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Volumn 403, Issue 1, 2012, Pages 309-321

LC-MS/MS identification of the principal in vitro and in vivo phase i metabolites of the novel thiosemicarbazone anti-cancer drug, Bp4eT

Author keywords

2 Benzoylpyridine 4 ethyl 3 thiosemicarbazone; Anti cancer; Anti tumor chemotherapeutic; Bp4eT; LC MS

Indexed keywords

2-BENZOYLPYRIDINE-4-ETHYL-3-THIOSEMICARBAZONE; ANTI-CANCER; ANTI-TUMORS; BP4ET; LC-MS;

EID: 84858748865     PISSN: 16182642     EISSN: 16182650     Source Type: Journal    
DOI: 10.1007/s00216-012-5766-4     Document Type: Article
Times cited : (16)

References (39)
  • 1
    • 84858765320 scopus 로고    scopus 로고
    • GLOBOCAN Accessed19Oct2011
    • GLOBOCAN 2008 (IARC) Section of Cancer Information WHO http://www.who.int/mediacentre/factsheets/fs297/en/. Accessed 19 Oct 2011
    • (2008) (IARC) Section of Cancer Information WHO
  • 3
    • 67349137868 scopus 로고    scopus 로고
    • Cancer cell iron metabolism and the development of potent iron chelators as anti-tumour agents
    • 10.1016/j.bbagen.2008.04.003 1:CAS:528:DC%2BD1MXnt1yjurg%3D
    • DR Richardson DS Kalinowski S Lau PJ Jansson DB Lovejoy 2009 Cancer cell iron metabolism and the development of potent iron chelators as anti-tumour agents Biochim Biophys Acta 1790 702 717 10.1016/j.bbagen.2008.04.003 1:CAS:528:DC%2BD1MXnt1yjurg%3D
    • (2009) Biochim Biophys Acta , vol.1790 , pp. 702-717
    • Richardson, D.R.1    Kalinowski, D.S.2    Lau, S.3    Jansson, P.J.4    Lovejoy, D.B.5
  • 4
    • 0038324398 scopus 로고    scopus 로고
    • The role of iron chelation in cancer therapy
    • 10.2174/0929867033457638 1:CAS:528:DC%2BD3sXjs1yjtb8%3D
    • JL Buss FM Torti SV Torti 2003 The role of iron chelation in cancer therapy Curr Med Chem 10 1021 1034 10.2174/0929867033457638 1:CAS:528: DC%2BD3sXjs1yjtb8%3D
    • (2003) Curr Med Chem , vol.10 , pp. 1021-1034
    • Buss, J.L.1    Torti, F.M.2    Torti, S.V.3
  • 5
    • 10644257442 scopus 로고    scopus 로고
    • Iron chelators in cancer chemotherapy
    • 10.2174/1568026043387269 1:CAS:528:DC%2BD2cXhtVKmsbvJ
    • JL Buss BT Greene J Turner FM Torti SV Torti 2004 Iron chelators in cancer chemotherapy Curr Top Med Chem 4 1623 1635 10.2174/1568026043387269 1:CAS:528:DC%2BD2cXhtVKmsbvJ
    • (2004) Curr Top Med Chem , vol.4 , pp. 1623-1635
    • Buss, J.L.1    Greene, B.T.2    Turner, J.3    Torti, F.M.4    Torti, S.V.5
  • 6
    • 33749515083 scopus 로고    scopus 로고
    • A class of iron chelators with a wide spectrum of potent antitumor activity that overcomes resistance to chemotherapeutics
    • 10.1073/pnas.0604979103 1:CAS:528:DC%2BD28XhtVyhu7jL
    • M Whitnall J Howard P Ponka DR Richardson 2006 A class of iron chelators with a wide spectrum of potent antitumor activity that overcomes resistance to chemotherapeutics Proc Natl Acad Sci U S A 103 14901 14906 10.1073/pnas. 0604979103 1:CAS:528:DC%2BD28XhtVyhu7jL
    • (2006) Proc Natl Acad Sci U S A , vol.103 , pp. 14901-14906
    • Whitnall, M.1    Howard, J.2    Ponka, P.3    Richardson, D.R.4
  • 7
    • 0035181433 scopus 로고    scopus 로고
    • Inhibition of malignant cell growth by 311, a novel iron chelator of the pyridoxal isonicotinoyl hydrazone class: Effect on the R2 subunit of ribonucleotide reductase
    • 1:CAS:528:DC%2BD3MXptFaisLg%3D
    • DA Green WE Antholine SJ Wong DR Richardson CR Chitambar 2001 Inhibition of malignant cell growth by 311, a novel iron chelator of the pyridoxal isonicotinoyl hydrazone class: effect on the R2 subunit of ribonucleotide reductase Clin Cancer Res 7 3574 3579 1:CAS:528:DC%2BD3MXptFaisLg%3D
    • (2001) Clin Cancer Res , vol.7 , pp. 3574-3579
    • Green, D.A.1    Antholine, W.E.2    Wong, S.J.3    Richardson, D.R.4    Chitambar, C.R.5
