메뉴 건너뛰기




Volumn 12, Issue 4, 2011, Pages 359-371

Electrochemistry in the mimicry of oxidative drug metabolism by cytochrome P450s

Author keywords

Cytochrome P450; Drug metabolism; Electrochemistry; Electrode modification; Mass spectrometry; Mimicry; Reactive oxygen species

Indexed keywords

CARBON; CYTOCHROME P450; CYTOCHROME P450 101; CYTOCHROME P450 2E1; CYTOCHROME P450 3A4; CYTOCHROME REDUCTASE; DRUG METABOLITE; FERRIC ION; FERROUS ION; HYDROGEN; HYDROGEN PEROXIDE; HYDROXYL RADICAL; METALLOPORPHYRIN; MYOGLOBIN; N ACETYL 1,4 BENZOQUINONE IMINE; REACTIVE OXYGEN METABOLITE; ROTIGOTINE; UNCLASSIFIED DRUG; VALPROIC ACID;

EID: 79953656393     PISSN: 13892002     EISSN: None     Source Type: Journal    
DOI: 10.2174/138920011795202929     Document Type: Article
Times cited : (53)

References (136)
  • 1
    • 1942439085 scopus 로고    scopus 로고
    • Biomimetic chemical catalysts in the oxidative activation of drugs
    • Bernadou, J.; Meunier, B. Biomimetic chemical catalysts in the oxidative activation of drugs. Adv. Synth. Catal. 2004, 346, 171-184. (Pubitemid 38515554)
    • (2004) Advanced Synthesis and Catalysis , vol.346 , Issue.2-3 , pp. 171-184
    • Bernadou, J.1    Meunier, B.2
  • 5
    • 0001045385 scopus 로고
    • A new Cytochrome in liver microsomes
    • Omura, T.; Sato, R. A new Cytochrome in liver microsomes. J. Biol. Chem. 1962, 237, 1375-1376.
    • (1962) J. Biol. Chem. , vol.237 , pp. 1375-1376
    • Omura, T.1    Sato, R.2
  • 6
    • 0023645035 scopus 로고
    • High-resolution crystal structure of cytochrome P450cam
    • Poulos, T. L.; Finzel, B. C.; Howard, A. J. High-resolution crystal structure of cytochrome P450cam. J. Mol. Biol. 1987, 195, 687-700.
    • (1987) J. Mol. Biol. , vol.195 , pp. 687-700
    • Poulos, T.L.1    Finzel, B.C.2    Howard, A.J.3
  • 7
    • 0027326717 scopus 로고
    • Crystal structure of hemoprotein domain of P450BM-3, a prototype for microsomal P450's
    • Ravichandran, K. G.; Boddupalli, S. S.; Hasermann, C. A.; Peterson, J. A.; Deisenhofer, J. Crystal structure of hemoprotein domain of P450BM-3, a prototype for microsomal P450's. Science 1993, 261, 731-736. (Pubitemid 23278388)
    • (1993) Science , vol.261 , Issue.5122 , pp. 731-736
    • Ravichandran, K.G.1    Boddupalli, S.S.2    Hasemann, C.A.3    Peterson, J.A.4    Deisenhofer, J.5
  • 8
    • 0035925164 scopus 로고    scopus 로고
    • Hydroxylation of camphor by reduced oxy-cytochrome p450cam: Mechanistic implications of EPR and ENDOR studies of catalytic intermediates in native and mutant enzymes
    • DOI 10.1021/ja003583l
    • Davydov, R.; Makris, T. M.; Kofman, V.; Werst, D. E.; Sligar, S. G.; Hoffman, B. M. Hydroxylation of camphor by reduced oxy- Cytochrome P450cam: Mechanistic implications of EPR and EN- DOR studies of catalytic intermediates in native and mutant enzymes. J. Am. Chem. Soc. 2001, 123, 1403-1415. (Pubitemid 32167333)
    • (2001) Journal of the American Chemical Society , vol.123 , Issue.7 , pp. 1403-1415
    • Davydov, R.1    Makris, T.M.2    Kofman, V.3    Werst, D.E.4    Sligar, S.G.5    Hoffman, B.M.6
  • 9
  • 10
    • 33748309228 scopus 로고    scopus 로고
    • Mass spectrometric characterization of high-valent metal-oxo, -peroxo and -peroxy intermediates of relevance in oxidation processes
    • DOI 10.1002/mas.20085
    • Bortolini, O.; Conte, V. Mass spectrometric characterization of high-valent metal-oxo, -peroxo and -peroxy intermediates of relevance in oxidation processes. Mass Spectrom. Rev. 2006, 25, 724-740. (Pubitemid 44330229)
    • (2006) Mass Spectrometry Reviews , vol.25 , Issue.5 , pp. 724-740
    • Bortolini, O.1    Conte, V.2
  • 11
    • 0000353336 scopus 로고
    • Radical clock substrate probes and kinetic isotope effect studies of the hy- droxylation of hydrocarbons by methane monooxygenase
    • Liu, K. E.; Johnson, C. C.; Newcomb, M.; Lippard, S. J. Radical clock substrate probes and kinetic isotope effect studies of the hy- droxylation of hydrocarbons by methane monooxygenase. J. Am. Chem. Soc. 1993, 115, 939-947.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 939-947
    • Liu, K.E.1    Johnson, C.C.2    Newcomb, M.3    Lippard, S.J.4
  • 12
    • 67650501146 scopus 로고    scopus 로고
    • A highly reactive P450 model Compound i
    • Bell, S. R.; Groves, J. T. A highly reactive P450 model Compound I. J. Am. Chem. Soc. 2009, 131, 9640-9641.
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 9640-9641
    • Bell, S.R.1    Groves, J.T.2
  • 13
    • 77349115125 scopus 로고    scopus 로고
    • P450 enzymes: Their structure, reactivity, and selectivity - Modeled by QM/MM calculations
    • Shaik, S.; Cohen, S.; Wang, Y.; Chen, H.; Kumar, D.; Thiel, W. P450 enzymes: Their structure, reactivity, and selectivity - Modeled by QM/MM calculations. Chem. Rev. 2010, 110, 949-1017.
    • (2010) Chem. Rev. , vol.110 , pp. 949-1017
    • Shaik, S.1    Cohen, S.2    Wang, Y.3    Chen, H.4    Kumar, D.5    Thiel, W.6
  • 14
    • 21944432511 scopus 로고    scopus 로고
    • Theoretical perspective on the structure and mechanism of cytochrome P450 enzymes
    • DOI 10.1021/cr030722j
    • Shaik, S.; Kumar, D.; de Visser, S. P.; Altun, A.; Thiel, W. Theoretical Perspective on the structure and mechanism of Cytochrome P450 enzymes. Chem. Rev. 2005, 105, 2279-2328. (Pubitemid 40947949)
    • (2005) Chemical Reviews , vol.105 , Issue.6 , pp. 2279-2328
    • Shaik, S.1    Kumar, D.2    De Visser, S.P.3    Altun, A.4    Thiel, W.5
  • 15
    • 4644275807 scopus 로고    scopus 로고
    • Mechanism of oxidation reactions catalyzed by Cytochrome P450 enzymes
    • Meunier, B.; de Visser, S. P.; Shaik, S. Mechanism of oxidation reactions catalyzed by Cytochrome P450 enzymes. Chem. Rev. 2004, 104, 3947-3980.
    • (2004) Chem. Rev. , vol.104 , pp. 3947-3980
    • Meunier, B.1    De Visser, S.P.2    Shaik, S.3
  • 16
    • 33645875048 scopus 로고    scopus 로고
    • High-valent iron in chemical and biological oxidations
    • Groves, J. T. High-valent iron in chemical and biological oxidations. J. Inorg. Biochem. 2006, 100, 434-447.
    • (2006) J. Inorg. Biochem. , vol.100 , pp. 434-447
    • Groves, J.T.1
  • 17
    • 0037228374 scopus 로고    scopus 로고
    • Multiple mechanisms and multiple oxidants in P450-catalyzed hydroxylations
    • DOI 10.1016/S0003-9861(02)00445-9, PII S0003986102004459
    • Newcomb, M.; Hollenberg, P. F.; Coon, M. J. Multiple mechanisms and multiple oxidants in P450-catalyzed hydroxylations. Arch. Biochem. Biophys. 2003, 409, 72-79. (Pubitemid 36042903)
    • (2003) Archives of Biochemistry and Biophysics , vol.409 , Issue.1 , pp. 72-79
    • Newcomb, M.1    Hollenberg, P.F.2    Coon, M.J.3
  • 18
    • 9744265664 scopus 로고    scopus 로고
    • Models and mechanisms of O-O bond activation by cytochrome P450: A critical assessment of the potential role of multiple active intermediates in oxidative catalysis
    • DOI 10.1111/j.1432-1033.2004.04380.x
    • Hlavica, P. Models and mechanisms of O-O bond activation by cytochrome P450: A critical assessment of the potential role of multiple active intermediates in oxidative catalysis. Eur. J. Bio-chem. 2004, 271, 4335-4360. (Pubitemid 39585211)
    • (2004) European Journal of Biochemistry , vol.271 , Issue.22 , pp. 4335-4360
    • Hlavica, P.1
  • 19
    • 0034973773 scopus 로고    scopus 로고
    • Common and uncommon cytochrome P450 reactions related to metabolism and chemical toxicity
    • Guengerich, F. P. Common and uncommon Cytochrome P450 reactions related to metabolism and chemical toxicity. Chem. Res. Toxicol. 2001, 14, 611-650. (Pubitemid 32565712)
    • (2001) Chemical Research in Toxicology , vol.14 , Issue.6 , pp. 611-650
    • Guengerich, F.P.1
  • 20
    • 0034973773 scopus 로고    scopus 로고
    • Cytochrome P450 and chemical toxicology
    • Guengerich, F. P. Cytochrome P450 and chemical toxicology. Chem. Res. Toxicol. 2001, 14, 611-650.
