Antioxidant and anti-inflammatory properties of 1,2,4-oxadiazole analogs of resveratrol

Chemico-Biological Interactions

Volumn 240, Issue , 2015, Pages 200-207

  Gobec, Martina ^a   Tomašič, Tihomir ^a   Markovič, Tijana ^a   Mlinarič Raščan, Irena ^a   Dolenc, Marija Sollner ^a   Jakopin, Žiga ^a  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

Author keywords

1,2,4 Oxadiazole; Anti Inflammatory; Antioxidant; NF B inhibition; Resveratrol

Indexed keywords

1,2,4 OXADIAZOLE DERIVATIVE; HETERODIMER; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; REACTIVE OXYGEN METABOLITE; RESVERATROL; ANTIINFLAMMATORY AGENT; ANTIOXIDANT; NF-KAPPA B KINASE; OXADIAZOLE DERIVATIVE; PROTEIN SERINE THREONINE KINASE; STILBENE DERIVATIVE;

ANTIINFLAMMATORY ACTIVITY; ANTIOXIDANT ACTIVITY; ARTICLE; BINDING SITE; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOKINE PRODUCTION; CYTOKINE RELEASE; CYTOTOXICITY TEST; DRUG DETERMINATION; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; PROTEIN DNA BINDING; ANTAGONISTS AND INHIBITORS; CELL LINE; CELL SURVIVAL; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECTS; ENZYME ACTIVATION; METABOLISM; WESTERN BLOTTING;

ANTI-INFLAMMATORY AGENTS; ANTIOXIDANTS; BLOTTING, WESTERN; CELL LINE; CELL SURVIVAL; ENZYME ACTIVATION; MODELS, MOLECULAR; OXADIAZOLES; PROTEIN-SERINE-THREONINE KINASES; REACTIVE OXYGEN SPECIES; STILBENES;

EID: 84941312523     PISSN: 00092797     EISSN: 18727786     Source Type: Journal    
DOI: 10.1016/j.cbi.2015.08.018     Document Type: Article

References (47)

