Tyrosinase-mediated oxidation of acetaminophen to 4-acetamido-o-benzoquinone.

Abstract:

: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 steady-state. 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 L-dopa, which shortens the length of the lag period. Acetaminophen oxidation was inhibited by tropolone, a selective inhibitor of tyrosinase. The presence of the corresponding o-diphenol 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 o-quinone. These results contribute to our knowledge of the oxidation mechanisms of acetaminophen.

journal_name

Biol Chem

journal_title

Biological chemistry

authors

Valero E,Varón R,García-Carmona F

doi

10.1515/BC.2002.217

keywords:

subject

Has Abstract

pub_date

2002-12-01 00:00:00

pages

1931-9

issue

12

eissn

1431-6730

issn

1437-4315

journal_volume

383

pub_type

杂志文章
  • Maintaining protein composition in cilia.

    abstract::The primary cilium is a sensory organelle that is vital in regulating several signalling pathways. Unlike most organelles cilia are open to the rest of the cell, not enclosed by membranes. The distinct protein composition is crucial to the function of cilia and many signalling proteins and receptors are specifically c...

    journal_title:Biological chemistry

    pub_type: 杂志文章,评审

    doi:10.1515/hsz-2017-0168

    authors: Stephen LA,Elmaghloob Y,Ismail S

    更新日期:2017-12-20 00:00:00

  • Click reactions with functional sphingolipids.

    abstract::Sphingolipids and glycosphingolipids can regulate cell recognition and signalling. Ceramide and sphingosine-1-phosphate are major players in the sphingolipid pathways and are involved in the initiation and regulation of signalling, apoptosis, stress responses and infection. Specific chemically synthesised sphingolipid...

    journal_title:Biological chemistry

    pub_type: 杂志文章,评审

    doi:10.1515/hsz-2018-0169

    authors: Fink J,Seibel J

    更新日期:2018-09-25 00:00:00

  • Characterisation and glucoregulatory actions of a novel acylated form of the (Pro3)GIP receptor antagonist in type 2 diabetes.

    abstract::In this study, we tested the biological activity of a novel acylated form of (Pro3)glucose-dependent insulinotropic polypetide [(Pro3)GIP] prepared by conjugating palmitic acid to Lys16 to enhance its efficacy in vivo by promoting binding to albumin and extending its biological actions. Like the parent molecule (Pro3)...

    journal_title:Biological chemistry

    pub_type: 杂志文章

    doi:10.1515/BC.2007.019

    authors: Gault VA,Hunter K,Irwin N,Greer B,Green BD,Harriott P,O'Harte FP,Flatt PR

    更新日期:2007-02-01 00:00:00

  • Placental expression of proteases and their inhibitors in patients with HELLP syndrome.

    abstract::In preeclampsia and hemolysis, elevated liver enzymes and low platelet (HELLP) syndrome, impaired trophoblast invasion and excessive fibrin deposition in the placental intervillous space is associated with fetal compromise. However, little information is available whether modulation of placental protease expression--p...

    journal_title:Biological chemistry

    pub_type: 杂志文章

    doi:10.1515/BC.2009.123

    authors: von Steinburg SP,Krüger A,Fischer T,Mario Schneider KT,Schmitt M

    更新日期:2009-11-01 00:00:00

  • Characterization of the chicken and rat DCoH gene domains using an improved ligation-mediated PCR method.

    abstract::The bifunctional protein DCoH (dimerization cofactor of HNF-1) is a transcriptional coactivator of homeodomain proteins and a cytoplasmic enzyme. Here we report on the isolation, nucleotide sequence and genomic structure of the chicken and rat DCoH genes. They have an unusual first exon coding for a single amino acid....

    journal_title:Biological chemistry

    pub_type: 杂志文章

    doi:

    authors: Bossow S,Riepl S,Igo-Kemenes T

    更新日期:1998-11-01 00:00:00

  • Establishment of a hybrid SalI-HgiDII type II restriction-modification system.

