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Statements

Subject Item
n2:RIV%2F61989592%3A15310%2F13%3A33148573%21RIV14-MSM-15310___
rdf:type
n10:Vysledek skos:Concept
dcterms: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.
dcterms: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
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
skos:notation
RIV/61989592:15310/13:33148573!RIV14-MSM-15310___
n10:predkladatel
n11:orjk%3A15310
n3:aktivita
n7:P
n3:aktivity
P(ED2.1.00/03.0058)
n3:cisloPeriodika
48
n3:dodaniDat
n8:2014
n3:domaciTvurceVysledku
Trouillas, Patrick
n3:druhVysledku
n9:J
n3:duvernostUdaju
n12:S
n3:entitaPredkladatele
n16:predkladatel
n3:idSjednocenehoVysledku
69836
n3:idVysledku
RIV/61989592:15310/13:33148573
n3:jazykVysledku
n17:eng
n3:klicovaSlova
Docking study; Structure-activity relationships; Protoapigenone; Protoflavone; Flavonoid; Xanthine oxidase inhibitor
n3:klicoveSlovo
n4:Docking%20study n4:Xanthine%20oxidase%20inhibitor n4:Structure-activity%20relationships n4:Protoflavone n4:Flavonoid n4:Protoapigenone
n3:kodStatuVydavatele
GB - Spojené království Velké Británie a Severního Irska
n3:kontrolniKodProRIV
[0D6AE69D904A]
n3:nazevZdroje
Tetrahedron Letters
n3:obor
n18:CF
n3:pocetDomacichTvurcuVysledku
1
n3:pocetTvurcuVysledku
8
n3:projekt
n14:ED2.1.00%2F03.0058
n3:rokUplatneniVysledku
n8:2013
n3:svazekPeriodika
54
n3:tvurceVysledku
Chuang, Ta-Wei Chang, Fang-Rong Falkay, George Hunyadi, Attila Trouillas, Patrick Martins, Ana Danko, Balasz Wu, Yang-Chang
n3:wos
000326613600032
s:issn
0040-4039
s:numberOfPages
4
n19:doi
10.1016/j.tetlet.2013.09.087
n5:organizacniJednotka
15310