1. J. Gerszon, A. Rodacka, and M. Puchała Antioxidant properties of resveratrol and its protective effects in neurodegenerative diseases Adv. Cell Biol. 4 2014 97 117
2. B. Fauconneau, P. Waffo-Teguo, F. Huguet, L. Barrier, A. Decendit, and J.-M. Merillon Comparative study of radical scavenger and antioxidant properties of phenolic compounds from Vitis vinifera cell cultures using in vitro tests Life Sci. 61 1997 2103 2110
3. P. Waffo-Teguo, M.E. Hawthorne, M. Cuendet, J.M. Mérillon, A.D. Kinghorn, J.M. Pezzuto, and R.G. Mehta Potential cancer-chemopreventive activities of wine stilbenoids and flavons extracted from grape (Vitis vinifera) cell cultures Nutr. Cancer 40 2001 173 179
4. C. Rius, M. Abu-Taha, C. Hermenegildo, L. Piqueras, J.-M. Cerda-Nicolas, A.C. Issekutz, L. Estañ, J. Cortijo, E.J. Morcillo, F. Orallo, and M.-J. Sanz Trans- but not cis-resveratrol impairs angiotensin-II-mediated vascular inflammation through inhibition of NF-κB activation and peroxisome proliferator-activated receptor-γ upregulation J. Immunol. 185 2010 3718 3727
5. B.C. Trela, and A.L. Waterhouse Resveratrol: isomeric molar absorptivities and stability J. Agric. Food Chem. 44 1996 1253 1257
6. T.T.Y. Wang, N.W. Schoene, Y.S. Kim, C.S. Mizuno, and A.M. Rimando Differential effects of resveratrol and its naturally occurring methylether analogs on cell cycle and apoptosis in human androgen-responsive LNCaP cancer cells Mol. Nutr. Food Res. 54 2010 335 344
7. B. Catalgol, S. Batirel, Y. Taga, and N.K. Ozer Resveratrol: French paradox revisited Front. Pharmacol. 3 2012 141
8. J.M. Pezzuto, T.P. Kondratyuk, and T. Ogas Resveratrol derivatives: a patent review (2009-2012) Expert Opin. Ther. Pat. 23 2013 1529 1546
9. F. Lolicato, A. Raudino, and D. Milardi Resveratrol interferes with the aggregation of membrane-bound human-IAPP: a molecular dynamics study Eur. J. Med. Chem. 92 2015 876 881
10. D. Milardi, M.F.M. Sciacca, L. Randazzo, A. Raudino, and C. La Rosa The role of calcium, lipid membranes and islet amyloid polypeptide in the onset of type 2 diabetes: innocent bystanders or partners in a crime? Front. Endocrinol. 5 2014 216 10.3389/fendo.2014.00216
11. M.F. Sciacca, R. Chillemi, S. Sciuto, M. Pappalardo, C. La Rosa, D. Grasso, and D. Milardi Interactions of two O-phosphorylresveratrol derivatives with model membranes Arch. Biochem. Biophys. 521 2012 111 116
12. R. Mishra, D. Sellin, D. Radovan, A. Gohlke, and R. Winter Inhibiting islet amyloid polypeptide fibril formation by the red wine compound resveratrol Chembiochem 10 2009 445 449
13. F. Evers, C. Jeworrek, S. Tiemeyer, K. Weise, D. Sellin, M. Paulus, B. Struth, M. Tolan, and R. Winter Elucidating the mechanism of lipid membrane-induced IAPP fibrillogenesis and its inhibition by the red wine compound resveratrol: a synchrotron X-ray reflectivity study J. Am. Chem. Soc. 131 2009 9516 9521
14. U. Švajger, and M. Jeras Anti-inflammatory effects of resveratrol and its potential use in therapy of immune-mediated diseases Int. Rev. Immunol. 31 2012 202 222
15. A.S. Mayhoub, L. Marler, T.P. Kondratyuk, E.-J. Park, J.M. Pezzuto, and M. Cushman Optimization of thiazole analogues of resveratrol for induction of NAD(P)H:quinone reductase 1 (QR1) Bioorg. Med. Chem. 20 2012 7030 7039
16. A.S. Mayhoub, L. Marler, T.P. Kondratyuk, E.-J. Park, J.M. Pezzuto, and M. Cushman Optimizing thiadiazole analogues of resveratrol versus three chemopreventive targets Bioorg. Med. Chem. 20 2012 510 520
17. S. He, and X. Yan From resveratrol to its derivatives: new sources of natural antioxidant Curr. Med. Chem. 20 2013 1005 1017
18. J.J. Heynekamp, W.M. Weber, L.A. Hunsaker, A.M. Gonzales, R.A. Orlando, L.M. Deck, and D.L. Jagt Substituted trans-stilbenes, including analogues of the natural product resveratrol, inhibit the human tumor necrosis factor alpha-induced activation of transcription factor nuclear factor kappaB J. Med. Chem. 49 2006 7182 7189
19. R. Csuk, S. Albert, and B. Siewert Synthesis and radical scavenging activities of resveratrol analogs Arch. Pharm. 346 2013 504 510
20. M. Cushman, D. Nagarathnam, D. Gopal, A.K. Chakraborti, C.M. Lin, and E. Hamel Synthesis and evaluation of stilbene and dihydrostilbene derivatives as potential anticancer agents that inhibit tubulin polymerization J. Med. Chem. 34 1991 2579 2588
21. T. Szekeres, M. Fritzer-Szekeres, P. Saiko, and W. Jäger Resveratrol and resveratrol analogues-structure-activity relationship Pharm. Res. 27 2010 1042 1048
22. A. Siddiqui, P. Dandawate, R. Rub, S. Padhye, S. Aphale, A. Moghe, A. Jagyasi, K. Venkateswara Swamy, B. Singh, A. Chatterjee, A. Ronghe, and H.K. Bhat Novel aza-resveratrol analogs: synthesis, characterization and anticancer activity against breast cancer cell lines Bioorg. Med. Chem. Lett. 23 2013 635 640
