Document Detail


4-fluoro-2-methoxyphenol, an apocynin analog with enhanced inhibitory effect on leukocyte oxidant production and phagocytosis.
MedLine Citation:
PMID:  21497599     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Apocynin, a methoxy-substituted catechol (4-hydroxy-3-methoxyacetophenone), originally extracted from the roots of Picrorhiza kurroa, has been extensively used as a non-toxic inhibitor of the multienzymatic complex NADPH oxidase. We discovered that the analogous methoxy-substituted catechol, 4-Fluoro-2-methoxyphenol (F-apocynin), in which the acetyl group present in apocynin was changed to a fluorine atom, was significantly more potent as an inhibitor of NADPH oxidase activity, myeloperoxidase (MPO) chlorinating activity and phagocytosis of microorganisms by neutrophils; it was also as potent as apocynin in inhibiting tumor necrosis factor-alpha (TNFα) release by peripheral blood mononuclear cells. We attribute the increased potency of F-apocynin to its increased lipophilicity, which could facilitate the passage of the drug through the cell membrane. The inhibition of MPO chlorination activity, phagocytosis and TNFα release shows that apocynin and F-apocynin actions are not restricted to reactive oxygen species inhibition, but further studies are needed to clarify if these mechanisms are related. Like apocynin, F-apocynin did not show cell toxicity, and is a strong candidate for use in the treatment of inflammatory diseases.
Authors:
Ana Carolina de Almeida; Otávio Cabral Marques; Christina Arslanian; Antonio Condino-Neto; Valdecir F Ximenes
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2011-04-09
Journal Detail:
Title:  European journal of pharmacology     Volume:  660     ISSN:  1879-0712     ISO Abbreviation:  Eur. J. Pharmacol.     Publication Date:  2011 Jun 
Date Detail:
Created Date:  2011-05-17     Completed Date:  2011-09-06     Revised Date:  2012-08-08    
Medline Journal Info:
Nlm Unique ID:  1254354     Medline TA:  Eur J Pharmacol     Country:  Netherlands    
Other Details:
Languages:  eng     Pagination:  445-53     Citation Subset:  IM    
Copyright Information:
Copyright © 2011 Elsevier B.V. All rights reserved.
Affiliation:
Departamento de Química, Faculdade de Ciências, UNESP-Universidade Estadual Paulista Julio de Mesquita Filho, Bauru, SP, Brazil. carualmeida@gmail.com
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MeSH Terms
Descriptor/Qualifier:
Acetophenones / chemistry*,  metabolism,  pharmacology,  toxicity
Anti-Inflammatory Agents, Non-Steroidal / chemistry,  metabolism,  pharmacology,  toxicity
Candida albicans / physiology
Cell Membrane / drug effects,  metabolism
Guaiacol / analogs & derivatives*,  chemistry,  metabolism,  pharmacology,  toxicity
Humans
Hydrophobic and Hydrophilic Interactions
Hypochlorous Acid / metabolism
Leukocytes / drug effects*,  immunology,  metabolism,  microbiology
Leukocytes, Mononuclear / drug effects,  metabolism,  secretion
Neutrophils / drug effects,  metabolism,  secretion
Oxidants / biosynthesis*
Peroxidase / metabolism
Phagocytosis / drug effects*
Reactive Oxygen Species / metabolism
Staphylococcus aureus / physiology
Superoxides / metabolism
Tumor Necrosis Factor-alpha / secretion
Chemical
Reg. No./Substance:
0/Acetophenones; 0/Anti-Inflammatory Agents, Non-Steroidal; 0/Oxidants; 0/Reactive Oxygen Species; 0/Tumor Necrosis Factor-alpha; 11062-77-4/Superoxides; 450-93-1/4-fluoroguaiacol; 498-02-2/acetovanillone; 7790-92-3/Hypochlorous Acid; 90-05-1/Guaiacol; EC 1.11.1.7/Peroxidase

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