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Volumn 50, Issue 3, 2009, Pages 164-170

Three structurally homologous isothiocyanates exert "janus" characteristics in human hepg2 cells

Author keywords

3 Methylthiopropyl isothiocyanate; 4 Methylthiobutyl sothiocyanate; 5 Methylthiopentyl isothiocyanate; Comet assay; DNA repair; HepG2 cells; Micronucleus test

Indexed keywords

3 METHYLTHIOPROPYL ISOTHIOCYANATE; 5 METHYLTHIOPENTYL ISOTHIOCYANATE; ERUCIN; ISOTHIOCYANIC ACID DERIVATIVE; UNCLASSIFIED DRUG; ANTINEOPLASTIC AGENT; MUTAGENIC AGENT;

EID: 63049132775     PISSN: 08936692     EISSN: 10982280     Source Type: Journal    
DOI: 10.1002/em.20470     Document Type: Article
Times cited : (13)

References (38)
  • 1
    • 0035987188 scopus 로고    scopus 로고
    • Isothiocyanates as cancer chemopreventive agents: Their biological activities and metabolism in rodents and humans
    • Conaway CC, Yang YM, Chung FL. 2002. Isothiocyanates as cancer chemopreventive agents: Their biological activities and metabolism in rodents and humans. Curr Drug Metab 3:233-255.
    • (2002) Curr Drug Metab , vol.3 , pp. 233-255
    • Conaway, C.C.1    Yang, Y.M.2    Chung, F.L.3
  • 2
    • 0041363371 scopus 로고    scopus 로고
    • A facile and efficient synthesis of 14C-labelled sulforaphane
    • D'Souza CA, Amin S, Dhimant D. 2003. A facile and efficient synthesis of 14C-labelled sulforaphane. J Labelled Comp Radiopharm 46:851-859.
    • (2003) J Labelled Comp Radiopharm , vol.46 , pp. 851-859
    • D'Souza, C.A.1    Amin, S.2    Dhimant, D.3
  • 4
    • 0024461337 scopus 로고
    • Identification of aneuploidy-inducing agents using cytokinesis-blocked human lymphocytes and an anti- kinetochore antibody
    • Eastmond DA, Tucker JD. 1989. Identification of aneuploidy-inducing agents using cytokinesis-blocked human lymphocytes and an anti- kinetochore antibody. Environ Mol Mutagen 13:34-43.
    • (1989) Environ Mol Mutagen , vol.13 , pp. 34-43
    • Eastmond, D.A.1    Tucker, J.D.2
  • 5
    • 0040698944 scopus 로고    scopus 로고
    • Fischer J. 1992. Sulphur- and nitrogen-containing volatile components of kohlrabi (Brassica oleracea var. gongylodes L.). Z Lebensm Uners Forsch 194:259-262.
    • Fischer J. 1992. Sulphur- and nitrogen-containing volatile components of kohlrabi (Brassica oleracea var. gongylodes L.). Z Lebensm Uners Forsch 194:259-262.
  • 6
    • 0037182151 scopus 로고    scopus 로고
    • A protocol for the in vitro micronucleus test. I. Contributions to the development of a protocol suitable for regulatory submissions from an examination of 16 chemicals with different mechanisms of action and different levels of activity
    • Garriott ML, Phelps JB, Hoffman WP. 2002. A protocol for the in vitro micronucleus test. I. Contributions to the development of a protocol suitable for regulatory submissions from an examination of 16 chemicals with different mechanisms of action and different levels of activity. Mutat Res 517:123-134.
    • (2002) Mutat Res , vol.517 , pp. 123-134
    • Garriott, M.L.1    Phelps, J.B.2    Hoffman, W.P.3
  • 7
    • 0034485496 scopus 로고    scopus 로고
    • Inactivation of cytochrome P450 2B1 by benzyl isothiocyanate, a chemopreven- tative agent from cruciferous vegetables
    • Goosen TC, Kent UM, Brand L, Hollenberg PF. 2000. Inactivation of cytochrome P450 2B1 by benzyl isothiocyanate, a chemopreven- tative agent from cruciferous vegetables. Chem Res Toxicol 13:1349-1359.
    • (2000) Chem Res Toxicol , vol.13 , pp. 1349-1359
    • Goosen, T.C.1    Kent, U.M.2    Brand, L.3    Hollenberg, P.F.4
  • 8
    • 0034538640 scopus 로고    scopus 로고
    • Inhibition of carcinogenesis by isothiocyanates
    • Hecht SS. 2000. Inhibition of carcinogenesis by isothiocyanates. Drug Metab Rev 32:395-411.
