Practical application of cytochrome P450

Biological and Pharmaceutical Bulletin

Volumn 35, Issue 6, 2012, Pages 844-849

  Sakaki, Toshiyuki ^a  

^a TOYAMA PREFECTURAL UNIVERSITY   (Japan)

Author keywords

Bioconversion; Bioremediation; Biosensor; P450; Practical application

Indexed keywords

CALCITRIOL; CYTOCHROME P450; CYTOCHROME P450 105A3; CYTOCHROME P450 152A1; CYTOCHROME P450 152A2; CYTOCHROME P450 152B1; CYTOCHROME P450 BM3; DIOXIN; HYDROGEN PEROXIDE; POLYCHLORINATED BIPHENYL; PRAVASTATIN; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; UNCLASSIFIED DRUG;

BIOCATALYSIS; BIOCHIP; BIOREMEDIATION; BIOSENSOR; BIOTECHNOLOGY; DRUG DETERMINATION; DRUG SYNTHESIS; DRUG TRANSFORMATION; ELECTRODE; ELECTRON TRANSPORT; ENANTIOSELECTIVITY; ENZYME ACTIVITY; ENZYME ENGINEERING; ENZYME STABILITY; ENZYME SUBSTRATE COMPLEX; GENETIC ENGINEERING; HUMAN; HYDROXYLATION; MOLECULAR CLONING; NONHUMAN; REVIEW; SIGNAL TRANSDUCTION; SOIL POLLUTION; STREPTOMYCES; STREPTOMYCES CARBOPHILUS; WATER POLLUTION;

EID: 84861868170     PISSN: 09186158     EISSN: 13475215     Source Type: Journal    
DOI: 10.1248/bpb.35.844     Document Type: Review

References (51)

