Chemical Compound Review:
o-Quinone cyclohexa-2,4-diene-1,6-dione
Synonyms:
o-Benzoquinone, CPD-385, SureCN113494, AG-G-06448, CHEBI:17253, ...
- Semiquinone anion radicals from addition of amino acids, peptides, and proteins to quinones derived from oxidation of catechols and catecholamines. An ESR spin stabilization study. Kalyanaraman, B., Premovic, P.I., Sealy, R.C. J. Biol. Chem. (1987)
- Bioactivation of estrone and its catechol metabolites to quinoid-glutathione conjugates in rat liver microsomes. Iverson, S.L., Shen, L., Anlar, N., Bolton, J.L. Chem. Res. Toxicol. (1996)
- Formation of ortho-benzoquinone from sodium benzoate by Pseudomonas mendocina P2d. Parulekar, C., Mavinkurve, S. Indian J. Exp. Biol. (2006)
- A novel o-aminophenol oxidase responsible for formation of the phenoxazinone chromophore of grixazone. Suzuki, H., Furusho, Y., Higashi, T., Ohnishi, Y., Horinouchi, S. J. Biol. Chem. (2006)
- Spectroscopic identification of ortho-quinones as the products of polycyclic aromatic trans-dihydrodiol oxidation catalyzed by dihydrodiol dehydrogenase. A potential route of proximate carcinogen metabolism. Smithgall, T.E., Harvey, R.G., Penning, T.M. J. Biol. Chem. (1988)
- A dopaquinone model that mimics the water addition step of cofactor biogenesis in copper amine oxidases. Ling, K.Q., Sayre, L.M. J. Am. Chem. Soc. (2005)
- Photoaddition of water and alcohols to the anthracene moiety of 9-(2'-hydroxyphenyl)anthracene via formal excited state intramolecular proton transfer. Flegel, M., Lukeman, M., Huck, L., Wan, P. J. Am. Chem. Soc. (2004)
- Cloning and characterization of red clover polyphenol oxidase cDNAs and expression of active protein in Escherichia coli and transgenic alfalfa. Sullivan, M.L., Hatfield, R.D., Thoma, S.L., Samac, D.A. Plant Physiol. (2004)
- Bioreductive activation of catechol estrogen-ortho-quinones: aromatization of the B ring in 4-hydroxyequilenin markedly alters quinoid formation and reactivity. Shen, L., Pisha, E., Huang, Z., Pezzuto, J.M., Krol, E., Alam, Z., van Breemen, R.B., Bolton, J.L. Carcinogenesis (1997)
- Quercetin may act as a cytotoxic prooxidant after its metabolic activation to semiquinone and quinoidal product. Metodiewa, D., Jaiswal, A.K., Cenas, N., Dickancaité, E., Segura-Aguilar, J. Free Radic. Biol. Med. (1999)
- Effect of stypoldione on cell cycle progression, DNA and protein synthesis, and cell division in cultured sea urchin embryos. White, S.J., Jacobs, R.S. Mol. Pharmacol. (1983)
- Mechanism of action of the marine natural product stypoldione: evidence for reaction with sulfhydryl groups. O'Brien, E.T., Asai, D.J., Groweiss, A., Lipshutz, B.H., Fenical, W., Jacobs, R.S., Wilson, L. J. Med. Chem. (1986)
- Catalytic oxidation of 2-aminophenols and ortho hydroxylation of aromatic amines by tyrosinase. Toussaint, O., Lerch, K. Biochemistry (1987)
- Investigation of the catalytic site of actinidin by using benzofuroxan as a reactivity probe with selectivity for the thiolate-imidazolium ion-pair systems of cysteine proteinases. Evidence that the reaction of the ion-pair of actinidin (pKI 3.0, pKII 9.6) is modulated by the state of ionization of a group associated with a molecular pKa of 5.5. Salih, E., Brocklehurst, K. Biochem. J. (1983)
- A bioactive metabolite of benzo[a]pyrene, benzo[a]pyrene-7,8-dione, selectively alters microsomal Ca2+ transport and ryanodine receptor function. Pessah, I.N., Beltzner, C., Burchiel, S.W., Sridhar, G., Penning, T., Feng, W. Mol. Pharmacol. (2001)
- Mechanism of selective toxicity of 4-S-cysteinylphenol and 4-S-cysteaminylphenol to melanocytes. Ito, S., Kato, T., Ishikawa, K., Kasuga, T., Jimbow, K. Biochem. Pharmacol. (1987)
- Synthesis and reactivity of the catechol metabolites from the equine estrogen, 8,9-dehydroestrone. Zhang, F., Yao, D., Hua, Y., van Breemen, R.B., Bolton, J.L. Chem. Res. Toxicol. (2001)
