Engineering and application of P450 monooxygenases in pharmaceutical and metabolite synthesis

Current Opinion in Chemical Biology

Volumn 17, Issue 2, 2013, Pages 271-275

  Caswell, Jill M ^a   O'Neill, Maeve ^a   Taylor, Steve J C ^a   Moody, Thomas S ^a  

^a Almac ^*  (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ARTEMISININ; BACTERIAL ENZYME; CYTOCHROME P450; FUNGAL ENZYME; HYDROCARBON; VERAPAMIL;

BIOENGINEERING; BIOSYNTHESIS; DRUG METABOLISM; EPOXIDATION; HUMAN; MEDICAL TECHNOLOGY; METABOLITE; OXIDATION; REVIEW;

ARTEMISININS; BACTERIAL PROTEINS; CHEMISTRY, PHARMACEUTICAL; CYTOCHROME P-450 ENZYME SYSTEM; FUNGAL PROTEINS; HUMANS; PROTEIN ENGINEERING; RECOMBINANT PROTEINS;

BACTERIA (MICROORGANISMS);

EID: 84876741719     PISSN: 13675931     EISSN: 18790402     Source Type: Journal    
DOI: 10.1016/j.cbpa.2013.01.028     Document Type: Review

References (55)

1. Das N., Chandran P. Microbial degradation of petroleum hydrocarbon contaminants: an overview. Biotechnol Res Int 2011, 10.4061/2011/941810.
2. Chen T.C., Sakaki T., Yamamoto K., Kittaka A. The roles of cytochrome P450 enzymes in prostate cancer development and treatment. Anticancer Res 2012, 32:291-298.
3. Li A.F., Shen G.L., Jiao S.Y., Li H., Wang Q. Metabolic detoxification of bakuchiol is mediated by cytochrome P450 enzymes in human liver microsomes. Beijing Da Xue Xue Bao 2012, 44:431-436.
4. Cresner B., Petric S. Cytochrome P450 enzymes in the fungal kingdom. Biochim Biophys Acta: Proteins Proteomics 2011, 1814:29-35.
5. Lamb D.C., Lei L., Warrilow A.G., Lepesheva G.I., Mullins J.G., Waterman M.R., Kelly S.L. The first virally encoded cytochrome P450. J Virol 2009, 83:8266-8269.
6. Zhang J.D., Li A.T., Yu H.L., Imanaka T., Xu J.H. Synthesis of optically pure S-sulfoxide by Escherichia coli transformant cells coexpressing the P450 monooxygenase and glucose dehydrogenase genes. J Ind Microbiol Biotechnol 2011, 38:633-641.
7. Lee S.H., Kwon Y.C., Kim D.M., Park C.B. Cytochrome P450-catalyzed O-dealkylation coupled with photochemical NADPH regeneration. Biotechnol Bioeng 2013, 110:383-390.
8. Roberts K.M., Jones J.P. Anilinic N-oxides support cytochrome P450-mediated N-dealkylation through hydrogen-atom transfer. Chem Eur J 2010, 16:8096-8107.
9. Ortiz de Montellano P.R. Hydrocarbon hydroxylation by cytochrome P450 enzymes. Chem Rev 2009, 110:932-948.
10. Fasan R. Tuning P450 enzymes as oxidation catalysts. ACS Catal 2012, 2:647-666.
11. Urlacher V.B., Girhard M. Cytochrome P450 monooxygenases: an update on perspectives for synthetic application. Trends Biotechnol 2012, 30:26-36.
12. O'Reilly E., Köhler V., Flitsch S.L., Turner N.J. Cytochromes P450 as useful biocatalysts: addressing the limitations. Chem Commun 2011, 47:2490-2501.
13. Cojocaru V., Balali-Mood K., Sansom M.S.P., Wade R.C. Structure and dynamics of the membrane-bound cytochrome P450 2C9. PLoS Comput Biol 2011, 7:e1002152. 10.1371/journal.pcbi.1002152.
14. Sandee D., Miller W.L. High-yield expression of a catalytically active membrane-bound protein: human P450 oxidoreductase. Endocrinology 2011, 152:2904-2908.
15. Omura T. Structural diversity of cytochrome P450 enzyme system. J Biochem 2010, 147:297-306.
16. Armstrong C.T., Watkins D.W., Anderson J.L.R. Constructing manmade enzymes for oxygen. Dalton Trans 2013, advance article.
17. Van L.M., Sarda S., Hargreaves J.A., Rostami-Hodjegan A. Metabolism of dextrorphan by CYP2D6 in different recombinantly expressed systems and its implications for the in vitro assessment of dextromethorphan metabolism. J Pharmaceut Sci 2009, 98:763-771.
