Home LiteratureArticle Details
PMID: 17985934 Published · ppublish English Journal Article Research Support, N.I.H., Extramural Research Support, Non-U.S. Gov't

Magic-angle spinning solid-state NMR spectroscopy of nanodisc-embedded human CYP3A4.

Biochemistry ·Vol. 46 ·No. 48 ·2007-12-04 ·Pages 13696-703

Kijac AZ, Li Y, Sligar SG, Rienstra CM

Abstract

Cytochrome P450 (CYP) 3A4 contributes to the metabolism of approximately 50% of commercial drugs by oxidizing a large number of structurally diverse substrates. Like other endoplasmic reticulum-localized P450s, CYP3A4 contains a membrane-anchoring N-terminal helix and a significant number of hydrophobic domains, important for the interaction between CYP3A4 and the membrane. Although the membrane affects specificity of CYP3A4 ligand binding, the structural details of the interaction have not been revealed so far because X-ray crystallography studies are available only for the soluble domain of CYP3A4. Here we report sample preparation and initial magic-angle spinning (MAS) solid-state NMR (SSNMR) of CYP3A4 (Delta3-12) embedded in a nanoscale membrane bilayer, or Nanodisc. The growth protocol yields approximately 2.5 mg of the enzymatically active, uniformly 13C,15N-enriched CYP3A4 from 1 L of growth medium. Polyethylene glycol 3350-precipitated CYP3A4 in Nanodiscs yields spectra of high resolution and sensitivity, consistent with a folded, homogeneous protein. CYP3A4 in Nanodiscs remains enzymatically active throughout the precipitation protocol as monitored by bromocriptine binding. The 13C line widths measured from 13C-13C 2D chemical shift correlation spectra are approximately 0.5 ppm. The secondary structure distribution within several amino acid types determined from 13C chemical shifts is consistent with the ligand-free X-ray structures. These results demonstrate that MAS SSNMR can be performed on Nanodisc-embedded membrane proteins in a folded, active state. The combination of SSNMR and Nanodisc methodologies opens up new possibilities for obtaining structural information on CYP3A4 and other integral membrane proteins with full retention of functionality.

