Electrochemical generation of drug metabolites with applications in drug discovery and development

TrAC - Trends in Analytical Chemistry

Volumn 70, Issue , 2015, Pages 92-99

  Jurva, Ulrik ^a   Weidolf, Lars ^a  

^a ASTRAZENECA R AND D   (Sweden)

Author keywords

Bioactivation; Biotransformation; Cytochrome P450; Drug development; Drug discovery; Drug metabolism; Electrochemical generation; Electrochemistry; Metabolite synthesis; Reactive metabolite

Indexed keywords

BIOMOLECULES; DRUG PRODUCTS; ELECTROCHEMISTRY; METABOLITES; PHYSIOLOGY;

BIOACTIVATION; BIOTRANSFORMATION; CYTOCHROME P450; DRUG DEVELOPMENT; DRUG DISCOVERY; DRUG METABOLISMS; ELECTROCHEMICAL GENERATION; REACTIVE METABOLITES;

METABOLISM;

CYTOCHROME P450 1A1; CYTOCHROME P450 1B1; DRUG METABOLITE; RIMONABANT;

BINDING AFFINITY; BINDING SITE; BIOTRANSFORMATION; CHEMICAL STRUCTURE; CONTROLLED STUDY; COVALENT BOND; DRUG DESIGN; ELECTROCHEMICAL DETECTION; ELECTROCHEMISTRY; ENZYME METABOLISM; IN VITRO STUDY; INTERMETHOD COMPARISON; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REVIEW; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

EID: 84937969316     PISSN: 01659936     EISSN: 18793142     Source Type: Journal    
DOI: 10.1016/j.trac.2015.04.010     Document Type: Review

References (53)