    • (2001) Chem. Res. Toxicol. , vol.14 , pp. 611-650
    • Guengerich, F.P.1
  • 22
    • 79953662624 scopus 로고    scopus 로고
    • Special issue on molecular and biomolecular electrochemistry
    • Special issue on Molecular and Biomolecular Electrochemistry. Chem. Rev. 2008, 108.
    • (2008) Chem. Rev. , pp. 108
  • 23
    • 0001096716 scopus 로고
    • Use of a porous electrode for in situ mass spectrometric determination of volatile electrode reaction products
    • Bruckenstein, S.; Gadde, R. R. Use of a porous electrode for in situ mass spectrometric determination of volatile electrode reaction products. J. Am. Chem. Soc. 1971, 93, 793-794.
    • (1971) J. Am. Chem. Soc. , vol.93 , pp. 793-794
    • Bruckenstein, S.1    Gadde, R.R.2
  • 24
    • 0022722302 scopus 로고
    • Electrochemical thermospray mass spectrometry instrumentation for coupling electrochemistry to mass spectrometry
    • Hambitzer, G.; Heitbaum, J. Electrochemical thermospray mass spectrometry instrumentation for coupling electrochemistry to mass spectrometry. Anal. Chem. 1986, 58, 1067-1070.
    • (1986) Anal. Chem. , vol.58 , pp. 1067-1070
    • Hambitzer, G.1    Heitbaum, J.2
  • 25
    • 0023987326 scopus 로고
    • Electrochem-istry/thermospray/tandem mass spectrometry in the study of biooxidation of purines
    • Volk, K. J.; Lee, M. S.; Yost, R. A.; Brajter-Toth, A. Electrochem-istry/thermospray/tandem mass spectrometry in the study of biooxidation of purines. Anal. Chem. 1988, 60, 720-722.
    • (1988) Anal. Chem. , vol.60 , pp. 720-722
    • Volk, K.J.1    Lee, M.S.2    Yost, R.A.3    Brajter-Toth, A.4
  • 26
    • 0000527148 scopus 로고
    • Electrochemistry combined online with electrospray mass spectrometry
    • Zhou, F.; Van Berkel, G. J. Electrochemistry combined online with electrospray mass spectrometry. Anal. Chem. 1995, 67, 3643-3649.
    • (1995) Anal. Chem. , vol.67 , pp. 3643-3649
    • Zhou, F.1    Van Berkel, G.J.2
  • 27
    • 0031185507 scopus 로고    scopus 로고
    • On-line linear sweep voltammetry electrospray mass spectrometry
    • Lu, W.; Xu, X.; Cole, R. B. On-line linear sweep voltammetry electrospray mass spectrometry. Anal. Chem. 1997, 69, 2478-2484.
    • (1997) Anal. Chem. , vol.69 , pp. 2478-2484
    • Lu, W.1    Xu, X.2    Cole, R.B.3
  • 28
    • 0000634947 scopus 로고    scopus 로고
    • A Thin-layer electrochemical flow cell coupled on-line with electrospray-mass spectrometry for the study of biological redox reactions
    • Deng, H.; Van Berkel, G. J. A Thin-layer electrochemical flow cell coupled on-line with electrospray-mass spectrometry for the study of biological redox reactions. Electroanalysis 1999, 11, 857-865.
    • (1999) Electroanalysis , vol.11 , pp. 857-865
    • Deng, H.1    Van Berkel, G.J.2
  • 29
    • 0036789698 scopus 로고    scopus 로고
    • Enhanced study and control of analyte oxidation in electrospray using a thin-channel, planar electrode emitter
    • Van Berkel, G. J.; Asano, K. G.; Kertesz, V. Enhanced study and control of analyte oxidation in electrospray using a thin-channel, planar electrode emitter. Anal. Chem. 2002, 74, 5047-5056.
    • (2002) Anal. Chem. , vol.74 , pp. 5047-5056
    • Van Berkel, G.J.1    Asano, K.G.2    Kertesz, V.3
  • 30
    • 34547779887 scopus 로고    scopus 로고
    • Using the electrochemistry of the elec-trospray ion source
    • Kertesz, Van Berkel, G. J. Using the electrochemistry of the elec-trospray ion source. Anal. Chem. 2007, 79, 5510-5520.
    • (2007) Anal. Chem. , vol.79 , pp. 5510-5520
    • Kertesz Van Berkel, G.J.1
  • 31
    • 0036361472 scopus 로고    scopus 로고
    • On-line electrochemistry -MS and related techniques
    • Diehl, G.; Karst, U. On-line electrochemistry -MS and related techniques. Anal. Bioanal. Chem. 2002, 373, 390-398.
    • (2002) Anal. Bioanal. Chem. , vol.373 , pp. 390-398
    • Diehl, G.1    Karst, U.2
  • 32
    • 42449137466 scopus 로고    scopus 로고
    • Biomimetic modeling of oxidative drug metabolism -Strategies, advantages and limitations
    • Lohmann, W.; Karst, U. Biomimetic modeling of oxidative drug metabolism -Strategies, advantages and limitations. Anal. Bioanal. Chem. 2008, 391, 79-96.
    • (2008) Anal. Bioanal. Chem. , vol.391 , pp. 79-96
    • Lohmann, W.1    Karst, U.2
  • 33
    • 77952510091 scopus 로고    scopus 로고
    • Online electrochemistry/mass spectrometry in drug metabolism studies: Principles and applications
    • Baumann, A.; Karst, U. Online electrochemistry/mass spectrometry in drug metabolism studies: principles and applications. Expert Opin. Drug Metab. Toxicol. 2010, 6, 715-731.
    • (2010) Expert Opin. Drug Metab. Toxicol. , vol.6 , pp. 715-731
    • Baumann, A.1    Karst, U.2
  • 34
    • 40049111087 scopus 로고    scopus 로고
    • Electrochemistry-mass spectrometry in drug metabolism and protein research
    • DOI 10.2174/138955708783331586
    • Permentier, H. P.; Bruins, A. P.; Bischoff, R. Electrochemistry-mass spectrometry in drug metabolism and protein research. Mini Rev. Med. Chem. 2008, 8, 46-56. (Pubitemid 351320929)
    • (2008) Mini-Reviews in Medicinal Chemistry , vol.8 , Issue.1 , pp. 46-56
    • Permentier, H.P.1    Bruins, A.P.2    Bischoff, R.3
  • 35
    • 0019775369 scopus 로고
    • Preparation of n-dealkylated drug metabolites by electrochemical simulation of biotransformation
    • Shono, T.; Toda, T.; Oshino, N. Preparation of N-dealkylated drug metabolites by electrochemical simulation of biotransformation. Drug Metab. Dispos. (Pubitemid 12201246)
    • (1981) Drug Metabolism and Disposition , vol.9 , Issue.5 , pp. 481-482
    • Shono, T.1    Toda, T.2    Oshino3
  • 36
    • 0034100506 scopus 로고    scopus 로고
    • In vitro mimicry of metabolic oxidation reactions by electrochemistry/ mass spectrometry
    • DOI 10.1002/(SICI)1097-0231(20000331)14:6<529::AID-RCM904>3.0.CO;2- H
    • Jurva, U.; Wikstrom, H. V.; Bruins, A. P. In vitro mimicry of metabolic oxidation reactions by electrochemistry/mass spectrome-try. Rapid Commun. Mass Spectrom. 2000, 14, 529-533. (Pubitemid 30153006)
    • (2000) Rapid Communications in Mass Spectrometry , vol.14 , Issue.6 , pp. 529-533
    • Jurva, U.1    Wikstrom, H.V.2    Bruins, A.P.3
  • 37
    • 0037258065 scopus 로고    scopus 로고
    • Comparison between electrochemistry/mass spectrometry and cytochrome P450 catalyzed oxidation reactions
    • DOI 10.1002/rcm.978
    • Jurva, U.; Wikstrom, H. V.; Weidolf, L.; Bruins, A. P. Comparison between electrochemistry/mass spectrometry and cytochrome P450 catalyzed oxidation reactions. Rapid Commun. Mass Spectrom. 2003, 17, 800-810. (Pubitemid 36433164)
    • (2003) Rapid Communications in Mass Spectrometry , vol.17 , Issue.8 , pp. 800-810
    • Jurva, U.1    Wikstrom, H.V.2    Weidolf, L.3    Bruins, A.P.4
  • 38
    • 61449236416 scopus 로고    scopus 로고
    • Novel metabolites of amodiaquine formed by CYP1A1 and CYP1B1: Structure elucidation using electrochemistry, mass spectrometry, and NMR
    • Johansson, T.; Jurva, U.; Gronberg, G.; Weidolf, L.; Ma-simirembwa, C. Novel metabolites of amodiaquine formed by CYP1A1 and CYP1B1: Structure elucidation using electrochemistry, mass spectrometry, and NMR. Drug Metab. Dispos. 2009, 37, 571-579.
