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

Journal of Medicinal Chemistry

Volumn 49, Issue 24, 2006, Pages 7182-7189

  Heynekamp, Justin J ^a   Weber, Waylon M ^a   Hunsaker, Lucy A ^b   Gonzales, Amanda M ^b   Orlando, Robert A ^b   Deck, Lorraine M ^a   Vander Jagt, David L ^b  

^a UNIVERSITY OF NEW MEXICO   (United States)

^b UNIVERSITY OF NEW MEXICO SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOOXYGENASE 2; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; LIPOPOLYSACCHARIDE; NATURAL PRODUCT; RESVERATROL; RESVERATROL DERIVATIVE; STILBENE DERIVATIVE; TRANSCRIPTION FACTOR; TUMOR NECROSIS FACTOR ALPHA;

ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; ARTICLE; CELL STRAIN HEK293; CONTROLLED STUDY; DOSE RESPONSE; DRUG MECHANISM; DRUG POTENCY; DRUG STRUCTURE; HUMAN; HUMAN CELL; IC 50; MICROGLIA;

ANTIOXIDANTS; CELL LINE; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLOOXYGENASE 2 INHIBITORS; HUMANS; NF-KAPPA B; STEREOISOMERISM; STILBENES; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR NECROSIS FACTOR-ALPHA;

EID: 33845367887     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm060630x     Document Type: Article

References (43)

