Human cytochrome p450 enzymes expressed in bacteria: Reagents to probe molecular interactions in toxicology

Clinical and Experimental Pharmacology and Physiology

Volumn 25, Issue 11, 1998, Pages 877-886

  Gillam, Elizabeth M J ^a  

^a UNIVERSITY OF QUEENSLAND   (Australia)

Author keywords

Bacterial expression; Cytochrome P450; Drug metabolism; Genotoxicity testing; In vitro studies; Molecular toxicology

Indexed keywords

CYTOCHROME P450; RECOMBINANT ENZYME; UNSPECIFIC MONOOXYGENASE;

AMINO TERMINAL SEQUENCE; BACULOVIRUS; CELL CULTURE; DRUG METABOLISM; ENZYME ACTIVITY; ENZYME RECONSTITUTION; ENZYME SPECIFICITY; ESCHERICHIA COLI; EXPRESSION VECTOR; GENETIC VARIABILITY; GENOTOXICITY; HUMAN; LIVER MICROSOME; NONHUMAN; PROTEIN EXPRESSION; REVIEW; STRUCTURE ACTIVITY RELATION; TOXICITY TESTING; YEAST;

EID: 0031797278     PISSN: 03051870     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1440-1681.1998.tb02338.x     Document Type: Review

References (74)

