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Xenobiotica
the fate of foreign compounds in biological systems
Volume 49, 2019 - Issue 9
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General Xenobiochemistry

Development of new Coumarin-based profluorescent substrates for human cytochrome P450 enzymes

, , , & ORCID Icon
Pages 1015-1024 | Received 10 Aug 2018, Accepted 26 Sep 2018, Published online: 29 Nov 2018

References

  • Berman HM, Westbrook J, Feng Z, et al. (2000). The protein data bank. Nucleic Acids Res 28:235–42.
  • Cali JJ, Ma D, Sobol M, et al. (2006). Luminogenic cytochrome P450 assays. Expert Opin Drug Metab Toxicol 2:629–45.
  • Chauret N, Dobbs B, Lackman RL, et al. (2001). The use of 3-[2-(N,N-diethyl-N-methylammonium)ethyl]-7-methoxy-4-methylcoumarin (AMMC) as a specific CYP2D6 probe in human liver microsomes. Drug Metab Dispos 29:1196–200.
  • Crespi CL, Miller VP, Penman BW. (1997). Microtiter plate assays for inhibition of human, drug-metabolizing cytochromes P450. Anal Biochem 248:188–90.
  • Crespi CL, Miller VP, Stresser DM. (2002). Design and application of fluorometric assays for human cytochrome P450 inhibition. Meth Enzymol 357:276–84.
  • Crespi CL, Stresser DM. (2000). Fluorometric screening for metabolism-based drug-drug interactions. J Pharmacol Toxicol Methods 44:325–31.
  • Delogu GL, Serra S, Quezada E, et al. (2014). Monoamine oxidase (MAO) inhibitory activity: 3-phenylcoumarins versus 4-hydroxy-3-phenylcoumarins. Chem Med 9:1672–6.
  • Fowler S, Morcos PN, Cleary Y, et al. (2017). Progress in prediction and interpretation of clinically relevant metabolic drug-drug interactions: a minireview illustrating recent developments and current opportunities. Curr Pharmacol Rep 3:36–49.
  • Ghosal A, Hapangama N, Yuan Y, et al. (2003). Rapid determination of enzyme activities of recombinant human cytochromes P450, human liver microsomes and hepatocytes. Biopharm Drug Dispos 24:375–84.
  • Gonzalez FJ, Coughtrie M, Tukey RH. (2018). Drug metabolism. In: Brunton L.L., Chabner B.A., and Knollmann B.C., eds. Goodman & Gilman’s the pharmacological basis of therapeutics. New York: McGraw-Hill, 85–100.
  • Guengerich FP. (2017). Intersection of the roles of cytochrome P450 enzymes with xenobiotic and endogenous substrates: relevance to toxicity and drug interactions. Chem Res Toxicol 30:2–12.
  • Humphrey W, Dalke A, Schulten K. (1996). VMD: visual molecular dynamics. J Mol Graph 14:33–8.
  • Johnson MS, Overington JP. (1993). A structural basis for sequence comparisons. An evaluation of scoring methodologies. J Mol Biol 233:716–38.
  • Juvonen RO, Kuusisto M, Fohrgrup C, et al. (2016). Inhibitory effects and oxidation of 6-methylcoumarin, 7-methylcoumarin and 7-formylcoumarin via human CYP2A6 and its mouse and pig orthologous enzymes. Xenobiotica 46:14–24.
  • Juvonen RO, Rauhamäki S, Kortet S, et al. (2018). Molecular docking-based design and development of a highly selective probe substrate for UDP-glucuronosyltransferase 1A10. Mol Pharm 15:923–33.
  • Kirchmair J, Göller AH, Lang D, et al. (2015). Predicting drug metabolism: experiment and/or computation? Nat Rev Drug Discov 14:387–404.
  • Knights KM, Stresser DM, Miners JO, et al. (2016). In vitro drug metabolism using liver microsomes. Curr Protoc Pharmacol 2016:7.8.1–.24.
  • 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.
  • Lavis LD, Raines RT. (2014). Bright building blocks for chemical biology. ACS Chem Biol 9:855–66.
  • Lehtonen JV, Still D-J, Rantanen V-V, et al. (2004). BODIL: a molecular modeling environment for structure-function analysis and drug design. J Comput Aided Mol Des 18:401–19.
  • Mayer RT, Dolence EK, Mayer GE. (2007). A real-time fluorescence assay for measuring N-dealkylation. Drug Metab Dispos 35:103–9.
  • Niinivehmas SP, Manivannan E, Rauhamäki S, et al. (2016). Identification of estrogen receptor α ligands with virtual screening techniques. J Mol Graph Model 64:30–9.
