Explaining the atypical reaction profiles of heme enzymes with a novel mechanistic hypothesis and kinetic treatment

PLoS ONE

Volumn 5, Issue 5, 2010, Pages

  Manoj, Kelath Murali ^a   Baburaj, Arun ^b   Ephraim, Binoy ^b   Pappachan, Febin ^b   Maviliparambathu, Pravitha Parapurathu ^b   Vijayan, Umesh K ^b   Narayanan, Sivaprasad Valiyaveettil ^b   Periasamy, Kalaiselvi ^a   George, Ebi Ashley ^a   Mathew, Lazar T ^a  

^a VIT UNIVERSITY   (India)

^b MET'S School of Engineering   (India)

Author keywords

[No Author keywords available]

Indexed keywords

2,2' AZINOBIS(3 ETHYLBENZOTHIAZOLINE 6 SULFONIC ACID); CHLORIDE PEROXIDASE; CYTOCHROME P450; CYTOCHROME P450 1A2; CYTOCHROME P450 2C9; CYTOCHROME P450 2E1; PYROGALLOL; 1 (3 PICOLINIUM) 12 TRIETHYLAMMONIUM DODECANE DIBROMIDE; 1-(3-PICOLINIUM)-12-TRIETHYLAMMONIUM-DODECANE DIBROMIDE; 2,2'-AZINOBIS(3-ETHYLBENZOTHIAZOLINE-6-SULFONIC ACID); 4 NITROPHENOL; 4-NITROPHENOL; 7 O ETHYL FANGCHINOLINE; 7-O-ETHYL FANGCHINOLINE; BENZYLISOQUINOLINE DERIVATIVE; DICLOFENAC; HEME; NITROPHENOL; PEROXIDE; PICOLINE DERIVATIVE; SULFONIC ACID DERIVATIVE; THIAZOLE DERIVATIVE;

ARTICLE; CONTROLLED STUDY; ENZYME INHIBITION; ENZYME KINETICS; ENZYME MECHANISM; ENZYME SUBSTRATE COMPLEX; PEROXIDATION; STEADY STATE; BIOCATALYSIS; BIOLOGICAL MODEL; HYDROXYLATION; KINETICS; METABOLISM; OXIDATION REDUCTION REACTION;

MAMMALIA;

BENZYLISOQUINOLINES; BIOCATALYSIS; CHLORIDE PEROXIDASE; CYTOCHROME P-450 ENZYME SYSTEM; DICLOFENAC; HEME; HYDROXYLATION; KINETICS; MODELS, BIOLOGICAL; NITROPHENOLS; OXIDATION-REDUCTION; PEROXIDES; PICOLINES; PYROGALLOL; SULFONIC ACIDS; THIAZOLES;

EID: 77956269222     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0010601     Document Type: Article

References (28)

