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Volumn 22, Issue 3, 2009, Pages 536-542

Covalent modification of lysine residues by allyl isothiocyanate in physiological conditions: Plausible transformation of isothiocyanate from thiol to amine

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLCYSTEINE; ALLYL ISOTHIOCYANATE; AMINE; BOVINE SERUM ALBUMIN; BUFFER; LYSINE DERIVATIVE; MONOCLONAL ANTIBODY; N ALPHA BENZOYLGLYCYLLYSINE; THIOL; UNCLASSIFIED DRUG;

EID: 65949117445     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx8003906     Document Type: Article
Times cited : (75)

References (24)
  • 1
    • 29844448695 scopus 로고    scopus 로고
    • 6-Methylsulfinylhexyl isothiocyanate, an antioxidant derived from Wasabia japonica MATUM, ameliorates diabetic nephropathy in type 2 diabetic mice
    • Fukuchi, Y., Kato, Y., Okunishi, I., Matsutani, Y., Osawa, T., and Naito, M. (2004) 6-Methylsulfinylhexyl isothiocyanate, an antioxidant derived from wasabia japonica MATUM, ameliorates diabetic nephropathy in type 2 diabetic mice. Food Sci. Technol. Res. 10, 290-295. (Pubitemid 43034162)
    • (2004) Food Science and Technology Research , vol.10 , Issue.3 , pp. 290-295
    • Fukuch, Y.1    Kato, Y.2    Okunishi, I.3    Matsutani, Y.4    Osawa, T.5    Naito, M.6
  • 2
    • 0000411395 scopus 로고
    • Preliminary examination of allyl isothiocyanate vapor for food preservation
    • Isshiki, K., Tokuoka, K., Mori, R., and Chiba, S. (1992) Preliminary examination of allyl isothiocyanate vapor for food preservation. Biosci., Biotechnol., Biochem. 56, 1476-1477.
    • (1992) Biosci., Biotechnol., Biochem. , vol.56 , pp. 1476-1477
    • Isshiki, K.1    Tokuoka, K.2    Mori, R.3    Chiba, S.4
  • 3
  • 4
    • 0025369383 scopus 로고
    • Glutathione S-transferase subunit induction patterns of Brussels sprouts, allyl isothiocyanate and goitrin in rat liver and small intestinal mucosa: A new approach for the identification of inducing xenobiotics
    • DOI 10.1016/0278-6915(90)90014-E
    • Bogaards, J. J., Van, Ommen B., Falke, H. E., Willems, M. I., and Van, Bladeren P. J. (1990) Glutathione S-transferase subunit induction patterns of Brussels sprouts, allyl isothiocyanate and goitrin in rat liver and small intestinal mucosa: a new approach for the identification of inducing xenobiotics. Food Chem. Toxicol. 28, 81-88. (Pubitemid 20170904)
    • (1990) Food and Chemical Toxicology , vol.28 , Issue.2 , pp. 81-88
    • Bogaards, J.J.P.1    Van Ommen, B.2    Falke, H.E.3    Willems, M.I.4    Van Bladeren, P.J.5
  • 5
    • 0036949429 scopus 로고    scopus 로고
    • Selective induction of phase II enzymes in the urinary bladder of rats by allyl isothiocyanate, a compound derived from Brassica vegetables
    • Munday, R., and Munday, C. M. (2002) Selective induction of phase II enzymes in the urinary bladder of rats by allyl isothiocyanate, a compound derived from Brassica vegetables. Nutr. Cancer 44, 52-59. (Pubitemid 36359320)
    • (2002) Nutrition and Cancer , vol.44 , Issue.1 , pp. 52-59
    • Munday, R.1    Munday, C.M.2
  • 6
    • 1842588301 scopus 로고    scopus 로고
    • Induction of phase II detoxification enzymes in rats by plant-derived isothiocyanates: Comparison of allyl isothiocyanate with sulforaphane and related compounds
    • Munday, R., and Munday, C. M. (2004) Induction of phase II detoxification enzymes in rats by plant-derived isothiocyanates: comparison of allyl isothiocyanate with sulforaphane and related compounds. J. Agric. Food Chem. 52, 1867-1871.
