Reviews

Advances in the Research of Human Soluble Epoxide Hydrolase Inhibitors

  • Huang Shaoxu ,
  • Wang Yong ,
  • Long Yaqiu
Expand
  • Laboratory of Medicinal Chemistry, Shanghai Institute of Materia Medica, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences, Shanghai 201203

Received date: 2011-07-13

  Revised date: 2011-11-17

  Online published: 2011-12-07

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 81021062, 81072527).

Abstract

Hypertension is a common illness nowadays. Although a wide variety of antihypertensive agents are available in the market for the treatment of hypertension, the antihypertensive treatment tends to be individualized, and the treatment should exceed the limitation of lowering blood pressure only. Compared to other antihypertensive agents, the advantage of human soluble epoxide hydrolase inhibitors (HsEHIs) is that they can not only reduce the blood pressure, but also have remarkable anti-inflammatory effects. Herein, the development of human soluble epoxide hydrolase inhibitors is reviewed from early epoxide HsEHIs to the third generation of urea HsEHIs.

Cite this article

Huang Shaoxu , Wang Yong , Long Yaqiu . Advances in the Research of Human Soluble Epoxide Hydrolase Inhibitors[J]. Chinese Journal of Organic Chemistry, 2012 , 32(05) : 877 -888 . DOI: 10.6023/cjoc1107132

References

[1] Jerina, D. M. Lloydia 1974, 37, 212.

[2] Oliw, E. H. Prog. Lipid Res. 1994, 33, 329.  

[3] Morisseau, C. Hammock, B. D. Annu. Rev. Pharmacol. Toxicol.2005, 45, 311.  

[4] Hammock, B. D.; Grant, D.; Storms, D. In Comprehensive Toxicology,Eds.: Sipes, I.; McQueen, C.; Gandolfi, A., Pergamon, NewYork, 1997, 283.

[5] Oesch, F. Xenobiotica 1973, 3, 305.  

[6] Levin, W.; Michaud, D. P.; Thomas, P. E.; Jerina, D. M. Arch.Biochem. Biophys. 1983, 220, 485.  

[7] Pace-Asciak, C. R.; Lee, W. S. J. Biol. Chem. 1989, 264, 9310.

[8] (a) Yu, Z.; Xu, F.; Huse, L. M.; Morisseau, C.; Draper, A. J. Circ.Res. 2000, 87, 992.(b) Davis, B. B.; Thompson, D. A.; Howard, L. L.; Morisseau, C.;Hammock, B. D. Proc. Natl. Acad. Sci U. S. A. 2002, 99, 2222.(c) Imig, J. D.; Zhao, X.; Capdevila, J. H.; Morisseau, C.; Hammock,B. D. Hypertension 2002, 39, 690.(d) Zhao, X.; Yamamoto, T.; Newman, J. W.; Kim, I. H.; Watanabe,T. J. Am. Soc. Nephrol. 2004, 15, 1244.

[9] Arand, M.; Grant, D. F.; Beetham, J. K.; Friedberg, T.; Oesch, F.;Hammock, B. D. FEBS Lett. 1994, 338, 251.  

[10] Ollis, D. L.; Cheah, E.; Cygler, M.; Dijkstra, B.; Frolow, F. Curr.Protein Pept. Sci. 2000, 1, 209.  

[11] Moghaddam, M. F.; Grant, D. F.; Cheek, J. M.; Greene, J. F.; Williamson,K. C.; Hammock, B. D. Nat. Med. 1997, 3, 562.  

[12] Morisseau, C.; Goodrow, M. H.; Dowdy, D.; Zheng, J.; Greene, J.F.; Sanborn, J. R.; Hammock, B. D. Proc. Natl. Acad. Sci. U. S. A.1999, 96, 8849.  

[13] Spector, A. A.; Fang, X.; Snyder, G. D.; Weintraub, N. L. Prog.Lipid Res. 2004, 43, 55.  

[14] (a) Imig, J. D.; Zhao, X.; Zaharis, C. Z.; Olearczyk, J. J.; Pollock,D. M.; Newman, J. W.; Kim, I.-H.; Watanabe, T.; Hammock, B. D.Hypertension 2005, 46, 975.(b) Ai, D.; Fu, Y.; Guo, D.; Tanaka, H.; Wang, N.; Tang, C.;Hammock, B. D.; Shyy, J. Y.-J.; Zhu, Y. Proc. Natl. Acad. Sci. U.S. A. 2007, 104, 9018.

