Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
1
pubmed:dateCreated
2000-6-21
pubmed:abstractText
Exposure of the skin to certain phenols or catechols such as 4-tert-butylphenol (TBP) and 4-tert-butylcatechol (TBC) may cause leukoderma. These substances are used in the polymer industry and numerous cases have been reported. Several theories of the mechanism for chemical leukoderma have been suggested. In the present study, TBP and TBC are shown to be oxidised by tyrosinase. The oxidation of TBC yields a quinone that is further investigated on its reactions with cysteine or glutathione (GSH). The products formed are isolated and identified by mass spectrometry and nuclear magnetic resonance as being 4-tert-butyl-6-S-cysteinylcatechol (cys-TBC) and 4-tert-butyl-6-S-glutathionylcatechol (GS-TBC). The reactive quinone is a strongly electrophilic substance that rapidly reacts with GSH. A depletion of the GSH defence system may give conditions where the quinone lives long enough to effect its toxic properties. The influence of the reactive tert-butylquinone on enzymatic activities is demonstrated by the inhibition of glyceraldehyde-3-phosphate dehydrogenase.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Feb
pubmed:issn
0893-5785
pubmed:author
pubmed:issnType
Print
pubmed:volume
13
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
33-8
pubmed:dateRevised
2006-11-15
pubmed:meshHeading
pubmed-meshheading:10761994-Agaricales, pubmed-meshheading:10761994-Antioxidants, pubmed-meshheading:10761994-Catechols, pubmed-meshheading:10761994-Chromatography, High Pressure Liquid, pubmed-meshheading:10761994-Cysteine, pubmed-meshheading:10761994-Glutathione, pubmed-meshheading:10761994-Glyceraldehyde-3-Phosphate Dehydrogenases, pubmed-meshheading:10761994-Humans, pubmed-meshheading:10761994-Magnetic Resonance Spectroscopy, pubmed-meshheading:10761994-Melanocytes, pubmed-meshheading:10761994-Melanoma, pubmed-meshheading:10761994-Monophenol Monooxygenase, pubmed-meshheading:10761994-Oxidation-Reduction, pubmed-meshheading:10761994-Phenols, pubmed-meshheading:10761994-Pigmentation, pubmed-meshheading:10761994-Pigments, Biological, pubmed-meshheading:10761994-Quinones, pubmed-meshheading:10761994-Tumor Cells, Cultured
pubmed:year
2000
pubmed:articleTitle
Tyrosinase-mediated formation of a reactive quinone from the depigmenting agents, 4-tert-butylphenol and 4-tert-butylcatechol.
pubmed:affiliation
Department of Dermatology, University of Lund, Sweden.
pubmed:publicationType
Journal Article, Research Support, Non-U.S. Gov't