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Orignal Articles

A Novel Prodrug of 4′-Geranyloxy-Ferulic Acid Suppresses Colitis-Related Colon Carcinogenesis in Mice

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Pages 675-684 | Received 19 Dec 2007, Accepted 18 Feb 2008, Published online: 12 Sep 2008

REFERENCES

  • Centre , W M . 2006 . Cancer , Geneva, , Switzerland : WHO . Fact sheet No. 297.
  • Balkwill , F and Mantovani , A . 2001 . Inflammation and cancer: back to Virchow? . Lancet , 357 : 539 – 545 .
  • Rubin , D T and Parekh , N . 2006 . Colorectal cancer in inflammatory bowel disease: molecular and clinical considerations . Curr Treat Options Gastroenterol , 9 : 211 – 220 .
  • Chan , E P and Lichtenstein , G R . 2006 . Chemoprevention: risk reduction with medical therapy of inflammatory bowel disease . Gastroenterol Clin North Am , 35 : 675 – 712 .
  • Tanaka , T . 1997 . Effect of diet on human carcinogenesis . Crit Rev Oncol Hematol , 25 : 73 – 95 .
  • Tanaka , T . 1997 . Chemoprevention of human cancer: biology and therapy . Crit Rev Oncol Hematol , 25 : 139 – 174 .
  • Aggarwal , B B , Ichikawa , H , Garodia , P , Weerasinghe , P Sethi , G . 2006 . From traditional Ayurvedic medicine to modern medicine: identification of therapeutic targets for suppression of inflammation and cancer . Expert Opin Ther Targets , 10 : 87 – 118 .
  • Tanaka , T , Kojima , T , Kawamori , T , Wang , A Suzui , M . 1993 . Inhibition of 4-nitroquinoline-1-oxide-induced rat tongue carcinogenesis by the naturally occurring plant phenolics caffeic, ellagic, chlorogenic, and ferulic acids . Carcinogenesis , 14 : 1321 – 1325 .
  • Hirose , M , Takahashi , S , Ogawa , K , Futakuchi , M Shirai , T . 1999 . Chemoprevention of heterocyclic amine-induced carcinogenesis by phenolic compounds in rats . Cancer Lett , 143 : 173 – 178 .
  • Hudson , E A , Dinh , P A , Kokubun , T , Simmonds , M S and Gescher , A . 2000 . Characterization of potentially chemopreventive phenols in extracts of brown rice that inhibit the growth of human breast and colon cancer cells . Cancer Epidemiol Biomarkers Prev , 9 : 1163 – 1170 .
  • Curini , M , Epifano , F , Genovese , S , Marcotullio , M C and Menghini , L . 2006 . 3-(4′-geranyloxy-3′-methoxyphenyl)-2-trans propenoic acid: a novel promising cancer chemopreventive agent . Anticancer Agents Med Chem , 6 : 571 – 577 .
  • Curini , M , Epifano , F , Maltese , F , Marcotullio , M C Tubaro , A . 2004 . Synthesis and anti-inflammatory activity of natural and semisynthetic geranyloxycoumarins . Bioorg Med Chem Lett , 14 : 2241 – 2243 .
  • Kohno , H , Suzuki , R , Curini , M , Epifano , F Maltese , F . 2006 . Dietary administration with prenyloxycoumarins, auraptene and collinin, inhibits colitis-related colon carcinogenesis in mice . Int J Cancer , 118 : 29336 – 2942 .
  • Tanaka , T , Kawabata , K , Kakumoto , M , Hara , A Murakami , A . 1998 . Citrus auraptene exerts dose-dependent chemopreventive activity in rat large bowel tumorigenesis: the inhibition correlates with suppression of cell proliferation and lipid peroxidation and with induction of phase II drug-metabolizing enzymes . Cancer Res , 58 : 2550 – 2556 .