MeSH Terms
Crystallography, X-Ray Cytochrome P-450 CYP3A Cytochrome P-450 Enzyme System/chemistry Humans Nanostructures Nuclear Magnetic Resonance, Biomolecular Protein Conformation
Chemicals
Cytochrome P-450 Enzyme System Cytochrome P-450 CYP3A CYP3A4 protein, human
Authors & Affiliations
4 authors, click to expand affiliations / ORCID
Kijac Aleksandra Z
Center for Biophysics and Computational Biology, University of Illinois at Urbana-Champaign, Urbana, Illinois 618001, USA.
Li Ying
Sligar Stephen G
Rienstra Chad M
References (61)
61 references, click to expand
  1. On choosing a detergent for solution NMR studies of membrane proteins.
    J Biomol NMR. 1998 May;11(4):381-6 PMID: 9691283
  2. Solid-state magic-angle spinning NMR of outer-membrane protein G from Escherichia coli.
    Chembiochem. 2005 Sep;6(9):1679-84 PMID: 16138308
  3. Observation of ligand binding to cytochrome P450 BM-3 by means of solid-state NMR spectroscopy.
    J Am Chem Soc. 2005 Oct 12;127(40):13816-21 PMID: 16201802
  4. Over-production of proteins in Escherichia coli: mutant hosts that allow synthesis of some membrane proteins and globular proteins at high levels.
    J Mol Biol. 1996 Jul 19;260(3):289-98 PMID: 8757792
  5. Cooperativity in cytochrome P450 3A4: linkages in substrate binding, spin state, uncoupling, and product formation.
    J Biol Chem. 2007 Mar 9;282(10):7066-76 PMID: 17213193
  6. Ligand binding to cytochrome P450 3A4 in phospholipid bilayer nanodiscs: the effect of model membranes.
    J Biol Chem. 2007 Sep 28;282(39):28309-28320 PMID: 17573349
  7. Transducin activation by nanoscale lipid bilayers containing one and two rhodopsins.
    J Biol Chem. 2007 May 18;282(20):14875-81 PMID: 17395586
  8. Nanodiscs unravel the interaction between the SecYEG channel and its cytosolic partner SecA.
    EMBO J. 2007 Apr 18;26(8):1995-2004 PMID: 17396152
  9. Oxidation of nonionic detergents by cytochrome P450 enzymes.
    Arch Biochem Biophys. 1998 May 15;353(2):365-73 PMID: 9606971
  10. Applications of phospholipid bilayer nanodiscs in the study of membranes and membrane proteins.
    Biochemistry. 2007 Feb 27;46(8):2059-69 PMID: 17263563
  11. Mammalian microsomal cytochrome P450 monooxygenase: structural adaptations for membrane binding and functional diversity.
    Mol Cell. 2000 Jan;5(1):121-31 PMID: 10678174
  12. Chemical shift referencing in MAS solid state NMR.
    J Magn Reson. 2003 Jun;162(2):479-86 PMID: 12810033
  13. A malleable catalyst dominates the metabolism of drugs.
    Proc Natl Acad Sci U S A. 2006 Sep 12;103(37):13565-6 PMID: 16954196
  14. THE CARBON MONOXIDE-BINDING PIGMENT OF LIVER MICROSOMES. II. SOLUBILIZATION, PURIFICATION, AND PROPERTIES.
    J Biol Chem. 1964 Jul;239:2379-85 PMID: 14209972
  15. Phenylalanine and tryptophan scanning mutagenesis of CYP3A4 substrate recognition site residues and effect on substrate oxidation and cooperativity.
    Biochemistry. 2001 Aug 28;40(34):10150-60 PMID: 11513592
  16. Direct solubilization of heterologously expressed membrane proteins by incorporation into nanoscale lipid bilayers.
    Biotechniques. 2003 Sep;35(3):556-60, 562-3 PMID: 14513561
  17. RefDB: a database of uniformly referenced protein chemical shifts.
    J Biomol NMR. 2003 Mar;25(3):173-95 PMID: 12652131
  18. Crystal structures of human cytochrome P450 3A4 bound to metyrapone and progesterone.
    Science. 2004 Jul 30;305(5684):683-6 PMID: 15256616
  19. Protein structure determination by high-resolution solid-state NMR spectroscopy: application to microcrystalline ubiquitin.
    J Am Chem Soc. 2005 Jun 22;127(24):8618-26 PMID: 15954766
  20. Phospholipid phase transitions in homogeneous nanometer scale bilayer discs.
    FEBS Lett. 2004 Jan 2;556(1-3):260-4 PMID: 14706860
  21. Testosterone, 7-benzyloxyquinoline, and 7-benzyloxy-4-trifluoromethyl-coumarin bind to different domains within the active site of cytochrome P450 3A4.