[15] Sinal, C. J.; Miyata, M.; Tohkin, M.; Nagata, K.; Bend, J. R.; Gonzalez,F. J. J. Biol. Chem. 2000, 275, 40504.  

[16] Kim, I.-H.; Nishi, K.; Tsai, H.-J.; Bradford, T.; Koda, Y.; Watanabe,T.; Morisseau, C.; Blanchfield, J.; Tothb, I.; Hammock, B. D.Bioorg. Med. Chem. 2007, 15, 312.  

[17] The ALLHAT Officers and Coordinators for the ALLHAT CollaborativeResearch Group J. Am. Med. Assoc. 2002, 288, 2981.  

[18] Schmelzer, K. R.; Inceoglu, B.; Kubala, L.; Kim, I. H.; Jinks, S. L.;Eiserich, J. P.; Hammock, B. D. Proc. Natl. Acad. Sci. U. S. A.2006, 103, 13646.

[19] Mullin, C. A.; Hammock, B. D. 1982, 216, 423.

[20] Dietze, E. C.; Kuwano, E.; Casas, J.; Hammock, B. D. Biochem.Pharmacol. 1991, 42, 1163.  

[21] Morisseau, C.; Du, G.; Newman, J. W.; Hammock, B. D. Arch.Biochem. Biophys. 1998, 356, 214.  

[22] Draper, A. J.; Hammock, B. D. Toxicol. Sci. 1999, 52, 26.  

[23] Gaetke, L. M.; McClain, C. J.; Talwalkar, R. T.; Shedlofsky, S. I.Am. J. Physiol. Endocrin. Metab. 1997, 272, E952.  

[24] Dietze, E. C.; Kuwano, E.; Hammock, B. D. Anal. Biochem. 1994,216, 176.  

[25] Jones, P. D.; Wolf, N. M.; Morisseau, C.; Whetstone, P.; Hock, B.;Hammock, B. D. Anal. Biochem. 2005, 343, 66.  

[26] Argiriadi, M. A.; Morisseau, C.; Hammock, B. D.; Christianson, D.W. Proc. Natl. Acad. Sci. U. S. A. 1999, 96, 10637. [27] Morisseaua, C.; Goodrow, M. H.; Newman, J. W.; Wheelock, C.E.; Dowdy, D. L.; Hammock, B. D. Biochem. Pharmacol. 2002, 63,1599.  

[28] Kim, I.-H.; Morisseau, C.; Watanabe, T.; Hammock, B. D. J. Med.Chem. 2004, 47, 2110.  

[29] Kim, I.-H.; Heirtzler, F. R.; Morisseau, C.; Nishi, K.; Tsai, H.-J.;Hammock, B. D. J. Med. Chem. 2005, 48, 3621.  

[30] (a) Argiriadi, M. A.; Morisseau, C.; Goodrow, M. H.; Dowdy, D.L.; Hammock, B. D.; Christianson, D. W. J. Biol. Chem. 2000, 275,15265.(b) Gomez, G. A.; Morisseau, C.; Hammock, B. D.; Christianson,D. W. Biochemistry 2004, 43, 4716.  

[31] Morisseau, C.; Newman, J. W.; Tsai, H.-J.; Baecker P. A.; Hammock,B. D. Bioorg. Med. Chem. Lett. 2006, 16, 5439.  

[32] Jones, P. D.; Tsai, H.-J.; Do, Z. N.; Morisseau, C.; Hammock, B. D.Bioorg. Med. Chem. Lett. 2006, 16, 5212.  

[33] Li, H.-Y.; Jin, Y.; Morisseau, C.; Bruce, D.; Hammock, B. D.;Long, Y.-Q. Bioorg. Med. Chem. 2006, 14, 6586.  

[34] Huang, S.-X.; Li, H.-Y.; Liu, J.-Y.; Morisseau, C.; Hammock, B.D.; Long, Y.-Q. J. Med. Chem. 2010, 53, 8376.  

[35] Kasagami, T.; Kim, I.-H.; Tsai, H.-J.; Nishi, K.; Hammock, B. D.;Morisseau, C. Bioorg. Med. Chem. Lett. 2009, 19, 1784.  

