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Chemical Compound Review

DHNQ     5,8-dihydroxynaphthalene-1,4- dione

Synonyms: NAPHTHAZALIN, Naphthazarin, Naphthazarine, Naphthazarone, NQ-2, ...
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Disease relevance of Dihydroxynaphthoquinone


High impact information on Dihydroxynaphthoquinone

  • A model of 5,8-dihydroxy-1,4-naphthoquinone interaction with the zinc finger region of the retroviral integrase protein is proposed [5].
  • Although both cell types did undergo apoptosis when exposed to the lysosomotropic detergent MSDH, the redox-cycling quinone naphthazarin, or the protein kinase inhibitor staurosporine, I-cells exerted a markedly decreased response to these agonists than did normal fibroblasts [6].
  • Guanabenz inhibited, the leakage of lysosomal cathepsin D to cytosol, the decreased mitochondrial potential, and the release of mitochondrial cytochrome c, which were induced by naphthazarin [7].
  • We now report on a study into the protective effects of rilmenidine and AGN 192403, which have affinity for imidazoline-1 receptors, on the cytotoxicity induced by naphthazarin and inhibitors of mitochondrial respiration in astrocytes [8].
  • Immunofluorescence analysis of the intracellular distribution of cathepsin D revealed a distinct granular pattern in control cells, whereas cells treated with naphthazarin for 30 min exhibited more diffuse staining that corresponded to release of the enzyme from lysosomes to the cytosol [9].

Biological context of Dihydroxynaphthoquinone


Anatomical context of Dihydroxynaphthoquinone


Associations of Dihydroxynaphthoquinone with other chemical compounds


Gene context of Dihydroxynaphthoquinone


Analytical, diagnostic and therapeutic context of Dihydroxynaphthoquinone


  1. Some substituted naphthazarins as potential anticancer agents. Paull, K.D., Zee-Cheng, R.K., Cheng, C.C. J. Med. Chem. (1976) [Pubmed]
  2. Inhibitory effect of a naphthazarin derivative, S64, on heat shock factor (Hsf) activation and glutathione status following hypoxia. Park, E.M., Lee, I.J., Kim, S.H., Song, G.Y., Park, Y.M. Cell Biol. Toxicol. (2003) [Pubmed]
  3. Constituents of Tritonia crocosmaeflora, I. Tricrozarin A, a novel antimicrobial naphthazarin derivative. Masuda, K., Funayama, S., Komiyama, K., Umezawa, I., Ito, K. J. Nat. Prod. (1987) [Pubmed]
  4. Cytotoxicity in vitro of naphthazarin derivatives from Onosma arenaria. Kundaković, T., Stanojković, T., Juranić, Z., Kovacević, N. Phytotherapy research : PTR. (2006) [Pubmed]
  5. Inhibitors of human immunodeficiency virus integrase. Fesen, M.R., Kohn, K.W., Leteurtre, F., Pommier, Y. Proc. Natl. Acad. Sci. U.S.A. (1993) [Pubmed]
  6. Decreased apoptotic response of inclusion-cell disease fibroblasts: a consequence of lysosomal enzyme missorting? Terman, A., Neuzil, J., Kågedal, K., Ollinger, K., Brunk, U.T. Exp. Cell Res. (2002) [Pubmed]
  7. Imidazoline drugs stabilize lysosomes and inhibit oxidative cytotoxicity in astrocytes. Choi, S.H., Choi, D.H., Lee, J.J., Park, M.S., Chun, B.G. Free Radic. Biol. Med. (2002) [Pubmed]
  8. Protective effects of rilmenidine and AGN 192403 on oxidative cytotoxicity and mitochondrial inhibitor-induced cytotoxicity in astrocytes. Choi, D.H., Kim, D.H., Park, Y.G., Chun, B.G., Choi, S.H. Free Radic. Biol. Med. (2002) [Pubmed]
  9. Lysosomal release of cathepsin D precedes relocation of cytochrome c and loss of mitochondrial transmembrane potential during apoptosis induced by oxidative stress. Roberg, K., Johansson, U., Ollinger, K. Free Radic. Biol. Med. (1999) [Pubmed]
  10. Comparative study on cytogenetic effects by diplatinum complexes of the ligands of naphthazarine and squaric acid in human lymphocytes. Lialiaris, T., Mourelatos, D., Boutis, L., Papageorgiou, A., Christianopoulou, M., Papageorgiou, V., Dozi-Vassiliades, J. J. Pharmacol. Exp. Ther. (1989) [Pubmed]
  11. A pre-embedding technique for immunocytochemical visualization of cathepsin D in cultured cells subjected to oxidative stress. Roberg, K., Ollinger, K. J. Histochem. Cytochem. (1998) [Pubmed]
  12. Relocalization of cathepsin D and cytochrome c early in apoptosis revealed by immunoelectron microscopy. Roberg, K. Lab. Invest. (2001) [Pubmed]
  13. 2-Substituted naphthazarins; synthesis and antitumor activity. Kyong-Up, B., Yong, S.G., Yong, K., Dai-Eun, S., Byung-Zun, A. Arch. Pharm. (Weinheim) (1997) [Pubmed]
  14. Study of the redox properties of naphthazarin (5,8-dihydroxy-1,4-naphthoquinone) and its glutathionyl conjugate in biological reactions: one- and two-electron enzymatic reduction. Ollinger, K., Llopis, J., Cadenas, E. Arch. Biochem. Biophys. (1989) [Pubmed]
  15. Inhibition of cathepsin D prevents free-radical-induced apoptosis in rat cardiomyocytes. Ollinger, K. Arch. Biochem. Biophys. (2000) [Pubmed]
  16. In vitro inhibition of the metabolism and mutagenicity of benzo(a)pyrene and benzo(a)pyrene-7,8-dihydrodiol by naphthazarin and other naphthol derivatives. Espino, P.C., Sullivan, P.D. Biochem. Biophys. Res. Commun. (1987) [Pubmed]
  17. Conformational and electrostatic properties of naphthazarin, juglone, and naphthoquinone: an ab initio theoretical study. Bhattacharjee, A.K., Pundlik, S.S., Gadre, S.R. Cancer Invest. (1997) [Pubmed]
  18. Naphthazarin derivatives (IV): synthesis, inhibition of DNA topoisomerase I and cytotoxicity of 2- or 6-acyl-5,8-dimethoxy-1, 4-naphthoquinones. Song, G.Y., Kim, Y., Zheng, X.G., You, Y.J., Cho, H., Chung, J.H., Sok, D.E., Ahn, B.Z. European journal of medicinal chemistry. (2000) [Pubmed]
  19. Studies on a new antibiotic M-92 produced by Micromonospora. II. Isolation and physicochemical properties of M-92 and its components. Tani, K., Takaishi, T. J. Antibiot. (1982) [Pubmed]
  20. Fourier transform infrared and Raman spectra, vibrational assignment and density functional theory calculations of naphthazarin. Tabrizi, M.Z., Tayyari, S.F., Tayyari, F., Behforouz, M. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. (2004) [Pubmed]
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