Extending the capabilities of nature's most versatile catalysts: Directed evolution of mammalian xenobiotic-metabolizing P450s

Archives of Biochemistry and Biophysics

Volumn 464, Issue 2, 2007, Pages 176-186

  Gillam, Elizabeth M J ^a  

^a UNIVERSITY OF QUEENSLAND   (Australia)

Author keywords

Biocatalysis; Cytochrome P450; Directed evolution; DNA shuffling; Indole

Indexed keywords

ALIPHATIC COMPOUND; AROMATIC COMPOUND; CYTOCHROME P450; DRUG METABOLIZING ENZYME; ENVIRONMENTAL CHEMICAL; LIVER ENZYME; ORGANIC COMPOUND; OXYGEN 15; UNSPECIFIC MONOOXYGENASE; XENOBIOTIC AGENT;

CATALYST; CHEMICAL MODIFICATION; DIRECTED MOLECULAR EVOLUTION; DRUG METABOLISM; ENZYME ACTIVITY; ENZYME CONFORMATION; ENZYME ENGINEERING; ENZYME SUBSTRATE; ENZYME SUBSTRATE COMPLEX; LIVER METABOLISM; MAMMAL; NONHUMAN; PRIORITY JOURNAL; SHORT SURVEY; XENOBIOTIC METABOLISM;

CATALYSIS; CYTOCHROME P-450 ENZYME SYSTEM; DIRECTED MOLECULAR EVOLUTION; DRUG DESIGN; PROTEIN ENGINEERING; XENOBIOTICS;

MAMMALIA;

EID: 34547690799     PISSN: 00039861     EISSN: 10960384     Source Type: Journal    
DOI: 10.1016/j.abb.2007.04.033     Document Type: Short Survey

References (91)