  • 8
    • 40549137513 scopus 로고    scopus 로고
    • A multicenter phase II trial of 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP, Triapine) and gemcitabine in advanced non-small-cell lung cancer with pharmacokinetic evaluation using peripheral blood mononuclear cells
    • 10.1007/s10637-007-9085-0 1:CAS:528:DC%2BD1cXivFKnsL0%3D
    • B Ma BC Goh EH Tan KC Lam R Soo SS Leong LZ Wang F Mo AT Chan B Zee T Mok 2008 A multicenter phase II trial of 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP, Triapine) and gemcitabine in advanced non-small-cell lung cancer with pharmacokinetic evaluation using peripheral blood mononuclear cells Invest New Drugs 26 169 173 10.1007/s10637-007-9085-0 1:CAS:528: DC%2BD1cXivFKnsL0%3D
    • (2008) Invest New Drugs , vol.26 , pp. 169-173
    • Ma, B.1    Goh, B.C.2    Tan, E.H.3    Lam, K.C.4    Soo, R.5    Leong, S.S.6    Wang, L.Z.7    Mo, F.8    Chan, A.T.9    Zee, B.10    Mok, T.11
  • 9
    • 67650394382 scopus 로고    scopus 로고
    • Phase II study of 3-AP Triapine in patients with recurrent or metastatic head and neck squamous cell carcinoma
    • 10.1093/annonc/mdn775 1:STN:280:DC%2BD1MvivFalsg%3D%3D
    • CM Nutting CM van Herpen AB Miah SA Bhide JP Machiels J Buter C Kelly D de Raucourt KJ Harrington 2009 Phase II study of 3-AP Triapine in patients with recurrent or metastatic head and neck squamous cell carcinoma Ann Oncol 20 1275 1279 10.1093/annonc/mdn775 1:STN:280:DC%2BD1MvivFalsg%3D%3D
    • (2009) Ann Oncol , vol.20 , pp. 1275-1279
    • Nutting, C.M.1    Van Herpen, C.M.2    Miah, A.B.3    Bhide, S.A.4    MacHiels, J.P.5    Buter, J.6    Kelly, C.7    De Raucourt, D.8    Harrington, K.J.9
  • 10
    • 34547562971 scopus 로고    scopus 로고
    • Design, synthesis, and characterization of novel iron chelators: Structure-activity relationships of the 2-benzoylpyridine thiosemicarbazone series and their 3-nitrobenzoyl analogues as potent antitumor agents
    • 10.1021/jm070445z 1:CAS:528:DC%2BD2sXns1Churw%3D
    • DS Kalinowski Y Yu PC Sharpe M Islam YT Liao DB Lovejoy N Kumar PV Bernhardt DR Richardson 2007 Design, synthesis, and characterization of novel iron chelators: structure-activity relationships of the 2-benzoylpyridine thiosemicarbazone series and their 3-nitrobenzoyl analogues as potent antitumor agents J Med Chem 50 3716 3729 10.1021/jm070445z 1:CAS:528:DC%2BD2sXns1Churw%3D
    • (2007) J Med Chem , vol.50 , pp. 3716-3729
    • Kalinowski, D.S.1    Yu, Y.2    Sharpe, P.C.3    Islam, M.4    Liao, Y.T.5    Lovejoy, D.B.6    Kumar, N.7    Bernhardt, P.V.8    Richardson, D.R.9
  • 11
    • 37849000472 scopus 로고    scopus 로고
    • Design, synthesis, and characterization of new iron chelators with anti-proliferative activity: Structure-activity relationships of novel thiohydrazone analogues
    • 10.1021/jm070839q 1:CAS:528:DC%2BD2sXht1arsLbP
    • DS Kalinowski PC Sharpe PV Bernhardt DR Richardson 2007 Design, synthesis, and characterization of new iron chelators with anti-proliferative activity: structure-activity relationships of novel thiohydrazone analogues J Med Chem 50 6212 6225 10.1021/jm070839q 1:CAS:528:DC%2BD2sXht1arsLbP
    • (2007) J Med Chem , vol.50 , pp. 6212-6225
    • Kalinowski, D.S.1    Sharpe, P.C.2    Bernhardt, P.V.3    Richardson, D.R.4
  • 12
    • 80053926659 scopus 로고    scopus 로고
    • Bp44mT: An orally-active iron chelator of the thiosemicarbazone class with potent anti-tumour efficacy
    • doi: 10.1111/j.1476-5381.2011.01526.x
    • Yu Y, Rahmanto YS, Richardson D (2011) Bp44mT: an orally-active iron chelator of the thiosemicarbazone class with potent anti-tumour efficacy. Br J Pharmacol. doi: 10.1111/j.1476-5381.2011.01526.x
    • (2011) Br J Pharmacol.