    • (2004) J. Agric. Food Chem. , vol.52 , pp. 1867-1871
    • Munday, R.1    Munday, C.M.2
  • 7
    • 0034490924 scopus 로고    scopus 로고
    • Antiplatelet and anticancer isothiocyanates in japanese domestic horseradish, wasabi
    • Morimitsu, Y., Hayashi, K., Nakagawa, Y., Horio, F., Uchida, K., and Osawa, T. (2000) Antiplatelet and anticancer isothiocyanates in Japanese domestic horseradish, wasabi. BioFactors 13, 271-276. (Pubitemid 32107375)
    • (2000) BioFactors , vol.13 , Issue.1-4 , pp. 271-276
    • Morimitsu, Y.1    Hayashi, K.2    Nakagawa, Y.3    Horio, F.4    Uchida, K.5    Osawa, T.6
  • 8
    • 0034695172 scopus 로고    scopus 로고
    • Transcriptional regulation of nicotinamide adenine dinucleotide phosphate: Quinone oxidoreductase in murine hepatoma cells by 6-(methylsufinyl)hexyl isothiocyanate an active principle of wasabi (Eutrema wasabi Maxim)
    • Hou, D. X., Fukuda, M., Fujii, M., and Fuke, Y. (2000) Transcriptional regulation of nicotinamide adenine dinucleotide phosphate: quinone oxidoreductase in murine hepatoma cells by 6-(methylsufinyl)hexyl isothiocyanate, an active principle of wasabi (Eutrema wasabi Maxim). Cancer Lett. 161, 195-200.
    • (2000) Cancer Lett. , vol.161 , pp. 195-200
    • Hou, D.X.1    Fukuda, M.2    Fujii, M.3    Fuke, Y.4
  • 9
    • 17044398534 scopus 로고    scopus 로고
    • elective sensitivity to wasabi-derived 6-(methylsulfinyl)hexyl isothiocyanate of human breast cancer and melanoma cell lines studied in vitro
    • Nomura, T., Shinoda, S., Yamori, T., Sawaki, S., Nagata, I., Ryoyama, K., and Fuke, Y. (2005) Selective sensitivity to wasabi-derived 6-(methylsulfinyl)hexyl isothiocyanate of human breast cancer and melanoma cell lines studied in vitro. Cancer Detect. Prev. 29, 155-160.
    • (2005) Cancer Detect. Prev. , vol.29 , pp. 155-160
    • Nomura, T.1    Shinoda, S.2    Yamori, T.3    Sawaki, S.4    Nagata, I.5    Ryoyama, K.6    Fuke, Y.7
  • 10
    • 0026577605 scopus 로고
    • A major inducer of anticarcinogenic protective enzymes from broccoli: Isolation and elucidation of structure
    • Zhang, Y., Talalay, P., Cho, C. G., and Posner, G. H. (1992) A major inducer of anticarcinogenic protective enzymes from broccoli: isolation and elucidation of structure. Proc. Natl. Acad. Sci. U.S.A. 89, 2399-2403.
