Mammalian Epoxide Hydrolases

Comprehensive Toxicology, Second Edition

Volumn 4, Issue , 2010, Pages 275-294

  Marowsky, A ^a   Cronin, A ^a   Frere F ^a   Adamska, M ^a   Arand, M ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

? ? hydrolase fold; Aflatoxin B1; Butadiene; Detoxication; Electrophile; Epoxyeicosatrienoic acid; Lipid signaling; Mechanism; Polycyclic aromatic hydrocarbon; Styrene

Indexed keywords

EID: 85012842465     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1016/B978-0-08-046884-6.00415-2     Document Type: Chapter

References (141)

1. Arand M., Cronin A., Adamska M., Oesch F. Methods Enzymol. 2005, 400:569-588.
2. Arand M., Cronin A., Oesch F., Mowbray S.L., Jones T.A. Drug Metab. Rev. 2003, 35:365-383.
3. Arand M., Grant D.F., Beetham J.K., Friedberg T., Oesch F., Hammock B.D. FEBS Lett. 1994, 338:251-256.
4. Arand M., Hallberg B.M., Zou J.Y., Bergfors T., Oesch F., Van Der Werf M.J., De Bont J.A.M., Jones T.A., Mowbray S.L. EMBO J. 2003, 22:2583-2592.
5. Arand M., Hemmer H., Dürk H., Baratti J., Archelas A., Furstoss R., Oesch F. Biochem. J. 1999, 344:273-280.
6. Arand M., Herrero Plana M.E., Hengstler J.G., Lohmann M., Cronin A., Oesch F. EXCLI J. 2003, 2:22-30.
7. Arand M., Knehr M., Thomas H., Zeller H.D., Oesch F. FEBS Lett. 1991, 294:19-22.
8. Arand M., Müller F., Mecky A., Hinz W., Urban P., Pompon D., Kellner R., Oesch F. Biochem. J. 1999, 337:37-43.
9. Arand M., Wagner H., Oesch F. J. Biol. Chem. 1996, 271:4223-4229.
10. Argiriadi M.A., Morisseau C., Hammock B.D., Christianson D.W. Proc. Natl. Acad. Sci. USA 1999, 96:10637-10642.
11. Bauer A.K., Faiola B., Abernethy D.J., Marchan R., Pluta L.J., Wong V.A., Gonzalez F.J., Butterworth B.E., Borghoff S.J., Everitt J.I., et al. Toxicol. Sci. 2003, 72:201-209.
12. Beetham J.K., Grant D., Arand M., Garbarino J., Kiyosue T., Pinot F., Oesch F., Belknap W.R., Shinozaki K., Hammock B.D. DNA Cell Biol. 1995, 14:61-71.
13. Beetham J.K., Tian T.G., Hammock B.D. Arch. Biochem. Biophys. 1993, 305:197-201.
14. Bell P.A., Kasper C.B. J. Biol. Chem. 1993, 268:14011-14017.
15. Benhamou S., Reinikainen M., Bouchardy C., Dayer P., Hirvonen A. Cancer Res. 1998, 58:5291-5293.
16. Bentley P., Schmassmann H., Sims P., Oesch F. Eur. J. Biochem. 1976, 69:97-103.
17. Black H.S., Lenger W.A. Anal. Biochem. 1979, 94:383-385.
18. Breuer H., Knuppen R. Biochim. Biophys. Acta 1961, 49:620-621.
19. Chen J.K., Capdevila J., Harris R.C. Mol. Cell. Biol. 2001, 21:6322-6331.
20. Cronin A., Homburg S., Durk H., Richter I., Adamska M., Frere F., Arand M. J. Mol. Biol. 2008, 383:627-640.
21. Cronin A., Mowbray S., Dürk H., Homburg S., Fleming I., Fisslthaler B., Oesch F., Arand M. Proc. Natl. Acad. Sci. USA 2003, 100:1552-1557.
22. Csanady G.A., Kessler W., Hoffmann H.D., Filser J.G. Toxicol Lett. 2003, 138:75-102.
23. Dorrance A.M., Rupp N., Pollock D.M., Newman J.W., Hammock B.D., Imig J.D. J. Cardiovasc. Pharmacol. 2005, 46:842-848.
