Electrochemical simulation of cocaine metabolism-a step toward predictive toxicology for drugs of abuse

European Journal of Mass Spectrometry

Volumn 20, Issue 4, 2014, Pages 279-285

  Mielczarek, Przemyslaw ^a   Raoof, Hana ^a   Kotlinska, Jolanta H ^b   Stefanowicz, Piotr ^c   Szewczuk, Zbigniew ^c   Suder, Piotr ^a   Silberring, Jerzy ^b,d  

^a AGH UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Poland)

^b MEDICAL UNIVERSITY OF LUBLIN   (Poland)

^c UNIVERSITY OF WROC AW   (Poland)

^d POLISH ACADEMY OF SCIENCES   (Poland)

Author keywords

Cocaine; Electrochemistry; Mass spectrometry; Metabolism; Norcocaine

Indexed keywords

BIOMOLECULES; DRUG PRODUCTS; ELECTROSPRAY IONIZATION; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLISM; METABOLITES;

COCAINE; ELECTROCHEMICAL SIMULATION; ELECTROCHEMICAL SYSTEMS; ELECTROSPRAY IONIZATION MASS SPECTROMETRY; NORCOCAINE; OXIDATIVE METABOLISM; RAT LIVER MICROSOMES; STANDARD PROCEDURES;

ELECTROCHEMISTRY;

COCAINE; NORCOCAINE; STREET DRUG;

ANALOGS AND DERIVATIVES; ANIMAL; ELECTROCHEMICAL ANALYSIS; ELECTROSPRAY MASS SPECTROMETRY; LIVER MICROSOME; MALE; METABOLISM; PROCEDURES; WISTAR RAT;

ANIMALS; COCAINE; ELECTROCHEMICAL TECHNIQUES; MALE; MICROSOMES, LIVER; RATS, WISTAR; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STREET DRUGS;

EID: 84924962667     PISSN: None     EISSN: 17516838     Source Type: Journal    
DOI: 10.1255/ejms.1284     Document Type: Article

References (24)

