Colon-targeted delivery of piceatannol enhances anti-colitic effects of the natural product: Potential molecular mechanisms for therapeutic enhancement

Drug Design, Development and Therapy

Volumn 9, Issue , 2015, Pages 4247-4258

  Yum, Soohwan ^a   Jeong, Seongkeun ^a   Lee, Sunyoung ^a   Nam, Joon ^a   Kim, Wooseong ^a   Yoo, Jin Wook ^a   Kim, Min Soo ^a   Lee, Bok Luel ^a   Jung, Yunjin ^a  

^a Pusan National University   (South Korea)

Author keywords

Colitis; Colon targeted delivery; Multitarget; Piceatannol; Polypharmacology

Indexed keywords

CELECOXIB; HYPOXIA INDUCIBLE FACTOR 1; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; PICEATANNOL; PROTEIN NF E2 P45 RELATED FACTOR 2; QUERCETIN; TRANSCRIPTION FACTOR NF E2 P45 SUBUNIT; UNCLASSIFIED DRUG; 3,3',4,5'-TETRAHYDROXYSTILBENE; ANTIINFLAMMATORY AGENT; AUTACOID; BIOLOGICAL MARKER; GASTROINTESTINAL AGENT; GELATIN; MICROCAPSULE; STILBENE DERIVATIVE; TRINITROBENZENESULFONIC ACID;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTICOLITIC ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; COLITIS; COLON CARCINOMA; COLON TARGETED DELIVERY; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG DELIVERY SYSTEM; DRUG TARGETING; GENE TARGETING; HCT116 CELL LINE; HUMAN; HUMAN CELL; NONHUMAN; PROCESS OPTIMIZATION; RAT; ANIMAL; CHEMICALLY INDUCED; CHEMISTRY; COLON; COMPARATIVE STUDY; DISEASE MODEL; DRUG EFFECTS; GENE EXPRESSION REGULATION; GENETIC TRANSFECTION; GENETICS; HCT 116 CELL LINE; MALE; MEDICINAL CHEMISTRY; METABOLISM; MICROCAPSULE; MOUSE; ORAL DRUG ADMINISTRATION; PATHOLOGY; PHARMACEUTICS; PROCEDURES; RAW 264.7 CELL LINE; RECTAL DRUG ADMINISTRATION; SIGNAL TRANSDUCTION; SPRAGUE DAWLEY RAT;

ADMINISTRATION, ORAL; ADMINISTRATION, RECTAL; ANIMALS; ANTI-INFLAMMATORY AGENTS; BIOMARKERS; CAPSULES; CHEMISTRY, PHARMACEUTICAL; COLITIS; COLON; DISEASE MODELS, ANIMAL; GASTROINTESTINAL AGENTS; GELATIN; GENE EXPRESSION REGULATION; HCT116 CELLS; HUMANS; INFLAMMATION MEDIATORS; MALE; MICE; RATS, SPRAGUE-DAWLEY; RAW 264.7 CELLS; SIGNAL TRANSDUCTION; STILBENES; TECHNOLOGY, PHARMACEUTICAL; TRANSFECTION; TRINITROBENZENESULFONIC ACID;

EID: 84939816399     PISSN: None     EISSN: 11778881     Source Type: Journal    
DOI: 10.2147/DDDT.S88670     Document Type: Article

References (30)