24. Decker M., Arand M., Cronin A. Arch. Toxicol. 2009, 83:297-318.
25. Elfstrom L.T., Widersten M. Biochemistry (Mosc) 2006, 45:205-212.
26. Enayetallah A.E., French R.A., Barber M., Grant D.F. J. Histochem. Cytochem. 2006, 54:329-335.
27. Enayetallah A.E., Grant D.F. Biochem. Biophys. Res. Commun. 2006, 341:254-260.
28. Falany C.N., Mcquiddy P., Kasper C.B. J. Biol. Chem. 1987, 262:5924-5930.
29. Fillgrove K.L., Pakhomova S., Schaab M.R., Newcomer M.E., Armstrong R.N. Biochemistry (Mosc) 2007, 46:8110-8120.
30. Fisslthaler B., Popp R., Kiss L., Potente M., Harder D.R., Fleming I., Busse R. Nature 1999, 401:493-497.
31. Fornage M., Boerwinkle E., Doris P.A., Jacobs D., Liu K., Wong N.D. Circulation 2004, 109:335-339.
32. Forrest A.R.R., Ravasi T., Taylor D., Huber T., Hume D.A., Grimmond S., Grp R.G., Members G. Genome Res. 2003, 13:1443-1454.
33. Franken S.M., Rozeboom H.J., Kalk K.H., Dijkstra B.W. EMBO J. 1991, 10:1297-1302.
34. Friedberg T., Löllmann B., Becker R., Holler R., Oesch F. Biochem. J. 1994, 303:967-972.
35. Gaedigk A., Leeder J.S., Grant D.M. DNA Cell Biol. 1997, 16:1257-1266.
36. Gomez G.A., Morisseau C., Hammock B.D., Christianson D.W. Biochemistry (Mosc) 2004, 43:4716-4723.
37. Grant D.F., Storms D.H., Hammock B.D. J. Biol. Chem. 1993, 268:17628-17633.
38. Gschwendtner A., Ripke S., Freilinger T., Lichtner P., Müller-Myhsok B., Wichmann H.-E., Meitinger T., Dichgans M. Stroke 2008, 39:1593-1596.
39. Haeggstrom J.Z. J. Biol. Chem. 2004, 279:50639-50642.
40. Hammock B.D., Gill S.S., Stamoudis V., Gilbert L.I. Comp. Biochem. Physiol. B Biochem. Mol. Biol. 1976, 53:263-265.
41. Hammock B.D., Pinot F., Beetham J.K., Grant D.F., Arand M.E., Oesch F. Biochem. Biophys. Res. Commun. 1994, 198:850-856.
42. Harris T.R., Aronov P.A., Jones P.D., Tanaka H., Arand M., Hammock B.D. Arch. Biochem. Biophys. 2008, 472(2):139-149.
43. Hasegawa L.S., Hammock B.D. Biochem. Pharmacol. 1982, 31:1979-1984.
44. Hassett C., Aicher L., Sidhu J.S., Omiecinski C.J. Hum. Mol. Genet. 1994, 3:421-428.
45. Hennebold J.D., Mah K., Perez W., Vance J.E., Stouffer R.L., Morisseau C., Hammock B.D., Adashi E.Y. Biol. Reprod. 2005, 72:968-975.
46. Herrero M.E., Arand M., Hengstler J.G., Oesch F. Environ. Mol. Mutagen. 1997, 30:429-439.
47. Holder G., Yagi H., Dansette P., Jerina D.M., Levin W., Lu A.Y.H., Conney A.H. Proc. Natl. Acad. Sci. USA 1974, 71:4356-4360.
48. Holler R., Arand M., Mecky A., Oesch F., Friedberg T. Biochem. Biophys. Res. Commun. 1997, 236:754-759.
49. Holmquist M. Curr. Protein Pept. Sci. 2000, 1:209-235.
50. Honscha W., Oesch F., Friedberg T. Arch. Biochem. Biophys. 1991, 287:380-385.
51. Hwang S.H., Tsai H.J., Liu J.Y., Morisseau C., Hammock B.D. J. Med. Chem. 2007, 50:3825-3840.
52. Imig J.D., Zhao X.Y., Zaharis C.Z., Olearczyk J.J., Pollock D.M., Newman J.W., Kim I.H., Watanabe T., Hammock B.D. Hypertension 2005, 46:975-981.
53. Inceoglu B., Jinks S.L., Schmelzer K.R., Waite T., Kim I.H., Hammock B.D. Life Sci. 2006, 79:2311-2319.
54. Johansson P., Unge T., Cronin A., Arand M., Bergfors T., Jones T.A., Mowbray S.L. J. Mol. Biol. 2005, 351:1048-1056.
55. Johnson W.W., Yamazaki H., Shimada T., Ueng Y.F., Guengerich F.P. Chem. Res. Toxicol. 1997, 10:672-676.
56. Jourenkova-Mironova N., Mitrunen K., Bouchardy C., Dayer P., Benhamou S., Hirvonen A. Cancer Res. 2000, 60:534-536.
57. Kanekoishino T., Kuroiwa Y., Miyoshi N., Kohda T., Suzuki R., Yokoyama M., Viville S., Barton S.C., Ishino F., Surani M.A. Nat. Genet. 1995, 11:52-59.
