthine oxidase and aldehyde oxidase
    • Krenitsky, T. A., Neil, S. M., Elion, G. B., and Hitchings, G. H. (1972) A comparison of the specificities of xanthine oxidase and aldehyde oxidase Arch. Biochem. Biophys. 150, 585-599
    • (1972) Arch. Biochem. Biophys. , vol.150 , pp. 585-599
    • Krenitsky, T.A.1    Neil, S.M.2    Elion, G.B.3    Hitchings, G.H.4
  • 72
    • 0019532613 scopus 로고
    • DNA strand scission by enzymatically generated oxygen radicals
    • Brawn, K. and Fridovich, I. (1981) DNA strand scission by enzymatically generated oxygen radicals Arch. Biochem. Biophys. 206, 414-419
    • (1981) Arch. Biochem. Biophys. , vol.206 , pp. 414-419
    • Brawn, K.1    Fridovich, I.2
  • 73
    • 0025126555 scopus 로고
    • Role of free radicals and catalytic metal ions in human disease: An overview
    • DOI 10.1016/0076-6879(90)86093-B
    • Halliwell, B. and Gutteridge, J. M. C. (1990) Role of free radicals and catalytic metal ions in human disease: an overview Methods Enzymol. 186, 1-85 (Pubitemid 20279941)
    • (1990) Methods in Enzymology , vol.186 , pp. 1-85
    • Halliwell, B.1    Gutteridge, J.M.C.2
  • 74
    • 0025820862 scopus 로고
    • Allopurinol-insensitive oxygen radical formation by milk xanthine oxidase systems
    • Nakamura, M. (1991) Allopurinol-insensitive oxygen radical formation by milk xanthine oxidase systems J. Biochem. 110, 450-456
    • (1991) J. Biochem. , vol.110 , pp. 450-456
    • Nakamura, M.1
  • 75
    • 0031573471 scopus 로고    scopus 로고
    • Comparison of oxygen radical generation from the reductive activation of doxorubicin, streptonigrin, and menadione by xanthine oxidase and xanthine dehydrogenase
    • DOI 10.1006/abbi.1997.0340
    • Yee, S. B. and Pritsos, C. A. (1997) Comparison of oxygen radical generation from the reductive activation of doxorubicin, streptonigrin, and menadione by xanthine oxidase and xanthine dehydrogenase Arch. Biochem. Biophys. 347, 235-241 (Pubitemid 27492794)
    • (1997) Archives of Biochemistry and Biophysics , vol.347 , Issue.2 , pp. 235-241
    • Yee, S.B.1    Pritsos, C.A.2
  • 76
    • 49549167210 scopus 로고
    • Electrochemical characterization of 6-methoxy-1-phenazinol-5,10-dioxide
    • Donahue, J. J. and Oliveri-Vigh, S. (1973) Electrochemical characterization of 6-methoxy-1-phenazinol-5,10-dioxide Anal. Chim. Acta 63, 415-425
    • (1973) Anal. Chim. Acta , vol.63 , pp. 415-425
    • Donahue, J.J.1    Oliveri-Vigh, S.2
  • 78
    • 0033607196 scopus 로고    scopus 로고
    • Reaction of the hypoxia-selective antitumor agent tirapazamine with a C1′-radical in single-stranded and double-stranded DNA: The drug and its metabolites can serve as surrogates for molecular oxygen in radical-mediated DNA damage reactions
    • Hwang, J.-T., Greenberg, M. M., Fuchs, T., and Gates, K. S. (1999) Reaction of the hypoxia-selective antitumor agent tirapazamine with a C1′-radical in single-stranded and double-stranded DNA: the drug and its metabolites can serve as surrogates for molecular oxygen in radical-mediated DNA damage reactions Biochemistry 38, 14248-14255
    • (1999) Biochemistry , vol.38 , pp. 14248-14255
    • Hwang, J.-T.1    Greenberg, M.M.2    Fuchs, T.3    Gates, K.S.4
  • 79
    • 0036495885 scopus 로고    scopus 로고
    • Mimicking metallophosphatases: Revealing a role for an OH group with no libido
    • DOI 10.1002/1521-3773(20020301)41: 5<849::AID-ANIE849>3.0.CO;2-7
    • Forconi, M. and Williams, N. H. (2002) Mimicking metallophosphatases: revealing a role for an OH group with no libido Angew. Chem., Int. Ed. Engl. 41, 849-852 (Pubitemid 34218544)
    • (2002) Angewandte Chemie - International Edition , vol.41 , Issue.5 , pp. 849-852
    • Forconi, M.1    Williams, N.H.2
  • 81
    • 0037134157 scopus 로고    scopus 로고
    • Aerobic oxidation of N-alkylamides catalyzed by N-hydroxyphthalimide under mild conditions. Polar and enthalpic effects
    • DOI 10.1021/jo016398e
    • Minisci, F., Punta, C., Recupero, F., Fontana, F., and Pedulli, G. F. (2002) Aerobic oxidation of N-alkylamides catalyzed by N-hydroxyphthalimide under mild conditions. Polar and enthalic effects J. Org. Chem. 67, 2671-2676 (Pubitemid 34298884)
    • (2002) Journal of Organic Chemistry , vol.67 , Issue.8 , pp. 2671-2676
    • Minisci, F.1    Punta, C.2    Recupero, F.3    Fontana, F.4    Franco Pedulli, G.5
  • 82
    • 0024318885 scopus 로고
    • The effect of oxygen, antioxidants, and superoxide radical on tyrosine phenoxyl radical dimerization
    • DOI 10.1016/0891-5849(89)90064-6
    • Hunter, E. P. L, Derosiers, M. F., and Simic, M. G. (1989) The effect of oxygen, antioxidants, and superoxide radical on tyrosine phenoxyl radical dimerization Free Radical Biol. Med. 6, 581-585 (Pubitemid 19147807)
    • (1989) Free Radical Biology and Medicine , vol.6 , Issue.6 , pp. 581-585
    • Hunter, E.P.L.1    Desrosiers, M.F.2    Simic, M.G.3
  • 83
    • 0034973773 scopus 로고    scopus 로고
    • Common and uncommon cytochrome P450 reactions related to metabolism and chemical toxicity
    • Guengerich, F. P. (2001) Common and uncommon cytochrome P450 reactions related to metabolism and chemical toxicity Chem. Res. Toxicol. 14, 611-650 (Pubitemid 32565712)
    • (2001) Chemical Research in Toxicology , vol.14 , Issue.6 , pp. 611-650
    • Guengerich, F.P.1
  • 84
    • 0021762388 scopus 로고
    • Cleavage of DNA with methidiumpropyl-EDTA-Iron(II): Reaction conditions and product analyses
    • Hertzberg, R. P. and Dervan, P. B. (1984) Cleavage of DNA with methidiumpropyl-EDTA-Iron(II): Reaction conditions and product analyses Biochemistry 23, 3934-3945
    • (1984) Biochemistry , vol.23 , pp. 3934-3945
    • Hertzberg, R.P.1    Dervan, P.B.2


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