메뉴 건너뛰기




Volumn 65, Issue , 2014, Pages 45-55

Imitation of phase i oxidative metabolism of anabolic steroids by titanium dioxide photocatalysis

Author keywords

Biomimetics; Mass spectrometry; Metabolism; Oxidation; Steroids; Titanium dioxide photocatalysis

Indexed keywords

ACETONITRILE; ANABOLIC AGENT; METANDIENONE; METHYLTESTOSTERONE; NANDROLONE; STANOZOLOL; TESTOSTERONE; TITANIUM DIOXIDE; STEROID; TITANIUM;

EID: 84907521827     PISSN: 09280987     EISSN: 18790720     Source Type: Journal    
DOI: 10.1016/j.ejps.2014.08.009     Document Type: Article
Times cited : (15)

References (49)
  • 1
    • 84865408037 scopus 로고    scopus 로고
    • Investigating the oxidation of alkenes by non-heme iron enzyme mimics
    • S.M. Barry, H. Mueller-Bunz, and P.J. Rutledge Investigating the oxidation of alkenes by non-heme iron enzyme mimics Org. Biomol. Chem. 10 2012 7372 7381
    • (2012) Org. Biomol. Chem. , vol.10 , pp. 7372-7381
    • Barry, S.M.1    Mueller-Bunz, H.2    Rutledge, P.J.3
  • 2
    • 1942439085 scopus 로고    scopus 로고
    • Biomimetic chemical catalysts in the oxidative activation of drugs
    • J. Bernadou, and B. Meunier Biomimetic chemical catalysts in the oxidative activation of drugs Adv. Synth. Catal. 346 2004 171 184
    • (2004) Adv. Synth. Catal. , vol.346 , pp. 171-184
    • Bernadou, J.1    Meunier, B.2
  • 6
    • 0030976987 scopus 로고    scopus 로고
    • Selective catalytic hydroxylation of a steroid by an artificial cytochrome P-450 enzyme
    • R. Breslow, X. Zhang, and Y. Huang Selective catalytic hydroxylation of a steroid by an artificial cytochrome P-450 enzyme J. Am. Chem. Soc. 119 1997 4535 4536
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 4535-4536
    • Breslow, R.1    Zhang, X.2    Huang, Y.3
  • 8
    • 0345490845 scopus 로고    scopus 로고
    • Effect of methanol, ethanol, dimethyl sulfoxide, and acetonitrile on in vitro activities of cDNA-expressed human cytochromes P-450
    • W.F. Busby, J.M. Ackermann, and C.L. Crespi Effect of methanol, ethanol, dimethyl sulfoxide, and acetonitrile on in vitro activities of cDNA-expressed human cytochromes P-450 Drug Metab. Dispos. 27 1999 246 249
    • (1999) Drug Metab. Dispos. , vol.27 , pp. 246-249
    • Busby, W.F.1    Ackermann, J.M.2    Crespi, C.L.3
  • 10
    • 1642376505 scopus 로고    scopus 로고
    • The photocatalytic process as a tool to identify metabolitic products formed from dopant substances: The case of buspirone
    • P. Calza, M. Pazzi, C. Medana, C. Baiocchi, and E. Pelizzetti The photocatalytic process as a tool to identify metabolitic products formed from dopant substances: the case of buspirone J. Pharm. Biomed. Anal. 35 2004 9 19
    • (2004) J. Pharm. Biomed. Anal. , vol.35 , pp. 9-19
    • Calza, P.1    Pazzi, M.2    Medana, C.3    Baiocchi, C.4    Pelizzetti, E.5
  • 11
    • 0031940804 scopus 로고    scopus 로고
    • Effect of common organic solvents on in vitro cytochrome P450-mediated metabolic activities in human liver microsomes
    • N. Chauret, A. Gauthier, and D.A. Nicoll-Griffith Effect of common organic solvents on in vitro cytochrome P450-mediated metabolic activities in human liver microsomes Drug Metab. Dispos. 26 1998 1 4
    • (1998) Drug Metab. Dispos. , vol.26 , pp. 1-4
    • Chauret, N.1    Gauthier, A.2    Nicoll-Griffith, D.A.3
  • 12
    • 18844446231 scopus 로고    scopus 로고
    • Characterization of testosterone 11 beta-hydroxylation catalyzed by human liver microsomal cytochromes P450