    • (2000) Drug Metab Rev , vol.32 , pp. 395-411
    • Hecht, S.S.1
  • 9
    • 0037058628 scopus 로고    scopus 로고
    • Benzyl isothiocy-anate: An effective inhibitor of polycyclic aromatic hydrocarbon tumorigenesis in A/J mouse lung
    • Hecht SS, Kenney PM, Wang M, Upadhyaya P. 2002. Benzyl isothiocy-anate: An effective inhibitor of polycyclic aromatic hydrocarbon tumorigenesis in A/J mouse lung. Cancer Lett 187:87-94.
    • (2002) Cancer Lett , vol.187 , pp. 87-94
    • Hecht, S.S.1    Kenney, P.M.2    Wang, M.3    Upadhyaya, P.4
  • 10
    • 0031827624 scopus 로고    scopus 로고
    • Strong promoting activity of phenylethyl isothio- cyanate and benzyl isothiocyanate on urinary bladder carcinogen- esis in F344 male rats
    • Hirose M, Yamaguchi T, Kimoto N, Ogawa K, Futakuchi M, Sano M, Shirai T. 1998. Strong promoting activity of phenylethyl isothio- cyanate and benzyl isothiocyanate on urinary bladder carcinogen- esis in F344 male rats. Int J Cancer 77:773-777.
    • (1998) Int J Cancer , vol.77 , pp. 773-777
    • Hirose, M.1    Yamaguchi, T.2    Kimoto, N.3    Ogawa, K.4    Futakuchi, M.5    Sano, M.6    Shirai, T.7
  • 11
    • 0029156562 scopus 로고
    • Biotransformation of organic sulfides. VII. Formation of chiral isothiocyanato sulf- oxides and related compounds by microbial biotransformation
    • Holland HL, Brown FM, Larsen BG, Zabic M. 1995. Biotransformation of organic sulfides. VII. Formation of chiral isothiocyanato sulf- oxides and related compounds by microbial biotransformation. Tetrahedron Asymmetry 6:1569-1574.
    • (1995) Tetrahedron Asymmetry , vol.6 , pp. 1569-1574
    • Holland, H.L.1    Brown, F.M.2    Larsen, B.G.3    Zabic, M.4
  • 12
    • 33749263503 scopus 로고    scopus 로고
    • Identification of Nrf2-regu- lated genes induced by chemopreventive isothiocyanate PEITC by oligonucleotide microarray
    • Hu R, Xu C, Shen G, Jain MR, Khor TO, Gopalkrishnan A, Lin W, Reddy B, Chan JY, Kong AN. 2006. Identification of Nrf2-regu- lated genes induced by chemopreventive isothiocyanate PEITC by oligonucleotide microarray. Life Sci 79:1944-1955.
    • (2006) Life Sci , vol.79 , pp. 1944-1955
    • Hu, R.1    Xu, C.2    Shen, G.3    Jain, M.R.4    Khor, T.O.5    Gopalkrishnan, A.6    Lin, W.7    Reddy, B.8    Chan, J.Y.9    Kong, A.N.10
  • 13
    • 0037205635 scopus 로고    scopus 로고
    • Aroma compound analysis of Eruca sativa (Brassicaceae) SPME headspace leaf samples using GC, GC-MS, and olfactometry
    • Jirovetz L, Smith D, Buchbauer G. 2002. Aroma compound analysis of Eruca sativa (Brassicaceae) SPME headspace leaf samples using GC, GC-MS, and olfactometry. J Agric Food Chem 50:4643-4646.
    • (2002) J Agric Food Chem , vol.50 , pp. 4643-4646
    • Jirovetz, L.1    Smith, D.2    Buchbauer, G.3
  • 14
    • 34247606510 scopus 로고    scopus 로고
    • Molecular basis for chemopreven- tion by sulforaphane: A comprehensive review
    • Juge N, Mithen RF, Traka M. 2007. Molecular basis for chemopreven- tion by sulforaphane: A comprehensive review. Cell Mol Life Sci 64:1105-1127.
    • (2007) Cell Mol Life Sci , vol.64 , pp. 1105-1127
    • Juge, N.1    Mithen, R.F.2    Traka, M.3
  • 15
    • 0343517520 scopus 로고    scopus 로고
    • Genotoxic effects of allyl isothiocyanate (AITC) and phenethyl isothiocyanate (PEITC)
    • Kassie F, Knasmuller S. 2000. Genotoxic effects of allyl isothiocyanate (AITC) and phenethyl isothiocyanate (PEITC). Chem Biol Interact 127:163-180.
