Nanoelectrochemistry of cytochrome P450s: Direct electron transfer and electrocatalysis

Direct electron transfer has been demonstrated between cytochrome P450 2B4 (CYP2B4), P450 1A2 (CYP1A2), sterol 14α-demethylase (CYP51MT) and screen printed graphite electrodes, modified by gold nanoparticles and didodecyldimethyl ammonium bromide (DDAB). The proposed method for preparation of enzymatic nanostructured electrodes may be used for electrodetection of this hemoprotein provided that 2–200 pmol P450 per electrode has been adsorbed.Electron transfer, direct electrochemical reduction and interaction with P450 substrates (oxygen, benzphetamine, lanosterol) and inhibitor ketoconazole were analyzed using cyclic voltammetry (CV), square wave (SWV) or differential pulse (DPV) voltammetry, and amperometry.

[1]  Juozas Kulys,et al.  Printed amperometric sensor based on TCNQ and cholinesterase , 1991 .

[2]  Electrochemistry in nanoparticle science , 2002 .

[3]  Allen J. Bard,et al.  Electrochemical Methods: Fundamentals and Applications , 1980 .

[4]  V. Urlacher,et al.  Redox properties of cytochrome p450BM3 measured by direct methods. , 2003, European journal of biochemistry.

[5]  Joseph Wang Nanomaterial-based electrochemical biosensors. , 2005, The Analyst.

[6]  J. Miners,et al.  Electrochemical characterisation of the human cytochrome P450 CYP2C9. , 2005, Biochemical pharmacology.

[7]  J. Rusling,et al.  Electroactive Myoglobin-Surfactant Films in a Bicontinuous Microemulsion , 1995 .

[8]  Christopher J. Kiely,et al.  From monolayers to nanostructured materials: an organic chemist's view of self-assembly , 1996 .

[9]  C. W. Fisher,et al.  Application of electrochemistry for P450-catalyzed reactions. , 1996, Methods in enzymology.

[10]  Andrew K. Udit,et al.  Electrochemistry of heme-thiolate proteins. , 2005, Biochemical and biophysical research communications.

[11]  D. Lewis,et al.  Interactions between redox partners in various cytochrome P450 systems: functional and structural aspects. , 2000, Biochimica et biophysica acta.

[12]  Shaojun Dong,et al.  Direct electron transfer between hemoglobin and a glassy carbon electrode facilitated by lipid-protected gold nanoparticles. , 2002, Biochimica et biophysica acta.

[13]  A. V. Lisitsa,et al.  Cytochrome P450 Database , 2001, SAR and QSAR in environmental research.

[14]  J. Schenkman,et al.  Direct electron injection from electrodes to cytochromeP450cam in biomembrane-like films , 1997 .

[15]  M. Natan,et al.  MORPHOLOGY-DEPENDENT ELECTROCHEMISTRY OF CYTOCHROME C AT AU COLLOID-MODIFIED SNO2 ELECTRODES , 1996 .

[16]  E. Wang,et al.  Gold Nanoparticles as Fine Tuners of Electrochemical Properties of the Electrode/Solution Interface , 2002 .

[17]  A. Karyakin,et al.  Prussian blue based nanoelectrode arrays for H(2)O(2) detection. , 2004, Analytical chemistry.

[18]  R. Kizek,et al.  Square wave and elimination voltammetric analysis of azidothymidine in the presence of oligonucleotides and chromosomal DNA. , 2004, Bioelectrochemistry.

[19]  Elizabeth M. J. Gillam,et al.  Direct electrochemistry of enzymes from the cytochrome P450 2C family , 2005 .

[20]  Y. Imai,et al.  Multiple forms of cytochrome P-450 purified from liver microsomes of phenobarbital- and 3-methylcholanthrene-pretreated rabbits. I. Resolution, purificaton, and molecular properties. , 1980, Journal of biochemistry.

[21]  H. Michel,et al.  Use of nanogold- and fluorescent-labeled antibody Fv fragments in immunocytochemistry. , 1996, The journal of histochemistry and cytochemistry : official journal of the Histochemistry Society.