    • Yu, Y.1    Rahmanto, Y.S.2    Richardson, D.3
  • 13
    • 80053198672 scopus 로고    scopus 로고
    • Novel thiosemicarbazone iron chelators induce up-regulation and phosphorylation of the metastasis suppressor N-myc down-stream regulated gene 1: A new strategy for the treatment of pancreatic cancer
    • 10.1124/mol.111.073627 1:CAS:528:DC%2BC3MXhs1ansbvL
    • Z Kovacevic S Chikhani DB Lovejoy DR Richardson 2011 Novel thiosemicarbazone iron chelators induce up-regulation and phosphorylation of the metastasis suppressor N-myc down-stream regulated gene 1: a new strategy for the treatment of pancreatic cancer Mol Pharmacol 80 598 609 10.1124/mol.111. 073627 1:CAS:528:DC%2BC3MXhs1ansbvL
    • (2011) Mol Pharmacol , vol.80 , pp. 598-609
    • Kovacevic, Z.1    Chikhani, S.2    Lovejoy, D.B.3    Richardson, D.R.4
  • 14
    • 77951254905 scopus 로고    scopus 로고
    • Development of an LC-MS/MS method for analysis of interconvertible Z/E isomers of the novel anticancer agent, Bp4eT
    • 10.1007/s00216-009-3448-7 1:CAS:528:DC%2BC3cXhtl2ntL4%3D
    • J Stariat P Kovarikova J Klimes DS Kalinowski DR Richardson 2010 Development of an LC-MS/MS method for analysis of interconvertible Z/E isomers of the novel anticancer agent, Bp4eT Anal Bioanal Chem 397 161 171 10.1007/s00216-009-3448-7 1:CAS:528:DC%2BC3cXhtl2ntL4%3D
    • (2010) Anal Bioanal Chem , vol.397 , pp. 161-171
    • Stariat, J.1    Kovarikova, P.2    Klimes, J.3    Kalinowski, D.S.4    Richardson, D.R.5
  • 15
    • 34548388291 scopus 로고    scopus 로고
    • LC-MS-based metabolomics in drug metabolism
    • 10.1080/03602530701497804 1:CAS:528:DC%2BD2sXhtVSktL7L
    • C Chen FJ Gonzalez JR Idle 2007 LC-MS-based metabolomics in drug metabolism Drug Metab Rev 39 581 597 10.1080/03602530701497804 1:CAS:528:DC%2BD2sXhtVSktL7L
    • (2007) Drug Metab Rev , vol.39 , pp. 581-597
    • Chen, C.1    Gonzalez, F.J.2    Idle, J.R.3
  • 16
    • 36949024918 scopus 로고    scopus 로고
    • The conduct of drug metabolism studies considered good practice (II): In vitro experiments
    • 10.2174/138920007782798207 1:CAS:528:DC%2BD2sXhsVahtrrP
    • L Jia X Liu 2007 The conduct of drug metabolism studies considered good practice (II): in vitro experiments Curr Drug Metab 8 822 829 10.2174/138920007782798207 1:CAS:528:DC%2BD2sXhsVahtrrP
    • (2007) Curr Drug Metab , vol.8 , pp. 822-829
    • Jia, L.1    Liu, X.2
  • 17
    • 2442698003 scopus 로고    scopus 로고
    • Phase i and pharmacokinetic study of the ribonucleotide reductase inhibitor, 3-aminopyridine-2-carboxaldehyde thiosemicarbazone, administered by 96-hour intravenous continuous infusion
    • 10.1200/JCO.2004.07.158 1:CAS:528:DC%2BD2cXpsVWmur4%3D
    • S Wadler D Makower C Clairmont P Lambert K Fehn M Sznol 2004 Phase I and pharmacokinetic study of the ribonucleotide reductase inhibitor, 3-aminopyridine-2-carboxaldehyde thiosemicarbazone, administered by 96-hour intravenous continuous infusion J Clin Oncol 22 1553 1563 10.1200/JCO.2004.07. 158 1:CAS:528:DC%2BD2cXpsVWmur4%3D
    • (2004) J Clin Oncol , vol.22 , pp. 1553-1563