    abstract::In the SalI system, endonuclease activity can be only achieved in the presence of a functional modification gene. Thus, the DNA methyltransferase is involved in the control of restriction. By fusion of the restriction gene of the SalI system to the modification gene of the isospecific HgiDII system a hybrid type II re...

    journal_title:Biological chemistry

    pub_type: 杂志文章

    doi:

    authors: Pélaez AI,Ribas-Aparicio RM,Gómez A,Rodicio MR

    更新日期:1998-04-01 00:00:00

  • Nitrite, a naturally occurring precursor of nitric oxide that acts like a 'prodrug'.

    abstract::There are enzymatic and non-enzymatic mechanisms that generate NO* from nitrite in blood, stomach, saliva, urine and skin. In blood vessels, nitrite-derived NO* can provide protection via compensatory vasodilation during hypoxia, and in various body fluids it may have antibacterial activity. In the skin, nitrite-deriv...

    journal_title:Biological chemistry

    pub_type: 杂志文章,评审

    doi:10.1515/BC.2006.065

    authors: Suschek CV,Schewe T,Sies H,Kröncke KD

    更新日期:2006-05-01 00:00:00

  • Sequence elements outside the catalytic core of natural hairpin ribozymes modulate the reactions differentially.

    abstract::Abstract Hairpin ribozymes occur naturally only in the satellite RNAs of tobacco ringspot virus (TRsV), chicory yellow mottle virus (CYMoV) and arabis mosaic virus (ArMV). The catalytic centre of the predominantly studied sTRsV hairpin ribozyme, and of sArMV is organised around a four-way helical junction. We show her...

    journal_title:Biological chemistry

    pub_type: 杂志文章

    doi:10.1515/BC.2011.071

    authors: Bajaj P,Steger G,Hammann C

    更新日期:2011-07-01 00:00:00

  • The hyaluronan-binding serine protease from human plasma cleaves HMW and LMW kininogen and releases bradykinin.

    abstract::The influence of the hyaluronan-binding protease (PHBSP), a plasma enzyme with FVII- and pro-urokinase-activating potency, on components of the contact phase (kallikrein/kinin) system was investigated. No activation or cleavage of the proenzymes involved in the contact phase system was observed. The pro-cofactor high ...

    journal_title:Biological chemistry

    pub_type: 杂志文章

    doi:10.1515/BC.2002.184

    authors: Etscheid M,Beer N,Fink E,Seitz R,Johannes D

    更新日期:2002-10-01 00:00:00

  • Cellular expression of plasma prekallikrein in human tissues.

    abstract::Plasma prekallikrein (PPK) is synthesised in hepatocytes and secreted into the blood, where it participates in the surface-dependent activation of blood coagulation, fibrinolysis, kinin generation and inflammation. Recently we demonstrated by quantitative RT-PCR that the human PPK gene is transcribed not only in the l...

    journal_title:Biological chemistry

    pub_type: 杂志文章

    doi:10.1515/BC.2007.104

    authors: Fink E,Bhoola KD,Snyman C,Neth P,Figueroa CD

    更新日期:2007-09-01 00:00:00

  • Chemistry and biochemistry of cold physical plasma derived reactive species in liquids.

    abstract::Reactive oxygen and nitrogen species deposited by cold physical plasma are proposed as predominant effectors in the interaction between discharge and biomedical application. Most reactive species found in plasma sources are known in biology for inter- and intracellular communication (redox signaling) and mammalian cel...

    journal_title:Biological chemistry

    pub_type: 杂志文章,评审

    doi:10.1515/hsz-2018-0242

    authors: Wende K,von Woedtke T,Weltmann KD,Bekeschus S

    更新日期:2018-12-19 00:00:00

  • Protective activity of aromatic amines and imines against oxidative nerve cell death.

    abstract::Oxidative stress is a widespread phenomenon in the pathology of neurodegenerative diseases such as Alzheimer's disease, Parkinson's disease, and amyotrophic lateral sclerosis. Neuronal cell death due to oxidative stress may causally contribute to the pathogeneses of these diseases. Therefore, neuroprotective antioxida...

