Abstract
In this paper, we have screened a library of two different series of compounds to identify potent lipoxygenase (LOX) inhibitors. A number of new biphenyl bis(benzenesulfonamides) 2–3, indol-3-yl-benzenesulfonyl and acetohydrazides 4–5 and indol-3-yl-hydrazinecarboxylate 6 were synthesized and evaluated in vitro for LOX inhibitory activity. Compounds biphenyl bis(benzenesulfonamide) 2a and indol-3-yl-benzenesulfonylhydrazide 4e presented the best anti-LOX activity within these series with IC50 values 96.31 ± 0.18 and 81.21 ± 2.14 μM, respectively. The results were confirmed with docking studies.
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C.D. Funk, Science 294, 1871–1875 (2001)
S. Fiorucci, R. Meli, M. Bucci, G. Cirino, Biochem. Pharmacol. 62, 1433–1438 (2001)
C. Charlier, C. Michaux, Eur. J. Med. Chem. 38, 645–659 (2003)
S.T. Prigge, J.C. Boyington, K.S. Doctor, L.M. Amzel, Biochimie 79, 629–636 (1997)
J.S. Larsen, E.P. Acosta, Ann. Pharmacother. 27, 898–903 (1993)
T. Schewe, Biol. Chem. 383, 365–374 (2002)
R. Spanbroek, R. Grabner, K. Lotzer, M. Hildner, A. Urbach, K. Ruhling, M.P. Moos, B. Kaiser, T.U. Cohnert, T. Wahlers, A. Zieske, G. Plenz, H. Robenek, P. Salbach, H. Kuhn, O. Radmark, B. Samuelsson, A.J. Habenicht, Proc. Natl. Acad. Sci. 100, 1238–1243 (2003)
U. Kelavkar, W. Glasgow, T.E. Eling, Curr. Urol. Rep. 3, 207–214 (2002)
D. Nie, M. Che, D. Grignon, K. Tang, K.V. Honn, Cancer Metastasis Rev. 20, 195–206 (2001)
G. Rai, V. Kenyon, A. Jadhav, L. Schultz, M. Armstrong, J.B. Jameson, E. Hoobler, W. Leister, A. Simeonov, T.R. Holman, D.J. Maloney, J. Med. Chem. 53, 7392–7404 (2010)
D. Pratico, V. Zhukareva, Y. Yao, K. Uryu, C.D. Funk, J.A. Lawson, J.Q. Trojanowski, V.M.-Y. Lee, Am. J. Pathol. 164, 1655–1662 (2004)
L. Zhao, T. Grosser, S. Fries, L. Kadakia, H. Wang, J. Zhao, R. Falotico, Expert Rev. Clin. Immunol. 2, 649–658 (2006)
L. Zhao, C.D. Funk, Trends Cardiovasc. Med. 14, 191–195 (2004)
J.A. Cornicelli, B.K. Trivedi, Curr. Pharm. Des. 5, 11–20 (1999)
Y. Huo, L. Zhao, M.C. Hyman, P. Shashkin, B.L. Harry, T. Burcin, S.B. Forlow, M.A. Stark, D.F. Smith, S. Clarke, S. Srinivasan, C.C. Hedrick, D. Pratico, J.L. Witztum, J.L. Nadler, C.D. Funk, K. Ley, Circulation 110, 2024–2031 (2004)
B.N. Setty, M.H. Werner, Y.A. Hannun, M.J. Stuart, Blood 80, 2765–2773 (1992)
G.K.J. Dams, I. Vereychen, K.L.A. Vanacker, E.M.P.E. Gustin, W.G. Verschueren, A.C. Ohagen, WO 2007113337A1, 2007
G.J. Latham, M.M.W inkler, B.L. Pasloske, A.W. Kudlicki, US 20050014169, 2005
R. Shapiro, J.L. Jenkins, R.Y.T. Kao, G.J. Latham, WO 2004076640, 2004
B. Pelcman, M. Almeida, M. Katkevics, P. Nilson, W. Schaal, K. Olofsson, US 20110294853, 2011
Y. Iino, K. Fujita, T. Tsuji, A. Kodaira, K. Takehana, T. Kobayashi, T. Yamamoto, EP1113000A1, 2001
J. Li, J. Chen, C. Gui, L. Zhang, Y. Qin, Q. Xu, J. Zhang, H. Liu, X. Shen, H. Jiang, Bioorg. Med. Chem. 14, 2209–2224 (2006)
B. Pelcman, P. Nilson, WO 2008107661, 2009
B. Pelcman, P. Nilson, M. Katkevics, WO 2009030887A3, 2009
B. Pelcman, M. Almeida, M. Katkevics, P. Nilson, W. Schaal, K. Olofsson, WO 2010029300A1, 2010
Y.Y. Li, H.S. Wu, L. Tang, C.R. Feng, J.H. Yu, Y. Li, Y.S. Yang, B. Yang, Q.J. He, Pharmacol. Res. 56, 335–343 (2007)
M.A. Radwan, N.M. Sabry, S.M. El-Shenawy, Bioorg. Med. Chem. 15, 3832–3841 (2007)
B.B. Mishra, R.K. Singh, A. Srivastava, V.J. Tripathi, V.K. Tiwari, Mini. Rev. Med. Chem. 9, 107–123 (2009)
T.P. Pathak, K.M. Gligorich, B.E. Welm, M.S. Sigman, J. Am. Chem. Soc. 132, 7870–7871 (2010)
