Publication Cover
Xenobiotica
the fate of foreign compounds in biological systems
Volume 46, 2016 - Issue 1
303
Views
12
CrossRef citations to date
0
Altmetric
General Xenobiochemistry

Inhibitory effects and oxidation of 6-methylcoumarin, 7-methylcoumarin and 7-formylcoumarin via human CYP2A6 and its mouse and pig orthologous enzymes

, , , , , , , & show all
Pages 14-24 | Received 16 Mar 2015, Accepted 01 May 2015, Published online: 11 Jun 2015

References

  • Bayly CI, Ciepllak P, Cornell W, Kollman PA. (1993). A well-behaved electrostatic potential based method using charge restraints for deriving atomic charges. The RESP model. J Phys Chem 97:10269–80
  • Bogaards JJP, Bertrand M, Jackson P, et al. (2000). Determining the best animal model for human cytochrome P450 activities: a comparison of mouse, rat, rabbit, dog, micropig, monkey and man. Xenobiotica 30:1131–52
  • Born SL, Caudill D, Smith BJ, Lehman-McKeeman LD. (2000). In vitro kinetics of coumarin 3,4-epoxidation: application to species differences in toxicity and carcinogenicity. Toxicol Sci 58:23–31
  • Concannon S, Ramachandran VN, Smyth WF. (2000). A study of the electronspray ionization of selected coumarin derivatives and their subsequent fragmentation using an ion trap mass spectrometer. Rapid Commun Mass Spectrom 14:1157–66
  • Cruciani G. (2013). Metabolites: structure determination and prediction. Drug Discov Today 10:e145–6
  • Dalgaard L. (2015). Comparison of minipig, dog, monkey and human drug metabolism and disposition, J Pharmacol Toxicol Methods. [Epub ahead of print]. doi:10.1016/jvascn2014.12.005
  • DeLisle RK, Otten J, Rhodes S. (2011). In silico modeling of P450 substrates, inhibitors, activators, and inducers. Combin Chem High Throughput Screen 14:396–416
  • Foti RS, Wienkers LC, Wahlstrom JL. (2010). Application of cytochrome P450 drug interaction screening in drug discovery. Combin Chem High Throughput Screen 13:145–58
  • Giammona DA. (1984). Force field modifications for united atom heme plus flexible water N.B. the parameters around the iron are appropriate for five-coordinated (deoxy) heme. PhD thesis. Davis: University of California
  • Gohlke H, Case DA. (2004). Converging free energy estimates: MM-PB(GB)SA studies on the protein–protein complex Ras-Raf. J Comput Chem 25:238–50
  • Hou T, Wang J, Li Y, Wang W. (2011). Assessing the performance of the MM/PBSA and MM/GBSA methods: 1. The accuracy of binding free energy calculations based on molecular dynamics simulations. J Chem Inform Model 51:69–82
  • Johnson MS, Overington J. (1993). A structural basis for sequence comparisons: an evaluation of scoring methodologies. J Mol Biol 233:716–38
  • Juvonen RO, Gynther J, Pasanen M, et al. (2000). Pronounced differences in inhibition potency of lactone and non-lactone compounds for mouse and human coumarin 7-hydroxylases (CYP2A5 and CYP2A6). Xenobiotica 30:81–92
  • Kaipainen P, Koivusaari U, Lang M. (1985). Catalytic and immunological comparison of coumarin 7-hydroxylation in different species. Comp Biochem Physiol Part C, Comp 81:293–6
  • Kirchmair J, Williamson MJ, Tyzack JD, et al. (2012). Computational prediction of metabolism: sites, products, SAR, P450 enzyme dynamics, and mechanisms. J Chem Inform Model 52:617–48
  • Korb O, Stützle T, Exner TE. (2009). Empirical scoring functions for advanced protein–ligand docking with plants. J Chem Inform Model 49:84–96
  • Lake BG, Gray TJB, Evans JG, et al. (1989). Studies on the mechanism of coumarin-induced toxicity in rat hepatocytes: comparison with dihydrocoumarin and other coumarin metabolites. Toxicol Appl Pharmacol 97:311–23
  • Lang MA, Gielen JE, Nebert DW. (1981). Genetic evidence for many unique liver microsomal P-450-mediated monooxygenase activities in heterogeneic stock mice. J Biol Chem 256:12068–75
  • Lehtonen JV, Still DJ, Rantanen VV, et al. (2004). BODIL: a molecular modeling environment for structure-function analysis and drug design. J Comput Aided Mol Des 18:401–19
  • Long A. (2013). Drug metabolism in silico – the knowledge-based expert system approach. Historical perspectives and current strategies. Drug Discov Today: Technol 10:e147–53
  • Makaji E, Trambitas CS, Shen P, et al. (2009). Effects of cytochrome P450 inhibitors on the biotransformation of fluorogenic substrates by adult male rat liver microsomes and cDNA-expressed rat cytochrome P450 isoforms. Toxicol Sci 113:293–304
  • Miller III BR, McGee TD, Swails JM, et al. (2012). MMPBSA.py: an efficient program for end-state free energy calculations. J Chem Theory Comput 8:3314–21
  • Morreel K, Kim H, Lu F, et al. (2010). Mass spectrometry-based fragmentation as an identification tool in lignomics. Anal Chem 89:8095–105