    Drug Metab Dispos. 2001 Nov;29(11):1473-9 PMID: 11602524
  22. Expression of modified human cytochrome P450 3A4 in Escherichia coli and purification and reconstitution of the enzyme.
    Arch Biochem Biophys. 1993 Aug 15;305(1):123-31 PMID: 8342945
  23. Cytochrome P-450 3A4: regulation and role in drug metabolism.
    Annu Rev Pharmacol Toxicol. 1999;39:1-17 PMID: 10331074
  24. Human cytochrome P450 enzymes expressed in bacteria: reagents to probe molecular interactions in toxicology.
    Clin Exp Pharmacol Physiol. 1998 Nov;25(11):877-86 PMID: 9807658
  25. DSSPcont: Continuous secondary structure assignments for proteins.
    Nucleic Acids Res. 2003 Jul 1;31(13):3293-5 PMID: 12824310
  26. Cytochrome P4503A (CYP3A) metabolism: prediction of in vivo activity in humans.
    J Pharmacokinet Biopharm. 1996 Oct;24(5):475-90 PMID: 9131486
  27. Structural analysis of nanoscale self-assembled discoidal lipid bilayers by solid-state NMR spectroscopy.
    Biophys J. 2006 Nov 15;91(10):3819-28 PMID: 16905610
  28. Analyzing binding of N-terminal truncated, microsomal cytochrome P450s to membranes.
    Methods Enzymol. 2002;357:116-20 PMID: 12424903
  29. Characterization of stable human aromatase expressed in E. coli.
    Steroids. 2004 Apr;69(4):235-43 PMID: 15183689
  30. High-yield expression and purification of isotopically labeled cytochrome P450 monooxygenases for solid-state NMR spectroscopy.
    Biochim Biophys Acta. 2007 Dec;1768(12):3061-70 PMID: 18005930
  31. Heteronuclear 2D-correlations in a uniformly [13C, 15N] labeled membrane-protein complex at ultra-high magnetic fields.
    J Biomol NMR. 2001 Mar;19(3):243-53 PMID: 11330811
  32. NMRPipe: a multidimensional spectral processing system based on UNIX pipes.
    J Biomol NMR. 1995 Nov;6(3):277-93 PMID: 8520220
  33. Structural and dynamic studies of proteins by solid-state NMR spectroscopy: rapid movement forward.
    Curr Opin Struct Biol. 2004 Oct;14(5):554-61 PMID: 15465315
  34. The local phospholipid environment modulates the activation of blood clotting.
    J Biol Chem. 2007 Mar 2;282(9):6556-63 PMID: 17200119
  35. Structure of a protein determined by solid-state magic-angle-spinning NMR spectroscopy.
    Nature. 2002 Nov 7;420(6911):98-102 PMID: 12422222
  36. C alpha and C beta carbon-13 chemical shifts in proteins from an empirical database.
    J Biomol NMR. 1999 Mar;13(3):199-211 PMID: 10212983
  37. Atypical kinetic profiles in drug metabolism reactions.
    Drug Metab Dispos. 2002 Apr;30(4):355-62 PMID: 11901086
  38. Conformational heterogeneity of cytochrome P450 3A4 revealed by high pressure spectroscopy.
    Biochem Biophys Res Commun. 2003 Dec 5;312(1):121-30 PMID: 14630029
  39. Directed self-assembly of monodisperse phospholipid bilayer Nanodiscs with controlled size.
    J Am Chem Soc. 2004 Mar 24;126(11):3477-87 PMID: 15025475
  40. Secondary structure, dynamics, and topology of a seven-helix receptor in native membranes, studied by solid-state NMR spectroscopy.
    Angew Chem Int Ed Engl. 2007;46(3):459-62 PMID: 17001715
  41. Co-incorporation of heterologously expressed Arabidopsis cytochrome P450 and P450 reductase into soluble nanoscale lipid bilayers.
    Arch Biochem Biophys. 2004 Apr 15;424(2):141-53 PMID: 15047186
  42. Thermotropic phase transition in soluble nanoscale lipid bilayers.
    J Phys Chem B. 2005 Aug 18;109(32):15580-8 PMID: 16852976
  43. Kinetics of dithionite-dependent reduction of cytochrome P450 3A4: heterogeneity of the enzyme caused by its oligomerization.
    Biochemistry. 2005 Oct 25;44(42):13902-13 PMID: 16229479
  44. Structural basis for ligand promiscuity in cytochrome P450 3A4.
    Proc Natl Acad Sci U S A. 2006 Sep 12;103(37):13682-7 PMID: 16954191
  45. Magic-angle spinning solid-state NMR spectroscopy of the beta1 immunoglobulin binding domain of protein G (GB1): 15N and 13C chemical shift assignments and conformational analysis.