    • (2009) Drug Metab. Dispos. , vol.37 , pp. 571-579
    • Johansson, T.1    Jurva, U.2    Gronberg, G.3    Weidolf, L.4    Ma-Simirembwa, C.5
  • 40
    • 78649732401 scopus 로고    scopus 로고
    • Electrochemistry-on-chip for on-line conversions in drug metabolism studies
    • Odijk, M.; Baumann, A.; Olthuis, W.; van den Berg, A.; Karst, U. Electrochemistry-on-chip for on-line conversions in drug metabolism studies. Biosens. Bioelectron., 2010, 26,1521-1527.
    • (2010) Biosens. Bioelectron. , vol.26 , pp. 1521-1527
    • Odijk, M.1    Baumann, A.2    Olthuis, W.3    Van Den Berg, A.4    Karst, U.5
  • 41
    • 3342900320 scopus 로고    scopus 로고
    • Electrochemistry/mass spectrometry (EC/MS) - A new tool to study drug metabolism and reaction mechanisms
    • DOI 10.1002/anie.200301763
    • Karst, U. Electrochemistry/Mass Spectrometry (EC/MS) -A new tool to study drug metabolism and reaction mechanisms. Angew. Chem. Int. Ed. Engl. 2004, 43, 2476-2478. (Pubitemid 39257706)
    • (2004) Angewandte Chemie - International Edition , vol.43 , Issue.19 , pp. 2476-2478
    • Karst, U.1
  • 42
    • 0017800253 scopus 로고
    • Aliphatic hydroxylation by highly purified liver microsomal cytochrome P-450. Evidence for a carbon radical intermediate
    • DOI 10.1016/0006-291X(78)91643-1
    • Groves, J. T.; McCluskey, G. A.; White, R. E.; Coon, M. J. Aliphatic hydroxylation by highly purified liver microsomal Cyto-chrome P-450. Evidence for a carbon radical intermediate. Bio-chem. Biophys. Res. Commun. 1978, 81, 154-160. (Pubitemid 8307814)
    • (1978) Biochemical and Biophysical Research Communications , vol.81 , Issue.1 , pp. 154-160
    • Groves, J.T.1    McClusky, G.A.2    White, R.E.3    Coon, M.J.4
  • 44
    • 33845376264 scopus 로고
    • Marcus theory in organic chemistry. Mechanisms of electron and proton transfers from aromatics and their cation radicals
    • Schlesener, C. J.; Amatore, C.; Kochi, J. K. Marcus theory in organic chemistry. Mechanisms of electron and proton transfers from aromatics and their cation radicals. J. Phys. Chem. 1986, 90, 3747-3756.
    • (1986) J. Phys. Chem. , vol.90 , pp. 3747-3756
    • Schlesener, C.J.1    Amatore, C.2    Kochi, J.K.3
  • 45
    • 34547165961 scopus 로고    scopus 로고
    • Mimicry of phase I drug metabolism - Novel methods for metabolite characterization and synthesis
    • DOI 10.1002/rcm.3077
    • Johansson, T.; Weidolf, L.; Jurva, U. Mimicry of phase I drug metabolism -Novel methods for metabolite characterization and synthesis. Rapid Commun. Mass Spectrom. 2007, 21 , 2323-2331. (Pubitemid 47121164)
    • (2007) Rapid Communications in Mass Spectrometry , vol.21 , Issue.14 , pp. 2323-2331
    • Johansson, T.1    Weidolf, L.2    Jurva, U.3
  • 46
    • 0001623910 scopus 로고
    • Anodic aromatic substitution
    • Eberson, L.; Nyberg K. Anodic aromatic substitution. Acc. Chem. Res. 1973, 3, 106-112.
    • (1973) Acc. Chem. Res. , vol.3 , pp. 106-112
    • Eberson, L.1    Nyberg, K.2
  • 47
    • 21244505432 scopus 로고    scopus 로고
    • Prediction of clozapine metabolism by on-line electrochemistry/liquid chromatography/mass spectrometry
    • DOI 10.1007/s00216-005-3053-3
    • van Leeuwen, S. M.; Blankert, B.; Kauffmann, J. M.; Karst, U. Prediction of clozapine metabolism by on-line electrochemistry/liquid chromatography/mass spectrometry. Anal. (Pubitemid 40891002)
    • (2005) Analytical and Bioanalytical Chemistry , vol.382 , Issue.3 , pp. 742-750
    • Van Leeuwen, S.M.1    Blankert, B.2    Kauffmann, J.-M.3    Karst, U.4
  • 48
    • 62249162146 scopus 로고    scopus 로고
    • Metabolic studies of tetrazepam based on electrochemical simulation in comparison to in vivo and in vitro methods
    • Baumann, A.; Lohmann, W.; Schubert, B.; Oberacher, H.; Karst, U. Metabolic studies of tetrazepam based on electrochemical simulation in comparison to in vivo and in vitro methods. J. Chroma-togr. A 2009, 1216, 3192-3198.
    • (2009) J. Chroma-togr. A , vol.1216 , pp. 3192-3198
    • Baumann, A.1    Lohmann, W.2    Schubert, B.3    Oberacher, H.4    Karst, U.5
  • 49
    • 33751182073 scopus 로고    scopus 로고
    • Simulation of the detoxification of paracetamol using on-line electrochemistry/liquid chromatogra-phy/mass spectrometry
    • Lohmann, W.; Karst, U. Simulation of the detoxification of paracetamol using on-line electrochemistry/liquid chromatogra-phy/mass spectrometry. Anal. Bioanal. Chem. 2006, 386, 1701-1708.
    • (2006) Anal. Bioanal. Chem. , vol.386 , pp. 1701-1708
    • Lohmann, W.1    Karst, U.2
  • 50
    • 34548577031 scopus 로고    scopus 로고
    • Generation and identification of reactive metabolites by electrochemistry and immobilized enzymes coupled on-line to liquid chromatography/mass spectrometry
    • DOI 10.1021/ac071100r
    • Lohmann, W.; Karst, U. Generation and identification of reactive metabolites by electrochemistry and immobilized enzymes coupled on-line to liquid chromatography/mass spectrometry. Anal. (Pubitemid 47395074)
    • (2007) Analytical Chemistry , vol.79 , Issue.17 , pp. 6831-6839
    • Lohmann, W.1    Karst, U.2
  • 51
    • 57749188066 scopus 로고    scopus 로고
    • On-line electrochemistry/liquid chromatography/mass spec-trometry for the simulation of pesticide metabolism
    • Lohmann, W.; Dötzer, R.; Gutter, G.; Van Leeuwen S. M.; Karst, U. On-line electrochemistry/liquid chromatography/mass spec-trometry for the simulation of pesticide metabolism. J. Am. Soc. Mass Spectrom. 2009, 20, 138-145.
    • (2009) J. Am. Soc. Mass Spectrom. , vol.20 , pp. 138-145
    • Lohmann, W.1    Dötzer, R.2    Gutter, G.3    Van Leeuwen, S.M.4    Karst, U.5
  • 52
    • 78649564714 scopus 로고    scopus 로고
    • Electrochemistry-mass spectrometry unveils the formation of reactive triclocarbon metabolites
    • Baumann, A.; Lohmann, W.; Rose, K.; Ahn, K. C.; Hammock, B. D.; Karst, U.; Schebb, N. H. Electrochemistry-mass spectrometry unveils the formation of reactive triclocarbon metabolites. Drug Metab. Dispos. 2010, 38, 2130-2138.