[22]  C. Cl Higher-throughput screening with human cytochromes P450. , 1999 .

[23]  Yuri D. Ivanov,et al.  Nanotechnologies in proteomics , 2006, Proteomics.

[24]  Y. Imai,et al.  Purification of a substrate complex of cytochrome P-450 from liver microsomes of 3-methylcholanthrene-treated rabbits. , 1976, Biochemical and biophysical research communications.

[25]  G. P. Kuznetsova,et al.  Heme and apoprotein modification of cytochrome P450 2B4 during its oxidative inactivation in monooxygenase reconstituted system. , 1999, Free radical biology & medicine.

[26]  James F. Rusling,et al.  Enhanced electron transfer for myoglobin in surfactant films on electrodes , 1993 .

[27]  Sandro Carrara,et al.  Direct electron transfer between cytochrome P450scc and gold nanoparticles on screen-printed rhodium-graphite electrodes. , 2005, Biosensors & bioelectronics.

[28]  Lin He,et al.  Nanoparticles for bioanalysis. , 2003, Current opinion in chemical biology.

[29]  Ulla Wollenberger,et al.  Cytochrome P450 biosensors-a review. , 2005, Biosensors & bioelectronics.

[30]  J. Rusling Enzyme Bioelectrochemistry in Cast Biomembrane-Like Films , 1998 .

[31]  Andrew K. Udit,et al.  Protein-surfactant film voltammetry of wild-type and mutant cytochrome P450 BM3. , 2005, Inorganic chemistry.

[32]  M. J. Coon,et al.  Purified liver microsomal cytochrome P-450. Electron-accepting properties and oxidation-reduction potential. , 1975, The Journal of biological chemistry.

[33]  R. ffrench-Constant,et al.  Methoxy-resorufin ether as an electrochemically active biological probe for cytochrome P450 O-demethylation. , 2006, Bioelectrochemistry.

[34]  L. Krippahl,et al.  Electrochemical studies on small electron transfer proteins using membrane electrodes , 2003 .

[35]  T. Omura,et al.  THE CARBON MONOXIDE-BINDING PIGMENT OF LIVER MICROSOMES. II. SOLUBILIZATION, PURIFICATION, AND PROPERTIES. , 1964, The Journal of biological chemistry.

[36]  Ulla Wollenberger,et al.  Direct electron transfer of cytochrome P450 2B4 at electrodes modified with nonionic detergent and colloidal clay nanoparticles. , 2004, Analytical chemistry.

[37]  Xiaole Chen,et al.  Ordered Electrochemically Active Films of Hemoglobin, Didodecyldimethylammonium Ions, and Clay , 1999 .

[38]  Douglas S Clark,et al.  High-throughput screening of biocatalytic activity: applications in drug discovery. , 2006, Current opinion in chemical biology.

[39]  M. Waterman,et al.  Characterization and catalytic properties of the sterol 14alpha-demethylase from Mycobacterium tuberculosis. , 1999, Proceedings of the National Academy of Sciences of the United States of America.

[40]  E. Wang,et al.  Lipid membrane immobilized horseradish peroxidase biosensor for amperometric determination of hydrogen peroxide. , 2003, Biosensors & bioelectronics.

[41]  A. Archakov,et al.  Electrochemical reduction of cytochrome P450 as an approach to the construction of biosensors and bioreactors. , 2005, Journal of inorganic biochemistry.

[42]  James F Rusling,et al.  An amperometric biosensor with human CYP3A4 as a novel drug screening tool. , 2003, Biochemical pharmacology.

[43]  J. Rusling,et al.  Myoglobin retains iron heme and near-native conformation in DDAB films prepared from pH 5 to 7 dispersions , 2006 .

[44]  M. Smyth,et al.  Reactivities of organic phase biosensors: 6. Square-wave and differential pulse studies of genetically engineered cytochrome P450(cam) (CYP101) bioelectrodes in selected solvents. , 2003, Biosensors & bioelectronics.

[45]  O. Pelkonen,et al.  Multiple P450 substrates in a single run: rapid and comprehensive in vitro interaction assay. , 2005, European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences.