메뉴 건너뛰기




Volumn 53, Issue 10, 1997, Pages 1435-1444

Dihydro-1,4-benzothiazine-6,7-dione, the ultimate toxic metabolite of 4- S-Cysteaminylphenol and 4-S-Cysteaminylcatechol

Author keywords

Catechol; Cytotoxicity; Melanocyte; Melanoma; Phenol; Tyrosinase

Indexed keywords

4 S CYSTEAMINYLPHENOL; ALCOHOL DEHYDROGENASE; CATECHOL; GLUTATHIONE; PHENOL DERIVATIVE; TYROSINE DERIVATIVE;

EID: 0030737929     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-2952(97)00075-0     Document Type: Article
Times cited : (42)

References (29)
  • 2
    • 0028003828 scopus 로고
    • Melanogenesis as a targeting strategy against metastatic melanoma: A reassessment
    • Prota G, d'Ischia M and Mascagna D, Melanogenesis as a targeting strategy against metastatic melanoma: A reassessment. Melanoma Res 4: 351-358, 1994.
    • (1994) Melanoma Res , vol.4 , pp. 351-358
    • Prota, G.1    D'Ischia, M.2    Mascagna, D.3
  • 3
    • 0014470003 scopus 로고
    • Hydroxyanisole depigmentation: In vitro studies
    • Riley PA, Hydroxyanisole depigmentation: In vitro studies. J Pathol 97: 193-206, 1969.
    • (1969) J Pathol , vol.97 , pp. 193-206
    • Riley, P.A.1
  • 5
    • 0027981415 scopus 로고
    • Biomimetic oxidation of the antimelanoma agent 4-S-cysteaminylphenol and related catechol thioethers: Isolation and reaction behaviour of novel dihydrobenzothiazinequinones
    • Mascagna D, Costantini C, d'Ischia M and Prota G, Biomimetic oxidation of the antimelanoma agent 4-S-cysteaminylphenol and related catechol thioethers: Isolation and reaction behaviour of novel dihydrobenzothiazinequinones. Tetrahedron 50: 8757-8764, 1994.
    • (1994) Tetrahedron , vol.50 , pp. 8757-8764
    • Mascagna, D.1    Costantini, C.2    D'Ischia, M.3    Prota, G.4
  • 6
    • 0023222508 scopus 로고
    • Mechanism of selective toxicity of 4-S-cysteinylphenol and 4-S-cysteaminylphenol to melanocytes
    • Ito S, Kato T, Ishikawa K, Kasuga T and Jimbow K, Mechanism of selective toxicity of 4-S-cysteinylphenol and 4-S-cysteaminylphenol to melanocytes. Biochem Pharmacol 36: 2007-2011, 1987.
    • (1987) Biochem Pharmacol , vol.36 , pp. 2007-2011
    • Ito, S.1    Kato, T.2    Ishikawa, K.3    Kasuga, T.4    Jimbow, K.5
  • 7
    • 0025963402 scopus 로고
    • The killing effect of 4-S-cysteaminylphenol, a newly synthesized melanin precursor, on B16 melanoma cell lines
    • Yamada I, Seki S, Ito S, Suzuki S, Matsubara O and Kasuga T, The killing effect of 4-S-cysteaminylphenol, a newly synthesized melanin precursor, on B16 melanoma cell lines. Br J Cancer 63: 187-190, 1991.
    • (1991) Br J Cancer , vol.63 , pp. 187-190
    • Yamada, I.1    Seki, S.2    Ito, S.3    Suzuki, S.4    Matsubara, O.5    Kasuga, T.6
  • 8
    • 0027204905 scopus 로고
    • In vivo antimelanoma effects of 4-S-cysteaminylphenol, a newly synthesized therapeutic agent specific to melanoma
    • Kitagawa M, Nemoto T, Seki S, Ito S and Kasuga T, In vivo antimelanoma effects of 4-S-cysteaminylphenol, a newly synthesized therapeutic agent specific to melanoma. J Cancer Res Clin Oncol 119: 470-474, 1993.
    • (1993) J Cancer Res Clin Oncol , vol.119 , pp. 470-474
    • Kitagawa, M.1    Nemoto, T.2    Seki, S.3    Ito, S.4    Kasuga, T.5
  • 9
    • 0025223134 scopus 로고
    • The in vivo antimelanoma effect of 4-S-cysteaminylphenol and its N-acetyl derivative
    • Miura S, Jimbow K and Ito S, The in vivo antimelanoma effect of 4-S-cysteaminylphenol and its N-acetyl derivative. Int J Cancer 46: 931-934, 1990.
    • (1990) Int J Cancer , vol.46 , pp. 931-934
    • Miura, S.1    Jimbow, K.2    Ito, S.3
  • 10
    • 0025339155 scopus 로고
    • Melanocytotoxicity and antimelanoma effects of phenolic amine compounds in mice in vivo
    • Alena F, Jimbow K and Ito S, Melanocytotoxicity and antimelanoma effects of phenolic amine compounds in mice in vivo. Cancer Res 50: 3743-3747, 1990.
    • (1990) Cancer Res , vol.50 , pp. 3743-3747
    • Alena, F.1    Jimbow, K.2    Ito, S.3
  • 11
    • 0023888861 scopus 로고