    • (2010) Drug Metab. Dispos. , vol.38 , pp. 2130-2138
    • Baumann, A.1    Lohmann, W.2    Rose, K.3    Ahn, K.C.4    Hammock, B.D.5    Karst, U.6    Schebb, N.H.7
  • 53
    • 4644349068 scopus 로고    scopus 로고
    • Liquid chromatography-electrochemistry-mass spectrometry of polycyclic aromatic hydrocarbons
    • DOI 10.1007/s00216-003-2150-4
    • van Leeuwen, S.; Hayen, H.; Karst, U. Liquid chromatography- electrochemistry-mass spectrometry of polycyclic aromatic hydrocarbons. Anal. (Pubitemid 40890203)
    • (2004) Analytical and Bioanalytical Chemistry , vol.378 , Issue.4 , pp. 917-925
    • Van Leeuwen, S.M.1    Hayen, H.2    Karst, U.3
  • 54
    • 0037960909 scopus 로고    scopus 로고
    • Can a single oxidant with two spin states masquerade as two different oxidants? A study of the sulfoxidation mechanism by cytochrome P450
    • DOI 10.1021/ja035135u
    • Sharma, P. K.; de Visser, S. P.; Shaik, S. Can a single oxidant with two spin states masquerade as two different oxidants? A study of the sulfoxidation mechanism by Cytochrome P450. J. Am. Chem. Soc. 2003, 125, 8698-8699. (Pubitemid 36886187)
    • (2003) Journal of the American Chemical Society , vol.125 , Issue.29 , pp. 8698-8699
    • Sharma, P.K.1    De Visser, S.P.2    Shaik, S.3
  • 55
    • 33845185530 scopus 로고
    • Electrochemical models for cytochrome P-450. N-Demethylation of tertiary amides by anodic oxidation
    • Hall, L. R.; Iwamoto, R. T.; Hanzlik, R. P. Electrochemical models for cytochrome P-450. N-Demethylation of tertiary amides by anodic oxidation. J. Org. Chem. 1989, 54, 2446-2451.
    • (1989) J. Org. Chem. , vol.54 , pp. 2446-2451
    • Hall, L.R.1    Iwamoto, R.T.2    Hanzlik, R.P.3
  • 56
    • 0000471634 scopus 로고
    • Electrochemical dealkylation of aliphatic amines
    • Smith, P. J.; Mann, C. K. Electrochemical dealkylation of aliphatic amines. J. Org. Chem. 1969, 34, 1821-1826.
    • (1969) J. Org. Chem. , vol.34 , pp. 1821-1826
    • Smith, P.J.1    Mann, C.K.2
  • 57
    • 24644510168 scopus 로고    scopus 로고
    • Model electrochemical-mass spectrometric studies of the cytochrome P450-catalyzed oxidations of cyclic tertiary allylamines
    • DOI 10.1021/ja052048o
    • Jurva, U.; Bissel, P.; Isin, E. M.; Igarashi, K.; Kuttab, S.; Castag-noli, Jr. N. Model electrochemical-mass spectrometric studies of the cytochrome P450-catalyzed oxidations of cyclic tertiary ally-lamines. J. Am. Chem. Soc. 2005, 727, 12368-12377. (Pubitemid 41279264)
    • (2005) Journal of the American Chemical Society , vol.127 , Issue.35 , pp. 12368-12377
    • Jurva, U.1    Bissel, P.2    Isin, E.M.3    Igarashi, K.4    Kuttab, S.5    Castagnoli Jr., N.6
  • 58
    • 77956603465 scopus 로고    scopus 로고
    • Lidocaine oxidation by electrogenerated reactive oxygen species in the light of oxidative drug metabolism
    • Nouri-Nigjeh, E.; Permentier, H. P.; Bischoff, R.; Bruins, A. P. Lidocaine oxidation by electrogenerated reactive oxygen species in the light of oxidative drug metabolism. Anal. Chem. 2010, 82, 7625-7633.
    • (2010) Anal. Chem. , vol.82 , pp. 7625-7633
    • Nouri-Nigjeh, E.1    Permentier, H.P.2    Bischoff, R.3    Bruins, A.P.4
  • 59
    • 33745790666 scopus 로고    scopus 로고
    • Investigation of the electrochemical oxidation products of zotepine and their fragmentation using on-line electrochemistry/electrospray ionization mass spectrometry
    • DOI 10.1002/jms.1017
    • Nozaki, K.; Kitagawa, H.; Kimura, S.; Kagayama, A.; Arakawa, R. Investigation of the electrochemical oxidation products of zotepine and their fragmentation using on-line electrochemistry/electrospray ionization mass spectrometry. J. Mass Spectrom. 2006, 41, 606-612. (Pubitemid 44023115)
    • (2006) Journal of Mass Spectrometry , vol.41 , Issue.5 , pp. 606-612
    • Nozaki, K.1    Kitagawa, H.2    Kimura, S.3    Kagayama, A.4    Arakawa, R.5
  • 60
    • 77951269369 scopus 로고    scopus 로고
    • P450-catalyzed vs. electrochemical oxidation of haloperidol studies by ultra-performance liquid chromatography/electrospray ionization mass spectrometry
    • Johansson, T.; Weidolf, L.; Castagnoli, Jr. N.; Jurva, U. P450-catalyzed vs. electrochemical oxidation of haloperidol studies by ultra-performance liquid chromatography/electrospray ionization mass spectrometry. Rapid Commun. Mass Spectrom. 2010, 24, 1231-1240.
    • (2010) Rapid Commun. Mass Spectrom. , vol.24 , pp. 1231-1240
    • Johansson, T.1    Weidolf, L.2    Castagnoli Jr., N.3    Jurva, U.4
  • 61
    • 0023697057 scopus 로고
    • Cyto-chrome P-450-catalyzed desaturation of valproic acid in vitro. Species differences, induction effects, and mechanistic studies
    • Rettie, A. E.; Boberg, M.; Rettenmeier, A. W.; Baillie, T. A. Cyto-chrome P-450-catalyzed desaturation of valproic acid in vitro. Species differences, induction effects, and mechanistic studies. J. Biol. Chem. 1988, 263, 13733-13738.
    • (1988) J. Biol. Chem. , vol.263 , pp. 13733-13738
    • Rettie, A.E.1    Boberg, M.2    Rettenmeier, A.W.3    Baillie, T.A.4
  • 62
    • 0027260697 scopus 로고
    • Generalized cytochrome P450-mediated oxidation and oxygenation reactions in aromatic substrates with activated N-H, O-H, C-H, or S-H substituents
    • Koymans, L.; Donne-Op Den Kelder, G. M.; Te Koppele, J. M.; Vermeulen, N. P. E. Generalized cytochrome P450-mediated oxidation and oxygenation reactions in aromatic substrates with activated N-H, O-H, C-H, or S-H substituents. Xenobiotica 1993, 23, 633-648. (Pubitemid 23227756)
    • (1993) Xenobiotica , vol.23 , Issue.6 , pp. 633-648
    • Koymans, L.1    Donne-Op Den Kelder, G.M.2    Te Koppele, J.M.3    Vermeulen, N.P.E.4
  • 63
    • 34250731278 scopus 로고    scopus 로고
    • Development and evaluation of an electrochemical method for studying reactive phase-I metabolites: Correlation to in vitro drug metabolism
    • DOI 10.1021/tx700029u
    • Madsen, K. G.; Olsen, J.; Skonberg, C.; Hansen, S. H.; Jurva, U. Development and evaluation of an electrochemical method for studying reactive phase-I metabolites: Correlation to in vivo drug metabolism. Chem. Res. Toxicol. 2007, 20, 821-831. (Pubitemid 46953690)
    • (2007) Chemical Research in Toxicology , vol.20 , Issue.5 , pp. 821-831
    • Madsen, K.G.1    Olsen, J.2    Skonberg, C.3    Hansen, S.H.4    Jurva, U.5
  • 64
    • 43149121807 scopus 로고    scopus 로고
    • Electrochemical generation of electrophilic drug metabolites: Characterization of amodiaquine quinoneimine and cysteinyl conjugates by MS, IR, and NMR
    • DOI 10.1021/tx700400c
    • Jurva, U.; Holmen, A.; Gronberg, G.; Masimirembwa, C.; Weidolf, L. Electrochemical generation of electrophilic drug metabolites: Characterization of amodiaquine quinoneimine and cysteinyl conjugates by MS, IR, and NMR. Chem. Res. Toxicol. 2008, 21, 928-935. (Pubitemid 351644571)
    • (2008) Chemical Research in Toxicology , vol.21 , Issue.4 , pp. 928-935
    • Jurva, U.1    Holmen, A.2    Gronberg, G.3    Masimirembwa, C.4    Weidolf, L.5
  • 65
    • 57149096673 scopus 로고    scopus 로고
    • Electrochemical oxidation of metolazone at a glassy carbon electrode
    • Pontinha, A. D. R.; Oliveira, S. C. B.; Oliveira-Brett A. M. Electrochemical oxidation of metolazone at a glassy carbon electrode. Electroanalysis 2008, 23, 2531-2536.
