Please check your email for instructions on resetting your password. In the first step, deprotonation leads to a phenoxide ion which is transformed into a phenoxy radical by a one-electron oxidation. abstract = "Exposure of humans and experimental animals to benzene has been shown to result in hematotoxicity such as pancytopenia, aplastic anemia, and leukemia. is available on our Permission Requests page. Denisov, E.T., Denisova, T.G., and Pokidova, T.S., Handbook of Free Radical Initiators, Hoboken, N.J.: Wiley, 2003. ChemInform Abstract: Oxidation of Hydroquinones and Hydroquinone Monomethyl Ethers to Quinones with tert‐Butyl Hydroperoxide and Catalytic Amounts of Ceric Ammonium Nitrate (CAN).. A New Gold‐Catalyzed Domino Cyclization and Oxidative Coupling Reaction. AU - Trush, Michael A. PY - 1993/1 Kinetics and mechanism of the reaction of ascorbic acid, hydroquinone, and catechol with 12-tungstocobaltoate(III) Institute of Problems of Chemical Physics, Russian Academy of Sciences, Chernogolovka, Moscow oblast, 142432, Russia, You can also search for this author in When the peroxidation reaction was followed at the absorbance maxima of the corresponding benzoquinones (Q, DMQ, TMQ) a distinct lag phase was Mogilevich, M.M. E-mail: - 37.139.31.67. Synthesis of a regioisomeric analogue of the 3C-protease inhibitor thysanone via a Hauser annulation strategy. In the presence of myeloperoxidase, Cu(II)-mediated oxidation of HQ was increased. and Trush, {Michael A.}". Oxidation of Hydroquinones and Hydroquinone Monomethyl Ethers to Quinones with tert‐Butyl Hydroperoxide and Catalytic Amounts of Ceric Ammonium Nitrate (CAN) Karsten Krohn Prof. Working off-campus? In phosphate-buffered saline, HQ underwent autoxidation slowly to BQ, while the presence of Cu(II) ions (1, 2.5, 5, 10, 50 μM) strongly accelerated the oxidation of HQ to BQ in a concentration-dependent manner. E. T. Denisov. Handbook on the Physics and Chemistry of Rare Earths Volume 36, https://doi.org/10.1002/1521-3897(200010)342:8<825::AID-PRAC825>3.0.CO;2-3. The oxidative activation of the benzene metabolite, hydroquinone (HQ), in the bone marrow to the electrophilic benzoquinone (BQ) has been suggested to play an important role in benzene-induced hematotoxicity. Since the interaction of several xenobiotics with copper has been shown to result in their metabolism, in this study we have investigated the role of copper in the oxidation of HQ and HQ-induced toxicity to mice hone marrow stromal cells, target cells of HQ in the bone marrow. and Denisov, E.T., Kinet. Learn more. The resulting H2O2 is further utilized as an oxidant by the Co(II)–HCO3− complex in situ with the formation of the ˙OH radical, which is highly active for H2Q oxidation and even for dye degradation. Denisov, E.T. The enhanced cytotoxicity of HQ by Cu(II) could be completely prevented by adding BCS, glutathione (GSH), or dithiothreitol but not by catalase. Dissociation of the second OH group generates the radical anion semiquinone followed by a second one-electron … Please enable JavaScript E-mail address: kkcommat;chemie.uni‐paderborn.de. The above results indicate that Cu(II) strongly induces the oxidation of HQ and as such may be a factor involved in the oxidative activation and toxicity of HQ in target cells. The redox equilibria between the dihydroxybenzenes hydroquinone and catechol and their quinone oxidation states are so facile that milder oxidants than chromate (Jones reagent) are generally preferred. Learn about our remote access options, Paderborn, Universität, Fachbereich Chemie und Chemietechnik. Reaction of HQ with Cu(II) was also accompanied by the reduction of Cu(II) to Cu(I), the utilization of O2, and the concomitant generation of H2O2. In addition, oxidation of HQ by Cu(II) also generated chemiluminescence. Google Scholar. article provided that the correct acknowledgement is given with the reproduced material. Use the link below to share a full-text version of this article with your friends and colleagues. with the reproduced material. Oxidation of hydroquinone by copper: Chemical mechanism and biological effects, Chemical mechanism and biological effects. / Li, Yunbo B.; Trush, Michael A. T1 - Oxidation of hydroquinone by copper, T2 - Chemical mechanism and biological effects. 517–523. The oxidative activation of the benzene metabolite, hydroquinone (HQ), in the bone marrow to the electrophilic benzoquinone (BQ) has been suggested to play an important role in benzene-induced hematotoxicity. https://doi.org/10.1134/S0023158411040136. This may take some time to load. Authors contributing to RSC publications (journal articles, books or book chapters) Katal., 1991, vol. and Afanas’ev, I.B., Oxidation and Antioxidants in Organic Chemistry and Biology, Boca Raton, Fla.: Taylor and Francis, 2005. Dive into the research topics of 'Oxidation of hydroquinone by copper: Chemical mechanism and biological effects'. Together they form a unique fingerprint. D. Zhang, W. Shi, Q. Cheng, X. Li and A. Xu, School of Environmental Engineering, Wuhan Textile University, Wuhan 430200, China, School of Chemistry and Chemical Engineering, Wuhan Textile University, Wuhan 430200, China, Engineering Research Center for Clean Production of Dyeing and Printing, Ministry of Education, Wuhan Textile University, Wuhan, China, Instructions for using Copyright Clearance Center page. For reproduction of material from all other RSC journals and books: For reproduction of material from all other RSC journals. By observing the kinetics of the reactions derived from mixing 100 μM HQ and 100 μM Cu(II), it was found that all of the Cu(II) was reduced to Cu(I) within 5 s, followed by consumption of O2 and the generation of BQ, which reached maximum levels at 4 min after mixing HQ and Cu(II).

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