1. Sundaramoorthy M, Terner J, Poulos TL (1995) The crystal structure of chloroperoxidase: A heme peroxidase-cytochrome P450 functional hybrid. Structure 3: 1367-1377.
2. Williams PA, Cosme J, Vinkovic DM, Ward A, Angove HC, et al. (2004) Crystal structures of human cytochrome P450 3A4 bound to metyrapone and progesterone. Science 305: 683-686.
3. Wester RM, Yano JK, Schoch GA, Yang C, Griffin KJ, et al. (2004) The structure of human cytochrome P450 2C9 complexed with flurbiprofen at 2 A ̊ resolution. J Biol Chem 279: 35630-35637.
4. Porter TD, Coon MJ (1991) Cytochrome P450: Multiplicity of isoforms, substrate and catalytic and regulatory mechanisms. J Biol Chem 266: 13469-13472.
5. Ortez de Montellano PR, Choe YS, Depillis G, Catalano CE (1987) Structuremechanism relationships in hemoproteins. J Biol Chem 262: 11641-11646.
6. Libby RD, Thomas JA, Kaiser LW, Hager LP (1981) Chloroperoxidase halogenation reactions. J Biol Chem 257: 5030-5037.
7. Guengerich FP (1991) Reactions and significance of cytochrome P450 enzymes. J Biol Chem 266: 10019-10022.
8. Manoj KM, Hager LP (2002) The catalytic utility and versatility of chloroperoxidase. Rec Res Dev Org Chem 6: 393-405.
9. Ortiz de Montellano PR (1995) Cytochrome P450: Structure, mechanism and biochemistry. Plenum Press, New York.
10. Manoj KM, Hager LP (2008) Chloroperoxidase, a Janus enzyme. Biochemistry 47: 2997-3003.
11. Lin Y, Tang C, Mei Q, Sandig G, Rodrigues DA, et al. (2001) Substrate inhibition kinetics for cytochrome P450 catalyzed reactions. Drug Metab Dispos 29: 368-374.
12. Shou M, Lin Y, Lu P, Tang C, Mei Q, et al. (2000) Enzyme kinetics of cytochrome P450 mediated reactions. Curr Drug Metab 2: 17-36.
13. Atkins WM (2005) Non-Michaelis-Menten kinetics observed in CYP catalyzed reactions. Ann Rev Pharmacol Toxicol 45: 291-310.
14. Koley AP, Robinson RC, Friedman FK (1996) Cytochrome P450 conformation and substrate interactions as probed by CO binding kinetics. Biochimie 78:706-713.
15. Copeland RA (2000) Enzymes: A practical introduction to structure, mechanism and and analysis: Wiley. pp 136-138.
16. Hollenberg PF (1992) Mechanisms of cytochrome P450 and peroxidasecatalyzed xenobiotic metabolism. FASEB J 6: 686-694.
17. Guengerich FP, Yun CH, McDonald TL (1996) Evidence for a 1-electron oxidation mechanism in N-dealkylation of N,N-dialkylanilines by cytochrome P4502B1. J Biol Chem 271: 27321-27329.
18. Zhang R, Nagraj N, Lansakara DSP, Hager LP, Newcomb M (2006) Kinetics of two-electron oxidations by the Compound I derivative of chloroperoxidase, a model for cytochrome P450 oxidants. Org Lett 8: 2731-2734.
19. McCarthy MB, White RE (1983) Functional differences between peroxidase compound I and the cytochrome P450 reactive oxygen intermediate. J Biol Chem 258: 9153-9158.
20. Bhakta MN, Wimalasena K (2005) A Mechanistic comparison between cytochrome P450 and chloroperoxidase catalyzed N-dealkylation of N,N-dialkyl anilines. Eur J Org Chem 22: 4801-4805.
21. Schlichting I, Berendzen J, Chu K, Stock AM, Maves SA, et al. (2000) The catalytic pathway of cytochrome P450cam at atomic resolution. Science 287: 1615-1622.
22. Manoj KM (2007) A novel scheme to explain the mechanistic chemistry of CYP reactions. Proceedings of the 15th International Conference on Cytochrome P450s, 97-107 (Medimond Press, Italy).
23. Manoj KM (2006) Chlorinations catalyzed by chloroperoxidase occur via a diffusible intermediate and the reaction components play multiple roles in the overall process. Biochim Biophys Acta- Proteins & Proteomics 1764: 1325-1339.
24. Casella L, Poli S, Gullotti M, Selvaggini C, Beringhelli T, et al. (1994) Chloroperoxidase catalyzed oxidation of phenols: Mechanism, selectivity and characterization of enzyme-substrate complexes. Biochemistry 33: 6377-6386.
25. Porter TD (2002) The roles of cytochrome b5 in cytochrome P450 reactions. J Biochem Mol Toxicol 16: 311-316.
26. Kumar S, Davydov DR, Halpert JR (2005) Role of cytochrome b5 in modulating peroxide-supported CYP3A4 activity: Evidence for a conformational transition and cytochrome P450 heterogeneity. Drug Metab Disp 33:1131-1136.
27. Collom SL, Laddusaw RM, Burch AM, Kuzmic P, Perry MD, et al. (2008) CYP2E1 substrate inhibition: Mechanistic interpretation through an effector site for monocyclic compounds. J Biol Chem 283: 3487-3496.
28. Yun CH, Yim SK, Kim DH, Ahn T (2006) Functional expression of human cytochrome P450 enzymes in Escherichia coli. Curr Drug Metab 7: 411-429.