58. Kelly E.J., Erickson K.E., Sengstag C., Eaton D.L. Toxicol. Sci. 2002, 65:35-42.
59. Kim I.H., Tsai H.J., Nishi K., Kasagami T., Morisseau C., Hammock B.D. J. Med. Chem. 2007, 50:5217-5226.
60. Knehr M., Thomas H., Arand M., Gebel T., Zeller H.D., Oesch F. J. Biol. Chem. 1993, 268:17623-17627.
61. Koonin E.V., Tatusov R.L. J. Mol. Biol. 1994, 244:125-132.
62. Kreuzer P.E., Kessler W., Welter H.F., Baur C., Filser J.G. Arch. Toxicol. 1991, 65:59-67.
63. Krämer A., Pudil J., Frank H., Oesch F., Glatt H. Mutat. Res. 1993, 290:165-174.
64. Kwak M.K., Itoh K., Yamamoto M., Sutter T.R., Kensler T.W. Mol. Med. 2001, 7:135-145.
65. Lacourciere G.M., Armstrong R.N. J. Am. Chem. Soc. 1993, 115:10466-10467.
66. Lacourciere G.M., Armstrong R.N. Chem. Res. Toxicol. 1994, 7:121-124.
67. Laughlin L.T., Tzeng H.F., Lin S., Armstrong R.N. Biochemistry (Mosc) 1998, 37:2897-2904.
68. Laurenzana E.M., Hassett C., Omiecinski C.J. Pharmacogenetics 1998, 8:157-167.
69. Lee C.R., North K.E., Bray M.S., Fornage M., Seubert J.M., Newman J.W., Hammock B.D., Couper D.J., Heiss G., Zeldin D.C. Hum. Mol. Genet. 2006, 15:1640-1649.
70. Levin W., Wood A.W., Yagi H., Dansette P.M., Jerina D.M., Conney A.H. Proc. Natl. Acad. Sci. USA 1976, 73:243-247.
71. Li P.L., Campbell W.B. Circ. Res. 1997, 80:877-884.
72. Li P.L., Chen C.L., Bortell R., Campbell W.B. Circ. Res. 1999, 85:349-356.
73. Liang S.H., Hassett C., Omiecinski C.J. Mol. Pharmacol. 2005, 67:220-230.
74. Loch D., Hoey A., Morisseau C., Hammock B.O., Brown L. Cell Biochem. Biophys. 2007, 47:87-97.
75. Luria A., Weldon S.M., Kabcenell A.K., Ingraham R.H., Matera D., Jiang H.P., Gill R., Morisseau C., Newman J.W., Hammock B.D. J. Biol. Chem. 2007, 282:2891-2898.
76. Marowsky A., Burgener J., Falck J.R., Fritschy J.M., Arand M. Neuroscience 2009, 163:646-661.
77. Mcglynn K.A., Rosvold E.A., Lustbader E.D., Hu Y., Clapper M.L., Zhou T.L., Wild C.P., Xia X.L., Baffoebonnie A., Oforiadjei D., et al. Proc. Natl. Acad. Sci. USA 1995, 92:2384-2387.
78. Michaelis U.R., Fisslthaler B., Barbosa-Sicard E., Falck J.R., Fleming I., Busse R. J. Cell. Sci. 2005, 118:5489-5498.
79. Miyata M., Kudo G., Lee Y.H., Yang T.J., Gelboin H.V., Fernandez-Salguero P., Kimura S., Gonzalez F.J. J. Biol. Chem. 1999, 274:23963-23968.
80. Moghaddam M.F., Grant D.F., Cheek J.M., Greene J.F., Williamson K.C., Hammock B.D. Nat. Med. 1997, 3:562-566.
81. Moody D.E., Loury D.N., Hammock B.D. Fed. Proc. 1983, 42:2259. 2259.
82. Morisseau C., Goodrow M.H., Dowdy D., Zheng J., Greene J.F., Sanborn J.R., Hammock B.D. Proc. Natl. Acad. Sci. USA 1999, 96:8849-8854.
