New aromatic substituted pyrazoles as selective inhibitors of human adipocyte fatty acid-binding protein

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 10, 2011, Pages 2949-2952

  Liu, Xiujie ^a,b   Huang, Xiaoli ^a,b   Lin, Wanhua ^a,b   Wang, Dongye ^a   Diao, Yanyan ^c   Li, Honglin ^c   Hui, Xiaoyan ^d   Wang, Yu ^a,d   Xu, Aimin ^a,d   Wu, Donghai ^a   Ke, Ding ^a  

^a INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

^c EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^d UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

a FABP inhibitor; Aromatic substituted pyrazoles; Inflammation related diseases; Inflammatory response

Indexed keywords

CYTOKINE; FATTY ACID BINDING PROTEIN 4; LIPOPOLYSACCHARIDE; PYRAZOLE DERIVATIVE;

ARTICLE; BINDING AFFINITY; DRUG BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HYDROPHOBICITY; INFLAMMATION;

ADIPOCYTES; ANTI-INFLAMMATORY AGENTS; DRUG DESIGN; FATTY ACID-BINDING PROTEINS; HUMANS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PROTEIN BINDING; PYRAZOLES;

EID: 79955561585     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.03.063     Document Type: Article

References (27)

1. M. Furuhashi, and G.S. Hotamisligil Nat. Rev. Drug Disc. 7 2008 489
2. A.J. Chmurzynska Appl. Genet. 47 2006 39
3. M. Furuhashi, R. Fucho, C.Z. Gorgun, G. Tuncman, H. Cao, and G.S. Hotamisligil J. Clin. Invest. 118 2008 2640
4. L. Scheja, L. Makowski, K.T. Uysal, S.M. Wiesbrock, D.R. Shimshek, D.S. Meyers, M. Morgan, R.A. Parker, and G.S. Hotamisligil Diabetes 48 1999 1987
5. L. Makowski, J.B. Boord, K. Maeda, V.R. Babaev, K.T. Uysal, M.A. Morgan, R.A. Parker, J. Suttles, S. Fazio, G.S. Hotamisligil, and M.F. Linton Nat. Med. 7 2001 699
6. G.S. Hotamisligil, R.S. Johnson, R.J. Distel, R. Ellis, V.E. Papaioannou, and B.M. Spiegelman Science 274 1996 1377
7. K.T. Uysal, L. Scheja, S.M. Wiesbrock, S. Bonner-Weir, and G.S. Hotamisligil Endocrinology 141 2000 3388
8. L. Makowski, K.C. Brittingham, J.M. Reynolds, J. Suttles, and G.S. Hotamisligil J. Biol. Chem. 280 2005 12888
9. A.E. Jenkins-Kruchten, A. Bennaars-Eiden, J.R. Ross, W.J. Shen, F.B. Kraemer, and D.A. Bernlohr J. Biol. Chem. 278 2003 47636
10. A.J. Smith, B.R. Thompson, M.A. Sanders, and D.A. Bernlohr J. Biol. Chem. 282 2007 32424
11. B.R. Thompson, A.M. Muzurkiewicz-Munoz, J. Suttles, C. Carter-Su, and D.A. Bernlohr J. Biol. Chem. 284 2009 13474
12. A. Adida, and F. Spener Biochim. Biophys. Acta 1761 2006 172
13. S.D. Yers, K.L. Nedrow, R.E. Gillilan, and N. Noy Biochemistry 46 2007 6744
14. X. Hui, H. Li, Z. Zhou, K.S. Lam, Y. Xiao, D. Wu, K. Ding, Y. Wang, P.M. Vanhoutte, and A. Xu J. Biol. Chem. 285 2010 10273
15. M. Furuhashi, G. Tuncman, C.Z. Gorgun, L. Makowshi, G. Atsumi, E. Vallancourt, K. Kono, V.R. Babaev, S. Fazio, M.F. Linton, R. Sulsky, J.A. Robl, R.A. Parker, and G.S. Hostamisligil Nature 447 2007 959
16. A.V. Hertzel, K. Hellberg, J.M. Reynold, A.C. Kruse, B.E. Juhlmann, A.J. Smith, M.A. Sanders, D.H. Ohlendorf, J. Suttles, and D.A. Bernlohr J. Med. Chem. 52 2009 6024
17. R. Ringom, E. Axen, J. Uppenberg, T. Lundback, L. Rondahl, and T. Barf Bioorg. Med. Chem. Lett. 14 2004 4449
18. T. Barf, F. Lehmann, K. Hammer, S. Haile, E. Axen, C. Medina, J. Uppenberg, S. Sevensson, L. Rondahl, and T. Lundback Bioorg. Med. Chem. Lett. 19 2009 1745
19. F. Lehmann, S. Haile, E. Axen, C. Medina, J. Uppenberg, S. Scensson, T. Lundback, L. Rondahl, and T. Barf Bioorg. Med. Chem. Lett. 14 2004 4445
20. R. Sulsky, D.R. Magnin, Y. Huang, L. Simpkins, P. Taunk, M. Patel, Y. Zhu, T.R. Stouch, D. Bassolino-Klimas, R. Parker, T. Harrity, R. Stoffel, D.S. Taylor, T.B. Lavoie, K. Kish, B.L. Jacobson, S. Sheriff, L.P. Adam, W.R. Ewing, and J.A. Robl Bioorg. Med. Chem. Lett. 17 2007 3511
21. M.J.P. Van Dongen, J. Uppenberg, S. Sevensson, T. Lundback, T. Akerud, M. Wikstron, and J. Schultz J. Am. Chem. Soc. 124 2001 11874
22. H. Cai, G. Yan, X. Zhang, O. Gorbenko, H. Wang, and W. Zhu Bioorg. Med. Chem. Lett. 20 2010 3675
23. C.D. Kane, and D.A. Bernlohr Anal. Biochem. 233 1996 197
24. In the 1,8-ANS displacement assay, compounds were dissolved in ethanol and were added to sodium phosphate buffer (PH7.4) system containing 10 μM of 1,8-ANS and 0.5 μM of FABPs (final concentrations). The fluorescence enhancement was measured using a Perkin-Elmer LS55 fluorescence spectrophotometer with 5 nm excitation and emission slit widths.
25. T. Velkov, M.L.R. Lim, B. Capuano, and R.J. Prankerd J. Chromatogr. B 867 2008 238
26. F. Mohamadi, N. Richards, W. Guida, R. Liskamp, M. Lipton, C. Caufield, G. Chang, T. Hendrickson, and W. Still J. Comput. Chem. 11 2004 440
27. R. Friesner, J. Banks, R. Murphy, T. Halgren, J. Klicic, D. Mainz, M. Repasky, E. Knoll, M. Shelley, and J. Perry J. Med. Chem. 4 2004 1739