Metabolism of N-substituted 7-methoxy-4-(aminomethyl) -coumarins by cytochrome P450 2D6 mutants and the indication of additional substrate interaction points

References

• De Graaf C, Oostenbrink C, Keizers PHJ, Van der Wijst T, Jongejan A, Vermeulen NPE. Catalytic site prediction and virtual screening of cytochrome P450 2D6 substrates by consideration of water and rescoring in automated docking. Journal of Medical Chemistry 2006; 49: 2417–2430
   PubMed Web of Science ®Google Scholar
• De Graaf C, Pospisil P, Pos W, Folkers G, Vermeulen NPE. Binding mode prediction of cytochrome P450 and thymidine kinase protein–ligand complexes by consideration of water and rescoring in automated docking. Journal of Medical Chemistry 2005; 7: 2308–2318
   Google Scholar
• De Groot MJ, Bijloo GJ, Martens BJ, Van Acker FA, Vermeulen NP. A refined substrate model for human cytochrome P450 2D6. Chemical Research in Toxicology 1997; 10: 41–48
   PubMed Web of Science ®Google Scholar
• Flanagan JU, Marechal JD, Ward R, Kemp CA, McLaughlin LA, Sutcliffe MJ, Roberts GC, Paine MJ, Wolf CR. Phe120 contributes to the regiospecificity of cytochrome P450 2D6: Mutation leads to the formation of a novel dextromethorphan metabolite. Biochemistry Journal 2004; 380: 353–360
   PubMed Web of Science ®Google Scholar
• Gotoh O. Substrate recognition sites in cytochrome P450 family 2 (CYP2) proteins inferred from comparative analyses of amino acid and coding nucleotide sequences. Journal of Biology and Chemistry 1992; 267: 83–90
   PubMed Web of Science ®Google Scholar
• Guengerich FP, Hanna IH, Martin MV, Gillam EM. Role of glutamic acid 216 in cytochrome P450 2D6 substrate binding and catalysis. Biochemistry 2003; 42: 1245–1253
   PubMed Web of Science ®Google Scholar
• Keizers PHJ, De Graaf C, De Kanter FJJ, Oostenbrink C, Feenstra KA, Commandeur JNM, Vermeulen NPE. Metabolic regio- and stereoselectivity of cytochrome P450 2D6 towards 3,4-methylenedioxy-N-alkyl-amphetamines: In silico predictions and experimental validation. Journal of Medical Chemistry 2005; 48: 6117–6127
   PubMed Web of Science ®Google Scholar
• Keizers PHJ, Lussenburg BMA, De Graaf C, Mentink LM, Vermeulen NPE, Commandeur JNM. Influence of phenylalanine 120 on cytochrome P450 2D6 catalytic selectivity and regiospecificity: Crucial role in 7-methoxy-4-(aminomethyl)-coumarin metabolism. Biochemistry and Pharmacology 2004; 68: 2263–2271
   PubMed Web of Science ®Google Scholar
• Kemp CA, Flanagan JU, Van Eldik AJ, Marechal JD, Wolf CR, Roberts GC, Paine MJ, Sutcliffe MJ. Validation of model of cytochrome P450 2D6: An in silico tool for predicting metabolism and inhibition. Journal of Medical Chemistry 2004; 47: 5340–5346
   PubMed Web of Science ®Google Scholar
• Lussenburg BMA, Keizers PHJ, De Graaf C, Hidestrand M, Ingelman-Sundberg M, Vermeulen NPE, Commandeur JNM. The role of phenylalanine 483 in cytochrome P450 2D6 is strongly substrate dependent. Biochemistry and Pharmacology 2005; 70: 1253–1261
   PubMed Web of Science ®Google Scholar
• Omura T, Sato R. The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature. Journal of Biology and Chemistry 1964; 239: 2370–2378
   PubMed Web of Science ®Google Scholar
• Onderwater RC, Venhorst J, Commandeur JNM, Vermeulen NPE. Design, synthesis, and characterization of 7-methoxy-4-(aminomethyl)coumarin as a novel and selective cytochrome P450 2D6 substrate suitable for high-throughput screening. Chemical Research in Toxicology 1999; 12: 555–559
   PubMed Web of Science ®Google Scholar
• Paine MJ, McLaughlin LA, Flanagan JU, Kemp CA, Sutcliffe MJ, Roberts GC, Wolf CR. Residues glutamate 216 and aspartate 301 are key determinants of substrate specificity and product regioselectivity in cytochrome P450 2D6. Journal of Biology and Chemistry 2003; 278: 4021–4027
   PubMed Web of Science ®Google Scholar
• Rowland P, Blaney FE, Smyth MG, Jones JJ, Leydon VR, Oxbrow AK, Lewis CJ, Tennant MG, Modi S, Eggleston DS, Chenery RJ, Bridges AM. Crystal structure of human cytochrome P450 2D6. Journal of Biology and Chemistry. Journal of Biology and Chemistry 2006; 281: 7614–7622
   PubMed Web of Science ®Google Scholar
• Vaz RJ, Nayeem A, Santone K, Chandrasena G, Gavai AV. A 3D-QSAR model for CYP2D6 inhibition in the aryloxypropanolamine series. Bioorganic Medicine and Chemistry Letters 2005; 15: 3816–3820
   PubMed Web of Science ®Google Scholar
• Venhorst J, Onderwater RC, Meerman JH, Commandeur JNM, Vermeulen NPE. Influence of N-substitution of 7-methoxy-4-(aminomethyl)-coumarin on cytochrome P450 metabolism and selectivity. Drug Metabolism and Disposition 2000; 28: 1524–1532
   PubMed Web of Science ®Google Scholar
• Venhorst J, Ter Laak AM, Commandeur JNM, Funae Y, Hiroi T, Vermeulen NPE. Homology modeling of rat and human cytochrome P450 2D (CYP2D) isoforms and computational rationalization of experimental ligand-binding specificities. Journal of Medical Chemistry 2003; 46: 74–86
   PubMed Web of Science ®Google Scholar
• Verdonk ML, Cole JC, Hartshorn MJ, Murray CW, Taylor RD. Improved protein–ligand docking using Gold. Proteins 2003; 52: 609–623
   PubMed Web of Science ®Google Scholar
• Vermeulen NPE. Prediction of drug metabolism: The case of cytochrome P450 2D6. Current Topics in Medical Chemistry 2003; 3: 1227–1239
   PubMed Web of Science ®Google Scholar
• Wang RX, Liu L, Lai LH, Tang YQ. SCORE: A new empirical method for estimating the binding affinity of a protein–ligand complex. Journal of Molecular Modeling 1998; 4: 379–394
   Web of Science ®Google Scholar
• Zanger UM, Raimundo S, Eichelbaum M. Cytochrome P450 2D6: Overview and update on pharmacology, genetics, biochemistry. Naunyn Schmiedeberg's Archives of Pharmacology 2004; 369: 23–37
   PubMed Web of Science ®Google Scholar