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Chemical Compound Review

CHEMBL52347     naphthalene-1,2-dione

Synonyms: SureCN173316, CPD-4895, NSC-9831, ACMC-1B0WP, CCRIS 1558, ...
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Disease relevance of beta-Naphthoquinone


High impact information on beta-Naphthoquinone

  • Beta-Lapachone, a derivative of 1,2-naphthoquinone, inhibits the specific binding of [6,7-3H]triamcinolone acetonide (TA) to unbound hepatic and thymic glucocorticoid receptors in a dose-dependent manner with 50% of the maximal inhibition in thymus cytosol achieved at a final concentration of 5-10 microM [6].
  • We also found that naphthoquinones, including 1,2-naphthoquinone, inhibit PTEN in the cell-free system, which suggested that the effect on PTEN (and thus the effect on phosphatidylinositol 3-kinase signaling) should be taken into account when examining the pharmacological actions of naphthoquinone derivatives [7].
  • beta-Lapachone, an o-naphthoquinone, induces a novel caspase- and p53-independent apoptotic pathway dependent on NAD(P)H:quinone oxidoreductase 1 (NQO1) [8].
  • The enzymatically generated o-quinones, e.g., naphthalene-1,2-dione and benzo[a]pyrene-7,8-dione are potent inhibitors of the dehydrogenase, yielding IC50 values of 5.0 and 10.0 microM, respectively [9].
  • Addition of beta-lapachone, an o-naphthoquinone endowed with trypanocidal properties to respiring Trypanosoma cruzi epimastigotes induced the release of O2- and H2O2 from the whole cells to the suspending medium [10].

Chemical compound and disease context of beta-Naphthoquinone

  • Aethiopinone (1), an o-naphthoquinone diterpene from Salvia aethiopis L. roots and two hemisynthetic derivatives 2 and 3 have been evaluated for toxicity, anti-inflammatory, analgesic, antipyretic, and haemostatic activities [11].

