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Chemical Compound Review

NAPHTHOQUINONE     naphthalene-1,4-dione

Synonyms: NQ-1, PubChem22093, CHEMBL55934, SureCN42139, NSC-9583, ...
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Disease relevance of HSDB 2037


High impact information on HSDB 2037


Chemical compound and disease context of HSDB 2037


Biological context of HSDB 2037


Anatomical context of HSDB 2037


Associations of HSDB 2037 with other chemical compounds


Gene context of HSDB 2037

  • METHODS: We used a novel and potent Cdc25A inhibitor, 2,3-bis-[2-hydroxyethylsulfonyl]-[1,4] naphthoquinone (NSC 95397), and its congener (2-mercaptoethanol)-3-methyl-1, 4-naphthoquinone (NSC 672121) to study the role of Cdc25A on the MAPK pathway in human prostate cancer cells [25].
  • We now show that deletion of either napG or napH almost abolished Nap-dependent nitrate reduction by strains defective in naphthoquinone synthesis [26].
  • 58C80 [2-(4-t-butylcyclohexyl)-3-hydroxy-1,4-naphthoquinone] is an experimental naphthoquinone antimalarial drug which undergoes extensive alkyl hydroxylation to a single t-butylhydroxy metabolite in man in vivo and also in human liver microsomes, where this is catalysed primarily by a 54 kDa CYP2C9 form of cytochrome P450, P450hB20-27 [27].
  • Induction of p73beta by a naphthoquinone analog is mediated by E2F-1 and triggers apoptosis in HeLa cells [28].
  • 1,4-Naphthoquinone and four minor unknown metabolites from 1-naphthol were observed, and CYP1A2 and 2D6*1 were identified as the most active isoforms for the production of 1,4-naphthoquinone [29].