18. Locuson C.W., Ethell B.T., Voice M.W., Lee D., Feenstra K.L. Evaluation of Escherichia coli membrane preparations of canine CYP1A1, 2B11, 2C21, 2C41, 2D15, 3A12 and 3A26 with coexpressed canine cytochrome P450 reductase. Drug Metab Dispos 2009, 37:457-461.
19. Fulco A.J. P450BM-3 and other inducible bacterial P450 cytochromes: biochemistry and regulation. Annu Rev Pharmacol 1991, 31:177-203.
20. Whitehouse C.J.C., Bell S.G., Wong L.-L. P450 BM3 (CYP102A1): connecting the dots. Chem Soc Rev 2012, 41:1218-1260.
21. Gillam E.M.J. Engineering cytochrome P450 enzymes. Chem Res Toxicol 2008, 21:220-231.
22. Romero P.A., Arnold F.H. Exploring protein fitness landscapes by directed evolution. Nat Rev Mol Cell Biol 2009, 10:866-876.
23. Seifert A., Vomund S., Grohmann K., Kriening S., Urlacher V.B., Laschat S., Pleiss J. Rational design of a minimal and highly enriched CYP102A1mutant library with improved regio-, stereo- and chemoselectivity. Chem Biol Chem 2009, 10:853-861.
24. Tang W.L., Li Z., Zhao H. Inverting the enantioselectivity of P450pyr monooxygenase by directed evolution. Chem Commun 2010, 46:5461-5463.
25. Agudo R., Roiban G.D., Reetz M.T. Achieving regio- and enantioselectivity of P450-catalyzed oxidative CH activation of small functionalized molecules by structure-guided directed evolution. Chembiochem 2012, 13:1465-1473.
26. Tsotsou G.E., Sideri A., Goyal A., Di Nardo G., Gilardi G. Identification of mutant Asp251Gly/Gln307His of cytochrome P450 BM3 for the generation of metabolites of diclofenac, ibuprofen and tolbutamide. Chemistry 2012, 18:3582-3588.
27. Williams P.A., Cosme J., Vinkovic D.M., Ward A., Angove H.C., Day P.J., Vonrhein C., Tickle I.J., Jhoti H. Crystal structures of human cytochrome P450 3A4 bound to metyrapone and progesterone. Science 2004, 305:683-686.
28. Mosher C.M., Hummel M.A., Tracy T.S., Rettie A.E. Functional analysis of phenylalanine residues in the active site of cytochrome P450 2C9. Biochemistry 2008, 47:11725-11734.
29. Khan K.K., He Y.Q., Domanski T.L., Halpert J.R. Midazolam oxidation by cytochrome P450 3A4 and active-site mutants: an evaluation of multiple binding sites and of the metabolic pathway that leads to enzyme inactivation. Mol Pharmacol 2002, 61:495-506.
30. Miksys S., Tyndale R.F. Cytochrome P450-mediated drug metabolism in the brain. J Psychiatry Neurosci 2012, 37:120133.
31. Schroer K., Kittelmann M., Lütz S. Recombinant human cytochrome P450 monooxygenases for drug metabolite synthesis. Biotechnol Bioeng 2010, 106:699-706.
32. Weis R., Winkler M., Schittmayer M., Kambourakis S., Vink M., Rozzell J.D., Glieder A. A diversified library of bacterial and fungal bifunctional cytochrome P450 enzymes for drug metabolite synthesis. Adv Synth Catal 2009, 351:2140-2146.
33. Baillie T.A. Metabolism and toxicity of drugs. Two decades of progress in industrial drug metabolism. Chem Res Toxicol 2008, 21:129-137.
34. Kleser M., Hannemann F., Hutter M., Zapp J., Bernhardt R. CYP105A1 mediated 3-hydroxylation of glimepiride and glibenclamide using a recombinant Bacillus megaterium whole-cell catalyst. J Biotechnol 2012, 157:405-412.
35. Di Nardo G., Gilardi G. Optimization of the bacterial cytochrome P450 BM3 system for the production of human drug metabolites. Int J Mol Sci 2012, 13:15901-15924.
36. Sawayama A.M., Chen M.M., Kulanthaivel P., Kuo M.S., Hemmerle H., Arnold F.H. A panel of cytochrome P450 BM3 variants to produce drug metabolites and diversify lead compounds. Chemistry 2009, 15:11723-11729.
