Binding of bufuralol, dextromethorphan, and 3,4-methylenedioxymethylamphetamine to wild-type and F120A mutant cytochrome P450 2D6 studied by resonance Raman spectroscopy

Biochemical and Biophysical Research Communications

Volumn 343, Issue 3, 2006, Pages 772-779

  Bonifacio, Alois ^a   Keizers, Peter H J ^a   Commandeur, Jan N M ^a   Vermeulen, Nico P E ^a   Robert, Bruno ^b   Gooijer, Cees ^a   van der Zwan, Gert ^a  

^a VU UNIVERSITY AMSTERDAM   (Netherlands)

^b CEA SACLAY   (France)

Author keywords

Bufuralol; CYP2D6; Cytochrome P450 2D6; Dextromethorphan; MDMA; Resonance Raman; Substrate mobility

Indexed keywords

3,4 METHYLENEDIOXYMETHAMPHETAMINE; 3,4 METHYLENEDIOXYMETHYLAMPHETAMINE; AMPHETAMINE DERIVATIVE; BUFURALOL; CYTOCHROME P450 2D6; DEXTROMETHORPHAN; UNCLASSIFIED DRUG;

ARTICLE; BINDING SITE; NONHUMAN; PRIORITY JOURNAL; RAMAN SPECTROMETRY; SPECTROSCOPY; WILD TYPE;

AMINO ACID SUBSTITUTION; BINDING SITES; CYTOCHROME P-450 CYP2D6; DEXTROMETHORPHAN; ETHANOLAMINES; HEME; HUMANS; MUTATION; N-METHYL-3,4-METHYLENEDIOXYAMPHETAMINE; SPECTRUM ANALYSIS, RAMAN;

EID: 33645936665     PISSN: 0006291X     EISSN: 10902104     Source Type: Journal    
DOI: 10.1016/j.bbrc.2006.03.027     Document Type: Article

References (39)