    • M.H. Choi, P.L. Skipper, J.S. Wishnok, and S.R. Tannenbaum Characterization of testosterone 11 beta-hydroxylation catalyzed by human liver microsomal cytochromes P450 Drug Metab. Dispos. 33 2005 714 718
    • (2005) Drug Metab. Dispos. , vol.33 , pp. 714-718
    • Choi, M.H.1    Skipper, P.L.2    Wishnok, J.S.3    Tannenbaum, S.R.4
  • 14
    • 31544447429 scopus 로고    scopus 로고
    • Metal coordination-directed hydroxylation of steroids with a novel artificial P-450 catalyst
    • Z. Fang, and R. Breslow Metal coordination-directed hydroxylation of steroids with a novel artificial P-450 catalyst Org. Lett. 8 2006 251 254
    • (2006) Org. Lett. , vol.8 , pp. 251-254
    • Fang, Z.1    Breslow, R.2
  • 15
    • 18544384019 scopus 로고
    • LXXIII.-Oxidation of tartaric acid in presence of iron
    • H.J.H. Fenton LXXIII.-Oxidation of tartaric acid in presence of iron. J. Chem. Soc., Trans. 65 1894 899 910
    • (1894) J. Chem. Soc., Trans. , vol.65 , pp. 899-910
    • Fenton, H.J.H.1
  • 18
    • 84867671775 scopus 로고    scopus 로고
    • Impact of organic solvents on cytochrome P450 probe reactions: Filling the gap with (S)-Warfarin and Midazolam hydroxylation
    • V. Gonzalez-Perez, E.A. Connolly, A.S. Bridges, L.C. Wienkers, and M.F. Paine Impact of organic solvents on cytochrome P450 probe reactions: filling the gap with (S)-Warfarin and Midazolam hydroxylation Drug Metab. Dispos. 40 2012 2136 2142
    • (2012) Drug Metab. Dispos. , vol.40 , pp. 2136-2142
    • Gonzalez-Perez, V.1    Connolly, E.A.2    Bridges, A.S.3    Wienkers, L.C.4    Paine, M.F.5
  • 19
    • 34250942854 scopus 로고
    • Über die Katalyse des Hydroxyperoxydes
    • V.F. Haber, and J. Weiss Über die Katalyse des Hydroxyperoxydes Naturwissenschaften 20 1932 948 950
    • (1932) Naturwissenschaften , vol.20 , pp. 948-950
    • Haber, V.F.1    Weiss, J.2
  • 20
    • 0031921010 scopus 로고    scopus 로고
    • Evaluation of the selectivity of in vitro probes and suitability of organic solvents for the measurement of human cytochrome P450 monooxygenase activities
    • D. Hickman, J.P. Wang, Y. Wang, and J.D. Unadkat Evaluation of the selectivity of in vitro probes and suitability of organic solvents for the measurement of human cytochrome P450 monooxygenase activities Drug Metab. Dispos. 26 1998 207 215
    • (1998) Drug Metab. Dispos. , vol.26 , pp. 207-215
    • Hickman, D.1    Wang, J.P.2    Wang, Y.3    Unadkat, J.D.4
  • 21
    • 34547165961 scopus 로고    scopus 로고
    • Mimicry of phase i drug metabolism - Novel methods for metabolite characterization and synthesis
    • T. Johansson, L. Weidolf, and U. Jurva Mimicry of phase I drug metabolism - novel methods for metabolite characterization and synthesis Rapid Commun. Mass Spectrom. 21 2007 2323 2331
    • (2007) Rapid Commun. Mass Spectrom. , vol.21 , pp. 2323-2331
    • Johansson, T.1    Weidolf, L.2    Jurva, U.3
  • 22
    • 0036388293 scopus 로고    scopus 로고
    • Electrochemically assisted Fenton reaction: Reaction of hydroxyl radicals with xenobiotics followed by on-line analysis with high-performance liquid chromatography/tandem mass spectrometry
    • U. Jurva, H.V. Wikstrom, and A.P. Bruins Electrochemically assisted Fenton reaction: reaction of hydroxyl radicals with xenobiotics followed by on-line analysis with high-performance liquid chromatography/tandem mass spectrometry Rapid Commun. Mass Spectrom. 16 2002 1934 1940
