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Volumn 59, Issue 2, 2007, Pages 258-268

Quercetin selectively inhibits bioreduction and enhances apoptosis in melanoma cells that overexpress tyrosinase

Author keywords

[No Author keywords available]

Indexed keywords

GLUTATHIONE TRANSFERASE; MONOPHENOL MONOOXYGENASE; NICOTINAMIDE ADENINE DINUCLEOTIDE; OXIDOREDUCTASE; QUERCETIN; REACTIVE OXYGEN METABOLITE;

EID: 36849000866     PISSN: 01635581     EISSN: None     Source Type: Journal    
DOI: 10.1080/01635580701499545     Document Type: Article
Times cited : (33)

References (32)
  • 1
    • 0028925089 scopus 로고
    • Flavonoid intake and long-term risk of coronary heart disease and cancer in the seven countries study
    • Hertog MG, Kromhout D, Aravanis C, Blackburn H, Buzina R, et al.: Flavonoid intake and long-term risk of coronary heart disease and cancer in the seven countries study. Arch Intern Med 155, 381-386, 1995.
    • (1995) Arch Intern Med , vol.155 , pp. 381-386
    • Hertog, M.G.1    Kromhout, D.2    Aravanis, C.3    Blackburn, H.4    Buzina, R.5
  • 2
    • 0030842112 scopus 로고    scopus 로고
    • Relationship between flavonoid structure and inhibition of phosphatidylinositol 3-kinase: A comparison with tyrosine kinase and protein kinase C inhibition
    • Agullo G, Gamet-Payrastre L, Manenti S, Viala C, Remesy C, et al.: 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, 1997.
    • (1997) Biochem Pharmacol , vol.53 , pp. 1649-1657
    • Agullo, G.1    Gamet-Payrastre, L.2    Manenti, S.3    Viala, C.4    Remesy, C.5
  • 3
    • 0033859612 scopus 로고    scopus 로고
    • Flavonoids as antioxidants
    • Pietta PG: Flavonoids as antioxidants. J Nat Prod 63, 1035-1042, 2000.
    • (2000) J Nat Prod , vol.63 , pp. 1035-1042
    • Pietta, P.G.1
  • 4
    • 0043063961 scopus 로고    scopus 로고
    • Antioxidative flavonoid quercetin: Implication of its intestinal absorption and metabolism
    • Murota K and Terao J: Antioxidative flavonoid quercetin: implication of its intestinal absorption and metabolism. Arch Biochem Biophys 417, 12-17, 2003.
    • (2003) Arch Biochem Biophys , vol.417 , pp. 12-17
    • Murota, K.1    Terao, J.2
  • 5
    • 0034660208 scopus 로고    scopus 로고
    • Peroxidase-catalyzed formation of quercetin quinone methide-glutathione adducts
    • Awad HM, Boersma MG, Vervoort J, and Rietjens IM: Peroxidase-catalyzed formation of quercetin quinone methide-glutathione adducts. Arch Biochem Biophys 378, 224-233, 2000.
    • (2000) Arch Biochem Biophys , vol.378 , pp. 224-233
    • Awad, H.M.1    Boersma, M.G.2    Vervoort, J.3    Rietjens, I.M.4
  • 6
    • 0345148810 scopus 로고    scopus 로고
    • Quercetin may act as a cytotoxic prooxidant after its metabolic activation to semiquinone and quinoidal product
    • Metodiewa D, Jaiswal AK, Cenas N, Dickancaite E, and Segura-Aguilar J: Quercetin may act as a cytotoxic prooxidant after its metabolic activation to semiquinone and quinoidal product. Free Radic Biol Med 26, 107-116, 1999.
    • (1999) Free Radic Biol Med , vol.26 , pp. 107-116
    • Metodiewa, D.1    Jaiswal, A.K.2    Cenas, N.3    Dickancaite, E.4    Segura-Aguilar, J.5
  • 7
    • 0033215226 scopus 로고    scopus 로고
    • Modified vaccinia virus Ankara for delivery of human tyrosinase as melanomaassociated antigen: Induction of tyrosinase- and melanoma-specific human leukocyte antigen A*0201-restricted cytotoxic T cells in vitro and in vivo