83. Morisseau C., Hammock B.D. Annu. Rev. Pharmacol. Toxicol. 2005, 45:311-333.
84. Morisseau C., Newman J.W., Dowdy D.L., Goodrow M.H., Hammock B.D. Chem. Res. Toxicol. 2001, 14:409-415.
85. Mullen R.T., Trelease R.N., Duerk H., Arand M., Hammock B.D., Oesch F., Grant D.F. FEBS Lett. 1999, 445:301-305.
86. Mullin C.A., Hammock B.D. Arch. Biochem. Biophys. 1982, 216:423-439.
87. Müller F., Arand M., Frank H., Seidel A., Hinz W., Winkler L., Häne K., Blee E., Beetham J.K., Hammock B.D., et al. Eur. J. Biochem. 1997, 245:490-496.
88. Nardini M., Ridder I.S., Rozeboom H.J., Kalk K.H., Rink R., Janssen D.B., Dijkstra B.W. J. Biol. Chem. 1999, 274:14579-14586.
89. Nebert D.W., Dalton T.P., Okey A.B., Gonzalez F.J. J. Biol. Chem. 2004, 279:23847-23850.
90. Nelson D.R., Koymans L., Kamataki T., Stegeman J.J., Feyereisen R., Waxman D.J., Waterman M.R., Gotoh O., Coon M.J., Estabrook R.W., et al. Pharmacogenetics 1996, 6:1-42.
91. Newman J.W., Morisseau C., Hammock B.D. Prog. Lipid Res. 2005, 44:1-51.
92. Newman J.W., Morisseau C., Harris T.R., Hammock B.D. Proc. Natl. Acad. Sci. USA 2003, 100:1558-1563.
93. Node K., Huo Y.Q., Ruan X.L., Yang B.C., Spiecker M., Ley K., Zeldin D.C., Liao J.K. Science 1999, 285:1276-1279.
94. Oakley A.J., Klvana M., Otyepka M., Nagata Y., Wilce M.C., Damborsky J. Biochemistry (Mosc) 2004, 43:870-878.
95. Oesch F. Xenobiotica 1973, 3:305-340.
96. Oesch F. Biochem. J. 1974, 139:77-88.
97. Oesch F., Bentley P., Glatt H.R. Int. J. Cancer 1976, 18:448-452.
98. Oesch F., Jerina D.M., Daly J. Biochim. Biophys. Acta 1971, 227:685-691.
99. Oesch F., Jerina D.M., Daly J.W. Arch. Biochem. Biophys. 1971, 144:253-261.
100. Oesch F., Kaubisch N., Jerina D.M., Daly J.W. Biochemistry (Mosc) 1971, 10:4858-4866.
101. Ohtoshi K., Kaneto H., Node K., Nakamura Y., Shiraiwa T., Matsuhisa M., Yamasaki Y. Biochem. Biophys. Res. Commun. 2005, 331:347-350.
102. Oliw E.H., Guengerich F.P., Oates J.A. J. Biol. Chem. 1982, 257:3771-3781.
103. Ollis D.L., Cheah E., Cygler M., Dijkstra B., Frolow F., Franken S.M., Harel M., Remington S.J., Silman I., Schrag J., et al. Protein Eng. 1992, 5:197-211.
104. Ota K., Hammock B.D. Science 1980, 207:1479-1481.
105. Ozawa T., Sugiyama S., Hayakawa M., Satake T., Taki F., Iwata M., Taki K. Am. Rev. Respir. Dis. 1988, 137:535-540.
106. Pace-Asciak C.R., Lee W.S. J. Biol. Chem. 1989, 264:9310-9313.
107. Pacifici G.M., Franchi M., Bencini C., Rane A. Br. J. Clin. Pharmacol. 1986, 22:269-274.
108. Pinot F., Grant D.F., Beetham J.K., Parker A.G., Borhan B., Landt S., Jones A.D., Hammock B.D. J. Biol. Chem. 1995, 270:7968-7974.
109. Pokreisz P., Fleming I., Kiss L., Barbosa-Sicard E., Fisslthaler B., Falck J.R., Hammock B.D., Kim I.H., Szelid Z., Vermeersch P., et al. Hypertension 2006, 47:762-770.
110. Porter T.D., Beck T.W., Kasper C.B. Arch. Biochem. Biophys. 1986, 248:121-129.
111. Pries F., Kingma J., Pentenga M., Vanpouderoyen G., Jeronimusstratingh C.M., Bruins A.P., Janssen D.B. Biochemistry (Mosc) 1994, 33:1242-1247.
112. Przybyla-Zawislak B.D., Srivastava P.K., Vazquez-Matias J., Mohrenweiser H.W., Maxwell J.E., Hammock B.D., Bradbury J.A., Enayetallah A.E., Zeldin D.C., Grant D.F. Mol. Pharmacol. 2003, 64:482-490.
