Comparison of antimelanoma effects of 4-S-cysteaminylphenol and its homologues

Melanoma Research

Volumn 8, Issue 2, 1998, Pages 105-112

  Inoue, S ^a   Hasegawa, K ^a   Wakamatsu, K ^a   Ito, S ^a  

^a FUJITA HEALTH UNIVERSITY   (Japan)

Author keywords

Antimelanoma agent; Melanoma; Phenols; Tyrosinase

Indexed keywords

4 S CYSTEAMINYLPHENOL; 4 S HOMOCYSTEAMINYLPHENOL; ALPHA METHYL 4 S CYSTEAMINYLPHENOL; PHENOL DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CHEMOTHERAPY; CONTROLLED STUDY; CYTOTOXICITY; INTRATUMORAL DRUG ADMINISTRATION; MELANOMA; MOUSE; NONHUMAN; PRIORITY JOURNAL;

EID: 0031897125     PISSN: 09608931     EISSN: None     Source Type: Journal    
DOI: 10.1097/00008390-199804000-00002     Document Type: Article

References (25)

1. Prota G, d'Ischia M, Mascagna D. Melanogenesis as a targeting strategy against metastatic melanoma: a reassessment. Melanoma Res 1994; 4: 351-358.
2. Prota G. Melanins and Melanogenesis. New York: Academic Press, 1992: 290.
3. Cooksey CJ, Land EJ, Ramsden CA, et al. Tyrosinasemediated cytotoxicity of 4-substituted phenols: quantitative structure-thiol-reactivity relationships of the derived o-quinones. Anticancer Drug Design 1995; 10: 119-129.
4. Ito S, Kato T, Ishikawa K, et al. Mechanism of selective toxicity of 4-S-cysteinyrphenol and 4-S-cysteaminylphenol to melanocytes. Biochem Pharmacol 1987; 36: 2007-2011.
5. Prezioso JA, Wang N, Bloomer WD. Thymidylate synthase as a target enzyme for the melanoma-specific toxicity of 4-S-cysteaminylphenol and N-acetyl-4-5-cysteaminylphenol. Cancer Chemother Pharmacol 1992; 30: 394-400.
6. Yamada I, Seki S, Ito S, et al. The killing effect of 4-S-cysteaminylphenol a newly synthesized melanin precursor, on B16 melanoma cell lines. Br J Cancer 1991; 63: 187-190.
7. Kitagawa M, Nemoto T, Seki S, et al. In vivo antimelanoma effects of 4-S-cysteaminylphenol, a newly synthesized therapeutic agent specific to melanoma. J Cancer Res Clin Oncol 1993; 119: 470-474
8. Miura S, Jimbow K, Ito S. The in vivo antimelanoma effect of 4-S-cysteaminylphenol and its N-acetyl derivative. Int J Cancer 1990; 46: 931-934.
9. Alena F, Jimbow K, Ito S. Melanocytotoxicity and antimelanoma effects of phenolic amine compounds in mice in vivo. Cancer Res 1990; 50: 3743-3747.
10. Mascagna D, Costantini C, d'Ischia M, et al. Biomimetic oxidation of the antimelanoma agent 4-S-cysteaminylphenol and related catechol thioethers: isolation and reaction behaviour of novel dihydrobenzothiazine-quinones. Tetrahedron 1994; 50: 8757-8764.
11. Hasegawa K, Ito S, Inoue S, et al. Dihydro-1,4-benzothiazine-6,7-dione, the ultimate toxic metabolite of 4-S-cysteaminylphenol and 4-S-cysteaminylcatechol. Biochem Pharmacol 1997; 53: 1433-1444.
12. Herman HH, Pollock SH, Fowler LC, et al. Demonstration of the potent antihypertensive activity of phenyl-2-aminoethyl sulfides. J Cardiovasc Pharmacol 1988; 11: 501-510.
13. Inoue S, Ito S, Wakamatsu K, et al. Mechanism of growth inhibition of melanoma cells by 4-S-cysteaminylphenol and its analogues. Biochem Pharmacol 1990; 39: 1077-1083.
14. Padgette SR, Herman HH, Han JH, et al. Antihypertensive activities of phenyl aminoethyl sulfides: a class of synthetic substrates for dopamine β-hydroxylase. J Med Chem 1984; 27: 1354-1357.
15. Imai Y, Ito S, Fujita K. Determination of natural thiols by liquid chromatography after derivatization with 3,5-di-tert-butyl-1,2-benzoquinone. J Chromatogr 1987; 420: 404-410.
16. Ito S, Fujita K. Microanalysis of eumelanin and pheomelanin in hair and melanomas by chemical degradation and liquid chromatography. Anal Biochem 1985; 144: 527-536.
17. Roth M. Fluorimetric assay of enzymes. In: Glick D, ed. Methods in Biochemical Analysis. New York: Interscience Publishers, 1969: 189-285.
18. Zhao H, Boissy RE. Distinguishing between the catalytic potential and apparent expression of tyrosinase activities. Am J Med Sci 1994; 308: 322-330.
19. Solca FF, Chluba-de Tapia J, Iwata K, et al. B16-G4F mouse melanoma cells: an MSH receptor-deficient cell clone. FEBS Lett 1993; 322: 177-180.
20. Ozeki H, Ito S, Wakamatsu K, et al. Chemical characterization of hair melanins in various coat-color mutants of mice. J Invest Dermatol 1995; 105: 361-366.
21. Pancovich JM, Jimbow K, Ito S. 4-S-Cysteaminylphenol and its analogues as substrates for tyrosinase and monoamine oxidase. Pigment Cell Res 1990; 3: 146-149.
22. Kachi T, Iwase S, Mano T, et al. Effect of L-threo-3,4-dihydroxyphenylserine on muscle sympathetic nerve activities in Shy-Drager syndrome. Neurology 1988; 38: 1091-1094.
23. Levine N, Sheftel SN, Eytan T, et al. Induction of skin tanning by subcutaneous administration of a potent synthetic analogue of melanotropin. JAMA 1991; 266: 2730-2376.
24. Alena F, Iwashina T, Gili A, et al. 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 1994; 54: 2661-2666.
25. Herman HH, Husain PA, Colbert JE, et al. The enantiomeric specificity of the antihypertensive activity of 1-(phenylthio)-2-aminopropane, a synthetic substrate analogue for dopamine β-monooxygenase. J Med Chem 1991; 34: 1082-1085.