  • Tanaka , T , Kohno , H , Nomura , E , Taniguchi , H Tsuno , T . 2003 . A novel geranylated derivative, ethyl 3-(4′-geranyloxy-3′-methoxyphenyl)-2-propenoate, synthesized from ferulic acid suppresses carcinogenesis and inducible nitric oxide synthase in rat tongue . Oncology , 64 : 166 – 175 .
  • Han , B S , Park , C B , Takasuka , N , Naito , A Sekine , K . 2001 . A ferulic acid derivative, ethyl 3-(4′-geranyloxy-3-methoxyphenyl)-2-propenoate, as a new candidate chemopreventive agent for colon carcinogenesis in the rat . Jpn J Cancer Res , 92 : 404 – 409 .
  • Ohshima , H , Tazawa , H , Sylla , B S and Sawa , T . 2005 . Prevention of human cancer by modulation of chronic inflammatory processes . Mutat Res , 591 : 110 – 122 .
  • Philip , M , Rowley , D A and Schreiber , H . 2004 . Inflammation as a tumor promoter in cancer induction . Semin Cancer Biol , 14 : 433 – 439 .
  • Surh , Y J , Kundu , J K , Na , H K and Lee , J . 2005 . Redox-sensitive transcription factors as prime targets for chemoprevention with anti-inflammatory and antioxidative phytochemicals . J Nutr , 135 ( 12 Suppl ) : 2993S – 3001S .
  • Murakami , A , Nakamura , Y , Ohto , Y , Yano , M Koshiba , T . 2000 . Suppressive effects of citrus fruits on free radical generation and nobiletin, an anti-inflammatory polymethoxyflavonoid . Biofactors , 12 : 187 – 192 .
  • Murakami , A , Nakamura , Y , Tanaka , T , Kawabata , K Takahashi , D . 2000 . Suppression by citrus auraptene of phorbol ester-and endotoxin-induced inflammatory responses: role of attenuation of leukocyte activation . Carcinogenesis , 21 : 1843 – 1850 .
  • Chen , I S , Lin , Y C , Tsai , I L , Teng , C M Ko , F N . 1995 . Coumarins and anti-platelet aggregation constituents from Zanthoxylum schinifolium . Phytochemistry , 39 : 1091 – 1097 .
  • Murakami , A , Kadota , M , Takahashi , D , Taniguchi , H Nomura , E . 2000 . Suppressive effects of novel ferulic acid derivatives on cellular responses induced by phorbol ester, and by combined lipopolysaccharide and interferon-gamma . Cancer Lett , 157 : 77 – 85 .
  • Hosoda , A , Nomura , E , Murakami , A , Koshimizu , K Ohigashi , H . 2002 . Synthesis of feruloyl-myo-insitol derivatives and their inhibitory effects on phorbol ester-induced superoxide generation and Esptein-Barr virus activation . Bioorg Med Chem , 10 : 1855 – 1863 .
  • Curini , M , Epifano , F and Genovese , S . 2005 . Synthesis of a novel prodrug of 3-(4′-geranyloxy-3′-methoxyphenyl)-2-trans-propenoic acid for colon delivery . Bioorg Med Chem Lett , 15 : 5049 – 5052 .
  • Suzuki , R , Kohno , H , Sugie , S , Nakagama , H and Tanaka , T . 2006 . Strain differences in the susceptibility to azoxymethane and dextran sodium sulfate-induced colon carcinogenesis in mice . Carcinogenesis , 27 : 162 – 169 .
  • Suzuki , R , Kohno , H , Sugie , S and Tanaka , T . 2004 . Sequential observations on the occurrence of preneoplastic and neoplastic lesions in mouse colon treated with azoxymethane and dextran sodium sulfate . Cancer Sci , 95 : 721 – 727 .
  • Suzuki , R , Miyamoto , S , Yasui , Y , Sugie , S and Tanaka , T . 2007 . Global gene expression analysis of the mouse colonic mucosa treated with azoxymethane and detran sodium sulfate . BMC Cancer , 7 : 84
  • Kohno , H , Suzuki , R , Yasui , Y , Miyamoto , S Wakabayashi , K . 2007 . Ursodeoxycholic acid versus sulfasalazine in colitis-related colon carcinogenesis in mice . Clin Cancer Res , 13 : 2519 – 2525 .
