Molecular docking studies on xanthohumol derivatives as novel ‎anticancer agents ‎

Oftadeh, Mohsen; Fereidoonnezhad, Masood; Aliyan, Mina; Aliyan, Fariba

doi:10.30473/icc.2019.43933.1507

Document Type : Original Research Article

Authors

¹ Chemistry Department, Payame Noor University, 19395-4697 Tehran, Iran

² &lrm;Research Center of Marine Pharmaceutical Science, Ahvaz Jundishahpour University of Medical Science, Ahvaz, &lrm;Iran

³ Payame Noor University

⁴ &lrm;3Department of Medicinal Chemistry, School of Pharmacy, Ahvaz Jundishapur University of Medical Sciences, &lrm;Ahvaz, Iran

https://doi.org/10.30473/icc.2019.43933.1507

Abstract

A set of Xanthohumol derivatives were selected and molecular docking studies of these ‎compounds on thioredoxin reductase were conducted. Based on new structural patterns using in ‎silico-screening study, new potent lead compounds were designed. The results due to validated ‎docking protocols lead to find that Thr58, Gly57, Gly21, Asp334, Glu163, Ala130, IIe332, ‎Val44 and Gly132 are the main amino acids in the active site cavity in charge of essential ‎interactions with thioredoxin reductase.‎

Graphical Abstract

Keywords

Main Subjects

Physical chemistry

References

[1] C. Gerhauser, Eur. J. Cancer, 2005, 41, 1941−1954.

[2] M.M. Blanquer-Rossello, J. Oliver, A. Valle, P. Roca, J. Cell. Biochem., 2013, 114, 2785−2794.

[3] M. Festa, A. Capasso, C.W. Dacunto, M. Masullo, A.G. Rossi, C. Pizza, S. Piacente, J. Nat. Prod., 2011, 74, 2505−2513.

[4] J. Strathmann, K. Klimo, S.W. Sauer, J.G. Okun, J.H. Prehn, C. Gerhäuser, FASEB J., 2010, 24, 2938−2950.

[5] Y. Kang, M.A. Park, S.W. Heo, S.Y. Park, K.W. Kang, P.H. Park, J.A. Kim, Biochim. Biophys. Acta, 2013, 1830, 2638−2648.

[6] D. Deeb, X. Gao, H. Jiang, A.S. Arbab, S.A. Dulchavsky, S.C. Gautam, Anticancer Res., 2010, 30, 3333−3339.

[7] K.B. Harikumar, A.B. Kunnumakkara, K.S. Ahn, P. Anand, S. Krishnan, S. Guha, B.B. Aggarwal, Blood, 2009, 113, 2003−2013.

[8] A. Albini, R. Dell'Eva, R. Vené, N. Ferrari, D.R. Buhler, D.M. Noonan, G. Fassina, FASEB J., 2006, 20, 527−529.

[9] S. Monteghirfo, F. Tosetti, C. Ambrosini, S. Stigliani, S. Pozzi, F. Frassoni, G. Fassina, S. Soverini, A. Albini, N. Ferrari, Mol. Cancer Ther., 2008, 7, 2692−2702.

[10] H. Becker, C. Gerhauser, Mol. Nutr. Food Res., 2005, 49, 837−843.

11] C. Gerhauser, A. Alt, E. Heiss, A. Gamal-Eldeen, K. Klimo, J. Knauft, I. Neumann, H.R. Scherf, N. Frank, H. Bartsch, H. Becker, Mol. Cancer Ther., 2002, 1, 959−969.

[12] C.I. Miranda, G.L. Aponso, J.F. Stevens, M.L. Deinzer, D.R. Buhler, Cancer Lett., 2000, 149, 21−29.

[13] T.C. Laurent, E.C. Moore, P. Reichard, J. Biol. Chem., 1964, 239, 3436–3444.

[14] E.C. Moore, P. Reichard, L. Thelander, J. Biol. Chem., 1964, 239, 3445–3452.

[15] A. Holmgren, Eur. J. Biochem., 1968, 6, 475–484.

[16] A. Holmgren, B.O. Soderberg, H. Eklund, C.I. Branden, Proc. Natl. Acad. Sci. USA, 1975, 72, 2305–2309.

[17] L. Zhang, D. Duan, Y. Liu, C. Ge, X. Cui, J. Sun, J. Fang, J. Med. Chem., 2015, 58, 1795−1805.

[18] S. Urig, K. Semin. Cancer Biol.,2006, 16, 452-465.

