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Reports

Quercetin Selectively Inhibits Bioreduction and Enhances Apoptosis in Melanoma Cells That Overexpress Tyrosinase

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Pages 258-268 | Received 06 Apr 2007, Accepted 29 May 2007, Published online: 05 Dec 2007

References

  • Hertog , M G , Kromhout , D , Aravanis , C , Blackburn , H Buzina , R . 1995 . Flavonoid intake and long-term risk of coronary heart disease and cancer in the seven countries study . Arch Intern Med , 155 : 381 – 386 .
  • Agullo , G , Gamet-Payrastre , L , Manenti , S , Viala , C Remesy , C . 1997 . Relationship between flavonoid structure and inhibition of phosphatidylinositol 3-kinase: a comparison with tyrosine kinase and protein kinase C inhibition . Biochem Pharmacol , 53 : 1649 – 1657 .
  • Pietta , P G . 2000 . Flavonoids as antioxidants . J Nat Prod , 63 : 1035 – 1042 .
  • Murota , K and Terao , J . 2003 . Antioxidative flavonoid quercetin: implication of its intestinal absorption and metabolism . Arch Biochem Biophys , 417 : 12 – 17 .
  • Awad , H M , Boersma , M G , Vervoort , J and Rietjens , I M . 2000 . Peroxidase-catalyzed formation of quercetin quinone methide-glutathione adducts . Arch Biochem Biophys , 378 : 224 – 233 .
  • Metodiewa , D , Jaiswal , A K , Cenas , N , Dickancaite , E and Segura-Aguilar , J . 1999 . Quercetin may act as a cytotoxic prooxidant after its metabolic activation to semiquinone and quinoidal product . Free Radic Biol Med , 26 : 107 – 116 .
  • Drexler , I , Antunes , E , Schmitz , M , Wolfel , T Huber , C . 1999 . Modified vaccinia virus Ankara for delivery of human tyrosinase as melanoma-associated antigen: induction of tyrosinase- and melanoma-specific human leukocyte antigen A∗0201-restricted cytotoxic T cells in vitro and in vivo . Cancer Res , 59 : 4955 – 4963 .
  • Bolton , J L , Pisha , E , Zhang , F and Qiu , S . 1998 . Role of quinoids in estrogen carcinogenesis . Chem Res Toxicol , 11 : 1113 – 1127 .
  • Penning , T M , Burczynski , M E , Hung , C F , McCoull , K D Palackal , N T . 1999 . Dihydrodiol dehydrogenases and polycyclic aromatic hydrocarbon activation: generation of reactive and redox active o-quinones . Chem Res Toxicol , 12 : 1 – 18 .
  • Awad , H M , Boersma , M G , Boeren , S , van der , W H van , Z J . 2002 . Identification of o-quinone/quinone methide metabolites of quercetin in a cellular in vitro system . FEBS Lett , 520 : 30 – 34 .
  • Riley , P A , Cooksey , C J , Johnson , C I , Land , E J Latter , A M . 1997 . Melanogenesis-targeted anti-melanoma pro-drug development: effect of side-chain variations on the cytotoxicity of tyrosinase-generated ortho-quinones in a model screening system . Eur J Cancer , 33 : 135 – 143 .
  • Ferraresi , R , Troiano , L , Roat , E , Lugli , E Nemes , E . 2005 . Essential requirement of reduced glutathione (GSH) for the anti-oxidant effect of the flavonoid quercetin . Free Radic Res , 39 : 1249 – 1258 .
  • Valerio , L G Jr. , Kepa , J K , Pickwell , G V and Quattrochi , L C . 2001 . Induction of human NAD(P)H:quinone oxidoreductase (NQO1) gene expression by the flavonol quercetin . Toxicol Lett , 119 : 49 – 57 .
  • Boots , A W , Balk , J M , Bast , A and Haenen , G R . 2005 . The reversibility of the glutathionyl-quercetin adduct spreads oxidized quercetin-induced toxicity . Biochem Biophys Res Commun , 338 : 923 – 929 .
  • Asher , G , Lotem , J , Kama , R , Sachs , L and Shaul , Y . 2002 . NQO1 stabilizes p53 through a distinct pathway . Proc Natl Acad Sci U S A , 99 : 3099 – 3104 .
