Effects of lipoic acid, caffeic acid and a synthesized lipoyl-caffeic conjugate on human hepatoma cell lines

Molecules

Volumn 16, Issue 8, 2011, Pages 6365-6377

  Guerriero, Eliana ^a   Sorice, Angela ^a   Capone, Francesca ^a   Costantini, Susan ^a   Palladino, Pasquale ^a   D'Ischia, Marco ^b   Castello, Giuseppe ^a  

^a NATIONAL CANCER INSTITUTE   (Italy)

^b UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

Antioxidants; Caffeic acid; Cytokines; Lipoic acid

Indexed keywords

ANTINEOPLASTIC AGENT; ANTIOXIDANT; CAFFEIC ACID; CAFFEIC ACID DERIVATIVE; DRUG DERIVATIVE; INTERLEUKIN 10; INTERLEUKIN 1BETA; INTERLEUKIN 8; THIOCTIC ACID; TUMOR NECROSIS FACTOR ALPHA;

ARTICLE; BIOSYNTHESIS; CELL PROLIFERATION; CELL STRAIN HEPG2; CELL SURVIVAL; DRUG EFFECT; HUMAN; LIQUID CHROMATOGRAPHY; LIVER CELL CARCINOMA; LIVER TUMOR; MASS SPECTROMETRY; PATHOLOGY;

ANTINEOPLASTIC AGENTS; ANTIOXIDANTS; CAFFEIC ACIDS; CARCINOMA, HEPATOCELLULAR; CELL PROLIFERATION; CELL SURVIVAL; CHROMATOGRAPHY, LIQUID; HEP G2 CELLS; HUMANS; INTERLEUKIN-10; INTERLEUKIN-1BETA; INTERLEUKIN-8; LIVER NEOPLASMS; MASS SPECTROMETRY; THIOCTIC ACID; TUMOR NECROSIS FACTOR-ALPHA;

EID: 80052228524     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules16086365     Document Type: Article

References (48)