1. Yamamoto, Y.; Gaynor, R. B. Therapeutic potential of inhibition of the NF-kappaB pathway in the treatment of inflammation and cancer. J. Clin. Invest. 2001, 107, 135-142.
2. Kim, H. J.; Hawke, N.; Baldwin, A. S. NF-κB and IKK as therapeutic targets in cancer. Cell Death Different. 2006, advanced online publication.
3. Kaltschmidt, B.; Widera, D.; Kaltschmidt, C. Signaling via NF-κB in the nervous system. Biochim. Biophys. Acta 2005, 1745, 287-299.
4. Viatour, P.; Merville, M-P.; Bours, V.; Chariot, A. Phosphorylation of NF-kappaB and IkappaB proteins: implications in cancer and inflammation. Trends Biochem. Sci. 2005, 30, 43-52.
5. Kumar, A.; Takada, Y.; Boriek, A. M.; Aggarwal, B. B. Nuclear factor-κB: its role in health and disease. J. Mol. Med. 2004, 82, 434-448.
6. Hiscott, J.; Kwon, H.; Genin, P. Hostile takeovers: viral appropriation of the NF-kappaB pathway. J. Clin. Invest. 2001, 107, 143-151.
7. Barkett, M.; Gilmore, T. Control of apoptosis by Rel/NF-kappaB transcription factors. Oncogene 1999, 18, 6910-6924.
8. Karin, M.; Greten, F. R. NF-κB: linking inflammation and immunity to cancer development and progression. Nature Rev. Immunol. 2005, 5, 749-759.
9. Herrmann, O.; Baumann, B.; de Lorenzi, R.; Muhammad, S.; Zhang, W.; Kleesiek, J.; Malfertheiner, M.; Kohrmann, M.; Potrovita, I.; Maegele, I.; Beyer, C.; Burke, J. R.; Hasan, M. T.; Bujard, H.; Wirth, T.; Pasparakis, M.; Schwaninger, M. IKK mediates ischemia-induced neuronal death. Nat. Med. 2005, 11, 1322-1329.
10. Schmitz, M. L.; Mattioli, I.; Buss, H.; Kracht, M. NF-κB: a multifaceted transcription factor regulated at several levels. Chem-BioChem 2004, 5, 1348-1358.
11. http://people.bu.edu/gilmore/nf-kb/inhibitors
12. Dore, S. Unique properties of polyphenol stilbenes in the brain: more than direct antioxidant actions; gene/protein regulatory activity. Neurosignals 2005, 14, 61-70.
13. Kundu, J. K.; Surh, Y-J. Molecular basis of chemoprevention by resveratrol: NF-κB and AP-1 as potential targets. Mut. Res. 2004, 555, 65-80.
14. Shimizu, M.; Weinstein, B. Modulation of signal transduction by tea catechins and related phytochemicals. Mut. Res. 2005, 591, 147-160.
15. Renaud, S.; de Lorgeril, M. Wine, platelets, and the French paradox for coronary heart disease. Lancet 1992, 339, 1523-1526.
16. Jang, M.; Cai, L.; Udeani, G. O.; Slowing, K. V.; Thomas, C. F.; Beecher, C. W.; Fong, H. H.; Farnsworth, N. R.; Kinghorn, A. D.; Mehta, R. G.; Moon, R. C.; Pezzuto, J. M. Cancer chemopreventive activity of resveratrol, a natural product derived from grapes. Science 1997, 275, 218-220.
17. Ovesna, Z.; Horvathova-Kozics, K. Structure-activity relationship of trans-resveratrol and its analogs. Neoplasma 2005, 52, 450-455.
18. Orallo, F. Comparative studies of the antioxidant effects of cis- and trans-resveratrol. Curr. Med. Chem. 2006, 13, 87-98.
19. Lu, M.; Cai, Y. J.; Fang, J. G.; Zhou, Y. L.; Liu, Z. L.; Wu, L. M. Efficiency and structure-activity relationship of the antioxidant action of resveratrol and its analogs. Pharmazie 2002, 57, 474-478.
20. Stojanovic, S.; Sprinz, H.; Brede, O. Efficiency and mechanism of the antioxidant action of trans-resveratrol and its analogues in the radical liposome oxidation. Arch. Biochem. Biophys. 2001, 391, 79-89.
21. Stivala, L. A.; Savio, M.; Carafoli, F.; Perucca, P.; Bianchi, L.; Maga, G.; Forti, L.; Pagnoni, U. M.; Albini, A.; Prosperi, E.; Vannini, V. Specific structural determinants are responsible for the antioxidant activity and the cell cycle effects of resveratrol. J. Biol. Chem. 2001, 276, 22586-22594.
22. Chung, M. I.; Teng, C. M.; Cheng, K. L.; Ko, F. N.; Lin, C. N. An antiplatelet principle of Veratrum formosanum. Planta Med. 1992, 58, 274-276.
23. Fremont, L.; Gozzelino, M. T.; Linard, A. Response of plasma lipids to dietary cholesterol and wine polyphenols in rats fed polyunsaturated fat diets. Lipids 2000, 35, 991-999.
24. Murias, M.; Handler, N.; Erker, T.; Pleban, K.; Ecker, G.; Saiko, P.; Szekeres, T.; Jager, W. Resveratrol analogues as selective cyclooxygenase-2 inhibitors: synthesis and structure-activity relationship. Bioorg. Med. Chem. 2004, 12, 5571-5578.
25. Shay, N. F.; Banz, W. J. Regulation of gene transcription by botanicals: novel regulatory mechanisms. Annu. Rev. Nutr. 2005, 25, 297-315.