- New cytotoxic-antineoplastic prenyl-1,2-naphthohydroquinone derivatives. Molinari, A., Oliva, A., Ojeda, C., Miguel del Corral, J.M., Castro, M.A., Cuevas, C., San Feliciano, A. Bioorg. Med. Chem. (2005)
- Oxidative metabolites of 5-S-cysteinyldopamine inhibit the alpha-ketoglutarate dehydrogenase complex: possible relevance to the pathogenesis of Parkinson's disease. Shen, X.M., Li, H., Dryhurst, G. Journal of neural transmission (Vienna, Austria : 1996) (2000)
- Nitric oxide promotes strong cytotoxicity of phenolic compounds against Escherichia coli: the influence of antioxidant defenses. Urios, A., López-Gresa, M.P., González, M.C., Primo, J., Martínez, A., Herrera, G., Escudero, J.C., O'Connor, J.E., Blanco, M. Free Radic. Biol. Med. (2003)
- Zeptomole-detecting biosensor for alkaline phosphatase in an electrochemical immunoassay for 2,4-dichlorophenoxyacetic acid. Bauer, C.G., Eremenko, A.V., Ehrentreich-Förster, E., Bier, F.F., Makower, A., Halsall, H.B., Heineman, W.R., Scheller, F.W. Anal. Chem. (1996)
- Amplification of amperometric biosensor responses by electrochemical substrate recycling. 3. Theoretical and experimental study of the phenol-polyphenol oxidase system immobilized in Laponite hydrogels and layer-by-layer self-assembled structures. Coche-Guerente, L., Labbé, P., Mengeaud, V. Anal. Chem. (2001)
- Tyrosinase kinetics: failure of the auto-activation mechanism of monohydric phenol oxidation by rapid formation of a quinomethane intermediate. Cooksey, C.J., Garratt, P.J., Land, E.J., Ramsden, C.A., Riley, P.A. Biochem. J. (1998)
- DNA strand scission by polycyclic aromatic hydrocarbon o-quinones: role of reactive oxygen species, Cu(II)/Cu(I) redox cycling, and o-semiquinone anion radicals,. Flowers, L., Ohnishi, S.T., Penning, T.M. Biochemistry (1997)
- Oxygen Michaelis constants for tyrosinase. Rodríguez-López, J.N., Ros, J.R., Varón, R., García-Cánovas, F. Biochem. J. (1993)
- p-Quinone methides are the major decomposition products of catechol estrogen o-quinones. Bolton, J.L., Shen, L. Carcinogenesis (1996)
- Chemical evidence for the pH-dependent control of ion-pair geometry in cathepsin B. Benzofuroxan as a reactivity probe sensitive to differences in the mutual disposition of the thiolate and imidazolium components of cysteine proteinase catalytic sites. Willenbrock, F., Brocklehurst, K. Biochem. J. (1986)
- Retention of NADPH-linked quinone reductase activity in an aldo-keto reductase following mutation of the catalytic tyrosine. Schlegel, B.P., Ratnam, K., Penning, T.M. Biochemistry (1998)
- Cellular biochemical determinants modulating the metabolism of estrone 3,4-quinone. Nutter, L.M., Zhou, B., Sierra, E.E., Wu, Y.Y., Rummel, M.M., Gutierrez, P., Abul-Hajj, Y. Chem. Res. Toxicol. (1994)
- Synthesis and liquid chromatography/tandem mass spectrometric characterization of the adducts of bisphenol A o-quinone with glutathione and nucleotide monophosphates. Qiu, S.X., Yang, R.Z., Gross, M.L. Chem. Res. Toxicol. (2004)
- Peroxidative free radical formation and O-demethylation of etoposide(VP-16) and teniposide(VM-26). Haim, N., Roman, J., Nemec, J., Sinha, B.K. Biochem. Biophys. Res. Commun. (1986)
- Rapid and highly sensitive electrochemical determination of alkaline phosphatase using a composite tyrosinase biosensor. Serra, B., Morales, M.D., Reviejo, A.J., Hall, E.H., Pingarrón, J.M. Anal. Biochem. (2005)
- The oxidation of the highly tumorigenic benz[a]anthracene 3,4-dihydrodiol by rat liver dihydrodiol dehydrogenase. Klein, J., Post, K., Thomas, H., Wörner, W., Setiabudi, F., Frank, H., Oesch, F., Platt, K.L. Chem. Biol. Interact. (1990)
- Isolation of estradiol-2,3-quinone and its intermediary role in melanin formation. Jacobsohn, M.K., Byler, D.M., Jacobsohn, G.M. Biochim. Biophys. Acta (1991)