    • (1992) Proc. Natl. Acad. Sci. U.S.A. , vol.89 , pp. 2399-2403
    • Zhang, Y.1    Talalay, P.2    Cho, C.G.3    Posner, G.H.4
  • 11
    • 33745527173 scopus 로고    scopus 로고
    • Cell death induction by isothiocyanates and their underlying molecular mechanisms
    • Nakamura, Y., and Miyoshi, N. (2006) Cell death induction by isothiocyanates and their underlying molecular mechanisms. Bio-Factors 26, 123-134. (Pubitemid 43979364)
    • (2006) BioFactors , vol.26 , Issue.2 , pp. 123-134
    • Nakamura, Y.1    Miyoshi, N.2
  • 12
    • 33746130073 scopus 로고    scopus 로고
    • Phenethyl isothiocyanate triggers apoptosis in jurkat cells made resistant by the overexpression of Bcl-2
    • DOI 10.1158/0008-5472.CAN-05-3809
    • Thomson, S. J., Brown, K. K., Pullar, J. M., and Hampton, M. B. (2006) Phenethyl isothiocyanate triggers apoptosis in Jurkat cells made resistant by the overexpression of Bcl-2. Cancer Res. 66, 6772-6777. (Pubitemid 44085636)
    • (2006) Cancer Research , vol.66 , Issue.13 , pp. 6772-6777
    • Thomson, S.J.1    Brown, K.K.2    Pullar, J.M.3    Hampton, M.B.4
  • 13
    • 29644443964 scopus 로고    scopus 로고
    • Identification of sensor cysteines in human Keap1 modified by the cancer chemopreventive agent sulforaphane
    • DOI 10.1021/tx0502138
    • Hong, F., Freeman, M. L., and Liebler, D. C. (1917) (2005) Identification of sensor cysteines in human Keap 1 modified by the cancer chemopreventive agent sulforaphane. Chem. Res. Toxicol. 18 1926. (Pubitemid 43023050)
    • (2005) Chemical Research in Toxicology , vol.18 , Issue.12 , pp. 1917-1926
    • Hong, F.1    Freeman, M.L.2    Liebler, D.C.3
  • 14
    • 0030781225 scopus 로고    scopus 로고
    • Biotransformation of the naturally occurring isothiocyanate sulforaphane in the rat: Identification of phase I metabolites and glutathione conjugates
    • DOI 10.1021/tx970080t
    • Kassahun, K., Davis, M., Hu, P., Martin, B., and Baillie, T. (1997) Biotransformation of the naturally occurring isothiocyanate sulforaphane in the rat: identification of phase I metabolites and glutathione conjugates. Chem. Res. Toxicol. 10, 1228-1233. (Pubitemid 27524827)
    • (1997) Chemical Research in Toxicology , vol.10 , Issue.11 , pp. 1228-1233
    • Kassahun, K.1    Davis, M.2    Hu, P.3    Martin, B.4    Baillie, T.5
  • 16
    • 0037015035 scopus 로고    scopus 로고
    • Direct evidence that sulfhydryl groups of Keap1 are the sensors regulating induction of phase 2 enzymes that protect against carcinogens and oxidants
    • Dinkova-Kostova, A. T., Holtzclaw, W. D., Cole, R. N., Itoh, K., Wakabayashi, N., katoh, Y., Yamamoto, M., and Talalay, P. (2002) Direct evidence that sulfhydryl groups of Keap1 are the sensors regulating induction of phase 2 enzymes that protect against carcinogens and oxidants. Proc. Natl. Acad. Sci. U.S.A. 99, 11908-11913.
    • (2002) Proc. Natl. Acad. Sci. U.S.A. , vol.99 , pp. 11908-11913
    • Dinkova-Kostova, A.T.1    Holtzclaw, W.D.2    Cole, R.N.3    Itoh, K.4    Wakabayashi, N.5    Katoh, Y.6    Yamamoto, M.7    Talalay, P.8
  • 18
    • 0023221153 scopus 로고
    • Oxidation of human low density lipoprotein results in derivatization of lysine residues of apolipoprotein B by lipid peroxide decomposition products
    • Steinbrecher, U. P. (1987) Oxidation of human low density lipoprotein results in derivatization of lysine residues of apolipoprotein B by lipid peroxide decomposition products. J. Biol. Chem. 262, 3603-3608. (Pubitemid 17132923)
    • (1987) Journal of Biological Chemistry , vol.262 , Issue.8 , pp. 3603-3608
    • Steinbrecher, U.P.1
  • 19
    • 0028823203 scopus 로고
    • Protein modification by the degradation products of ascorbate: Formation of a novel pyrrole from the Maillard reaction of L-threose with proteins
    • Nagaraj, R. H., and Monnier, V. M. (1995) Protein modification by the degradation products of ascorbate: formation of a novel pyrrole from the Maillard reaction of L-threose with proteins. Biochim. Biophys. Acta 1253, 75-84.