    • Wadler, S.1    Makower, D.2    Clairmont, C.3    Lambert, P.4    Fehn, K.5    Sznol, M.6
  • 18
    • 0141455148 scopus 로고    scopus 로고
    • Phase i and pharmacokinetic study of triapine, a potent ribonucleotide reductase inhibitor, administered daily for five days in patients with advanced solid tumors
    • 1:CAS:528:DC%2BD3sXns1OjtLs%3D
    • J Murren M Modiano C Clairmont P Lambert N Savaraj T Doyle M Sznol 2003 Phase I and pharmacokinetic study of triapine, a potent ribonucleotide reductase inhibitor, administered daily for five days in patients with advanced solid tumors Clin Cancer Res 9 4092 4100 1:CAS:528:DC%2BD3sXns1OjtLs%3D
    • (2003) Clin Cancer Res , vol.9 , pp. 4092-4100
    • Murren, J.1    Modiano, M.2    Clairmont, C.3    Lambert, P.4    Savaraj, N.5    Doyle, T.6    Sznol, M.7
  • 19
    • 42449153666 scopus 로고    scopus 로고
    • High-performance liquid chromatography-tandem mass spectrometry in the identification and determination of phase i and phase II drug metabolites
    • 10.1007/s00216-008-1962-7 1:CAS:528:DC%2BD1cXkvFClurw%3D
    • M Holcapek L Kolarova M Nobilis 2008 High-performance liquid chromatography-tandem mass spectrometry in the identification and determination of phase I and phase II drug metabolites Anal Bioanal Chem 391 59 78 10.1007/s00216-008-1962-7 1:CAS:528:DC%2BD1cXkvFClurw%3D
    • (2008) Anal Bioanal Chem , vol.391 , pp. 59-78
    • Holcapek, M.1    Kolarova, L.2    Nobilis, M.3
  • 20
    • 36949031034 scopus 로고    scopus 로고
    • The conduct of drug metabolism studies considered good practice (I): Analytical systems and in vivo studies
    • 10.2174/138920007782798153 1:CAS:528:DC%2BD2sXhsVahtrrO
    • X Liu L Jia 2007 The conduct of drug metabolism studies considered good practice (I): analytical systems and in vivo studies Curr Drug Metab 8 815 821 10.2174/138920007782798153 1:CAS:528:DC%2BD2sXhsVahtrrO
    • (2007) Curr Drug Metab , vol.8 , pp. 815-821
    • Liu, X.1    Jia, L.2
  • 21
    • 0037100453 scopus 로고    scopus 로고
    • Novel "hybrid" iron chelators derived from aroylhydrazones and thiosemicarbazones demonstrate selective antiproliferative activity against tumor cells
    • 10.1182/blood.V100.2.666 1:CAS:528:DC%2BD38XlsVWgtbs%3D
    • DB Lovejoy DR Richardson 2002 Novel "hybrid" iron chelators derived from aroylhydrazones and thiosemicarbazones demonstrate selective antiproliferative activity against tumor cells Blood 100 666 676 10.1182/blood.V100.2.666 1:CAS:528:DC%2BD38XlsVWgtbs%3D
    • (2002) Blood , vol.100 , pp. 666-676
    • Lovejoy, D.B.1    Richardson, D.R.2
  • 22
    • 34247224798 scopus 로고    scopus 로고
    • Achiral and chiral high-performance liquid chromatographic determination of flubendazole and its metabolites in biomatrices using UV photodiode-array and mass spectrometric detection
    • 10.1016/j.chroma.2007.01.013 1:CAS:528:DC%2BD2sXkslKkurg%3D
    • M Nobilis T Jira M Lisa M Holcapek B Szotakova J Lamka L Skalova 2007 Achiral and chiral high-performance liquid chromatographic determination of flubendazole and its metabolites in biomatrices using UV photodiode-array and mass spectrometric detection J Chromatogr A 1149 112 120 10.1016/j.chroma.2007. 01.013 1:CAS:528:DC%2BD2sXkslKkurg%3D
