Antioxidant properties of propargylamine derivatives: assessment of their ability to scavenge peroxynitrite

A series of arylpropargylamines, variously substituted in the hydrogen in p‐position and in the propargyl moiety, were studied as potential peroxynitrite scavengers. The scavenging activity of these compounds was evaluated through peroxynitrite (ONOO−)‐mediated oxidation of dichlorofluorescin and li...

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Bibliographic Details
Published in:Journal of pharmacy and pharmacology 2006-04, Vol.58 (4), p.561-565
Main Authors: Dragoni, Stefania, Porcari, Valentina, Valoti, Massimo, Travagli, Massimo, Castagnolo, Daniele
Format: Article
Language:English
Subjects:
Antioxidants - analysis
Antioxidants - chemistry
Antioxidants - metabolism
Dose-Response Relationship, Drug
Free Radical Scavengers - analysis
Free Radical Scavengers - chemistry
Free Radical Scavengers - metabolism
Pargyline - analogs & derivatives
Pargyline - analysis
Pargyline - chemistry
Pargyline - metabolism
Peroxynitrous Acid - metabolism
Propylamines - analysis
Propylamines - chemistry
Propylamines - metabolism
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Summary:A series of arylpropargylamines, variously substituted in the hydrogen in p‐position and in the propargyl moiety, were studied as potential peroxynitrite scavengers. The scavenging activity of these compounds was evaluated through peroxynitrite (ONOO−)‐mediated oxidation of dichlorofluorescin and linoleic acid by measuring the dichlorofluorescein formation and oxygen consumption, respectively. Among tested compounds, only 1‐phenylpropargylamine (AP3) promoted concentration‐dependent inhibition of ONOO−‐induced dichlorofluorescin and linoleic acid oxidation with IC50 values of 637 and 63 μm, respectively. The AP3 spectral changes in UV‐visible absorbance properties in the presence of peroxynitrite suggested the formation of a new compound. This was identified by gas‐chromatograph‐mass spectrometer analysis as phenylpropargyl alcohol. Structure—activity relationship analysis indicated that the scavenging activity of AP3 was due to the aminopropargyl moiety and availability of the nitrogen electron pair. This data suggested that AP3 could be considered a lead compound for the synthesis of new ONOO− scavenger derivatives.
ISSN:0022-3573
2042-7158
DOI:10.1211/jpp.58.4.0016