    journal_title:Biological chemistry

    pub_type: 杂志文章

    doi:10.1515/BC.2001.195

    authors: Moosmann B,Skutella T,Beyer K,Behl C

    更新日期:2001-11-01 00:00:00

  • Contribution of astrocytes to metabolic dysfunction in the Alzheimer's disease brain.

    abstract::Historically considered as accessory cells to neurons, there is an increasing interest in the role of astrocytes in normal and pathological conditions. Astrocytes are involved in neurotransmitter recycling, antioxidant supply, ion buffering and neuroinflammation, i.e. a lot of the same pathways that go astray in Alzhe...

    journal_title:Biological chemistry

    pub_type: 杂志文章,评审

    doi:10.1515/hsz-2019-0140

    authors: Zulfiqar S,Garg P,Nieweg K

    更新日期:2019-08-27 00:00:00

  • Processive proteolysis by γ-secretase and the mechanism of Alzheimer's disease.

    abstract::γ-Secretase is a membrane-embedded protease complex with presenilin as the catalytic component. Cleavage within the transmembrane domain of the amyloid β-protein precursor (APP) by γ-secretase produces the C-terminus of the amyloid β-peptide (Aβ), a proteolytic product prone to aggregation and strongly linked to Alzhe...

    journal_title:Biological chemistry

    pub_type: 杂志文章,评审

    doi:10.1515/hsz-2012-0140

    authors: Wolfe MS

    更新日期:2012-09-01 00:00:00

  • Characterization of the specific DNA nicking activity of restriction endonuclease N.BstNBI.

    abstract::N.BstNBI is a unique restriction endonuclease isolated from Bacillus stearothermophilus. We have characterized the recognition sequence and the cleavage site of N.BstNBI. Mapping of cleavage sites of N.BstNBI showed that it recognizes an asymmetric sequence, 5' GAGTC 3', and cleaves only on the top strand 4 base pairs...

    journal_title:Biological chemistry

    pub_type: 杂志文章

    doi:10.1515/BC.2000.137

    authors: Morgan RD,Calvet C,Demeter M,Agra R,Kong H

    更新日期:2000-11-01 00:00:00

  • Ultraviolet B radiation induces cell shrinkage and increases osmolyte transporter mRNA expression and osmolyte uptake in HaCaT keratinocytes.

    abstract::We have previously shown that compatible organic osmolytes, such as betaine, myo-inositol and taurine, are part of the stress response of normal human keratinocytes (NHKs) to ultraviolet B (UVB) radiation. In this regard, we tested human HaCaT keratinocytes as a surrogate cell line for NHK. HaCaT cells osmo-dependentl...

    journal_title:Biological chemistry

    pub_type: 杂志文章

    doi:10.1515/BC.2007.140

    authors: Warskulat U,Brookmann S,Reinen A,Häussinger D

    更新日期:2007-12-01 00:00:00

  • Enhancing the immunogenicity of exogenous hepatitis B surface antigen-based vaccines for MHC-I-restricted T cells.

    abstract::Vaccination with either exogenous hepatitis B surface antigen (HBsAg) lipoprotein particles without adjuvants, or plasmid DNA encoding secreted small HBsAg stimulate long-lasting, potent antibody responses in H-2d (BALB/c) and C57Bl/6 (H-2b) mice. Vaccination with exogenous HBsAg primes MHC-I restricted cytotoxic T ly...

    journal_title:Biological chemistry

    pub_type: 杂志文章,评审

    doi:10.1515/BC.1999.039

    authors: Schirmbeck R,Reimann J

    更新日期:1999-03-01 00:00:00

  • Monitoring human parvovirus B19 virus-like particles and antibody complexes in solution by fluorescence correlation spectroscopy.

    abstract::Fluorescence correlation spectroscopy (FCS) was used in monitoring human parvovirus B19 virus-like particle (VLP) antibody complexes from acute phase and past-immunity serum samples. The Oregon Green 488-labeled VLPs gave an average diffusion coefficient of 1.7 x 10(-7) cm2 s(-1) with an apparent hydrodynamic radius o...