    • Demonstration of the potent antihypertensive activity of phenyl-2-aminoethyl sulfides
    • Herman HH, Pollock SH, Fowler LC and May SW, Demonstration of the potent antihypertensive activity of phenyl-2-aminoethyl sulfides. J Cardiovasc Pharmacol 11: 501-510, 1988.
    • (1988) J Cardiovasc Pharmacol , vol.11 , pp. 501-510
    • Herman, H.H.1    Pollock, S.H.2    Fowler, L.C.3    May, S.W.4
  • 12
    • 0025327397 scopus 로고
    • Mechanism of growth inhibition of melanoma cells by 4-S-cysteaminylphenol and its analogues
    • Inoue S, Ito S, Wakamatsu K, Jimbow K and Fujita K, Mechanism of growth inhibition of melanoma cells by 4-S-cysteaminylphenol and its analogues. Biochem Pharmacol 39: 1077-1083, 1990.
    • (1990) Biochem Pharmacol , vol.39 , pp. 1077-1083
    • Inoue, S.1    Ito, S.2    Wakamatsu, K.3    Jimbow, K.4    Fujita, K.5
  • 14
    • 0021150070 scopus 로고
    • Antihypertensive activities of phenyl aminoethyl sulfides: A class of synthetic substrates for dopamine β-hydroxylase
    • Padgette SR, Herman HH, Han JH, Pollock SH and May SW, Antihypertensive activities of phenyl aminoethyl sulfides: A class of synthetic substrates for dopamine β-hydroxylase. J Med Chem 27: 1354-1357, 1984.
    • (1984) J Med Chem , vol.27 , pp. 1354-1357
    • Padgette, S.R.1    Herman, H.H.2    Han, J.H.3    Pollock, S.H.4    May, S.W.5
  • 15
    • 0023665030 scopus 로고
    • Determination of natural thiols by liquid chromatography after derivatization with 3,5-di-tertbutyl-1,2-benzoquinone
    • Imai Y, Ito S and Fujita K, Determination of natural thiols by liquid chromatography after derivatization with 3,5-di-tertbutyl-1,2-benzoquinone. J Chromatogr 420: 404-410, 1987.
    • (1987) J Chromatogr , vol.420 , pp. 404-410
    • Imai, Y.1    Ito, S.2    Fujita, K.3
  • 16
    • 0014449795 scopus 로고
    • Fluorimetric assay of enzymes
    • Ed. Glick D, Interscience Publishers, New York
    • Roth M, Fluorimetric assay of enzymes. In: Methods in Biochemical Analysis (Ed. Glick D), pp. 189-285. Interscience Publishers, New York, 1969.
    • (1969) Methods in Biochemical Analysis , pp. 189-285
    • Roth, M.1
  • 17
    • 0027476649 scopus 로고
    • Reactivity of orthoquinones involved in tyrosinase-dependent cytotoxicity: Differences between alkylthio- and alkoxy-substituents
    • Cooksey CJ, Jimbow K, Land EJ and Riley PA, Reactivity of orthoquinones involved in tyrosinase-dependent cytotoxicity: Differences between alkylthio- and alkoxy-substituents. Melanoma Res 2: 283-293, 1992.
    • (1992) Melanoma Res , vol.2 , pp. 283-293
    • Cooksey, C.J.1    Jimbow, K.2    Land, E.J.3    Riley, P.A.4
  • 18
    • 0020440741 scopus 로고
    • +]-ATPase of Neurospora crassa by N-ethylmaleimide. Protection by nucleotides
    • +]-ATPase of Neurospora crassa by N-ethylmaleimide. Protection by nucleotides. J Biol Chem 257: 12051-12055, 1982.
    • (1982) J Biol Chem , vol.257 , pp. 12051-12055
    • Brooker, R.J.1    Slayman, C.W.2
  • 19
    • 0043193607 scopus 로고
    • In vitro studies of 2,4-dihydroxyphenylalanine, a prodrug targeted against malignant melanoma cells
    • Morrison ME, Yagi M and Cohen G, In vitro studies of 2,4-dihydroxyphenylalanine, a prodrug targeted against malignant melanoma cells. Proc Natl Acad Sci USA 82: 2960-2964, 1985.
    • (1985) Proc Natl Acad Sci USA , vol.82 , pp. 2960-2964
    • Morrison, M.E.1    Yagi, M.2    Cohen, G.3
  • 20
    • 0028956822 scopus 로고
    • Tyrosinase-mediated cytotoxicity of 4-substituted phenols: Quantitative structure-thiol-reactivity relationships of the derived o-quinones
    • Cooksey CJ, Land EJ, Ramsden CA and Riley PA, Tyrosinase-mediated cytotoxicity of 4-substituted phenols: Quantitative structure-thiol-reactivity relationships of the derived o-quinones. Anticancer Drug Des 10: 119-129, 1995.
    • (1995) Anticancer Drug Des , vol.10 , pp. 119-129
    • Cooksey, C.J.1    Land, E.J.2    Ramsden, C.A.3    Riley, P.A.4
  • 21
    • 0026772939 scopus 로고