    • (1995) Biochim. Biophys. Acta , vol.1253 , pp. 75-84
    • Nagaraj, R.H.1    Monnier, V.M.2
  • 20
    • 0034682979 scopus 로고    scopus 로고
    • Immunochemical detection of protein dityrosine in atherosclerotic lesion of Apo-E-deficient mice using a novel monoclonal antibody
    • DOI 10.1006/bbrc.2000.3265
    • Kato, Y., Wu, X., Naito, M., Nomura, H., Kitamoto, N., and Osawa, T. (2000) Immunochemical detection of protein dityrosine in atherosclerotic lesion of apo-E-deficient mice using a novel monoclonal antibody. Biochem. Biophys. Res. Commun. 275, 11-15. (Pubitemid 30663620)
    • (2000) Biochemical and Biophysical Research Communications , vol.275 , Issue.1 , pp. 11-15
    • Kato, Y.1    Wu, X.2    Naito, M.3    Nomura, H.4    Kitamoto, N.5    Osawa, T.6
  • 21
    • 0012052528 scopus 로고
    • Oxidative scission of the disulfide bond of cystine and polypeptides by the action of allyl isothiocyanate
    • Kawakishi, S., Goto, T., and Namiki, M. (1983) Oxidative scission of the disulfide bond of cystine and polypeptides by the action of allyl isothiocyanate. Agric. Biol. Chem. 47, 2071-2076.
    • (1983) Agric. Biol. Chem. , vol.47 , pp. 2071-2076
    • Kawakishi, S.1    Goto, T.2    Namiki, M.3
  • 22
    • 33746268137 scopus 로고    scopus 로고
    • Identification of Specific Protein Carbonylation Sites in Model Oxidations of Human Serum Albumin
    • DOI 10.1016/j.jasms.2006.04.030, PII S1044030506003928
    • Temple, A., Yen, T. Y., and Gronert, S. (2006) Identification of specific protein carbonylation sites in model oxidations of human serum albumin. J. Am. Soc. Mass Spectrom. 17, 1172-1180. (Pubitemid 44094131)
    • (2006) Journal of the American Society for Mass Spectrometry , vol.17 , Issue.8 , pp. 1172-1180
    • Temple, A.1    Yen, T.-Y.2    Gronert, S.3
  • 23
    • 0034808331 scopus 로고    scopus 로고
    • Decomposition rates of isothiocyanate conjugates determine their activity as inhibitors of cytochrome P450 enzymes
    • DOI 10.1021/tx010029w
    • Conaway, C. C., Krzeminski, J., Amin, S., and Chung, F. L. (2001) Decomposition rates of isothiocyanate conjugates determine their activity as inhibitors of cytochrome p450 enzymes. Chem. Res. Toxicol. 14, 1170-1176. (Pubitemid 32911454)
    • (2001) Chemical Research in Toxicology , vol.14 , Issue.9 , pp. 1170-1176
    • Conaway, C.C.1    Krzeminski, J.2    Amin, S.3    Chung, F.-L.4
  • 24
    • 0034662433 scopus 로고    scopus 로고
    • Studies on the mechanism of the inhibition of human leukaemia cell growth by dietary isothiocyanates and their cysteine adducts in vitro
    • DOI 10.1016/S0006-2952(00)00319-1, PII S0006295200003191
    • Xu, K., and Thornalley, P. J. (2000) Studies on the mechanism of the inhibition of human leukaemia cell growth by dietary isothiocyanates and their cysteine adducts in vitro. Biochem. Pharmacol. 60, 221-231. (Pubitemid 30312950)
    • (2000) Biochemical Pharmacology , vol.60 , Issue.2 , pp. 221-231
    • Xu, K.1    Thornalley, P.J.2


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