1. B. Meunier, S.P. de Visser and S. Shaik, "Mechanism of oxidation reactions catalyzed by cytochrome p450 enzymes", Chem. Rev. 104, 3947 (2004). doi: http//dx.doi.org/http//dx.doi.org/10.1021/cr020443g
2. L. Wang, A. Tan, S. Zhao, G. Lv and X. Ma, "Study on human UDP-glucuronosyltransferase (UGT) isoforms involved in in vitro metabolism of trans-resveratrol", Zhongguo Zhong Yao Za Zhi 37, 524 (2012).
3. W. Lohmann and U. Karst, "Simulation of the detoxificationof paracetamol using on-line electrochemistry/ liquidchromatography/ mass spectrometry", Anal. Bioanal. Chem. 386, 1701 (2006). doi: http//dx.doi.org/10.1007/s00216-006-0801-y
4. H.P. Permentier, A.P. Bruins and R. Bischoff, "Electrochemistry-mass spectrometry in drug metabolism and protein research", Mini Rev. Med. Chem. 8, 46 (2008). doi: http://dx.doi.org/10.2174/138955708783331586
5. T.A. Getek, W.A. Korfmacher, T.A. McRae and J.A. Hinson, "Utility of solution electrochemistry mass spectrometryfor investigating the formation and detectionof biologically important conjugates of acetaminophen", J. Chromatogr. 474, 245 (1989). doi: http://dx.doi.org/10.1016/S0021-9673(01)93919- 6
6. S. Jahn and U. Karst, "Electrochemistry coupled to (liquid chromatography/) mass spectrometry-current state and future perspectives", J. Chromatogr. A 1259, 16 (2012). doi: http//dx.doi.org/10.1016/j.chroma.2012. 05.066
7. 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, 800 (2003). doi: http//dx.doi.org/10.1002/rcm.978
8. C. Huber, B. Bartha, R. Harpaintner and P. Schroder, "Metabolism of acetaminophen (paracetamol) in plants- two independent pathways result in the formation of a glutathione and a glucose conjugate", Environ. Sci. Pollut. Res. Int. 16, 206 (2009). doi: http//dx.doi.org/10.1007/ s11356-008-0095-z
9. W. Lohmann, U. Karst and A. Baumann, "Electrochemistry and LC-MS for metabolite generation and identification: tools, technologies and trends", LCGC Europe 23, 8 (2010).
10. A. Baumann and U. Karst, "Online electrochemistry/ mass spectrometry in drug metabolism studies: principles and applications", Expert Opin. Drug. Metab. Toxicol. 6, 715 (2010). doi: http//dx.doi.org/10.1517/ 17425251003713527
11. F.P. Guengerich, "Cytochrome p450 and chemical toxicology", Chem. Res. Toxicol. 21, 70 (2008). doi: http//dx.doi.org/10.1021/tx700079z
12. M.G. Ladona, M.L. Gonzalez, A. Rane, R.M. Peter and R. de la Torre, "Cocaine metabolism in human fetal and adult liver microsomes is related to cytochrome P450 3A expression", Life Sci. 68, 431 (2000). doi: http//dx.doi.org/10.1016/S0024-3205(00)00952-8
13. P. Pellinen, L. Kulmala, J. Konttila, S. Auriola, M. Pasanen and R. Juvonen, "Kinetic characteristics of norcocaine N-hydroxylation in mouse and human liver microsomes: involvement of CYP enzymes", Arch. Toxicol. 74, 511 (2000). doi: http://dx.doi.org/10.1007/ s002040000154
14. L.Y. Lin, E.W. Di Stefano, D.A. Schmitz, L. Hsu, S.W. Ellis, M.S. Lennard, G.T. Tucker and A.K. Cho, "Oxidation of methamphetamine and methylenedioxymethamphetamine by CYP2D6", Drug Metab. Dispos. 25, 1059 (1997).
15. K. Kreth, K. Kovar, M. Schwab and U.M. Zanger, "Identification of the human cytochromes P450 involved in the oxidative metabolism of "Ecstasy"-related designer drugs", Biochem Pharmacol 59, 1563 (2000). doi: http://dx.doi.org/10.1016/S0006-2952(00)00284-7
16. M.V. Bach, R.T. Coutts and G.B. Baker, "Involvement of CYP2D6 in the in vitro metabolism of amphetamine, two N-alkylamphetamines and their 4-methoxylated derivatives", Xenobiotica 29, 719 (1999). doi: http//dx.doi.org/10.1080/004982599238344
17. P. Suder, A. Bodzon-Kulakowska, P. Mak, A. Bierczynska-Krzysik, M. Daszykowski, B. Walczak, G. Lubec, J.H. Kotlinska and J. Silberring, "The proteomic analysis of primary cortical astrocyte cell culture after morphine administration", J. Proteome Res. 8, 4633 (2009). doi: http//dx.doi.org/10. 1021/pr900443r
18. M. Modzel, P. Stefanowicz and Z. Szewczuk, "Hydrogen scrambling in non-covalent complexes of peptides", Rapid Commun. Mass Spectrom. 26, 2739 (2012). doi: http//dx.doi.org/10.1002/rcm.6396
19. S.S. Johansen and H.M. Bhatia, "Quantitative analysis of cocaine and its metabolites in whole blood and urine by high-performance liquid chromatography coupled with tandem mass spectrometry", J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 852, 338 (2007). doi: http// dx.doi.org/10.1016/j.jchromb.2007.01.033
20. S. Strano-Rossi, L. Anzillotti, E. Castrignano, M. Felli, G. Serpelloni, R. Mollica and M. Chiarotti, "UHPLCESI- MS/MS method for direct analysis of drugs of abuse in oral fluid for DUID assessment", Anal. Bioanal. Chem. 401, 609 (2011). doi: http//dx.doi.org/10.1007/s00216-011- 5108-y
21. J.R. Hill, "In vitro drug metabolism using liver microsomes", Curr. Protocols Pharmacol. 23, 7.doi: http// dx.doi.org/10.1002/0471141755. ph0708s23
22. Y. Yardim and Z. Senturk, "Electrochemical evaluation and adsorptive stripping voltammetric determination of capsaicin or dihydrocapsaicin on a disposable pencil graphite electrode", Talanta 112, 11 (2013). doi: http//dx.doi.org/10.1016/j.talanta.2013.03.047
23. 2 catalyzed by UV light", J Photochem Photobiol B 118, 49 (2013). doi: http//dx.doi.org/10.1016/j.jphotobiol.2012.10.013
24. U. Jurva, H.V. Wikstr?, L. Weidolf and A.P. Bruins, "Comparison between electrochemistry/mass spectrometry and cytochrome P450 catalyzed oxidation reactions", Rapid Commun. Mass Spectrom. 17, 800 (2003). doi: http//dx.doi.org/10.1002/rcm.978