1. Testa B., Krämer S.D. The biochemistry of drug metabolism - An introduction Part 1. Principles and overview. Chem. Biodivers 2006, 3:1053-1101.
2. Testa B., Krämer S.D. The biochemistry of drug metabolism - An introduction part 2. Redox reactions and their enzymes. Chem. Biodivers 2007, 4:257-405.
3. Testa B., Krämer S.D. The biochemistry of drug metabolism - An introduction: Part 4. Reactions of conjugation and their enzymes. Chem. Biodivers 2008, 5:2171-2336.
4. Shono T., Toda T., Oshino N. Preparation of N-dealkylated drug metabolites by electrochemical simulation of biotransformation. Drug Metab. Dispos 1981, 9:481-482.
5. Shono T., Toda T., Oshino N. Electron transfer from nitrogen in microsomal oxidation of amine and amide. Simulation of microsomal oxidation by anodic oxidation. J. Am. Chem. Soc 1982, 104:2639-2641.
6. Hambitzer G., Heitbaum J. Electrochemical thermospray mass spectrometry. Anal. Chem 1986, 58:1067-1070.
7. Getek T.A., Korfmacher W.A., McRae T.A., Hinson J.A. Utility of solution electrochemistry mass spectrometry for investigating the formation and detection of biologically important conjugates of acetaminophen. J. Chromatogr 1989, 474:245-256.
8. Volk K.J., Yost R.A., Brajter-Toth A. Electrochemistry on line with mass spectrometry: insight into biological redox reactions. Anal. Chem 1992, 64:21A-33A.
9. Baumann A., Karst U. Online electrochemistry/mass spectrometry in drug metabolism studies: principles and applications. Expert Opin. Drug Met. Toxicol 2010, 6:715-731.
10. Nouri-Nigjeh E., Bischoff R., Bruins A.P., Permentier H.P. Electrochemistry in the mimicry of oxidative drug metabolism by cytochrome P450s. Curr. Drug Metab 2011, 12:359-371.
11. Jahn S., Karst U. Electrochemistry coupled to (liquid chromatography/) mass spectrometry-Current state and future perspectives. J. Chromatogr. A 2012, 1259:16-49.
12. Nowak P., Wozniakiewicz M., Koscielniak P. Simulation of drug metabolism. TrAC Trends Anal. Chem 2014, 59:42-49.
13. Yoshioka K., Kato D., Kamata T., Niwa O. Cytochrome P450 modified polycrystalline indium tin oxide film as a drug metabolizing electrochemical biosensor with a simple configuration. Anal. Chem 2013, 85:9996-9999.
14. Nouri-Nigjeh E., Bruins A.P., Bischoff R., Permentier H.P. Electrocatalytic oxidation of hydrogen peroxide on a platinum electrode in the imitation of oxidative drug metabolism of lidocaine. Analyst 2012, 137:4698-4702.
15. Plowright A.T., Johnstone C., Kihlberg J., Pettersson J., Robb G., Thompson R.A. Hypothesis driven drug design: improving quality and effectiveness of the design-make-test-analyse cycle. Drug Discov. Today 2012, 17:56-62.
16. Korfmacher W.A. Advances in the integration of drug metabolism into the lead optimization paradigm. Mini Rev. Med. Chem 2009, 9:703-716.
17. Food and Drug Administration, Center for Drug Evaluation and Research (CDER) Guidance for Industry: Safety Testing of Drug Metabolites 2008, FDA, Silver Spring, MD.
18. European Medicines Agency, ICH Topic M3(R2): non-clinical safety studies for the conduct of human clinical trials and marketing authorization for pharmaceuticals, (2009) 2009.
19. Lewis R.J., Bernstein M.A., Duncan S.J., Sleigh C.J. A comparison of capillary-scale LC-NMR with alternative techniques: spectroscopic and practical considerations. Magn. Reson. Chem 2005, 43:783-789.
20. Jurva U., Holmén A., Grönberg 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.
21. Madsen K.G., Grönberg G., Skonberg C., Jurva U., Hansen S.H., Olsen J. Electrochemical oxidation of troglitazone: identification and characterization of the major reactive metabolite in liver microsomes. Chem. Res. Toxicol 2008, 21:2035-2041.
22. Stalder R., Roth G.P. Preparative microfluidic electrosynthesis of drug metabolites. ACS Med. Chem. Lett 2013, 4:1119-1123.
23. Pussard E., Verdier F., Faurisson F., Scherrmann J.M., Le Bras J., Blayo M.C. Disposition of monodesethylamodiaquine after a single oral dose of amodiaquine and three regimens for prophylaxis against Plasmodium falciparum malaria. Eur. J. Clin. Pharmacol 1987, 33:409-414.
24. Durrani N., Leslie T., Rahim S., Graham K., Ahmad F., Rowland M. Efficacy of combination therapy with artesunate plus amodiaquine compared to monotherapy with chloroquine, amodiaquine or sulfadoxine-pyrimethamine for treatment of uncomplicated Plasmodium falciparum in Afghanistan. Trop. Med. Int. Health 2005, 10:521-529.
25. Jewell H., Maggs J.L., Harrison A.C., O'neill P.M., Ruscoe J.E., Park B.K. Role of hepatic metabolism in the bioactivation and detoxication of amodiaquine. Xenobiotica 1995, 25:199-217.
26. Harrison A.C., Kitteringham N.R., Clarke J.B., Park B.K. The mechanism of bioactivation and antigen formation of amodiaquine in the rat. Biochem. Pharmacol 1992, 43:1421-1430.