1. Guengerich FP. Human cytochrome P450 enzymes. In: Ortiz de Montellano PR (ed.). Cytochrome P450. Plenum Press, New York. 1995; 473-535.
2. Clark BJ, Waterman MR. Heterologous expression of mammalian P450 in COS cells. Methods Enzynml. 1991; 206: 100-8.
3. Doehmer J, Oesch FV. 79 Chinese hamster cells genetically engineered for stable expression of cytochromes P450. Methods Enzymol. 1991; 206: 117-23.
4. Gonzalez FJ, Aoyama T, Gelboin HV. Expression of mammalian cytochrome P450 using vaccinia virus. Methods Enzymol. 1991; 206: 85-92.
5. Crespi CL. Expression of cytochrome P450 cDNAs in human B lymphoblastoid cells: Applications to toxicology and metabolite analysis. Methods Enzymol. 1991; 206: 123-9.
6. Gonzalez FJ, Kimura S, Tamura S, Gelboin HV. Expression of mammalian cytochrome P450 using baculovirus. Methods Enzymol. 1991; 206: 93-9.
7. Brian WR, Sari M-A, Iwasaki M, Shimada T, Kaminsky LS, Guengerich FP. Catalytic activities of human liver cytochrome P-450 IIIA4 expressed in Saccharomyces cerevisiae. Biochemistry 1990; 29: 11 280-92.
8. Brian WR, Srivastava PK, Umbenhauer DR, Lloyd RS, Guengerich FP. Expression of a human liver cytochrome P-450 protein with tolbutamide hydroxylase activity in Saccharomyees cererisiae. Biochemistry 1989; 28: 4993-9.
9. Srivastava PK, Yun C-H, Beaune PH, Ged C, Guengerich FP. Separation of human liver tolbutamine hydroxylase and (S)-mephenytoin 4′-hydroxylase cytochrome P-450 enzymes. Mol. Pharmacol. 1991; 40: 69-79.
10. Ching MS, Lennard MS, Tucker GT, Woods HF, Kelly DE, Kelly SL. The expression of human cytochrome P4501A1 in the yeast Saccharomyces cerevisiae. Biochem. Pharmacol. 1991; 42: 753-8.
11. Ellis SW, Ching MS, Watson PF et al. Catalytic activities of human debrisoquine 4-hydroxylase cytochrome P450 (CYP2D6) expressed in yeast. Biochem. Pharmacol. 1992; 44: 617-20.
12. Renaud J-P, Cullin C, Pompon D, Beaune P, Mansuy D. Expression of human liver cytochrome P450 IIIA4 in yeast: a functional model for the hepatic enzyme. Eur. J. Biochem. 1990; 194: 889-96.
13. 5. Eur. J. Biochem. 1992; 207: 109-16.
14. Guo Z, Gillam EMJ, Ohmori S, Tukey RH, Guengerich FP. Expression of modified human cytochrome P450 1A1 in Escherichia coli: Effects of 5′ substitution, stabilization, purification, spectral characterization, and catalytic properties. Arch. Biochem. Biophys. 1994; 312: 436-46.
15. Fisher CW, Caudle DL, Martin-Wixtrom C et al. High-level expression of functional cytochrome P450 1A2 in Escherichia coli. FASEB J. 1992; 6: 759-64.
16. Lee CA, Kadwell SH, Kost TA, Serabjit-Singh CJ. CYP3A4 expressed by insect cells infected with a recombinant baculovirus containing both CYP3A4 and human NADPH-cytochrome P450 reductase is catalytically similar to human liver microsomal CYP3A4. Arch. Biochem. Biophys. 1995; 319: 157-67.
17. Shimada T, Wunsch RM, Sutter TR, Guengerich FP, Gillam EMJ. Recombinant human cytochrome P450 1B1 expression in Escherichia coli. Arch. Biochem. Biophys. 1998 (in press).
18. Richardson TH, Jung F, Griffin KJ et al. Universal approach to the expression of human and rabbit cytochrome P450s of the 2C subfamily in Escherichia coli. Arch. Biochem. Biophys. 1995; 323: 87-96.
19. Sandhu P, Baba T, Guengerich FP. Expression of modified cytochrome P450 2C10 (2C9) in Escherichia coli, purification, and reconstitution of catalytic activity. Arch. Biochem. Biophys. 1993; 306: 443-50.
20. Gillam EMJ, Guo Z, Martin MV, Jenkins CM, Guengerich FP. Expression of cytochrome P450 2D6 in Escherichia coli, purification, and spectral and catalytic characterization. Arch. Biochem. Biophys. 1995; 319: 540-50.
21. Gillam EMJ, Guo Z, Guengerich FP. Expression of modified human cytochrome P450 2E1 in Escherichia coli, purification, and spectral and catalytic properties. Arch. Biochem. Biophys. 1994; 312: 59-66.
22. Gillam EMJ, Baba T, Kim B-R, Ohmori S, Guengerich FP. Expression of modified human cytochrome P450 3A4 in Escherichia coli and purification and reconstitution of the enzyme. Arch. Biochem. Biophys. 1993; 305: 123-31.
23. Shet MS, Fisher CW, Holmans PL, Estabrook RW. Human cytochrome P450 3A4: Enzymatic properties of a purified recombinant fusion protein containing NADPH-P450 reductase. Proc. Natl Acad. Sci. USA 1993; 90: 11748-52.
24. Gillam EMJ, Guo Z, Ueng Y-F et al. Expression of cytochrome P450 3A5 in Escherichia coli: Effects of 5′ modifications, purification, spectral characterization, reconstitution conditions, and catalytic activities. Arch. Biochem. Biophys. 1995; 317: 374-84.
25. Gillam EMJ, Ueng Y-F, Wunsch RM, Shimada T, Kamataki T, Guengerich FP. Expression of cytochrome P450 3A7 in Escherichia coli: Effects of 5′ modification and catalytic characterization of recombinant enzyme expressed in bicistronic format with NADPH-cytochrome P450 reductase. Arch. Biochem. Biophys. 1997; 346: 81-90.
