메뉴 건너뛰기




Volumn 17, Issue 6 D, 1997, Pages 4599-4605

Diaryl chalcogenides as selective inhibitors of thioredoxin reductase and potential antitumor agents

Author keywords

Antitumor activity; Organoselenium; Organotellurium; Thioredoxin reductase

Indexed keywords

ANTINEOPLASTIC AGENT; DIARYL CHALCOGENIDE; EBSELEN; ENZYME INHIBITOR; FLAVOPROTEIN; GLUTATHIONE REDUCTASE; ORGANOSELENIUM DERIVATIVE; ORGANOTELLURIUM DERIVATIVE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; SELENOCYSTEINE; THIOREDOXIN; THIOREDOXIN REDUCTASE; UNCLASSIFIED DRUG;

EID: 0031425497     PISSN: 02507005     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (119)

References (47)
  • 1
    • 0010441477 scopus 로고
    • Cloning and expression of thioredoxin (T) cDNA from human colon cancer cells. Identity with ADF and levels of T mRNA in human tumors
    • Gasda ka P, Oblong JE and Powis G: Cloning and expression of thioredoxin (T) cDNA from human colon cancer cells. Identity with ADF and levels of T mRNA in human tumors. Proc Am Assoc Cancer Res 34: 62, 1993.
    • (1993) Proc Am Assoc Cancer Res , vol.34 , pp. 62
    • Gasda ka, P.1    Oblong, J.E.2    Powis, G.3
  • 2
    • 0030588144 scopus 로고    scopus 로고
    • Human thioredoxin reductase gene localization to chromosomal position 12q23->q24.1 and mRNA distribution in human tissue
    • Gasdaska JR, Gasdaska PY, Gallegos A and Powis G: Human thioredoxin reductase gene localization to chromosomal position 12q23->q24.1 and mRNA distribution in human tissue. Genomics 37: 257-259, 1996.
    • (1996) Genomics , vol.37 , pp. 257-259
    • Gasdaska, J.R.1    Gasdaska, P.Y.2    Gallegos, A.3    Powis, G.4
  • 4
    • 78651146370 scopus 로고
    • Enzymatic synthesis of deoxyribonucleotides VI. Isolation and characterization of thioredoxin, the hydrogen donor frorn Escherichia coli B
    • Laurent TC, Moore EC and Reichard P: Enzymatic synthesis of deoxyribonucleotides VI. Isolation and characterization of thioredoxin, the hydrogen donor frorn Escherichia coli B J Biol Chem 239: 3436-3444, 1964.
    • (1964) J Biol Chem , vol.239 , pp. 3436-3444
    • Laurent, T.C.1    Moore, E.C.2    Reichard, P.3
  • 5
    • 0026715172 scopus 로고
    • Thioredoxin regulates the DNA binding activity of NF-kappaB by reduction of a disulphide bond involving cysteine 62
    • Matthews JR, Wakasugi N, Virelizier J-L, Yodoi J and Hay RT: Thioredoxin regulates the DNA binding activity of NF-kappaB by reduction of a disulphide bond involving cysteine 62. Nucl Acids Res 20: 3821-3830, 1992.
    • (1992) Nucl Acids Res , vol.20 , pp. 3821-3830
    • Matthews, J.R.1    Wakasugi, N.2    Virelizier, J.-L.3    Yodoi, J.4    Hay, R.T.5
  • 6
    • 0024421652 scopus 로고
    • Human transcription factor IIIC (TFIIIC). Purification, polypeptide structure, and the involvement of thiol groups in specific DNA binding
    • Cromlish JA and Roeder RG: Human transcription factor IIIC (TFIIIC). Purification, polypeptide structure, and the involvement of thiol groups in specific DNA binding. J Biol Chem 264: 18100-18109, 1989.