1. Tsujita Y, Ikeda M, Serizawa N, Hishinuma A, Komai T. Pravastatin sodium: new clinical aspects and recent progress. Annu. Per. Sankyo Res. Lab., 49, 1-61 (1997).
2. Narhi LO, Fulco AJ. Phenobarbital induction of a soluble cytochrome P-450-dependent fatty acid monooxygenase in Bacillus megaterium. J. Biol. Chem., 257, 2147-2150 (1982).
3. Watanabe I, Nara F, Serizawa N. Cloning, characterization and expression of the gene encoding cytochrome P-450sca-2 from Streptomyces carbophilus involved in production of pravastatin, a specific HMG-CoA reductase inhibitor. Gene, 163, 81-85 (1995).
4. Sasaki J, Mikami A, Mizoue K, Omura S. Transformation of 25- and 1 alpha-hydroxyvitamin D3 to 1 alpha, 25-dihydroxyvitamin D3 by using Streptomyces sp. strains. Appl. Environ. Microbiol., 57, 2841-2846 (1991).
5. Sasaki J, Miyazaki A, Saito M, Adachi T, Mizoue K, Hanada K, Omura S. Transformation of vitamin D3 to 1 alpha,25-dihydroxyvitamin D3 via 25-hydroxyvitamin D3 using Amycolata sp. strains. Appl. Microbiol. Biotechnol., 38, 152-157 (1992).
6. Kawauchi H, Sasaki J, Adachi T, Hanada K, Beppu T, Horinouchi S. Cloning and nucleotide sequence of a bacterial cytochrome P-450VD25 gene encoding vitamin D-3 25-hydroxylase. Biochim. Biophys. Acta, 1219, 179-183 (1994).
7. Yasutake Y, Fujii Y, Nishioka T, Cheon WK, Arisawa A, Tamura T. Structural evidence for enhancement of sequential vitamin D3 hydroxylation activities by directed evolution of cytochrome P450 vitamin D3 hydroxylase. J. Biol. Chem., 285, 31193-31201 (2010).
8. Sugimoto H, Shinkyo R, Hayashi K, Yoneda S, Yamada M, Kamakura M, Ikushiro S, Shiro Y, Sakaki T. Crystal structure of CYP105A1 (P450SU-1) in complex with 1alpha,25-dihydroxyvitamin D3. Biochemistry, 47, 4017-4027 (2008).
9. Hayashi K, Sugimoto H, Shinkyo R, Yamada M, Ikeda S, Ikushiro S, Kamakura M, Shiro Y, Sakaki T. Structure-based design of a highly active vitamin D hydroxylase from Streptomyces griseolus CYP105A1. Biochemistry, 47, 11964-11972 (2008).
10. Hayashi K, Yasuda K, Sugimoto H, Ikushiro S, Kamakura M, Kittaka A, Horst RL, Chen TC, Ohta M, Shiro Y, Sakaki T. Three-step hydroxylation of vitamin D3 by a genetically engineered CYP105A1: enzymes and catalysis. FEBS J., 277, 3999-4009 (2010).
11. Mahato SB, Garai S. Advances in microbial steroid biotransformation. Steroids, 62, 332-345 (1997).
12. Sonomoto K, Hoq MM, Tanaka A, Fukui S. 11beta-Hydroxylation of cortexolone (reichstein compound S) to hydrocortisone by Curvularia lunata entrapped in photo-cross-linked resin gels. Appl. Environ. Microbiol., 45, 436-443 (1983).
13. Suzuki K, Sanga K, Chikaoka Y, Itagaki E. Purification and properties of cytochrome P-450 (P-450lun) catalyzing steroid 11 betahydroxylation in Curvularia lunata. Biochim. Biophys. Acta, 1203, 215-223 (1993).
14. Sakaki T, Akiyoshi-Shibata M, Yabusaki Y, Manabe K, Murakami H, Ohkawa H. Progesterone metabolism in recombinant yeast simultaneously expressing bovine cytochromes P450c17 (CYP17A1) and P450c21 (CYP21B1) and yeast NADPH-P450 oxidoreductase. Pharmacogenetics, 1, 86-93 (1991).
15. Shibata M, Sakaki T, Yabusaki Y, Murakami H, Ohkawa H. Genetically engineered P450 monooxygenases: construction of bovine P450c17/yeast reductase fused enzymes. DNA Cell Biol., 9, 27-36 (1990).
16. Sakaki T, Shibata M, Yabusaki Y, Murakami H, Ohkawa H. Expression of bovine cytochrome P450c21 and its fused enzymes with yeast NADPH-cytochrome P450 reductase in Saccharomyces cerevisiae. DNA Cell Biol., 9, 603-614 (1990).
17. Szczebara FM, Chandelier C, Villeret C, Masurel A, Bourot S, Duport C, Blanchard S, Groisillier A, Testet E, Costaglioli P, Cauet G, Degryse E, Balbuena D, Winter J, Achstetter T, Spagnoli R, Pompon D, Dumas B. Total biosynthesis of hydrocortisone from a simple carbon source in yeast. Nat. Biotechnol., 21, 143-149 (2003).
