메뉴 건너뛰기




Volumn 92, Issue 4, 2005, Pages 690-695

Benzo[b]thiophenesulphonamide 1,1-dioxide derivatives inhibit tNOX activity in a redox state-dependent manner

Author keywords

Antineoplasic drugs; benzo b thiophenesulphonamides; ECTO NOX; Redox state; Tumour associated NADH oxidase

Indexed keywords

1 (4 CHLOROPHENYL) 3 (4 METHYLPHENYLSULFONYL)UREA; 6 [N (2 PHENYLETHYL)]BENZO[B]THIOPHENESULFONAMIDE 1,1 DIOXIDE; BENZO[B]THIOPHENESULFONAMIDE 1,1 DIOXIDE DERIVATIVE; BENZOTHIOPHENE DERIVATIVE; CYTOTOXIC AGENT; GLUTATHIONE; REACTIVE OXYGEN METABOLITE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE DEHYDROGENASE; UNCLASSIFIED DRUG; ANTINEOPLASTIC AGENT; BTS 1 COMPOUND; BTS 2 COMPOUND; BTS-1 COMPOUND; BTS-2 COMPOUND; ENZYME INHIBITOR; OXIDOREDUCTASE; SULFONAMIDE; THIOPHENE DERIVATIVE; TUMOR ASSOCIATED NADH OXIDASE; TUMOR PROTEIN; TUMOR-ASSOCIATED NADH OXIDASE;

EID: 14944347557     PISSN: 00070920     EISSN: None     Source Type: Journal    
DOI: 10.1038/sj.bjc.6602383     Document Type: Article
Times cited : (33)

References (36)
  • 1
    • 0036478839 scopus 로고    scopus 로고
    • Role of the retinoblastoma (pRb)-E2F/DP pathway in cancer chemopreventive effects of green tea polyphenol epigallocatechin-3-gallate
    • Ahmad N, Adhami VM, Gupta S, Cheng P, Mukhtar H (2002) Role of the retinoblastoma (pRb)-E2F/DP pathway in cancer chemopreventive effects of green tea polyphenol epigallocatechin-3-gallate. Arch Biochem Biophys 398: 125-131
    • (2002) Arch Biochem Biophys , vol.398 , pp. 125-131
    • Ahmad, N.1    Adhami, V.M.2    Gupta, S.3    Cheng, P.4    Mukhtar, H.5
  • 2
    • 0031444312 scopus 로고    scopus 로고
    • Green tea constituent epigallocatechin-3-gallate and induction of apoptosis and cell cycle arrest in human carcinoma cells
    • Ahmad N, Feyes DK, Nieminen AL, Agarwal R, Mukhtar H (1997) Green tea constituent epigallocatechin-3-gallate and induction of apoptosis and cell cycle arrest in human carcinoma cells. J Natl Cancer Inst 89: 1881-1886
    • (1997) J Natl Cancer Inst , vol.89 , pp. 1881-1886
    • Ahmad, N.1    Feyes, D.K.2    Nieminen, A.L.3    Agarwal, R.4    Mukhtar, H.5
  • 3
    • 0034655603 scopus 로고    scopus 로고
    • Green tea polyphenol epigallocatechin-3-gallate differentially modulates nuclear factor kappaB in cancer cells versus normal cells
    • Ahmad N, Gupta S, Mukhtar H (2000) Green tea polyphenol epigallocatechin-3-gallate differentially modulates nuclear factor kappaB in cancer cells versus normal cells. Arch Biochem Biophys 376: 338-346
    • (2000) Arch Biochem Biophys , vol.376 , pp. 338-346
    • Ahmad, N.1    Gupta, S.2    Mukhtar, H.3
  • 4
    • 0037871874 scopus 로고    scopus 로고
    • New benzo(b)thiophenesulphonamide 1,1-dioxide derivatives induce a reactive oxygen species-mediated process of apoptosis in tumor cells
    • Alonso MM, Asumendi A, Villar J, Gil MJ, Martínez-Merino V, Encío I, Migliaccio M (2003) New benzo(b)thiophenesulphonamide 1,1-dioxide derivatives induce a reactive oxygen species-mediated process of apoptosis in tumor cells. Oncogene 22: 3759-3769
    • (2003) Oncogene , vol.22 , pp. 3759-3769