    • (1989) J Biol Chem , vol.264 , pp. 18100-18109
    • Cromlish, J.A.1    Roeder, R.G.2
  • 7
    • 0025887817 scopus 로고
    • In vitro DNA binding activity of Fos/Jun and BZLF1 but not C/EBP is affected by redox changes
    • Bannister AJ, Cook A and Kouzarides T: In vitro DNA binding activity of Fos/Jun and BZLF1 but not C/EBP is affected by redox changes. Oncogene 6: 1243-1250, 1991.
    • (1991) Oncogene , vol.6 , pp. 1243-1250
    • Bannister, A.J.1    Cook, A.2    Kouzarides, T.3
  • 8
    • 0021078605 scopus 로고
    • Evidence that the endogenous heat-stable glucocorticoid receptor-activating factor is thioredoxin
    • Grippo JF, Tienrungroj W, Dahmer MK, Housley PR and Pratt WB: Evidence that the endogenous heat-stable glucocorticoid receptor-activating factor is thioredoxin. J Biol Chem 258: 13658-13664, 1983. 16
    • (1983) J Biol Chem , vol.258 , pp. 13658-13664
    • Grippo, J.F.1    Tienrungroj, W.2    Dahmer, M.K.3    Housley, P.R.4    Pratt, W.B.5
  • 9
    • 0028818288 scopus 로고
    • Cell growth stimulation by the redox protein thioredoxin occurs by a novel helper mechanism
    • Gasdaska JR, Berggren M and Powis G: Cell growth stimulation by the redox protein thioredoxin occurs by a novel helper mechanism. Cell Growth Differ 6: 1643-1650, 1995.
    • (1995) Cell Growth Differ , vol.6 , pp. 1643-1650
    • Gasdaska, J.R.1    Berggren, M.2    Powis, G.3
  • 10
    • 0028304630 scopus 로고
    • Site-directed mutagenesis of active site cysteines in human thioredoxin produces competitive inhibitors of human thioredoxin reductase and elimination of mitogenic properties of thioredoxin
    • Oblong JE, Berggren M, Gasdaska PY and Powis G: Site-directed mutagenesis of active site cysteines in human thioredoxin produces competitive inhibitors of human thioredoxin reductase and elimination of mitogenic properties of thioredoxin. J Biol Chem 269: 11714-11720, 1994.
    • (1994) J Biol Chem , vol.269 , pp. 11714-11720
    • Oblong, J.E.1    Berggren, M.2    Gasdaska, P.Y.3    Powis, G.4
  • 11
    • 0026318680 scopus 로고
    • Coexpression of adult T-cell leukemia-derived factor, a human thioredoxin homologue, and human papillomavirus DNA in neoplastic cervical squamous epithelium
    • Fujii S, Nanbu Y, Nonogaki H, Konishi I, Mori T, Masutani H and Yodoi J: Coexpression of adult T-cell leukemia-derived factor, a human thioredoxin homologue, and human papillomavirus DNA in neoplastic cervical squamous epithelium. Cancer 68: 1583-1591, 1991.
    • (1991) Cancer , vol.68 , pp. 1583-1591
    • Fujii, S.1    Nanbu, Y.2    Nonogaki, H.3    Konishi, I.4    Mori, T.5    Masutani, H.6    Yodoi, J.7
  • 12
    • 0027991841 scopus 로고
    • The predicted amino acid sequence of human thioredoxin is identical to that of the autocrine growth factor human adult T-cell derived factor (ADF): Thioredoxin mRNA is elevated in some human tumors
    • Gasdaska PY, Oblong JE, Cotgreave IA and Powis G: The predicted amino acid sequence of human thioredoxin is identical to that of the autocrine growth factor human adult T-cell derived factor (ADF): Thioredoxin mRNA is elevated in some human tumors. Biochim Biophys Acta 1218: 292-296, 1994.