1. Parkin, D.M.; Bray, F.; Ferlay, J.; Pisani, P. Global cancer statistics, 2002. CA Cancer J. Clin. 2005, 55, 74-108.
2. Bosch, F.X.; Ribes, J.; Diaz, M.; Cleries, R. Primary liver cancer: worldwild incidence and trends. Gastroenterology 2004, 127, 5-16.
3. Edmondson, H.A.; Henderson, B.; Benton, B. Liver-cell adenomas associated with use of oral contraceptives. N. Engl. J. Med. 1976, 294, 470-472.
4. McGlynn, K.A.; London, W.T. Epidemiology and natural history of hepatocellular carcinoma. Best Pract. Res. Clin. Gastroenterol. 2005, 19, 3-23. (Pubitemid 40331495)
5. Bruix, J.; Sherman, M. Diagnosis of small HCC. Gastroenterology 2005, 129, 1364.
6. Stanner, S.A.; Hughes, J.; Kelly, C.N.; Buttriss, J. A review of the epidemiological evidence for the 'antioxidant hypothesis'. Public Health Nutr. 2004, 7, 407-422. (Pubitemid 39277053)
7. Halliwell, B. Free radicals and antioxidants -quo vadis? Trends Pharmacol. Sci. 2011, 32, 125-130.
8. Harman, D. Free-radical theory of aging. Increasing the functional life span. Ann. N.Y. Acad. Sci. 1994, 717, 1-15. (Pubitemid 24220869)
9. Simonian, N.A.; Coyle, J.T. Oxidative stress in neurodegenerative diseases. Annu. Rev. Pharmacol .Toxicol. 1996, 36, 83-106. (Pubitemid 26168695)
10. Stoner, G.D.; Mukhtar, H. Polyphenols as cancer chemopreventive agents. J. Cell. Biochem. Suppl. 1995, 22, 169-180.
11. Reed, L.J.; DeBusk, B.G.; Gunsalus, I.C.; Hornberger, C.S., Jr. Crystalline α-lipoic acid: A catalitic agent associated with pyruvate dehydrogenase. Science 1951, 114, 93-94.
12. Packer, L.; Witt, E.H.; Tritschler, H.J. alpha-Lipoic acid as a biological antioxidant. Free Radic. Biol. Med. 1995, 19, 227-250.
13. Bast, A.; Haenen, G.R. Lipoic acid: a multifunctional antioxidant. Biofactors 2003, 17, 207-13. (Pubitemid 37267155)
14. Farah, A.; Monteiro, M.; Donangelo, C.M.; Lafay, S. Chlorogenic acids from green coffee extract are highly bioavailable in humans. J. Nutr. 2008, 138, 2309-2315.
15. Sato, Y.; Itagaki, S.; Kurokawa, T.; Ogura, J.; Kobayashi, M.; Hirano, T.; Sugawara, M.; Iseki, K. In vitro and in vivo antioxidant properties of chlorogenic acid and caffeic acid. Int. J. Pharm. 2011, 17, 403:136-403:138.
16. Gailit, J. Restoring free sulfhydryl groups in synthetic peptides. Anal. Biochem. 1993, 214, 334-335. (Pubitemid 23300396)
17. Fulcrand, H.; Cheminat, A.; Brouillard, R.; Cheynier, V. Characterization of compounds obtained by chemical oxidation of caffeic acid in acidic condition. Phytochemistry 1994, 35, 499-505.
18. Bassil, D.; Makris, D.P.; Kefalas, P. Oxidation of caffeic acid in the presence of L-cysteine: isolation of 2-S-cysteinylcaffeic acid and evaluation of its antioxidant properties. Food Res. Int. 2005, 38, 395-402. (Pubitemid 40328601)
19. Cilliers, J.J.L.; Singleton, V.L. Caffeic acid Autoxidation and the effects of Thiols. J. Agric. Food Chem. 1990, 38, 1789-1796.
20. Simbula, G.; Columbano, A.; Ledda-Columbano, G.M.; Sanna, L.; Deidda, M.; Diana, A.; Pibiri, M. Increased ROS generation and p53 activation in α-lipoic acid-induced apoptosis of hepatoma cells. Apoptosis 2007, 12, 113-123. (Pubitemid 46009508)
21. Chung, T.W.; Moon, S.K.; Chang, Y.C.; Ko, J.H.; Lee, Y.C.; Cho, G.; Kim, S.H.; Kim, J.G.; Kim, C.H. Novel and therapeutic effect of caffeic acid and caffeic acid phenyl ester on hepatocarcinoma cells: Complete regression of hepatoma growth and metastasis by dual mechanism. FASEB J. 2004, 18, 1670-1681. (Pubitemid 39463706)