113. Rappaport S.M., Yeowelloconnell K., Bodell W., Yager J.W., Symanski E. Cancer Res. 1996, 56:5410-5416.
114. Ridder I.S., Rozeboom H.J., Kalk K.H., Janssen D.B., Dijkstra B.W. J. Biol. Chem. 1997, 272:33015-33022.
115. Rink R., Kingma J., Spelberg J.H.L., Janssen D.B. Biochemistry (Mosc) 2000, 39:5600-5613.
116. Robbins D.K., Wedlund P.J., Kuhn R., Baumann R.J., Levy R.H., Chang S.L. Br. J. Clin. Pharmacol. 1990, 29:759-762.
117. Sandberg M., Hassett C., Adman E.T., Meijer J., Omiecinski C.J. J. Biol. Chem. 2000, 275:28873-28881.
118. Sandberg M., Meijer J. Biochem. Biophys. Res. Commun. 1996, 221:333-339.
119. Schnabell A., Yao P., Nussler A.K., Eichelbaum M., Burk O. Drug Metab. Rev. 2006, 38:59-60.
120. Sinal C.J., Miyata M., Tohkin M., Nagata K., Bend J.R., Gonzalez F.J. J. Biol. Chem. 2000, 275:40504-40510.
121. Smith C.A.D., Harrison D.J. Lancet 1997, 350:630-633.
122. Spector A.A., Norris A.W. Am. J. Physiol. Cell Physiol. 2007, 292:C996-C1012.
123. Srivastava P.K., Sharma V.K., Kalonia D.S., Grant D.F. Arch. Biochem. Biophys. 2004, 427:164-169.
124. Sumner S.J., Fennell T.R. Crit. Rev. Toxicol. 1994, 24:S11-S33.
125. Thunnissen M.M.G.M., Nordlund P., Haeggstrom J.Z. Nat. Struct. Biol. 2001, 8:131-135.
126. Tran K.L., Aronov P.A., Tanaka H., Newman J.W., Hammock B.D., Morisseau C. Biochemistry (Mosc) 2005, 44:12179-12187.
127. Tzeng H.F., Laughlin L.T., Armstrong R.N. Biochemistry (Mosc) 1998, 37:2905-2911.
128. Tzeng H.F., Laughlin L.T., Lin S., Armstrong R.N. J. Am. Chem. Soc. 1996, 118:9436-9437.
129. Van Der Werf M.J., Orru R.V.A., Overkamp K.M., Swarts H.J., Osprian I., Steinreiber A., De Bont J.A.M., Faber K. Appl. Microbiol. Biotechnol. 1999, 52:380-385.
130. Van Der Werf M.J., Overkamp K.M., De Bont J.A.M. J. Bacteriol. 1998, 180:5052-5057.
131. Van Loo B., Kingma J., Arand M., Wubbolts M.G., Janssen D.B. Appl. Environ. Microbiol. 2006, 72:2905-2917.
132. Verschueren K.H.G., Seljee F., Rozeboom H.J., Kalk K.H., Dijkstra B.W. Nature 1993, 363:693-698.
133. Von Der Hude W., Carstensen S., Obe G. Mutat. Res. 1991, 249:55-70.
134. Waechter F., Bentley P., Bieri F., Staubli W., Volkl A., Fahimi H.D. FEBS Lett. 1983, 158:225-228.
135. Watabe T., Ozawa N., Ishii H., Chiba K., Hiratsuka A. Biochem. Biophys. Res. Commun. 1986, 140:632-637.
136. Wickliffe J.K., Herring S.M., Hallberg L.M., Galbert L.A., Masters O.E., Ammenheuser M.M., Xie J.W., Friedberg E.C., Lloyd R.S., Abdel-Rahman S.Z., et al. Chem. Biol. Interact. 2007, 166:226-231.
137. Williams P.A., Cosme J., Sridhar V., Johnson E.F., Mcree D.E. Mol. Cell 2000, 5:121-131.
138. Yamada T., Morisseau C., Maxwell J.E., Argiriadi M.A., Christianson D.W., Hammock B.D. J. Biol. Chem. 2000, 275:23082-23088.
139. Zeldin D.C., Kobayashi J., Falck J.R., Winder B.S., Hammock B.D., Snapper J.R., Capdevila J.H. J. Biol. Chem. 1993, 268:6402-6407.
140. Zou J.Y., Hallberg B.M., Bergfors T., Oesch F., Arand M., Mowbray S.L., Jones T.A. Structure 2000, 8:111-122.
141. Zusterzeel P.L.M., Peters W.H.M., Visser W., Hermsen K.J.M., Roelofs H.M.J., Steegers E.A.P. J. Med. Genet. 2001, 38:234-237.