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Volumn 200, Issue 1, 2012, Pages 28-37

Phenylalkyl isoselenocyanates vs phenylalkyl isothiocyanates: Thiol reactivity and its implications

Author keywords

Chemiluminesence; Isoselenocyanates; Isothiocyanates; Redox cycling; ROS; Thiol reactivity

Indexed keywords

ANTINEOPLASTIC AGENT; GLUTATHIONE; ISOTHIOCYANIC ACID DERIVATIVE; PHENYLALKYL ISOSELENOCYANATE DERIVATVE; PHENYLALKYL ISOTHIOCYANATE DERIVATVE; REACTIVE OXYGEN METABOLITE; SUPEROXIDE; THIOL; UNCLASSIFIED DRUG;

EID: 84867218755     PISSN: 00092797     EISSN: 18727786     Source Type: Journal    
DOI: 10.1016/j.cbi.2012.08.022     Document Type: Article
Times cited : (30)

References (36)
  • 2
    • 0025959673 scopus 로고
    • A/J mouse lung tumorigenesis by the tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and its inhibition by arylalkyl isothiocyanates
    • S.S. Hecht, M.A. Morse, K.I. Eklind, and F.L. Chung A/J mouse lung tumorigenesis by the tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3- pyridyl)-1-butanone and its inhibition by arylalkyl isothiocyanates Exp. Lung Res. 17 1991 501 511
    • (1991) Exp. Lung Res. , vol.17 , pp. 501-511
    • Hecht, S.S.1    Morse, M.A.2    Eklind, K.I.3    Chung, F.L.4
  • 3
    • 0025133114 scopus 로고
    • Metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in mouse lung microsomes and its inhibition by isothiocyanates
    • T.J. Smith, Z.Y. Guo, P.E. Thomas, F.L. Chung, M.A. Morse, K. Elkind, and C.S. Yang Metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in mouse lung microsomes and its inhibition by isothiocyanates Cancer Res. 50 1990 6817 6822 (Pubitemid 20361073)
    • (1990) Cancer Research , vol.50 , Issue.21 , pp. 6817-6822
    • Smith, T.J.1    Guo, Z.2    Thomas, P.E.3    Chung, F.-L.4    Morse, M.A.5    Elkind, K.6    Yang, C.S.7
  • 4
    • 0035170990 scopus 로고    scopus 로고
    • Phytochemicals from cruciferous plants protect against cancer by modulating carcinogen metabolism
    • P. Talalay, and J.W. Fahey Phytochemicals from cruciferous plants protect against cancer by modulating carcinogen metabolism J. Nutr. 131 2001 3027S 3033S (Pubitemid 33070774)
    • (2001) Journal of Nutrition , vol.131 , Issue.11 SUPPL.
    • Talalay, P.1    Fahey, J.W.2
  • 5
    • 0025809376 scopus 로고
    • Structure-activity relationships for inhibition of 4-(methylnitrosamino)- 1-(3-pyridyl)-1-butanone lung tumorigenesis by arylalkyl isothiocyanates in A/J mice
    • M.A. Morse, K.I. Eklind, S.S. Hecht, K.G. Jordan, C.I. Choi, D.H. Desai, S.G. Amin, and F.L. Chung Structure-activity relationships for inhibition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone lung tumorigenesis by arylalkyl isothiocyanates in A/J mice Cancer Res. 51 1991 1846 1850
    • (1991) Cancer Res. , vol.51 , pp. 1846-1850
    • Morse, M.A.1    Eklind, K.I.2    Hecht, S.S.3    Jordan, K.G.4    Choi, C.I.5    Desai, D.H.6    Amin, S.G.7    Chung, F.L.8
  • 6
    • 0027273265 scopus 로고
    • Structure-activity relationships of arylalkyl isothiocyanates for the inhibition of 4-(methylnitrosammo)-1-(3-pyridyl)-1-butanone metabolism and the modulation of xenobiotic-metabolizing enzymes in rats and mice
    • Z. Guo, T. Smith, E. Wang, K.I. Eklind, F.L. Chung, and C.S. Yang Structure-activity relationships of arylalkyl isothiocyanates for the inhibition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone metabolism and the modulation of xenobiotic-metabolizing enzymes in rats and mice Carcinogenesis 14 1993 1167 1173 (Pubitemid 23193547)