    • (2008) Electroanalysis , vol.23 , pp. 2531-2536
    • Pontinha, A.D.R.1    Oliveira, S.C.B.2    Oliveira-Brett, A.M.3
  • 67
    • 55849112645 scopus 로고    scopus 로고
    • Electrochemical behavior of thalidomide at a glassy carbon electrode
    • Oliveira, S. C. B.; Vivan, M.; Oliveira-Brett A. M. Electrochemical behavior of thalidomide at a glassy carbon electrode. Electroanalysis 2008, 22, 2429-2434.
    • (2008) Electroanalysis , vol.22 , pp. 2429-2434
    • Oliveira, S.C.B.1    Vivan, M.2    Oliveira-Brett, A.M.3
  • 68
    • 0014940991 scopus 로고
    • Electrochemical oxidation pathways of benzo[a]pyrene
    • Jeftic, L.; Adams, R. N. Electrochemical oxidation pathways of benzo[a]pyrene. J. Am. Chem. Soc. 1970, 92, 1332-1337.
    • (1970) J. Am. Chem. Soc. , vol.92 , pp. 1332-1337
    • Jeftic, L.1    Adams, R.N.2
  • 69
    • 1842421766 scopus 로고    scopus 로고
    • On-Line Probe for Fast Electrochemis-try/electrospray mass spectrometry investigation of polycyclic aromatic hydrocarbons
    • Xu, X.; Lu, W.; Cole, R. B. On-Line Probe for Fast Electrochemis-try/ electrospray mass spectrometry investigation of polycyclic aromatic hydrocarbons. Anal. Chem. 1996, 68, 4244-4253.
    • (1996) Anal. Chem. , vol.68 , pp. 4244-4253
    • Xu, X.1    Lu, W.2    Cole, R.B.3
  • 70
    • 0001748518 scopus 로고
    • One-electron mechanism for the electrochemical reduction of molecular oxygen
    • Sawyer, D. T.; Seo, E. T. One-electron mechanism for the electrochemical reduction of molecular oxygen. Inorg. Chem. 1977, 16, 499-501.
    • (1977) Inorg. Chem. , vol.16 , pp. 499-501
    • Sawyer, D.T.1    Seo, E.T.2
  • 72
    • 31144457542 scopus 로고    scopus 로고
    • Study of the electrochemical reduction of dioxygen in acetonitrile in the presence of weak acids
    • DOI 10.1021/jp055296f
    • Singh, P. S.; Evans, D. H. Study of the electrochemical reduction of dioxygen in acetonitrile in the presence of weak acids. J. Phys. Chem. B 2006, 110, 637-644. (Pubitemid 43133587)
    • (2006) Journal of Physical Chemistry B , vol.110 , Issue.1 , pp. 637-644
    • Singh, P.S.1    Evans, D.H.2
  • 74
    • 0022710033 scopus 로고
    • 2 multiplied by (times) ) IN APROTIC SOLVENTS THAT CONTAIN BRONSTED ACIDS.
    • Cofre, P.; Sawyer, D. T. Electrochemical reduction of dioxygen to perhydroxyl (HO2) in aprotic solvents that contain Bransted acids. Anal. (Pubitemid 16571208)
    • (1986) Analytical Chemistry , vol.58 , Issue.6 , pp. 1057-1062
    • Cofre Pablo1    Sawyer Donald, T.2
  • 75
    • 0020764209 scopus 로고
    • MOLECULAR OXYGEN ELECTROREDUCTION AT Pt and Au ELECTRODES IN ACETONITRILE SOLUTIONS.
    • Lorenzola, T. A.; Lopez, B. A.; Giordano, M. C. Molecular oxygen electroreduction at Pt and Au electrodes in acetonitrile solutions. J. Electrochem. Soc. 1983, 130, 1359-1365. (Pubitemid 13560303)
    • (1983) Journal of the Electrochemical Society , vol.130 , Issue.6 , pp. 1359-1365
    • Lorenzola, T.A.1    Lopez, B.A.2    Giordano, M.C.3
  • 76
    • 0020180559 scopus 로고
    • Effects of media and electrode materials on the electrochemical reduction of dioxygen
    • Sawyer, D. T.; Chiericato, G.; Angelis, C. T.; Nanni, E. J.; Tsu-chiya, T. Effects of media and electrode materials on the electrochemical reduction of dioxygen. Anal. Chem. 1982, 54, 1720-1724.
    • (1982) Anal. Chem. , vol.54 , pp. 1720-1724
    • Sawyer, D.T.1    Chiericato, G.2    Angelis, C.T.3    Nanni, E.J.4    Tsu-Chiya, T.5
  • 77
    • 0342743076 scopus 로고
    • Oxygen induced electroreduction of hydrogen peroxide and reduction of oxygen at the rotated gold wire electrode
    • Kolthoff, I. M.; Jordan, J. Oxygen induced electroreduction of hydrogen peroxide and reduction of oxygen at the rotated gold wire electrode. J. Am. Chem. Soc. 1952, 74, 4801-4805.
    • (1952) J. Am. Chem. Soc. , vol.74 , pp. 4801-4805
    • Kolthoff, I.M.1    Jordan, J.2
  • 78
    • 85010152316 scopus 로고
    • Reactions of superoxide with water and with hydrogen peroxide
    • Ozawa, T.; Hanaki, A. Reactions of superoxide with water and with hydrogen peroxide. Chem. Pharm. Bull. 1981, 29, 926-928.
    • (1981) Chem. Pharm. Bull. , vol.29 , pp. 926-928
    • Ozawa, T.1    Hanaki, A.2
  • 79
    • 0000787806 scopus 로고
    • Organic nitrogen compounds. I. Peroxide intermediates of tertiary alkylamine oxidation by hydrogen peroxide
    • Oswald, A. A.; Guertin, D. L. Organic nitrogen compounds. I. Peroxide intermediates of tertiary alkylamine oxidation by hydrogen peroxide. J. Org. Chem. 1963, 28, 651-657.
    • (1963) J. Org. Chem. , vol.28 , pp. 651-657
    • Oswald, A.A.1    Guertin, D.L.2
  • 80
    • 75849118346 scopus 로고    scopus 로고
    • And mediated anodic oxidation of organic pollutants
    • Panizza, M.; Cerisola, G. Direct and mediated anodic oxidation of organic pollutants. Chem. Rev. 2009, 109, 6541-6569.
    • (2009) Chem. Rev. , vol.109 , pp. 6541-6569
    • Panizza, M.1    Direct, C.G.2
  • 82
    • 77950859797 scopus 로고    scopus 로고
    • Voltammetric and electrochemical impedance spectroscopy characterization of a cathodic and anodic pre-treated boron doped diamond electrode
    • Oliveira, S. C. B.; Oliveira-Brett A. M. Voltammetric and electrochemical impedance spectroscopy characterization of a cathodic and anodic pre-treated boron doped diamond electrode. Electro-chim. Acta 2010, 55, 4599-4605.
    • (2010) Electro-chim. Acta , vol.55 , pp. 4599-4605
    • Oliveira, S.C.B.1    Oliveira-Brett, A.M.2
  • 83
    • 25144443639 scopus 로고    scopus 로고
    • Electrochemical oxidation of hydroquinone, resorcinol, and catechol on boron-doped diamond anodes
    • DOI 10.1021/es0500660
    • Nasr, B.; Abdellatif, G.; Canizares, P.; Sáez, C.; Lobato, J.; Rodrigo, M. A. Electrochemical oxidation of hydroquinone, resorcinol, and catechol on boron-doped diamond anodes. Environ. Sci. Tech-nol. 2005, 39, 7234-7239. (Pubitemid 41339090)
    • (2005) Environmental Science and Technology , vol.39 , Issue.18 , pp. 7234-7239
    • Nasr, B.1    Abdellatif, G.2    Canizares, P.3    Saez, C.4    Lobato, J.5    Rodrigo, M.A.6
  • 84
    • 75849120863 scopus 로고    scopus 로고
    • Electro-Fenton process and related electrochemical technologies based on Fenton reaction chemistry
    • Brillas, E.; Sires, I.; Oturan, M. A. Electro-Fenton process and related electrochemical technologies based on Fenton reaction chemistry. Chem. Rev. 2009, 109, 6570-6631.
    • (2009) Chem. Rev. , vol.109 , pp. 6570-6631
    • Brillas, E.1    Sires, I.2    Oturan, M.A.3
  • 85
    • 11144308275 scopus 로고    scopus 로고
    • Mineralization of paracetamol in aqueous medium by anodic oxidation with a boron-doped diamond electrode
    • DOI 10.1016/j.chemosphere.2004.09.028, PII S0045653504008082
    • Brillas, E.; Sires, I.; Arias, C.; Cabot, P. L.; Centellas, F.; Rodriguez, R. M.; Garrido, J. A. Mineralization of paracetamol in aqueous medium by anodic oxidation with a boron-doped diamond electrode. Chemosphere 2005, 58, 399-406. (Pubitemid 40023207)
    • (2005) Chemosphere , vol.58 , Issue.4 , pp. 399-406
    • Brillas, E.1    Sires, I.2    Arias, C.3    Cabot, P.L.4    Centellas, F.5    Rodriguez, R.M.6    Garrido, J.A.7
  • 86
    • 0000009222 scopus 로고
    • Hydroxylation by electrochemically generated OH-radicals. Mono-and polyhydroxylation of benzoic acid: Products and isomers' distribution
    • Oturan, M. A.; Pinson, J. Hydroxylation by electrochemically generated OH-radicals. Mono-and polyhydroxylation of benzoic acid: Products and isomers' distribution. J. Phys. Chem. 1995, 99, 13948-13954.