    • Alonso, M.M.1    Asumendi, A.2    Villar, J.3    Gil, M.J.4    Martínez-Merino, V.5    Encío, I.6    Migliaccio, M.7
  • 5
    • 0035798435 scopus 로고    scopus 로고
    • New cytotoxic benzo(b)thiophenilsulfonamide 1,1-dioxide derivatives inhibit a NADH oxidase located in plasma membranes of tumor cells
    • Alonso MM, Encío I, Martínez-Merino V, Gil MJ, Migliaccio M (2001) New cytotoxic benzo(b)thiophenilsulfonamide 1,1-dioxide derivatives inhibit a NADH oxidase located in plasma membranes of tumor cells. Br J Cancer 85: 1400-1402
    • (2001) Br J Cancer , vol.85 , pp. 1400-1402
    • Alonso, M.M.1    Encío, I.2    Martínez-Merino, V.3    Gil, M.J.4    Migliaccio, M.5
  • 6
    • 0010315601 scopus 로고
    • Benzothiophen chemistry. VI. A peroxide effect in the addition of thiophenols to benzothiophene 1-dioxide
    • Bordwell FG, Chapman RD, McKellin WH (1954) Benzothiophen chemistry. VI. A peroxide effect in the addition of thiophenols to benzothiophene 1-dioxide. J Am Chem Soc 76: 3637-3639
    • (1954) J Am Chem Soc , vol.76 , pp. 3637-3639
    • Bordwell, F.G.1    Chapman, R.D.2    McKellin, W.H.3
  • 7
    • 37049147783 scopus 로고
    • Some derivatives of thionaphthen
    • Challenger F, Clapham PH (1948) Some derivatives of thionaphthen. J Chem Soc (oct): 1615-1618
    • (1948) J Chem Soc , Issue.OCT , pp. 1615-1618
    • Challenger, F.1    Clapham, P.H.2
  • 8
    • 0034725523 scopus 로고    scopus 로고
    • Tyr115, gln165 and trp209 contribute to the 1, 2-epoxy-3-(p-nitrophenoxy) propane-conjugating activity of glutathione S-transferase cGSTM1-1
    • Chern MK, Wu TC, Hsieh CH, Chou CC, Liu LF, Kuan IC, Yeh YH, Hsiao CD, Ming F, Tam MF (2000) Tyr115, gln165 and trp209 contribute to the 1, 2-epoxy-3-(p-nitrophenoxy)propane-conjugating activity of glutathione S-transferase cGSTM1-1. J Mol Biol 300: 1257-1269
    • (2000) J Mol Biol , vol.300 , pp. 1257-1269
    • Chern, M.K.1    Wu, T.C.2    Hsieh, C.H.3    Chou, C.C.4    Liu, L.F.5    Kuan, I.C.6    Yeh, Y.H.7    Hsiao, C.D.8    Ming, F.9    Tam, M.F.10
  • 9
    • 0037133540 scopus 로고    scopus 로고
    • Molecular cloning and characterization of a tumor-associated, growth-related, and time-keeping hydroquinone (NADH) oxidase (tNOX) of the HeLa cell surface
    • Chueh PJ, Kim C, Cho N, Morré DM, Morré DJ (2002a) Molecular cloning and characterization of a tumor-associated, growth-related, and time-keeping hydroquinone (NADH) oxidase (tNOX) of the HeLa cell surface. Biochemistry 41: 3732-3741
    • (2002) Biochemistry , vol.41 , pp. 3732-3741
    • Chueh, P.J.1    Kim, C.2    Cho, N.3    Morré, D.M.4    Morré, D.J.5
  • 10
    • 0037203806 scopus 로고    scopus 로고
    • A site-directed mutagenesis analysis of tNOX functional domains
    • Chueh PJ, Morré DM, Morré DJ (2002b) A site-directed mutagenesis analysis of tNOX functional domains. Biochim Biophys Acta 1594: 74-83
    • (2002) Biochim Biophys Acta , vol.1594 , pp. 74-83
    • Chueh, P.J.1    Morré, D.M.2    Morré, D.J.3
  • 13
    • 0034177207 scopus 로고    scopus 로고
    • Growth inhibition, cell-cycle dysregulation, and induction of apoptosis by green tea constituent (-)-epigallocatechin-3-gallate in androgen-sensitive and androgen-insensitive human prostate carcinoma cells