    • (2007) J Chromatogr A , vol.1149 , pp. 112-120
    • Nobilis, M.1    Jira, T.2    Lisa, M.3    Holcapek, M.4    Szotakova, B.5    Lamka, J.6    Skalova, L.7
  • 23
    • 82955233890 scopus 로고    scopus 로고
    • High-performance liquid chromatographic determination of tiapride and its phase i metabolite in blood plasma using tandem UV photodiode-array and fluorescence detection
    • 10.1016/j.jchromb.2011.10.032 1:CAS:528:DC%2BC3MXhsFOgtL3K
    • M Nobilis Z Vybíralová Z Szotáková Z Sládková M Kuneš Z Svoboda 2011 High-performance liquid chromatographic determination of tiapride and its phase I metabolite in blood plasma using tandem UV photodiode-array and fluorescence detection J Chromatogr B 879 3845 3852 10.1016/j.jchromb.2011.10.032 1:CAS:528:DC%2BC3MXhsFOgtL3K
    • (2011) J Chromatogr B , vol.879 , pp. 3845-3852
    • Nobilis, M.1    Vybíralová, Z.2    Szotáková, Z.3    Sládková, Z.4    Kuneš, M.5    Svoboda, Z.6
  • 25
    • 58149186443 scopus 로고    scopus 로고
    • HPLC methods for determination of two novel thiosemicarbazone anti-cancer drugs (N4mT and Dp44mT) in plasma and their application to in vitro plasma stability of these agents
    • 10.1016/j.jchromb.2008.11.044 1:CAS:528:DC%2BD1MXksVGisw%3D%3D
    • J Stariat P Kovarikova J Klimes DB Lovejoy DS Kalinowski DR Richardson 2009 HPLC methods for determination of two novel thiosemicarbazone anti-cancer drugs (N4mT and Dp44mT) in plasma and their application to in vitro plasma stability of these agents J Chromatogr B 877 316 322 10.1016/j.jchromb.2008.11. 044 1:CAS:528:DC%2BD1MXksVGisw%3D%3D
    • (2009) J Chromatogr B , vol.877 , pp. 316-322
    • Stariat, J.1    Kovarikova, P.2    Klimes, J.3    Lovejoy, D.B.4    Kalinowski, D.S.5    Richardson, D.R.6
  • 26
    • 3042858399 scopus 로고    scopus 로고
    • Distinguishing N-oxide and hydroxyl compounds: Impact of heated capillary/heated ion transfer tube in inducing atmospheric pressure ionization source decompositions
    • 10.1002/jms.623 1:CAS:528:DC%2BD2cXls1art78%3D
    • DM Peiris W Lam S Michael R Ramanathan 2004 Distinguishing N-oxide and hydroxyl compounds: impact of heated capillary/heated ion transfer tube in inducing atmospheric pressure ionization source decompositions J Mass Spectrom 39 600 606 10.1002/jms.623 1:CAS:528:DC%2BD2cXls1art78%3D
    • (2004) J Mass Spectrom , vol.39 , pp. 600-606
    • Peiris, D.M.1    Lam, W.2    Michael, S.3    Ramanathan, R.4
  • 27
    • 20444385508 scopus 로고    scopus 로고
    • Thermally induced N-to-O rearrangement of tert-N-oxides in atmospheric pressure chemical ionization and atmospheric pressure photoionization mass spectrometry: Differentiation of N-oxidation from hydroxylation and potential determination of N-oxidation site
    • 10.1021/ac048203j 1:CAS:528:DC%2BD2MXjsFaiu74%3D