    • (1993) Carcinogenesis , vol.14 , Issue.6 , pp. 1167-1173
    • Guo, Z.1    Smith, T.J.2    Wang, E.3    Ekling, K.I.4    Chung, F.-L.5    Yang, C.S.6
  • 7
    • 0030994774 scopus 로고    scopus 로고
    • Isothiocyanates and plant polyphenols as inhibitors of lung and esophageal cancer
    • DOI 10.1016/S0304-3835(97)04639-9, PII S0304383597046399
    • G.D. Stoner, and M.A. Morse Isothiocyanates and plant polyphenols as inhibitors of lung and esophageal cancer Cancer Lett. 114 1997 113 119 (Pubitemid 27140089)
    • (1997) Cancer Letters , vol.114 , Issue.1-2 , pp. 113-119
    • Stoner, G.D.1    Morse, M.A.2
  • 8
    • 0028016171 scopus 로고
    • Structure-activity relationships of isothiocyanates as mechanism-based inhibitors of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone-induced lung tumorigenesis in A/J mice
    • D. Jiao, K.I. Eklind, C.I. Choi, D.H. Desai, S.G. Amin, and F.L. Chung Structure-activity relationships of isothiocyanates as mechanism-based inhibitors of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone-induced lung tumorigenesis in A/J mice Cancer Res. 54 1994 4327 4333 (Pubitemid 24273143)
    • (1994) Cancer Research , vol.54 , Issue.16 , pp. 4327-4333
    • Jiao, D.1    Eklind, K.I.2    Choi, C.-I.3    Desai, D.H.4    Amin, S.G.5    Chung, F.-L.6
  • 9
    • 0035094701 scopus 로고    scopus 로고
    • Molecular mechanism of rapid cellular accumulation of anticarcinogenic isothiocyanates
    • Y. Zhang Molecular mechanism of rapid cellular accumulation of anticarcinogenic isothiocyanates Carcinogenesis 22 2001 425 431 (Pubitemid 32203821)
    • (2001) Carcinogenesis , vol.22 , Issue.3 , pp. 425-431
    • Zhang, Y.1
  • 10
    • 0028919911 scopus 로고
    • Forward and reverse catalysis and product sequestration by human glutathione S-transferases in the reaction of GSH with dietary aralkyl isothiocyanates
    • D.J. Meyer, D.J. Crease, and B. Ketterer Forward and reverse catalysis and product sequestration by human glutathione S-transferases in the reaction of GSH with dietary aralkyl isothiocyanates Biochem. J. 306 Pt 2 1995 565 569
    • (1995) Biochem. J. , vol.306 , Issue.PART 2 , pp. 565-569
    • Meyer, D.J.1    Crease, D.J.2    Ketterer, B.3
  • 11
    • 0032406798 scopus 로고    scopus 로고
    • Human metabolism and excretion of cancer chemoprotective glucosinolates and isothiocyanates of cruciferous vegetables
    • T.A. Shapiro, J.W. Fahey, K.L. Wade, K.K. Stephenson, and P. Talalay Human metabolism and excretion of cancer chemoprotective glucosinolates and isothiocyanates of cruciferous vegetables Cancer Epidemiol. Biomarkers Prev. 7 1998 1091 1100 (Pubitemid 29001665)
    • (1998) Cancer Epidemiology Biomarkers and Prevention , vol.7 , Issue.12 , pp. 1091-1100
    • Shapiro, T.A.1    Fahey, J.W.2    Wade, K.L.3    Stephenson, K.K.4    Talalay, P.5
  • 12
    • 0035987188 scopus 로고    scopus 로고
    • Isothiocyanates as cancer chemopreventive agents: Their biological activities and metabolism in rodents and humans
    • DOI 10.2174/1389200023337496
    • C.C. Conaway, Y.M. Yang, and F.L. Chung Isothiocyanates as cancer chemopreventive agents: their biological activities and metabolism in rodents and humans Curr. Drug Metab. 3 2002 233 255 (Pubitemid 34625038)
    • (2002) Current Drug Metabolism , vol.3 , Issue.3 , pp. 233-255
