ArgTX-636, a polyamine isolated from spider venom: A novel class of melanogenesis inhibitors

Bioorg Med Chem. 2016 Nov 15;24(22):5685-5692. doi: 10.1016/j.bmc.2016.08.023. Epub 2016 Aug 27.

Abstract

To discover new molecules with an inhibitory activity of melanogenesis a hundred of scorpions, snakes, spiders and amphibians venoms were screened for their capacity to inhibit mushroom tyrosinase using 3,4-l-dihydroxyphenylalanine (l-DOPA) as substrate. The Argiope lobata spider venom proved to be the most active. HPLC fraction containing Argiotoxine-636 (ArgTX-636), a polyamine known for its numerous biological activities, was found to also show a good regulation activity of melanogenesis by inhibiting DOPA and 5,6-dihydroxyindole-2-carboxylic acid (DHICA) oxidases activities, wore by tyrosinase (TYR) and tyrosinase-related protein 1 (TRP-1), respectively. Our results demonstrate that ArgTX-636 reduced the mushroom tyrosinase activity in a dose-dependent way with a maximal half inhibitory concentration (IC50) value of 8.34μM, when l-DOPA is used as substrate. The Lineweaver-Burk study showed that ArgTX-636 is a mixed type inhibitor of the diphenolase activity. Moreover, ArgTX-636 inhibits DHICA oxydase activity of mushroom tyrosinase activity with IC50 at 41.3μM. ArgTX-636 has no cytotoxicity in B16F10 melanoma cells at concentrations up to 42.1μM. The effect of ArgTX-636 on melanogenesis showed that melanin production in B16F10 melanoma cell decreased by approximatively 70% compared to untreated cells. ArgTX-636 displayed no significant effect on the TYR expression while the protein level of TRP-1 decreased in B16F10 cells. Thus, ArgTX-636 could have particular interest for cosmetic and/or pharmaceutical use in order to reduce important dermatoses in black and mixed skins.

Keywords: ArgTX-636; Argiotoxine; DHICA oxydase activity; DOPA oxydase activity; Hyperpigmentation; Melanogenesis; Spider venoms; Tyrosinase; Tyrosinase related protein 1 (TRP-1).

MeSH terms

  • Animals
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Dose-Response Relationship, Drug
  • Indoleacetic Acids / chemistry
  • Indoleacetic Acids / isolation & purification
  • Indoleacetic Acids / pharmacology*
  • Melanins / antagonists & inhibitors*
  • Melanins / metabolism
  • Mice
  • Molecular Structure
  • Polyamines / chemistry
  • Polyamines / isolation & purification
  • Polyamines / pharmacology*
  • Spider Venoms / chemistry*
  • Structure-Activity Relationship

Substances

  • Indoleacetic Acids
  • Melanins
  • Polyamines
  • Spider Venoms
  • argiotoxin-636