    • (2000) Chem Biol Interact , vol.127 , pp. 163-180
    • Kassie, F.1    Knasmuller, S.2
  • 16
    • 0032728663 scopus 로고    scopus 로고
    • Genotoxic effects of benzyl isothiocyanate, a natural chemopreventive agent
    • Kassie F, Pool-Zobel B, Parzefall W, Knasmuller S. 1999. Genotoxic effects of benzyl isothiocyanate, a natural chemopreventive agent. Mutagen 14:595-604.
    • (1999) Mutagen , vol.14 , pp. 595-604
    • Kassie, F.1    Pool-Zobel, B.2    Parzefall, W.3    Knasmuller, S.4
  • 19
    • 0345708287 scopus 로고    scopus 로고
    • 3-Nitrobenzanthrone (3-NBA) induced micronucleus formation and DNA damage in human hepatoma (HepG2) cells
    • Lamy E, Kassie F, Gminski R, Schmeiser HH, Mersch-Sundermann V. 2004. 3-Nitrobenzanthrone (3-NBA) induced micronucleus formation and DNA damage in human hepatoma (HepG2) cells. Toxi- col Lett 146:103-109.
    • (2004) Toxi- col Lett , vol.146 , pp. 103-109
    • Lamy, E.1    Kassie, F.2    Gminski, R.3    Schmeiser, H.H.4    Mersch-Sundermann, V.5
  • 20
    • 46549087553 scopus 로고    scopus 로고
    • Antigenotoxic properties of Eruca sativa (rocket plant), erucin and erysolin in human hepatoma (HepG2) cells towards benzo(a)pyrene and their mode of action
    • Lamy E, Schroder J, Paulus S, Brenk P, Stahl T, Mersch-Sundermann V. 2008. Antigenotoxic properties of Eruca sativa (rocket plant), erucin and erysolin in human hepatoma (HepG2) cells towards benzo(a)pyrene and their mode of action. Food Chem Toxicol 46:2415-2421.
    • (2008) Food Chem Toxicol , vol.46 , pp. 2415-2421
    • Lamy, E.1    Schroder, J.2    Paulus, S.3    Brenk, P.4    Stahl, T.5    Mersch-Sundermann, V.6
  • 21
    • 0031428462 scopus 로고    scopus 로고
    • Mechanism of action of dietary chemoprotec- tive agents in rat liver: Induction of phase I and II drug metabo-lizing enzymes and aflatoxin B1 metabolism
    • Manson MM, Ball HW, Barrett MC, Clark HL, Judah DJ, Williamson G, Neal GE. 1997. Mechanism of action of dietary chemoprotec- tive agents in rat liver: Induction of phase I and II drug metabo-lizing enzymes and aflatoxin B1 metabolism. Carcinogenesis 18:1729-1738.
    • (1997) Carcinogenesis , vol.18 , pp. 1729-1738
    • Manson, M.M.1    Ball, H.W.2    Barrett, M.C.3    Clark, H.L.4    Judah, D.J.5    Williamson, G.6    Neal, G.E.7
  • 22
    • 0035670660 scopus 로고    scopus 로고
    • Toxic effects of benzyl and allyl isothiocya- nates and benzyl-isoform specific metabolites in the urinary bladder after a single intravesical application to rats
    • Masutomi N, Toyoda K, Shibutani M, Niho N, Uneyama C, Takahashi N, Hirose M. 2001. Toxic effects of benzyl and allyl isothiocya- nates and benzyl-isoform specific metabolites in the urinary bladder after a single intravesical application to rats. Toxicol Pathol 29:617-622.
    • (2001) Toxicol Pathol , vol.29 , pp. 617-622
    • Masutomi, N.1    Toyoda, K.2    Shibutani, M.3    Niho, N.4    Uneyama, C.5    Takahashi, N.6    Hirose, M.7
  • 23
    • 0024360557 scopus 로고
    • Effects of aromatic isothiocyanates on tumorigenicity, O6-methylguanine formation, and metabolism of the tobacco-specific nitrosamine 4-(methylni- trosamino)-1-(3-pyridyl)-1- butanone in A/J mouse lung
    • Morse MA, Amin SG, Hecht SS, Chung FL. 1989. Effects of aromatic isothiocyanates on tumorigenicity, O6-methylguanine formation, and metabolism of the tobacco-specific nitrosamine 4-(methylni- trosamino)-1-(3-pyridyl)-1- butanone in A/J mouse lung. Cancer Res 49:2894-2897.
