Jump to ContentJump to Main Navigation
Show Summary Details
More options …

Biological Chemistry

Editor-in-Chief: Brüne, Bernhard

Editorial Board: Buchner, Johannes / Lei, Ming / Ludwig, Stephan / Sies, Helmut / Thomas, Douglas D. / Turk, Boris / Wittinghofer, Alfred

IMPACT FACTOR 2017: 3.022

CiteScore 2017: 2.81

SCImago Journal Rank (SJR) 2017: 1.562
Source Normalized Impact per Paper (SNIP) 2017: 0.705

See all formats and pricing
More options …
Volume 383, Issue 12


Tyrosinase-Mediated Oxidation of Acetaminophen to 4-Acetamido-o- Benzoquinone

E. Valero / R. Varón / F. García-Carmona
Published Online: 2005-06-01 | DOI: https://doi.org/10.1515/BC.2002.217


Based on its monophenolic structure and given its pharmacological and toxicological importance, the ability of tyrosinase to oxidize acetaminophen was studied for the first time. Progress curves showed a transient phase characteristic of the monophenolase activity of tyrosinase prior to attaining the steadystate. The duration of this transient phase strongly increased with the drug concentration, which would partly explain why paracetamol oxidation by tyrosinase has not been studied hitherto. The pathway is enhanced by the presence of minute amounts of Ldopa, which shortens the length of the lag period. Acetaminophen oxidation was inhibited by tropolone, a selective inhibitor of tyrosinase. The presence of the corresponding odiphenol as intermediate was demonstrated with ascorbic acid by chemical oxidation using NaIO4 and by HPLC analysis, indicating that acetaminophen is oxidized by the monophenolase activity of tyrosinase to its corresponding oquinone. These results contribute to our knowledge of the oxidation mechanisms of acetaminophen.

About the article

Published Online: 2005-06-01

Published in Print: 2002-12-09

Citation Information: Biological Chemistry, Volume 383, Issue 12, Pages 1931–1939, ISSN (Print) 1431-6730, DOI: https://doi.org/10.1515/BC.2002.217.

Export Citation

Citing Articles

Here you can find all Crossref-listed publications in which this article is cited. If you would like to receive automatic email messages as soon as this article is cited in other publications, simply activate the “Citation Alert” on the top of this page.

Yoshihiro Uesawa, Naotaka Tsuji, and Saikat Dewanjee
PLOS ONE, 2018, Volume 13, Number 10, Page e0205612
Aysu Yarman, Katharina Jetzschmann, Bettina Neumann, Xiaorong Zhang, Ulla Wollenberger, Aude Cordin, Karsten Haupt, and Frieder Scheller
Chemosensors, 2017, Volume 5, Number 2, Page 11
Aysu Yarman and Frieder W. Scheller
Electroanalysis, 2016, Volume 28, Number 9, Page 2222
Carole Calas-Blanchard, Georges Istamboulié, Margot Bontoux, Gaël Plantard, Vincent Goetz, and Thierry Noguer
Chemosphere, 2015, Volume 131, Page 124
Sidy Ba, Lounes Haroune, Carles Cruz-Morató, Chloé Jacquet, Imad E. Touahar, Jean-Phillipe Bellenger, Claude Y. Legault, J. Peter Jones, and Hubert Cabana
Science of The Total Environment, 2014, Volume 487, Page 748
Edelmira Valero, Ramón Varón, and Francisco Garcı́a-Carmona
Archives of Biochemistry and Biophysics, 2003, Volume 416, Number 2, Page 218
M.I. González-Sánchez, J. Rubio-Retama, E. López-Cabarcos, and E. Valero
Biosensors and Bioelectronics, 2011, Volume 26, Number 5, Page 1883
Nikhil M. Vad, Garret Yount, Dan Moore, Jon Weidanz, and Majid Y. Moridani
Journal of Pharmaceutical Sciences, 2009, Volume 98, Number 4, Page 1409
Fernando Gandía-Herrero, Josefa Escribano, and Francisco García-Carmona
Planta, 2005, Volume 222, Number 2, Page 307

Comments (0)

Please log in or register to comment.
Log in