1. Newcomb M., Hollenberg P.F., and Coon M.J. Arch. Biochem. Biophys. 409 (2003) 72-79
2. D.R. Nelson (2007). Available from: .
3. Capdevila J., Holla V.R., and Falck J.R. Cytochrome P450 and the metabolism and bioactivation of arachidonic acid and eicosanoids. In: Montellano P.R. (Ed). Cytochrome P450. Structure, Mechanism, and Biochemistry (2005), Kluwer Academic/Plenum Publishing, New York 531-551
4. Kelly S.L., Kelly D.E., Jackson C.J., Warrilow A.G.S., and Lamb D.C. The diversity and importance of microbial cytochromes P450. In: Ortiz de Montellano P.R. (Ed). Cytochrome P450, Structure, Mechanism, and Biochemistry (2005), Kluwer Academic/Plenum Publishing, New York 585-617
5. Morant M., Bak S., Moller B.L., and Werck-Reichhart D. Curr. Opin. Biotech. 14 (2003) 151-162
6. Isin E.M., and Guengerich F.P. Biochim. Biophys. Acta 1770 (2007) 314-329
7. Guengerich F.P. Human cytochrome P450 enzymes. In: Ortiz de Montellano P.R. (Ed). Cytochrome P450 (2005), Kluwer Academic/Plenum Publishing, New York 377-530
8. Wang P., Mason P.S., and Guengerich F.P. Arch. Biochem. Biophys. 199 (1980) 206-219
9. Wang P.P., Beaune P., Kaminsky L.S., Dannan G.A., Kadlubar F.F., Larrey D., and Guengerich F.P. Biochemistry 22 (1983) 5375-5383
10. Distlerath L.M., Reilly P.E.B., Martin M.V., Davis G.G., Wilkinson G.R., and Guengerich F.P. J. Biol. Chem. 260 (1985) 9057-9067
11. Shimada T., Misono K.S., and Guengerich F.P. J. Biol. Chem. 261 (1986) 909-921
12. Yun C.-H., Shimada T., and Guengerich F.P. Mol. Pharmacol. 40 (1991) 679-685
13. Patten P.A., Howard R.I., and Stemmer W.P.C. Curr. Opin. Biotech. 8 (1997) 724-733
14. Cherry J.R., and Fidantsef A.L. Curr. Opin. Biotech. 14 (2003) 438-443
15. Cohen N., Abramov S., Dror Y., and Freeman A. Trends Biotech. 19 (2001) 507-510
16. Kumar S., Chen C.S., Waxman D.J., and Halpert J.R. J. Biol. Chem. 280 (2005) 19569-19575
17. Kim D., and Guengerich F.P. Biochemistry 43 (2004) 981-988
18. Pompon D., Gautier J.C., Perret A., Truan G., and Urban P. J. Hepatol. 26 (1997) 81-85
19. Brian W.R., Sari M.-A., Iwasaki M., Shimada T., Kaminsky L.S., and Guengerich F.P. Biochemistry 29 (1990) 11280-11292
20. Peyronneau M.A., Renaud J.P., Truan G., Urban P., Pompon D., and Mansuy D. Eur. J. Biochem. 207 (1992) 109-116
21. Abécassis V., Pompon D., and Truan G. Nucleic Acids Res. 28 (2000) e88-1-e88-10
22. Williams P.A., Cosme J., Sridhar V., Johnson E.F., and McRee D.E. Mol. Cell 5 (2000) 121-131
23. Scott E.E., He Y.A., Wester M.R., White M.A., Chin C.C., Halpert J.R., Johnson E.F., and Stout C.D. Proc. Natl. Acad. Sci. USA 100 (2003) 13121-13126
24. Schoch G.A., Yano J.K., Wester M.R., Griffin K.J., Stout C.D., and Johnson E.F. J. Biol. Chem. 279 (2004) 9497-9503
25. Wester M.R., Yano J.K., Schoch G.A., Yang C., Griffin K.J., Stout C.D., and Johnson E.F. J. Biol. Chem. 279 (2004) 35630-35637
26. Yano J.K., Wester M.R., Schoch G.A., Griffin K.J., Stout C.D., and Johnson E.F. J. Biol. Chem. 279 (2004) 38091-38094
27. Yano J.K., Hsu M.H., Griffin K.J., Stout C.D., and Johnson E.F. Nat. Struct. Mol. Biol. 12 (2005) 822-823
28. B.D. Smith, J.L. Sanders, P.R. Porubsky, G.H. Lushington, C.D. Stout, E.E. Scott, J. Biol. Chem., in press.
29. Sansen S., Yano J.K., Reynald R.L., Schoch G.A., Griffin K.J., Stout C.D., and Johnson E.F. J. Biol. Chem. 282 (2007) 14348-14355