    • (1989) Cancer Res , vol.49 , pp. 2894-2897
    • Morse, M.A.1    Amin, S.G.2    Hecht, S.S.3    Chung, F.L.4
  • 24
    • 0034932451 scopus 로고    scopus 로고
    • Inhibition and inactivation of human cytochrome P450 isoforms by phenethyl isothiocyanate
    • Nakajima M, Yoshida R, Shimada N, Yamazaki H, Yokoi T. 2001. Inhibition and inactivation of human cytochrome P450 isoforms by phenethyl isothiocyanate. Drug Metab Dispos 29:1110-1113.
    • (2001) Drug Metab Dispos , vol.29 , pp. 1110-1113
    • Nakajima, M.1    Yoshida, R.2    Shimada, N.3    Yamazaki, H.4    Yokoi, T.5
  • 25
    • 0025832194 scopus 로고
    • Use of human hepatoma cells for in vitro metabolic activation of chemical mutagens/carcinogens
    • Natarajan AT, Darroudi F. 1991. Use of human hepatoma cells for in vitro metabolic activation of chemical mutagens/carcinogens. Mu-tagen 6:399-403.
    • (1991) Mu-tagen , vol.6 , pp. 399-403
    • Natarajan, A.T.1    Darroudi, F.2
  • 26
    • 0345503639 scopus 로고
    • Carcinogenesis bioassay of allyl isothiocyanate (CAS No. 57-06-7) in F344/N rats and B6C3F1 mice (Gavage study)
    • National Toxicology Program N
    • National Toxicology Program N. 1982. Carcinogenesis bioassay of allyl isothiocyanate (CAS No. 57-06-7) in F344/N rats and B6C3F1 mice (Gavage study). Natl Toxicol Program Tech Rep Ser 234:1-142.
    • (1982) Natl Toxicol Program Tech Rep Ser , vol.234 , pp. 1-142
  • 27
    • 0035729374 scopus 로고    scopus 로고
    • Dose-dependent promotion by phenylethyl isothiocyanate, a known chemopreventer, of two-stage rat urinary bladder and liver carcinogenesis
    • Ogawa K, Hirose M, Sugiura S, Cui L, Imaida K, Ogiso T, Shirai T. 2001.Dose-dependent promotion by phenylethyl isothiocyanate, a known chemopreventer, of two-stage rat urinary bladder and liver carcinogenesis. Nutr Cancer 40:134-139.
    • (2001) Nutr Cancer , vol.40 , pp. 134-139
    • Ogawa, K.1    Hirose, M.2    Sugiura, S.3    Cui, L.4    Imaida, K.5    Ogiso, T.6    Shirai, T.7
  • 28
    • 0344237234 scopus 로고    scopus 로고
    • Enhancement of urinary bladder carcinogenesis by combined treatment with benzyl isothiocyanate and N-butyl-N-(4- hydroxybutyl)nitrosamine in rats after initiation
    • Okazaki K, Umemura T, Imazawa T, Nishikawa A, Masegi T, Hirose M. 2003. Enhancement of urinary bladder carcinogenesis by combined treatment with benzyl isothiocyanate and N-butyl-N-(4- hydroxybutyl)nitrosamine in rats after initiation. Cancer Sci 94:948-952.
    • (2003) Cancer Sci , vol.94 , pp. 948-952
    • Okazaki, K.1    Umemura, T.2    Imazawa, T.3    Nishikawa, A.4    Masegi, T.5    Hirose, M.6
  • 29
    • 0033006982 scopus 로고    scopus 로고
    • Sasaki T, Kudoh K, Uda Y, Ozawa Y, Shimizu J, Kanke Y, Takita T. 1999. Effects of isothiocyanates on growth and metastaticity of B16-F10 melanoma cells. Nutr Cancer 33:76-81. Schmid H, Karrer P. 1948. [Not available.]. Helv Chim Acta 31:1497-1505.
    • Sasaki T, Kudoh K, Uda Y, Ozawa Y, Shimizu J, Kanke Y, Takita T. 1999. Effects of isothiocyanates on growth and metastaticity of B16-F10 melanoma cells. Nutr Cancer 33:76-81. Schmid H, Karrer P. 1948. [Not available.]. Helv Chim Acta 31:1497-1505.