    • (1995) J. Phys. Chem. , vol.99 , pp. 13948-13954
    • Oturan, M.A.1    Pinson, J.2
  • 87
    • 1542789741 scopus 로고
    • Fenton's reagent revisited
    • Walling, C. Fenton's reagent revisited. Acc. Chem. Res. 1975, 8, 125-131.
    • (1975) Acc. Chem. Res. , vol.8 , pp. 125-131
    • Walling, C.1
  • 88
    • 3042756152 scopus 로고    scopus 로고
    • Radical generation by the interaction of transition metals with common oxidants
    • DOI 10.1021/es035121o
    • Anipsitakis, G. P.; Dionysiou, D. D. Radical generation by the interaction of transition metals with common oxidants. Environ. Sci. Technol. 2004, 38, 3705-3712. (Pubitemid 38879912)
    • (2004) Environmental Science and Technology , vol.38 , Issue.13 , pp. 3705-3712
    • Anipsitakis, G.P.1    Dionysiou, D.D.2
  • 89
    • 2542609348 scopus 로고    scopus 로고
    • x; M = Fe, Cu, Co, Mn]/Hydroperoxide-Induced Activation of Dioxygen for the Oxygenation of Hydrocarbons: Oxygenated Fenton Chemistry
    • Sawyer, D. T.; Sobkowiak, A.; Matsushita, T. Metal [ML,; M = Fe, Cu, Co, Mn]/hydroperoxide-induced activation of dioxygen for the oxygenation of hydrocarbons: Oxygenated Fenton chemistry. Acc. Chem. Res. 1996, 29, 409-416. (Pubitemid 126453229)
    • (1996) Accounts of Chemical Research , vol.29 , Issue.9 , pp. 409-416
    • Sawyer, D.T.1    Sobkowiak, A.2    Matsushita, T.3
  • 90
    • 0028789234 scopus 로고
    • +)], not free hydroxyl radical (HO-)}
    • Hage, J. P.; Llobet, A.; Sawyer, D. T. Aromatic hydroxylation by Fenton reagents {Reactive intermediate[Lx+FemOOH(BH+)], not free hydroxyl radical (HO-)}. Bioorg. Med. Chem. 1995, 3, 1383-1388.
    • (1995) Bioorg. Med. Chem. , vol.3 , pp. 1383-1388
    • Hage, J.P.1    Llobet, A.2    Sawyer, D.T.3
  • 91
    • 0000213339 scopus 로고    scopus 로고
    • Intermediates in the reactions of Fenton type reagents
    • Walling, C. Intermediates in the reactions of Fenton type reagents. Acc. Chem. Res. 1998, 31, 155-157.
    • (1998) Acc. Chem. Res. , vol.31 , pp. 155-157
    • Walling, C.1
  • 92
    • 0036388293 scopus 로고    scopus 로고
    • Electrochemically assisted Fenton reaction: Reaction of hydroxyl radicals with xenobiot-ics followed by on-line analysis with high-performance liquid chromatography/tandem mass spectrometry
    • Jurva, U.; Wikstrom, H. V.; Bruins, A. P. Electrochemically assisted Fenton reaction: reaction of hydroxyl radicals with xenobiot-ics followed by on-line analysis with high-performance liquid chromatography/tandem mass spectrometry. Rapid Commun. Mass Spectrom. 2002, 16, 1934-1940.
    • (2002) Rapid Commun. Mass Spectrom. , vol.16 , pp. 1934-1940
    • Jurva, U.1    Wikstrom, H.V.2    Bruins, A.P.3
  • 93
    • 34147215935 scopus 로고    scopus 로고
    • Electro-Fenton degradation of antimicrobials triclosan and triclocarban
    • DOI 10.1016/j.electacta.2007.03.011, PII S0013468607003714
    • Sires, I.; Oturan, N.; Oturan, M. A.; Rodriguez, R. M.; Garrido, J. A.; Brillas, E. Electro-Fenton degradation of antimicrobials tri-closan and triclocarban. Electrochim. Acta 2007, 52, 5493-5503. (Pubitemid 46578132)
    • (2007) Electrochimica Acta , vol.52 , Issue.17 , pp. 5493-5503
    • Sires, I.1    Oturan, N.2    Oturan, M.A.3    Rodriguez, R.M.4    Garrido, J.A.5    Brillas, E.6
  • 95
    • 33845186298 scopus 로고    scopus 로고
    • Degradation of clofibric acid in acidic aqueous medium by electro-Fenton and photoelectro-Fenton
    • DOI 10.1016/j.chemosphere.2006.07.039, PII S004565350600974X
    • Sirés, I.; Arias, C.; Cabot, P. L.; Centellas, F.; Garrido, J. A.; Rodriguez, R. M.; Brillas, E. Degradation of clofibric acid in acidic aqueous medium by electro-Fenton and photoelectro-Fenton. Chemosphere 2007, 66, 1660-1669. (Pubitemid 44855078)
    • (2007) Chemosphere , vol.66 , Issue.9 , pp. 1660-1669
    • Sires, I.1    Arias, C.2    Cabot, P.L.3    Centellas, F.4    Garrido, J.A.5    Rodriguez, R.M.6    Brillas, E.7
  • 96
    • 0141580907 scopus 로고
    • The selective functionalization of saturated hydrocarbons: Gif chemistry
    • Barton, D. H. R.; Doller, D. The selective functionalization of saturated hydrocarbons: Gif chemistry. Acc. Chem. Res. 1992, 25, 504-512.
    • (1992) Acc. Chem. Res. , vol.25 , pp. 504-512
    • Barton, D.H.R.1    Doller, D.2
  • 97
    • 0025219746 scopus 로고
    • The effect of ligand variation on the rate of cyclododecane oxidation under modified GoAgg(II) conditions
    • DOI 10.1016/S0040-4039(00)88846-2
    • About-Jaudet, E.; Barton, D. H. R.; Csuhai, E.; Ozbalik, N. The effect of ligand variation on the rate of cyclododecane oxidation under modified Go AggII conditions. Tetrahedron Lett. (Pubitemid 20096606)
    • (1990) Tetrahedron Letters , vol.31 , Issue.12 , pp. 1657-1660
    • About-Jaudet, E.1    Barton, D.H.R.2    Csuhai, E.3    Ozbalik, N.4
  • 98
    • 0025279928 scopus 로고
    • Comparison of Gif-type reactivity towards alkanes with standard radical reaction selectivity. Gif oxidation of n-butane and propane
    • DOI 10.1016/S0040-4039(00)94704-X
    • Barton, D. H. R.; Csuhai, E.; Doller, D.; Ozbalik, N.; Senglet, N. Comparison of Gif-type reactivity towards alkanes with standard radical reaction selectivity. Gif oxidation of n-butane and propane. Tetrahedron Lett. (Pubitemid 20188087)
    • (1990) Tetrahedron Letters , vol.31 , Issue.22 , pp. 3097-3100
    • Barton, D.H.R.1    Csuhai, E.2    Doller, D.3    Ozbalik, N.4    Senglet, N.5
  • 99
    • 0030043907 scopus 로고    scopus 로고
    • Hypersensitive radical probe studies of Gif oxidations
    • DOI 10.1016/0040-4039(95)02330-5
    • Newcomb, M.; Simakov, P. A.; Park, S.-U. Hypersensitive radical probe studies of Gif oxidations. Tetrahedron Lett. (Pubitemid 26047070)
    • (1996) Tetrahedron Letters , vol.37 , Issue.6 , pp. 819-822
    • Newcomb, M.1    Simakov, P.A.2    Park, S.-U.3
  • 101
    • 0035849439 scopus 로고    scopus 로고
    • Radical and non-radical chemistry of the Fenton-like systems in the presence of organic substrates
    • Gozzo, F. Radical and non-radical chemistry of the Fenton-like systems in the presence of organic substrates. J. Mol. Catal. A Chem. 2001, 7 77, 1-22.
