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Synthesis and Antiangiogenic Activity of New Silybin Galloyl Esters
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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, ORCIDSource Title Journal of Medicinal Chemistry. - : American Chemical Society - ISSN 0022-2623
Roč. 54, č. 20 (2011), s. 7397-7407Number 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
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