1. Guengerich F.P. Cytochrome p450: what have we learned and what are the future issues?. Drug. Metab. Rev. 36 (2004) 159-197
2. Bertilsson L., Dahl M.L., Dalen P., and Al-Shurbaji A. Molecular genetics of CYP2D6: clinical relevance with focus on psychotropic drugs. Br. J. Clin. Pharmacol. 53 (2002) 111-122
3. Zanger U.M., Raimundo S., and Eichelbaum M. Cytochrome P450 2D6: overview and update on pharmacology, genetics, biochemistry. Naunyn-Schmiedeberg's Arch. Pharmacol. 369 (2004) 23-37
4. Ingelman-Sundberg M. Pharmacogenetics of cytochrome P450 and its application in drug therapy: the past, present and future. Trends Pharmacol. Sci. 25 (2004) 193-200
5. Keizers P.H.J., Lussenburg B.M.A., de Graaf C., Mentink L.M., Vermeulen N.P.E., and Commandeur J.N.M. Influence of phenylalanine 120 on cytochrome P450 2D6 catalytic selectivity and regiospecificity: crucial role in 7-methoxy-4-(aminomethyl)-coumarin metabolism. Biochem. Pharmacol. 68 (2004) 2263-2271
6. Flanagan J.U., Marechal J.D., Ward R., Kemp C.A., Mclaughlin L.A., Sutcliffe M.J., Roberts G.C.K., Paine M.J.I., and Wolf C.R. Phe(120) contributes to the regiospecificity of cytochrome P450 2D6: mutation leads to the formation of a novel dextromethorphan metabolite. Biochem. J. 380 (2004) 353-360
7. Paine M.J.I., McLaughlin L.A., Flanagan J.U., Kemp C.A., Sutcliffe M.J., Roberts G.C.K., and Wolf C.R. Residues glutamate 216 and aspartate 301 are key determinants of substrate specificity and product regioselectivity in cytochrome p450 2D6. J. Biol. Chem. 278 (2003) 4021-4027
8. Masuda K., Tamagake K., Okuda Y., Torigoe F., Tsuzuki D., Isobe T., Hichiya H., Hanioka N., Yamamoto S., and Narimatsu S. Change in enantioselectivity in bufuralol 1″-hydroxylation by the substitution of phenylalanine-120 by alanine in cytochrome P450 2D6. Chirality 17 (2005) 37-43
9. Guengerich F.P., Hanna I.H., Martin M.V., and Gillam E.M.J. Role of glutamic acid 216 in cytochrome P450 2D6 substrate binding and catalysis. Biochemistry 42 (2003) 1245-1253
10. Ohta T., Matsuura K., Yoshizawa K., and Morishima I. The electronic and vibrational structures of iron-oxo porphyrin with a methoxide or cysteinate axial ligand. J. Inorg. Biochem. 82 (2000) 141-152
11. Hayhurst G.P., Harlow J., Chowdry J., Gross E., Hilton E., Lennard M.S., Tucker G.T., and Ellis S.W. Influence of phenylalanine-481 substitutions on the catalytic activity of cytochrome P450 2D6. Biochem. J. 355 (2001) 373-379
12. Guengerich F.P., Miller G.P., Hanna I.H., Martin M.V., Leger S., Black C., Chauret N., Silva J.M., Trimble L.A., Yergey J.A., and Nicoll-Griffith D.A. Diversity in the oxidation of substrates by cytochrome P450 2D6: lack of an obligatory role of aspartate 301-substrate electrostatic bonding. Biochemistry 41 (2002) 11025-11034
13. Hanna I.H., Krauser J.A., Cai H.L., Kim M.S., and Guengerich F.P. Diversity in mechanisms of substrate oxidation by cytochrome P450 2D6-lack of an allosteric role of NADPH-cytochrome P450 reductase in catalytic regioselectivity. J. Biol. Chem. 276 (2001) 39553-39561
14. Kirton S.B., Kemp C.A., Tomkinson N.P., St-Gallay S., and Sutcliffe M.J. Impact of incorporating the 2C5 crystal structure into comparative models of cytochrome P450 2D6. Proteins 49 (2002) 216-231
15. Venhorst J., ter Laak A.M., Commandeur J.N.M., Funae Y., Hiroi T., and Vermeulen N.P.E. Homology modeling of rat and human cytochrome P450 2D (CYP2D) isoforms and computational rationalization of experimental ligand-binding specificities. J. Med. Chem. 46 (2003) 74-86
16. Keizers P.H.J., de Graaf C., de Kanter F.J.J., Oostenbrink C., Feenstra K.A., Commandeur J.N.M., and Vermeulen N.P.E. Metabolic regio- and stereoselectivity of cytochrome P450 2D6 towards 3,4-methylenedioxy-N-alkylamphetamines: in silico predictions and experimental validation. J. Med. Chem. 48 (2005) 6117-6127
17. Rowland P., Blaney F.E., Smyth M.G., Jones J.J., Leydon V.R., Oxbrow A.K., Lewis C.J., Tennant M.G., Modi S., Eggelston D.S., Chenery R.J., and Bridges A.M. Crystal structure of human cytochrome P450 2D6. J. Biol. Chem. 281 (2005) 7614-7622
18. Koymans L., Vermeulen N.P.E., Vanacker S.A.B.E., Tekoppele J.M., Heykants J.J.P., Lavrijsen K., Meuldermans W., and Denkelder G.M.D. A predictive model for substrates of cytochrome P450-debrisoquine (2d6). Chem. Res. Toxicol. 5 (1992) 211-219