    • Gupta S, Ahmad N, Nieminen AL, Mukhtar H (2000) Growth inhibition, cell-cycle dysregulation, and induction of apoptosis by green tea constituent (-)-epigallocatechin-3-gallate in androgen-sensitive and androgen-insensitive human prostate carcinoma cells. Toxicol Appl Pharmacol 164: 82-90
    • (2000) Toxicol Appl Pharmacol , vol.164 , pp. 82-90
    • Gupta, S.1    Ahmad, N.2    Nieminen, A.L.3    Mukhtar, H.4
  • 14
    • 0037667821 scopus 로고    scopus 로고
    • Adriamycin tolerance in human mesothelioma lines and cell surface NADH oxidase
    • Hedges KL, Morré DM, Wub LY, Morré DJ (2003) Adriamycin tolerance in human mesothelioma lines and cell surface NADH oxidase. Life Sci 73: 1189-1198
    • (2003) Life Sci , vol.73 , pp. 1189-1198
    • Hedges, K.L.1    Morré, D.M.2    Wub, L.Y.3    Morré, D.J.4
  • 15
    • 0024421234 scopus 로고
    • Substrate binding and catalysis by glutathione reductase as derived from refined enzyme: Substrate crystal structures at 2 Å resolution
    • Karplus PA, Schulz GE (1989) Substrate binding and catalysis by glutathione reductase as derived from refined enzyme: substrate crystal structures at 2 Å resolution. J Mol Biol 210: 163-180
    • (1989) J Mol Biol , vol.210 , pp. 163-180
    • Karplus, P.A.1    Schulz, G.E.2
  • 16
    • 0037053381 scopus 로고    scopus 로고
    • Purification and characterization of a doxorubicin-inhibited NADH-quinone (NADH-ferricyanide) reductase from rat liver plasma membranes
    • Kim C, Crane FL, Faulk WP, Morré DJ (2002) Purification and characterization of a doxorubicin-inhibited NADH-quinone (NADH-ferricyanide) reductase from rat liver plasma membranes. J Biol Chem 277: 16441-16447
    • (2002) J Biol Chem , vol.277 , pp. 16441-16447
    • Kim, C.1    Crane, F.L.2    Faulk, W.P.3    Morré, D.J.4
  • 17
    • 16244400606 scopus 로고    scopus 로고
    • (2000) Benzo[b]thiophene sulfonamide-1,1-dioxido derivatives and their use as antineoplastic agents. WO Patent 00/63202
    • Martínez-Merino V, Gil MJ, Encío I, Migliaccio M, Arteaga C (2000) Benzo[b]thiophene sulfonamide-1,1-dioxido derivatives and their use as antineoplastic agents. WO Patent 00/63202
    • Martínez-Merino, V.1    Gil, M.J.2    Encío, I.3    Migliaccio, M.4    Arteaga, C.5
  • 19
    • 0000891550 scopus 로고
    • Verfahren zur herstellung aromatischer sulfonsäurechloride, eine neue modifikation der Sandmeyerschen reaktion
    • Meerwein H, Dittmer G, Gollner R (1957) Verfahren zur herstellung aromatischer sulfonsäurechloride, eine neue modifikation der Sandmeyerschen reaktion. Chem Ver 90: 841-1178
    • (1957) Chem Ver , vol.90 , pp. 841-1178
    • Meerwein, H.1    Dittmer, G.2    Gollner, R.3
  • 20
    • 0028807965 scopus 로고
    • The antitumor sulfonylurea N-(4-methylphenylsulfonyl)-N′-(4- chlorophenyl) urea (LY181984) inhibits NADH oxidase activity of HeLa plasma membranes
    • Morŕ DJ, Wu LY, Morré DM (1995b) The antitumor sulfonylurea N-(4-methylphenylsulfonyl)-N′-(4-chlorophenyl) urea (LY181984) inhibits NADH oxidase activity of HeLa plasma membranes. Biochim Biophys Acta 1240: 11-17