  • Simonova , M , Wall , A , Weissleder , R and Bogdanov , A Jr. 2000 . Tyrosinase mutants are capable of prodrug activation in transfected nonmelanotic cells . Cancer Res , 60 : 6656 – 6662 .
  • Kubo , I , Nihei , K and Shimizu , K . 2004 . Oxidation products of quercetin catalyzed by mushroom tyrosinase . Bioorg Med Chem , 12 : 5343 – 5347 .
  • van Zanden , J J , Ben , H O , van Iersel , M L , Boeren , S Cnubben , N H . 2003 . Inhibition of human glutathione S-transferase P1-1 by the flavonoid quercetin . Chem Biol Interact , 145 : 139 – 148 .
  • Biaglow , J E , Donahue , J , Tuttle , S , Held , K Chrestensen , C . 2000 . A method for measuring disulfide reduction by cultured mammalian cells: relative contributions of glutathione-dependent and glutathione-independent mechanisms . Anal Biochem , 281 : 77 – 86 .
  • Takeda , A , Matsunaga , J , Tomita , Y , Tagami , H and Shibahara , S . 1989 . Molecular analysis of the DNA segments cross-hybridizable to the tyrosinase gene in patients affected with oculocutaneous albinism . Tohoku J Exp Med , 159 : 333 – 340 .
  • Biaglow , J E , Ayene , I S , Koch , C J , Donahue , J Stamato , T D . 2003 . Radiation response of cells during altered protein thiol redox . Radiat Res , 159 : 484 – 494 .
  • Stark , A A and Glass , G A . 1997 . Role of copper and ceruloplasmin in oxidative mutagenesis induced by the glutathione-gamma-glutamyl transpeptidase system and by other thiols . Environ Mol Mutagen , 29 : 63 – 72 .
  • Boots , A W , Kubben , N , Haenen , G R and Bast , A . 2003 . Oxidized quercetin reacts with thiols rather than with ascorbate: implication for quercetin supplementation . Biochem Biophys Res Commun , 308 : 560 – 565 .
  • Kirkland , R A , Windelborn , J A , Kasprzak , J M and Franklin , J L . 2002 . A Bax-induced pro-oxidant state is critical for cytochrome c release during programmed neuronal death . J Neurosci , 22 : 6480 – 6490 .
  • Boersma , M G , Vervoort , J , Szymusiak , H , Lemanska , K Tyrakowska , B . 2000 . Regioselectivity and reversibility of the glutathione conjugation of quercetin quinone methide . Chem Res Toxicol , 13 : 185 – 191 .
  • Van der , W H , Boersma , M G , Alink , G M , Vervoot , J and Rietjens , I M . 2006 . Consequences of quercetin methylation for its covalent glutathione and DNA adduct formation . Chem Biol Interact , 160 : 193 – 203 .
  • Dal Monte , M , Cerconi , I , Buono , F , Vilardo , P G Del Corsd , A . 1998 . Thioltransferase activity of bovine lens glutathione S-transferase . Biochem J , 334 : 57 – 62 .
  • Guan , X , Hoffman , B N , McFarland , D C , Gilkerson , K K Dwivedi , C . 2002 . Glutathione and mercapturic acid conjugates of sulofenur and their activity against a human colon cancer cell line . Drug Metab Dispos , 30 : 331 – 335 .
  • 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 .
  • Singhal , S S , Singhal , J , Yadav , S , Dwivedi , S Boor , P J . 2007 . Regression of lung and colon cancer xenografts by depleting or inhibiting RLIP76 (Ral-Binding protein 1) . Cancer Res , 67 : 4382 – 4389 .
  • Kurata , M , Suzuki , M and Takeda , K . 1992 . Effects of phenol compounds, glutathione analogues and a diuretic drug on glutathione S-transferase, glutathione reductase and glutathione peroxidase from canine erythrocytes . Comp Biochem Physiol B , 103 : 863 – 867 .
  • MacGregor , J T and Jurd , L . 1978 . Mutagenicity of plant flavonoids: structural requirements for mutagenic activity in Salmonella typhimurium . Mutat Res , 54 : 297 – 309 .

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