Synthesis and selective in vitro anti-melanoma effect of enantiomeric α-methyl- and α-ethyl-4-S-cysteaminylphenol

Melanoma Research

Volumn 13, Issue 6, 2003, Pages 603-609

  Yukitake, Jun ^a   Otake, Hiromi ^a   Inoue, Shigeki ^a   Wakamatsu, Kazumasa ^a   Olivares, Concepción ^b   Solano, Francisco ^b   Hasegawa, Katsutoshi ^a   Ito, Shosuke ^a  

^a FUJITA HEALTH UNIVERSITY   (Japan)

^b UNIVERSITY OF MURCIA   (Spain)

Author keywords

4 S cysteaminylphenol; Enantiomer; Melanogenesis; Melanoma; Tyrosinase

Indexed keywords

2 AMINOBUTANOL; 4 S CYSTEAMINYLPHENOL; ACETYLCYSTEINE; ALPHA ETHYL 4 S CYSTEAMINYLPHENOL; ALPHA METHYL 4 S CYSTEAMINYLPHENOL; AMINOPROPANOL; ANTINEOPLASTIC AGENT; GLUTATHIONE; OXAZOLINE DERIVATIVE; PHENOL DERIVATIVE; PHENYLTHIOUREA; PROPANOL; PROTEIN P60; PROTEIN P70; UNCLASSIFIED DRUG;

ARTICLE; CELL STRAIN 3T3; CONTROLLED STUDY; CORRELATION ANALYSIS; CYTOTOXICITY; DEPLETION; DRUG EFFECT; DRUG SELECTIVITY; DRUG SYNTHESIS; ENANTIOMER; FIBROBLAST; HUMAN; IN VITRO STUDY; MELANOMA; MELANOMA B16; MELANOMA CELL; PRIORITY JOURNAL;

3T3 CELLS; ACETYLCYSTEINE; ANIMALS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CYSTEAMINE; GLUTATHIONE; INHIBITORY CONCENTRATION 50; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; MELANOMA; MELANOMA, EXPERIMENTAL; MICE; MODELS, CHEMICAL; MONOPHENOL MONOOXYGENASE; PHENOLS; STEREOISOMERISM; TIME FACTORS; TYROSINE;

EID: 1542330125     PISSN: 09608931     EISSN: None     Source Type: Journal    
DOI: 10.1097/00008390-200312000-00010     Document Type: Article

References (27)

