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Synthesis and Antiangiogenic Activity of New Silybin Galloyl Esters

SYSNO ASEP	0369330
Document Type	J - Journal Article
R&D Document Type	Journal Article
Subsidiary J	Článek ve WOS
Title	Synthesis and Antiangiogenic Activity of New Silybin Galloyl Esters
Author(s)	Gažák, Radek (MBU-M)_{RID, ORCID} Valentová, K. (CZ) Fuksová, Kateřina (MBU-M)_RID Marhol, Petr (MBU-M)_RID Kuzma, Marek (MBU-M)_{ORCID, RID} Medina, M. A. (ES) Oborná, I. (CZ) Ulrichová, J. (CZ) Křen, Vladimír (MBU-M)_{RID, ORCID}
Source Title	Journal of Medicinal Chemistry. - : American Chemical Society - ISSN 0022-2623 Roč. 54, č. 20 (2011), s. 7397-7407
Number of pages	11 s.
Language	eng - English
Country	US - United States
Keywords	Silybin ; gallates ; HUVEC
Subject RIV	CC - Organic Chemistry
R&D Projects	GAP207/10/0288 GA ČR - Czech Science Foundation (CSF)
	GAP301/11/0767 GA ČR - Czech Science Foundation (CSF)
	OC08049 GA MŠMT - Ministry of Education, Youth and Sports (MEYS)
CEZ	AV0Z50200510 - MBU-M (2005-2011)
UT WOS	000296205900031
DOI	10.1021/jm201034h
Annotation	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
Workplace	Institute of Microbiology
Contact	Eliška Spurná, eliska.spurna@biomed.cas.cz, Tel.: 241 062 231
Year of Publishing	2012

Number of the records: 1