  • 30
    • 0037357453 scopus 로고    scopus 로고
    • Reversibility of proliferative lesions and induction of non- papillary tumors in rat urinary bladder treated with phenylethyl isothiocyanate
    • Sugiura S, Ogawa K, Hirose M, Takeshita F, Asamoto M, Shirai T. 2003. Reversibility of proliferative lesions and induction of non- papillary tumors in rat urinary bladder treated with phenylethyl isothiocyanate. Carcinogenesis 24:547-553.
    • (2003) Carcinogenesis , vol.24 , pp. 547-553
    • Sugiura, S.1    Ogawa, K.2    Hirose, M.3    Takeshita, F.4    Asamoto, M.5    Shirai, T.6
  • 31
    • 1942452892 scopus 로고    scopus 로고
    • Isothiocyanates in the chemoprevention of bladder cancer
    • Tang L, Zhang Y. 2004. Isothiocyanates in the chemoprevention of bladder cancer. Curr Drug Metab 5:193-201.
    • (2004) Curr Drug Metab , vol.5 , pp. 193-201
    • Tang, L.1    Zhang, Y.2
  • 32
    • 0025618481 scopus 로고
    • The single cell gel assay: A sensitive technique for evaluating intercellular differences in DNA damage and repair
    • Tice RR, Andrews PW, Singh NP. 1990. The single cell gel assay: A sensitive technique for evaluating intercellular differences in DNA damage and repair. Basic Life Sci 53:291-301.
    • (1990) Basic Life Sci , vol.53 , pp. 291-301
    • Tice, R.R.1    Andrews, P.W.2    Singh, N.P.3
  • 34
    • 0017328782 scopus 로고
    • Inhibition of carcinogenic effects of polycyclic hydrocarbons by benzyl isothiocyanate and related compounds
    • Wattenberg LW. 1977. Inhibition of carcinogenic effects of polycyclic hydrocarbons by benzyl isothiocyanate and related compounds. J Natl Cancer Inst 58:395-398.
    • (1977) J Natl Cancer Inst , vol.58 , pp. 395-398
    • Wattenberg, L.W.1
  • 35
    • 33645222035 scopus 로고    scopus 로고
    • Molecular mechanisms of adeno- sine-induced apoptosis in human HepG2 cells
    • Wu LF, Li GP, Feng JL, Pu ZJ. 2006. Molecular mechanisms of adeno- sine-induced apoptosis in human HepG2 cells. Acta Pharmacol Sin 27:477-484.
    • (2006) Acta Pharmacol Sin , vol.27 , pp. 477-484
    • Wu, L.F.1    Li, G.P.2    Feng, J.L.3    Pu, Z.J.4
  • 36
    • 0036135910 scopus 로고    scopus 로고
    • Quantitative determination of dithiocarbamates in human plasma, serum, erythrocytes and urine: Pharmacokinetics of broccoli sprout isothiocyanates in humans
    • Ye L, nkova-Kostova AT, Wade KL, Zhang Y, Shapiro TA, Talalay P. 2002. Quantitative determination of dithiocarbamates in human plasma, serum, erythrocytes and urine: Pharmacokinetics of broccoli sprout isothiocyanates in humans. Clin Chim Acta 316:43-53.
    • (2002) Clin Chim Acta , vol.316 , pp. 43-53
    • Ye, L.1    nkova-Kostova, A.T.2    Wade, K.L.3    Zhang, Y.4    Shapiro, T.A.5    Talalay, P.6
  • 37
    • 0028326168 scopus 로고
    • Anticarcinogenic activities of organic isothio- cyanates: Chemistry and mechanisms
    • Zhang Y, Talalay P. 1994. Anticarcinogenic activities of organic isothio- cyanates: Chemistry and mechanisms. Cancer Res 54(7 Suppl): 1976s-1981s.
    • (1994) Cancer Res , vol.54 , Issue.7 SUPPL.
    • Zhang, Y.1    Talalay, P.2
  • 38
    • 0026577605 scopus 로고
    • A major inducer of anticarcinogenic protective enzymes from broccoli: Isolation and elucidation of structure
    • Zhang Y, Talalay P, Cho CG, Posner GH. 1992. A major inducer of anticarcinogenic protective enzymes from broccoli: Isolation and elucidation of structure. Proc Natl Acad Sci USA 89:2399-2403.
    • (1992) Proc Natl Acad Sci USA , vol.89 , pp. 2399-2403
    • Zhang, Y.1    Talalay, P.2    Cho, C.G.3    Posner, G.H.4


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