About: Discovery of the first non-planar fiavonoid that can strongly inhibit xanthine coddase: protoapigenone 1 '-O-propargyl ether

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About: Discovery of the first non-planar fiavonoid that can strongly inhibit xanthine coddase: protoapigenone 1 '-O-propargyl ether Goto Sponge NotDistinct Permalink

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
Description	Xanthine oxidase (XO) is a key enzyme in purine metabolism with an important role in various pathologies. Several flavonoids have been reported for their capacity to inhibit this enzyme, and, for these compounds, the ability to adopt a planar 3D structure has been accepted as fundamental prerequisite for such activity. Here we report the in vitro investigation of a series of non-planar protoflavone derivatives as XO inhibitors, among which protoapigenone 1'-O-propargyl ether was found to be an efficient competitive inhibitor of the enzyme with an IC50 value of 3.61 mu M, significantly (p { 0.001) stronger than the anti-gout drug allopurinol (IC50 = 8.72 mu M). Methoxy substitution at C-7, however, resulted in complete loss of activity. In silico docking supported the observed structure-activity relationships, based on which a 'planar structure' itself can no longer be considered as a criterion for flavonoid-type inhibitors of XO. Xanthine oxidase (XO) is a key enzyme in purine metabolism with an important role in various pathologies. Several flavonoids have been reported for their capacity to inhibit this enzyme, and, for these compounds, the ability to adopt a planar 3D structure has been accepted as fundamental prerequisite for such activity. Here we report the in vitro investigation of a series of non-planar protoflavone derivatives as XO inhibitors, among which protoapigenone 1'-O-propargyl ether was found to be an efficient competitive inhibitor of the enzyme with an IC50 value of 3.61 mu M, significantly (p { 0.001) stronger than the anti-gout drug allopurinol (IC50 = 8.72 mu M). Methoxy substitution at C-7, however, resulted in complete loss of activity. In silico docking supported the observed structure-activity relationships, based on which a 'planar structure' itself can no longer be considered as a criterion for flavonoid-type inhibitors of XO. (en)
Title	Discovery of the first non-planar fiavonoid that can strongly inhibit xanthine coddase: protoapigenone 1 '-O-propargyl ether Discovery of the first non-planar fiavonoid that can strongly inhibit xanthine coddase: protoapigenone 1 '-O-propargyl ether (en)
skos:prefLabel	Discovery of the first non-planar fiavonoid that can strongly inhibit xanthine coddase: protoapigenone 1 '-O-propargyl ether Discovery of the first non-planar fiavonoid that can strongly inhibit xanthine coddase: protoapigenone 1 '-O-propargyl ether (en)
skos:notation	RIV/61989592:15310/13:33148573!RIV14-MSM-15310___
http://linked.open...avai/predkladatel	Přírodovědecká fakulta
http://linked.open...avai/riv/aktivita	P
http://linked.open...avai/riv/aktivity	P(ED2.1.00/03.0058)
http://linked.open...iv/cisloPeriodika	48
http://linked.open...vai/riv/dodaniDat	2014
http://linked.open...aciTvurceVysledku	Trouillas, Patrick
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Univerzita Palackého v Olomouci / Přírodovědecká fakulta
http://linked.open...dnocenehoVysledku	69836
http://linked.open...ai/riv/idVysledku	RIV/61989592:15310/13:33148573
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	Docking study; Structure-activity relationships; Protoapigenone; Protoflavone; Flavonoid; Xanthine oxidase inhibitor (en)
http://linked.open.../riv/klicoveSlovo	Docking study Protoapigenone Protoflavone Xanthine oxidase inhibitor Flavonoid Structure-activity relationships
http://linked.open...odStatuVydavatele	GB - Spojené království Velké Británie a Severního Irska
http://linked.open...ontrolniKodProRIV	[0D6AE69D904A]
http://linked.open...i/riv/nazevZdroje	Tetrahedron Letters
http://linked.open...in/vavai/riv/obor	CF
http://linked.open...ichTvurcuVysledku	1 (xsd:int)
http://linked.open...cetTvurcuVysledku	8 (xsd:int)
http://linked.open...vavai/riv/projekt	Regional Centre of Advanced Technologies and Materials
http://linked.open...UplatneniVysledku	2013
http://linked.open...v/svazekPeriodika	54
http://linked.open...iv/tvurceVysledku	Trouillas, Patrick Chang, Fang-Rong Chuang, Ta-Wei Danko, Balasz Falkay, George Hunyadi, Attila Martins, Ana Wu, Yang-Chang
http://linked.open...ain/vavai/riv/wos	000326613600032
issn	0040-4039
number of pages	4 (xsd:int)
http://bibframe.org/vocab/doi	10.1016/j.tetlet.2013.09.087
http://localhost/t...ganizacniJednotka	15310

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