    • (1995) Biochim Biophys Acta , vol.1240 , pp. 11-17
    • Morŕ, D.J.1    Wu, L.Y.2    Morré, D.M.3
  • 21
    • 0034057899 scopus 로고    scopus 로고
    • Chemical hormesis in cell growth: A molecular target at the cell surface
    • Morré DJ (2000) Chemical hormesis in cell growth: a molecular target at the cell surface. J Appl Toxicol 20: 157-163
    • (2000) J Appl Toxicol , vol.20 , pp. 157-163
    • Morré, D.J.1
  • 22
    • 0034308086 scopus 로고    scopus 로고
    • Preferential inhibition by (-)-epigallocatechin-3-gallate of the cell surface NADH oxidase and growth of transformed cells in culture
    • Morré DJ, Bridge A, Wu LY, Morré DM (2000) Preferential inhibition by (-)-epigallocatechin-3-gallate of the cell surface NADH oxidase and growth of transformed cells in culture. Biochem Pharmacol 60: 937-946
    • (2000) Biochem Pharmacol , vol.60 , pp. 937-946
    • Morré, D.J.1    Bridge, A.2    Wu, L.Y.3    Morré, D.M.4
  • 23
    • 0031570783 scopus 로고    scopus 로고
    • NADH oxidase activity from sera altered by capsaicin is widely distributed among cancer patients
    • Morré DJ, Caldwell S, Mayorga A, Wu LY, Morré DM (1997a) NADH oxidase activity from sera altered by capsaicin is widely distributed among cancer patients. Arch Biochem Biophys 342: 224-230
    • (1997) Arch Biochem Biophys , vol.342 , pp. 224-230
    • Morré, D.J.1    Caldwell, S.2    Mayorga, A.3    Wu, L.Y.4    Morré, D.M.5
  • 24
    • 0028925916 scopus 로고
    • Capsaicin inhibits preferentially the NADH oxidase and growth of transformed cells in culture
    • Morré DJ, Chueh PJ, Morré DM (1995c) Capsaicin inhibits preferentially the NADH oxidase and growth of transformed cells in culture. Proc Natl Acad Sci USA 92: 1831-1835
    • (1995) Proc Natl Acad Sci USA , vol.92 , pp. 1831-1835
    • Morré, D.J.1    Chueh, P.J.2    Morré, D.M.3
  • 25
    • 0030777179 scopus 로고    scopus 로고
    • Is the drug-responsive NADH oxidase of the cancer cell plasma membrane a molecular target for adriamycin
    • Morré DJ, Kim C, Paulik M, Morré DM, Faulk WP (1997c) Is the drug-responsive NADH oxidase of the cancer cell plasma membrane a molecular target for adriamycin. J Bioenerg Biomembr 29: 269-280
    • (1997) J Bioenerg Biomembr , vol.29 , pp. 269-280
    • Morré, D.J.1    Kim, C.2    Paulik, M.3    Morré, D.M.4    Faulk, W.P.5
  • 26
    • 0043198154 scopus 로고    scopus 로고
    • Cell surface NADH oxidases (ECTO-NOX proteins) with roles in cancer, cellular time-keeping, growth, aging and neurodegenerative diseases
    • Morré DJ, Morré DM (2003) Cell surface NADH oxidases (ECTO-NOX proteins) with roles in cancer, cellular time-keeping, growth, aging and neurodegenerative diseases. Free Radic Res 37: 795-808
    • (2003) Free Radic Res , vol.37 , pp. 795-808
    • Morré, D.J.1    Morré, D.M.2
  • 28
    • 0030854118 scopus 로고    scopus 로고
    • A circulating form of NADH oxidase activity responsive to the antitumor sulfonylurea N-4-(methylphenylsulfonyl)-N′-(4-chlorophenyl)urea (LY181984) specific to sera from cancer patients
    • Morré DJ, Reust T (1997b) A circulating form of NADH oxidase activity responsive to the antitumor sulfonylurea N-4-(methylphenylsulfonyl)- N′-(4-chlorophenyl)urea (LY181984) specific to sera from cancer patients. J Bioenerg Biomembr 29: 281-289