22. Won, C.; Lee, C.S.; Lee, J.K.; Kim, T.J.; Lee, K.H.; Yang, Y.M.; Kim, Y.N.; Ye, S.K.; Chung, M.H. CADPE suppresses cyclin D1 expression in hepatocellular carcinoma by blocking IL-6-induced STAT3 activation. Anticancer Res. 2010, 30, 481-488.
23. Parekh, P.; Rao, K.V. Overexpression of cyclin D1 is associated with elevated levels of MAP kinases, Akt and Pak1 during diethylnitrosamine-induced progressive liver carcinogenesis. Cell. Biol. Int. 2007, 31, 35-43. (Pubitemid 46124028)
24. Jabari, S.; Meissnitzer, M.; Quint, K.; Gahr, S.; Wissniowski, T.; Hahn, E.G.; Neureiter, D.; Ocker, M. Cellular plasticity of trans- and dedifferentiation markers in human hepatoma cells in vitro and in vivo. Int. J. Oncol. 2009, 35, 69-80.
25. Hussain, S.P.; Schwank, J.; Staib, F.; Wang, X.W.; Harris, C.C. TP53 mutations and hepatocellular carcinoma: insights into the etiology and pathogenesis of liver cancer. Oncogene 2007, 26, 2166-2176. (Pubitemid 46536641)
26. Capone, F.; Costantini, S.; Guerriero, E.; Calemma, R.; Napolitano, M.; Scala, S.; Izzo, F.; Castello, G. Serum cytokine levels in patients with hepatocellular carcinoma. Eur. Cytokine Netw. 2010, 21, 99-104.
27. Costantini, S.; Capone, F.; Guerriero, E.; Maio, P.; Colonna, G.; Castello, G. Serum cytokine levels as putative prognostic markers in the progression of chronic HCV hepatitis to cirrhosis. Eur. Cytokine Netw. 2010, 21, 251-256.
28. Stonãns, I.; Stonãne, E.; Russwurm, S.; Deigner, H.P.; Böhm, K.J.; Wiederhold, M.; Jäger, L.; Reinhart, K HepG2 human hepatoma cells express multiple cytokine genes. Cytokine 1999, 11, 151-156. (Pubitemid 29116554)
29. Shin, E.C.; Choi, Y.H.; Kim, J.S.; Kim, S.J.; Park, J.H. Expression patterns of cytokines and chemokines genes in human hepatoma cells. Yonsei Med. J. 2002, 43, 657-664. (Pubitemid 35282889)
30. Liu, Z.G.; Han, J. Cellular responses to tumor necrosis factor. Curr. Issues Mol. Biol. 2001, 3, 79-90. (Pubitemid 33061771)
31. Ataseven, H.; Bahcecioglu, I.H.; Kuzu, N.; Yalniz, M.; Celebi, S.; Erensoy, A.; Ustundag, B. The levels of ghrelin, leptin, TNF-alpha, and IL-6 in liver cirrhosis and hepatocellular carcinoma due to HBV and HDV infection. Mediators Inflamm. 2006, 2006, 78380.
32. Fabregat, I. Dysregulation of apoptosis in hepatocellular carcinoma cells. World J. Gastroenterol. 2009, 15, 513-520.
33. Natarajan, K.; Singh, S.; Burke, T.R., Jr.; Grunberger, D.; Aggarwal, B.B. Caffeic acid phenethyl ester is a potent and specific inhibitor of activation of nuclear transcription factor NF-kappa B. Proc. Natl. Acad. Sci. USA 1996, 93, 9090-9095. (Pubitemid 26282023)
34. Zhang, W.J.; Frei, B. Alpha-lipoic acid inhibits TNF-alpha-induced NF-kappaB activation and adhesion molecule expression in human aortic endothelial cells. FASEB J. 2001, 15, 2423-2432. (Pubitemid 33063170)
35. Abdel-Latif, M.M.; Windle, H.J.; Homasany, B.S.; Sabra, K.; Kelleher, D. Caffeic acid phenethyl ester modulates Helicobacter pylori-induced nuclear factor-kappa B and activator protein-1 expression in gastric epithelial cells. Br. J. Pharmacol. 2005, 146, 1139-1147. (Pubitemid 41785325)