[36] Anandan, S.-K.; Webb, H. K.; Do, Z. N.; Gless, R. D. Bioorg. Med.Chem. Lett. 2009, 19, 4259.  

[37] Rose, T. E.; Morisseau, C.; Liu, J.-Y.; Inceoglu, B.; Jones, P. D.;Sanborn, J. R.; Hammock, B. D. J. Med. Chem. 2010, 53, 7067.  

[38] Eldrup, A. B.; Soleymanzadeh, F.; Farrow, N. A.; Kukulka, A.; DeLombaert, S. Bioorg. Med. Chem. Lett. 2010, 20, 571.  

[39] Kim, I.-H.; Park, Y.-K.; Hammock, B. D.; Nishi, K. J. Med. Chem.2011, 54, 1752.  

[40] Xie, Y.; Liu, Y.; Gong, G.; Smith, D. H.; Yan, F.; Rinderspacher,A.; Feng, Y.; Zhu, Z.; Li X.; Deng, S.-X.; Branden, L.; Vidovi?, D.;Chung, C.; Sch黵er, S.; Morisseau, C.; Hammock, B. D.; Landry,D. W. Bioorg. Med. Chem. Lett. 2009, 19, 2354.  

[41] Taylor, S. J.; Soleymanzadeh, F.; Eldrup, A. B.; Farrow, N. A.;Muegge, I.; Kukulka, A.; Kabcenell, A. K.; De Lombaert, S. Bioorg.Med. Chem. Lett. 2009, 19, 5864.  

[42] Eldrup, A. B.; Soleymanzadeh, F.; Taylor, S. J.; Muegge, I.;Farrow, N. A.; Joseph, D.; McKellop, K.; Man, C. C.; Kukulka, A.;De Lombaert, S. J. Med. Chem. 2009, 52, 5880.  

[43] (a) Shen, H. C.; Ding, F.-X.; Wang, S.; Deng, Q.; Zhang, X.; Chen,Y.; Zhou, G.; Xu, S.; Chen, H.-S.; Tong, X.; Tong, V.; Mitra, K.;Kumar, S.; Tsai, C.; Stevenson, A. S.; Pai, L.-Y.; Alonso-Galicia,M.; Chen, X.; Soisson, S. M.; Roy, S.; Zhang, B.; Tata, J. R.; Berger,J. P.; Colletti, S. L. J. Med. Chem. 2009, 52, 5009.(b) Shen, H. C.; Ding, F.-X.; Wang, S.; Xu, S.; Chen, H.-S.; Tong,X.; Tong, V.; Mitra, K.; Kumar, S.; Zhang, X.; Chen, Y.; Zhou, G.;Pai, L.-Y.; Alonso-Galicia, M.; Chen, X.; Zhang, B.; Tata, J. R.;Berger, J. P.; Colletti, S. L. Bioorg. Med. Chem. Lett. 2009, 19,3398.(c) Shen, H. C.; Ding, F.-X.; Deng, Q.; Xu, S.; Tong, X.; Zhang,X.; Chen, Y.; Zhou, G.; Pai, L.-Y.; Alonso-Galicia, M.; Roy, S.;Zhang, B.; Tata, J. R.; Berger, J. P.; Colletti, S. L. Bioorg. Med.Chem. Lett. 2009, 19, 5716.(d) Shen, H. C.; Ding, F.-X.; Deng, Q.; Xu, S.; Chen, H.-S.; Tong,X.; Tong, V.; Zhang, X.; Chen, Y.; Zhou, G.; Pai, L.-Y.;Alonso-Galicia, M.; Zhang, B.; Roy, S.; Tata, J. R.; Berger, J. P.;Colletti, S. L. Bioor. Med. Chem. Lett. 2009, 19, 5314.  

[44] Xing, L.; McDonald, J. J.; Kolodziej, S. A.; Kurumbail, R. G.; Williams,J. M.; Warren, C. J.; O'Neal, J. M.; Skepner, J. E.; Roberds,S. L. J. Med. Chem. 2011, 54, 1211.  

[45] Tanaka, D.; Tsuda, Y.; Shiyama, T.; Nishimura, T.; Chiyo, N.; Tominaga,Y.; Sawada, N.; Mimoto, T.; Kusunose, N. J. Med. Chem.2011, 54, 851.  

Outlines

/