  • Niinivehmas SP, Virtanen SI, Lehtonen JV, et al. (2011). Comparison of virtual high-throughput screening methods for the identification of phosphodiesterase-5 inhibitors. J Chem Inform Model 51:1353–63
  • Onufriev A, Bashford D, Case DA. (2004). Exploring protein native states and large-scale conformational changes with a modified generalized born model. Proteins 55:383–94
  • Pelkonen O, Rautio A, Raunio H, Pasanen M. (2000). CYP2A6: a human coumarin 7-hydroxylase. Toxicology 144:139–47
  • Phillips JC, Braun R, Wang W, et al. (2005). Scalable molecular dynamics with NAMD. J Comp Chem 26:1781–802
  • Rahnasto M, Raunio H, Poso A, Juvonen RO. (2003). More potent inhibition of human CYP2A6 than mouse CYP2A5 enzyme activities by derivatives of phenylethylamine and benzaldehyde. Xenobiotica 33:529–39
  • Rahnasto M, Raunio H, Poso A, et al. (2005). Quantitative structure–activity relationship analysis of inhibitors of the nicotine metabolizing CYP2A6 enzyme. J Med Chem 48:440–9
  • Rahnasto MK, Raunio HA, Wittekindt C, et al. (2011). Identification of novel CYP2A6 inhibitors by virtual screening. Bioorg Med Chem 19:7186–93
  • Raner GM, Chiang EW, Vaz ADN, Coon MJ. (1997). Mechanism-based inactivation of cytochrome P450 2B4 by aldehydes: relationship to aldehyde deformylation via a peroxyhemiacetal intermediate. Biochemistry 36:4895–902
  • Rastelli G, Del Rio A, Degliesposti G, Sgobba M. (2010). Fast and accurate predictions of binding free energies using MM-PBSA and MM-GBSA. J Comput Chem 31:797–810
  • Raunio H, Juvonen R, Pasanen M, et al. (1998). Cytochrome P4502A6 (CYP2A6) expression in human hepatocellular carcinoma. Hepatology 27:427–32
  • Raunio H, Rahnasto-Rilla M. (2012). CYP2A6: genetics, structure, regulation, and function. Drug Metab Drug Interact 27:73–88
  • Roe DR, Cheatham TE. (2013). PTRAJ and CPPTRAJ: software for processing and analysis of molecular dynamics trajectory data. J Chem Theory Comput 9:3084–95
  • Sali A, Blundell TL. (1993). Comparative protein modelling by satisfaction of spatial restraints. J Mol Biol 234:779–815
  • Sevior DK, Pelkonen O, Ahokas JT. (2012). Hepatocytes: the powerhouse of biotransformation. Int J Biochem Cell Biol 44:257–61
  • Skaanild MT. (2006). Porcine cytochrome P450 and metabolism. Curr Pharm Design 12:1421–7
  • Soucek P. (1999). Expression of cytochrome P450 2A6 in Escherichia coli: purification, spectral and catalytic characterization, and preparation of polyclonal antibodies. Arch Biochem Biophys 370:190–200
  • Stepan AF, Walker DP, Bauman J, et al. (2011). Structural alert/reactive metabolite concept as applied in medicinal chemistry to mitigate the risk of idiosyncratic drug toxicity: a perspective based on the critical examination of trends in the top 200 drugs marketed in the United States. Chem Res Toxicol 24:1345–410
  • Tani N, Juvonen RO, Raunio H, et al. (2014). Rational design of novel CYP2A6 inhibitors. Bioorg Med Chem 22:6655–64
  • Testa B, Pedretti A, Vistoli G. (2012). Reactions and enzymes in the metabolism of drugs and other xenobiotics. Drug Discov Today 17:549–60
  • Timonen J, Romppanen R, Aulaskari P, Jänis J. (2013). Low-energy collision-induced dissociation tandem mass spectrometry of 7-acetonyloxycoumarins. Rapid Commun Mass Spectrom 27:2665–75
  • Tsui V, Case DA. (2000). Theory and applications of the Generalized Born solvation model in macromolecular simulations. Biopolymers 56:275–91
  • Turpeinen M, Korhonen LE, Tolonen A, et al. (2006). Cytochrome P450 (CYP) inhibition screening: comparison of three tests. Eur J Pharm Sci 29:130–8
  • Wang JM, Wang W, Kollman PA. (2001). Antechamber: an accessory software package for molecular mechanical calculations. Abstracts of papers of the American Chemical Society 222:U403
  • Word JM, Lovell SC, Richardson JS, Richardson DC. (1999). Asparagine and glutamine: using hydrogen atom contacts in the choice of side-chain amide orientation. J Mol Biol 285:1735–47
  • Yano JK, Denton TT, Cerny MA, et al. (2006). Synthetic inhibitors of cytochrome P-450 2A6: inhibitory activity, difference spectra, mechanism of inhibition, and protein cocrystallization. J Med Chem 49:6987–7001
  • Yano JK, Hsu MH, Griffin KJ, et al. (2005). Structures of human microsomal cytochrome P450 2A6 complexed with coumarin and methoxsalen. Nat Struct Mol Biol 12:822–3
  • Ylilauri M, Pentikäinen OT. (2013). MMGBSA as a tool to understand the binding affinities of filamin–peptide interactions. J Chem Inform Model 53:2626–33
  • Ylilauri M, Pentikäinen OT. (2012). Structural mechanism of N-methyl-D-aspartate receptor type 1 partial agonism. PLoS One 7:e47604
  • Zanger UM, Schwab M. (2013). Cytochrome P450 enzymes in drug metabolism: regulation of gene expression, enzyme activities, and impact of genetic variation. Pharmacol Ther 138:103–41

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.