23. S.Y. Li, X.B. Wang, and L.Y. Kong Design, synthesis and biological evaluation of imine resveratrol derivatives as multi-targeted agents against Alzheimer's disease Eur. J. Med. Chem. 71 2014 36 45
24. R.S. Yao, X.Q. Lu, Q.X. Guan, L. Zheng, X. Lu, and B.F. Ruan Synthesis and biological evaluation of some novel resveratrol amide derivatives as potential anti-tumor agents Eur. J. Med. Chem. 62 2013 222 231
25. C. Zhao, and Z.Q. Liu Diaryl-1,2,4-oxadiazole antioxidants: synthesis and properties of inhibiting the oxidation of DNA and scavenging radicals Biochimie 95 2013 842 849
26. Ž. Jakopin, and M.S. Dolenc Recent advances in the synthesis of 1,2,4- and 1,3,4-oxadiazoles Curr. Org. Chem. 12 2008 850 898
27. J. Bostrom, A. Hogner, A. Llinas, E. Wellner, and A.T. Plowright Oxadiazoles in medicinal chemistry J. Med. Chem. 55 2012 1817 1830
28. GAMESS interface, ChemBio3D Ultra 13.0, CambridgeSoft.
29. T.A. Halgren Merck molecular force field.1. Basis, form, scope, parameterization, and performance of MMFF94 J. Comput. Chem. 17 1996 490 519
30. GOLD Suite, Version 5.2 is available from The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, U. K. www.ccdc.cam.ac.uk.
31. B. Berkowitz, D.B. Huang, F.E. Chen-Park, P.B. Sigler, and G. Ghosh The X-ray crystal structure of the NF-kappa B p50 p65 heterodimer bound to the interferon beta-kappa B site J. Biol. Chem. 277 2002 24694 24700
32. G. Jones, P. Willett, R.C. Glen, A.R. Leach, and R. Taylor Development and validation of a genetic algorithm for flexible docking J. Mol. Biol. 267 1997 727 748
33. PyMOL, Delano Scientific LLC, San Francisco, CA, http://pymol.sourceforge.net.
34. G. Agnihotri, R. Ukani, S.S. Malladi, H.J. Warshakoon, R. Balakrishna, X. Wang, and S.A. David Structure-activity relationships in nucleotide oligomerization domain 1 (nod1) agonistic gamma-glutamyldiaminopimelic acid derivatives J. Med. Chem. 54 2011 1490 1510
35. E.J. Calabrese, M.P. Mattson, and V. Calabrese Resveratrol commonly displays hormesis: occurrence and biomedical significance Hum. Exp. Toxicol. 29 2010 980 1015
36. Y.C. Oh, O.H. Kang, J.G. Choi, H.S. Chae, Y.S. Lee, O.O. Brice, H.J. Jung, S.H. Hong, Y.M. Lee, and D.Y. Kwon Anti-inflammatory effect of resveratrol by inhibition of IL-8 production in LPS-induced THP-1 cells Am. J. Chin. Med. 37 2009 1203 1214
37. V.M. Nayagam, X.K. Wang, Y.C. Tan, A. Poulsen, K.C. Goh, T. Ng, H.S. Wang, H.Y. Song, B.H. Ni, M. Entzeroth, and W. Stunkel SIRT1 modulating compounds from high-throughput screening as anti-inflammatory and insulin-sensitizing agents J. Biomol. Screen. 11 2006 959 967
38. Y.H. Feng, W.L. Zhou, Q.L. Wu, X.Y. Li, W.M. Zhao, and J.P. Zou Low dose of resveratrol enhanced immune response of mice Acta Pharmacol. Sin. 23 2002 893 897
39. P. Boscolo, A. del Signore, E. Sabbioni, M. Di Gioacchino, L. Di Giampaolo, M. Reale, P. Conti, R. Paganelli, and M. Giaccio Effects of resveratrol on lymphocyte proliferation and cytokine release Ann. Clin. Lab. Sci. 33 2003 226 231
40. G.A. Gualdoni, J.J. Kovarik, J. Hofer, F. Dose, M. Pignitter, D. Doberer, P. Steinberger, V. Somoza, M. Wolzt, and G.J. Zlabinger Resveratrol enhances TNF-alpha production in human monocytes upon bacterial stimulation BBA Gen. Subj. 1840 2014 95 105
41. C. Mulakayala, B. Babajan, P. Madhusudana, C.M. Anuradha, R.M. Rao, R.P. Nune, S.K. Manna, N. Mulakayala, and C.S. Kumar Synthesis and evaluation of resveratrol derivatives as new chemical entities for cancer J. Mol. Graph. Model. 41 2013 43 54
42. A. Benayahoum, H. Amira-Guebailia, and O. Houache A DFT method for the study of the antioxidant action mechanism of resveratrol derivatives J. Mol. Model. 19 2013 2285 2298
43. L.A. Stivala, M. Savio, F. Carafoli, P. Perucca, L. Bianchi, G. Maga, L. Forti, U.M. Pagnoni, A. Albini, E. Prosperi, and V. Vannini Specific structural determinants are responsible for the antioxidant activity and the cell cycle effects of resveratrol J. Biol. Chem. 276 2001 22586 22594
44. Z.H. Ren, L. Wang, J.H. Cui, Z.R. Huoc, J.R. Xue, H. Cui, Q.Q. Mao, and R.R. Yang Resveratrol inhibits NF-kappa B signaling through suppression of p65 and I kappa B kinase activities Pharmazie 68 2013 689 694
45. T. Ogas, T.P. Kondratyuk, and J.M. Pezzuto Resveratrol analogs: promising chemopreventive agents Ann. N. Y. Acad. Sci. 1290 2013 21 29
46. Y. Zong, L. Sun, B. Liu, Y.S. Deng, D. Zhan, Y.L. Chen, Y. He, J. Liu, Z.J. Zhang, J. Sun, and D. Lu Resveratrol inhibits LPS-induced MAPKs activation via activation of the phosphatidylinositol 3-kinase pathway in murine RAW 264.7 macrophage cells PLoS One 7 2012 e44107
47. X. Gao, D. Deeb, J. Media, G. Divine, H. Jiang, R.A. Chapman, and S.C. Gautam Immunomodulatory activity of resveratrol: discrepant in vitro and in vivo immunological effects Biochem. Pharmacol. 66 2003 2427 2435