Biological context of beta-Naphthoquinone


Anatomical context of beta-Naphthoquinone


Associations of beta-Naphthoquinone with other chemical compounds


Gene context of beta-Naphthoquinone


Analytical, diagnostic and therapeutic context of beta-Naphthoquinone


  1. Mechanisms of toxic injury to isolated hepatocytes by 1-naphthol. Doherty, M.D., Cohen, G.M., Smith, M.T. Biochem. Pharmacol. (1984) [Pubmed]
  2. Cytotoxicity of polycyclic aromatic hydrocarbon o-quinones in rat and human hepatoma cells. Flowers-Geary, L., Harvey, R.G., Penning, T.M. Chem. Res. Toxicol. (1993) [Pubmed]
  3. The cytotoxicity and mechanisms of 1,2-naphthoquinone thiosemicarbazone and its metal derivatives against MCF-7 human breast cancer cells. Chen, J., Huang, Y.W., Liu, G., Afrasiabi, Z., Sinn, E., Padhye, S., Ma, Y. Toxicol. Appl. Pharmacol. (2004) [Pubmed]
  4. Naphthoquinone-Induced cataract in mice: possible involvement of Ca2+ release and calpain activation. Qian, W., Shichi, H. Journal of ocular pharmacology and therapeutics : the official journal of the Association for Ocular Pharmacology and Therapeutics. (2001) [Pubmed]
  5. Quantitation of beta-lapachone and 3-hydroxy-beta-lapachone in human plasma samples by reversed-phase high-performance liquid chromatography. Glen, V.L., Hutson, P.R., Kehrli, N.J., Boothman, D.A., Wilding, G. J. Chromatogr. B Biomed. Sci. Appl. (1997) [Pubmed]
  6. Beta-lapachone, a specific competitive inhibitor of ligand binding to the glucocorticoid receptor. Schmidt, T.J., Miller-Diener, A., Litwack, G. J. Biol. Chem. (1984) [Pubmed]
  7. A naphthoquinone derivative, shikonin, has insulin-like actions by inhibiting both phosphatase and tensin homolog deleted on chromosome 10 and tyrosine phosphatases. Nigorikawa, K., Yoshikawa, K., Sasaki, T., Iida, E., Tsukamoto, M., Murakami, H., Maehama, T., Hazeki, K., Hazeki, O. Mol. Pharmacol. (2006) [Pubmed]
  8. Development of beta-lapachone prodrugs for therapy against human cancer cells with elevated NAD(P)H:quinone oxidoreductase 1 levels. Reinicke, K.E., Bey, E.A., Bentle, M.S., Pink, J.J., Ingalls, S.T., Hoppel, C.L., Misico, R.I., Arzac, G.M., Burton, G., Bornmann, W.G., Sutton, D., Gao, J., Boothman, D.A. Clin. Cancer Res. (2005) [Pubmed]
  9. Non-K-region o-quinones as enzyme-generated inactivators of dihydrodiol dehydrogenase. Penning, T.M., Sharp, R.B., Smithgall, T.E. Biochemistry (1989) [Pubmed]
  10. Effect of beta-lapachone on superoxide anion and hydrogen peroxide production in Trypanosoma cruzi. Boveris, A., Docampo, R., Turrens, J.F., Stoppani, A.O. Biochem. J. (1978) [Pubmed]
  11. Analgesic, anti-inflammatory, antipyretic and haematological effects of aethiopinone, an o-naphthoquinone diterpenoid from Salvia aethiopis roots and two hemisynthetic derivatives. Hernández-Pérez, M., Rabanal, R.M., de la Torre, M.C., Rodríguez, B. Planta Med. (1995) [Pubmed]
  12. Redox cycling of beta-lapachone and related o-naphthoquinones in the presence of dihydrolipoamide and oxygen. Molina Portela, M.P., Stoppani, A.O. Biochem. Pharmacol. (1996) [Pubmed]
  13. Polycyclic aromatic hydrocarbon (PAH) ortho-quinone conjugate chemistry: kinetics of thiol addition to PAH ortho-quinones and structures of thioether adducts of naphthalene-1,2-dione. Murty, V.S., Penning, T.M. Chem. Biol. Interact. (1992) [Pubmed]
  14. Inhibition of endothelial nitric oxide synthase activity and suppression of endothelium-dependent vasorelaxation by 1,2-naphthoquinone, a component of diesel exhaust particles. Sun, Y., Taguchi, K., Sumi, D., Yamano, S., Kumagai, Y. Arch. Toxicol. (2006) [Pubmed]
  15. Effect of dyskinetoplastic agents on ultrastructure and oxidative phosphorylation in Crithidia fasciculata. Biscardi, A.M., Lopez, L.M., de Pahn, E.M., Pellegrino de Iraldi, A., Stoppani, A.O. Biocell (2001) [Pubmed]
  16. Quinone induced stimulation of hexose monophosphate shunt activity in the guinea pig lens: role of zeta-crystallin. Rao, P., Zigler, J.S. Biochim. Biophys. Acta (1992) [Pubmed]
  17. Characteristics of Ca2+ transport by Trypanosoma cruzi mitochondria in situ. Docampo, R., Vercesi, A.E. Arch. Biochem. Biophys. (1989) [Pubmed]
  18. Naphthoquinone cataract in mice: mitochondrial change and protection by superoxide dismutase. Martynkina, L.P., Qian, W., Shichi, H. Journal of ocular pharmacology and therapeutics : the official journal of the Association for Ocular Pharmacology and Therapeutics. (2002) [Pubmed]
  19. Effect of the lipophilic o-naphthoquinone CG 10-248 on rat liver mitochondria structure and function. Lopez, L.M., Pellegrino de Iraldi, A., Carrizo, P.H., Dubin, M., Stoppani, A.O. Biocell (2002) [Pubmed]
  20. Apoptogenic effect of the lipophilic o-naphthoquinone CG 10-248 on rat hepatocytes: light and electron microscopy studies. Lopez, L.M., Dubin, M., Carrizo, P.H., Burgos, M.H., Pellegrino de Iraldi, A., Stoppani, A.O. Biocell (2003) [Pubmed]
  21. Alkylation of DNA with aziridine produced during the hydrolysis of N,N',N''-triethylenethiophosphoramide. Musser, S.M., Pan, S.S., Egorin, M.J., Kyle, D.J., Callery, P.S. Chem. Res. Toxicol. (1992) [Pubmed]
  22. Development of polyclonal antibodies for detection of protein modification by 1,2-naphthoquinone. Zheng, J., Hammock, B.D. Chem. Res. Toxicol. (1996) [Pubmed]
  23. Difference in glutathione S-transferase response to oxidative stress between porcine and bovine lens. Nishinaka, T., Terada, T., Nanjo, H., Mizoguchi, T., Nishihara, T. Exp. Eye Res. (1993) [Pubmed]
  24. Studies on photoinduced H-atom and electron transfer reactions of o-naphthoquinones by laser flash photolysis. Pan, Y., Fu, Y., Liu, S., Yu, H., Gao, Y., Guo, Q., Yu, S. The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment & general theory. (2006) [Pubmed]
  25. Pharmacokinetic screening of o-naphthoquinone 5-lipoxygenase inhibitors. Rakhit, A., Kuwahara, S.K., Jones, D.R., Soliman, V.F., Kotake, A.N., Oglesby, T.D., Wasley, J.W., Tripp, S.L., Douglas, F.L. Pharm. Res. (1990) [Pubmed]
  26. Prevention of naphthalene-1,2-dihydrodiol-induced lens protein modifications by structurally diverse aldose reductase inhibitors. Sato, S., Sugiyama, K., Lee, Y.S., Kador, P.F. Exp. Eye Res. (1999) [Pubmed]
  27. A naphthoquinone adsorbent for affinity chromatography of human dihydropteridine reductase. Cotton, R.G., Jennings, I. Eur. J. Biochem. (1978) [Pubmed]
  28. Comparative molecular similarity indices analysis (CoMSIA) studies of 1,2-naphthoquinone derivatives as PTP1B inhibitors. Sobhia, M.E., Bharatam, P.V. Bioorg. Med. Chem. (2005) [Pubmed]
  29. Amphetamine and methamphetamine determination in urine by reversed-phase high-performance liquid chromatography with simultaneous sample clean-up and derivatization with 1,2-naphthoquinone 4-sulphonate on solid-phase cartridges. Campíns-Falcó, P., Sevillano-Cabeza, A., Molíns-Legua, C., Kohlmann, M. J. Chromatogr. B, Biomed. Appl. (1996) [Pubmed]
  30. Ketopantoyl lactone reductase is a conjugated polyketone reductase. Hata, H., Shimizu, S., Hattori, S., Yamada, H. FEMS Microbiol. Lett. (1989) [Pubmed]
  31. Improved amphetamine and methamphetamine determination in urine by normal-phase high-performance liquid chromatography with sodium 1,2-naphthoquinone 4-sulphonate as derivatizing agent and solid-phase extraction for sample clean-up. Campíns Falcó, P., Molins Legua, C., Herráez Hernandez, R., Sevillano Cabeza, A. J. Chromatogr. B, Biomed. Appl. (1995) [Pubmed]
  32. Xenobiotic induction of quinone oxidoreductase activity in lens epithelial cells. Tumminia, S.J., Rao, P.V., Zigler, J.S., Russell, P. Biochim. Biophys. Acta (1993) [Pubmed]
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