    • S Ma SK Chowdhury KB Alton 2005 Thermally induced N-to-O rearrangement of tert-N-oxides in atmospheric pressure chemical ionization and atmospheric pressure photoionization mass spectrometry: differentiation of N-oxidation from hydroxylation and potential determination of N-oxidation site Anal Chem 77 3676 3682 10.1021/ac048203j 1:CAS:528:DC%2BD2MXjsFaiu74%3D
    • (2005) Anal Chem , vol.77 , pp. 3676-3682
    • Ma, S.1    Chowdhury, S.K.2    Alton, K.B.3
  • 28
    • 0032506639 scopus 로고    scopus 로고
    • Conversion of the thiocarbonyl group into the carbonyl group
    • 10.1016/S0040-4020(98)00880-1 1:CAS:528:DyaK1cXnvFWmur0%3D
    • A Corsaro V Pistara 1998 Conversion of the thiocarbonyl group into the carbonyl group Tetrahedron 54 15027 15062 10.1016/S0040-4020(98)00880-1 1:CAS:528:DyaK1cXnvFWmur0%3D
    • (1998) Tetrahedron , vol.54 , pp. 15027-15062
    • Corsaro, A.1    Pistara, V.2
  • 29
    • 3242718238 scopus 로고
    • Raney-nickel desulfuration of 1-substituted-thioureas and 1,3-disubstituted-thioureas
    • 1:CAS:528:DyaL28XlvFWmsbs%3D
    • MU Ali HM Meshram MG Paranjpe 1985 Raney-nickel desulfuration of 1-substituted-thioureas and 1,3-disubstituted-thioureas J Indian Chem Soc 62 666 669 1:CAS:528:DyaL28XlvFWmsbs%3D
    • (1985) J Indian Chem Soc , vol.62 , pp. 666-669
    • Ali, M.U.1    Meshram, H.M.2    Paranjpe, M.G.3
  • 30
    • 84981415323 scopus 로고
    • Oxidative products of thiocarboxylic acid amides. XXIV. Preparation of S, S-di- and S, S, S-trioxides of trisubstituted thioureas and a new preparative method for trisubstituted formamidines
    • 10.1002/cber.19691020820 1:CAS:528:DyaF1MXkvFSqtLg%3D
    • W Walter KP Ruess 1969 Oxidative products of thiocarboxylic acid amides. XXIV. Preparation of S, S-di- and S, S, S-trioxides of trisubstituted thioureas and a new preparative method for trisubstituted formamidines Chem Ber 102 2640 2650 10.1002/cber.19691020820 1:CAS:528:DyaF1MXkvFSqtLg%3D
    • (1969) Chem Ber , vol.102 , pp. 2640-2650
    • Walter, W.1    Ruess, K.P.2
  • 31
    • 0030745713 scopus 로고    scopus 로고
    • In vitro metabolism of N-(5-chloro-2-methylphenyl)-N'-(2-methylpropyl) thiourea: Species comparison and identification of a novel thiocarbamide- glutathione adduct
    • 10.1021/tx9700230 1:CAS:528:DyaK2sXktVSis74%3D
    • GJ Stevens K Hitchcock KY Wang GM Coppola RW Versace JA Chin M Shapiro S Suwanrumpha BLK Mangold 1997 In vitro metabolism of N-(5-chloro-2-methylphenyl)- N'-(2-methylpropyl)thiourea: species comparison and identification of a novel thiocarbamide-glutathione adduct Chem Res Toxicol 10 733 741 10.1021/tx9700230 1:CAS:528:DyaK2sXktVSis74%3D
    • (1997) Chem Res Toxicol , vol.10 , pp. 733-741
    • Stevens, G.J.1    Hitchcock, K.2    Wang, K.Y.3    Coppola, G.M.4    Versace, R.W.5    Chin, J.A.6    Shapiro, M.7    Suwanrumpha, S.8    Mangold, B.L.K.9
  • 32
    • 33750471953 scopus 로고    scopus 로고
    • Dipyridyl thiosemicarbazone chelators with potent and selective antitumor activity form iron complexes with redox activity
    • 10.1021/jm0606342 1:CAS:528:DC%2BD28XhtVWhsL%2FK
    • DR Richardson PC Sharpe DB Lovejoy D Senaratne DS Kalinowski M Islam PV Bernhardt 2006 Dipyridyl thiosemicarbazone chelators with potent and selective antitumor activity form iron complexes with redox activity J Med Chem 49 6510 6521 10.1021/jm0606342 1:CAS:528:DC%2BD28XhtVWhsL%2FK