    • Thymidylate synthase as a target enzyme for the melanoma-specific toxocity of 4-s-cysteaminylphenol and N-acetyl-4-S-cysteaminylphenol
    • Prezioso JA, Wang N and Bloomer WD, Thymidylate synthase as a target enzyme for the melanoma-specific toxocity of 4-S-cysteaminylphenol and N-acetyl-4-S-cysteaminylphenol. Cancer Chemother Pharmacol 30: 394-400, 1992.
    • (1992) Cancer Chemother Pharmacol , vol.30 , pp. 394-400
    • Prezioso, J.A.1    Wang, N.2    Bloomer, W.D.3
  • 22
    • 0028227817 scopus 로고
    • Selective in vivo accumulation of N-acetyl-4-S-cysteaminylphenol in B16F10 murine melanoma and enhancement of its in vitro and in vivo antimelanoma effect by combination of buthionine sulfoximine
    • Alena F, Iwashina T, Gili A and Jimbow K, Selective in vivo accumulation of N-acetyl-4-S-cysteaminylphenol in B16F10 murine melanoma and enhancement of its in vitro and in vivo antimelanoma effect by combination of buthionine sulfoximine. Cancer Res 54: 2661-2666, 1994.
    • (1994) Cancer Res , vol.54 , pp. 2661-2666
    • Alena, F.1    Iwashina, T.2    Gili, A.3    Jimbow, K.4
  • 23
    • 0018666729 scopus 로고
    • Potent and specific inhibition of glutathione synthesis by buthionine sulfoximine (S-n-butyl homocysteine sulfoximine)
    • Griffith OW and Meister A, Potent and specific inhibition of glutathione synthesis by buthionine sulfoximine (S-n-butyl homocysteine sulfoximine). J Biol Chem 254: 7558-7560, 1979.
    • (1979) J Biol Chem , vol.254 , pp. 7558-7560
    • Griffith, O.W.1    Meister, A.2
  • 24
    • 0029077703 scopus 로고
    • Glutathione plays a key role in the depigmenting and melanocytotoxic action of N-acetyl-4-S-cysteaminylphenol in black and yellow hair follicles
    • Alena F, Dixon W, Thomas P and Jimbow K, Glutathione plays a key role in the depigmenting and melanocytotoxic action of N-acetyl-4-S-cysteaminylphenol in black and yellow hair follicles. J Invest Dermatol 104: 792-797, 1995.
    • (1995) J Invest Dermatol , vol.104 , pp. 792-797
    • Alena, F.1    Dixon, W.2    Thomas, P.3    Jimbow, K.4
  • 25
    • 0027049415 scopus 로고
    • Glutathione depletion in mouse melanoma cells increases their sensitivity to oxidative lysis
    • Peinado P, Martinez-Liarte JH, del Marmol V, Solano F and Lozano JA, Glutathione depletion in mouse melanoma cells increases their sensitivity to oxidative lysis. Cancer J 5: 348-353, 1992.
    • (1992) Cancer J , vol.5 , pp. 348-353
    • Peinado, P.1    Martinez-Liarte, J.H.2    Del Marmol, V.3    Solano, F.4    Lozano, J.A.5
  • 27
    • 0018148688 scopus 로고
    • Autoxidation versus covalent binding of quinones as the mechanism of toxicity of dopamine, 6-hydroxydopamine, and related compounds toward C1300 neuroblastoma cells in vitro
    • Graham DG, Tiffany SM, Bell WR Jr and Gutknecht WF, Autoxidation versus covalent binding of quinones as the mechanism of toxicity of dopamine, 6-hydroxydopamine, and related compounds toward C1300 neuroblastoma cells in vitro. Mol Pharmacol 14: 644-653, 1978.
    • (1978) Mol Pharmacol , vol.14 , pp. 644-653
    • Graham, D.G.1    Tiffany, S.M.2    Bell W.R., Jr.3    Gutknecht, W.F.4
  • 28
    • 0020073933 scopus 로고
    • Participation of active oxygen species in 6-hydroxydopamine toxicity to a human neuroblastoma cell line
    • Tiffany-Castiglioni E, Saneto RP, Proctor PH and Perez-Polo JR, Participation of active oxygen species in 6-hydroxydopamine toxicity to a human neuroblastoma cell line. Biochem Pharmacol 31: 181-188, 1981.
    • (1981) Biochem Pharmacol , vol.31 , pp. 181-188
    • Tiffany-Castiglioni, E.1    Saneto, R.P.2    Proctor, P.H.3    Perez-Polo, J.R.4
  • 29
    • 0015839371 scopus 로고
    • 6-Hydroxydopamine: Evidence for superoxide radical as an oxidative intermediate
    • Heikkila RE and Cohen G, 6-Hydroxydopamine: Evidence for superoxide radical as an oxidative intermediate. Science 181: 456-457, 1973.
    • (1973) Science , vol.181 , pp. 456-457
    • Heikkila, R.E.1    Cohen, G.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.