    • (1994) Biochim Biophys Acta , vol.1218 , pp. 292-296
    • Gasdaska, P.Y.1    Oblong, J.E.2    Cotgreave, I.A.3    Powis, G.4
  • 13
    • 0026563593 scopus 로고
    • Expression and growth-promoting effect of adult T-cell leukemia-derived factor. A human thioredoxin homologue in hepatocellular carcinoma
    • Nakamura H, Masutani H, Tagaya Y, Yamauchi A, Inamoto T, Nanbu Y, Fujii S, Ozawa K and Yodoi J: Expression and growth-promoting effect of adult T-cell leukemia-derived factor. A human thioredoxin homologue in hepatocellular carcinoma. Cancer 69: 2091-2097, 1992.
    • (1992) Cancer , vol.69 , pp. 2091-2097
    • Nakamura, H.1    Masutani, H.2    Tagaya, Y.3    Yamauchi, A.4    Inamoto, T.5    Nanbu, Y.6    Fujii, S.7    Ozawa, K.8    Yodoi, J.9
  • 14
    • 0030499036 scopus 로고    scopus 로고
    • Thioredoxin and thioredoxin reductase gene expression in human tumors and cell lines, and the effects of serum stimulation and hypoxia
    • Berggren M, Gallegos A, Gasdaska JR, Gasdaska PY, Warneke J and Powis G: Thioredoxin and thioredoxin reductase gene expression in human tumors and cell lines, and the effects of serum stimulation and hypoxia. Anticancer Res 16: 3459-3466, 1996.
    • (1996) Anticancer Res , vol.16 , pp. 3459-3466
    • Berggren, M.1    Gallegos, A.2    Gasdaska, J.R.3    Gasdaska, P.Y.4    Warneke, J.5    Powis, G.6
  • 15
    • 0030695172 scopus 로고    scopus 로고
    • Thioredoxin, a gene found over-expressed in human cancer, inhibitis apoptosis in vitro and in vivo
    • in press
    • Baker A, Briehl M, Payne C and Powis G: Thioredoxin, a gene found over-expressed in human cancer, inhibitis apoptosis in vitro and in vivo. Cancer Res 1997. (in press)
    • (1997) Cancer Res
    • Baker, A.1    Briehl, M.2    Payne, C.3    Powis, G.4
  • 16
    • 0029778527 scopus 로고    scopus 로고
    • Transfection with human thioredoxin increases cell proliferation and a dominant negative mutant thioredoxin reverses the transformed phenotype of breast cancer cells
    • Gallegos A, Gasdaska JR, Taylor CW, Paine-Murrieta GD, Goodman D, Gasdaska PY, Berggren M, Briehl MM and Powis G: Transfection with human thioredoxin increases cell proliferation and a dominant negative mutant thioredoxin reverses the transformed phenotype of breast cancer cells. Cancer Res 56: 5765-5770, 1996.
    • (1996) Cancer Res , vol.56 , pp. 5765-5770
    • Gallegos, A.1    Gasdaska, J.R.2    Taylor, C.W.3    Paine-Murrieta, G.D.4    Goodman, D.5    Gasdaska, P.Y.6    Berggren, M.7    Briehl, M.M.8    Powis, G.9
  • 19
    • 0029114721 scopus 로고
    • Molecular actions of Ebselen - An antiinflammatory antioxidant
    • Schewe T: Molecular actions of Ebselen - an antiinflammatory antioxidant. Gen Pharrnac 26: 1153-1169, 1995.
    • (1995) Gen Pharrnac , vol.26 , pp. 1153-1169
    • Schewe, T.1
  • 21
    • 0026694318 scopus 로고
    • Selenite is a substrate for calf thymus thioredoxin reductase and thioredoxin and elicits a large non-stoichiometric oxidation of NADPH in the presence of oxygen
    • Kumar S, Bjornstedt M and Holmgren A: Selenite is a substrate for calf thymus thioredoxin reductase and thioredoxin and elicits a large non-stoichiometric oxidation of NADPH in the presence of oxygen. Eur J Biochem 207: 435-439, 1992.
    • (1992) Eur J Biochem , vol.207 , pp. 435-439
    • Kumar, S.1    Bjornstedt, M.2    Holmgren, A.3
  • 22
    • 0024412233 scopus 로고
    • Expedient synthesis of Ebselen and related compounds
    • Engman L and Hallberg A: Expedient synthesis of Ebselen and related compounds. J Org Chem 51: 2964-2966, 1989.