    journal_title:Biological chemistry

    pub_type: 杂志文章

    doi:10.1515/BC.2004.011

    authors: Toivola J,Michel PO,Gilbert L,Lahtinen T,Marjomäki V,Hedman K,Vuento M,Oker-Blom C

    更新日期:2004-01-01 00:00:00

  • Methylation of the RASSF1A gene in human cancers.

    abstract::Loss of genetic material from chromosome 3p21.3 is one of the most common and earliest events in the pathogenesis of lung cancer and many other solid tumors. The chromosomal area 3p21.3 is thought to harbor at least one important tumor suppressor gene, which, despite many years of investigation, has remained elusive. ...

    journal_title:Biological chemistry

    pub_type: 杂志文章,评审

    doi:10.1515/BC.2002.097

    authors: Pfeifer GP,Yoon JH,Liu L,Tommasi S,Wilczynski SP,Dammann R

    更新日期:2002-06-01 00:00:00

  • Superoxide anion and hydrogen peroxide-induced signaling and damage in angiotensin II and aldosterone action.

    abstract::The formation of reactive oxygen species (ROS) can be induced by xenobiotic substances, such as redox cycling molecules, but also by endogenous substances such as hormones and cytokines. Recent research shows the importance of ROS in cellular signaling. Here, the signaling pathways of the two blood pressure-regulating...

    journal_title:Biological chemistry

    pub_type: 杂志文章,评审

    doi:10.1515/BC.2010.136

    authors: Queisser N,Fazeli G,Schupp N

    更新日期:2010-11-01 00:00:00

  • Oxidative nerve cell death in Alzheimer's disease and stroke: antioxidants as neuroprotective compounds.

    abstract::Many neurodegenerative disorders and syndromes are associated with an excessive generation of reactive oxygen species (ROS) and oxidative stress. The pathways to nerve cell death induced by diverse potential neurotoxins such as peptides, excitatory amino acids, cytokines or synthetic drugs commonly share oxidative dow...

    journal_title:Biological chemistry

    pub_type: 杂志文章,评审

    doi:10.1515/BC.2002.053

    authors: Behl C,Moosmann B

    更新日期:2002-03-01 00:00:00

  • Cis-regulatory sequences from the first intron of the rat glutamine synthetase gene are involved in hepatocyte specific expression of the enzyme.

    abstract::In order to identify regulatory elements involved in the hepatocyte specific expression of the enzyme glutamine synthetase [GS (E.C. 6.3.1.2)] we analyzed the first intron of the rat GS gene. A sequence analysis detected clusters of potential transcription factor binding sites in regions that are hypersensitive for DN...

    journal_title:Biological chemistry

    pub_type: 杂志文章

    doi:10.1515/bchm.1997.378.1.11

    authors: Gaunitz F,Gaunitz C,Papke M,Gebhardt R

    更新日期:1997-01-01 00:00:00

  • The activity and localization patterns of cathepsins B and X in cells of the mouse gastrointestinal tract differ along its length.

    abstract::Cysteine cathepsins are expressed in most tissues, including the gastrointestinal tract. We demonstrated an involvement of mouse intestinal cathepsin B in extracellular matrix remodeling for regeneration from trauma. The present study aimed at elucidating roles of cysteine cathepsins in the non-traumatized gastrointes...

    journal_title:Biological chemistry

    pub_type: 杂志文章

    doi:10.1515/hsz-2014-0151

    authors: Tamhane T,Arampatzidou M,Gerganova V,Tacke M,Illukkumbura R,Dauth S,Schaschke N,Peters C,Reinheckel T,Brix K

    更新日期:2014-10-01 00:00:00

  • FAM134B promotes adipogenesis by increasing vesicular activity in porcine and 3T3-L1 adipocytes.

    abstract::Family with sequence similarity 134, Member B (FAM134B), is a cis-Golgi transmembrane protein that is known to be necessary for the long-term survival of nociceptive and autonomic ganglion neurons. Recent work has shown that FAM134B plays a pivotal role in autophagy-mediated turnover of endoplasmic reticulum (ER) memb...