1. Cader MZ, Kaser A. Recent advances in inflammatory bowel disease: mucosal immune cells in intestinal inflammation. Gut. 2013;62(11):1653–1664.
2. Ardizzone S, Porro GB. Inflammatory bowel disease: new insights into pathogenesis and treatment. J Intern Med. 2002;252(6):475–496.
3. Ko JK, Auyeung KK. Inflammatory bowel disease: etiology, pathogenesis and current therapy. Curr Pharm Des. 2014;20(7):1082–1096.
4. Feagan BG. Maintenance therapy for inflammatory bowel disease. Am J Gastroenterol. 2003;98(12 Suppl):S6–S17.
5. Atreya I, Atreya R, Neurath MF. NF-kappaB in inflammatory bowel disease. J Intern Med. 2008;263(6):591–596.
6. Khor TO, Huang MT, Kwon KH, Chan JY, Reddy BS, Kong AN. Nrf2-deficient mice have an increased susceptibility to dextran sulfate sodium-induced colitis. Cancer Res. 2006;66(24):11580–11584.
7. Karhausen J, Furuta GT, Tomaszewski JE, Johnson RS, Colgan SP, Haase VH. Epithelial hypoxia-inducible factor-1 is protective in murine experimental colitis. J Clin Invest. 2004;114(8):1098–1106.
8. Kim J, Cha YN, Surh YJ. A protective role of nuclear factor-erythroid 2-related factor-2 (Nrf2) in inflammatory disorders. Mutat Res. 2010;690(1–2):12–23.
9. Robinson A, Keely S, Karhausen J, Gerich ME, Furuta GT, Colgan SP. Mucosal protection by hypoxia-inducible factor prolyl hydroxylase inhibition. Gastroenterology. 2008;134(1):145–155.
10. Cummins EP, Seeballuck F, Keely SJ, et al. The hydroxylase inhibitor dimethyloxalylglycine is protective in a murine model of colitis. Gastroenterology. 2008;134(1):156–165.
11. Piotrowska H, Kucinska M, Murias M. Biological activity of piceatannol: Leaving the shadow of resveratrol. Mutat Res. 2011.
12. Ashikawa K, Majumdar S, Banerjee S, Bharti AC, Shishodia S, Aggarwal BB. Piceatannol inhibits TNF-induced NF-kappaB activation and NF-kappaB-mediated gene expression through suppression of IkappaBalpha kinase and p65 phosphorylation. J Immunol. 2002;169(11):6490–6497.
13. Son PS, Park SA, Na HK, Jue DM, Kim S, Surh YJ. Piceatannol, a catechol-type polyphenol, inhibits phorbol ester-induced NF-{kappa}B activation and cyclooxygenase-2 expression in human breast epithelial cells: cysteine 179 of IKK{beta} as a potential target. Carcinogenesis. 2010;31(8):1442–1449.
14. Lee HH, Park SA, Almazari I, Kim EH, Na HK, Surh YJ. Piceatannol induces heme oxygenase-1 expression in human mammary epithelial cells through activation of ARE-driven Nrf2 signaling. Arch Biochem Biophys. 2010;501(1):142–150.
15. Yum S, Doh HJ, Hong S, et al. Piceatannol, a hydroxystilbene natural product, stabilizes HIF-1alpha protein by inhibiting HIF prolyl hydroxylase. Eur J Pharmacol. 2013;699(1–3):124–131.
16. Youn J, Lee JS, Na HK, Kundu JK, Surh YJ. Resveratrol and piceatannol inhibit iNOS expression and NF-kappaB activation in dextran sulfate sodium-induced mouse colitis. Nutr Cancer. 2009;61(6):847–854.
17. Kim YH, Kwon HS, Kim DH, et al. Piceatannol, a stilbene present in grapes, attenuates dextran sulfate sodium-induced colitis. Int Immunopharmacol. 2008;8(12):1695–1702.
18. Roupe KA, Yanez JA, Teng XW, Davies NM. Pharmacokinetics of selected stilbenes: rhapontigenin, piceatannol and pinosylvin in rats. J Pharm Pharmacol. 2006;58(11):1443–1450.
19. Jung Y, Kim YM. What should be considered on design of a colon-specific prodrug? Expert Opin Drug Deliv. 2010;7(2):245–258.
20. Kim H, Kim W, Yum S, et al. Caffeic acid phenethyl ester activation of Nrf2 pathway is enhanced under oxidative state: structural analysis and potential as a pathologically targeted therapeutic agent in treatment of colonic inflammation. Free Radic Biol Med. 2013;65:552–562.
21. Lee Y, Shin DH, Kim JH, et al. Caffeic acid phenethyl ester-mediated Nrf2 activation and IkappaB kinase inhibition are involved in NFkappaB inhibitory effect: structural analysis for NFkappaB inhibition. Eur J Pharmacol. 2010;643(1):21–28.
22. Andrews NC, Faller DV. A rapid micropreparation technique for extraction of DNA-binding proteins from limiting numbers of mammalian cells. Nucleic Acids Res. 1991;19(9):2499.
23. Morris GP, Beck PL, Herridge MS, Depew WT, Szewczuk MR, Wallace JL. Hapten-induced model of chronic inflammation and ulceration in the rat colon. Gastroenterology. 1989;96(3):795–803.
24. Yano H, Hirayama F, Kamada M, Arima H, Uekama K. Colon-specific delivery of prednisolone-appended alpha-cyclodextrin conjugate: alleviation of systemic side effect after oral administration. J Control Release. 2002;79(1–3):103–112.
25. Son MW, Ko JI, Doh HM, et al. Protective effect of taurine on TNBS-induced inflammatory bowel disease in rats. Arch Pharm Res. 1998;21(5):531–536.
26. Hong S, Yum S, Yoo HJ, et al. Colon-targeted cell-permeable NFkappaB inhibitory peptide is orally active against experimental colitis. Mol Pharm. 2012;9(5):1310–1319.
27. Yamaoka T, Makita Y, Sasatani H, Kim SI, Kimura Y. Linear type azo-containing polyurethane as drug-coating material for colon-specific delivery: its properties, degradation behavior, and utilization for drug formulation. J Control Release. 2000;66(2–3):187–197.
28. Lee Y, Kim J, Kim H, et al. N-succinylaspart-1-yl celecoxib is a potential colon-specific prodrug of celecoxib with improved therapeutic properties. J Pharm Sci. 2012.
29. Kim H, Kong H, Choi B, et al. Metabolic and pharmacological properties of rutin, a dietary quercetin glycoside, for treatment of inflammatory bowel disease. Pharm Res. 2005;22(9):1499–1509.
30. Anighoro A, Bajorath J, Rastelli G. Polypharmacology: challenges and opportunities in drug discovery. J Med Chem. 2014.