The cytotoxicity of cysteinylcatechols and related compounds to human melanoma cells in vitro

J Invest Dermatol. 1987 May;88(5):538-40. doi: 10.1111/1523-1747.ep12470098.

Abstract

L-3,4-Dihydroxyphenylalanine (L-dopa) and its structural analogs are known to be potently cytotoxic to melanoma cells. We examined the effects of cysteinylcatechols and related compounds, which were newly synthesized as cysteinyl derivatives of L-dopa, on the growth of human melanoma cells in vitro, and their actions were compared with those of L-dopa. 4-S- and 3-S-Cysteinylcatechols showed significantly more potent cytotoxicity to melanoma cells than did L-dopa, and 2-S-cysteinylhydroquinone was next to the catechols in potency. The mechanism of action may involve interaction with the melanocyte-specific enzyme, tyrosinase, for which the cysteinylcatechols could become a better substrate than L-dopa itself. 4-S-Cysteaminylphenol was almost comparable to L-dopa in cytotoxicity, suggesting that this phenol might be oxidized to the corresponding catechol by tyrosinase within the melanoma cells.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / pharmacology*
  • Catechols / toxicity*
  • Cell Division / drug effects
  • Cell Line
  • Cell Survival
  • Cysteine / analogs & derivatives*
  • Cysteine / toxicity
  • Dose-Response Relationship, Drug
  • Humans
  • Levodopa / pharmacology
  • Melanoma / pathology*
  • Phenols / pharmacology
  • Time Factors

Substances

  • Antineoplastic Agents
  • Catechols
  • Phenols
  • Levodopa
  • Cysteine