    • (2001) J. Mol. Catal. A Chem. , vol.77 , Issue.7 , pp. 1-22
    • Gozzo, F.1
  • 102
    • 0001440008 scopus 로고
    • Selective oxidation of saturated hydrocarbons using an electrochemical modification of the Gif system
    • Balavoine, G.; Barton, D. H. R.; Boivin, J.; Gref, A.; Ozbalik, N.; Rivière, H. Selective oxidation of saturated hydrocarbons using an electrochemical modification of the Gif system. Tetrahedron Lett. 1986, 27, 2849-2852.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 2849-2852
    • Balavoine, G.1    Barton, D.H.R.2    Boivin, J.3    Gref, A.4    Ozbalik, N.5    Rivière, H.6
  • 104
    • 0000254084 scopus 로고    scopus 로고
    • Remarkable Effects of Metal, Solvent, and Oxidant on Metalloporphyrin- Catalyzed Enantioselective Epoxidation of Olefins
    • Gross, Z.; Ini, S. Remarkable effects of metal, solvent, and oxidant on metalloporphyrin-catalyzed enantioselective epoxidation of ole-fins. J. Org. Chem. 1997, 62, 5514-5521. (Pubitemid 127494900)
    • (1997) Journal of Organic Chemistry , vol.62 , Issue.16 , pp. 5514-5521
    • Gross, Z.1    Ini, S.2
  • 105
    • 0024559946 scopus 로고
    • Regioselective oxidation catalysis in synthetic phospholipid vesicles. Membrane-spanning steroidal metalloporphyrins
    • DOI 10.1021/ja00190a026
    • Groves, J. T.; Neumann, R. Regioselective oxidation catalysis in synthetic phospholipid vesicles. Membrane-spanning steroidal met-alloporphyrins. J. Am. Chem. Soc. 1989, 777, 2900-2909. (Pubitemid 19106178)
    • (1989) Journal of the American Chemical Society , vol.111 , Issue.8 , pp. 2900-2909
    • Groves, J.T.1    Neumann, R.2
  • 106
    • 2942633224 scopus 로고    scopus 로고
    • Metalloporphyrin mediated biomimetic oxidations. A useful tool for the investigation of cytochrome P450 catalyzed oxidative metabolism
    • Balogh, G. T.; Keseru, G. M. Metalloporphyrin mediated biomimetic oxidations. A useful tool for the investigation of cyto-chrome P450 catalyzed oxidative metabolism. Arkivoc 2004, 7, 124-139. (Pubitemid 38773719)
    • (2004) Arkivoc , vol.2004 , Issue.7 , pp. 124-139
    • Balogh, G.T.1    Keseru, G.M.2
  • 107
    • 34547728317 scopus 로고    scopus 로고
    • High-valent iron(IV) oxo complexes of heme and non-heme ligands in oxygenation reactions
    • Nam, W. High-valent iron(IV) oxo complexes of heme and non-heme ligands in oxygenation reactions. Acc. Chem. Res. 2007, 40, 522-531.
    • (2007) Acc. Chem. Res. , vol.40 , pp. 522-531
    • Nam, W.1
  • 108
    • 0000867828 scopus 로고
    • An efficient electro-catalytic model cytochrome P-450 epoxidation cycle
    • Creager, S. E.; Raybuck, S. A.; Murray, R. W. An efficient electro-catalytic model cytochrome P-450 epoxidation cycle. J. Am. Chem. Soc. 1986, 708, 4225-4227.
    • (1986) J. Am. Chem. Soc. , vol.708 , pp. 4225-4227
    • Creager, S.E.1    Raybuck, S.A.2    Murray, R.W.3
  • 109
    • 0000752876 scopus 로고
    • Electrochemical reactivity of man-ganese(II) porphyrins. Effects of dioxygen, benzoic anhydride, and axial ligands
    • Creager, S. E.; Murray, R. W. Electrochemical reactivity of man-ganese(II) porphyrins. Effects of dioxygen, benzoic anhydride, and axial ligands. Inorg. Chem. 1987, 26, 2612-2618.
    • (1987) Inorg. Chem. , vol.26 , pp. 2612-2618
    • Creager, S.E.1    Murray, R.W.2
  • 111
    • 0011697055 scopus 로고
    • Metalloporphyrins as versatile catalysts for oxidation reactions and oxidative DNA cleavage
    • Meunier, B. Metalloporphyrins as versatile catalysts for oxidation reactions and oxidative DNA cleavage. Chem. Rev. 1992, 92, 1411-1456.
    • (1992) Chem. Rev. , vol.92 , pp. 1411-1456
    • Meunier, B.1
  • 112
    • 32544434991 scopus 로고    scopus 로고
    • Supported metalloporphyrin catalysts for alkene epoxidation
    • DOI 10.1039/b509985d
    • Brule, E.; de Miguel, Y. R. Supported metalloporphyrin catalysts for alkene epoxidation. Org. Biomol. Chem. 2006, 4, 599-609. (Pubitemid 43237715)
    • (2006) Organic and Biomolecular Chemistry , vol.4 , Issue.4 , pp. 599-609
    • Brule, E.1    De Miguel, Y.R.2
  • 113
    • 22144462526 scopus 로고    scopus 로고
    • Immobilization of metalloporphyrin complexes in molecular sieves and their catalytic activity
    • Radha Rani, V.; Radha Kishan, M.; Kulkarni, S. J.; Raghavan, K. V. Immobilization of metalloporphyrin complexes in molecular sieves and their catalytic activity. Catal. Commun. 2005, 6, 531-538.
    • (2005) Catal. Commun. , vol.6 , pp. 531-538
    • Radha Rani, V.1    Radha Kishan, M.2    Kulkarni, S.J.3    Raghavan, K.V.4
  • 114
    • 0028169247 scopus 로고
    • An efficient mimic of cytochrome P-450 from a zeolite-encaged iron complex in a polymer membrane
    • DOI 10.1038/370541a0
    • Parton, R. F.; Vankelecom, I. F. J.; Casselman, M. J. A.; Bezouk-hanova, C. P.; Uytterhoeven, J. B.; Jacobs, P. A. An efficient mimic of cytochrome P-450 from a zeolite-encaged iron complex in a polymer membrane. Nature 1994, 370, 541-544. (Pubitemid 24265859)
    • (1994) Nature , vol.370 , Issue.6490 , pp. 541-544
    • Parton, R.F.1    Vankelecom, I.F.J.2    Casselman, M.J.A.3    Bezoukhanova, C.P.4    Uytterhoeven, J.B.5    Jacobs, P.A.6
  • 115
    • 0030601967 scopus 로고    scopus 로고
    • Electropolymerized manganese porphyrin films as catalytic electrode materials for biomimetic oxidations with molecular oxygen
    • DOI 10.1016/S1381-1169(96)00028-3, PII S1381116996000283
    • Bedioui, F.; Devynck, J.; Bied-Charreton, C. Electropolymerized manganese porphyrin films as catalytic electrode materials for biomimetic oxidations with molecular oxygen. J. Mol. Catal. A Chem. 1996, 773, 3-11. (Pubitemid 27012644)
    • (1996) Journal of Molecular Catalysis A: Chemical , vol.113 , Issue.1-2 , pp. 3-11
    • Bedioui, F.1    Devynck, J.2    Bied-Charreton, C.3
  • 116
    • 0002001083 scopus 로고
    • Immobilization of metalloporphyrins in electropolymerized films: Design and applications
    • Bedioui, F.; Devynck, J.; Bied-Charreton, C. Immobilization of metalloporphyrins in electropolymerized films: design and applications. Acc. Chem. Res. 1995, 28, 30-36.
    • (1995) Acc. Chem. Res. , vol.28 , pp. 30-36
    • Bedioui, F.1    Devynck, J.2    Bied-Charreton, C.3
  • 117
    • 0000151701 scopus 로고
    • Electrochemical olefin epoxidation with manganese meso- tetraphenylporphyrin catalyst and hydrogen peroxide generation at polymer-coated electrodes
    • Nishihara, H.; Pressprich, K.; Murray, R. W.; Collman, J. P. Electrochemical olefin epoxidation with manganese meso-tetraphenylporphyrin catalyst and hydrogen peroxide generation at polymer-coated electrodes. Inorg. Chem. 1990, 29, 1000-1006.
    • (1990) Inorg. Chem. , vol.29 , pp. 1000-1006
    • Nishihara, H.1    Pressprich, K.2    Murray, R.W.3    Collman, J.P.4
  • 118
    • 0032513716 scopus 로고    scopus 로고
    • Synthesis and properties of metalloporphyrin monolayers and stacked multilayers bound to an electrode via site specific axial ligation to a self- assembled monolayers
    • DOI 10.1021/ja973528l
    • Offord, D. A.; Sachs, S. B.; Ennis, M. S.; Eberspacher, T. A.; Griffin, J. H.; Chidsey, C. E. D.; Collman, J. P. Synthesis and properties of metalloporphyrin monolayers and stacked multilayers bound to an electrode via site specific axial ligation to a self-assembled monolayer. J. Am. Chem. Soc. 1998, 720, 4478-4487. (Pubitemid 28261209)
    • (1998) Journal of the American Chemical Society , vol.120 , Issue.18 , pp. 4478-4487
    • Offord, D.A.1    Sachs, S.B.2    Ennis, M.S.3    Eberspacher, T.A.4    Griffin, J.H.5    Chidsey, C.E.D.6    Collman, J.P.7
  • 119
    • 0033639593 scopus 로고    scopus 로고
    • Preparation and characterization of a porphyrin self-assembled monolayer with a controlled orientation on gold
    • DOI 10.1021/la990570g
    • Zhang, Z.; Hou, S.; Zhu, Z.; Liu, Z. Preparation and characterization of a porphyrin self-assembled monolayer with a controlled orientation on gold. Langmuir 1999, 76, 537-540. (Pubitemid 32211248)
    • (2000) Langmuir , vol.16 , Issue.2 , pp. 537-540
    • Zhang, Z.1    Hou, S.2    Zhu, Z.3    Liu, Z.4
  • 120
    • 0000052205 scopus 로고
    • Mechanisms of hemin-catalyzed alkene epoxidation. The effect of catalyst on the regiochemistry of epoxidation
    • Traylor, T. G.; Nakano, T.; Dunlap, B. E.; Traylor, P. S.; Dolphin, D. Mechanisms of hemin-catalyzed alkene epoxidation. The effect of catalyst on the regiochemistry of epoxidation. J. Am. Chem. Soc. 1986, 708, 2782-2784.