18. Hakki T, Zearo S, Drǎ;gan CA, Bureik M, Bernhardt R. Coexpression of redox partners increases the hydrocortisone (cortisol) production efficiency in CYP11B1 expressing fission yeast Schizosaccharomyces pombe. J. Biotechnol., 133, 351-359 (2008).
19. Nguyen KT, Virus C, Günnewich N, Hannemann F, Bernhardt R. Changing the regio-selectivity of a P450 from C15 to C11 hydroxylation of progesterone. ChemBioChem (2012), doi:10.1002/cbic.201100811.
20. Girhard M, Machida K, Itoh M, Schmid RD, Arisawa A, Urlacher VB. Regioselective biooxidation of (+)-valencene by recombinant E. coli expressing CYP109B1 from Bacillus subtilis in a two-liquidphase system. Microb. Cell Fact., 8, 36-47 (2009).
21. Wong TS, Arnold FH, Schwaneberg U. Laboratory evolution of cytochrome p450 BM-3 monooxygenase for organic cosolvents. Biotechnol. Bioeng., 85, 351-358 (2004).
22. Otey CR, Bandara G, Lalonde J, Takahashi K, Arnold FH. Preparation of human metabolites of propranolol using laboratory-evolved bacterial cytochromes P450. Biotechnol. Bioeng., 93, 494-499 (2006).
23. Fisher CW, Shet MS, Caudle DL, Martin-Wixtrom CA, Estabrook RW. High-level expression in Escherichia coli of enzymatically active fusion proteins containing the domains of mammalian cytochromes P450 and NADPH-P450 reductase flavoprotein. Proc. Natl. Acad. Sci. U.S.A., 89, 10817-10821 (1992).
24. Sakaki T, Kominami S, Hayashi K, Akiyoshi-Shibata M, Yabusaki Y. Molecular engineering study on electron transfer from NADPHP450 reductase to rat mitochondrial P450c27 in yeast microsomes. J. Biol. Chem., 271, 26209-26213 (1996).
25. Fujii T, Fujii Y, Machida K, Ochiai A, Ito M. Efficient biotransformations using Escherichia coli with tolC acrAB mutations expressing cytochrome P450 genes. Biosci. Biotechnol. Biochem., 73, 805-810 (2009).
26. Sulistyaningdyah WT, Ogawa J, Li QS, Maeda C, Yano Y, Schmid RD, Shimizu S. Hydroxylation activity of P450 BM-3 mutant F87V towards aromatic compounds and its application to the synthesis of hydroquinone derivatives from phenolic compounds. Appl. Microbiol. Biotechnol., 67, 556-562 (2005).
27. Glieder A, Farinas ET, Arnold FH. Laboratory evolution of a soluble, self-sufficient, highly active alkane hydroxylase. Nat. Biotechnol., 20, 1135-1139 (2002).
28. Peters MW, Meinhold P, Glieder A, Arnold FH. Regio- and enantioselective alkane hydroxylation with engineered cytochromes P450 BM-3. J. Am. Chem. Soc., 125, 13442-13450 (2003).
29. Cirino PC, Tang Y, Takahashi K, Tirrell DA, Arnold FH. Global incorporation of norleucine in place of methionine in cytochrome P450 BM-3 heme domain increases peroxygenase activity. Biotechnol. Bioeng., 83, 729-734 (2003).
30. Bloom JD, Labthavikul ST, Otey CR, Arnold FH. Protein stability promotes evolvability. Proc. Natl. Acad. Sci. U.S.A., 103, 5869-5874 (2006).
31. Otey CR, Bandara G, Lalonde J, Takahashi K, Arnold FH. Preparation of human metabolites of propranolol using laboratory-evolved bacterial cytochromes P450. Biotechnol. Bioeng., 93, 494-499 (2006).
32. Matsunaga I, Yokotani N, Gotoh O, Kusunose E, Yamada M, Ichihara K. Molecular cloning and expression of fatty acid alpha-hydroxylase from Sphingomonas paucimobilis. J. Biol. Chem., 272, 23592-23596 (1997).
33. Fujishiro T, Shoji O, Nagano S, Sugimoto H, Shiro Y, Watanabe Y. Crystal structure of H2O2-dependent cytochrome P450SPalpha with its bound fatty acid substrate: insight into the regioselective hydroxylation of fatty acids at the alpha position. J. Biol. Chem., 286, 29941-29950 (2011).