    • Drexler I, Antunes E, Schmitz M, Wolfel T, Huber C, et al.: Modified vaccinia virus Ankara for delivery of human tyrosinase as melanomaassociated 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, 1999.
    • (1999) Cancer Res , vol.59 , pp. 4955-4963
    • Drexler, I.1    Antunes, E.2    Schmitz, M.3    Wolfel, T.4    Huber, C.5
  • 8
  • 9
    • 0032937593 scopus 로고    scopus 로고
    • Dihydrodiol dehydrogenases and polycyclic aromatic hydrocarbon activation: Generation of reactive and redox active o-quinones
    • Penning TM, Burczynski ME, Hung CF, McCoull KD, Palackal NT, et al.: Dihydrodiol dehydrogenases and polycyclic aromatic hydrocarbon activation: generation of reactive and redox active o-quinones. Chem Res Toxicol 12, 1-18, 1999.
    • (1999) Chem Res Toxicol , vol.12 , pp. 1-18
    • Penning, T.M.1    Burczynski, M.E.2    Hung, C.F.3    McCoull, K.D.4    Palackal, N.T.5
  • 10
    • 0037024378 scopus 로고    scopus 로고
    • Identification of o-quinone/quinone methide metabolites of quercetin in a cellular in vitro system
    • Awad HM, Boersma MG, Boeren S, van der WH, van ZJ, et al.: Identification of o-quinone/quinone methide metabolites of quercetin in a cellular in vitro system. FEBS Lett 520, 30-34, 2002.
    • (2002) FEBS Lett , vol.520 , pp. 30-34
    • Awad, H.M.1    Boersma, M.G.2    Boeren, S.3    van der, W.H.4    van, Z.J.5
  • 11
    • 0031020020 scopus 로고    scopus 로고
    • 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
    • Riley PA, Cooksey CJ, Johnson CI, Land EJ, Latter AM, et al.: 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, 1997.
    • (1997) Eur J Cancer , vol.33 , pp. 135-143
    • Riley, P.A.1    Cooksey, C.J.2    Johnson, C.I.3    Land, E.J.4    Latter, A.M.5
  • 12
    • 27744563096 scopus 로고    scopus 로고
    • Essential requirement of reduced glutathione (GSH) for the anti-oxidant effect of the flavonoid quercetin
    • Ferraresi R, Troiano L, Roat E, Lugli E, Nemes E, et al.: Essential requirement of reduced glutathione (GSH) for the anti-oxidant effect of the flavonoid quercetin. Free Radic Res 39, 1249-1258, 2005.
    • (2005) Free Radic Res , vol.39 , pp. 1249-1258
    • Ferraresi, R.1    Troiano, L.2    Roat, E.3    Lugli, E.4    Nemes, E.5
  • 13
    • 0035798831 scopus 로고    scopus 로고
    • Induction of human NAD(P)H:quinone oxidoreductase (NQO1) gene expression by the flavonol quercetin
    • Valerio LG Jr, Kepa JK, Pickwell GV, and Quattrochi LC: Induction of human NAD(P)H:quinone oxidoreductase (NQO1) gene expression by the flavonol quercetin. Toxicol Lett 119, 49-57, 2001.
    • (2001) Toxicol Lett , vol.119 , pp. 49-57
    • Valerio Jr, L.G.1    Kepa, J.K.2    Pickwell, G.V.3    Quattrochi, L.C.4
  • 14
    • 27744529413 scopus 로고    scopus 로고
    • The reversibility of the glutathionyl-quercetin adduct spreads oxidized quercetin-induced toxicity
    • Boots AW, Balk JM, Bast A, and Haenen GR: The reversibility of the glutathionyl-quercetin adduct spreads oxidized quercetin-induced toxicity. Biochem Biophys Res Commun 338, 923-929, 2005.
    • (2005) Biochem Biophys Res Commun , vol.338 , pp. 923-929
    • Boots, A.W.1    Balk, J.M.2    Bast, A.3    Haenen, G.R.4
  • 16
    • 0034541169 scopus 로고    scopus 로고
    • Tyrosinase mutants are capable of prodrug activation in transfected nonmelanotic cells