    • (1989) J Org Chem , vol.51 , pp. 2964-2966
    • Engman, L.1    Hallberg, A.2
  • 23
    • 0028215547 scopus 로고
    • Evidence for a common selenolate intermediate in the glutathione peroxidase-like catalysis of α-(phenylselenenyl) ketones and diphenyl diselenide
    • Engman L, Andersson C, Morgenstern R, Cotgreave IA, Andersson CM and Hallberg A: Evidence for a common selenolate intermediate in the glutathione peroxidase-like catalysis of α-(phenylselenenyl) ketones and diphenyl diselenide. Tetrahedron 50: 2929-2938, 1994.
    • (1994) Tetrahedron , vol.50 , pp. 2929-2938
    • Engman, L.1    Andersson, C.2    Morgenstern, R.3    Cotgreave, I.A.4    Andersson, C.M.5    Hallberg, A.6
  • 24
    • 0026640860 scopus 로고
    • Characterization and quantitation of a selenol intermediate in the reaction of Ebselen with thiols
    • Cotgreave IA, Morgenstern R, Engman L and Ahokas J: Characterization and quantitation of a selenol intermediate in the reaction of Ebselen with thiols. Chem-Biol Interact 84: 69-76, 1992.
    • (1992) Chem-Biol Interact , vol.84 , pp. 69-76
    • Cotgreave, I.A.1    Morgenstern, R.2    Engman, L.3    Ahokas, J.4
  • 25
    • 0027055267 scopus 로고
    • Thiol peroxidase activity of diaryl ditellurides as determined by a 1H NMR method
    • Engman L, Stern D, Cotgreave IA and Andersson CM: Thiol peroxidase activity of diaryl ditellurides as determined by a 1H NMR method. J Am Chem Soc 114: 9737-9743, 1992.
    • (1992) J Am Chem Soc , vol.114 , pp. 9737-9743
    • Engman, L.1    Stern, D.2    Cotgreave, I.A.3    Andersson, C.M.4
  • 26
    • 0001310615 scopus 로고
    • Synthesis of IV-metylphenotellurazine
    • Bergman J and Engman L: Synthesis of IV-metylphenotellurazine. J Organomet Chem 257: 223-225, 1983.
    • (1983) J Organomet Chem , vol.257 , pp. 223-225
    • Bergman, J.1    Engman, L.2
  • 27
    • 37049067682 scopus 로고
    • New alkoxylated dibenzo[1,4]dichalcogenines as donors for low-dimensional materials: Electrochemistry and cation-radical salts
    • Engman L, Hellberg J and Ishag C: New alkoxylated dibenzo[1,4]dichalcogenines as donors for low-dimensional materials: Electrochemistry and cation-radical salts. J Chem Soc Perkins Trans 1: 2095-2101, 1988.
    • (1988) J Chem Soc Perkins Trans , vol.1 , pp. 2095-2101
    • Engman, L.1    Hellberg, J.2    Ishag, C.3
  • 28
    • 37049075551 scopus 로고
    • Application of the Hammett equation tot he electrochemical oxidation of diaryl chalcogenides and aryl methyl chalcogenides
    • Engman L, Persson J, Andersson CM and Berglund M: Application of the Hammett equation tot he electrochemical oxidation of diaryl chalcogenides and aryl methyl chalcogenides. J Chem Soc Perkins Trans I: 1309-1313, 1992.
    • (1992) J Chem Soc Perkins Trans , vol.1 , pp. 1309-1313
    • Engman, L.1    Persson, J.2    Andersson, C.M.3    Berglund, M.4
  • 29
    • 0029085043 scopus 로고
    • Catalytic antioxidant activity of diaryl tellurides in a two-phase lipid peroxidation model
    • Vessman K, Ekstrom M, Berglund M, Andersson CM and Engman L: Catalytic antioxidant activity of diaryl tellurides in a two-phase lipid peroxidation model. J Org Chem 60: 4461-4467, 1995.