    • (1986) J. Am. Chem. Soc. , vol.708 , pp. 2782-2784
    • Traylor, T.G.1    Nakano, T.2    Dunlap, B.E.3    Traylor, P.S.4    Dolphin, D.5
  • 121
    • 34247399604 scopus 로고    scopus 로고
    • Voltammetric and surface-enhanced resonance Raman spectroscopic characterization of cytochrome c adsorbed on a 4-mercaptopyridine monolayer on silver electrodes
    • DOI 10.1021/la062668i
    • Millo, D.; Bonifacio, A.; Ranieri, A.; Borsari, M.; Gooijer, C.; van der Zwan, G. Voltammetric and surface-enhanced resonance Raman spectroscopic characterization of Cytochrome c adsorbed on a 4-mercaptopyridine monolayer on silver electrodes. Langmuir 2007, 23, 4340-4345. (Pubitemid 46643159)
    • (2007) Langmuir , vol.23 , Issue.8 , pp. 4340-4345
    • Millo, D.1    Bonifacio, A.2    Ranieri, A.3    Borsari, M.4    Gooijer, C.5    Van Der Zwan, G.6
  • 122
    • 0033637505 scopus 로고    scopus 로고
    • Selective oxygen transfer catalysed by heme peroxidases: Synthetic and mechanistic aspects
    • van Rantwijk, F.; Sheldon, R. A. Selective oxygen transfer catalysed by heme peroxidases: synthetic and mechanistic aspects. Curr. Opin. Biotechnol. 2000, 77, 554-564.
    • (2000) Curr. Opin. Biotechnol. , vol.77 , pp. 554-564
    • Van Rantwijk, F.1    Sheldon, R.A.2
  • 123
    • 0029086104 scopus 로고
    • Hydroxylation of benzene by horseradish peroxidase and immobilized horseradish peroxidase in an organic solvent
    • Akasaka, R.; Mashino, T.; Hirobe, M. Hydroxylation of benzene by horseradish peroxidase and immobilized horseradish peroxidase in an organic solvent. Bioorg. Med. Chem. Lett. 1995, 5, 1861-1864.
    • (1995) Bioorg. Med. Chem. Lett. , vol.5 , pp. 1861-1864
    • Akasaka, R.1    Mashino, T.2    Hirobe, M.3
  • 124
    • 0033526314 scopus 로고    scopus 로고
    • Selective oxidations with molecular oxygen, catalyzed by chloroperoxidase in the presence of a reductant
    • DOI 10.1016/S1381-1169(99)00059-X, PII S138111699900059X
    • van de Velde, F.; van Rantwijk, F.; Sheldon, R. A. Selective oxidations with molecular oxygen, catalyzed by chloroperoxidase in the presence of a reductant. J. Mol. Catal, B Enzym. 1999, 6, 453-461. (Pubitemid 29191032)
    • (1999) Journal of Molecular Catalysis - B Enzymatic , vol.6 , Issue.5 , pp. 453-461
    • Van De Velde, F.1    Van Rantwijk, F.2    Sheldon, R.A.3
  • 125
    • 0035471139 scopus 로고    scopus 로고
    • Peptide-based heme-protein models
    • DOI 10.1021/cr000055j
    • Lombardi, A.; Nastri. F.; Pavone, V. Peptide-based heme-protein models. Chem. Rev. 2001, 707, 3165-3189. (Pubitemid 35377816)
    • (2001) Chemical Reviews , vol.101 , Issue.10 , pp. 3165-3189
    • Lombardi, A.1    Nastri, F.2    Pavone, V.3
  • 128
    • 0033204150 scopus 로고    scopus 로고
    • Electroenzyme-catalyzed oxidation of styrene and cis-β-methylstyrene using thin films of cytochrome P450cam and myoglobin
    • DOI 10.1021/la990685k
    • Zu, X.; Lu, Z.; Zhang, Z.; Schenkman, J. B.; Rusling, J. F. Elec-troenzyme-catalyzed oxidation of styrene and cis-p-methylstyrene using thin films of Cytochrome P450cam and myoglobin. Lang-muir 1999, 75, 7372-7377. (Pubitemid 32079668)
    • (1999) Langmuir , vol.15 , Issue.21 , pp. 7372-7377
    • Zu, X.1    Lu, Z.2    Zhang, Z.3    Schenkman, J.B.4    Rusling, J.F.5
  • 129
    • 25844509942 scopus 로고    scopus 로고
    • Protein film electrochemistry of microsomes genetically enriched in human cytochrome P450 monooxygenases
    • DOI 10.1021/ja0538334
    • Sultana, N.; Schenkman, J. B.; Rusling, J. F. Protein film electrochemistry of microsomes genetically enriched in human Cyto-chrome P450 monooxygenases. J. Am. Chem. Soc. 2005, 727, 13460-13461. (Pubitemid 41401175)
    • (2005) Journal of the American Chemical Society , vol.127 , Issue.39 , pp. 13460-13461
    • Sultana, N.1    Schenkman, J.B.2    Rusling, J.F.3
  • 130
    • 67650517516 scopus 로고    scopus 로고
    • Electrochemically driven drug metabolism by membranes containing human Cytochrome P450
    • Mie, Y.; Suzuki, M.; Komatsu, Y. Electrochemically driven drug metabolism by membranes containing human Cytochrome P450. J. Am. Chem. Soc. 2009, 737, 6646-6647.
    • (2009) J. Am. Chem. Soc. , vol.737 , pp. 6646-6647
    • Mie, Y.1    Suzuki, M.2    Komatsu, Y.3
  • 131
    • 0036134828 scopus 로고    scopus 로고
    • Molecular Lego: Design of molecular assemblies of P450 enzymes for nanobiotechnology
    • DOI 10.1016/S0956-5663(01)00286-X, PII S095656630100286X
    • Gilardi, G.; Meharenna, Y. T.; Tsotsou, G. E.; Sadeghi, S. J.; Fair-head, M.; Giannini, S. Molecular Lego: design of molecular assemblies of P450 enzymes for nanobiotechnology. Biosens. Bioelectron. 2002, 7 7, 133-145. (Pubitemid 34003619)
    • (2002) Biosensors and Bioelectronics , vol.17 , Issue.1-2 , pp. 133-145
    • Gilardi, G.1    Meharenna, Y.T.2    Tsotsou, G.E.3    Sadeghi, S.J.4    Fairhead, M.5    Giannini, S.6
  • 132
  • 133
    • 74949140470 scopus 로고    scopus 로고
    • Direct electrochemistry of drug metabolizing human flavin-containing monooxygenase: Electrochemical turnover of benzydamine and tamoxifen
    • Sadeghi, S. J.; Meirinhos, R.; Catucci, G.; Dodhia, V. R.; Nardo, G. D.; Gilardi, G. Direct electrochemistry of drug metabolizing human flavin-containing monooxygenase: Electrochemical turnover of benzydamine and tamoxifen. J. Am. Chem. Soc. 2010, 732, 458-459.
    • (2010) J. Am. Chem. Soc. , vol.732 , pp. 458-459
    • Sadeghi, S.J.1    Meirinhos, R.2    Catucci, G.3    Dodhia, V.R.4    Nardo, G.D.5    Gilardi, G.6
  • 134
    • 77953554845 scopus 로고    scopus 로고
    • Control of human Cytochrome P450 2E1 electrocatalytic response as a result of unique orientation on gold electrodes
    • Mak, L. H.; Sadeghi, S. J.; Fantuzzi, A.; Gilardi, G. Control of human Cytochrome P450 2E1 electrocatalytic response as a result of unique orientation on gold electrodes. Anal. Chem. 2010, 82, 5357-5362.
    • (2010) Anal. Chem. , vol.82 , pp. 5357-5362
    • Mak, L.H.1    Sadeghi, S.J.2    Fantuzzi, A.3    Gilardi, G.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.