    • Simonova M, Wall A, Weissleder R, and Bogdanov A Jr: Tyrosinase mutants are capable of prodrug activation in transfected nonmelanotic cells. Cancer Res 60, 6656-6662, 2000.
    • (2000) Cancer Res , vol.60 , pp. 6656-6662
    • Simonova, M.1    Wall, A.2    Weissleder, R.3    Bogdanov Jr, A.4
  • 17
    • 4544295848 scopus 로고    scopus 로고
    • Oxidation products of quercetin catalyzed by mushroom tyrosinase
    • Kubo I, Nihei K, and Shimizu K: Oxidation products of quercetin catalyzed by mushroom tyrosinase. Bioorg Med Chem 12, 5343-5347, 2004.
    • (2004) Bioorg Med Chem , vol.12 , pp. 5343-5347
    • Kubo, I.1    Nihei, K.2    Shimizu, K.3
  • 19
    • 0034658104 scopus 로고    scopus 로고
    • A method for measuring disulfide reduction by cultured mammalian cells: Relative contributions of glutathione-dependent and glutathione-independent mechanisms
    • Biaglow JE, Donahue J, Tuttle S, Held K, Chrestensen C, et al.: A method for measuring disulfide reduction by cultured mammalian cells: relative contributions of glutathione-dependent and glutathione-independent mechanisms. Anal Biochem 281, 77-86, 2000.
    • (2000) Anal Biochem , vol.281 , pp. 77-86
    • Biaglow, J.E.1    Donahue, J.2    Tuttle, S.3    Held, K.4    Chrestensen, C.5
  • 20
    • 0024956031 scopus 로고
    • Molecular analysis of the DNA segments cross-hybridizable to the tyrosinase gene in patients affected with oculocutaneous albinism
    • Takeda A, Matsunaga J, Tomita Y, Tagami H, and Shibahara S: 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, 1989.
    • (1989) Tohoku J Exp Med , vol.159 , pp. 333-340
    • Takeda, A.1    Matsunaga, J.2    Tomita, Y.3    Tagami, H.4    Shibahara, S.5
  • 22
    • 0031056695 scopus 로고    scopus 로고
    • Role of copper and ceruloplasmin in oxidative mutagenesis induced by the glutathione-gamma-glutamyl transpeptidase system and by other thiols
    • Stark AA and Glass GA: 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, 1997.
    • (1997) Environ Mol Mutagen , vol.29 , pp. 63-72
    • Stark, A.A.1    Glass, G.A.2
  • 23
    • 0043166966 scopus 로고    scopus 로고
    • Oxidized quercetin reacts with thiols rather than with ascorbate: Implication for quercetin supplementation
    • Boots AW, Kubben N, Haenen GR, and Bast A: Oxidized quercetin reacts with thiols rather than with ascorbate: implication for quercetin supplementation. Biochem Biophys Res Commun 308, 560-565, 2003.
    • (2003) Biochem Biophys Res Commun , vol.308 , pp. 560-565
    • Boots, A.W.1    Kubben, N.2    Haenen, G.R.3    Bast, A.4
  • 24
    • 0036703753 scopus 로고    scopus 로고
    • A Bax-induced pro-oxidant state is critical for cytochrome c release during programmed neuronal death
    • Kirkland RA, Windelborn JA, Kasprzak JM, and Franklin JL: A Bax-induced pro-oxidant state is critical for cytochrome c release during programmed neuronal death. J Neurosci 22, 6480-6490, 2002.
    • (2002) J Neurosci , vol.22 , pp. 6480-6490
    • Kirkland, R.A.1    Windelborn, J.A.2    Kasprzak, J.M.3    Franklin, J.L.4
  • 25
    • 0034073601 scopus 로고    scopus 로고
    • Regioselectivity and reversibility of the glutathione conjugation of quercetin quinone methide
    • Boersma MG, Vervoort J, Szymusiak H, Lemanska K, Tyrakowska B, et al.: Regioselectivity and reversibility of the glutathione conjugation of quercetin quinone methide. Chem Res Toxicol 13, 185-191, 2000.