    • (1995) J Org Chem , vol.60 , pp. 4461-4467
    • Vessman, K.1    Ekstrom, M.2    Berglund, M.3    Andersson, C.M.4    Engman, L.5
  • 30
    • 0001385932 scopus 로고
    • Complexes of anilines with tellurium tetrachloride. Synthesis of amino-substituted diphenyl tellurides
    • Engman L and Persson J: Complexes of anilines with tellurium tetrachloride. Synthesis of amino-substituted diphenyl tellurides. Organometal 12: 1068-1072, 1993.
    • (1993) Organometal , vol.12 , pp. 1068-1072
    • Engman, L.1    Persson, J.2
  • 31
    • 33845549940 scopus 로고
    • New general synthesis of diaryl tellurides from aromatic amines
    • Engman L: New general synthesis of diaryl tellurides from aromatic amines. J Org Chem 18: 2920-2922, 1983.
    • (1983) J Org Chem , vol.18 , pp. 2920-2922
    • Engman, L.1
  • 33
    • 0001224915 scopus 로고
    • Thiol peroxidase activity of diorganyl tellurides
    • Engman L, Stern D and Pelcman M: Thiol peroxidase activity of diorganyl tellurides. J Org Chem 59: 1973-1979, 1994.
    • (1994) J Org Chem , vol.59 , pp. 1973-1979
    • Engman, L.1    Stern, D.2    Pelcman, M.3
  • 34
    • 0001608132 scopus 로고
    • Synthesis of 2,5-dihydrotellurophene - A new heterocyclic compound
    • Bergman J and Engman L: Synthesis of 2,5-dihydrotellurophene - a new heterocyclic compound. J Am Chem Soc 103: 2715-2718, 1981.
    • (1981) J Am Chem Soc , vol.103 , pp. 2715-2718
    • Bergman, J.1    Engman, L.2
  • 35
    • 0001406450 scopus 로고
    • Tellurium in organic chemistry I. A novel synthesis of biaryls
    • Bergman J: Tellurium in organic chemistry I. A novel synthesis of biaryls. Tetrahedron 28: 3323-3331, 1972.
    • (1972) Tetrahedron , vol.28 , pp. 3323-3331
    • Bergman, J.1
  • 36
    • 0027186030 scopus 로고
    • Purification of human thioredoxin reductase: Properties and characterization by absorption and circular dichroism spectroscopy
    • Oblong JE, Gasdaska PY, Sherrill K and Powis G: Purification of human thioredoxin reductase: Properties and characterization by absorption and circular dichroism spectroscopy. Biochem 32: 7271-7277, 1993.
    • (1993) Biochem , vol.32 , pp. 7271-7277
    • Oblong, J.E.1    Gasdaska, P.Y.2    Sherrill, K.3    Powis, G.4
  • 37
    • 0011247498 scopus 로고
    • On the role of flavin adenine dinucleotide and thiol growth in the catalytic mechanism of yeast glutathione reductase
    • Colmon RF and Black S: On the role of flavin adenine dinucleotide and thiol growth in the catalytic mechanism of yeast glutathione reductase. JBiol Chem 240: 1796-1803, 1965.
    • (1965) JBiol Chem , vol.240 , pp. 1796-1803
    • Colmon, R.F.1    Black, S.2
  • 38
    • 0017760360 scopus 로고
    • Glutathione reductase from human erythrocytes - Isolation of the enzyme and sequence analysis of the redox-active peptide
    • Krohne-Ehrich G, Schirrner RH and Untucht-Grau R: Glutathione reductase from human erythrocytes - Isolation of the enzyme and sequence analysis of the redox-active peptide. Eur J Biochem 80: 65-71, 1971.
    • (1971) Eur J Biochem , vol.80 , pp. 65-71
    • Krohne-Ehrich, G.1    Schirrner, R.H.2    Untucht-Grau, R.3
  • 39
    • 0017184389 scopus 로고
    • A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding
    • Bradford M: A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72: 248-254, 1976.
