title: Synthesis of cysteinylphenol, cysteaminylphenol, and related compounds, and in vivo evaluation of antimelanoma effect.
abstract: Phenolic and catecholic compounds were synthesized, by combination with cysteine or cysteamine through thioether bond, and their antimelanoma and melanocytotoxic effects were evaluated. Among nine compounds tested, 4-S-cysteaminylphenol (CAP) resulted in an increase in the life span (% ILS) of melanoma-bearing mice and in the growth inhibition (% GI) of melanoma tissue. 4-S-Cysteinylphenol (CP) and its methyl ester form also showed some increase in % GI. The 2-S-isomers of CP and CAP and diphenolic derivatives of CP did not show any significant antimelanoma effect. In addition, the s.c. injection of 4-S-CAP and 4-S-CP, in particular 4-S-CAP, caused the depigmentation of black hair which was manifested by loss of functioning melanocytes, as seen under light microscopy. The 4-S-CAP appears to provide a basis for development of a new class of antimelanoma and melanocytotoxic agents that are more stable than catecholic compounds, which have been most widely utilized as a source of rational chemotherapy for malignant melanoma.
authors: Department of Dermatology, Sapporo Medical College, Japan.
authors: S
authors: S
authors: Miura
authors: T
authors: T
authors: Ueda
authors: K
authors: K
authors: Jimbow
authors: S
authors: S
authors: Ito
authors: K
authors: K
authors: Fujita
mesh_terms: D000818:Animals; D003543:Cysteamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000627:therapeutic use; D003545:Cysteine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000627:therapeutic use; D004354:Drug Screening Assays, Antitumor; D005260:Female; D006200:Hair Color / Q000187:drug effects; D008544:Melanocytes / Q000187:drug effects; D008546:Melanoma, Experimental / Q000188:drug therapy*; D051379:Mice; D008810:Mice, Inbred C57BL; D011897:Random Allocation; D012878:Skin Neoplasms / Q000188:drug therapy*
chemical_list: D003543:Cysteamine; C043036:4-S-cysteinylphenol; C043037:4-S-cysteaminylphenol; D003545:Cysteine