    • (2000) Chem Res Toxicol , vol.13 , pp. 185-191
    • Boersma, M.G.1    Vervoort, J.2    Szymusiak, H.3    Lemanska, K.4    Tyrakowska, B.5
  • 26
    • 33645417532 scopus 로고    scopus 로고
    • Consequences of quercetin methylation for its covalent glutathione and DNA adduct formation
    • Van der WH, Boersma MG, Alink GM, Vervoot J, and Rietjens IM: Consequences of quercetin methylation for its covalent glutathione and DNA adduct formation. Chem Biol Interact 160, 193-203, 2006.
    • (2006) Chem Biol Interact , vol.160 , pp. 193-203
    • Van der, W.H.1    Boersma, M.G.2    Alink, G.M.3    Vervoot, J.4    Rietjens, I.M.5
  • 27
    • 0032528859 scopus 로고    scopus 로고
    • Thioltransferase activity of bovine lens glutathione S-transferase
    • Dal Monte M, Cerconi I, Buono F, Vilardo PG, Del Corsd A, et al.: Thioltransferase activity of bovine lens glutathione S-transferase. Biochem J 334, 57-62, 1998.
    • (1998) Biochem J , vol.334 , pp. 57-62
    • Dal Monte, M.1    Cerconi, I.2    Buono, F.3    Vilardo, P.G.4    Del Corsd, A.5
  • 28
    • 0036181347 scopus 로고    scopus 로고
    • Glutathione and mercapturic acid conjugates of sulofenur and their activity against a human colon cancer cell line
    • Guan X, Hoffman BN, McFarland DC, Gilkerson KK, Dwivedi C, et al.: Glutathione and mercapturic acid conjugates of sulofenur and their activity against a human colon cancer cell line. Drug Metab Dispos 30, 331-335, 2002.
    • (2002) Drug Metab Dispos , vol.30 , pp. 331-335
    • Guan, X.1    Hoffman, B.N.2    McFarland, D.C.3    Gilkerson, K.K.4    Dwivedi, C.5
  • 29
    • 0035328830 scopus 로고    scopus 로고
    • Chemoprevention of colon cancer by a glutathione conjugate of 1,4-phenylenebis(methylene) selenocyanate, a novel organoselenium compound with low toxicity
    • Rao CV, Wang CQ, Simi B, Rodriguez JG, Cooma I, et al.: 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, 2001.
    • (2001) Cancer Res , vol.61 , pp. 3647-3652
    • Rao, C.V.1    Wang, C.Q.2    Simi, B.3    Rodriguez, J.G.4    Cooma, I.5
  • 30
    • 34249322665 scopus 로고    scopus 로고
    • Regression of lung and colon cancer xenografts by depleting or inhibiting RLIP76 (Ral-Binding protein 1)
    • Singhal SS, Singhal J, Yadav S, Dwivedi S, Boor PJ, et al.: Regression of lung and colon cancer xenografts by depleting or inhibiting RLIP76 (Ral-Binding protein 1). Cancer Res 67, 4382-4389, 2007.
    • (2007) Cancer Res , vol.67 , pp. 4382-4389
    • Singhal, S.S.1    Singhal, J.2    Yadav, S.3    Dwivedi, S.4    Boor, P.J.5
  • 31
    • 0026495979 scopus 로고
    • Effects of phenol compounds, glutathione analogues and a diuretic drug on glutathione S-transferase, glutathione reductase and glutathione peroxidase from canine erythrocytes
    • Kurata M, Suzuki M, and Takeda K: 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, 1992.
    • (1992) Comp Biochem Physiol B , vol.103 , pp. 863-867
    • Kurata, M.1    Suzuki, M.2    Takeda, K.3
  • 32
    • 0018079525 scopus 로고
    • Mutagenicity of plant flavonoids: Structural requirements for mutagenic activity in Salmonella typhimurium
    • MacGregor JT and Jurd L: Mutagenicity of plant flavonoids: structural requirements for mutagenic activity in Salmonella typhimurium. Mutat Res 54, 297-309, 1978.
    • (1978) Mutat Res , vol.54 , pp. 297-309
    • MacGregor, J.T.1    Jurd, L.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.