26. Juan, S. H.; Cheng, T. H.; Lin, H. C.; Chu, Y. L.; Lee, W. S. Mechanism of concentration-dependent induction of heme oxygenase-1 by resveratrol in human aortic smooth muscle cells. Biochem. Pharmacol. 2005, 69, 41-48.
27. Kundu, J. K.; Shin, Y. K.; Surh, Y. J. Resveratrol inhibits phorbol ester-induced expression of COX-2 and activation of NF-kappaB in mouse skin by blocking IkappaB activity. Carcinogenesis 2006, Epub ahead of print.
28. Lee, B.; Moon, S-K. Resveratrol inhibits TNF-α-induced proliferation and matrix metalloproteinase expression in human vascular smooth muscle cells. J. Nutr. 2005, 135, 2767-2773.
29. Liao, H. F.; Kuo, C. D.; Yang, Y. C.; Lin, C. P.; Tai, H. C.; Chen, Y. Y.; Chen, Y. J. Resveratrol enhances radiosensitivity of human non-small cell lung cancer NCI-H838 cells accompanied by inhibition of nuclear factor-kappa B activation. J. Radiat. Res. (Tokyo) 2005, 46, 387-393.
30. Bi, X. L.; Yang, J. Y.; Dong, Y. X.; Wang, J. M.; Cui, Y. H.; Ikeshima, T.; Zhao, Y. Q.; Wu, C. F. Resveratrol inhibits nitric oxide and TNF-alpha production by lipopolysaccharide-activated microglia. Int. Immunopharmacol. 2005, 5, 185-193.
31. Bellucci, G.; Chiappe, C.; Lo, Moro, G. Crown ether catalyzed stereospecific synthesis of Z- and E-stilbenes by Wittig reaction in a solid-liquid two-phase system. Tetrahedron Lett. 1996, 37, 4225-4228.
32. Lion, C. J.; Matthews, C. S.; Stevens, M. F. G.; Westwell, A. D. Synthesis, antitumor evaluation, and apoptosis-inducing activity of hydroxylated (E)-stilbenes. J. Med. Chem. 2005, 48, 1292-1295.
33. Kang, G.; Kong, P. J.; Yuh, Y. J.; Lim, S. Y.; Yim, S. V.; Chun, W.; Kim, S. S. Curcumin suppresses lipopolysaccharide-induced cyclooxygenase-2 expression by inhibiting activator protein 1 and nuclear factor kappab bindings in BV2 microglial cells. J. Pharmacol. Sci. 2004, 94, 325-328.
34. Wieder, T.; Prokop, A.; Bagci, B.; Essmann, F.; Bernicke, D.; Schulze-Osthoff, K.; Dorken, B.; Schmalz, H. G.; Daniel, P. T.; Henze, G. Piceatannol, a hydroxylated analog of the chemopreventive agent resveratrol, is a potent inducer of apoptosis in the lymphoma cell line BJAB and in primary, leukemic lymphoblasts. Leukemia 2001, 15, 1735-1742.
35. Ashikawa, K.; Majumdar, S.; Banerjee, S.; Bharti, A. C.; Shishodia, S.; Aggarwal, B. B. Piceatannol inhibits TNF-induced NF-κB activation and NF-κB-mediated gene expression through suppression of IκBα kinase and p65 phosphorylation. J. Immunol. 2002, 169, 6490-6497.
36. Rimando, A. M.; Cuendet, M.; Desmarchelier, C.; Mehta, R. G.; Pezzuto, J. M.; Duke, S. O. Cancer chemopreventive and antioxidant activities of pterostilbene, a naturally occurring analogue of resveratrol. J. Agric. Food Chem. 2002, 50, 3453-3457.
37. Tolomeo, M.; Grimaudo, S.; Di, Cristina, A.; Roberti, M.; Pizzirani, D.; Meli, M.; Dusonchet, L.; Gebbia, N.; Abbadessa, V.; Crosta, L.; Barucchello, R.; Grisolia, G.; Invidiata, F.; Simoni, D. Pterostilbene and 3′- hydroxypterostilbene are effective apoptosis-inducing agents in MDR and BCR-ABL-expressing leukemia cells. Int. J. Biochem. Cell. Biol. 2005, 37, 1709-1726.
38. Mann, S. K.; Mukhopadhyay, A.; Aggarwal, B. B. Resveratrol suppresses TNF-induced activation of nuclear transcription factors NF-κB, activator protein-1, and apoptosis: potential role of reactive oxygen intermediates and lipid peroxidation. J. Immunol. 2000, 164, 6509-6519.
39. Sizemore, N.; Lerner, N.; Dombrowski, N.; Sakurai, H.; Stark, G. R. Distinct roles of the IκB kinase α and β in liberating nuclear factor κB (NF-κB) from IκB and in phosphorylating the p65 subunit of NF-κB. J. Biol. Chem. 2002, 277, 3863-3869.
40. Schlesier, K.; Harwat, M.; Bohm, V.; Bitsch, R. Assessment of antioxidant activity by using different in vitro methods. Free Rad. Res. 2002, 36, 177-187.
41. Re, R.; Pellegrini, N.; Proteggente, A.; Pannala, A.; Yang, M.; Rice-Evans, C. Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Rad. Biol. Med. 1999, 26, 1231-1237.
42. Benzie, I. F.; Strain, J. J. Ferric reducing/antioxidant power assay: direct measure of total antioxidant activity of biological fluids and modified version for simultaneous measurement of total antioxidant power and ascorbic acid concentrations. Methods Enzymol. 1999, 299, 15-27.
43. Begum, S. D.; Parthasarathi, J. A convenient synthesis of homobutein. Ind. J. Chem. Sect. B 1988, 27B, 464.