26. Eliasson E, Johansson I, Ingelman-Sundberg M. Substrate-, hormone-, and cAMP-regulated cytochrome P450 degradation. Proc. Natl Acad. Sci. USA 1990; 87: 3225-9.
27. Freeman JE, Wolf CR. Evidence against a role for serine 129 in determining murine cytochrome P450 Cyp2e-1 protein levels. Biochemistry 1994; 33: 13963-6.
28. Eliasson E, Mkrtchian S, Halpert JR, Ingelman-Sundberg M. Substrate regulated cAMP-dependent phosphorylation, denaturation, and degradation of glucocorticoid-inducible rat liver cytochrome P450 3A1. J. Biol. Chem. 1994; 269: 18378-83.
29. 2-terminal membrane-insertion signal peptide does not alter the catalytic activities. Proc. Natl Acad. Sci. USA 1991; 88: 9141-5.
30. 2-terminal segment retains catalytic activity and is membrane-bound when expressed in Escherichia coli. J. Biol. Chem. 1991; 266: 7321-4.
31. Li YC, Chiang JYL. The expression of a catalytically active cholesterol 7a-hydroxylase cytochrome P-450 in Escherichia coli. J. Biol. Chem. 1991; 266: 19186-91.
32. Barnes HJ, Arlotto MP, Waterman MR. Expression and enzymatic activity of recombinant cytochrome P450 17α-hydroxylase in Escherichia coli. Proc. Natl Acad. Sci. USA 1991; 88: 5597-601.
33. Looman AC, Bodlaender J, Comstock LJ et al. Influence of the codon following the AUG initiation codon on the expression of a modified lacZ gene in Escherichia coli. EMBO J. 1987; 6: 2489-92.
34. 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. USA 1992; 89: 10817-21.
35. Fisher CW, Shet M, Caudle DL, Martin-Wixtrom C, Estabrook RW. Expression of human cytochrome P450s in E. coli. In: Fourth European ISSX Meeting. 3-6 July, 1992, Bologna, Italy. Bethesda: International Society for the study of Xenobiotics. 1992; I: 106 (Abstract).
36. Sandhu P, Guo Z, Baba T, Martin MV, Tukey RH, Guengerich FP. Expression of modified human cytochrome P450 1A2 in Escherichia coli: Stabilization, purification, spectral characterization, and catalytic activities of the enzyme. Arch. Biochem. Biophys. 1994; 309: 168-77.
37. Richardson TH, Hsu MH, Kronbach T et al. Purification and characterization of recombinant-expressed cytochrome P450 2C3 from Escherichia coli: 2C3 encodes the 6β-hydroxylase deficient form of P450 3b. Arch. Biochem. Biophys. 1993; 300: 510-16.
38. John GH, Hasler JA, He Y, Halpert JR. Escherichia coli expression and characterization of cytochromes P450 2B11, 2B1, and 2B5. Arch. Biochem. Biophys. 1994; 314: 367-75.
39. TYR expressed at high levels in Escherichia coli. Arch. Biochem. Biophys. 1995; 322: 369-77.
40. Winters DK, Cederbaum AI. Expression of a catalytically active human cytochrome P-4502E1 in Escherichia coli. Biochim. Biophys. Acta 1992; 1156: 43-9.
41. Nishimoto M, Clark JE, Masters BSS. Cytochrome P450 4A4 expression in Escherichia coli, purification, and characterization of catalytic properties. Biochemistry 1993; 32: 8863-70.
42. 2+-chelate affinity purification, and characterization of solubility and aggregation. Arch. Biochem. Biophys. 1995; 321: 277-88.
43. Sueyoshi T, Park LJ, Moore R, Juvonen RO, Negishi M. Molecular engineering of microsomal P450 2a-4 to a stable, water-soluble enzyme. Arch. Biochem. Biophys. 1995; 322: 265-71.
44. Pritchard MP, Ossetian R, Li DN et al. General strategy for the expression of recombinant human cytochrome P450s in Escherichia coli using bacterial signal peptides. Expression of CYP3A4, CYP2A6, CYP2E1. Arch. Biochem. Biophys. 1997; 345: 342-54.
45. Peterson JA, Graham-Lorence SE. Bacterial P450s. Structural similarities and functional differences. In: Ortiz de Montellano PR (ed.). Cytochrome P450. Structure, Mechanism and Biochemistry. Plenum Press, New York. 1995; 151-80.
46. Bauer S, Shiloach J. Maximal exponential growth rate and yield of E. coli obtainable in a bench-scale fermentor. Biotechnol. Bioeng. 1974; 16: 933-41.
47. Woodard SI, Dailey HA. Regulation of heme biosynthesis in Escherichia coli. Arch. Biochem. Biophys. 1995; 316: 110-15.
48. Kery V, Elleder D, Kraus JP. δ-Aminolevulinate increases heme saturation and yield of human cystathionine β-synthase expressed in Escherichia coli. Arch. Biochem. Biophys. 1995; 316: 24-9.
49. Springer BA, Sligar SG. High-level expression of sperm whale myoglobin in Escherichia coli. Proc. Natl Acad. Sci. USA 1987; 84: 8961-5.
50. Karam WG, Chiang JYL. Polymorphisms of human cholesterol 7α-hydroxylase. Biochem. Biophys. Res. Commun. 1992; 185: 588-95.
51. Guengerich FP, Martin MV, Guo Z, Chun Y-J. Purification of recombinant human cytochrome P450 enzymes expressed in bacteria. Methods Enzymol. 1996; 272: 35-44.
52. Wrighton SA, Brian WR, Sari MA et al. Studies on the expression and metabolic capabilities of human liver cytochrome P450IIIA5 (HLp3). Mol. Pharmacol. 1990; 38: 207-13.
53. Imaoka S, Imai Y, Shimada T, Funae Y. Role of phospholipids in reconstituted cytochrome P450 3A forms and mechanism of their activation of catalytic activity. Biochemistry 1992; 31: 6063-9.
