About: Synthesis and Antiangiogenic Activity of New Silybin Galloyl Esters

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An Entity of Type : http://linked.opendata.cz/ontology/domain/vavai/Vysledek, within Data Space : linked.opendata.cz associated with source document(s)

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
Description	The synthesis of various silybin monogalloyl esters was developed, and their antiangiogenic activities were evaluated in a variety of in vitro tests with human umbilical vein endothelial cells (HUVECs). A structure-activity relationship (SAR) study found the regioselectivity of the silybin galloylation to be highly significant. Silybin (as an equimolar mixture of two diastereomers A and B) exhibited quite poor antiangiogenic activities, whereas its B isomer is more active than silybin A. Galloylation of phenolic OH groups of natural silybin (a mixture of both isomers) leads to increases in their antiangiogenic activities, which is more apparent with the 7-OH than the 20-OH. In contrast, gallates at aliphatic OH groups either had a comparable activity to the parent compound or are even worse than silybin, which was observed in the case of 3-O-galloylsilybin. The most effective 7-O-galloylsilybin has also been prepared from pure silybins A and B. B isomer was more active than A isomer The synthesis of various silybin monogalloyl esters was developed, and their antiangiogenic activities were evaluated in a variety of in vitro tests with human umbilical vein endothelial cells (HUVECs). A structure-activity relationship (SAR) study found the regioselectivity of the silybin galloylation to be highly significant. Silybin (as an equimolar mixture of two diastereomers A and B) exhibited quite poor antiangiogenic activities, whereas its B isomer is more active than silybin A. Galloylation of phenolic OH groups of natural silybin (a mixture of both isomers) leads to increases in their antiangiogenic activities, which is more apparent with the 7-OH than the 20-OH. In contrast, gallates at aliphatic OH groups either had a comparable activity to the parent compound or are even worse than silybin, which was observed in the case of 3-O-galloylsilybin. The most effective 7-O-galloylsilybin has also been prepared from pure silybins A and B. B isomer was more active than A isomer (en)
Title	Synthesis and Antiangiogenic Activity of New Silybin Galloyl Esters Synthesis and Antiangiogenic Activity of New Silybin Galloyl Esters (en)
skos:prefLabel	Synthesis and Antiangiogenic Activity of New Silybin Galloyl Esters Synthesis and Antiangiogenic Activity of New Silybin Galloyl Esters (en)
skos:notation	RIV/61388971:_____/11:00369330!RIV12-AV0-61388971
http://linked.open...avai/predkladatel	Mikrobiologický ústav AV ČR, v.v.i.
http://linked.open...avai/riv/aktivita	P Z
http://linked.open...avai/riv/aktivity	P(GAP207/10/0288), P(GAP301/11/0767), P(OC08049), Z(AV0Z50200510), Z(MSM6198959216)
http://linked.open...iv/cisloPeriodika	20
http://linked.open...vai/riv/dodaniDat	2012
http://linked.open...aciTvurceVysledku	Gažák, Radek Kuzma, Marek Křen, Vladimír Marhol, Petr Fuksová, Kateřina
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	Mikrobiologický ústav AV ČR, v. v. i.
http://linked.open...dnocenehoVysledku	233848
http://linked.open...ai/riv/idVysledku	RIV/61388971:_____/11:00369330
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	Silybin; gallates; HUVEC (en)
http://linked.open.../riv/klicoveSlovo	Silybin HUVEC gallates
http://linked.open...odStatuVydavatele	US - Spojené státy americké
http://linked.open...ontrolniKodProRIV	[5CDAD1B70A12]
http://linked.open...i/riv/nazevZdroje	Journal of Medicinal Chemistry
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	5 (xsd:int)
http://linked.open...cetTvurcuVysledku	9 (xsd:int)
http://linked.open...vavai/riv/projekt	Isosilybin: Combined chemo-enzymatic approaches for preparation of optically pure stereoisomers and derivatives. Inhibitors of Angiogenesis: Design, Synthesis and Biological Exploitation Modulation of intestinal inflammation and nitric oxide production by quercetin and its conjugates
http://linked.open...UplatneniVysledku	2011
http://linked.open...v/svazekPeriodika	54
http://linked.open...iv/tvurceVysledku	Gažák, Radek Křen, Vladimír Kuzma, Marek Ulrichová, J. Marhol, Petr Fuksová, Kateřina Medina, M. A. Oborná, I. Valentová, K.
http://linked.open...ain/vavai/riv/wos	000296205900031
http://linked.open...n/vavai/riv/zamer	Microorganisms in Research and Biotechnology Modulation of signalling and regulatory pathways in normal and cancer cells
issn	0022-2623
number of pages	11 (xsd:int)
http://bibframe.org/vocab/doi	10.1021/jm201034h
is http://linked.open...avai/riv/vysledek of	Synthesis and Antiangiogenic Activity of New Silybin Galloyl Esters Synthesis and Antiangiogenic Activity of New Silybin Galloyl Esters

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