  • Niinivehmas S, Postila PA, Rauhamäki S, et al. (2018). Blocking oestradiol synthesis pathways with potent and selective coumarin derivatives. J Enzyme Inhib Med Chem 33:743–54.
  • Niinivehmas SP, Salokas K, Lätti S, et al. (2015). Ultrafast protein structure-based virtual screening with Panther. J Comput Aided Mol Des 29:989–1006.
  • Pelkonen O, Turpeinen M, Hakkola J, et al. (2013). Preservation, induction or incorporation of metabolism into the in vitro cellular system - views to current opportunities and limitations. Toxicol In Vitro 27:1578–83.
  • Pelkonen O, Turpeinen M, Uusitalo J, et al. (2005). Prediction of drug metabolism and interactions on the basis of in vitro investigations. Basic Clin Pharmacol Toxicol 96:167–75.
  • Pelkonen O, Rautio A, Raunio H, et al. (2000). CYP2A6: a human coumarin 7-hydroxylase. Toxicology 144:139–47.
  • Rauhamäki S, Postila PA, Niinivehmas S, et al. (2018). Structure-activity relationship analysis of 3-phenylcoumarin-based monoamine oxidase B inhibitors. Front Chem 6:1–18.
  • Raunio H, Rahnasto-Rilla M. (2012). CYP2A6: genetics, structure, regulation, and function. Drug Metabol Drug Interact 27:73–88.
  • Rendic S. (2002). Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev 34:83–448.
  • Reynald RL, Sansen S, Stout CD, et al. (2012). Structural characterization of human cytochrome P450 2C19: active site differences between P450s 2C8, 2C9, and 2C19. J Biol Chem 287:44581–91.
  • Sansen S, Yano JK, Reynald RL, et al. (2007). Adaptations for the oxidation of polycyclic aromatic hydrocarbons exhibited by the structure of human P450 1A2. J Biol Chem 282:14348–55.
  • Sai Y, Dai R, Yang TJ, et al. (2000). Assessment of specificity of eight chemical inhibitors using cDNA-expressed cytochromes P450. Xenobiotica 30:327–43.
  • Sevior DK, Pelkonen O, Ahokas JT. (2012). Hepatocytes: the powerhouse of biotransformation. Int J Biochem Cell Biol 44:257–61.
  • Skaanild MT, Friis C. (2005). Porcine CYP2A polymorphisms and activity. Basic Clin Pharmacol Toxicol 97:115–21.
  • Testa B, Pedretti A, Vistoli G. (2012). Reactions and enzymes in the metabolism of drugs and other xenobiotics. Drug Discov Today 17:549–60.
  • The UniProt Consortium. (2017). UniProt: the universal protein knowledgebase. Nucleic Acids Res 45:D158–69.
  • Tolonen A, Pelkonen O. (2015). Analytical challenges for conducting rapid metabolism characterization for QIVIVE. Toxicology 332:20–9.
  • Trubetskoy OV, Gibson JR, Marks BD. (2005). Highly miniaturized formats for in vitro drug metabolism assays using vivid fluorescent substrates and recombinant human cytochrome P450 enzymes. J Biomol Screen 10:56–66.
  • 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.
  • Vainio MJ, Puranen JS, Johnson MS. (2009). ShaEP: molecular overlay based on shape and electrostatic potential ShaEP: molecular overlay based on shape and electrostatic potential. Methods 49:492–502.
  • Walsh AA, Szklarz GD, Scott EE. (2013). Human cytochrome P450 1A1 structure and utility in understanding drug and xenobiotic metabolism. J Biol Chem 288:12932–43.
  • Wang A, Savas U, Stout CD, Johnson EF.(2011). Structural characterization of the complex between alpha-naphthoflavone and human cytochrome P450 1B1. J Biol Chem 286:5736–43.
  • Wang A, Savas U, Hsu M-H, et al. (2012). Crystal structure of human cytochrome P450 2D6 with prinomastat bound. J Biol Chem 287:10834–43.
  • Waxman DJ, Chang TKH. (2006). Use of 7-ethoxycoumarin to monitor multiple enzymes in the Human CYP1, CYP2, and CYP3 families. In: Phillips I.R. and Shephard E.A., eds. Cytochrome P450 Protocols. Totowa (NJ0: Humana Press, 153–6.
  • Wheeler WC, Gladstein DS. (1994). MALIGN: a multiple sequence alignment program. J Hered 85:410–3.
  • 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.
  • 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.
  • Zientek MA, Youdim K. (2015). Reaction phenotyping: advances in the experimental strategies used to characterize the contribution of drug-metabolizing enzymes. Drug Metab Dispos 43:163–81.

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