    • (2002) Rapid Commun. Mass Spectrom. , vol.16 , pp. 1934-1940
    • Jurva, U.1    Wikstrom, H.V.2    Bruins, A.P.3
  • 23
    • 0037258065 scopus 로고    scopus 로고
    • Comparison between electrochemistry/mass spectrometry and cytochrome P450 catalyzed oxidation reactions
    • U. Jurva, H.V. Wikstrom, L. Weidolf, and A.P. Bruins Comparison between electrochemistry/mass spectrometry and cytochrome P450 catalyzed oxidation reactions Rapid Commun. Mass Spectrom. 17 2003 800 810
    • (2003) Rapid Commun. Mass Spectrom. , vol.17 , pp. 800-810
    • Jurva, U.1    Wikstrom, H.V.2    Weidolf, L.3    Bruins, A.P.4
  • 25
    • 67650792478 scopus 로고    scopus 로고
    • Evaluation of luciferin-isopropyl acetal as a CYP3A4 substrate for human hepatocytes: Effects of organic solvents, cytochrome P450 (P450) inhibitors, and P450 inducers
    • A.P. Li Evaluation of luciferin-isopropyl acetal as a CYP3A4 substrate for human hepatocytes: effects of organic solvents, cytochrome P450 (P450) inhibitors, and P450 inducers Drug Metab. Dispos. 37 2009 1598 1603
    • (2009) Drug Metab. Dispos. , vol.37 , pp. 1598-1603
    • Li, A.P.1
  • 26
    • 84879064573 scopus 로고    scopus 로고
    • Solvent effects and improvements in the deoxyribose degradation assay for hydroxyl radical-scavenging
    • X. Li Solvent effects and improvements in the deoxyribose degradation assay for hydroxyl radical-scavenging Food Chem. 141 2013 2083 2088
    • (2013) Food Chem. , vol.141 , pp. 2083-2088
    • Li, X.1
  • 27
    • 84881400662 scopus 로고    scopus 로고
    • Online monitoring oxidative products and metabolites of nicotine by free radicals generation with Fenton reaction in tandem mass spectrometry
    • 189162-189162
    • S. Liang, Y. Shiue, C. Kuo, S. Guo, W. Liao, and E. Tsai Online monitoring oxidative products and metabolites of nicotine by free radicals generation with Fenton reaction in tandem mass spectrometry Sci. World J. 2013 2013 189162-189162
    • (2013) Sci. World J. , vol.2013
    • Liang, S.1    Shiue, Y.2    Kuo, C.3    Guo, S.4    Liao, W.5    Tsai, E.6
  • 28
    • 0024846386 scopus 로고
    • Studies on anabolic-steroids. 3. Detection and characterization of stanozolol urinary metabolites in humans by gas-chromatography mass-spectrometry
    • R. Masse, C. Ayotte, H.G. Bi, and R. Dugal Studies on anabolic-steroids. 3. Detection and characterization of stanozolol urinary metabolites in humans by gas-chromatography mass-spectrometry J. Chromatogr. B. Biomed. Appl. 497 1989 17 37
    • (1989) J. Chromatogr. B. Biomed. Appl. , vol.497 , pp. 17-37
    • Masse, R.1    Ayotte, C.2    Bi, H.G.3    Dugal, R.4
  • 29
    • 84857093878 scopus 로고    scopus 로고
    • Horse metabolism and the photocatalytic process as a tool to identify metabolic products formed from dopant substances: The case of sildenafil
    • C. Medana, P. Calza, V. Giancotti, F. Dal Bello, E. Pasello, M. Montana, and C. Baiocchi Horse metabolism and the photocatalytic process as a tool to identify metabolic products formed from dopant substances: the case of sildenafil Drug Test. Anal. 3 2011 724 734
    • (2011) Drug Test. Anal. , vol.3 , pp. 724-734
    • Medana, C.1    Calza, P.2    Giancotti, V.3    Dal Bello, F.4    Pasello, E.5    Montana, M.6    Baiocchi, C.7
  • 30
    • 84873725165 scopus 로고    scopus 로고