34. Girhard M, Schuster S, Dietrich M, Dürre P, Urlacher VB. Cytochrome P450 monooxygenase from Clostridium acetobutylicum: a new alpha-fatty acid hydroxylase. Biochem. Biophys. Res. Commun., 362, 114-119 (2007).
35. Shoji O, Fujishiro T, Nagano S, Tanaka S, Hirose T, Shiro Y, Watanabe Y. Understanding substrate misrecognition of hydrogen peroxide dependent cytochrome P450 from Bacillus subtilis. J. Biol. Inorg. Chem., 15, 1331-1339 (2010).
36. Maurer SC, Schulze H, Schmid RD, Urlacher V. Immobilization of P450 BM-3 and NADP+ cofactor recycling system: Tpwards a technical application of heme-containing monooxygenases in fine chemical synthesis. Adv. Synth. Catal., 345, 802-810 (2003).
37. Denisov IG, Sligar SG. Cytochromes P450 in nanodiscs. Biochim. Biophys. Acta, 1814, 223-229 (2011).
38. Baj-Rossi C, Micheli GD, Carrara S. P450-based nano-bio-sensors for personalized medicine. Biosensors-Emerging Materials and Applications. (Serra PA ed.) Chapter 21, InTech (2011).
39. Joseph S, Rusling JF, Lvov YM, Friedberg T, Fuhr U. An amperometric biosensor with human CYP3A4 as a novel drug screening tool. Biochem. Pharmacol., 65, 1817-1826 (2003).
40. Mie Y, Suzuki M, Komatsu Y. Electrochemically driven drug metabolism by membranes containing human cytochrome P450. J. Am. Chem. Soc., 131, 6646-6647 (2009).
41. Nicolini C, Erokhin V, Ghisellini P, Paternolli C, Ram MK, Sivozhelezov V. P450scc engineering and nanostructuring for cholesterol sensing. Langmuir, 17, 3719-3726 (2001).
42. Sakaki T, Munetsuna E. Enzyme systems for biodegradation of polychlorinated dibenzo-p-dioxins. Appl. Microbiol. Biotechnol., 88, 23-30 (2010).
43. Shinkyo R, Sakaki T, Ohta M, Inouye K. Metabolic pathways of dioxin by CYP1A1: species difference between rat and human CYP1A subfamily in the metabolism of dioxins. Arch. Biochem. Biophys., 409, 180-187 (2003).
44. Shinkyo R, Sakaki T, Takita T, Ohta M, Inouye K. Generation of 2,3,7,8-TCDD-metabolizing enzyme by modifying rat CYP1A1 through site-directed mutagenesis. Biochem. Biophys. Res. Commun., 308, 511-517 (2003).
45. Bumpus JA, Tien M, Wright D, Aust SD. Oxidation of persistent environmental pollutants by a white rot fungus. Science, 228, 1434-1436 (1985).
46. Kasai N, Ikushiro SI, Shinkyo R, Yasuda K, Hirosue S, Arisawa A, Ichinose H, Wariishi H, Sakaki T. Metabolism of mono- and dichloro-dibenzo-p-dioxins by Phanerochaete chrysosporium cytochromes P450. Appl. Microbiol. Biotechnol., 86, 773-780 (2010).
47. Yamazaki K, Suzuki M, Itoh T, Yamamoto K, Kanemitsu M, Matsumura C, Nakano T, Sakaki T, Fukami Y, Imaishi H, Inui H. Structural basis of species differences between human and experimental animal CYP1A1s in metabolism of 3,3′,4,4′,5-pentachlorobiphenyl. J. Biochem., 149, 487-494 (2011).
48. Paul D, Pandey G, Jain RK. Suicidal genetically engineered micro-organisms for bioremediation: need and perspectives. Bioessays, 27, 563-573 (2005).
49. Katsumoto Y, Fukuchi-Mizutani M, Fukui Y, Brugliera F, Holton TA, Karan M, Nakamura N, Yonekura-Sakakibara K, Togami J, Pigeaire A, Tao GQ, Nehra NS, Lu CY, Dyson BK, Tsuda S, Ashikari T, Kusumi T, Mason JG, Tanaka Y. Engineering of the rose flavonoid biosynthetic pathway successfully generated blue-hued flowers accumulating delphinidin. Plant Cell Physiol., 48, 1589-1600 (2007).
50. Kawahigashi H, Hirose S, Ohkawa H, Ohkawa Y. Phytoremediation of the herbicides atrazine and metolachlor by transgenic rice plants expressing human CYP1A1, CYP2B6, and CYP2C19. J. Agric. Food Chem., 54, 2985-2991 (2006).
51. Hannemann F, Bichet A, Ewen KM, Bernhardt R. Cytochrome P450 systems-biological variations of electron transport chains. Biochim. Biophys. Acta, 1770, 330-344 (2007).