    • (1997) J Bioenerg Biomembr , vol.29 , pp. 281-289
    • Morré, D.J.1    Reust, T.2
  • 29
    • 0032473385 scopus 로고    scopus 로고
    • Response of a cell-surface NADH oxidase to the antitumor sulfonylurea N-(4-methylphenylsulfonyl)-N′-(4-chlorophenylurea) (LY181984) modulated by redox
    • Morré DJ, Wu LY, Morré DM (1998) Response of a cell-surface NADH oxidase to the antitumor sulfonylurea N-(4-methylphenylsulfonyl)-N′- (4-chlorophenylurea) (LY181984) modulated by redox. Biochim Biophys Acta 1369: 185-192
    • (1998) Biochim Biophys Acta , vol.1369 , pp. 185-192
    • Morré, D.J.1    Wu, L.Y.2    Morré, D.M.3
  • 30
    • 0021061819 scopus 로고
    • Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays
    • Mosmann T (1983) Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 65: 55-59
    • (1983) J Immunol Methods , vol.65 , pp. 55-59
    • Mosmann, T.1
  • 31
    • 0037141470 scopus 로고    scopus 로고
    • Flavonoids uptake and their effect on cell cycle of human colon adenocarcinoma cells (Caco2)
    • Salucci M, Stivala LA, Maiani G, Bugianesi R, Vannini V (2002) Flavonoids uptake and their effect on cell cycle of human colon adenocarcinoma cells (Caco2). Br J Cancer 86: 1645-1651
    • (2002) Br J Cancer , vol.86 , pp. 1645-1651
    • Salucci, M.1    Stivala, L.A.2    Maiani, G.3    Bugianesi, R.4    Vannini, V.5
  • 32
    • 0035242490 scopus 로고    scopus 로고
    • A drug-unresponsive and protease-resistant CNOX protein from human sera
    • Sedlak D, Morré DM, Morré DJ (2001) A drug-unresponsive and protease-resistant CNOX protein from human sera. Arch Biochem Biophys 386: 106-116
    • (2001) Arch Biochem Biophys , vol.386 , pp. 106-116
    • Sedlak, D.1    Morré, D.M.2    Morré, D.J.3
  • 34
    • 0019986638 scopus 로고
    • The anticancer agent adriamycin can be actively cytotoxic without entering cells
    • Tritton RR, Yee G (1982) The anticancer agent adriamycin can be actively cytotoxic without entering cells. Science 217: 248-250
    • (1982) Science , vol.217 , pp. 248-250
    • Tritton, R.R.1    Yee, G.2
  • 35
    • 1342343129 scopus 로고    scopus 로고
    • Synthesis and cytotoxic activity of lipophilic sulphonamide derivatives of the benzo[b]thiophene 1,1-dioxide
    • Villar R, Encío I, Migliaccio M, Gil MJ, Martínez-Merino V (2004) Synthesis and cytotoxic activity of lipophilic sulphonamide derivatives of the benzo[b]thiophene 1,1-dioxide. Bioorg Med Chem 12: 963-968
    • (2004) Bioorg Med Chem , vol.12 , pp. 963-968
    • Villar, R.1    Encío, I.2    Migliaccio, M.3    Gil, M.J.4    Martínez-Merino, V.5
  • 36
    • 0037455919 scopus 로고    scopus 로고
    • Sera from cancer patients contain two oscillating ECTO-NOX activities with different period lengths
    • Wang S, Morré DM, Morré DJ (2003) Sera from cancer patients contain two oscillating ECTO-NOX activities with different period lengths. Cancer Lett 190: 135-141
    • (2003) Cancer Lett , vol.190 , pp. 135-141
    • Wang, S.1    Morré, D.M.2    Morré, D.J.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.