  • Tanaka , T , Suzuki , R , Kohno , H , Sugie , S Takahashi , M . 2005 . Colonic adenocarcinomas rapidly induced by the combined treatment with 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine and dextran sodium sulfate in male ICR mice possess beta-catenin gene mutations and increases immunoreactivity for beta-catenin, cyclooxygenase-2 and inducible nitric oxide synthase . Carcinogenesis , 26 : 229 – 238 .
  • Tanaka , T , Kohno , H , Suzuki , R , Hata , K Sugie , S . 2006 . Dextran sodium sulfate strongly promotes colorectal carcinogenesis in Apc(Min/+) mice: inflammatory stimuli by dextran sodium sulfate results in development of multiple colonic neoplasms . Int J Cancer , 118 : 25 – 34 .
  • D'Inca , R , Cardin , R , Benazzato , L , Angriman , I Martines , D . 2004 . Oxidative DNA damage in the mucosa of ulcerative colitis increases with disease duration and dysplasia . Inflamm Bowel Dis , 10 : 23 – 27 .
  • Kasai , H , Crain , P F , Kuchino , Y , Nishimura , S Ootsuyama , A . 1986 . Formation of 8-hydroxyguanine moiety in cellular DNA by agents producing oxygen radicals and evidence for its repair . Carcinogenesis , 7 : 849 – 851 .
  • Tanaka , T , Kohno , H , Suzuki , R , Yamada , Y Sugie , S . 2003 . A novel inflammation-related mouse colon carcinogenesis model induced by azoxymethane and dextran sodium sulfate . Cancer Sci , 94 : 965 – 973 .
  • Prawan , A , Kundu , J K and Surh , Y J . 2005 . Molecular basis of heme oxygenase-1 induction: implications for chemoprevention and chemoprotection . Antioxid Redox Signal , 7 : 1688 – 1703 .
  • Rao , C V , Wang , C Q , Simi , B , Rodriguez , J G Cooma , I . 2001 . Chemoprevention of colon cancer by a glutathione conjugate of 1,4-phenylenebis(methylene)selenocyanate, a novel organoselenium compound with low toxicity . Cancer Res , 61 : 3647 – 3652 .
  • Ward , J M . 1974 . Morphogenesis of chemically induced neoplasms of the colon and small intestine in rats . Lab Invest , 30 : 505 – 513 .
  • Yasui , Y , Suzuki , R , Miyamoto , S , Tsukamoto , T Sugie , S . 2007 . A lipophilic statin, pitavastatin, suppresses inflammation-associated mouse colon carcinogenesis . Int J Cancer , 121 : 2331 – 2339 .
  • Wyllie , A H , Kerr , J F and Currie , A R . 1980 . Cell death: the significance of apoptosis . Int Rev Cytol , 68 : 251 – 306 .
  • Suzuki , R , Kohno , H , Sugie , S and Tanaka , T . 2005 . Dose-dependent promoting effect of dextran sodium sulfate on mouse colon carcinogenesis initiated with azoxymethane . Histol Histopathol , 20 : 483 – 492 .
  • Ogiwara , T , Satoh , K , Kadoma , Y , Murakami , Y Unten , S . 2002 . Radical scavenging activity and cytotoxicity of ferulic acid . Anticancer Res , 22 : 2711 – 2717 .
  • Floyd , R A . 1990 . The role of 8-hydroxyguanosine in carcinogenesis . Carcinogenesis , 11 : 1447 – 1450 .
  • Harris , G K , Gupta , A , Nines , R G , Kresty , L A Habib , S G . 2001 . Effects of lyophilized black raspberries on azoxymethane-induced colon cancer and 8-hydroxy-2′-deoxyguanosine levels in the Fischer 344 rat . Nutr Cancer , 40 : 125 – 133 .
  • Weiss , J M , Goode , E L , Ladiges , W C and Ulrich , C M . 2005 . Polymorphic variation in hOGG1 and risk of cancer: a review of the functional and epidemiologic literature . Mol Carcinogenesis , 42 : 127 – 141 .