    • (1976) Anal Biochem , vol.72 , pp. 248-254
    • Bradford, M.1
  • 40
    • 0021967405 scopus 로고
    • Measurement of human tumor cell growth in soft-agar cultures using computer assisted volume analysis
    • Alley MC and Lieber MM: Measurement of human tumor cell growth in soft-agar cultures using computer assisted volume analysis. Br J Cancer 52: 205-224, 1985.
    • (1985) Br J Cancer , vol.52 , pp. 205-224
    • Alley, M.C.1    Lieber, M.M.2
  • 42
    • 0002265018 scopus 로고
    • Protocols for screening chemical agents and natural products against animal tumors and other biological systems
    • Geran RI, Greenberg NH, Macdonald MM, Schumacher AM and Abbott BJ: Protocols for screening chemical agents and natural products against animal tumors and other biological systems. Cancer Chemother Rep 3: 1-103, 1972.
    • (1972) Cancer Chemother Rep , vol.3 , pp. 1-103
    • Geran, R.I.1    Greenberg, N.H.2    Macdonald, M.M.3    Schumacher, A.M.4    Abbott, B.J.5
  • 43
    • 0025062053 scopus 로고
    • The mechanism of action of the nitrosoureas anti-tumor drugs on thioredoxin reductase, glutathione reductase and ribonucleotide reductase
    • Schallreuter KU, Gleason FK and Wood JM: The mechanism of action of the nitrosoureas anti-tumor drugs on thioredoxin reductase, glutathione reductase and ribonucleotide reductase. Biochim Biophys Acta 1051: 14-20, 1990.
    • (1990) Biochim Biophys Acta , vol.1051 , pp. 14-20
    • Schallreuter, K.U.1    Gleason, F.K.2    Wood, J.M.3
  • 44
    • 0023264825 scopus 로고
    • Azelaic acid as a competitive inhibitor of thioredoxin reductase in human melanoma cells
    • Schallreuter KU and Wood JM: Azelaic acid as a competitive inhibitor of thioredoxin reductase in human melanoma cells. Cancer Lett 36: 297-305, 1987.
    • (1987) Cancer Lett , vol.36 , pp. 297-305
    • Schallreuter, K.U.1    Wood, J.M.2
  • 45
    • 0024314622 scopus 로고
    • The stereospecific suicide inhibition of human meianoma thioredoxin reductase by 13-cis-retinoic acid
    • Schallreuter KU and Wood JM: The stereospecific suicide inhibition of human meianoma thioredoxin reductase by 13-cis-retinoic acid. Biochem Biophys Res Commun 160: 573-579, 1989.
    • (1989) Biochem Biophys Res Commun , vol.160 , pp. 573-579
    • Schallreuter, K.U.1    Wood, J.M.2
  • 46
    • 0026571917 scopus 로고
    • Mechanism-based inhibition of thioredoxin reductase by antitumor quinoid compounds
    • Mau B and Powis G: Mechanism-based inhibition of thioredoxin reductase by antitumor quinoid compounds. BiochemPharmacol 43: 1613-1620, 1992.
    • (1992) BiochemPharmacol , vol.43 , pp. 1613-1620
    • Mau, B.1    Powis, G.2
  • 47
    • 0025914415 scopus 로고
    • The correlation of the oxidation potentials of structurally related dibenzo[1,4] dichalcogenines to their antioxidance capacity in biological systems undergoing free radical-induced lipid peroxidation
    • Cotgreave IA, Moldeus P, Engman L and Hallbeg A: The correlation of the oxidation potentials of structurally related dibenzo[1,4] dichalcogenines to their antioxidance capacity in biological systems undergoing free radical-induced lipid peroxidation. Biochem Pharmacol 12: 1481-1485, 1991.
    • (1991) Biochem Pharmacol , vol.12 , pp. 1481-1485
    • Cotgreave, I.A.1    Moldeus, P.2    Engman, L.3    Hallbeg, A.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.