19. Spiro T.G., and Li X. Resonance Raman spectroscopy of metalloporphyrins. In: Spiro T.G. (Ed). Biological Applications of Raman Spectrosocpy vol. 3 (1987), Wiley, New York 1-38
20. Hildebrandt P. Resonance Raman spectroscopy of cytochrome P450. In: Ruckpaul K., and Rein H. (Eds). Relationships Between Structure and Function of Cytochrome P-450: Experiments, Calculations, Models vol. 7 (1992), Akademie Verlag, Berlin 166-215
21. Braun U., Shulgin A.T., and Braun G. Centrally active N-substituted analogs of 3,4-methylenedioxyphenylisopropylamine (3,4-methylenedioxyamphetamine). J. Pharm. Sci. 69 (1980) 192-195
22. Onderwater R.C.A., Venhorst J., Commandeur J.N.M., and Vermeulen N.P.E. Design, synthesis, and characterization of 7-methoxy-4-(aminomethyl)coumarin as a novel and selective cytochrome P450 2D6 substrate suitable for high-throughput screening. Chem. Res. Toxicol. 12 (1999) 555-559
23. Omura T., and Sato R. Carbon monoxide-binding pigment of liver microsomes. 2. Solubilization purification+properties. J. Biol. Chem. 239 (1964) 2379
24. Jefcoate C.R. Measurement of substrate and inhibitor binding to microsomal cytochrome P-450 by optical-difference spectroscopy. Methods Enzymol. 52 (1978) 258-279
25. Deng T.J., Proniewicz L.M., Kincaid J.R., Yeom H., Macdonald I.D.G., and Sligar S.G. Resonance Raman studies of cytochrome P450BM3 and its complexes with exogenous ligands. Biochemistry 38 (1999) 13699-13706
26. Kalsbeck W.A., Ghosh A., Pandey R.K., Smith K.M., and Bocian D.F. Determinants of the vinyl stretching frequency in protoporphyrins-implications for cofactor-protein interactions in heme-proteins. J. Am. Chem. Soc. 117 (1995) 10959-10968
27. Hu S.Z., Smith K.M., and Spiro T.G. Assignment of protoheme resonance Raman spectrum by heme labeling in myoglobin. J. Am. Chem. Soc. 118 (1996) 12638-12646
28. Hildebrandt P., Heibel G., Anzenbacher P., Lange R., Kruger V., and Stier A. Conformational-analysis of mitochondrial and microsomal cytochrome-P-450 by resonance Raman-spectroscopy. Biochemistry 33 (1994) 12920-12929
29. Chen Z.C., Ost T.W.B., and Schelvis J.P.M. Phe393 mutants of cytochrome P450BM3 with modified heme redox potentials have altered heme vinyl and propionate conformations. Biochemistry 43 (2004) 1798-1808
30. Keizers P.H.J., Schraven L.H.M., de Graaf C., Hidestrand M., Ingelman-Sundberg M., van Dijk B.R., Vermeulen N.P.E., and Commandeur J.N.M. Role of the conserved threonine 309 in mechanism of oxidation by cytochrome P450 2D6. Biochem. Biophys. Res. Commun. 338 (2005) 1065-1074
31. Spiro T.G., and Wasbotten I.H. CO as a vibrational probe of heme protein active sites. J. Inorg. Biochem. 99 (2005) 34-44
32. Phillips G.N., Teodoro M.L., Li T.S., Smith B., and Olson J.S. Bound CO is a molecular probe of electrostatic potential in the distal pocket of myoglobin. J. Phys. Chem. B. 103 (1999) 8817-8829
33. Jung C., Schulze H., and Deprez E. Role of the polarity of the heme environment for the CO stretch modes in cytochrome P-450cam-CO. Biochemistry 35 (1996) 15088-15094
34. Matsunaga I., Yamada A., Lee D.S., Obayashi E., Fujiwara N., Kobayashi K., Ogura H., and Shiro Y. Enzymatic reaction of hydrogen peroxide-dependent peroxygenase cytochrome P450s: kinetic deuterium isotope effects and analyses by resonance Raman spectroscopy. Biochemistry 41 (2002) 1886-1892
35. Lewis D.F.V. Cytochrome P450: Structure, Function and Mechanism (1996), Taylor and Francis, London
36. Denisov I.G., Makris T.M., Sligar S.G., and Schlichting I. Structure and chemistry of cytochrome P450. Chem. Rev. 105 (2005) 2253-2277
37. Schulze H., Hoa G.H.B., and Jung C. Mobility of norbornane-type substrates and water accessibility in cytochrome P-450(cam). Biochim. Biophys. Acta 1338 (1997) 77-92
38. Hu S.Z., and Kincaid J.R. Resonance Raman-spectra of the nitric-oxide adducts of ferrous cytochrome P450cam in the presence of various substrates. J. Am. Chem. Soc. 113 (1991) 9760-9766
39. Raag R., and Poulos T.L. Crystal-structures of cytochrome-P-450cam complexed with camphane, thiocamphor, and adamantane-factors controlling P-450 substrate hydroxylation. Biochemistry 30 (1991) 2674-2684