  • Shibutani , S , Takeshita , M and Grollman , A P . 1991 . Insertion of specific bases during DNA synthesis past the oxidation-damaged base 8-oxodG . Nature , 349 : 431 – 434 .
  • Tanaka , T , Miyamoto , S , Suzuki , R and Yasui , Y . 2006 . Chemoprevention of colon carcinogenesis by dietary non-nutritive compounds . Curr Top Neutraceutical Res , 4 : 127 – 152 .
  • Matsumoto , H , Yamane , T , Inagake , M , Nakatani , H Iwati , Y . 1996 . Inhibition of mucosal lipid hyperoxidation by green tea extract in 1,2-dimethylhydrazine-induced rat colonic carcinogenesis . Cancer Lett , 104 : 205 – 209 .
  • Luo , H , Tang , L , Tang , M , Billam , M Huang , T . 2006 . Phase IIa chemoprevention trial of green tea polyphenols in high-risk individuals of liver cancer: modulation of urinary excretion of green tea polyphenols and 8-hydroxydeoxyguanosine . Carcinogenesis , 27 : 262 – 268 .
  • Aggarwal , B B , Shishodia , S , Sandur , S K , Pandey , M K and Sethi , G . 2006 . Inflammation and cancer: how hot is the link? . Biochem Pharmacol , 72 : 1605 – 1621 .
  • Kohno , H , Suzuki , R , Sugie , S and Tanaka , T . 2005 . Suppression of colitis-related mouse colon carcinogenesis by a COX-2 inhibitor and PPAR ligands . BMC Cancer , 5 : 46
  • Aggarwal , B B and Shishodia , S . 2006 . Molecular targets of dietary agents for prevention and therapy of cancer . Biochem Pharmacol , 71 : 1397 – 1421 .
  • Maines , M D and Gibbs , P E . 2005 . 30 some years of heme oxygenase: from a “molecular wrecking ball” to a “mesmerizing” trigger of cellular events . Biochem Biophys Res Commun , 338 : 568 – 577 .
  • Willis , D , Moore , A R , Frederick , R and Willoughby , D A . 1996 . Heme oxygenase: a novel target for the modulation of the inflammatory response . Nat Med , 2 : 87 – 90 .
  • Otterbein , L E , Otterbein , S L , Ifedigbo , E , Liu , F Morse , D E . 2003 . MKK3 mitogen-activated protein kinase pathway mediates carbon monoxide-induced protection against oxidant-induced lung injury . Am J Pathol , 163 : 2555 – 2563 .
  • Ogborne , R M , Rushworth , S A , Charalambos , C A and O'Connell , M A . 2004 . Haem oxygenase-1: a target for dietary antioxidants . Biochem Soc Trans , 32 : 1003 – 1005 .
  • Kweon , M H , Adhami , V M , Lee , J S and Mukhtar , H . 2006 . Constitutive overexpression of Nrf2-dependent heme oxygenase-1 in A549 cells contributes to resistance to apoptosis induced by epigallocatechin 3-gallate . J Biol Chem , 281 : 33761 – 33772 .
  • Cornblatt , B S , Ye , L , Dinkova-Kostova , A T , Erb , M Fahey , J W . 2007 . Preclinical and clinical evaluation of sulforaphane for chemoprevention in the breast . Carcinogenesis , 28 : 1485 – 1490 .
  • Yao , P , Nussler , A , Liu , L , Hao , L Song , F . 2007 . Quercetin protects human hepatocytes from ethanol-derived oxidative stress by inducing heme oxygenase-1 via the MAPK/Nrf2 pathways . J Hepatol , 47 : 253 – 261 .
  • Khor , T O , Huang , M T , Kwon , K H , Chan , J Y Reddy , B S . 2006 . Nrf2-deficient mice have an increased susceptibility to dextran sulfate sodium-induced colitis . Cancer Res , 66 : 11580 – 11584 .

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