[19] X.Y. Meng, H.X. Zhang, M. Mezei, M. Cui, Curr. Comput. Aided Drug Des., 2011,7, 146–157.

[20] S. Zare, M. Fereidoonnezhad, D. Afshar, Z. Ramezani, Comput. Biol. Chem., 2017, 67, 22-37.

[21] A. Mojaddami, A. Sakhteman, M. Fereidoonnezhad, Z. Faghih, A. Najdian, S. Khabnadideh, H.Sadeghpour, Z. Res. Pharm. Sci., 2017, 12, 21-30.

[22] HyperChem(TM) Professional 8.0 Hypercube Inc. 1115 NW 4th Street Gainesville Florida 32601 USA.

[23] G.M. Morris R. Huey, A.J. Olson, Using AutoDock for Ligand-Receptor Docking. Current Protocols in Bioinformatics: John Wiley & Sons Inc, 2002.

[24] G.M. Morris, D.S. Goodsell, R.S. Halliday, R. Huey, W.E. Hart, R.K. Belew, A.J. Olson, J. Comput. Chem., 1998, 19, 1639-1662.

[25] A. Hamedi, M.J. Khoshnoud, N. Tanideh, F. Abbasi, M. Fereidoonnezhad, D. Mehrabani, Pharm. Chem. J., 2015, 49, 268-274.

[26] W. Humphrey, A. Dalke, K. Schulten, J. Mol. Graphics, 1996, 14, 33-38.

[27] W.L. DeLano, PyMOL: An open-source molecular graphics tool. Delano Scientific San Carlos. 2002.

[28] M. Oftadeh, M. Fereidoonnezhad, M. Aliyan, F. Aliyan, Phys. Chem. Res., under review.

[29] N. Triballeau, F. Acher, I. Brabet, P.J. Pin, H.O. Bertrand, J. Med. Chem., 2005, 48, 2534-2547.

[30] Z. Rezaei, M. Fereidoonnezhad, Z. Faghih, H. Sadeghpur, A. Mojaddami, A. Sakhteman, Trends Pharm. Sci., 2017, 3, 31-42.

[31] A. Gaulton, L.J. Bellis, A.P. Bento, J. Chambers, M. Davies, A. Hersey, Y. Light, S. McGlinchey, D. Michalovich, B. Al-Lazikani, J.P. Nucleic Acids Res., 2012, 40, D1100–D1107.

[32] A.M. Wassermann, J. Bajorath, Expert Opin. Drug Dis., 2011, 6, 683-687.

[33] E.L. Willighagen, A. Waagmeester, O. Spjuth, P. Ansell, A.J. Williams, V. Tkachenko, J. Hastings, B. Chen, D.J. Wild, J. Cheminform., 2013, 5, 23-28.

[34] N.M. O’Boyle, M. Banck, C.A. James, C. Morley, T. Vandermeersch, G.R. Hutchison, J. Cheminform., 2011, 3, 33-43.

[35] K. Roy, S. Kar, R.N. Das, Validation of QSAR Models. Understanding the Basics of QSAR for Applications in Pharmaceutical Sciences and Risk Assessment Academic Press: Boston, 2015, pp. 231-89.

[36] H. Li, H. Zhang, M. Zheng, J. Luo, L. Kang, X. Liu, X. Wang, H. Jiang, BMC Bioinformatics, 2009, 10, 58-60.

Iranian chemical communication

Molecular docking studies on xanthohumol derivatives as novel ‎anticancer agents ‎

References

References

[17] L. Zhang, D. Duan, Y. Liu, C. Ge, X. Cui, J. Sun, J. Fang, J. Med. Chem., 2015, 58, 1795−1805.

[22] HyperChem(TM) Professional 8.0 Hypercube Inc. 1115 NW 4th Street Gainesville Florida 32601 USA.

Volume 7, Issue 4. pp. 230-306, Serial No. 25
October 2019
Pages 272-284

Molecular docking studies on xanthohumol derivatives as novel ‎anticancer agents ‎

References

References

[17] L. Zhang, D. Duan, Y. Liu, C. Ge, X. Cui, J. Sun, J. Fang, J. Med. Chem., 2015, 58, 1795−1805.

[22] HyperChem(TM) Professional 8.0 Hypercube Inc. 1115 NW 4th Street Gainesville Florida 32601 USA.

Volume 7, Issue 4. pp. 230-306, Serial No. 25October 2019Pages 272-284

Volume 7, Issue 4. pp. 230-306, Serial No. 25
October 2019
Pages 272-284