    • Conaway, C.C.1    Yang, Y.-M.2    Chung, F.-L.3
  • 13
    • 0032980125 scopus 로고    scopus 로고
    • Chemoprevention of cancer by isothiocyanates, modifiers of carcinogen metabolism
    • S.S. Hecht Chemoprevention of cancer by isothiocyanates, modifiers of carcinogen metabolism J. Nutr. 129 1999 768S 774S
    • (1999) J. Nutr. , vol.129
    • Hecht, S.S.1
  • 16
    • 58449110311 scopus 로고    scopus 로고
    • Phenethyl isothiocyanate induced apoptosis via down regulation of Bcl-2/XIAP and triggering of the mitochondrial pathway in MCF-7 cells
    • J.W. Lee, and M.K. Cho Phenethyl isothiocyanate induced apoptosis via down regulation of Bcl-2/XIAP and triggering of the mitochondrial pathway in MCF-7 cells Arch. Pharm. Res. 31 2008 1604 1612
    • (2008) Arch. Pharm. Res. , vol.31 , pp. 1604-1612
    • Lee, J.W.1    Cho, M.K.2
  • 17
    • 77951496270 scopus 로고    scopus 로고
    • Effects of phenylethyl isothiocyanate and its metabolite on cell-cycle arrest and apoptosis in LNCaP human prostate cancer cells
    • E.S. Hwang, and H.J. Lee Effects of phenylethyl isothiocyanate and its metabolite on cell-cycle arrest and apoptosis in LNCaP human prostate cancer cells Int. J. Food Sci. Nutr. 61 2010 324 336
    • (2010) Int. J. Food Sci. Nutr. , vol.61 , pp. 324-336
    • Hwang, E.S.1    Lee, H.J.2
  • 18
    • 55949126657 scopus 로고    scopus 로고
    • Binding to protein by isothiocyanates: A potential mechanism for apoptosis induction in human non small lung cancer cells
    • L. Mi, and F.L. Chung Binding to protein by isothiocyanates: a potential mechanism for apoptosis induction in human non small lung cancer cells Nutr. Cancer 60 Suppl 1 2008 12 20
    • (2008) Nutr. Cancer , vol.60 , Issue.SUPPL. 1 , pp. 12-20
    • Mi, L.1    Chung, F.L.2
  • 20
    • 33748146888 scopus 로고    scopus 로고
    • Selective killing of oncogenically transformed cells through a ROS-mediated mechanism by β-phenylethyl isothiocyanate
    • DOI 10.1016/j.ccr.2006.08.009, PII S1535610806002509
    • D. Trachootham, Y. Zhou, H. Zhang, Y. Demizu, Z. Chen, H. Pelicano, P.J. Chiao, G. Achanta, R.B. Arlinghaus, J. Liu, and P. Huang Selective killing of oncogenically transformed cells through a ROS-mediated mechanism by beta-phenylethyl isothiocyanate Cancer Cell 10 2006 241 252 (Pubitemid 44311067)
    • (2006) Cancer Cell , vol.10 , Issue.3 , pp. 241-252
    • Trachootham, D.1    Zhou, Y.2    Zhang, H.3    Demizu, Y.4    Chen, Z.5    Pelicano, H.6    Chiao, P.J.7    Achanta, G.8    Arlinghaus, R.B.9    Liu, J.10    Huang, P.11
  • 21
    • 58149090697 scopus 로고    scopus 로고
    • Synthesis and anticancer activity comparison of phenylalkyl isoselenocyanates with corresponding naturally occurring and synthetic isothiocyanates
    • A.K. Sharma, A. Sharma, D. Desai, S.V. Madhunapantula, S.J. Huh, G.P. Robertson, and S. Amin Synthesis and anticancer activity comparison of phenylalkyl isoselenocyanates with corresponding naturally occurring and synthetic isothiocyanates J. Med. Chem. 51 2008 7820 7826
    • (2008) J. Med. Chem. , vol.51 , pp. 7820-7826
    • Sharma, A.K.1    Sharma, A.2    Desai, D.3    Madhunapantula, S.V.4    Huh, S.J.5    Robertson, G.P.6    Amin, S.7
  • 22
    • 28544440524 scopus 로고    scopus 로고
    • Selenoprotein deficiency and high levels of selenium compounds can effectively inhibit hepatocarcinogenesis in transgenic mice
    • DOI 10.1038/sj.onc.1208940