1. Prota G. Melanins and Melanogenesis. New York: Academic Press; 1992.
2. Prota G, d'Ischia M, Mascagna D. Melanogenesis as a targeting strategy against metastatic melanoma: a reassessment. Melanoma Res 1994; 4:351-358.
3. Riley PA, Cooksey CJ, Johnson CI, Land EJ, Latter AM, Ramsden CA. Melanogenesis-targeted anti-melanoma pro-drug development: effect of side-chain variations on cytotoxicity of tyrosinase-generated orthoquinones in a model screening system. Eur J Cancer 1997; 33: 135-143.
4. Ito S, Kato T, Ishikawa K, Kasuga T, Jimbow K. Mechanism of selective toxicity of 4-S-cysteinylphenol and 4-S-cysteaminylphenol to melanocytes. Biochem Pharmacol 1987; 36:2007-2011.
5. Mascagna D, Costantini C, d'Ischia M, Prota G. Biomimetic oxidation of the antimelanoma agent 4-S-cysteaminylphenol and related catechol thioethers: isolation and reaction behaviour of novel dihydrobenzothiazinequinones. Tetrahedron 1994; 50:8757-8764.
6. Hasegawa K, Ito S, Inoue S, Wakamatsu K, Ozeki H, Ishiguro I. Dihydro-1,4-benzothiazine-6,7-dione, the ultimate toxic metabolite of 4-S-cysteaminylphenol and 4-S-cysteaminylcatechol. Biochem Pharmacol 1997; 53:1435-1444.
7. Inoue S, Hasegawa K, Wakamatsu K, Ito S. Comparison of antimelanoma effects of 4-S-cysteaminylphenol and its homologues. Melanoma Res 1998; 8:105-112.
8. Yamada K, Jimbow K. Selective in vivo and in vitro incorporation and accumulation of phenolic thioether amine into malignant melanoma and identification of a (58 kD) binding glycoprotein. Melanoma Res 1993; 2:225-233.
9. 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-S-cysteaminylphenol. Cancer Chemother Pharmacol 1992; 30:394-400.
10. Yamada I, Seki S, Ito S, Suzuki S, Matsubara O, Kasuga T. The killing effect of 4-S-cysteaminylphenol, a newly synthesized melanin precursor, on B16 melanoma cell lines. Br J Cancer 1991; 63:187-190.
11. 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.
12. Parsons PG, Favier F, McEwan M, Takahashi T, Jimbow K, Ito S. Action of cysteaminylphenols on human melanoma cells in vivo and in vitro: 4-S-cysteaminylphenol binds protein disulfide isomerase. Melanoma Res 1992; 1:97-104.
13. Kitagawa M, Nemoto T, Seki S, Ito S, Kasuga T. 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.
14. Alena F, Jimbow K, Ito S. Melanocytotoxicity and antimelanoma effects of phenolic amine compounds in mice in vivo. Cancer Res 1990; 50: 3743-3747.
15. Lane RM, Baker GB. Chirality and drugs used in psychiatry: nice to know or need to know? Cell Mol Neurobiol 1999; 19:355-372.
16. Dorey E. Chiral drugs viable, despite failure. Nature Biotech 2000; 18:1239-1240.
17. 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.
18. Wakamatsu K, Ito S, Rees JL. The usefulness of 4-amino-3- hydroxyphenylalanine as a specific marker of pheomelanin. Pigment Cell Res 2002; 15:162-173.
19. 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.
20. Padgette SR, Herman HH, Han JH, Pollock SH, May SW. Antihypertensive activities of phenyl aminoethyl sulfides, a class of synthetic substrates for dopamine β-hydroxylase. J Med Chem 1984; 27:1354-1357.
21. Meyers AI, Knaus G, Kamata K, Ford ME. Asymmetric synthesis of R and S α-alkylalkanoic acids from metalation and alkylation of chiral 2-oxazolines. J Am Chem Soc 1976; 98:567-576.
22. Olivares C, Garcia-Borron JC, Solano F. Identification of active site residues involved in metal cofactor binding and stereospecific substrate recognition in mammalian tyrosinase. Implications to the catalytic cycle. Biochemistry 2002; 41:679-686.
23. Solca FF, Chiuba-de Tapia J, Iwata K, Eberle AN. B16-G4F mouse melanoma cells: an MSH receptor-deficient cell clone. FEBS Lett 1993; 322:177-180.
24. Morrison ME, Yagi M, Cohen G. In vitro studies of 2,4- dihydroxyphenylalanine, a prodrug targeted against malignant melanoma cells. Proc Natl Acad Sci USA 1985; 82:2960-2964.
25. Gabby M, Tauber M, Porat S, Simantov R. Selective role of glutathione in protecting neural cells from dopamine-induced apoptosis. Neuropharmacology 1996; 35:571-578.
26. Romert L, Jenssen D. Mechanism of N-acetylcysteine (NAC) and other thiols as both positive and negative modifiers of MNNG-induced mutagenicity in V79 Chinese hamster cells. Carcinogenesis 1987; 8: 1531-1535.
27. del Olmo M, Alonso-Varona A, Castro B, Calle Y, Bilbao P, Palomares T. Effects of L-2-oxothiazolidine-4-carboxylate on the cytotoxic activity and toxicity of cyclophosphamide in mice bearing B16F10 melanoma liver metastases. Melanoma Res 2000; 10:103-112.