O. Talaz, I. Gulcin, S. Goksu, N. Saracoglu, Bioorg. Med. Chem. 17, 6583–6589 (2009)
Z. Zhao, S.E. Wolkenberg, P.E. Sanderson, M. Lu, V. Munshi, G. Moyer, M. Feng, A.V. Carella, L.T. Ecto, L.J. Gabryelski, M.T. Lai, S.G. Prasad, Y. Yan, G.B. McGaughey, M.D. Miller, C.W. Lindsley, G.D. Hartman, J.P. Vacca, T.M. Williams, Bioorg. Med. Chem. Lett. 18, 554–559 (2008)
J.P. Liou, K.S. Hsu, C.C. Kuo, C.Y. Chang, J. Pharmacol. Exp. Ther. 323, 398–405 (2007)
D.S. Weinstein, W. Liu, Z. Gu, C. Langevine, K. Ngu, L. Fadnis, D.W. Combs, D. Sitkoff, S. Ahmad, S. Zhuang, X. Chen, F. Wang, D.A. Loughney, K.S. Atwal, R. Zahler, J.E. Macor, C.S. Madsen, Bioorg. Med. Chem. Lett. 15, 1435–1440 (2005)
D.S. Weinstein, W. Liu, C.S. Madsen, Bioorg. Med. Chem. Lett. 17, 5115–5120 (2007)
H. Sadeghian, N. Attaran, Z. Jafari, M.R. Saberi, M. Pordel, M.M. Riazi, Bioorg. Med. Chem. 17, 2327–2335 (2009)
M. Bakavoli, M. Nikpour, M. Rahimizadeh, M.R. Saberi, H. Sadeghian, Bioorg. Med. Chem. 15, 2120–2126 (2007)
V. Kenyon, I. Chorny, W.J. Carvajal, T.R. Holman, M.P. Jacobson, J. Med. Chem. 49, 1356–1363 (2006)
Y. Wu, C. He, Y. Gao, S. He, Y. Liu, L. Lai, J. Med. Chem. 55, 2597–26605 (2012)
S. Ferreira, S. Moncada, J. Vane, Nat. New Biol. 231, 237–239 (1971)
M. Yar, L.R. Sidra, E. Pontiki, N. Mushtaq, M. Ashraf, R. Nasar, I.U. Khan, N. Mahmood, S.A.R. Naqvi, Z.A. Khan, S.A. Shahzad, J. Iran. Chem. Soc. (2013). doi:10.1007/s13738-013-0308-3
M. Yar, M. Bajda, R.A. Mehmood, L.R. Sidra, N. Ullah, L. Shahzadi, M. Ashraf, T. Ismail, S.A. Shahzad, Z.A. Khan, S.A.R. Naqvi, N. Mahmood, Lett. Drug Des. Discov. (2014). doi:10.2174/15701808113106660078
W. Minor, J. Steczko, B. Stec, Z. Otwinowski, J.T. Bolin, Biochemistry 35, 10687–10701 (1996)
H. Berman, K. Henrick, H. Nakamura, Nat. Struct. Biol. 10, 980 (2003)
A.L. Tappel, Arch. Biochem. Biophys. 44, 378–395 (1953)
CambridgeSoft, USA, ChemDraw Ultra_v.12 (1986–2009). http://www.cambridgesoft.com/software/chemDraw/. Accessed 15 May 2014
OpenBabel_ v.2.2.3 (2006). http://sourceforge.net/projects/openbabel/. Accessed 16 May 2014
http://www.cgl.ucsf.edu/chimera. Accessed 16 May 2014
E.F. Pettersen, T.D. Goddard, C.C. Huang, G.S. Couch, D.M. Greenblatt, E.C. Meng, T.E. Ferrin, J. Comput. Chem. 25, 1605–1612 (2004)
J. Wang, R.M. Wolf, J.W. Caldwell, P.A. Kollman, D.A. Case, J. Comput. Chem. 25, 1157–1174 (2004)
J. Wang, W. Wang, P.A. Kollman, D.A. Case, J. Mol. Graph. Model. 25, 247–260 (2006)
B. Hess, C. Kutzner, D. van der Spoel, E. Lindahl, J. Chem. Theory Comput. 4, 435–447 (2008)
K. Lindorff-Larsen, S. Piana, K. Palmo, P. Maragakis, J.L. Klepeis, R.O. Dror, D.E. Shaw, Proteins 78, 1950–1958 (2010)
O. Trott, A.J. Olson, J. Comput. Chem. 31, 455–461 (2010)
Autodock Vina v. 1.1.1. Copyright_ 1989–2010. The Scripps Research Institute
Sargis Pallakyan, PyRx-Python Prescription, v.0.5. The Scripps Research Institute, 2008–2010. http://pyrx.scripps.edu/
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We acknowledge the Higher Education Commission and Ministry of Science and Technology, Pakistan, for financial support.
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Mutahir, S., Yar, M., Khan, M.A. et al. Synthesis, characterization, lipoxygenase inhibitory activity and in silico molecular docking of biaryl bis(benzenesulfonamide) and indol-3-yl-hydrazide derivatives. J IRAN CHEM SOC 12, 1123–1130 (2015). https://doi.org/10.1007/s13738-014-0573-9
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DOI: https://doi.org/10.1007/s13738-014-0573-9