    • S.V. Novoselov, D.F. Calvisi, V.M. Labunskyy, V.M. Factor, B.A. Carlson, D.E. Fomenko, M.E. Moustafa, D.L. Hatfield, and V.N. Gladyshev Selenoprotein deficiency and high levels of selenium compounds can effectively inhibit hepatocarcinogenesis in transgenic mice Oncogene 24 2005 8003 8011 (Pubitemid 41746744)
    • (2005) Oncogene , vol.24 , Issue.54 , pp. 8003-8011
    • Novoselov, S.V.1    Calvisi, D.F.2    Labunskyy, V.M.3    Factor, V.M.4    Carlson, B.A.5    Fomenko, D.E.6    Moustafa, M.E.7    Hatfield, D.L.8    Gladyshev, V.N.9
  • 23
    • 0034982964 scopus 로고    scopus 로고
    • Selenium, selenoproteins and human health: A review
    • K.M. Brown, and J.R. Arthur Selenium, selenoproteins and human health: a review Public Health Nutr. 4 2001 593 599 (Pubitemid 32524579)
    • (2001) Public Health Nutrition , vol.4 , Issue.2 B , pp. 593-599
    • Brown, K.M.1    Arthur, J.R.2
  • 24
    • 28244462778 scopus 로고    scopus 로고
    • Selenium in cancer prevention: A review of the evidence and mechanism of action
    • DOI 10.1079/PNS2005467
    • M.P. Rayman Selenium in cancer prevention: a review of the evidence and mechanism of action Proc. Nutr. Soc. 64 2005 527 542 (Pubitemid 41705454)
    • (2005) Proceedings of the Nutrition Society , vol.64 , Issue.4 , pp. 527-542
    • Rayman, M.P.1
  • 25
    • 45549101964 scopus 로고    scopus 로고
    • Selenium compounds and selenoproteins in cancer
    • R. Brigelius-Flohe Selenium compounds and selenoproteins in cancer Chem. Biodivers 5 2008 389 395
    • (2008) Chem. Biodivers , vol.5 , pp. 389-395
    • Brigelius-Flohe, R.1
  • 26
    • 36749004377 scopus 로고    scopus 로고
    • Selenium as an anticancer nutrient: Roles in cell proliferation and tumor cell invasion
    • DOI 10.1016/j.jnutbio.2007.02.005, PII S0955286307000757
    • H. Zeng, and G.F. Combs Selenium as an anticancer nutrient: roles in cell proliferation and tumor cell invasion J. Nutr. Biochem. 19 2008 1 7 (Pubitemid 350213396)
    • (2008) Journal of Nutritional Biochemistry , vol.19 , Issue.1 , pp. 1-7
    • Zeng, H.1    Combs Jr., G.F.2
  • 28
    • 79960335679 scopus 로고    scopus 로고
    • The Akt inhibitor ISC-4 activates prostate apoptosis response protein-4 and reduces colon tumor growth in a nude mouse model
    • A.K. Sharma, C.L. Kline, A. Berg, S. Amin, and R.B. Irby The Akt inhibitor ISC-4 activates prostate apoptosis response protein-4 and reduces colon tumor growth in a nude mouse model Clin. Cancer Res. 17 2011 4474 4483
    • (2011) Clin. Cancer Res. , vol.17 , pp. 4474-4483
    • Sharma, A.K.1    Kline, C.L.2    Berg, A.3    Amin, S.4    Irby, R.B.5
  • 30
    • 81555222611 scopus 로고    scopus 로고
    • Phenylbutyl Isoselenocyanate modulates phase i and II enzymes and inhibits 4-(methylnitrosamino) -1-(3-pyridyl)-1-butanone induced DNA adducts in Mice
    • M.A. Crampsie, N. Jones, A. Das, C. Aliaga, D. Desai, P. Lazarus, S. Amin, and A.K. Sharma Phenylbutyl Isoselenocyanate modulates phase I and II enzymes and inhibits 4-(methylnitrosamino) -1-(3-pyridyl)-1-butanone induced DNA adducts in Mice Cancer Prev. Res. (Phila) 4 2011 1884 1894
    • (2011) Cancer Prev. Res. (Phila) , vol.4 , pp. 1884-1894
    • Crampsie, M.A.1    Jones, N.2    Das, A.3    Aliaga, C.4    Desai, D.5    Lazarus, P.6    Amin, S.7    Sharma, A.K.8
  • 31
    • 34447299398 scopus 로고    scopus 로고
    • Role of pro-oxidants and antioxidants in the anti-inflammatory and apoptotic effects of curcumin (diferuloylmethane)