30. Williams P.A., Cosme J., Ward A., Angove H.C., Vinkovic D.M., and Jhoti H. Nature 424 (2003) 464-468
31. Williams P.A., Cosme J., Vinkovi D.M., Ward A., Angove H.C., Day P.J., Vonrhein C., Tickle I.J., and Jhoti H. Science 305 (2004) 683-686
32. Rowland P., Blaney F.E., Smyth M.G., Jones J.J., Leydon V.R., Oxbrow A.K., Lewis C.J., Tennant M.G., Modi S., Eggleston D.S., Chenery R.J., and Bridges A.M. J. Biol. Chem. 281 (2006) 7614-7622
33. Barnes H.J., Arlotto M.P., and Waterman M.R. Proc. Natl. Acad. Sci. USA 88 (1991) 5597-5601
34. Lamb D.C., Kelly D.E., Masaphy S., Jones G.L., and Kelly S.L. Biochem. Biophys. Res. Commun. 276 (2000) 797-802
35. Kaderbhai M.A., Ugochukwu C.C., Lamb D.C., and Kelly S.L. Biochem. Biophys. Res. Commun. 279 (2000) 803-807
36. Lentz O., Qing-Shang L.I., Schwaneberg U., Lutz-Wahl S., Fischer P., and Schmid R.D. J. Mol. Catal. B Enzym. 15 (2001) 123-133
37. Stemmer W.P.C. Nature 370 (1994) 389-391
38. Cirino P.C., Mayer K.M., and Umeno D. Generating mutant libraries using error-prone PCR. In: Arnold F.H., and Georgiou G. (Eds). Directed Evolution Library Creation: Methods and Protocols (2003), Humana Press, Totowa, NJ 3-9
39. Wong T.S., Zhurina D., and Schwaneberg U. Comb. Chem. High Throughput Screen. 9 (2006) 271-288
40. Miyazaki K., and Arnold F.H. J. Mol. Evol. 49 (1999) 716-720
41. Georgescu R., Bandara G., Sun L., and Mutagenesis S. Directed Evolution Library Creation: Methods and Protocols. In: Arnold F.H., and Georgiou G. (Eds) (2003), Humana Press, Totowa, NJ 75-83
42. Wong T.S., Tee K.L., Hauer B., and Schwaneberg U. Nucleic Acids Res. 32 (2004) e26
43. Drummond D.A., Iverson B.L., Georgiou G., and Arnold F.H. J. Mol. Biol. 350 (2005) 806-816
44. Crameri A., Raillard S.A., Bermudez E., and Stemmer W.P.C. Nature 391 (1998) 288-291
45. W. Huang, W.A. Johnston, M.A. Hayes, J.J. De Voss, E.M.J. Gillam, A shuffled CYP2C library with a high degree of structural integrity and functional versatility, submitted for publication.
46. W.A. Johnston, W. Huang, M.A. Hayes, J.J. De Voss, E.M.J. Gillam, Creation and screening of a diversely functional library from CYP1A1 and CYP1A2 using DNA family shuffling, submitted for publication.
47. Zhao H., Giver L., Shao Z., Affholter J.A., and Arnold F.H. Nat. Biotech. 16 (1998) 258-261
48. Sieber V., Martinez C.A., and Arnold F.H. Nat. Biotech. 19 (2001) 456-460
49. Coco W.M., Levinson W.E., Crist M.J., Hektor H.J., Darzins A., Pienkos P.T., Squires C.H., and Monticello D.J. Nat. Biotech. 19 (2001) 354-359
50. Ostermeier M., Shim J.H., and Benkovic S.J. Nat. Biotech. 17 (1999) 1205-1209
51. Voigt C.A., Martinez C., Wang Z.-G., Mayo S.L., and Arnold F.H. Nat. Struct. Biol. 9 (2002) 553-558
52. Hiraga K., and Arnold F.H. J. Mol. Biol. 330 (2003) 287-296
53. Kumar S., Liu H., and Halpert J.R. Drug Metab. Dispos. 34 (2006) 1958-1965
54. Otey C.R. High-throughput carbon monoxide binding assay for cytochromes P450. In: Arnold F.H., and Georgiou G. (Eds). Methods Mol. Biol (2003), Humana Press Inc.,, Totowa, NJ 137-139
55. W.A. Johnston, W. Huang, M.A. Hayes, J.J. De Voss, E.M.J. Gillam, Quantitative whole cell assays for cytochrome P450 with high throughput application, submitted for publication.
56. Abécassis V., Urban P., Aggerbeck L., Truan G., and Pompon D. Biocat. Biotrans. 21 (2003) 55-66