    • Study of the photocatalytic transformation of synephrine: A biogenic amine relevant in anti-doping analysis
    • C. Medana, P. Calza, V. Giancotti, F. Dal Bello, M. Aragno, and C. Baiocchi Study of the photocatalytic transformation of synephrine: a biogenic amine relevant in anti-doping analysis Anal. Bioanal. Chem. 405 2013 1105 1113
    • (2013) Anal. Bioanal. Chem. , vol.405 , pp. 1105-1113
    • Medana, C.1    Calza, P.2    Giancotti, V.3    Dal Bello, F.4    Aragno, M.5    Baiocchi, C.6
  • 31
    • 0011697055 scopus 로고
    • Metalloporphyrins as versatile catalysts for oxidation reactions and oxidative DNA cleavage
    • B. Meunier Metalloporphyrins as versatile catalysts for oxidation reactions and oxidative DNA cleavage Chem. Rev. 92 1992 1411 1456
    • (1992) Chem. Rev. , vol.92 , pp. 1411-1456
    • Meunier, B.1
  • 32
    • 0034087939 scopus 로고    scopus 로고
    • Free radical participation in organic chemistry: Electron Spin Resonance (ESR) studies of their structures and reactions
    • B. Mile Free radical participation in organic chemistry: Electron Spin Resonance (ESR) studies of their structures and reactions Curr. Org. Chem. 4 2000 55 83
    • (2000) Curr. Org. Chem. , vol.4 , pp. 55-83
    • Mile, B.1
  • 33
    • 79953195567 scopus 로고    scopus 로고
    • Integrated photocatalytic micropillar nanoreactor electrospray ionization chip for mimicking phase i metabolic reactions
    • T. Nissilä, L. Sainiemi, M. Karikko, M. Kemell, M. Ritala, S. Franssila, R. Kostiainen, and R.A. Ketola Integrated photocatalytic micropillar nanoreactor electrospray ionization chip for mimicking phase I metabolic reactions Lab Chip 11 2011 1470 1476
    • (2011) Lab Chip , vol.11 , pp. 1470-1476
    • Nissilä, T.1    Sainiemi, L.2    Karikko, M.3    Kemell, M.4    Ritala, M.5    Franssila, S.6    Kostiainen, R.7    Ketola, R.A.8
  • 34
    • 79953656393 scopus 로고    scopus 로고
    • Electrochemistry in the mimicry of oxidative drug metabolism by cytochrome P450s
    • E. Nouri-Nigjeh, R. Bischoff, A.P. Bruins, and H.P. Permentier Electrochemistry in the mimicry of oxidative drug metabolism by cytochrome P450s Curr. Drug Metab. 12 2011 359 371
    • (2011) Curr. Drug Metab. , vol.12 , pp. 359-371
    • Nouri-Nigjeh, E.1    Bischoff, R.2    Bruins, A.P.3    Permentier, H.P.4
  • 35
    • 84865436734 scopus 로고    scopus 로고
    • Unexpected contribution of cytochrome P450 enzymes CYP11B2 and CYP21, as well as CYP3A4 in xenobiotic androgen elimination - Insights from metandienone metabolism
    • M.K. Parr, A. Zöllner, G. Fußhöller, G. Opfermann, N. Schlörer, M. Zorio, M. Bureik, and W. Schänzer Unexpected contribution of cytochrome P450 enzymes CYP11B2 and CYP21, as well as CYP3A4 in xenobiotic androgen elimination - insights from metandienone metabolism Toxicol. Lett. 213 2012 381 391
    • (2012) Toxicol. Lett. , vol.213 , pp. 381-391
    • Parr, M.K.1    Zöllner, A.2    Fußhöller, G.3    Opfermann, G.4    Schlörer, N.5    Zorio, M.6    Bureik, M.7    Schänzer, W.8
  • 40
    • 33846928519 scopus 로고    scopus 로고
    • Quantitation of 17 beta-nandrolone metabolites in boar and horse urine by gas chromatography-mass spectrometry
    • M. Roig, J. Segura, and R. Ventura Quantitation of 17 beta-nandrolone metabolites in boar and horse urine by gas chromatography-mass spectrometry Anal. Chim. Acta 586 2007 184 195
    • (2007) Anal. Chim. Acta , vol.586 , pp. 184-195
    • Roig, M.1    Segura, J.2    Ventura, R.3
  • 41
