Effects of quinone derivatives, such as 1,4-naphthoquinone, on DNA polymerase inhibition and anti-inflammatory action

Med Chem. 2011 Jan;7(1):37-44. doi: 10.2174/157340611794072742.


Previously, we reported that vitamin K(3), which consists of a quinone component, inhibits the activity of human DNA polymerase γ (pol γ). In this study, we investigated the inhibitory effects of 4 quinone derivatives (1,4-benzoquinone (BQ), 1,4-naphthoquinone (NQ), 9,10-anthraquinone (AQ) and 5,12-naphthacenequinone (NCQ)) on the activity of mammalian pols. BQ and NQ potently inhibited the activity of all the pol species: pols α, β, γ, δ, ε and λ, and NQ was a stronger pol inhibitor than BQ. Because we previously found a positive relationship between pol l inhibition and anti-inflammatory action, we examined whether these quinone derivatives could inhibit inflammatory responses. BQ and NQ caused a marked reduction in 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced acute inflammation in mouse ear, although AQ and NCQ did not. In a cell culture system using mouse macrophages, NQ displayed the strongest suppression in the production of tumor necrosis factor (TNF)-α induced by lipopolysaccharide (LPS) among the quinone derivatives tested. Moreover, NQ was found to inhibit the action of nuclear factor (NF)-κ. In an in vivo mouse model of LPS-evoked acute inflammation, intraperitoneal injection of BQ and NQ to mice led to suppression of TNF-α production in serum. These anti-inflammatory responses of NQ were more potent than those of BQ. In conclusion, this study has identified several quinone derivatives, such as NQ, that are promising anti-inflammatory candidates.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anthraquinones / pharmacology*
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology*
  • Antifibrinolytic Agents / pharmacology
  • Cattle
  • Cell Line
  • DNA-Directed DNA Polymerase / metabolism
  • Enzyme Inhibitors / pharmacology*
  • Female
  • Genes, pol
  • Humans
  • Inflammation / chemically induced
  • Inflammation / drug therapy*
  • Macrophages / drug effects
  • Mice
  • Mice, Inbred C57BL
  • Naphthoquinones / pharmacology*
  • Nucleic Acid Synthesis Inhibitors*
  • Rats
  • Vitamin K 3 / pharmacology*


  • Anthraquinones
  • Anti-Inflammatory Agents, Non-Steroidal
  • Antifibrinolytic Agents
  • Enzyme Inhibitors
  • Naphthoquinones
  • Nucleic Acid Synthesis Inhibitors
  • Vitamin K 3
  • DNA-Directed DNA Polymerase
  • 1,4-naphthoquinone