    • DOI 10.1016/j.freeradbiomed.2007.05.009, PII S0891584907003255
    • S.K. Sandur, H. Ichikawa, M.K. Pandey, A.B. Kunnumakkara, B. Sung, G. Sethi, and B.B. Aggarwal Role of pro-oxidants and antioxidants in the anti-inflammatory and apoptotic effects of curcumin (diferuloylmethane) Free Radic. Biol. Med. 43 2007 568 580 (Pubitemid 47058232)
    • (2007) Free Radical Biology and Medicine , vol.43 , Issue.4 , pp. 568-580
    • Sandur, S.K.1    Ichikawa, H.2    Pandey, M.K.3    Kunnumakkara, A.B.4    Sung, B.5    Sethi, G.6    Aggarwal, B.B.7
  • 32
    • 77950038193 scopus 로고    scopus 로고
    • Enhanced Nrf2-dependent induction of glutathione in mouse embryonic fibroblasts by isoselenocyanate analog of sulforaphane
    • S.W. Emmert, D. Desai, S. Amin, and J.P. Richie Jr. Enhanced Nrf2-dependent induction of glutathione in mouse embryonic fibroblasts by isoselenocyanate analog of sulforaphane Bioorg. Med. Chem. Lett. 20 2010 2675 2679
    • (2010) Bioorg. Med. Chem. Lett. , vol.20 , pp. 2675-2679
    • Emmert, S.W.1    Desai, D.2    Amin, S.3    Richie Jr., J.P.4
  • 33
    • 0026682519 scopus 로고
    • Glutathione oxidase activity of selenocystamine: A mechanistic study
    • J. Chaudiere, O. Courtin, and J. Leclaire Glutathione oxidase activity of selenocystamine: a mechanistic study Arch. Biochem. Biophys. 296 1992 328 336
    • (1992) Arch. Biochem. Biophys. , vol.296 , pp. 328-336
    • Chaudiere, J.1    Courtin, O.2    Leclaire, J.3
  • 34
    • 1242263520 scopus 로고    scopus 로고
    • Methioninase and selenomethionine but not Se-methylselenocysteine generate methylselenol and superoxide in an in vitro chemiluminescent assay: Implications for the nutritional carcinostatic activity of selenoamino acids
    • DOI 10.1016/j.bcp.2003.09.004
    • J.E. Spallholz, V.P. Palace, and T.W. Reid Methioninase and selenomethionine but not Se-methylselenocysteine generate methylselenol and superoxide in an in vitro chemiluminescent assay: implications for the nutritional carcinostatic activity of selenoamino acids Biochem. Pharmacol 67 2004 547 554 (Pubitemid 38232894)
    • (2004) Biochemical Pharmacology , vol.67 , Issue.3 , pp. 547-554
    • Spallholz, J.E.1    Palace, V.P.2    Reid, T.W.3
  • 35
    • 1542337018 scopus 로고    scopus 로고
    • Selenium Redox Cycling in the Protective Effects of Organoselenides against Oxidant-Induced DNA Damage
    • DOI 10.1021/ja037294j
    • V. De Silva, M.M. Woznichak, K.L. Burns, K.B. Grant, and S.W. May Selenium redox cycling in the protective effects of organoselenides against oxidant-induced DNA damage J. Am. Chem. Soc. 126 2004 2409 2413 (Pubitemid 38295723)
    • (2004) Journal of the American Chemical Society , vol.126 , Issue.8 , pp. 2409-2413
    • De Silva, V.1    Woznichak, M.M.2    Burns, K.L.3    Grant, K.B.4    May, S.W.5
  • 36
    • 2442526626 scopus 로고    scopus 로고
    • The chemopreventive agent phenetyl isothiocyanate sensitizes cells to Fas-mediated apoptosis
    • DOI 10.1093/carcin/bgh063
    • J.M. Pullar, S.J. Thomson, M.J. King, C.I. Turnbull, R.G. Midwinter, and M.B. Hampton The chemopreventive agent phenethyl isothiocyanate sensitizes cells to Fas-mediated apoptosis Carcinogenesis 25 2004 765 772 (Pubitemid 38618529)
    • (2004) Carcinogenesis , vol.25 , Issue.5 , pp. 765-772
    • Pullar, J.M.1    Thomson, S.J.2    King, M.J.3    Turnbull, C.I.4    Midwinter, R.G.5    Hampton, M.6


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