    • 71849112570 scopus 로고    scopus 로고
    • The application of in vitro technologies to study the metabolism of the androgenic/anabolic steroid stanozolol in the equine
    • J.P. Scarth, H.A. Spencer, S.C. Hudson, P. Teale, B.P. Gray, and L.L. Hillyer The application of in vitro technologies to study the metabolism of the androgenic/anabolic steroid stanozolol in the equine Steroids 75 2010 57 69
    • (2010) Steroids , vol.75 , pp. 57-69
    • Scarth, J.P.1    Spencer, H.A.2    Hudson, S.C.3    Teale, P.4    Gray, B.P.5    Hillyer, L.L.6
  • 42
    • 0029987681 scopus 로고    scopus 로고
    • Metabolism of anabolic androgenic steroids
    • W. Schänzer Metabolism of anabolic androgenic steroids Clin. Chem. 42 1996 1001 1020
    • (1996) Clin. Chem. , vol.42 , pp. 1001-1020
    • Schänzer, W.1
  • 43
    • 0025854367 scopus 로고
    • Metabolism of metandienone in man - Identification and synthesis of conjugated excreted urinary metabolites, determination of excretion rates and gas-chromatographic mass-spectrometric identification of bis-hydroxylated metabolites
    • W. Schänzer, H. Geyer, and M. Donike Metabolism of metandienone in man - identification and synthesis of conjugated excreted urinary metabolites, determination of excretion rates and gas-chromatographic mass-spectrometric identification of bis-hydroxylated metabolites J. Steroid Biochem. Mol. Biol. 38 1991 441 464
    • (1991) J. Steroid Biochem. Mol. Biol. , vol.38 , pp. 441-464
    • Schänzer, W.1    Geyer, H.2    Donike, M.3
  • 44
    • 0025892464 scopus 로고
    • Site-selective hydroxylation of steroids via oxometalloporphinates covalently linked to ring-D - Introduction of hydroxyl-groups into the C(9) and C(12) position of 5-alpha-androstanes
    • T.L. Stuk, P.A. Grieco, and M.M. Marsh Site-selective hydroxylation of steroids via oxometalloporphinates covalently linked to ring-D - introduction of hydroxyl-groups into the C(9) and C(12) position of 5-alpha-androstanes J. Org. Chem. 56 1991 2957 2959
    • (1991) J. Org. Chem. , vol.56 , pp. 2957-2959
    • Stuk, T.L.1    Grieco, P.A.2    Marsh, M.M.3
  • 45
    • 0015941039 scopus 로고
    • 4-Hydroperoxidation in fenton oxidation of antitumor agent cyclophosphamide
    • J. Van der Steen, E.C. Timmer, J.G. Westra, and C. Benckhuysen 4-Hydroperoxidation in fenton oxidation of antitumor agent cyclophosphamide J. Am. Chem. Soc. 95 1973 7535 7536
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 7535-7536
    • Van Der Steen, J.1    Timmer, E.C.2    Westra, J.G.3    Benckhuysen, C.4
  • 46
    • 0031260323 scopus 로고    scopus 로고
    • Progesterone and testosterone hydroxylation by cytochromes P450 2C19, 2C9, and 3A4 in human liver microsomes
    • H. Yamazaki, and T. Shimada Progesterone and testosterone hydroxylation by cytochromes P450 2C19, 2C9, and 3A4 in human liver microsomes Arch. Biochem. Biophys. 346 1997 161 169
    • (1997) Arch. Biochem. Biophys. , vol.346 , pp. 161-169
    • Yamazaki, H.1    Shimada, T.2
  • 47
    • 0034604638 scopus 로고    scopus 로고
    • Selective hydroxylation of a steroid at C-9 by an artificial cytochrome P-450
    • J. Yang, and R. Breslow Selective hydroxylation of a steroid at C-9 by an artificial cytochrome P-450 Angew. Chem. Int. Ed. Engl. 39 2000 2692 2694
    • (2000) Angew. Chem. Int. Ed. Engl. , vol.39 , pp. 2692-2694
    • Yang, J.1    Breslow, R.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.