36. Jung, W.K.; Choi, I.; Lee, D.Y.; Yea, S.S.; Choi, Y.H.; Kim, M.M.; Park, S.G.; Seo, S.K.; Lee, S.W.; Lee, C.M.; et al. Caffeic acid phenethyl ester protects mice from lethal endotoxin shock and inhibits lipopolysaccharide- induced cyclooxygenase-2 and inducible nitric oxide synthase expression in RAW 264.7 macrophages via the p38/ERK and NF-kappaB pathways. Int. J. Biochem. Cell. Biol. 2008, 40, 2572-2582.
37. Song, J.J.; Cho, J.G.; Hwang, S.J.; Cho, C.G.; Park, S.W.; Chae, S.W. Inhibitory effect of caffeic acid phenethyl ester (CAPE) on LPS-induced inflammation of human middle ear epithelial cells. Acta Otolaryngol. 2008, 128, 1303-1307.
38. Akiba, J.; Yano, H.; Ogasawara, S.; Higaki, K.; Kojiro, M. Expression and function of interleukin-8 in human hepatocellular carcinoma. Int. J. Oncol. 2001, 18, 257-264.
39. Kubo, F.; Ueno, S.; Hiwatashi, K.; Sakoda, M.; Kawaida, K.; Nuruki, K.; Aikou, T. Interleukin 8 in human hepatocellular carcinoma correlates with cancer cell invasion of vessels but not with tumor angiogenesis. Ann. Surg. Oncol. 2005, 12, 800-807. (Pubitemid 41355932)
40. Moon, M.K.; Lee, Y.J.; Kim, J.S.; Kang, D.G.; Lee, H.S. Effect of caffeic acid on tumor necrosis factor-alpha-induced vascular inflammation in human umbilical vein endothelial cells. Biol. Pharm. Bull. 2009, 32, 1371-1377.
41. Zhao, Z.; Shin, H.S.; Satsu, H.; Totsuka, M.; Shimizu, M. 5-caffeoylquinic acid and caffeic acid down-regulate the oxidative stress- and TNF-alpha-induced secretion of interleukin-8 from Caco-2 cells. J. Agric. Food Chem. 2008, 56, 3863-3868. (Pubitemid 351860195)
42. Fitzpatrick, L.R.; Wang, J.; Le, T. Caffeic acid phenethyl ester, an inhibitor of nuclear factor-kappaB, attenuates bacterial peptidoglycan polysaccharide-induced colitis in rats. J. Pharmacol. Exp. Ther. 2001, 299, 915-920. (Pubitemid 33104959)
43. Zhang, T.; Guo, C.J.; Li, Y.; Douglas, S.D.; Qi, X.X.; Song, L.; Ho, W.Z. Interleukin-1beta induces macrophage inflammatory protein-1beta expression in human hepatocytes. Cell. Immunol. 2003, 226, 45-53. (Pubitemid 38121297)
44. Santiago-Lomelí, M.; Gómez-Quiroz, L.E.; Ortíz-Ortega, V.M.; Kershenobich, D.; Gutiérrez-Ruiz, M.C. Differential effect of interleukin-10 on hepatocyte apoptosis. Life Sci. 2005, 76, 2569-2579.
45. Hsia, C.Y.; Huo, T.I.; Chiang, S.Y.; Lu, M.F.; Sun, C.L.; Wu, J.C.; Lee, P.C.; Chi, C.W.; Lui, W.Y.; Lee, S.D. Evaluation of interleukin-6, interleukin-10 and human hepatocyte growth factor as tumor markers for hepatocellular carcinoma. Eur. J. Surg. Oncol. 2007, 33, 208-212.
46. Delhem, N.; Cottrez, F.; Carpentier, A.; Miroux, C.; Moralès, O.; François, V.; Groux, H.; Auriault, C.; Pancré, V. Role of the Regulatory T lymphocytes in hepatitis C fibrosis progression. Bull. Cancer 2008, 95, 1029-1038.
47. Bruzzese, F.; Di Gennaro, E.; Avallone, A.; Pepe, S.; Arra, C.; Caraglia, M.; Tagliaferri, P.; Budillon, A. Synergistic antitumor activity of epidermal growth factor receptor tyrosine kinase inhibitor gefitinib and IFN-alpha in head and neck cancer cells in vitro and in vivo. Clin. Cancer Res. 2006, 12, 617-625. (Pubitemid 43166157)
48. inhibitor gefitinib and IFN-alpha in head and neck cancer cells in vitro and in vivo. Clin. Cancer Res. 2006, 12, 617-625. 48. Tirosh, O.; Sen, C.K.; Roy, S.; Kobayashi, M.S.; Packer, L. Neuroprotective effects of alpha-lipoic acid and its positively charged amide analogue. Free Radic. Biol. Med. 1999, 26, 1418-1426. (Pubitemid 29308022)