57. Kim D., and Guengerich F.P. Arch. Biochem. Biophys. 432 (2004) 102-108
58. Kim D., Wu Z.L., and Guengerich F.P. J. Biol. Chem. 280 (2005) 40319-40327
59. Joo H., Lin Z., and Arnold F.H. Nature 399 (1999) 670-673
60. Kumar S., Sun L., Liu H., Muralidhara B.K., and Halpert J.R. Protein Eng. Des. Sel. 19 (2006) 547-554
61. Gillam E.M.J., Aguinaldo A.M.A., Notley L.M., Kim D., Mundkowski R.G., Volkov A.A., Arnold F.H., Soucek P., DeVoss J.J., and Guengerich F.P. Biochem. Biophys. Res. Commun. 265 (1999) 469-472
62. Gillam E.M.J., Notley L.M., Cai H.L., De Voss J.J., and Guengerich F.P. Biochemistry 39 (2000) 13817-13824
63. Nakamura K., Martin M.V., and Guengerich F.P. Arch. Biochem. Biophys. 395 (2001) 25-31
64. Wu Z.L., Podust L.M., and Guengerich F.P. J. Biol. Chem. 280 (2005) 41090-41100
65. Winters D.K., and Cederbaum A.I. Biochim. Biophys. Acta 1156 (1992) 43-49
66. Peters M.W., Meinhold P., Glieder A., and Arnold F.H. J. Am. Chem. Soc. 125 (2003) 13442-13450
67. Otey C.R., and Joern J.M. Methods Mol. Biol. 230 (2003) 141-148
68. Cali J.J., Ma D., Sobol M., Simpson D.J., Frackman S., Good T.D., Daily W.J., and Liu D. Expert Opin. Drug Metab. Toxicol. 2 (2006) 629-645
69. Parikh M.R., and Matsumura I. J. Mol. Biol. 352 (2005) 621-628
70. Naglak T.J., Hettwer D.J., and Wang H.Y. Process Biotech. 9 (1990) 177-205
71. Tsotsou G.E., Cass A.E.G., and Gilardi G. Biosens. Bioelect. 17 (2002) 119-131
72. Gonchar M.V., Maidan M.M., Moroz O.M., Woodward J.R., and Sibirny A.A. Biosens. Bioelect. 13 (1998) 945-952
73. Parikh A., Josephy P.D., and Guengerich F.P. Biochemistry 38 (1999) 5283-5289
74. Gotoh O. J. Biol. Chem. 267 (1992) 83-90
75. Wu Z.-L., Aryal P., Lozach O., Meijer L., and Guengerich F.P. Chem. Biodiversity 2 (2005) 51-65
76. Warzecha H., Frank A., Peer M., Gillam E.M.J., Guengerich F.P., and Unger M. Plant Biotech. J. 5 (2007) 185-191
77. Sun L., Chen C.S., Waxman D.J., Liu H., Halpert J.R., and Kumar S. Arch. Biochem. Biophys. 458 (2007) 167-174
78. Taly V., Urban P., Truan G., and Pompon D. Biochim. Biophys. Acta 1770 (2007) 446-457
79. Pompon D., and Nicolas A. Gene 83 (1989) 15-24
80. Faulkner K.M., Shet M.S., Fisher C.W., and Estabrook R.W. Proc. Natl. Acad. Sci. USA 92 (1995) 7705-7709
81. Shumyantseva V.V., Bulko T.V., Bachmann T.T., Bilitewski U., Schmid R.D., and Archakov A.I. Arch. Biochem. Biophys. 377 (2000) 43-48
82. Joseph S., Rusling J.F., Lvov Y.M., Friedberg T., and Fuhr U. Biochem. Pharmacol. 65 (2003) 1817-1826
83. Straathof A.J.J., Panke S., and Schmid A. Curr. Opin. Biotech. 13 (2002) 548-556
84. Fisher C.W., Shet M.S., Martin-Wixtrom C., and Estabrook R.W. Proc. Natl. Acad. Sci. USA 89 (1992) 10817-10821
85. Shet M.S., Fisher C.W., Arlotto M.P., Shackleton C.H.L., Holmans P.L., Martin-Wixtrom C.A., Saeki Y., and Estabrook R.W. Arch. Biochem. Biophys. 311 (1994) 402-417
86. Deeni Y.Y., Paine M.J.I., Ayrton A.D., Clarke S.E., Chenery R., and Wolf C.R. Arch. Biochem. Biophys. 396 (2001) 16-24
87. Fairhead M., Giannini S., Gillam E.M., and Gilardi G. J. Biol. Inorg. Chem. 10 (2005) 842-853
88. Jenkins C.M., and Waterman M.R. J. Biol. Chem. 269 (1994) 27401-27408
89. Atkins W.M. Annu. Rev. Pharmacol. Toxicol. 45 (2005) 291-310
90. Daugulis A.J. Trends Biotech. 19 (2001) 457-462
91. You L., and Arnold F.H. Protein Eng. 9 (1994) 77-83