27. Li X.Q., Björkman A., Andersson T.B., Ridderström M., Masimirembwa C.M. Amodiaquine clearance and its metabolism to N-desethylamodiaquine is mediated by CYP2C8: a new high affinity and turnover enzyme-specific probe substrate. J. Pharmacol. Exp. Ther 2002, 300:399-407.
28. Li X.Q., Björkman A., Andersson T.B., Gustafsson L.L., Masimirembwa C.M. Identification of human cytochrome P450s that metabolise anti-parasitic drugs and predictions of in vivo drug hepatic clearance from in vitro data. Eur. J. Clin. Pharmacol 2003, 59:429-442.
29. Johansson T., Jurva U., Grönberg G., Weidolf L., Masimirembwa 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.
30. Nouri-Nigjeh E., Permentier H.P., Bischoff R., Bruins A.P. Electrochemical oxidation by square-wave potential pulses in the imitation of oxidative drug metabolism. Anal. Chem 2011, 83:5519-5525.
31. Gillam E.M.J., Hayes M.A. The evolution of cytochrome P450 enzymes as biocatalysts in drug discovery and development. Curr. Top. Med. Chem 2013, 13:2254-2280.
32. Jurva U., Bissel P., Isin E.M., Igarashi K., Kuttab S., Castagnoli N. Model electrochemical-mass spectrometric studies of the cytochrome P450-catalyzed oxidations of cyclic tertiary allylamines. J. Am. Chem. Soc 2005, 127:12368-12377.
33. Thompson R.A., Isin E.M., Li Y., Weidolf L., Page K., Wilson I., et al. In vitro approach to assess the potential for risk of idiosyncratic adverse reactions caused by candidate drugs. Chem. Res. Toxicol 2012, 25:1616-1632.
34. Zhou F., Van Berkel G.J. Electrochemistry combined on-line with electrospray mass spectrometry. Anal. Chem 1995, 67:3643-3649.
35. Van Berkel G.J., Zhou F. Characterization of an electrospray ion source as a controlled-current electrolytic cell. Anal. Chem 1995, 67:2916-2923.
36. 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.
37. van den Brink F.T., Buter L., Odijk M., Olthuis W., Karst U., van den Berg A. Mass spectrometric detection of short-lived drug metabolites generated in an electrochemical microfluidic chip. Anal. Chem 2015, 87:1527-1535.
38. Bussy U., Giraudeau P., Tea I., Boujtita M. Understanding the degradation of electrochemically-generated reactive drug metabolites by quantitative NMR. Talanta 2013, 116:554-558.
39. Simon H., Melles D., Jacquoilleot S., Sanderson P., Zazzeroni R., Karst U. Combination of electrochemistry and nuclear magnetic resonance spectroscopy for metabolism studies. Anal. Chem 2012, 84:8777-8782.
40. Henness S., Robinson D.M., Lyseng-Williamson K.A. Rimonabant. Drugs 2006, 66:2109-2119.
41. Christensen R., Kristensen P.K., Bartels E.M., Bliddal H., Astrup A. Efficacy and safety of the weight-loss drug rimonabant: a meta-analysis of randomised trials. Lancet 2007, 370:1706-1713.
42. Bergström M.A., Isin E.M., Castagnoli N., Milne C.E. Bioactivation pathways of the cannabinoid receptor 1 antagonist rimonabant. Drug Metab. Dispos 2011, 39:1823-1832.
43. Johansson Mali'n T., Weidolf L., Castagnoli N., Jurva U. P450-catalyzed vs. electrochemical oxidation of haloperidol studied by ultra-performance liquid chromatography/electrospray ionization mass spectrometry. Rapid Commun. Mass Spectrom 2010, 24:1231-1240.
44. Organic Electrochemistry 2001, Marcel Dekker, Inc., Basel, Switzerland. fourth ed. H. Lund, O. Hammerich (Eds.).
45. Thorsell A., Isin E.M., Jurva U. Use of electrochemical oxidation and model peptides to study nucleophilic biological targets of reactive metabolites: the case of rimonabant. Chem. Res. Toxicol 2014, 27:1808-1820.
46. 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.
47. Bussy U., Boujtita M. Advances in the electrochemical simulation of oxidation reactions mediated by cytochrome P450. Chem. Res. Toxicol 2014, 27:1652-1668.
48. Zhang F., Dryhurst G. Influence of glutathione on the oxidation chemistry of the catecholaminergic neurotransmitter dopamine. J. Electroanal. Chem 1995, 398:117-128.
49. Lohmann W., Karst U. Generation and identification of reactive metabolites by electrochemistry and immobilized enzymes coupled on-line to liquid chromatography/mass spectrometry. Anal. Chem 2007, 79:6831-6839.
50. 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 vitro drug metabolism. Chem. Res. Toxicol 2007, 20:821-831.
51. Bussy U., Chung-Davidson Y.W., Li K., Li W. Phase I and phase II reductive metabolism simulation of nitro aromatic xenobiotics with electrochemistry coupled with high resolution mass spectrometry. Anal. Bioanal. Chem 2014, 406:7253-7260.
52. Lohmann W., Karst U. Electrochemistry meets enzymes: instrumental on-line simulation of oxidative and conjugative metabolism reactions of toremifene. Anal. Bioanal. Chem 2009, 394:1341-1348.
53. Afzelius L., Arnby C.H., Broo A., Carlsson L., Isaksson C., Jurva U., et al. State-of-the-art tools for computational site of metabolism predictions: comparative analysis, mechanistical insights, and future applications. Drug Metab. Rev 2007, 39:61-86.