Analytical, diagnostic and therapeutic context of HSDB 2037


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  5. Isolation and identification of menaquinone-9 from purified nitrate reductase of Escherichia coli. Brito, F., DeMoss, J.A., Dubourdieu, M. J. Bacteriol. (1995) [Pubmed]
  6. Direct evidence that the rifamycin polyketide synthase assembles polyketide chains processively. Yu, T.W., Shen, Y., Doi-Katayama, Y., Tang, L., Park, C., Moore, B.S., Richard Hutchinson, C., Floss, H.G. Proc. Natl. Acad. Sci. U.S.A. (1999) [Pubmed]
  7. "Subversive" substrates for the enzyme trypanothione disulfide reductase: alternative approach to chemotherapy of Chagas disease. Henderson, G.B., Ulrich, P., Fairlamb, A.H., Rosenberg, I., Pereira, M., Sela, M., Cerami, A. Proc. Natl. Acad. Sci. U.S.A. (1988) [Pubmed]
  8. Geranyl diphosphate:4-hydroxybenzoate geranyltransferase from Lithospermum erythrorhizon. Cloning and characterization of a ket enzyme in shikonin biosynthesis. Yazaki, K., Kunihisa, M., Fujisaki, T., Sato, F. J. Biol. Chem. (2002) [Pubmed]
  9. Recruitment of a foreign quinone into the A1 site of photosystem I. In vivo replacement of plastoquinone-9 by media-supplemented naphthoquinones in phylloquinone biosynthetic pathway mutants of Synechocystis sp. PCC 6803. Johnson, T.W., Zybailov, B., Jones, A.D., Bittl, R., Zech, S., Stehlik, D., Golbeck, J.H., Chitnis, P.R. J. Biol. Chem. (2001) [Pubmed]
  10. Caspase-3-mediated cleavage of the NF-kappa B subunit p65 at the NH2 terminus potentiates naphthoquinone analog-induced apoptosis. Kang, K.H., Lee, K.H., Kim, M.Y., Choi, K.H. J. Biol. Chem. (2001) [Pubmed]
  11. Structural analysis of naphthoquinone protein adducts with liquid chromatography/tandem mass spectrometry and the scoring algorithm for spectral analysis (SALSA). Zhang, F., Bartels, M.J. Rapid Commun. Mass Spectrom. (2004) [Pubmed]
  12. Discriminating redox cycling and arylation pathways of reactive chemical toxicity in trout hepatocytes. Schmieder, P.K., Tapper, M.A., Kolanczyk, R.C., Hammermeister, D.E., Sheedy, B.R., Denny, J.S. Toxicol. Sci. (2003) [Pubmed]
  13. A Gene Cluster for Prenylated Naphthoquinone and Prenylated Phenazine Biosynthesis in Streptomyces cinnamonensis DSM 1042. Haagen, Y., Gl??ck, K., Fay, K., Kammerer, B., Gust, B., Heide, L. Chembiochem (2006) [Pubmed]
  14. Quinone-induced oxidative stress elevates glutathione and induces gamma-glutamylcysteine synthetase activity in rat lung epithelial L2 cells. Shi, M.M., Kugelman, A., Iwamoto, T., Tian, L., Forman, H.J. J. Biol. Chem. (1994) [Pubmed]
  15. Site-selective modification of hyperreactive cysteines of ryanodine receptor complex by quinones. Feng, W., Liu, G., Xia, R., Abramson, J.J., Pessah, I.N. Mol. Pharmacol. (1999) [Pubmed]
  16. 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]
  17. Comparative toxicity of alkyl-1,4-naphthoquinones in rats: relationship to free radical production in vitro. Munday, R., Fowke, E.A., Smith, B.L., Munday, C.M. Free Radic. Biol. Med. (1994) [Pubmed]
  18. Reaction products of 1-naphthol with reactive oxygen species prevent NADPH oxidase activation in activated human neutrophils, but leave phagocytosis intact. Hart, B.A., Simons, J.M., Rijkers, G.T., Hoogvliet, J.C., Van Dijk, H., Labadie, R.P. Free Radic. Biol. Med. (1990) [Pubmed]
  19. Synthesis of novel rhinacanthins and related anticancer naphthoquinone esters. Kongkathip, N., Luangkamin, S., Kongkathip, B., Sangma, C., Grigg, R., Kongsaeree, P., Prabpai, S., Pradidphol, N., Piyaviriyagul, S., Siripong, P. J. Med. Chem. (2004) [Pubmed]
  20. Antitumor agents. 89. Psychorubrin, a new cytotoxic naphthoquinone from Psychotria rubra and its structure-activity relationships. Hayashi, T., Smith, F.T., Lee, K.H. J. Med. Chem. (1987) [Pubmed]
  21. Vitamin K3 (menadione) and related quinones, like tumor-promoting phorbol esters, alter the affinity of epidermal growth factor for its membrane receptors. Shoyab, M., Todaro, G.J. J. Biol. Chem. (1980) [Pubmed]
  22. Oxidative protein modification as predigestive mechanism of the carnivorous plant Dionaea muscipula: an hypothesis based on in vitro experiments. Galek, H., Osswald, W.F., Elstner, E.F. Free Radic. Biol. Med. (1990) [Pubmed]
  23. Single electron reduction of xenobiotic compounds by glucose oxidase from Aspergillus niger. Metosh-Dickey, C.A., Mason, R.P., Winston, G.W. Free Radic. Biol. Med. (1998) [Pubmed]
  24. Epidermal ornithine decarboxylase induction and mouse skin tumor promotion by quinones. Monks, T.J., Walker, S.E., Flynn, L.M., Conti, C.J., DiGiovanni, J. Carcinogenesis (1990) [Pubmed]
  25. Activation of the Raf-1/MEK/Erk kinase pathway by a novel Cdc25 inhibitor in human prostate cancer cells. Nemoto, K., Vogt, A., Oguri, T., Lazo, J.S. Prostate (2004) [Pubmed]
  26. NapGH components of the periplasmic nitrate reductase of Escherichia coli K-12: location, topology and physiological roles in quinol oxidation and redox balancing. Brondijk, T.H., Nilavongse, A., Filenko, N., Richardson, D.J., Cole, J.A. Biochem. J. (2004) [Pubmed]
  27. Hydroxylation of the antimalarial drug 58C80 by CYP2C9 in human liver microsomes: comparison with mephenytoin and tolbutamide hydroxylations. Weaver, R.J., Dickins, M., Burke, M.D. Biochem. Pharmacol. (1995) [Pubmed]
  28. Induction of p73beta by a naphthoquinone analog is mediated by E2F-1 and triggers apoptosis in HeLa cells. Kang, K.H., Lee, J.H., Kim, K.C., Ham, S.W., Kim, M.Y., Choi, K.H. FEBS Lett. (2002) [Pubmed]
  29. In vitro metabolism of naphthalene by human liver microsomal cytochrome P450 enzymes. Cho, T.M., Rose, R.L., Hodgson, E. Drug Metab. Dispos. (2006) [Pubmed]
  30. Synthesis and biological studies of novel nucleoside phosphoramidate prodrugs. Tobias, S.C., Borch, R.F. J. Med. Chem. (2001) [Pubmed]
  31. Activation of a membrane-associated phosphatidylinositol kinase through tyrosine-protein phosphorylation by naphthoquinones and orthovanadate. Chen, Y.X., Yang, D.C., Brown, A.B., Jeng, Y., Tatoyan, A., Chan, T.M. Arch. Biochem. Biophys. (1990) [Pubmed]
  32. Cerebral toxoplasmosis in childhood and adult HIV infection treated with 1-4 hydroxynaphthoquinone and rapid desensitization with pyrimethamine. Bouboulis, D.A., Rubinstein, A., Shliozberg, J., Madden, J., Frieri, M. Ann. Allergy Asthma Immunol. (1995) [Pubmed]
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