Document Detail


NO scavenging by 3-hydroxyanthranilic acid and 3-hydroxykynurenine: N-nitrosation leads via oxadiazoles to o-quinone diazides.
MedLine Citation:
PMID:  18675929     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
The tryptophan metabolites kynurenine, 3-hydroxykynurenine, anthranilic, 3-hydroxyanthranilic and 3-methoxyanthranilic acids were compared with regard to diazotation by .NO or NO+, using three different donors, nitrite at pH 5, PAPA-NONOate at pH 7.4 and NO+SbF(6)- at pH 2.0. With all three sources of NO species, 3-hydroxykynurenine and 3-hydroxyanthranilic acid were readily nitrosated, thereby forming an intensely yellow compound. Nitrosation of the non-hydroxylated analogs did not lead to colored products within the period of observation. Competition experiments, using PAPA-NONOate as NO donor, showed that 3-hydroxyanthranilic acid is a more potent NO scavenger than N-acetylcysteine. Nitrosation of 3-hydroxykynurenine and 3-hydroxyanthranilic acid leads, presumably via a nitrosamine intermediate, to a diazonium ion, which forms an oxadiazole tautomerizing to a yellow o-quinone diazide. While the diazonium-derived quinone diazide is apparently the sole product detected directly after incubation of 3-hydroxyanthranilic acid, additional substances are formed from 3-hydroxykynurenine. Contrary to rapid carbenium ion formation from diazonium ions of non-hydroxylated anilines, nitrogen is practically not released from oxadiazoles/quinone diazides at moderate temperatures. Since carbenium ions are known to cause adduct formation with other biomolecules, and since non-hydroxylated anilines and their aminophenol analogs differ in their reactions following diazotation, these findings should be of relevance for the relative toxicity of anilines.
Authors:
Claudia Backhaus; Hafizur Rahman; Sebastian Scheffler; Hartmut Laatsch; Rüdiger Hardeland
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Publication Detail:
Type:  Journal Article     Date:  2008-07-17
Journal Detail:
Title:  Nitric oxide : biology and chemistry / official journal of the Nitric Oxide Society     Volume:  19     ISSN:  1089-8611     ISO Abbreviation:  Nitric Oxide     Publication Date:  2008 Nov 
Date Detail:
Created Date:  2008-10-17     Completed Date:  2008-12-22     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9709307     Medline TA:  Nitric Oxide     Country:  United States    
Other Details:
Languages:  eng     Pagination:  237-44     Citation Subset:  IM    
Affiliation:
Johann Friedrich Blumenbach Institute of Zoology and Anthropology, University of Goettingen, Berliner Strasse 28, D-37073 Goettingen, Lower Saxony, Germany.
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MeSH Terms
Descriptor/Qualifier:
3-Hydroxyanthranilic Acid / pharmacology*
Acetylcysteine / pharmacology
Aminophenols
Anthranilic Acids / pharmacology
Chromatography, Thin Layer
Diazonium Compounds / metabolism
Free Radical Scavengers / pharmacology*
Hydrazines
Inflammation
Kynurenine / analogs & derivatives*,  pharmacology
Magnetic Resonance Imaging
Mass Spectrometry
Nitric Oxide
Nitrites
Nitrosation
Nuclear Magnetic Resonance, Biomolecular
Oxadiazoles / metabolism*
Quinones / metabolism
Tryptophan / metabolism
Chemical
Reg. No./Substance:
0/Aminophenols; 0/Anthranilic Acids; 0/Diazonium Compounds; 0/Free Radical Scavengers; 0/Hydrazines; 0/Nitrites; 0/Oxadiazoles; 0/PAPA NONOate; 0/Quinones; 10102-43-9/Nitric Oxide; 118-92-3/anthranilic acid; 343-65-7/Kynurenine; 484-78-6/3-hydroxykynurenine; 548-93-6/3-Hydroxyanthranilic Acid; 616-91-1/Acetylcysteine; 73-22-3/Tryptophan

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