    journal_title:Biological chemistry

    pub_type: 杂志文章

    doi:10.1515/hsz-2018-0336

    authors: Cai M,Chen J,Yu C,Xi L,Jiang Q,Wang Y,Wang X

    更新日期:2019-03-26 00:00:00

  • Regulation of cathepsin B activity by cysteine and related thiols.

    abstract::We studied the mode of regulation of the activity of mature cathepsin B (CB) by L-cysteine and some related thiols. The activity of CB with Z-Arg-Arg-NHMec as substrate was gradually inhibited over a range of increasing concentration of Cys, Cys methyl ester (CysOMe), Cys ethyl ester (CysOEt), N-acetyl-Cys (N-AcCys) a...

    journal_title:Biological chemistry

    pub_type: 杂志文章

    doi:10.1515/BC.1999.069

    authors: Krepela E,Procházka J,Kárová B

    更新日期:1999-05-01 00:00:00

  • Transmembrane phospholipid distribution in blood cells: control mechanisms and pathophysiological significance.

    abstract::This review deals with current concepts on the regulation and function of phospholipid asymmetry in biological membranes. This ubiquitous phenomenon is characterized by a distinctly different lipid composition between the inner and outer leaflet of the membrane bilayer. Transbilayer asymmetry is controlled by differen...

    journal_title:Biological chemistry

    pub_type: 杂志文章,评审

    doi:

    authors: Bevers EM,Comfurius P,Dekkers DW,Harmsma M,Zwaal RF

    更新日期:1998-08-01 00:00:00

  • Tailor-made dyes for fluorescence correlation spectroscopy (FCS).

    abstract::Two new fluorescent labels are presented that are optimized for excitation with He/Ne laser and red diode lasers. Application in FCS and labeling of proteins and oligomers are demonstrated. A strong rise of quantum yield and emission life time upon binding to biomolecules are characteristic features of the dyes. ...

    journal_title:Biological chemistry

    pub_type: 杂志文章

    doi:10.1515/BC.2001.062

    authors: Czerney P,Lehmann F,Wenzel M,Buschmann V,Dietrich A,Mohr GJ

    更新日期:2001-03-01 00:00:00

  • Transcriptional activity of GLI1 is negatively regulated by protein kinase A.

    abstract::The transcription factor GLI1 is one of three vertebrate members of the GLI family, which is characterized by a highly conserved DNA-binding domain of five zinc fingers. We have analyzed whether human GLI1 is a target of PKA regulation. It was found that PKA inhibits GLI1 transcriptional activity. However, no evidence...

    journal_title:Biological chemistry

    pub_type: 杂志文章

    doi:10.1515/BC.2000.070

    authors: Kaesler S,Lüscher B,Rüther U

    更新日期:2000-07-01 00:00:00

  • Mannose 6-phosphate receptor-dependent endocytosis of lysosomal enzymes is increased in sulfatide-storing kidney cells.

    abstract::Metachromatic leukodystrophy is a lysosomal disorder caused by the deficiency of arylsulfatase A (ASA). This leads to the storage of the sphingolipid 3-O-sulfogalactosylceramide (sulfatide) in various cell types, such as renal tubular cells. Examination of mannose 6-phosphate receptor (MPR300)-dependent endocytosis re...

    journal_title:Biological chemistry

    pub_type: 杂志文章

    doi:10.1515/BC.2009.009

    authors: Klein D,Yaghootfam A,Matzner U,Koch B,Braulke T,Gieselmann V

    更新日期:2009-01-01 00:00:00

  • Structure and reaction mechanism of L-arginine:glycine amidinotransferase.

    abstract::L-Arginine:glycine amidinotransferase (AT) catalyzes the committed step in creatine biosynthesis by formation of guanidinoacetic acid, the direct precursor of creatine. The X-ray structure of the human enzyme shows a novel fold with fivefold pseudosymmetry of beta beta alphabeta-modules. These modules enclose the acti...

    journal_title:Biological chemistry

    pub_type: 杂志文章,评审

    doi:

    authors: Humm A,Fritsche E,Steinbacher S

    更新日期:1997-03-01 00:00:00