54. Yamazaki H, Johnson WW, Ueng YF, Shimada T, Guengerich FP. Lack of electron transfer from cytochrome b (5) in stimulation of catalytic activities of cytochrome P450 3A4: Characterization of a reconstituted cytochrome P450 3A4 NADPH-cytochrome P450 reductase system and studies with apo-cytochrome b (5). J. Biol. Chem. 1996; 271: 27438-44.
55. Yamazaki H, Gillam EMJ, Dong M-S, Johnson WW, Guengerich FP, Shimada T. Reconstitution of recombinant cytochrome P450 2C10 (2C9) and comparison with cytochrome P450 3A4 and other forms: Effects of cytochrome P450-P450 and cytochrome P450-b5 interactions. Arch. Biochem. Biophys. 1997; 342: 329-37.
56. Fisher CW, Shet MS, Martin-Wixtrom C, Estabrook RW. High-level expression in Escherichia coli of enzymatically active fusion proteins containing the domains of cytochromes P450 and NADPH-P450 reductase flavoprotein. Proc. Natl Acad. Sci. USA 1992; 89: 10817-21.
57. Chun Y-J, Shimada T, Guengerich FP. Construction of a human cytochrome P450 1A1:rat NADPH-P450 reductase fusion protein cDNA, expression in Escherichia coli, purification, and catalytic properties of the enzyme in bacterial cells and alter purification. Arch. Biochem. Biophys. 1996; 330: 48-58.
58. Parikh A, Guengerich FP. Expression, purification, and characterization of a catalytically active human cytochrome P450 1A2-rat NADPH-cytochrome P450 reductase fusion protein. Protein Express. Purif. 1997; 9: 346-54.
59. Murakami H, Yabusaki Y, Sakaki T, Shibata M, Ohkawa HA. Genetically engineered P450 monooxygenase: Construction of the functional fused enzyme between rat cytochrome P450c and NADPH-cytochrome P450 reductase. DNA 1987; 6: 189-97.
60. 5, NADPH-P450 reductase, and lipid on the rate of 6β-hydroxylation of testosterone as catalyzed by a human P450 3A4 fusion protein. Arch. Biochem. Biophys. 1995; 318: 314-21.
61. Dong J, Porter TD. Coexpression of mammalian cytochrome P450 and reductase in Escherichia coli. Arch. Biochem. Biophys. 1997; 327: 254-9.
62. Blake JAR, Pritchard M, Ding S et al. Coexpression of a human P450 (CYP3A4) and P450 reductase generated a highly functional monooxygenase system in Escherichia coli. FEBS Lett. 1996; 397: 210-14.
63. Shet MS, Fisher CW, Estabrook RW. The function of recombinant cytochrome P450s in intact Escherichia coli cells: The 17-α-hydroxylation of progesterone and pregnenolone by P450C17. Arch. Biochem. Biophys. 1997; 339: 218-25.
64. Parikh A, Gillam EMJ, Guengerich FP. Bacterial catalysis of reactions important in mammalian drug and xenobiotic metabolism: Functional co-expression of six human microsomal cytochrome P450 enzymes with NADPH-cytochrome P450 reductase in Escherichia coli. Nature Biotech. 1997: 15: 784-8.
65. Shaw PM, Hosea NA, Thompson DV, Lenius JM, Guengerich FP. Reconstitution premixes for assays using purified recombinant human cytochrome P450 NADPH-cytochrome P450 reductase, and cytochrome b (5). Arch. Biochem. Biophys. 1997; 348: 107-15.
66. Styles JA, Davies A, Lim CK et al. Genotoxicity of tamoxifen, tamoxifen epoxide and toremifene in human lymphoblastoid cells containing human cytochrome P450s. Carcinogenesis 1994; 15: 5-9.
67. Josephy PD, Gruz P, Nohmi T. Recent advances in the construction of bacterial genotoxicity assays. Mutation Res. 1997; 386: 1-23.
68. Josephy PD, DeBruin LS, Lord HL et al. Bioactivation of aromatic amines by recombinant human cytochrome P450 1A2 expressed in bacteria: A substitute for mammalian tissue preparations in mutagenicity testing. Cancer Res. 1995; 55: 799-802.
69. Josephy PD, Evans DH, Parikh A, Guengerich FP. Metabolic activation of aromatic amine mutagens by simultaneous expression of human cytochrome P450 1A2, NADPH-cytochrome P450 reductase, and N-acetyltransferase in Escherichia coli. Chem. Res. Toxicol. 1998; 11: 70-4.
70. Jenkins CM, Waterman MR. Flavodoxin and NADP-flavodoxin reductase from Escherichia coli support bovine cytochrome P450c17 hydroxylase activities. J. Biol. Chem. 1994; 269: 27401-8.
71. Gautier J-C, Urban P, Beaune P, Pompon D. Engineered yeast cells as a model to study coupling human xenobiotic metabolizing enzymes. Simulation of the two first steps of benzo[a]pyrene activation. Eur. J. Biochem. 1993; 211: 63-72.
72. Estabrook RW, Shet MS, Faulkner K, Fisher CW. The use of electrochemistry for the synthesis if 17-alpha-hydroxyprogesterone by a fusion protein containing P450C17. Endocr. Res. 1996; 22: 665-71.
73. Hayes CR, Spink DC, Spink BC, Cao JQ, Walker NJ, Sutter TR. 17β-Estradiol hydroxylation catalysed by human cytochrome P450 1B1. Proc. Natl Acad. Sci. USA 1996; 93: 9776-81.
74. Munns AJ, DeVoss JJ, Dickinson RG, Hooper WD, Gillam EMJ. Bioactivation of phenytoin by human cytochrome P450: Characterization of the mechanism and targets of covalent adduct formation. Chem. Res. Toxicol. 1997; 10: 1049-58.