37. Dietrich J.A., Yoshikuni Y., Fisher K.J., Woolard F.X., Ockey D., McPhee D.J., Renninger N.S., Chang M.C., Baker D., Keasling J.D. A novel semi-biosynthetic route for artemisinin production using engineered substrate-promiscuous P450(BM3). ACS Chem Biol 2009, 4:261-267.
38. Grogan G. Cytochromes P450: exploiting diversity and enabling application as biocatalysts. Curr Opin Chem Biol 2011, 15:241-248.
39. Salazar O., Cirino P.C., Arnold F.H. Thermostabilization of a cytochrome P450 peroxygenase. Chembiochem 2003, 4:891-893.
40. Talakad J.C., Wilderman P.R., Davydov D.R., Kumar S., Halpert J.R. Rational engineering of cytochromes P450 2B6 and 2B11 for enhanced stability: insights into structural importance of residue 334. Arch Biochem Biophys 2010, 494:151-158.
41. Eiben S., Bartelmäs H., Urlacher V.B. Construction of a thermostable cytochrome P450 chimera derived from self-sufficient mesophilic parents. Appl Microbiol Biotechnol 2007, 75:1055-1061.
42. Weber E., Sirim D., Schreiber T., Thomas B., Pleiss J., Hunger M., Gläser R., Urlacher V.B. Immobilization of P450 BM-3 monooxygenase on mesoporous molecular sieves with different pore diameters. J Mol Catal B: Enzym 2010, 64:29-37.
43. Kumar S., Sun L., Liu H., Muralidhara B.K., Halpert J.R. Engineering mammalian cytochrome P450 2B1 by directed evolution for enhanced catalytic tolerance to temperature and dimethyl sulfoxide. Protein Eng Des Sel 2006, 19:547-554.
44. Wong T.S., Arnold F.H., Schwaneberg U. Laboratory evolution of cytochrome p450 BM-3 monooxygenase for organic cosolvents. Biotechnol Bioeng 2004, 85:351-358.
45. Brenelli E.C.S., Fernandes J.L.N. Stereoselective acylation of 1,2-azidoalchols with vinyl acetate catalysed by lipase Amano PS. Tetrahedron: Asymmetry 2003, 14:1255-1259.
46. Lin G., Liue H.-S. Ultrasound-promoted lipase-catalyzed reactions. Tetrahedron Lett 1995, 36:6067-6068.
47. Ribeiro C.M.R., Passaroto E.N., Brenelli E.C.S. Ultrasound in enzymatic resolution of ethyl 3-hydroxy-3-phenylpropanoate. Tetrahedron Lett 2001, 42:6477-6479.
48. Mawson R., Gamage M., Terefe N.T., Knoerzer K. Ultrasound in enzyme activation and inactivation. Ultrasound Technologies for Food and Bioprocessing 2011, H. Feng, G.V. Barbosa-Canovas, J. Weiss (Eds.).
49. Souza M., Mezadri E.T., Zimmerman E., Leaes E.X., Bassaco M.M., Dal Prá V., Foletto E., Cancellier A., Terra L.M., Jahn S.L., Mazutti M.A. Evaluation of activity of a commercial amylase under ultrasound-assisted irradiation. Ultrason Sonochem 2013, 20:89-94. (Epub 2012 June 1). 10.1016/j.ultsonch.2012.05.012.
50. Elibol M., Mavituna F. Effect of perfluorodecalin as an oxygen carrier on actinorhodin production by Streptomyces coelicolor A3(2). Appl Microbiol Biotechnol 1995, 43:206-210.
51. Ntwampe S.K.O., Williams C.C., Sheldon M.S. Water-immiscible dissolved oxygen carriers in combination with Pluronic F68 in bioreactors. Afr J Biotechnol 2010, 9:1106-1114.
52. de Raadt A., Griengl H., Weber H. The concept of docking and protecting groups in biohydroxylation. Chemistry 2001, 7:27-31.
53. de Raadt A., Griengl H. The use of substrate engineering in biohydroxylation. Curr Opin Biotechnol 2002, 13:537-542.
54. Munzer D.F., Meinhold P., Peters M.W., Feichtenhofer S., Griengl H., Arnold F.H., Glieder A., de Raadt A. Stereoselective hydroxylation of an achiral cyclopentanecarboxylic acid derivative using engineered P450s BM-3. Chem Commun (Camb) 2005, 20:2597-2599.
55. Li S., Chaulagain M.R., Knauff A.R., Podust L.M., Montgomery J., Sherman D.H. Selective oxidation of carbolide CH bonds by an engineered macrolide P450 mono-oxygenase. Proc Natl Acad Sci U S A 2009, 106:18463-18468.