Regulatory effect of hydroquinone-tetraethylene glycol conjugates on zebrafish pigmentation

Bioorg Med Chem Lett. 2016 Jan 15;26(2):699-705. doi: 10.1016/j.bmcl.2015.09.059. Epub 2015 Sep 26.

Abstract

We synthesized two hydroquinone-tetraethylene glycol conjugates (HQ-TGs) and investigated their logP, photophysical stability, and redox chemical stability. HQ-TGs are a little more hydrophilic than hydroquinone (HQ) and show an enhanced photophysical and redox chemical stability compared with HQ. In addition we studied the effect of HQ-TGs on cell viability and on zebrafish pigmentation. MTT assay in HF-16 cells showed HQ-TGs are less cytotoxic than HQ. The phenotype-based image analysis of zebrafish larvae suggests that HQ-TGs suppress the pigmentation of zebrafish in a dose-dependent manner. The comparative experiments on stability, cytotoxicity, and zebrafish pigmentation between HQ and HQ-TGs suggest that mono tetraethylene glycol-functionalization of HQ is an alternative solution to overcome the adverse effect of HQ.

Keywords: Hydroquinone; Hydroquinone–tetraethylene glycol conjugate; Pigmentation; Whitening effect; Zebrafish.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cell Line
  • Cell Survival / drug effects
  • Ethylene Glycols / chemistry
  • Ethylene Glycols / pharmacology*
  • Hydroquinones / chemistry
  • Hydroquinones / pharmacology*
  • Larva / drug effects
  • Larva / physiology
  • Models, Molecular
  • Pigmentation / drug effects*
  • Skin Lightening Preparations / chemistry
  • Skin Lightening Preparations / pharmacology*
  • Zebrafish / physiology*

Substances

  • Ethylene Glycols
  • Hydroquinones
  • Skin Lightening Preparations
  • hydroquinone