    J Am Chem Soc. 2005 Sep 7;127(35):12291-305 PMID: 16131207
  46. Rapid and accurate calculation of protein 1H, 13C and 15N chemical shifts.
    J Biomol NMR. 2003 Jul;26(3):215-40 PMID: 12766419
  47. Partial (13)C and (15)N chemical-shift assignments of the disulfide-bond-forming enzyme DsbB by 3D magic-angle spinning NMR spectroscopy.
    Chembiochem. 2007 Mar 5;8(4):434-42 PMID: 17285659
  48. The membrane protein universe: what's out there and why bother?
    J Intern Med. 2007 Jun;261(6):543-57 PMID: 17547710
  49. The structure of human microsomal cytochrome P450 3A4 determined by X-ray crystallography to 2.05-A resolution.
    J Biol Chem. 2004 Sep 10;279(37):38091-4 PMID: 15258162
  50. Structure of the Rhodobacter sphaeroides light-harvesting 1 beta subunit in detergent micelles.
    Biochemistry. 2002 Jan 8;41(1):31-41 PMID: 11772000
  51. Structural diversity of human xenobiotic-metabolizing cytochrome P450 monooxygenases.
    Biochem Biophys Res Commun. 2005 Dec 9;338(1):331-6 PMID: 16157296
  52. Homotropic cooperativity of monomeric cytochrome P450 3A4 in a nanoscale native bilayer environment.
    Arch Biochem Biophys. 2004 Oct 15;430(2):218-28 PMID: 15369821
  53. Identification of the residues in the helix F/G loop important to catalytic function of membrane-bound prostacyclin synthase.
    Biochemistry. 2003 May 20;42(19):5609-17 PMID: 12741817
  54. A concept for rapid protein-structure determination by solid-state NMR spectroscopy.
    Angew Chem Int Ed Engl. 2005 Mar 29;44(14):2089-92 PMID: 15744789
  55. Drug discovery: a historical perspective.
    Science. 2000 Mar 17;287(5460):1960-4 PMID: 10720314
  56. The cytochromes P450 and b5 and their reductases--promising targets for structural studies by advanced solid-state NMR spectroscopy.
    Biochim Biophys Acta. 2007 Dec;1768(12):3235-59 PMID: 17945183
  57. Membrane properties induced by anionic phospholipids and phosphatidylethanolamine are critical for the membrane binding and catalytic activity of human cytochrome P450 3A4.
    Biochemistry. 2003 Dec 30;42(51):15377-87 PMID: 14690448
  58. The ferrous-dioxygen intermediate in human cytochrome P450 3A4. Substrate dependence of formation and decay kinetics.
    J Biol Chem. 2006 Aug 18;281(33):23313-8 PMID: 16762915
  59. A method for efficient isotopic labeling of recombinant proteins.
    J Biomol NMR. 2001 May;20(1):71-5 PMID: 11430757
  60. Clinical importance of non-genetic and genetic cytochrome P450 function tests in liver disease.
    J Clin Pharm Ther. 1998 Jun;23(3):161-70 PMID: 9831966
  61. Residual backbone and side-chain 13C and 15N resonance assignments of the intrinsic transmembrane light-harvesting 2 protein complex by solid-state Magic Angle Spinning NMR spectroscopy.
    J Biomol NMR. 2005 Apr;31(4):279-93 PMID: 15928995
Article Info
Journal
Biochemistry
Abbr.
Biochemistry
ISSN
0006-2960
Published
2007-12-04
Epub
2007-00-07
Pages
13696-703
Language
English
Region
United States
NLM ID
0370623
PMCID
PMC2571072
Subset
IM
Grants
NIGMS NIH HHS · GM33775 · United States
NIGMS NIH HHS · GM79530 · United States
NIGMS NIH HHS · GM31756 · United States
NIGMS NIH HHS · R37 GM031756 · United States
NIGMS NIH HHS · R01 GM079530-01A1 · United States
NIGMS NIH HHS · R01 GM033775 · United States
NIGMS NIH HHS · R01 GM031756 · United States
NIGMS NIH HHS · R01 GM079530 · United States
Analysis Services
Analysis Services

Contact

No. 2 Wenbo Road, Zhangqiu District, Jinan, Shandong

Qilu Normal University · Genelibs Bioinformatics Lab

750 Shunhua Rd, Jinan

2F, Bldg F, University Science Park

Tel: 0531-88819269

WeChat Official Account

Follow our WeChat subscription account for real-time updates and the latest in medical and biological research.


Business Email

E-mail: product@genelibs.com