    • (2006) J Med Chem , vol.49 , pp. 6510-6521
    • Richardson, D.R.1    Sharpe, P.C.2    Lovejoy, D.B.3    Senaratne, D.4    Kalinowski, D.S.5    Islam, M.6    Bernhardt, P.V.7
  • 33
    • 0242475774 scopus 로고
    • The preparation of some tetrasubstituted amidrazones
    • 10.1021/ja01162a523 1:CAS:528:DyaG3cXlt1ShtQ%3D%3D
    • H Rapoport RM Bonner 1950 The preparation of some tetrasubstituted amidrazones J Am Chem Soc 72 2783 2784 10.1021/ja01162a523 1:CAS:528: DyaG3cXlt1ShtQ%3D%3D
    • (1950) J Am Chem Soc , vol.72 , pp. 2783-2784
    • Rapoport, H.1    Bonner, R.M.2
  • 34
    • 0000174008 scopus 로고
    • Amidrazones.2. Tautomerism and alkylation studies
    • 10.1021/jo00947a020 1:CAS:528:DyaE3sXhtlGrsbs%3D
    • RF Smith DS Johnson RA Abgott MJ Madden 1973 Amidrazones.2. Tautomerism and alkylation studies J Org Chem 38 1344 1348 10.1021/jo00947a020 1:CAS:528:DyaE3sXhtlGrsbs%3D
    • (1973) J Org Chem , vol.38 , pp. 1344-1348
    • Smith, R.F.1    Johnson, D.S.2    Abgott, R.A.3    Madden, M.J.4
  • 35
    • 0030745713 scopus 로고    scopus 로고
    • In vitro metabolism of N-(5-chloro-2-methylphenyl)-N'-(2-methylpropyl) thiourea: Species comparison and identification of a novel thiocarbamide- glutathione adduct
    • 10.1021/tx9700230 1:CAS:528:DyaK2sXktVSis74%3D
    • GJ Stevens K Hitchcock YK Wang GM Coppola RW Versace JA Chin M Shapiro S Suwanrumpha BL Mangold 1997 In vitro metabolism of N-(5-chloro-2-methylphenyl)- N'-(2-methylpropyl)thiourea: species comparison and identification of a novel thiocarbamide-glutathione adduct Chem Res Toxicol 10 733 741 10.1021/tx9700230 1:CAS:528:DyaK2sXktVSis74%3D
    • (1997) Chem Res Toxicol , vol.10 , pp. 733-741
    • Stevens, G.J.1    Hitchcock, K.2    Wang, Y.K.3    Coppola, G.M.4    Versace, R.W.5    Chin, J.A.6    Shapiro, M.7    Suwanrumpha, S.8    Mangold, B.L.9
  • 36
    • 0033913769 scopus 로고    scopus 로고
    • Potentiation of thioacetamide liver injury in diabetic rats is due to induced CYP2E1
    • 1:CAS:528:DC%2BD3cXltlKgs7g%3D
    • T Wang K Shankar MJ Ronis HM Mehendale 2000 Potentiation of thioacetamide liver injury in diabetic rats is due to induced CYP2E1 J Pharmacol Exp Ther 294 473 479 1:CAS:528:DC%2BD3cXltlKgs7g%3D
    • (2000) J Pharmacol Exp Ther , vol.294 , pp. 473-479
    • Wang, T.1    Shankar, K.2    Ronis, M.J.3    Mehendale, H.M.4
  • 37
    • 34248584954 scopus 로고    scopus 로고
    • Covalent modification of microsomal lipids by thiobenzamide metabolites in vivo
    • 10.1021/tx600362h 1:CAS:528:DC%2BD2sXjtlCltb8%3D
    • T Ji K Ikehata YM Koen SW Esch TD Williams RP Hanzlik 2007 Covalent modification of microsomal lipids by thiobenzamide metabolites in vivo Chem Res Toxicol 20 701 708 10.1021/tx600362h 1:CAS:528:DC%2BD2sXjtlCltb8%3D
    • (2007) Chem Res Toxicol , vol.20 , pp. 701-708
    • Ji, T.1    Ikehata, K.2    Koen, Y.M.3    Esch, S.W.4    Williams, T.D.5    Hanzlik, R.P.6


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